You prepared a lot. Trying to go over any topic that could possibly come up. Now, an executive at your company — or an interviewer — asks you a question you hadn’t quite thought about in that exact same way.

That’s when it hits. Your attention shifts to how you’re handling the question. You’re thinking less about the question itself and more about how you’re feeling judged. Evaluated. You freeze — for a beat. Your breathing shortens and your heart beats slightly harder than normal.

As your nervous system reacts, you begin to answer the question. You feel slightly out of body as you speak — you can hear yourself talking faster and with more words than usual. You’re worried about the impression you’re making as you speak.

Afterwards, you can’t exactly tell how it went, but you feel a vague sense it wasn’t as good as you wanted.

One underlying fear in executive communication is: “What will I do when somebody asks me a question I don’t know the answer to?” What will they think of me?

I hear descriptions of this type of moment in conversations I have with product leaders. I’ve felt it myself.

It’s often framed as “I want to be better at communicating with the execs at my company.”

But how do you get better at these moments?

There are some tactics that can help you communicate better in these contexts. Thinking about how you’d structure what you say so you’re crisp and organized mentally is helpful. At times, I’ve found breath work useful before important meetings. It would help me more easily notice when I’d react, pause, and bring my attention back to the conversation.

The understandable response: prepare harder.

Past those basics, though, the usual instinct for improving exec communication is to just prepare harder. The problem is this can lead to overdosing on prep. Preparation, after all, gives you confidence, right? More is better.

Not always. There are certainly helpful levels of preparation. Paired with some practice, this helps create familiarity with the material, priming your mind to speak more clearly and improving your confidence. This is about knowing your work and your business, and spending time anticipating a few key scenarios that could come up.

Where preparation is less helpful is when it becomes more about trying to guarantee you’ll never be asked anything you haven’t seen beforehand. Think about this: Are you preparing to lead and contribute to a productive conversation, or trying to make sure you never feel exposed?

Tactics and prep are not enough to address the whole problem of these moments under pressure. But what happens when you stop treating senior-level conversations — or job interviews — like exams, and instead imagine them as opportunities to share your thinking?

Moving from answering to contributing

As you move into or interview for more senior roles, more of the questions teams deal with involve incomplete information, competing priorities, and tradeoffs. You’re being asked for some perspective before an outcome is clear. Often, no one knows the best course of action yet — so what should we do?

This means effective answers are more about being willing to offer your view without knowing whether it will be welcomed, and being open to what you hear back.

A quick example:

“Why aren’t we moving faster?”

You could start listing everything the team has done or faced. Or you could offer your own assessment:

“I think we’re spreading the team across too many priorities. I’d pause two of them.”

The exec may disagree. But now you have something useful to discuss: which priorities, what it would cost, and what evidence might change your current recommendation.

Why is this so hard?

We learn to succeed in school and earlier years of work by being more focused on getting right answers. You learn later in your career that even better answers are different: sharp, opinionated points of view that are yours. Perspective when the path is not clear stands out. You’re saying what you think.

The freedom of that honesty comes in exchange for your own willingness to risk hearing disagreement. You can care about a discussion outcome without needing someone to agree with your first answer. In an interview, this means allowing the conversation to reveal whether the fit is right for both of you.

What you’re doing is letting someone see how you think, including how you respond when that thinking is challenged. You’re showing you care about reaching a sound answer as a team. You have clear perspectives, but you’re open to revising your first answer.

Stein, a basketball performance coach, noticed how intentional Curry was about everything he did at the camp. He’d arrive early to workouts, wanting the extra time to shoot hoops. Crazily, he wouldn’t leave the gym until he swished five consecutive free throws. The ball touching the rim even once meant starting all over.

Stein later told this story in a YouTube video: he had seen someone whose everyday habits matched his vision. Curry knew what he valued and built his days around that.

In coaching and advising conversations I’m in, we sometimes start one step earlier: does what you’re spending your time on match what matters to you? It’s a simple question. You list 2-3 things that are most important, then compare that list to how life is unfolding.

You might realize you want to visit your parents more often, take better care of your health, or make room for new creative projects. But the way your work is structured leaves little time or energy for those things to actually happen. You may find you’re spending time on things at work that aren’t even the most valuable things to focus on at work. Man, I’ve lived that.

The values vs. time gap was also something Charlene and I looked at before I decided to make a work change at the end of last year. We increasingly valued helping people, travel, outdoor activities, and visiting our now older sons wherever they were.

But my time didn’t fully map to those things. My days were filled with wall-to-wall Slack problem-solving from early in the morning until the evening. “Deep work” would happen over weekends. Work-related travel had me away from my family at times.

Stress and my own preoccupation with whatever work problem needed solving were consuming more of my headspace than I wanted. I was working on something meaningful that helped people and I enjoyed my teams, but the math didn’t fully add up anymore.

Hearing Charlene softly explain that our sons were concerned about me — and only telling her that — hit me pretty hard. They knew I was busy and didn’t want to bother me, but they were worried. That became part of our conversation about making a change.

We had been fitting life, travel, and family around company work, into gaps that were small. We decided to work backward from the life we wanted to create and evolve a work setup around that. I moved from corporate work that I’d done for 25 years into a solo coaching and advisory practice where I controlled my time.

The point is not that everyone should leave their job. Not everyone has that flexibility or desire given life stage and context. You could deeply value completing an important project at work, or a team you’re building, or the impact you can create with your skills. Plus, there are lots of smaller changes that can help if you notice a values versus time gap. It’s the noticing that’s important.

Here’s a concrete way to play with this that I learned from Katia Verresen. Surf through your phone’s camera roll, with your favorite music on, and look for the most meaningful past moments in time. Go back over the last year. Notice patterns and pick a few moments to consider even more deeply.

Ask yourself what made those moments important or memorable to you. Could be work or personal contexts.

Then imagine scenarios where you create more moments like that in an ordinary month, quarter, or year. Of course, not every meaningful moment gets photographed. But a quick camera roll surf helps jog the memory. Then you can scan your calendar with those patterns in mind. Do you make room for those things?

Reaching a goal of any kind doesn’t necessarily make you happier. In Sheldon and Elliot’s 1999 research, people put more sustained effort into goals that matched their own values. Plus, achieving those goals brought greater gains in well-being.

The authors also describe how we can, yes, sometimes go after goals shaped by other people’s expectations or our sense of what we “should” do.

I still surf my camera roll every so often to check what pops for me looking backwards versus how I’m spending my time looking forward. If you try it, here are three basic questions I noodle on, too:

1. What are my meaningful moments telling me about what matters?

2. Where — and how often — does that show up in how I spend my time?

3. What’s one change I could make this week to create more room?

Let me know how it goes. You can reply to this email if you like.

“Colonel, the 6 a.m. flight was the first one off the base?”

That’s the line a few minutes into the courtroom scene in A Few Good Men. Lieutenant Kaffee is beginning his cat-and-mouse game with Colonel Jessep.

I think our family’s watched that scene at least 50 different times, in a few different cities. We’re locked in every time.

Any one of the four of us can pick up a thread of the dialogue, and any other member of the family can then drop into character and roll out the rest of the scene perfectly. The funniest part is we all do the Nicholson stuff so differently, but I insist I can get the closest to the real thing:

“Son, we live in a world that has walls, and those walls have to be guarded by men with guns. Who’s going to do it? You? You, Lieutenant Weinberg?”

Knowing what’s coming as you watch Cruise or Nicholson doesn’t change the tension or how the scene sucks you in.

Kaffee has pretty much figured it out. Earlier in the movie, he, Weinberg, and Galloway talk themselves — and us — through how they want to get Jessep to say it. Jessep definitely knows what happened.

The issue is getting Jessep to say the thing out loud.

Subscribe now

I’ve seen moments like this come up in conversations I’m in, whether coaching or just connecting with people.

We’ve all been in contexts where it would definitely help if a truth were said, right?

“This project makes no sense right now.” But nobody says it.

Or, “I’m not sure I can keep working at this crazy pace.” But then the person works another weekend.

Times where a sharp, clear perspective is held in mind, but is not said in the room. Been there? I have.

There’s sometimes a gap between what’s in mind and what gets said. This creates stress on its own, and real-world things happen. A project that should end moves forward without anyone questioning it. Another weekend disappears into work — even though the sun is out. We can feel the hard parts happening downstream without always tracing them back to a conversation we didn’t have.

Sometimes this happens because of deference or people-pleasing. Speaking out can carry real risks: conflict with a manager, damage to a relationship, or a fear of slowly losing your job.

The Abilene Paradox illustrates this effect. The concept was outlined in 1974 by management thinker Dr. Jerry B. Harvey, based on a personal story. Harvey was relaxing with his wife and her parents, playing dominoes on a hot Texas afternoon, when his father-in-law suggested driving 53 miles to Abilene for dinner, with zero air conditioning.

No one wanted to make the hot, uncomfortable trip. But everyone agreed to go anyway, because each person assumed the others wanted to. No one wanted to cause friction. A miserable trip ensued. Later, everyone found out after they returned home that no one actually wanted to go.

Even the father-in-law who proposed the trip didn’t want to go. He thought the others were bored. Everyone wanted to stay home, and somehow they all agreed to leave.

But really, why is it sometimes so hard to say what we already know?

I used to frame the answer to myself and others as “hey, just speak up more.” But over time, that started to feel like an oversimplification.

