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.

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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.

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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.

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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.\

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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?

👋 Hi, I’m Jeff. I’m back from some traveling (maybe in another post). 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 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: 6 minutes

In December 2017, I transitioned from LinkedIn to lead a small product team at Facebook building for creators. It started with the standard, not-great onboarding you’d expect.

But there was an unexpected gift of onboarding in December: this frenetic company slowed down. For a couple of weeks, Building 20 in Menlo Park was unusually quiet and mostly empty. I remember some Facebook employees walking their visiting families around the office, showing off the campus. They’d walk right by my desk.

Given the quiet, I used the time to start gathering context and, more importantly, think about what I’d learned from past onboards. I built a short playbook of notes for myself in those two weeks that I’ve kept evolving ever since.

Onboarding well is more than gathering context quickly. It’s forming points of view fast enough to shape what should come next. AI is making it easier and faster to understand context in a new role. But forming your point of view, connecting dots, deciding what needs help, choosing where to push and how — is still your most valuable human work. If you’re a VP, this shows up in how quickly you define strategy or assess a team. If you’re an IC, it shows up in how you frame problems and earn trust early.

Across internal moves, large companies, and startups, I’ve done onboarding well and also made mistakes. When I look back, the biggest mistake is almost always the same: I should have moved faster. And that’s even after times I’d moved fast.

Here are seven onboarding themes I use:

1. Treat the organization like a product. Most leaders go deep on the product early on, but make sure to spend time on the product that produces that product. That’s the team. Like any product, a team has inputs, ways it works, and outputs. It has users, problems to solve, and jobs to be done. Thinking about teams this way creates a lens for new ideas. Some of the most meaningful work I’ve done in new roles was about product managing the org itself: understanding how it worked before I arrived, where it was getting stuck, and how it needed to work differently to get better.

2. Protect your beginner’s mind. Avoid the lobster scenario: the water is heating up slowly, and before you realize it, you’re captive and adapting to the very culture you were hired to help evolve or change. Extend how long you think like a new person. Fresh eyes are valuable. Lean into your early lack of context as a source of interesting insight and unencumbered questions. Ask “why do we do it this way?” too often. New observations happen early. Notice them, write them down, and use them. One exec I worked with at Facebook kept a category of observations called “Huh?”

3. Seek patterns: Use structured listening and try the ‘doc test.’ Move through the org one 1:1 at a time, asking everyone the same questions: what’s going well, what’s not going well, where can I help, and what would you focus on if you were me.

AI tools with ambient transcription can help compare all these notes for you. You’re building trust by listening, and the team is pointing you at the context that matters most. Disagreement in what you hear is itself a signal. It means people aren’t aligned.

Pair this with the doc test, a useful question to ask even when AI can help find the answer for you. Ask different people to share the single doc on an important topic. You’ll get one of three signals:

• Everyone sends the same doc. Good sign.

• No doc exists. A flag.

• You get five different docs. An opportunity to create clarity.

4. Start bigger changes sooner than feels comfortable. Have a clear point of view on what type of org you’re joining and then act sooner than feels comfortable. A rocket ship wants you to keep things going, enhance and improve. A transformation wants you to help them change. There’s a continuum here, but don’t use a posture built for one scenario when you’re living in another.

Start bigger changes sooner than conventional wisdom says. Standard onboarding advice is to seek quick wins, avoid changing too much too soon, and think in terms of a 90-day or even one-year horizon. I’ve learned to go faster. The biggest changes that generate real impact: strategy, talent, growth, or how an org operates, all need time to unfold. The sooner you start, the quicker you see impact. Deep listening (see #3) is what lets you move sooner with more confidence. A clear point of view can arrive faster than you expect. As it does, lean into it.

Also see:

• Answer First: A Simple Framework for Executive Communication

  People often ask me how to communicate more clearly with senior leaders. Some quick thoughts...

5. Make your thinking visible. As Jeff Weiner has said at LinkedIn, citing David Gergen: Effective communication is repeating your message more times than feels natural. Writing helps. Write and share your observations early, and more often than feels comfortable. Sharing your writing in Slack, docs, or email will help you scale beyond the rooms you are physically in. I’ve seen this work well for individual contributors as well as leaders. One mistake I’ve made is writing less in cultures where writing isn’t the norm. Lesson: write anyway. Treat internal communication like a political campaign. Repeat your core message far more than you think.

