A few years ago, I was leading a busy, under-pressure product org. I knew I needed more dedicated focus time but my Google calendar looked like a stacked game of Tetris. One meeting stood out on the list of things to cut to get more space. A bi-weekly organizational meeting scheduled by my own manager.
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.
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.
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.