“Speak up more” turns the puzzle into a communication problem. Clear, crisp communication can help with many situations, whether at work, with friends, or with family. But talking more is not the final answer.

Another version of this puzzle comes up in quieter conversations: when you are trying to understand what you yourself really think.

There’s a moment like this one back in A Few Good Men. Over a seafood dinner, Commander Galloway starts listing her accomplishments and commendations to Kaffee. Kaffee asks why she keeps giving him her résumé. “I want you to think I’m a good lawyer.” She’s saying what she really wants.

Have you ever been in a one-on-one conversation with someone who steps through a set of thoughts they’re having, explains and rationalizes, and then says something shocking and blunt like “I don’t want to work there anymore”?

That type of reveal can hit you both hard. Sometimes the person saying it is just as surprised as you are. You think: where was this five minutes ago? Did talking out loud help them find the words?

This isn’t the same problem as deciding whether to challenge a group in a meeting. This is about someone getting clearer about what they think.

This means our question gets a little bit weirder. What does it mean to ‘know’ something before we’re able to say it?

Maybe things we “know” are in different in-progress states at different times. We can feel something, work through it, or even avoid it before we can put it into words. “Knowing” is less of an on/off switch.

Before someone says “I don’t want to work there anymore,” they may have thought they were just in a busy period, or needed more rest. Maybe “I don’t want to work there anymore” is new clarity on what’s been bothering them. It was previously just percolating.

But when you say something out loud—or even journal it—something can change. Sometimes another person helps you find the words. Your working draft thought can become something you can look at. Does this describe what I feel? Do I believe it? What comes next?

Maybe saying is one of the ways “knowing” becomes knowing. It gives you something to test and acknowledge.

“I don’t want to work there anymore” might become “I want to stay, but I can’t keep working this way.”

In 1997, James Pennebaker, Tracy Mayne, and Martha Francis analyzed writing from 177 people across six previous writing experiments. Participants wrote for 15–30 minutes over several sessions about difficult experiences they’d had — trauma, starting college, or losing a job. The researchers tracked how their language changed over time.

Increasing use of words associated with insight and causal thinking—words like “realize,” “understand,” “because,” and “reason”— was associated with fewer illness-related physician visits and fewer self-reported physical symptoms afterward. Their changing language suggested they were increasingly putting their connections and understanding into words.

Perhaps the writing wasn’t just recording their thinking. It was helping them work through something.

The next time you’re working through an idea alone, or in a crazy Zoom meeting, try asking this:

What’s the important true thing that isn’t being said?

Share

On October 27, 2016, I was in Shanghai, traveling through China with about 15 members of LinkedIn’s research and development team. We were visiting a series of companies in different cities, learning about how those teams thought about building their apps.

On this October day, we visited Musical.ly’s offices, met some of the team and had a relaxed conversation with the app’s co-founder, Alex Zhu. We wanted to learn more about Musical.ly, which at the time was growing fast. In some ways this trip to China, and the visit to the Musical.ly offices, felt like looking into the future.

Subscribe now

Today in 2026, as AI transforms how we work, there is a glut of conversation about taste. “Taste will be what differentiates product builders” is the usual frame, as AI tools make the building easier and more accessible.

But taste (even when defined well, and it rarely is) is evaluating outputs that already exist.

The scarcer and more valuable act in the future will be about generating inputs. Seeing an original spark of insight and creating something totally new in the first place.

On that day in 2016, Alex and a couple of product managers crowded into a cramped room with plain white walls and a very large whiteboard. He began riffing on how social networks worked, and why they built Musical.ly the way they did. “I’ll just write at the whiteboard if something comes up.” He did.

One insight from Alex’s talk stayed with me. Before returning to Shanghai, he told us, he’d spent time working a few larger company roles in Silicon Valley, then had a startup idea to build an educational app. His commute in those days was taking Caltrain up and down the Peninsula between Mountain View and San Francisco.

Alex described observing teenagers on those train rides passing time together: listening to music and shooting photos or videos. He saw them experimenting with leaving the speaker on when shooting so the music from the phone would be in the video clip. The teens shared what they did on their phones with each other, laughing and having fun. Up and down the Peninsula.

This was an organic human workaround happening on those daily commutes. The teens were creating a mix of media experiences for themselves. At the time, no existing tool or app made this easy. Alex noticed what was happening.

He decided to pivot his not very popular educational app into what would become Musical.ly, building a new app around these observations. The team built the new app quickly and released it in 2014.

The new app became a breakout hit, huge with American teenagers. Teens used the app all the time to video themselves lip-syncing and dancing to fifteen-second clips of a song. On Vine or Instagram you experienced the app by person. Musical.ly was organized around songs.

Musical.ly, and Zhu, eventually became part of ByteDance, when that company bought the app in November 2017 and folded it into their other video efforts. What came next was TikTok, using much of what Musical.ly had built and learned.

It’s the noticing that’s the hard part of any initial insight.

The train ride Alex traveled was the same commute I took many times, for a few jobs I’ve had in the Bay Area. It’s possible that I was on the train some random day at the same time Alex was. But I didn’t notice what he noticed. If I’m honest, I was probably buried in my laptop catching up on email. Not making time for seeing the world around me.

I’m still working on observing and noticing more, and it always starts with making time for it. Since you’re reading this now, look up for a second. What do you notice?

Then ask yourself: What did you observe this week that nobody has built yet?

Share

Hi, I’m Jeff. I spent 25 years building product at LinkedIn, Facebook, Headspace, and Included Health. Now I coach senior product leaders through the moments where the old playbook stops working: a bigger scope, a new company, communicating at the exec level, or figuring out what’s next. I work with a small number of 1:1 clients in six-month engagements, and every one started with a single conversation. If that’s you, or someone on your team — reply to this email. I read and answer every one.

It was 7:45 in the morning in Seattle on January 8. I had finished up my time at Included Health at the end of 2025, and we were up north to spend some family time over New Year’s, as our older son had moved to the area. I was sitting at the dining room table in the morning dark of our Airbnb.

I remember getting up, going out onto a patio, and taking a quick snapshot of the pink and blue sky over Elliott Bay, thinking about what would come next in 2026.

Since that morning I’ve had close to 200 different conversations with senior product leaders, in a period of massive change in how we work.

TLDR: Underneath many questions is some form of self-doubt.

As I shifted to exec coaching and advising, I distilled a year of notebook writing, voice memos, and my own vibe assessment across all chats and coffees so far this year. One side note: Tartine Manufactory wins for top in-person coffee location. I recommend the morning bun and a cappuccino.

Here are five ideas plus two mega themes I’m hearing about often and loudly.

Idea 1: “What do I actually want next?” This one spans levels of seniority. The meta pattern I’m seeing: it’s rare for people to take time to step back and examine whether the path they’re on is what they really want. But people are doing this more often as a function of the time we’re in. I’ve heard different flavors of this all year from:

• Should I work full-time or go solo?

• Should I move away from a difficult environment?

• Am I selling myself short in my current role?

• How do I get into a better environment to work on AI?

• Should I switch careers away from tech entirely into my true passion?

Idea 2: The “ROI” conversation. The common theme is people examining their own ROI on their increasingly intense effort. I see a few different situations come up:

• People in a role who feel stuck and want to operate at a higher level and want help with how to get there. This first group wants to assess and work on what’s holding them back.

• People who chose smaller on purpose — to learn, to get into a better company, or to reduce the craziness. The second group wants to sanity-check the plan or work through regret of a past choice.

• A third group is in this frame of mind thinking whether their effort is better served inside of the company they’re in or perhaps by trying something on their own, particularly given how AI tools can help that.

For ideas 1 and 2, I recommend thinking about: What do you most value? What are your most true priorities? When you feel most energized, what are you usually doing?

Something to read:

Make Time to Ask the Pause Question - Why the best fix isn’t always a tactic.

How to check your values vs. time gap - Steph Curry, your camera roll, and a few simple questions can help.

Idea 3: “What is my unique differentiation?” This theme is about: “How am I different from other leaders and what should I focus on to better bring that to life?” Sometimes this one feels more like imposter syndrome. Other times it’s closer to “what do I actually want next?” (See #1.) An underlying theme in this one is the concern about AI commodifying aspects of past roles. In this context, unique product POV and judgment become even more of a separator. But in conversations, leaders want some help fleshing out how this comes to life for them and what they should work on next.

For idea 3, I recommend thinking about: What makes you unique? Being very clear about what your team or company needs and focusing right there vs overdosing on minor tasks all over the place.

Something to read:

Run the ‘Cocktail Test’ over your priority list - How a few Cuban cocktails may just help clarify what actually matters most.

You Get Paid for Shower Thinking — What Jeff Weiner’s blank calendar taught me about where good ideas come from.

Idea 4: Executive communication, but with underlying drivers. This can start as wanting to be more crisp when communicating at increasing levels of company altitude. But the underlying driver is usually confidence or perfectionism, both affecting communication in the moment. So, over-explaining, freezing under pressure, challenges with probing or pushing others or just discomfort about senior-level communications all come up here. This is a rich area with a lot of tactical solutions that can help, but the core issues usually come back.

If this one’s yours, reading can start here:

Answer First: A Simple Framework for Executive Communication — The lesson I learned the hard way in a room full of leaders.

There is no answer key — What changes when you stop treating exec communication like an exam.