6. Uncomfortable truths. Be prepared to state them. In my experience, there is a near linear correlation between your directness (from a place of deep listening and care) and building trust and creating success. You may learn early on that a person, process, or leadership pattern is part of what needs to change. Don’t shy away from articulating what you see and learn. Be kind, but clear. Your new point of view is part of why you are there.

7. Set boundaries: Go as you intend to travel. Whatever boundaries you need to be effective, set them from day one. At times, I’ve let myself react to how a company or team behaves, and later regretted not being clearer about time, weekends, and operating expectations sooner. Don’t confuse activity with progress or fall into meeting creep because you’re new. Some of the most effective people I’ve worked with — often working moms — state what they need clearly and work backwards from there. Be uncomfortably clear here. It will pay off.

If I were onboarding into a new role today, I’d do all seven of these sooner and more boldly. The biggest mistake I’ve made is not moving faster. AI is making context-gathering more efficient than ever. But you still need to listen deeply, form a point of view, decide what needs help, and say the uncomfortable thing.

If you’re onboarding soon, the doc test is a simple place to start. Pick one topic that matters. Ask three different people for the single doc on it. The pattern in the replies will tell you more than the docs.

Work the rest as you go.

👋 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 product leaders one-on-one as a coach. If that’s you or someone you know, ping me.

⏱ Read time: 2 minutes

I’m writing from Paris, where I’ll be until the end of the month with equal parts work, relaxation, and exploring. Two things I’ve been noticing.

———

First, coffee culture and how digital shows up. We’ve been exploring coffee and café culture on the road.

We’re noticing two distinct modes:

1: Coffee shops or cafés with a single giant community table in the back and lots of people with laptops and small teams working in small groups or even dialing into conference calls. All over coffee. It’s almost like a coffee shop as WeWork model. This scenario is mostly Amsterdam.

2: Coffee shops or cafés with explicit “no laptops” signs on any flat surface. Everyone is reading a book or, gasp, talking. We’ve noticed this mostly in Paris or Amsterdam where the coffee is especially high end.

It’s worth watching how everyday people here treat their “third place.” Charlene wrote about this if you’d like to go deeper.

Either way, the coffee has been excellent.

———

Second, train rides and long coffees mean lots of time to read. I came across this New York Times article by a reporter who covers white-collar work. Two themes stood out.

1. AI compresses execution, not decision-making. Tasks like coding, writing decks, and drafting strategy are getting done faster or automated entirely. But decisions, alignment, and prioritization still require humans. As execution gets easier, the hard human work—judgment, empathy, alignment—will rise in value.

2. Social skills are becoming a real moat. Persuasion, storytelling, relationship-building, and trust matter more as the barrier to getting work done drops. Winners may be generalists who can influence, lead, and tell stories. Building is getting easier. Direction and narrative are the differentiators.

As I experiment with tools and automation, I keep coming back to the human conversations. The tools are helping me do things faster, better, but I still need to be good at dealing with people. Not only is it not going away. It’s becoming even more of the whole game.

What are you seeing?

👋 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 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

Hi there, I’m writing this note on a train to Paris for some city exploring my wife and I have been looking forward to. A three-hour train ride is also a creative place to write.

Clear, early feedback is one of the most valuable gifts a leader can give someone. The earlier this happens in a working relationship, the better. It sets a standard, establishes tone, and clarifies expectations. Most leaders wait too long to do this, and that can create downstream issues that are harder to fix.

Most performance review templates overdo rubrics, create unneeded complexity, and happen too late to matter. So I built a simpler approach. I call it Flash Feedback.

The Setup

Whenever I start a new role or I hire a new person, I tell my new report: we’ll do a flash feedback round 45–60 days in. Sometimes I mention this pre-hiring too, which communicates how seriously I take helping them succeed.

I ask them for six to eight names of colleagues they work closely with. These are the people I’ll email on their behalf to solicit feedback. I review the list of names and make some suggestions if needed. I go out of my way to make it feel safe to include someone where there may have been an early challenge or tough working relationship. (This is often the most valuable feedback to get.)

How It Works

I email everyone at once, BCC’d, and ask 3 questions:

1. What is Person X doing that is most useful and impactful?

2. What is Person X doing or missing that you think detracts from their ability to create impact?

3. What is your magic advice to Person X to help them be even better and more impactful in their role?

I ask them to reply directly to me, copy the 3 questions above, set a timer for 10 minutes and just write. The goal is bluntness instead of massaging the feedback.

I chase everyone down in email until I have all of the feedback. If necessary, I ask follow-up questions. (Sometimes I even follow up by phone.)

