There Is No Playbook for What You’re Building
Founders and CEOs often say:
“We need someone who’s done this before.”
It’s a comforting idea. When there’s pressure to deliver, it feels safe to bring in someone with a proven playbook, especially when the problem is familiar and the path is clear. That’s the world of complicated problems, as introduced by Cynefin Framework. They’re tough but solvable. With enough expertise, you can find the right answer.
But when you’re building something new, it’s rarely that straightforward. The challenges aren’t just complicated, they’re complex. In Cynefin terms, that means there’s no obvious solution or clear cause and effect. You’re not following a map; you’re making it. And any existing playbook probably wasn’t written for your company, your people, your stage, or your goals.
This isn’t about dismissing experience. Experience matters. But it has the most impact when it’s paired with the ability to read the situation, recognize what kind of problem you're dealing with, and not just apply, but adapt.
Complicated vs. Complex
Once you start to see the difference between complicated and complex problems, something shifts. Complicated problems feel reassuring. Setting up a CRM, conducting a financial audit, or managing compliance are good examples. They can be analyzed, diagnosed, and solved with the right tools and experts.
But that’s not where innovation happens. The most meaningful work, especially in early-stage companies, lives in the complex. And in complexity, success doesn’t come from applying someone else’s system or planning with certainty. It comes from staying curious, testing ideas, sensing what works, and building and adapting the path forward as you go. Think of launching a new product, exploring a new market, or figuring out how to integrate AI into daily workflows.
Understanding which kind of problem you’re dealing with doesn’t just change how you solve it; it changes how you lead through it.
With AI reshaping how companies work, more teams are operating in complex environments.
Building in the Complex
When you’re operating in complexity, the goal isn’t to find someone who’s “done it before.” That mindset prioritizes pattern-matching over context, and often leads to solving the wrong problem.
I’ve seen this play out over and over in my own work and with the teams I support. The most effective moves don’t come from dropping in a perfect plan. They come from staying close to the ground, and shaping the approach in real time.
A Tale of Two Coaches
Consider two types of coaches:
A system-first coach builds a rigid scheme and finds players to fit it.
A personnel-driven coach studies the roster and adapts the strategy to match the team's real strengths.
The first approach works in the complicated domain, where structure solves known problems. The second thrives in the complex domain, where the path forward emerges through iteration and adaptation.
This same idea applies when deciding who to bring into your company, whether it’s a hire, a consultant, or a partner like a fractional executive
What to Look For Instead
The most valuable people right now are not the ones offering certainty. They are the ones who embrace change and ambiguity.
They help your team align, adapt, and take smart steps forward even when the map isn’t finished.
They won’t follow someone else’s playbook. They’ll help you write one that works.