Idea 5: Saying the important true thing out loud. Related to communication (#4) but different. This is about being true vs. being crisp. Sharp, clear perspectives held in mind, but someone finding it difficult to state them in rooms. Three versions I’ve seen:
Deference by default. Forms of people-pleasing. Or, asking permission where none is needed.

This is deeper than just “speak up more,” which is an oversimplification. The downstream cost is tough too: a POV missing from a big decision, overwork based on lack of boundaries, etc. It’s also at times hard to connect the downstream cost to this cause at first.

If you want to go deeper on people-pleasing, start here:

People-Pleasing May Be Holding You Back — How to spot this pattern, push through discomfort, and unlock better work—for yourself and your team.

What’s the important true thing that hasn’t been said? — If Kendrick gave an order that Santiago wasn’t to be touched, why did he have to be transferred?

Mega theme A: Self-doubt/imposter thinking. This one threads through many of the above. Sometimes it pre-dates the career altogether. Performance can mask it or help it subside for periods of time, but then it resurfaces. These conversations are often about figuring out what the right question is and then running small experiments to build confidence. This type of self-questioning can show up at first as questions that are more tactical and skill-oriented — “How do I get better at X?” Even when you keep deeper causes in mind, tactical tips are frequently where early experimentation starts.

Mega theme B: The org is the emerging AI problem. This also weaves through the above themes as teams work through the sea change of AI happening in real time. Two pieces here:

• How to help teams move past AI demos and experimentation (at times performative only) into rewiring how a company works. This is moving past which model or tool to use in a flurry of options that constantly shift. The harder question is: What is our governance and workflow model?

• Then there are broader people issues: Org shape changes, career paths, and where differentiated value emerges in a revised chain of work as executional costs drop.

This mega theme is the organizational version of #1 (What do we want next?) especially in contexts outside of AI-native-from-scratch companies. What’s really hard is evolving an existing company. The core issues are always human systems and people problems.

I’m curious what themes you’re seeing most. Try this: pick which one feels most relevant to you and ask yourself what you think the driver of that feeling is.

Share

Hi, I’m Jeff. I spent 25 years building product at LinkedIn, Facebook, Headspace, and Included Health. Now I coach senior product leaders through the moments where the old playbook stops working: a bigger scope, a new company, communicating at the exec level, or figuring out what’s next. I work with a small number of 1:1 clients in six-month engagements, and every one started with a single conversation. If that’s you, or someone on your team — reply to this email. I read and answer every one.

Read next:

This is a memory — one person’s lens on a day the world will never forget.

The pager buzzed at 5:53 a.m.

It was on my nightstand, rattling across the wood before I grabbed it and flipped open the little plastic door to show the single line of gray text on a lime green teletype screen. It told me what was happening.

“AP NewsAlert—Plane crashes into World Trade Center, according to television reports.”

When I started my new job in March 2001 as an associate producer at Yahoo! News, they handed me that pager “in case something happens in the news and you need to go to work.”

Pagers were more common at the time for doctors, lawyers, maybe civil servants, and nobody I knew was that clear why I’d need one. My friends and family looked at the thing clipped to my belt with curious glances. My dad, himself a practiced pager wearer, asked me about the pay protocol—did I get double or triple time pay whenever I responded to a page like he did.

“Nope,” I remember telling him. “Some news happens, they page you about it, and you go to work.”

Charlene was already up early to staff a telephone press interview for Cisco. She’d gotten the Trade Center news from a colleague on the call and turned the television on. Charlene’s team had traveled to Atlanta for a trade show, but she was five and a half months pregnant with our first child, so she stayed home.

Charlene told me what was happening, and I showed her my pager. I sat down in the kitchen and used our modem — a few beats of booping and screeching — to connect my work laptop to the Internet and check in. Co-workers were already online working and heading into the office. (Our Yahoo! News team used Yahoo! Messenger to communicate.)

Charlene and I rushed to get ready with the TV on in the background. CNN had already cut into normal programming — the anchors were trying to make sense of what was happening. Back then CNN was cable news; Fox was a much smaller upstart, MSNBC was even smaller. We flipped through the dials to see — NBC, CBS and ABC all broke into coverage interrupting the usual rhythm of their morning talk shows.

American Flight 11 had hit the Trade Center North Tower. Then at 6:03 a.m. our time, United Flight 175 hit the South Tower. CNN showed taped footage of President Bush being told what was happening while he listened to grade school kids reading aloud in a Florida classroom. They were reading The Pet Goat.

Charlene and I headed into work early. Traffic was strangely normal as we drove south on 101 in our 1995 Honda Civic, listening to NPR, trying to keep up.

As we headed to Yahoo!’s campus to drop me off, NPR reported that Flight 77 had hit the Pentagon. Minutes later, the FAA grounded all flights nationwide, something that had never happened before. We heard the White House and U.S. Capitol were being evacuated.

It was 6:48 a.m. The sun was just rising over the Bay Area, obscured by the morning’s gray marine layer.

The pager rattled all morning with more AP and Reuters alerts. FBI investigating reports of hijacking; car bomb explodes outside the State Department (later retracted); large plane down in Pennsylvania; markets suspended.

AP has something called a flash, the wire’s rarest designation, saved for assassinations or moon landings. On 9/11, AP issued two: one for each tower coming down. Both of those arrived shortly after 7 a.m. on the West Coast.

I remember walking into our Yahoo! News cubicles on the second floor of Building B at the company’s gray-and-purple campus in Sunnyvale. The newsroom of the world’s largest news site was a few rows of understated office cubicles in yellow and purple. This was where Yahoo!’s news and media products were built.

Yahoo! News had maybe 15 people working on the news site directly: Engineers, Producers (a role that evolved into Product Managers), Designers, Business Development, and Ad Sales plus the company’s “Full Coverage” editors who hand-edited pages aggregating the most useful links on any topic. Those links, which also showed up alongside many news stories, deliberately pointed users off Yahoo! to the best coverage anywhere. No one else online did that at the time.

There were no reporters on this team. Yahoo! News was aggregation—headlines, photos, and videos from other news brands, all presented together on simple white HTML pages with the original red Yahoo! logo. It was a new way of conceiving of what online news could even be. A media company, but different.

There was a hum of activity in an otherwise quiet office that morning as we dealt with the unprecedented crush of web traffic. We worked to curate and assemble the site’s coverage of an event none of us had ever seen anything like before.

I remember Tony Tam, our lead software engineer, on a conference call working with Yahoo! co-founder David Filo and others to spin up servers from other parts of the company to handle all the news traffic. They stripped the site down to make sure it would load.

Websites for CNN, MSNBC, the New York Times, ABC, and the Washington Post were unreachable at points during the morning as users from around the world overwhelmed servers seeking the latest information. Yahoo! News held up because of its lean, well-written software and light, simple web pages built to load in browsers quickly.

Our GM, Chris McGill, was on the phone discussing whether to pull down the site’s banner ads so pages could load faster—and so readers wouldn’t see ads alongside what were becoming increasingly disturbing stories and images. We did pull ads down for a time. We decided to show every photo that AP gave us, keeping the most disturbing images off of Yahoo.com.

Producers Ron Parsons, Kourosh Karimkhany, and I were making sure news feeds were coming in, deciding which wire services to feature, assembling photo slideshows from material coming in from the scenes, and getting links to video clips into as many stories as possible. There were lots of coordinating calls and troubleshooting with the AP and Reuters news desks. We worked with ABC News to get a live video feed up. For a while that feed only ran on Yahoo! News while ABC News’ own site was down.

The Full Coverage editors—Brad Rubin, John Briggs, Kevin Mooney, Molly McCall, and others—were building coverage pages and working with Yahoo!’s homepage team to take over the top of the page to hand-edit links to stories, photos, and video in a news box built on the fly. The team also added the phone number people could call to donate blood to the Red Cross.

About half of American adults were online, and only 1 in 10 US homes had broadband. Since many workplaces had faster T1 lines (fiber came later), the office desktop web browser—plus television or radio if you could get it at work—was how the world took in the news.

There was occasional chatter as we coordinated or stopped to gasp together at the magnitude of the latest news. We had a couple of TVs with constant live coverage, one mounted on the wall and another propped up on a cubicle. The Sports guys nearby donated their TV to us so we could see it from our cubes while we worked. They wouldn’t be needing it.

There were no smartphones, and no App Store. The iPhone was still six years away. Facebook, YouTube, Instagram, and Twitter didn’t yet exist.

Google was a three-year-old search engine then, and search was the entire company—no news product at all. It famously resorted to putting a text message on its home page telling people to turn on their TV or go to news sites.

In the Yahoo! News room, we were all on autopilot, far removed from the East Coast. The work meant being immersed in the news in real time as it came in. It was a mix of adrenaline and action, with in-between moments of shock.

And whatever we felt that day was nothing compared to what the day actually was: nearly 3,000 people did not come home. The work was meaningful—easily among the most meaningful work I’ve ever done. Some of the coverage survives—in the Wayback Machine, and in the Library of Congress’s September 11 web archive.

I stayed late. Charlene drove herself home, and I came back after dark in a yellow cab.

My pager buzzed with a few more alerts: members of Congress singing “God Bless America” on the Capitol steps; Bush’s Oval Office address; reports of possible survivors in the rubble.

Charlene and I took in the rest of that day from home, sitting next to each other, glued to CNN, talking on the phone with family and friends. Horrified, scared—and together. The stories of all the victims and their families were moving and gut-wrenching.