Next, I write up a two-page summary organized as follows:

• TLDR: Overarching themes from the feedback and my own observations

• Areas of strength (mapped to question 1): Themes and my own observations

• Areas to consider for development (mapped to question 2): Themes and my own observations

• Advice to create more impact (mapped to question 3): Themes and my own observations

The Part Most Leaders Skip

As I summarize key themes, I illustrate each with a few short quotes from the raw feedback. The real value here is your ability to curate and summarize what’s most important. It’s not simply transcribing exactly what you get.

Many managers and leaders skip this step or don’t do it well. For example, many times, teams themselves need to change and improve. That means you may get feedback that is valuable, but you may also get feedback that reflects an underperforming team being stretched by a new person. Your value is knowing the difference, and prioritizing where to focus. Your job is to construct a picture of reality that is helpful and moves the employee forward.

Once I’ve completed Flash Feedback, I send the document in advance and schedule 60 minutes to review it together. We dig into details and questions they may have, like where they should focus their attention first and in the coming months.

If you do even this, you’ll have given something many employees rarely get: early, clear, actionable feedback before patterns lock.

Most of all, you’ll have stepped outside the company voice and offered your own perspective. That’s the difference between being a manager and being a coach.

A rare gift indeed.

I’d love to hear how you approach early feedback — or whether you try this. Just hit reply, I read every one.

I’m now doing 1:1 coaching. Ping me if you know someone who’d benefit.

⏱ Read time: 3 minutes

In recent reading and in conversations I’ve been having, I’m noticing two contrasting lines of thought on AI and the evolution of work. The tension between the two feels important.

First is a “speed up” wave of thought and action.

As teams evolve and workflows change with more usage of new AI tools, we’re in the early days of product development roles beginning to blend together. Rather than independent titles, each of these might eventually be called “creatives” or “builders” — and be far more T-shaped in how they work.

People may come from a specific discipline background but end up working more flexibly. Think of it like a jazz band. You know your instrument, but what you’re really doing is playing jazz: following, leading, and playing in different keys depending on what the song or the band needs. AI tools are accelerating this shift fast.

Most people I speak with are rightly pushing to quickly learn AI tools. I’m personally playing with Claude Code, Codex, and Replit in my day-to-day work. I’m often looking for genuine automation or acceleration for real work I am doing, or I’m experimenting to see what’s possible.

For me, playing at the forward edge (not bleeding edge) feels sufficient, even focused. Fully keeping up with every new change may be counterproductive given how fast AI is moving. I’m trying to walk a somewhat simpler, slower path. It’s working for now.

Even with a push to speed up learning, there’s a competing pull to slow down and make sure your work carries the soul of who you are — a differentiated person with something unique to offer. This is about being smart about what cognitive processes are okay to outsource while keeping your mental knives sharp.

You use a dishwasher on everyday dishes, but you always handwash kitchen knives. If you dishwash a chef’s knife, you dull the blade. Everybody needs to know what their “knife” is. If you fully outsource your work to AI you lose your mental edge — the deep thinking behind the work. It will be hard to get that back.

How each of us balances the push to speed up and slow down will determine how well we create, whether it’s a product, service, company, or art.

One clear example is writing. You can outsource research and tactical editing, but it’s worthwhile to have your true voice show up in the final version. That means continuing to struggle with editing cycles, working through revisions with humans, and protecting voice and tone. It’s about speeding up less critical commodity work, but slowing down to protect and sharpen what’s irreplaceable and comes alive most like you.

The winning hands as we evolve will come from those who work the right edges between speed and slowness. Most people will pick a side: speeding up or slowing down. But the winners will be the ones who do the harder thing and hold both.

What do you think?

👋 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.

I re-launched a new website, focusing on coaching I’m doing.

⏱ Read time: 3 minutes

It was usually about 7:30 am.

Before anyone else arrived at the office, I’d slip into the only conference room we had, open the Headspace app, and sit quietly for a few minutes. At the time, I was finishing a seven-year tour of duty at a small, 20-person startup in Silicon Valley.

Why try meditation? I was hunting for edges — better systems, better strategy, better performance. Meditation felt like one more experiment worth running.

But that same drive to improve had a cost.

Back then, I put too much pressure on myself – ruminating, taking everything too seriously. Our sons were young. I thought having kids might slow the overthinking. Instead — more people depending on me, more to lose.

The overthinking pulled me out of rooms. At times I’d be less present, less patient, and less thoughtful — with the people I cared about most.

But my morning conference room experiment was causing something to shift.

