Strategy Is Mostly Waiting
On finished products, founder instincts, and the discipline of not shipping
We had sold the company to NetSuite1 two years earlier, and I’d spent most of that time building a new business unit from the inside. A mid-market HR product, designed from scratch, aligned with early design partners from the existing customer base, and built by a team that believed in what we were making.
The MVP was strong and usable. A modern, beautiful, employee-centric experience, tied into core finance data. We had customers who wanted it.
And I was being told we couldn’t show it to them.
The colourful walls, fancy lighting, and massage chairs in our newly finished office felt like consolation prizes.
The decision wasn’t mine. I reported to the founder, who was also the Chair and the CTO, and the logic was sound even if it was hard to swallow. Going public too early would tip our hand to a competitor and undermine the positioning we’d been using in live deals. We didn’t need a beta. We needed a complete v1, full feature parity, before a single customer could touch it.
Which meant I had to walk into a room and tell a team that had been building for two years that they’d need to wait at least another year. Not because the product wasn’t good enough. Because the timing wasn’t ours to choose.
The colourful walls, fancy lighting, and massage chairs in our newly finished office felt like consolation prizes.
After years as a founder, I had absorbed a set of instincts that all pointed the same way. Ship early. Test fast. Get signal. Learn. These instincts are usually right. They’re what got you here. They reward movement, and they punish hesitation.
Strategy asks you to override all of them. Not with better information, but with a bet on timing that might not resolve for months. Maybe longer.
That’s the part no one warns you about.
Every week the product sat idle, the pull to move got louder. Ship it. Run a beta. Launch a quiet campaign. Do something. The instinct wasn’t wrong, exactly. It was just pointed at the wrong problem. We didn’t need more data. We needed the data to arrive at the right moment.
I know what happens when that discomfort wins, because I’ve given in to it. The thrashing. You start issuing rapid-fire instructions: speed up the campaign, push the feature out, run an experiment. Anything to feel like you’re generating signal. I’ve watched other founder CEOs do the same thing, and I recognize it immediately because I learned the pattern from the inside.
It feels like decisiveness. It looks like momentum. But it isn’t. More activity doesn’t speed up the signal; it just adds noise. The team gets pulled in three directions, the data gets muddier, and the original strategic bet, the one that needed stillness, gets harder to read, not easier.
The hardest thing wasn’t holding the product back. It was holding *myself* back.
~
Here’s what took me a long time to understand about strategic thinking: the feedback loops are brutally long.
When you ship a feature, you find out in weeks whether it works. When you run a marketing experiment, you get signal in days. When you hire someone, you know within a few months if it was the right call.
Strategy doesn’t work like that. A positioning decision might take a year to prove itself. A market timing call might take two. And some strategic bets never fully resolve. You just move forward and eventually stop asking whether it was right.
This makes strategy very difficult to evaluate while it’s happening. You can’t A/B test a competitive positioning decision. You can’t run a sprint retro on a market entry. You sit with the uncertainty and you wait.
For someone wired to ship and iterate, this is genuinely uncomfortable. It’s like being asked to hold your breath without being told when you can stop.
That discomfort stuck with me long after that particular product eventually launched. I started noticing how much of strategic thinking lives in that uncomfortable gap between making a bet and finding out if it was right.
And I started looking for ways to tighten the loop. Not to eliminate the waiting, but to make the reasoning sharper while you’re in it. Things like treating strategic thinking and decision making as a teachable competency instead of an instinct. Being more deliberate about how strategy gets communicated and pressure-tested inside a company. Finding ways to make the logic visible even when the results aren’t.
None of that makes strategy fast. But it makes the waiting more honest.
~
I still think about that meeting sometimes. The product sitting there, finished. The team ready. The roadmap paused.
The bet paid off, as it happens.2 But I didn’t know any of that at the time. At the time it felt like stalling. Like I was failing the most basic founder test: the willingness to move.
Now it looks like what it was: strategy in its least glamorous form. The quiet, tedious, ungratifying work of not doing the thing you know how to do, because the timing isn’t yours to choose.
Sometimes the hardest strategic decision is the one where you don’t move. And sometimes you never get to find out for certain whether it was right.
You just hold still, and trust the bet.
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P.S. A Note on Practice
I kept the launch details light in the essay, so here’s the rest.
We only got the product into customers’ hands a couple of months before the public announcement. The launch was big - $7M in bookings in the first six months. But the thing I keep coming back to is that getting it into hands earlier wouldn’t have changed those numbers. The features were the same either way. What it would have done is give a competitor eighteen months of advance warning and probably cost us deals we were winning in the meantime. So the patience wasn’t really about the launch. It was about protecting everything else.
I struggled to believe that at the time. It’s easier to be forgiving about the discomfort now.
This essay started because I’d been on a run of writing and building around strategic thinking — a three-part series (The Strategy Skill Gap, How to Communicate Strategy in 3 Slides, AI as Your Strategy Chief of Staff) and an open-source Strategy OS project for Claude. All of that is about making strategy more structured and teachable. But somewhere in the middle of it I started thinking about the places where I’d had to challenge my own instincts, and I realized the lived experience of strategy is the part that usually gets left out.
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