One of the women killed in one of the plane crashes was a Cisco employee who Charlene remembered. Among the four men who tried to call their families and then fought the hijackers on Flight 93 was a former Cal rugby player, Mark Bingham. I’d covered Cal rugby as a college newspaper reporter and spent a lot of time with the team, and I knew exactly what those guys were like.

With a child on the way in a few months, you’re already pensive about what’s next. I remember questioning what the world would be like for the baby we were going to meet soon. Nobody was at all clear what would come next, and so much did.

By the next day NATO invoked Article 5 for the first time in its history. The markets didn’t reopen until September 17. President Bush’s “War on Terror” address to Congress was a few days later. Over 100,000 airline employees were laid off and a Congressional airline bailout came within two weeks. By October, we had invaded Afghanistan and the Patriot Act was law.

Charlene gave birth to our first son, Nolan, that December, a few days before Christmas.

Thank you to Chris McGill and Kourosh Karimkhany for early reads and added memories.

Share

Sometimes, when we run into a challenge at work, our first instinct is to reach for a new tactic, a framework, a tip, or a prompt to help solve the problem.

It’s the executional lens we most often view hard things through, mostly because that’s the first thing that occurs to us as what would help.

“Do you have a framework for solving X?”

I’ve certainly thought about these types of questions when trying to get better at something happening at work.

How can I get better at speaking to executives? How can I be better at that hard conversation? How do I lead my team more effectively?

These are all understandable questions. And often, there are some useful ideas, tips, or practical techniques that can help.

But some of the most useful breakthroughs I’ve had tended to start as a tactical question and end up somewhere else entirely. Sometimes what first looked like a skill or knowledge problem turned out to have something deeper.

Take the question of improving how you speak in group or leadership settings. In my coaching practice, this is one of the more common areas where clients want to focus and improve.

It’s an important area and there are tactics that can help: answer first, say exactly what you mean, work on ways of improving your in-room presence, and more.

But sometimes the more useful questions are different and point internally instead of at tactics: “Why are you nervous in the first place? When you feel that nervousness in the moment, what does it feel like? What is it about that setting that changes how you show up?”

Questions like these can surface things that an “executive communication” framework wouldn’t fully address.

These deeper questions are harder to surface when we’re moving quickly or staying in pure problem-solving mode. If the goal is simply to fix a challenge and move on, our attention naturally stays on the most visible version of the problem.

There’s a reason for this: psychologists find that under time pressure we tend to “seize and freeze” — we seize the first workable answer and freeze on it. Pausing is hardest exactly when we need it most.1

A pause for reflection can create a little distance from that. That can be a walk, writing a page in a journal, or a real conversation with someone who asks a question you wouldn’t ask yourself.

Jerry Colonna has a question in his book Reboot: Leadership and the Art of Growing Up that always causes me to think about things more deeply:

“How have I been complicit in creating the conditions I say I don’t want?”

That’s a pause question. It’s uncomfortable because it shifts focus from the situation to your own role in it. That’s a different mode of thought — slower, deeper, and sometimes less pleasant.

But sometimes that’s where the insight is. You get a different perspective than a framework can offer.

This is not an argument against tactics or action. Sometimes a tactical problem really is just a tactical problem. It’s only a reminder we sometimes need to pause and ask what else might be causing the challenge.

I’ve found it helpful to think about reflection as part of a loop. Action creates data and experience. Reflection turns that data and experience into learning. And that learning can improve the next action you take.

That middle step is the pause to reflect. Reflection isn’t a break from doing the work. It’s one of the ways we learn from work.

Pausing feels especially relevant now because AI is making tactical knowledge so abundant. AI can give us frameworks, prompts, scripts, examples, and advice instantly. That’s incredibly useful. But it also makes it easier to stay in a constant mode of improving through optimization, always looking for the next tactic or tool.

The risk is that we skip taking that quieter moment to noodle on whether we’re solving the right problem in the first place.

So the next time you reach for a new tactic, try pausing first. Ask whether there’s something underneath that deserves some attention. If it’s helpful to have a conversation with someone about it, go for it.

Every once in a while, that pause may surface something that can change what you decide to do next.

Share

Hi, I’m Jeff. I spent 25 years building product at LinkedIn, Facebook, Headspace, and Included Health. Now I coach senior product leaders through the moments where the old playbook stops working: a bigger scope, a new company, communicating at the exec level, or figuring out what’s next. I work with a small number of 1:1 clients in six-month engagements, and every one started with a single conversation. If that’s you, or someone on your team — reply to this email. I read and answer every one.

The meeting itself was high value for a certain group of folks at the company, but lower value to me. And it was super clear I needed to get out of this thing, especially since it always seemed to take place right when I had a bunch of important deliverables or team problems to solve.

But I was scared about having the conversation with my manager. I was worried about what this person would say. “What do you mean you can’t make my meeting?” The tactical question of just cleaning my calendar up was tougher than I thought.

Subscribe now

So I spent too much time overthinking it, staring at that stacked calendar. Lucky for me, I was working with a coach at the time, provided by the company. She helped me see I was stuck. It was my natural instinct not to disappoint people. It just came from my personality of generally being accommodating and easy to work with. The closer I looked the more I realized this was getting in the way of being better at my job.

In this case, I was creating more weight about the conversation than existed in reality. When I finally spoke with my manager, saying I wasn’t going to be able to make that meeting anymore, the entire conversation lasted about 5 minutes. It was a non-issue.

The learning wasn’t how to clean up my calendar, regardless of who scheduled a meeting. It was more about realizing I had overthought how much I’d be disappointing someone. For me, it was a form of people-pleasing — something I’ve written about before. For others it’s a different fear that can show up under the same kind of question.

I see this play out in conversations I have today. There are times when a tactical question a senior leader asks is really two questions. There’s the surface question that comes first and easiest: “How do I talk to execs more crisply?” But most of the time, that question comes with a deeper layer underneath: “Why am I feeling this way to begin with?”

The tactical question can often become a door to understand something deeper about yourself. “Well, why? What are you worried about? What do you think about when that issue comes up? How does that feel for you?” That kind of curiosity surfaces something that’s a little bit more specific to the person and requires some deeper thinking.

Fixes and frameworks matter, but make time to think about the why behind something. Try and examine if there’s something deeper that’s holding you back.

There are three potential scenarios I’ve lived and seen:

• A problem that can be solved with a tactic or framework.

• A problem where a tactic or framework helps — but there is more there worth thinking about.

• A problem where the tactics and frameworks aren’t the issue at all — the real thing is something deeper in how you’re approaching the issue.

The next time you catch yourself asking “how do I…”, ask the second question with it — “and what makes that feel hard for me?” You don’t have to answer it. Just ask it and notice what comes up. That might be the beginning of getting at the underneath question.

Share

Many coaching conversations start around a tactical question. The good conversations always turn out to have a second question inside.

Hi, I’m Jeff. I spent 25 years building product at LinkedIn, Facebook, Headspace, and Included Health. Now I coach senior product leaders through the moments where the old playbook stops working: a bigger scope, a new company, communicating at the exec level, or figuring out what’s next. I work with a small number of 1:1 clients in six-month engagements, and every one started with a single conversation. If that’s you, or someone on your team — reply to this email. I read and answer every one.

I wrote this post about 11 years ago on another blog and wanted to share it here because it’s relevant to a bunch of conversations I’ve been having lately with senior product leaders.

Book Review: “The Hard Thing About Hard Things.” (The book was originally published in March 2014, but I still highly recommend it.)

“Hard Things” is a fast read and is useful for anyone interested in learning about management, and more specifically, how Silicon Valley companies work. Note: it’s also the book home of one of my all-time favorite business quotes: “This is not checkers; this is motherfuckin’ chess.”

Horowitz’s idea was to write the management book that covers everything most management books never cover: the messy, hard stuff. Real stories from his time as CEO of Loudcloud, which later became Opsware, before it sold to Hewlett-Packard in 2007 for $1.6 billion.

Opsware was in trouble multiple times and in multiple ways from start to finish. In that sense it’s much more like how many companies work. Startups are usually hard, and most die. Not everything is up and to the right.

But my favorite, and in my mind the most useful part of the book, is actually infused throughout — it’s the drop-dead honest and simple way Horowitz has of communicating.

You get a sense for this when you read his take on specific stories or he quotes himself. But you also see it in between the stories in terms of how basic thoughts are conveyed.

Subscribe now

TLDR: Be Simple. Use. As little. Words. As possible. Say exactly what you mean.

Take this example from the story about Horowitz trying to hire a VP of Sales into his struggling company. He has someone he thinks is fantastic in mind, but this person is apparently a little odd.

So board members plus Chairman and co-founder Mark Andreessen disagree and are arguing. The potential hire doesn’t look right. He went to a small school, and he has an off way about him. Horowitz listens and then simply says:

“I agree with every single one of those issues. However, Mark Cranney is a sales savant. He has mastered sales to a level that far exceeds anybody that I have ever known. If he didn’t have the things wrong with him that you enumerated, he wouldn’t be willing to join a company that just traded at thirty-five cents per share; he’d be the CEO of IBM.”