That didn’t mean the habit was easy. It’s never a fully consistent practice for me. I manage a few times a week when things are going well, but rarely every day. I often have to start over. That’s still true today.

I’ll skip the science on mindfulness. Here’s what I noticed:

I started watching myself from a slight distance, noticing how I was showing up.

I could catch my mind wandering mid-dinner, mid-conversation—and bring it back.

My stress fuse got longer. I’d notice the buildup and pause before reacting…or not reacting at all.

But the shift I didn’t see coming was what others noticed. My wife would occasionally ask, “Hey, how’s your meditation going?” That landed two ways for me: this must be working…maybe I hadn’t always been easy to be around.

The experiment was changing me. That person happened to perform better at work too.

But what I valued more was becoming calmer: a better parent, husband, friend, son.

The highest-leverage work isn’t optimizing your tactics — it’s becoming a different person. What changed wasn’t my strategy. It was me.

If you want to feel what that shift is like, start here. A simple practice I learned from a coach: Notice three things around you right now. Research shows that’s enough to interrupt your autopilot. Thirty seconds. Most people are surprised by what they notice.

What were you optimizing for — and what actually changed?

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👋 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.

⏱ Read time: 5 minutes

Years ago, I was in a keynote speaker training session at LinkedIn with six other leaders. This course was for a group of us preparing to speak on large company stages. The instructor mentioned he had worked with Sheryl Sandberg, and then shared something she’d told him that stuck with me.

He told us that she’d said preparing for any single keynote was simply a matter of time and effort. You can always grind through it with raw effort. But what’s more valuable is honing how you prepare for more regular public speaking. You can’t always spend unlimited time preparing.

That reframe shifts the goal from surviving one talk to building a lightweight system you can use in any context, from keynotes to smaller stages or important meetings.

I ended up experiencing speaker training at both LinkedIn and Facebook, and I’ve spoken in front of large audiences enough where I’ve learned what works for me. Here are a few tips that can apply to keynotes and all-hands meetings, but also to any setting where you need to deliver a clear message.

Some overarching advice: Spend time preparing your presence at least as much as your content.

1. Open with a specific energy, not just words.

Content fills the slides; presence fills the room. Those first 60 seconds of any talk set the tone for the room and you. The most common audience response is to tune out, lean forward, or laugh. You want one of those last two. The energy you bring to the stage in those first seconds is how you’ll feel for the next 20 minutes. You can create humor, a relaxed vibe—whatever you want. But make it intentional because that vibe carries the whole session.

I’ve found it helpful before giving a keynote to watch the opening 60 seconds of skilled speakers you enjoy on YouTube. Not to copy them, but to calibrate energy. Michelle Obama is helpful for me – she’s excellent at the first 60 seconds because she brings the room in effortlessly.

I’ve also gone back and watched old Mike Gamson talks at LinkedIn. Find what works for you.

2. Start somewhere unexpected.

Once you’ve locked the energy you’re bringing in, you build the content. Many speakers default to what feels safe. Audiences are more forgiving and more responsive to the unusual, so push past safe. You have more license than you think. Take advantage.

I’ve opened talks with jokes or questions. I’ve asked audiences to stand up and stretch or say hello to each other. I once led a large room through a short Headspace meditation. The room always loosens, and more importantly, so do I. Humor, physicality, interactivity all work as openers. Be a little different.

3. Find a human story.

Messages land stronger when attached to a story. Arguments anchored in a scene become more memorable. Whether you share customer stories, team tales, or something from the past, find a way to connect your talk to something human that will stick for your audience.

4. Rule of Three.

Some speakers get in front of large audiences and build narratives that feel exhaustive. The speaker’s real worry is leaving something out. But when you string too many ideas together, audiences in a large room can’t ingest or remember what comes across as competing concepts.

The best talks are built on three messages. Think A, then B, then C, and connect them. To the human brain, one is a fact, two is a contrast, three is a rhythm. The brain remembers rhythm.

Three simple ideas hit the sweet spot between too little and too much for working memory. If you add a fourth idea, audiences remember less than if you’d stopped at three.

5. Repeat, repeat, repeat.

Repeat your A, B, and C. Tell people up front what the three things are. Remind them where you are in the context of the three. Summarize the three messages at the end. This gives your talk a feeling of simplicity and inevitability.

Remember, the second messenger matters more than the first. The powerful moment is when someone in that room repeats your three points to someone else later. That’s the start of verbal virality.

6. Use your body. Slow down.

A common missed opportunity I see is speakers flying through their key points. Think through how you move on stage: how you use your hands, the way you walk, when you start and stop motion, your pacing. Physical storytelling and pace are underrated.

