Think Big, Think Small
Years ago, I joined a workshop that the leader called Think Big, Think Small. Just ten of us: product, engineering, and design. Ninety minutes. The timer split the meeting cleanly in half.
For forty‑five minutes, we dreamed. We imagined the product our customers would rave about a year from now, and the kind of company we wanted to become. When the buzzer sounded, we shifted gears. The next forty‑five minutes answered a single question: “Great. What do we ship in the next two weeks?”
The format was simple. But the mindset stuck with me.
It invited people to care about both the long arc and the next move. To think like owners. To turn vision into momentum.
That mindset is rare. Even when you try to model it.
The Bias Toward Action (and the Cost of Skipping the Thinking)
We all know what our industry values: action. Move fast. Get feedback. Avoid analysis paralysis.
There’s real wisdom in that. Feedback loops matter. If you're stuck, try something. Learn by doing.
But here’s the question I keep asking. How often does your team step back to ask, “Is this the right next move?” Or do they just run the play that’s in front of them?
Even when you think you’ve built a culture that makes space for thinking, urgency has a way of squeezing it out.
Just this week, one of our most senior engineers told me we needed to take more time to think. I pointed to recent decisions—complex ones—where we had taken the time. I reminded him how our deliberate approach had made key projects possible.
He nodded. “You’re right,” he said. “But that’s not how it feels on the ground.”
What he meant was that his teammates were still pushing for action above all else. They cared deeply about the business and wanted to move. That’s good. But the value of pausing to think and plan wasn’t always sinking in.
That moment reminded me: building a thinking culture is not a one-time act. It’s an ongoing practice. Even when your message is clear from the top, it can get lost in the rhythm of shipping. The pressure to move is constant. The habit of pausing is fragile.
Planning Isn’t the Enemy of Speed
I've spent most of my career working on developer platforms, at startups, at Canonical, at Heroku, at Snyk, and now at Kard, where we’re API-first by design. I’ve lost count of how many times I’ve heard “We shouldn’t overthink this. Things will change anyway.”
And sometimes, they do.
But I’ve found thoughtful design upfront is what buys you flexibility later.
A few months ago, we ran into friction around a particular API design. A new use case didn’t quite fit the structure we had. But because we’d anticipated similar scenarios during early planning, we didn’t have to rip everything up. We had seams. We had context. And we moved forward.
Planning didn’t make us right. It made us ready.
“Plans Are Useless. Planning Is Essential.”
That line’s often attributed to Eisenhower, and it holds up. The moment reality hits, your plans will likely fall apart.
But if you’ve done the thinking—really wrestled with the tradeoffs—you’ll adapt faster and better. Not because you’re clinging to the plan, but because your thinking is already in motion.
Good planning is like packing for a hike. You won’t know every turn in the trail. But you’ll be ready when the weather shifts.
Five Ways to Build a Thinking Culture
Here’s what I’ve found most helpful for bringing deliberate, business-aligned thinking into product-engineering teams:
Share the business story. Strategic thinking starts with context. I want every engineer on my team to be able to explain the “why” behind what we’re doing—in plain language. That means regular storytelling, clarity from leadership, and transparency about what’s changing.
Make time to think. If you don’t carve out space, urgent work will fill every corner. In my org, we schedule time twice per quarter—individually, in small groups, and with leadership—to step back and reflect on direction.
Anchor ideas in business value. Strategic thinking isn’t about sounding smart. It’s about moving the business forward. Whatever your specialty, be a businessperson first.
Plan with change in mind. Don’t try to control the future. Instead, plan for it to change. Use scenarios. Design with seams. Agility comes from preparation—not just improvisation.
Tie strategy to immediate steps. Big ideas aren’t enough. You’re not done until you’ve answered, “So what do we do right now?” Thinking must lead to action, or it’s just noise.
Closing Thoughts
Think Big, Think Small stuck with me because it does both: it invites vision and demands action. It respects the power of thinking, but doesn’t stop there.
We work in a fast-moving field. But speed, untethered from direction, invites waste. If we want to build products that matter, to customers and to the business, we have to carve out time to think.
See the map. Sketch the vision. Then take the next step.