Boom. Simple. This candidate has some issues, but he is exactly what we need right now and oh by the way — let’s get real, we are not exactly playing from a position of strength. Imagine instead how that statement gets mangled by someone who is either not clear about exactly what he (or she) thinks or not willing to just state it:

“Hmmmmm. You have some good points, there. Really. You do. This guy has some positive points, but we’re all agreed we need the best possible hire. I guess I need to take another look at this situation with that in mind and report back to the board in 30 days.”

That statement there is a recipe for delay and then losing the candidate to top it off.

THAT, in the end, is the most valuable message of The Hard Thing About Hard Things. There are some useful, tactical lessons there to be sure. But really, the best lesson is about communicating with little wasted language or B.S.

This is not about being belligerent — just, well, straight. Take the time to know what you think and then say EXACTLY that. Doing so saves time and builds trust, both of which most startups are short on and desperately need.

Eleven years later, in conversations I’m having, the single most common thing I see show up is smart people who know exactly what they think and say the ‘Hmmmmm’ version, or no version at all.

Try the Mark Cranney story move one time this week. Take one moment in a context that matters, settle on what you actually think, then say EXACTLY that.

Let me know how it goes.

Share

The gap between the Cranney version and the ‘Hmmmmm’ version is half of what I work on with coaching clients every week.

Hi, I’m Jeff. I spent 25 years building product at LinkedIn, Facebook, Headspace, and Included Health. Now I coach senior product leaders through the moments where the old playbook stops working: a bigger scope, a new company, communicating at the exec level, or figuring out what’s next. I work with a small number of 1:1 clients in six-month engagements, and every one started with a single conversation. If that’s you, or someone on your team — reply to this email. I read and answer every one.

Coaching update: This week I started working with the Sidebar community as an exec coach. I’ve already met with some leaders in this context: usually working through a new, larger job scope, communicating better at new levels, leading hard transformations, or just thinking about what’s next. If that’s you or someone you know, reply and ping me or visit me here.

⏱ Read time: 4 minutes

I do some of my most creative thinking in the shower.

I’ve had sparks of insight about product directions show up there. (This happened when I was at Headspace, Included Health, and Facebook.) But lots of other thinking sparks show up, too. A better way to communicate something appears. Creative ideas for outside of work. A trip or a piece of writing. I’ve even gotten some good thinking for how to solve a relationship or people problem.

A surprising amount of high-leverage thinking happens right there. You get into that flow of creative rumination, and something pops.

It’s that mindset, when you’re most creative and thoughtful, that can create outsized value in your work. One small insight can change the direction of a project or unlock a difficult problem.

Bottom line: You get paid for shower thinking.

Especially as you take on more senior roles, the value you create comes increasingly from your judgment and standard setting and ideally a small handful of ideas that change what happens next where you are.

But I can’t tell you how many people I’ve talked to, advised, or coached where you ask about their calendar and hear the killer: it’s wall-to-wall 30-minute sessions. The idea that you’re going to do your best thinking in the cracks between those blocks? Forget about it.

And that’s the tension. Companies pay people for creative ideas and the ability to then go execute. But the natural rhythm most companies fall into at any kind of scale rarely creates space for that kind of thinking. And if we’re being honest, we’re often the real drivers of how this shows up in our own schedules. We accept the meetings, and fill the open space.

If you want more of the mental state you find in the shower, you usually have to create it with intention. There’s some good science behind why the shower can be such a creative place to think.

In a 2022 study on what researchers called the “shower effect,” Zachary Irving and colleagues looked at mind-wandering during activities that are somewhat engaging versus boring ones.

They found that mind-wandering was associated with more creative ideas when it happened during something “moderately engaging.” So something like walking, or yeah, showering, occupies just enough of your attention to let creative thinking happen more freely.

That’s different from what a normal company work calendar can do to your brain.

Microsoft’s Human Factors Lab put 14 people in EEG caps while they went through four consecutive 30-minute video meetings. Without breaks, stress-related brain activity built up across the meetings. When the same sessions included even 10-minute breaks, that stress buildup was lower.

When I was at LinkedIn, CEO Jeff Weiner would often talk about how important it was for him to schedule nothing.

He would protect 90 to 120 minutes on his calendar (he called it “buffer time”) with zero meetings and no specific agenda. He described that blank space as one of his most important ways of working.

I’ve found the same basic idea useful, with a few twists of my own.

1. Protect one real block of time.
The exact number matters less than making the space real and yours. Thirty minutes will disappear before you even get out of reactive mode. If you can create a 90-minute block, awesome. If you can only create 45, then start there. Make it real enough that your brain has a chance to go somewhere different.

2. Put that time block where your brain is sharpest.
For me, that’s usually early morning. When I’m struggling to find that kind of space, I’ve even experimented with getting up at 4:30 in the morning. There’s something about working when it’s still dark and nobody else is awake that makes it easier for me to get into that flow.

I’ve also tried listening to a fast song first or doing a quick five-minute Headspace meditation.

Your version may be different. What’s important is knowing when your mind tends to be at its best and protecting that time instead of automatically giving it away.

3. Don’t spend the block at your desk, and definitely don’t spend it catching up on email.
This is the trap for me. You create a blank block on your calendar and then fill it with the Slack or email monster. That isn’t shower thinking. Think about it like the shower. You don’t answer emails and Slack in the shower, do you? (Don’t answer that!)

The idea instead is to try and give your brain something slightly engaging to do but leave enough room for your thoughts to wander. So what are things that do that for you? Try a walk. Getting outside in the sun. Take a shower, even. Whatever helps.

Don’t sit in front of a blank screen and force yourself to have a brilliant idea. Create the conditions where those ideas might pop for you.

To make any of this happen, you don’t have to redesign your entire calendar (though if you ever want to, I wrote a version here).

Try one small experiment this week. Protect a time block. Cancel a meeting (you probably don’t need). Then, take a walk without checking email or Slack. Create a little space for yourself and see what happens to the quality of your thinking.

You might be surprised by what pops.

What’s your best place and mode for shower thinking?

⏱ Read time: 3 minutes

In early 2006, I was working at Yahoo!, back when it had the largest audience on the web. It was a great place to be working as a product person in tech.

I had just moved to a new “startup” inside Yahoo!, building a new service to compete with CNET. My career was going well. I’d recently been promoted to Director.

A friend of my former manager Chris called me one morning with an opportunity.

I still remember doing the phone call from inside one of those small phone booth rooms on the old Yahoo! campus. The guy got right to the point.

“Hey, good to connect,” the guy said. “I’m at this video startup. It’s taking off, video is hot, and we’re doing well. We’re hiring our first product person, and Chris says you’re great at product and would be good to talk to. Would you be interested?”

He even told me a few of the video competitors at the time. “I realize there are like 13 video competitors now, but this thing is working well,” he said. I quickly looked some of them up on my laptop while he continued his pitch. Vimeo, Dailymotion, Metacafe, Revver. Plus a few others. Crowded space!

Then: “We don’t have an office yet, so we’re working out of our VC’s space on Sand Hill. We could meet there.”

I said something like: “I’d love to meet you but I’ll be honest. I’m doing pretty well at Yahoo! I just got promoted. It’s probably unlikely that I’d move. I’m really not looking.”

I never heard back. When someone at one of those super-fast-growing startups is hiring, they move on quickly if you show any vibe of hesitation.

We launched “Yahoo! Tech” that May. Newsweek said it might “portend what the media will look like in coming decades.”

That little video startup? It turned out to be YouTube.

Google bought them in October 2006 for $1.65 billion.

Fuck.

Right?

Yes and no. I looked at a future door using too much present tense data.

Though at the time this felt like a miss, the path I ended up on opened up new doors that affected my life in ways I couldn’t have imagined.

I definitely take more coffees, say yes more often, and explore new things instead of defaulting to being satisfied. That’s lived on for me as a lesson.

But I also went on to work at companies and meet people, both of which compounded into interesting roles, relationships, and fun. For example, someone I met at LinkedIn later connected me to Included Health.

It all ends up working when you zoom out and just keep moving.

Every decision or choice simultaneously closes off opportunities, but also creates new ones. If you take advantage of the new ones, missed ones don’t turn out to be so bad. They’re learnings.

Oh, and always take that coffee.

My first roles in what became “Product Management” started 25 years ago, so Charlene and I decided 2026 was the right time to take a longer than usual beat and think through what I (and we) wanted to do next.

The catalyst was personal in two ways:

• First, our two sons are launching into adult life, so family time is especially precious since they are home less often. Tim Urban’s blog post “The Tail End” is a good read on this topic. When a kid graduates from high school, about 93% of in-person time with a parent is over. At this stage, you’ve got about 7% left.

• Related, we wanted to experiment with inverting how our life was organized, focusing on the life part first and building work around that. For years I’d done the opposite. Let’s just say I was less successful fitting “everything else” in as well as I wanted.

We’ve taken the last few months to catch up on travel, spend more time outdoors, learn new skills, and see family and friends. (Still working on this last part, so let’s have coffee!)

Professionally, I’ve shifted into coaching and advisory work. Leaving a large leadership role to build something solo is equal parts exciting and humbling. Some days I’m energized. Some days I’m figuring it out as I go.

Why do it?

• I’d worked with executive coaches throughout my career. I found it helpful and, at times, transformational to how I thought about work. At the time, I noted this and filed it away as something that would be interesting to do later.

• As I’ve worked with increasingly larger teams, I found more of my time spent coaching leaders. Helping people improve and get where they wanted to go was often among the most fulfilling and alive parts of my job. Increasingly, I was also coaching people outside of my core work.