Slow down where it matters. Pauses feel three times longer to you than they do to your audience. Go ahead and take the pause.

7. Think and practice in blocks, not scripts.

Organize talks as a small group of building blocks. Think of it as discrete sections that each have their own logic rather than a linear script.

Linear scripts are fragile. When one thing goes differently than planned, a whole talk can unravel or change your confidence. Blocks are more flexible. You can react to live moments on stage or adjust timing because you’re just playing with blocks. To the audience, it feels like it’s all working.

Once you have your blocks, rehearse the transitions between them. Talks can lose momentum moving from idea to new idea. The transitions need to feel seamless. Try each a few times until the blocks string together simply.

8. Make your practice feel real.

If you’re going to give the talk standing, practice standing. If you’ll be using a clicker, wire one up to your laptop to try beforehand. Don’t rehearse sitting at a desk, or worse, in your mind, and expect your body to show up differently on stage. The goal is to make the real thing feel like a talk you’ve already done well a few times.

9. Settle your mind.

After all the prep, I often use a short 3-5 minute guided meditation—usually from the Headspace app—sometime on the day of the talk. It helps settle my breathing, clear my head, and let the preparation do its work from a state of flow rather than memorization.

That was Sheryl Sandberg’s point: don’t prepare for a talk. Build a system.

Most speakers prepare their content. Few prepare their presence. The gap between a talk that lands and one that doesn’t lives right there. Not in the slides.

What do you do before a big talk that most people wouldn’t expect?

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

People often ask me how to communicate more clearly with senior leaders. Some quick thoughts:

My learning on this topic came when I was in a Group Product Manager role at LinkedIn. I once answered a CEO’s direct question in a meeting for 2-3 minutes before realizing (I had some help on this) that I hadn’t actually answered it. No bueno.

It was a weekly leadership meeting with Jeff Weiner, LinkedIn’s CEO at the time. Each product group shared a quick weekly update. I had recently landed this role and was leading Sales Navigator — a ~$250M product line growing quickly. It was one of my first few times in that room. On this day I covered my part partnering with my sales counterpart. So far so good.

But then Jeff asked me a direct follow-up question. I knew the answer and it wasn’t great news. I defaulted to pre-describing lots of context that eventually led to the information he was looking for. All good stuff except I took too long to get to the point.

Jeff was visibly impatient—and it showed. We moved on. I didn’t feel great.

Here’s what made the difference. A few minutes after the meeting, several teammates in the room separately texted and called me to kindly and directly give me advice to better handle questions in that room.

TLDR: “Get to the answer first. Then offer relevant supporting info IF NEEDED. Got it?”

Got it.

One teammate later sent me a link to Barbara Minto’s Pyramid Principle, a consulting version of the same idea.

I’ve since adopted my own simpler version, which I’ve shared with people across a few companies. I usually get stares, as if it can’t be that simple. It is.

Here’s the 3-Step Framework:

Step 0. Adopt a simple rule: Answer first. Always. I’m cheating with Step 0; it’s a hint more than a step. Here’s what that looks like in practice:

Step 1: Give one sentence of context. Enough to frame what’s coming next. No more. It will sound insufficient. It just works in these settings.

Step 2: Give the answer. Start with the conclusion. Then stop talking. Make the answer yours. Own it, and share it with conviction. Conviction builds confidence, even when people disagree. Talking too much erodes that confidence.

Step 3: Be prepared to support your Step 2 POV with up to three reasons. Not four. Not five. Three. That’s it.

Bonus points if your support reasons each come with a nugget of portable data simple enough that the room will repeat that data in some other room they go into later. Example? If you hear other people re-stating a data nugget you used to support a simple answer, that means your thinking is breaking through.

Why does this work?

First, the higher someone goes in an organization, the less patience there is for warm-up, throat clearing or any kind of non-essential communication.

Most leaders are managing 100+ emails, 50+ Slack threads, back-to-back meetings, and competing priorities. Almost anything they read or hear is usually delivered with 35–50% more words than needed. People are drowning in communication. Much of it is overthought. Sharper and simpler is rare and breaks through.

Your job isn’t to narrate your thinking process. Your job is to reduce cognitive load. Cut through the noise.

Make what you say land simply. Think like a political candidate. “It’s the economy, stupid.” Try for something that simple.

Try it this week. If someone asks you a question, give one sentence of context and then the answer. Then pause. If they want more, they’ll ask.

What’s a communication habit you had to unlearn?