Subscribe now

A natural thought over time became: What if I focused here?

It all comes together in the work I’m doing now: helping senior product and R&D leaders through moments where what got them here stops working. That’s often a larger job scope, working to communicate better at new levels, leading hard transformations, or just a decision about what’s next.

This started with 1:1 exec coaching, and has recently expanded into advisory work with small startups. For my clients, I’m in the role of a trusted, neutral thought partner. For me, it’s being of service. That’s the throughline.

I’m in flight on coach training towards credentialing as an ICF-Certified Coach. It lets me blend a coaching mindset and skills with 25 years operating in product environments. As good as coaches I’ve had were, I always wished I could find one who had operated in environments like mine.

You can follow the latest here, or reach out to me directly. I’d love to hear from you, whether I can help you, someone you know, or to just catch up. If you’re in the Bay Area, let’s connect over coffee.

🧭 Free 30-minute coaching sessions: I’m opening a small number of free 30-minute coaching sessions this summer — for folks who’d like to sample coaching, or for whom price may be a barrier. If you’re working through a hard stretch or transition — a bigger role, a complex situation, or you just want a thinking partner for half an hour — just reply or visit me here. If someone you know could use this, feel free to share with them. I’d love to help.\

Share

1:1 exec coaching: I work with a small number of senior product leaders one-on-one as a coach. These are typically six-month engagements. If that’s you or someone you know, let’s talk.

⏱ Read time: 2 minutes

Do you ever miss noticing progress you’re making while it’s being made?

This has happened to me many times. It can feel like dissatisfaction with the present. I’m normally a notorious forward looker, and that means I’m usually working on something and somewhat dissatisfied about where I am on that journey. Maybe it’s low-grade perfectionism or a type-A achievement style focus.

So typically I’d react to a feeling like this by simply pushing harder, or reading something to try and get better, or by just, well, over-worrying about the whole thing.

To be fair, there are upsides to working this way that have paid off, but it’s not always the best habit for overall happiness, especially for people who care about you.

But I’ve been making a concerted effort to be more present for the journeys I’m on, and be less pressurized with myself about how fast I’m getting there. Closely related to this is being better at noticing progress being made that can sometimes hide if all you’re doing is pushing. No time to notice things.

This week I had a chance to meet up with 2 colleagues from a community I’m part of for a 15-min check-in call. The goal of the call is to try and meet up for 15 minutes every so often to check in with two simple prompts:

1. What’s a moment you’ve had that was better than imagined lately?

2. What are you taking with you until the next time we chat?

What came up for me this week was that my wife and I were in Seattle visiting our older son. I got some work done, met with a few coaching clients, and otherwise, experienced Seattle’s sunny summer days. This meant a bunch of time outdoors exploring, kayaking Lake Union, lots of good food, fabulous coffee and more.

With that context, this quick community check-in surfaced for me that this is what we intended when I shifted my work earlier this year.

The goal at the time was to set up life how we wanted it (more time to travel, visit our sons, and be outdoors) and then build work around that.

For years I did it the other way. Work first, life second.

So the win this week was noticing: more time in the sun felt like what we intended.

I still have lots of work in front of me and nothing is perfect. But the progress was — is — there.

So I celebrated the progress itself AND the fact that I’d noticed it. In past versions of myself, I might not have even noticed. The noticing itself helps me better realize it’s working.

What’s something you’re making progress on that you maybe haven’t noticed?

Here’s a shot of Lake Union from Queen Anne in Seattle this week.

1:1 exec coaching: I work with a small number of senior product leaders one-on-one as a coach. These are typically six-month engagements. If that’s you or someone you know, let’s talk.

⏱ Read time: 3 minutes

I’d just wrapped an 11 a.m. Headspace product review from my home office. I signed off the 17-person Zoom and walked into my kitchen to refill my coffee and process where I could have been better in that meeting. I wasn’t very happy either.

I’d done the thing I’d sometimes do. I’d asked a question in a group setting that was too long, and too complex. It didn’t really move the conversation forward. I was pretty bummed too. In that type of review setting, you don’t get those moments back.

When I think back to leading reviews and meetings, or even one-on-ones, I can see now how at times I’d missed asking better, more useful questions.

This year I’ve spent time in coaching training with a cohort working toward ICF certification. Many of these sessions include live demonstrations led by instructors who are skilled, 20-year coaching veterans. Often the training unfolds with a group of us with our video cameras off, watching someone in the class get coached by one of these expert coaches in real time.

I’ve seen people who have been struggling with a hard problem suddenly see things differently, with new ideas and attitudes. In class debriefs, our group notices how much progress can be made in just ten or fifteen minutes. Just by asking short, powerful questions and listening intentionally.

The learnings made me think back to questions I’d asked or seen asked that could have been better. So I wanted to share some of what I’d learned here. Getting a chance to watch skilled coaches work reminded me that one of the simplest ways to be a more effective leader and help a team is simply to ask shorter questions, and then listen closely.

Most teams tend to run on advice, and advice can be useful. Sometimes your teammate or direct report needs a direct answer or an informed recommendation that comes from your experience.

But advice by itself creates risk. When I give you advice, my context is not the same as your context. So, if you apply my answer as is to your situation, your result will likely be different.

A powerful question works differently. A good question invites the other person to do their own thinking with a useful cue. That can lead to an insight that’s more relevant to them and better connected to the reality they’re navigating. It may also spur creativity you might have otherwise missed.

Questions also allow for greater ownership vs advice alone. People are notoriously more likely to act on an insight they reached themselves vs one that is just stated with them in the room.

The good news is you don’t need coaching training to start using more powerful questions. The best ones tend to share three simple qualities you can try:

1. They are short. The fewer words you use, the better.

2. They are open. They invite a deeper answer versus either/or/yes/no.

3. They are followed by deep listening. This is different from listening while composing your next response in your head. It’s about paying close attention to the person’s answer. Plus, what does their face tell you? What’s the vibe in the room?

Here are four specific questions I’ve learned about and found interesting and useful:

What do you really want? A coach in my cohort called this one out: “The Spice Girls were onto something.” Most people have rarely been asked this question straight away. It can hit hard, in a good way.

What’s the conversation you’re avoiding? This one can surface the issue underneath the issue.

If you fully trusted your read, what would you do? This can help someone move past overthinking and just let it rip.

How are you complicit in creating the conditions you say you don’t want? This question comes from Jerry Colonna, and it may be my favorite. I’ve used this on myself. It hits me like a brick every time.

Try a small experiment this week.

Ask one of these questions, or answer one yourself. Then really listen for what’s being said. You’ll be surprised by what a good question, paired with real listening, can unlock.

Let me know how it goes.

1:1 exec coaching: I work with a small number of senior product leaders one-on-one as a coach. These are typically six-month engagements. If that’s you or someone you know, let’s talk.

⏱ Read time: 3 minutes

Have you ever been in a meeting at work and noticed what you might call “corporate speak?” I’m not immune. For example, I’ve caught myself front-loading too much context before getting to the point someone was after. In a world where AI-generated text is increasingly everywhere, anti-corporate speak, or saying what you mean, will stand out more than ever.

For me, corporate speak is when between 30-50% of a conversation is padding. This is language that’s not clearly saying what’s happening or what should happen. It’s often the result of someone’s fear of offending someone else in the room, or from a lack of the speaker’s clarity of thought.

When you do run across someone who consistently speaks directly, you realize how resonant that is compared to everyday corporate speak.

It’s like working underwater and looking out at the sky through that water vs. lifting your head out of the water and suddenly seeing the sky more clearly.

My favorite example of getting to this clarity is still from Ben Horowitz’s book, The Hard Thing About Hard Things. “Hard Things” is a fast read and is useful for anyone interested in learning about management, and more specifically, how tech companies work. The book was originally published in March, 2014 but is worth a revisit from time to time.

The most useful part of the book is infused throughout. It’s the drop-dead simple way Horowitz has of communicating. You get a sense for this in his take on specific stories. But you also see it in-between the stories in terms of how basic thoughts are conveyed: Use. As little. Words. As possible. Say exactly what you mean.

Take this example from the story about Horowitz trying to hire a VP of Sales into his struggling company. He has someone he thinks is fantastic in mind, but this person is a little odd. So board members plus Chairman and co-founder Mark Andreessen are taking issue. The potential hire doesn’t look exactly right. He went to a small school, and he has an off way about him. Horowitz listens and then makes a short, clear case:

“I agree with every single one of those issues. However, Mark Cranney is a sales savant. He has mastered sales to a level that far exceeds anybody that I have ever known. If he didn’t have the things wrong with him that you enumerated, he wouldn’t be willing to join a company that just traded at thirty-five cents per share; he’d be the CEO of IBM.”

Simple. Direct. This candidate has some issues, but he is exactly what we need right now and let’s get real, we are not exactly playing from a position of strength at this time.

Imagine instead how that statement could get mangled by someone who is either not clear about exactly what he (or she) thinks or not willing to just state it:

“Hmmmmm. You have some good points, there. Really. You do. This guy has some positive points, but we’re all agreed we need the best possible hire. I guess I need to take another look at this situation with that in mind and report back to the board in 30 days.”

That statement is a recipe for delay and then losing the candidate.

THAT, in the end, is the most valuable message of The Hard Thing About Hard Things. It’s a book about communicating with as little wasted language as possible.

Take the time to know what you think and then say EXACTLY that.

Doing so saves time and builds trust, both of which most startups are short on and desperately need.

This is even more important in 2026. In 2014, when this book came out, the enemy of clarity might have been fear or fuzziness of thought.

Both of those are still there. But now, AI can generate a thousand fluent, reasonable-sounding words in seconds. The result is more language than ever and less clarity than ever — vagueness with a clean coat of paint. AI can produce the words for you. It can’t know what you think, or make sure you say exactly that.

Try trimming your words this week. Before your next meeting, write the one sentence you’d say if you had only ten seconds. Say that first thing.

Let me know how it turns out.

👋 Hi, I’m Jeff. I coach senior product leaders through the moments their playbook stops working — drawing on 25+ years building at LinkedIn, Facebook, Headspace, and Included Health. If that’s you or someone you know, ping me.

This week I wanted to share something from the archive. When I was at Facebook leading a mid-sized team, a Business Lead at the time (equivalent to a Chief of Staff) asked me for hints or tips I could send her for what made effective PMs at Facebook. Below is what I sent her – along with a batch of links.

Reading this back years later, most of this still holds — and the one I’d underline now is communicating. Mainly because that’s what I often saw PMs struggle with. I also think these skills are extremely relevant and helpful as product development evolves given AI tools -- if anything these skills matter even more.

Give it a read -- and curious what pops for you.

///

Top 5 Facebook specific hints for PMs

• Impact -- coming from user empathy -- is key. Near, medium and long term. What are you spending time on — does it match where your impact is coming from? Do not focus on activity and think that that is impact. Try and nail the root user problem. What problems matter most to actual users?

• Communicate, Communicate, Communicate. Vision, talk in stories, write well, speak persuasively. Communicate what your team is doing at all times. What’s the one liner? Someone not getting it is not their fault.

• Vision is especially important at FB — because the company operates in 6 month planning cycles. So, create a narrative that spans across 6 month increments. Remember to show your team the progress vs that vision from time to time.

• Push with warmth — the best PMs have teams moving very fast and the team has no idea what they are doing is hard because the pushing feels like a normal pace being created by a warm, collaborative person. Create a cadence that feels normal but is actually faster than that.

• Build relationships. You want to be collaborative before you need someone. Help people.

Links I found helpful from outside Facebook

• Sense of urgency - Boz. (Bonus is if you can go see these wall clocks live. :-))

• LinkedIn Course on leading from Jeff Weiner - Bite size version of how Jeff ran LinkedIn. You can cherry pick areas -- but worth a watch end to end as well.

• The Future of LinkedIn | The Vision for the Next 10 Years. (Old LinkedIn preso at JP Morgan conference in 2014. Learning: Can you be this clear when you communicate? Also: rule of 3 in action.)

• How to Hire a Product Manager. Who: Ken Norton (Formerly Google, Jotspot, Yahoo!, then Google Ventures.)

• Strategic AND Tactical Who: Scott Gatz, (formerly Yahoo! — Now CEO/Founder, Q.Digital.)

• What distinguishes the top 1% of product managers from the top 10%? - Ian McAllister

• How to Spot the Five-Tool Superstar - Jeff Weiner

• So, what do product managers do? — Hunter Walk (Formerly YouTube, Google — Now Partner, Homebrew VC)

• ‘We Don’t Sell Saddles Here’ by Stewart Butterfield. Build something people want.

• How to resolve conflict at work in just five days (getting to alignment faster)

• ‘The Art of Being Compelling as a Product Manager’ by Sachin Rekhi

• Good Product Manager, Bad Product Manager - Ben Horowitz

• Be a Great Product Leader - Adam Nash

• The CEO as Chief Editor - Jack Dorsey

• The Silent Partner — Buzzfeed. About Jason Goldman — he helped build Google and Twitter — but few know his name.

1:1 Coaching: I coach senior leaders through the moments their playbook stops working — drawing on 25+ years building at LinkedIn, Facebook, Headspace, and Included Health. If that’s you or someone you know, ping me.

That coffee turned into a couple of introductions. I pointed him toward someone he should meet. He did the same for me. A few months later, he was deep in interviews for a large new role and working on some things he wanted to get better at. So we connected again. Today we’re working together—he’s one of my coaching clients. In January over a coffee, we were just catching up on life.

Since I left my company job last winter, I’ve been building an exec coaching practice while doing more catching up on life. So I now spend more time doing work with no immediate, obvious payoff: reading, reconnecting with people, writing. Just being a beginner again and learning.

In earlier career contexts, slower payoff work often felt necessary, but non-productive. Now, I’m viewing slower payoff “work” as an engine of growth and creativity. It helps generate luck, and it’s a new feedback loop for me.

The neurologist James Austin wrote about types of luck, including one you influence through your own activity. Later, the entrepreneur Jason Roberts framed the same idea as increasing your surface area for luck, viewing it as a formula:

Luck = Doing x Telling (i.e. building or trying something you’re interested in and then speaking about it with people)

Roberts’ formula is the sending half. What I’d add is the other half: some of it comes back — and whether you notice that is what closes the loop.

Here’s how it’s working for me: You send small emissaries—carriers of a message—out into the world, and some of them work their way back to you in interesting ways. This doesn’t happen linearly and is unpredictable, so sending more emissaries vs. fewer increases what comes back. What do emissaries look like?

When I look at what’s opened the most interesting doors for me so far this year, my emissaries usually take three shapes:

1. Something I create. A post, a note sent, a small thing I make and release into the world. (This post is an example). Ideas travel on their own timeline.

2. A new conversation I have. This is a coffee, reconnecting with someone, or just a question I ask a person I’m meeting. (The former-colleague now coaching-client example I shared)

3. A new place I go. My wife and I recently spent some time in Paris and Amsterdam, and we both fell for their coffee cultures. We’ve now turned into coffee nerds. Will this lead somewhere? No idea. The trip became a thread we’re still pulling.

For all three types, the magic is in the stretch, where the thing I do feels slightly hard as I do it. Like building something or being creative. That feels difficult at first. Or reaching out to a person I haven’t chatted with in a while, or maybe a place I’ve never been before. Something new.

The further outside my normal a new emissary idea travels, the more new ground it can touch. Exploring new things creates a different effect than the same people, same rooms, and same paths you’re used to. Same can be familiar and comfortable, but not as expansive. I’m learning a mix of both works best for me.

But sending out emissaries is only part one of the loop. The other half is noticing when something comes back. That’s closing the loop.

This can be non-obvious or take time. It’s like the butterfly effect. The wingbeat happens, but it’s not always easy to see a downstream effect. If you do notice it, it can change how you think. Seeing a completed loop encourages more experimentation. I see what’s possible and that it can work, so then I send more emissaries out.

So here’s an experiment for the week. Send out one or two emissaries that stretch you past your usual. Publish the draft you’ve been sitting on, reach out to the person you keep meaning to, walk into the room where you’re the newest one there. Then watch. Notice what comes back, even faintly.

You’re not waiting for luck. You’re sending for it.

👋 Hi, I’m Jeff. I coach senior product leaders through the moments their playbook stops working — drawing on 25+ years building at LinkedIn, Facebook, Headspace, and Included Health. If that’s you or someone you know, ping me.

If you made it this far, here’s a recent image from Juniper Cafe. Yum!

⏱ Read time: 5 minutes

I’ve been having a lot of conversations lately with people considering new opportunities: some job searching, some talking to recruiters, and some just thinking about what they want to do next.

The recurring question we end up talking through is: What’s the best way to think clearly about choosing your next opportunity?

People often start with things like company logo, employer brand, job title, company size or stage, vertical sector, or a specific hot category. (Hello, foundation model companies and AI-native companies.) I’ve considered these lenses too at different points in my career. They matter, but they mostly describe the external shape of an opportunity.

Sometimes there are real constraints: you need the job, compensation matters, family reality matters. I’ve been there.

But I’ve also found that I make better decisions when I start from the inside out — asking what it’ll feel like to do the work, with these people, at this point in my career, and how it might help me learn and grow.

This frame is personal, and meant as an idea starter, not a prescription. It’s just something that has worked well for me.

Here are the three questions I ask and think about:

1. The Product: Am I excited by what we’re building?

2. The Team: Do I want to build it with these people?

3. The Growth: Will this opportunity stretch me or help me grow?

Here’s how I think about each one.

1. The Product: Am I excited by what we’re building?

What are we building, and how interested am I in the idea of working on it every day?

The last thing I want is to work incredibly hard, look up, and realize: “Hey, this thing I’m building is actually not that interesting or meaningful to me.”

I’ve always wanted to feel fired up by the actual product, problem, or mission. How interested would I be day to day? Do I already use it? Would I use it? When I explain it to someone in my family, what’s their reaction? Do they understand why it matters? Would they use it?

As my kids got older, their reactions became an increasingly useful sanity check. It helped me see whether I was living in reality outside the normal tech bubble.

Headspace is a good example. Before I ever had a conversation about working there, I had used the product for years and benefited from it. So when I went through the interview process, I already knew the product from the inside out as a user. I’d seen different versions of it over time. I understood what it did well, where it had evolved, and why it mattered. That made the opportunity feel very real to me. It was something I was genuinely interested in being part of.

2. The Team: Do I want to build ‘the thing’ with these people?

Jeff Weiner has a people framework I’ve always liked: look for people who can dream big, get shit done, and know how to have fun. The best part of that advice is that you have to have all three.

When I’m considering an opportunity, I try to imagine what it would feel like to work with this group day to day on a hard problem. That includes the manager I’d be working with, the cross-functional partners, the people who might report to me, and the broader group around the work. What are they like? How do they think? How do they treat each other? Would I enjoy problem solving with them?

For me, fun shows up here. So does judgment. So do kindness, generosity, commitment, and the basic energy of the group. I’ve had the good fortune to work with outstanding teams at Yahoo, LinkedIn, and Facebook/Meta — people who were extremely talented, kind, committed, and generous. Years later, I’m still close with many of them.

When you work with someone multiple times, across multiple companies or chapters of your career, that usually tells you something. Those are the kinds of people I’m looking for when I evaluate any opportunity.

I do some research, of course. I pay attention during interviews. I listen for how people talk about the work, the team, and the problems they’re trying to solve.

But a lot of this also comes down to feel. Would hard work with these people feel energizing or draining?

3. The Growth: Will this opportunity stretch me or help me grow?

The best opportunities make me better in some meaningful way. That might mean bigger scope, role progression, learning a new domain, helping solve a transformation problem at a company, building a new skill or muscle, or financial upside. But this question also evolves depending on the season of a career.

Sometimes the stretch is about taking on a larger role. Sometimes it is about learning a whole new industry. That happened for me when I joined Headspace and Included Health after years working on information and media products, social, and video experiences. Healthcare was different: complex and new to me in ways that made both opportunities interesting.

Sometimes it can be about joining a company or team that needs to go through a transformation, and asking whether I can help a team make progress there, fix things and improve. Both Headspace and Included Health also fit this lens for me. They were different than working at large internet companies, where operations, give or take, are working pretty well.

Compensation and equity matter for sure. I think about those things and get advice on them when considering new roles. Public company equity, pre-IPO equity, salary, and financial upside are all real inputs. I don’t discount those.

But for me, they usually sit inside the broader question: Will this opportunity help me learn, grow, contribute, and become better than I was before?

Use these as a practical gut check, not a rigid decision matrix.

If you’re looking at opportunities — or even just thinking through what you want to do next — they can help you double check what you’re optimizing for.

The TL;DR: Don’t just ask how the opportunity looks from the outside. Ask what it will ask of you, who you’ll be around, and whether it will help you grow.

As you’re thinking things through, try to answer the three questions honestly. The weakest answer may tell you where to look harder.

👋 Hi, I’m Jeff. I coach senior product leaders through the moments their playbook stops working — drawing on 25+ years building at LinkedIn, Facebook, Headspace, and Included Health. If that’s you or someone you know, ping me.

👋 Hi, I’m Jeff. I coach senior product leaders through the moments their playbook stops working — drawing on 25+ years building at LinkedIn, Facebook, Headspace, and Included Health. If that’s you or someone you know, ping me.

⏱ Read time: 3 minutes

There was a time when Charlene and I loved getting an early evening cocktail at La Bodeguita del Medio, a local Cuban restaurant in Palo Alto.

The bar was friendly and fun, full of conversation and great snacks. Every so often, we’d show up, get comfortable, and have that first sip—always a Cuban sidecar in those days. For a second, all things felt possible.

Sometimes it was just the two of us, sometimes we’d chat at the bar with others.

Either way, the conversation was good. My favorite part usually came somewhere between the end of cocktail one and the beginning of cocktail two. The room got a little freer. Everyone worried less about how they sounded and edited themselves a little less. In the right company, people would start saying more of what they actually thought… about anything. (A few empanadas or bacon-wrapped dates also helped.)

There is something magical about that kind of moment. Not careless. Just more honest.

Not long ago, I was in a Zoom conversation with someone feeling stress due to increased scope in her role. We looked at her priority list together; it had 11 items on it. I’ve been there myself.

A list like that can almost always be defended. Each item is important in some way. But that list is usually the source of the stress—and the reason there’s no room to think.

Lists like these fragment attention. More importantly, they crowd out more spacious, creative thinking, where the biggest gains live.

Over time, I started thinking about priority lists through what I call the cocktail test. Here is how it works:

• Imagine it is 2028. Imagine you’re having a drink—mocktail or cocktail, you decide.

• You are sitting across from a friend or loved one who really knows you. The conversation has reached that magical, more honest place.

• They ask you: “Looking back, what were the three things that mattered most?” (In whatever context–company or life.)

My bet is that your answer comes pretty quickly. And my much stronger bet is that your answer is not about eleven things. It’s two or three bigger, chunkier things. The things that changed the trajectory of a project, team, or company.

Also see:

• Flash Feedback: The 45-Day Check-In That Changes Everything - A faster, simpler way to give new hires feedback that actually matters.

The cocktail test works because it’s easy to imagine, it creates distance from the day-to-day, and it helps you see this all more clearly. For me, it’s a quick, easy (fun!) exercise that compresses signal from noise faster than any planning framework I’ve used.

Molly Graham, who ran operations at early Facebook, wrote: “If you have 6 or 8 or 10 company goals, here’s the truth: you actually have 3 goals. You were just too scared to kill some of them.”

A long priority list can feel thorough and responsible. But the goal is not a more organized planning doc or list. The goal is to create more space for expansive, creative thinking that changes the trajectory of a company or life.

Without that space, you can become more efficient. You can get more done. But you may also just be running faster on a treadmill headed nowhere in particular.

You can try the cocktail test any time. Sometime this week, give yourself a little distance from your inbox, your calendar, and the list.

Grab your cocktail or mocktail of choice. Picture yourself in 2028, sitting across from a friend who really knows you. The conversation has reached that more honest place. They ask the magic question: “Looking back, what were the three things that mattered most?”

Imagine forward and then write down the answer.

Then hold those three things next to your current priority list. The gap is the point. If you feel bad about the gap, there’s good news. You’re at least in the middle of a nice cocktail.

👋 Hi, I’m Jeff. I write weekly about lessons I’ve learned leading product teams and working to lead well in chaotic environments, drawing on 25+ years of building.

1:1 exec coaching: I’m working with a small number of senior leaders one-on-one as a coach. These are typically six-month engagements. If that’s you or someone you know, ping me.

⏱ Read time: 3 minutes

In 1996, I was 25 and producing a story in Sacramento for a PBS television documentary called Easy Money. It was an investigation into the gambling industry’s political power. My job was to set up interviews, produce video shoots with a crew, and keep the production running—aka make television happen.

One of those interviews was a follow-up with California’s then-Attorney General Dan Lungren. I’d booked it at his 20th-floor office in the California Department of Justice building in Sacramento. A television crew and I pulled up midweek: a camera operator, sound technician, production assistant, our director, me, and a minivan full of production gear.

We started setting up. Within minutes, a disagreement broke out between our director and the AG’s staff over where the interview would happen. Our director wanted to film in the AG’s office for visual contrast with an earlier interview at a different location. The AG’s staff wanted to use the conference room, as the AG would be more comfortable there. Neither side budged. Things escalated fast and it got loud.

Two grown men yelling at each other, one of them a state government official. Half of me couldn’t believe the absurdity of it. The other half of me was trying to step in. Underneath all of it, my stress was building. I’d organized this shoot. If it fell apart, was that on me? Was I about to lose my job? I’d seen it happen while working in television: “Hey, pack your stuff up in a box.”

When voices are raised inside the Department of Justice building, a security detail shows up. Quickly. They were crisp, curt, and unrattled, informing us we’d be leaving. Now. Then they walked our entire crew out of the office to the elevator and rode down the 20 floors while standing behind us.

As the elevator descended, I glanced back over my shoulder at the detail. They wore earpieces. Under their blue sport coats, large guns.

Also see:

• How to Onboard into a New Leadership Role: 7 Lessons from 25 Years - Gathering context is only the beginning. Here’s the playbook I’ve kept evolving.

Back on the first floor, we packed up our gear at the curb. Our director sped off, furious we hadn’t gotten the interview. I drove home to a small Bay Area apartment where my wife, Charlene, was returning from her work day, waiting to hear about the shoot in Sacramento.

I spent that two-hour drive home, and the rest of the night, playing the day back. The yelling, the confusion, the stress, the dread of walking into the office the next morning. I told Charlene, “I’m hoping I don’t get fired tomorrow.”

---

I’ve been telling teams a shorter version of this story ever since. I’d usually end with: “Team, let’s be honest. Nobody’s escorting us out of here with guns today.”

The rooms have changed since then. No more documentary crews. No government buildings. More whiteboards, longer meetings, Zoom calls. Product launches. New problems to solve.

But stressful work moments still show up and feel heavy. My body and mind still react. Like the launch at Included Health that slipped a date because we missed a detail in how a clinical tool should have worked. Or the email thread trying to explain a subscription-metric change to LinkedIn’s leadership the day of a business review.

That day with the AG’s security detail turned out to be a gift to a later version of me.

No matter what problem a team and I were facing, I knew I’d lived through 30 minutes worse than that. Once you’ve lived through your worst 30 minutes, every other hard thing feels easier.

That’s the gift. Not the stress. A lived perspective on how bad bad is.

---

This week, when you’re in a meeting that feels high-stakes, pause and ask: “Is this worse than my worst day?” Most of the time, it’s not.

What’s a moment that became your stress ceiling?