Caitlin Ferguson can spot the pattern from across the room.
A founder stands at the whiteboard, marker in hand, drawing boxes and arrows. They’re mapping the perfect system, the ideal workflow, the flawless go-to-market strategy. They’ll get it right on the whiteboard, then execute.
Except they won’t.
After working with over 100 founders and helping them generate more than $20 million in value, Caitlin has learned this: the whiteboard is where good ideas go to die.
She told me she’s had to physically kick founders away from whiteboards. Not metaphorically—literally walk over and say, “No. Close the notebook. Go have the conversation.”
Because here’s what she’s learned: no battle plan survives first contact with the enemy.
The whiteboard feels safe. You can control every variable. You can architect the perfect solution without risk, without rejection, without discovering you were wrong. But Caitlin can’t think of a single time where the idea a founder perfected at the whiteboard matched what actually gained traction in the market.
It’s only through iteration—through real conversations, beta tests, and messy first attempts—that you discover what actually works.
This insight alone was worth the conversation. But she didn’t stop there.
The real cost of not letting go
The whiteboard problem has a twin: the letting-go problem.
Once you hire your third, fourth, fifth person, you face a new trap. You’ve got capable people around you, but you can’t quite release the reins.
Caitlin gets it. You built this thing. You know every corner of it. And yes, if you did it yourself, it would probably be done exactly right.
But “exactly right” isn’t the goal. Growth is.
She was firm on this: if you don’t learn to zoom out and delegate effectively, you won’t scale. You’ll have an expensive hobby that burns you out fast. She’s watched it happen too many times.
This is where she introduced me to situational leadership. It’s a framework that shows you how to progressively hand off responsibility—when to sit side-by-side walking through each step, when to pull back and give space, when to trust they’re ready for full ownership.
Most founders hold on too tight or throw people in the deep end with no support. Situational leadership gives you the checklist to recognize: this person is ready for the next level of autonomy. Or: this person needs more scaffolding, and I need to plan for that.
Decision journaling: How she learned to trust her instincts
When Caitlin was building her first business, she made a high-stakes decision and then spent days replaying it in her mind. Did she miss something? Should she have chosen differently? What if it fails?
She needed a way to stop second-guessing herself.
So she created what she now calls decision journaling. The format is simple: I’m making this decision. Here’s the context. Here’s the outcome I think will happen based on what I know today. Then close the notebook and don’t look at it again until the outcome arrives.
Sometimes she discovered blind spots. But most of the time, she learned her instincts were sound. That built confidence.
Building a business means making decisions on limited information, constantly. Decision journaling trains you to trust your judgment and identify exactly where you need to grow.
I’m absolutely stealing this framework.
Making AI actually useful
Founders know AI is here. Most have played with ChatGPT. But they’re stuck on the same problem: how do you make AI operationally useful in your business without a development team or expensive software?
Caitlin got frustrated with AI because it felt like constant coaching. She’d get an output and think, “Great, but no.” Then she’d give it another prompt. And another. She was just unblocking her own writer’s block by eventually doing the work herself.
So she built what she calls a keystone document. It’s a single, platform-agnostic framework that teaches AI how to work within your context.
Here’s where it clicked for me. The document has three components:
Your values and quality bar. For Caitlin, something has to feel generous first—it has to make people feel seen and exceptional. When AI knows your values, outputs align with how you actually work.
Your frameworks for thinking. You have mental models for solving problems. Write them down. If you assess community members, document your criteria. If you evaluate clients, capture that matrix. AI can apply these frameworks consistently.
Prior successful work. Examples of what worked before. When Caitlin tackles a new client challenge, she’s often pulling from a similar situation she’s seen. AI can do the same if you give it the reference library.
With her keystone document, she can take a sales call recording, feed it to an LLM, and get a client-fit assessment, a list of aligned services, and a draft proposal using language the prospect actually used—all in 5 to 10 minutes. No technical lift. No steep learning curve.
One founder told her they wished they’d had this document when onboarding people, because it captures the frameworks they’ve never written down. It’s valuable beyond AI.
Sales doesn’t have to feel icky
Many founders hate sales. It feels transactional, self-promotional, gross.
A mentor once asked Caitlin: “Do you genuinely believe you can help people with what you know?”
She said yes.
The mentor said, “Then why are you uncomfortable sharing that knowledge to possibly help somebody get unblocked?”
That reframe changed everything for her.
Sales feels icky when you center it on the transaction. If you come at it as a problem-solver—hey, you’re struggling with X, and I know how to make that sticky spot go away—it stops feeling like self-promotion. You’re just offering help.
This applies to thought leadership too. Caitlin used to think posting on LinkedIn was like standing on a chair in a restaurant and shouting. Then she realized: if she genuinely has knowledge that could unblock someone, sharing it isn’t showing off. It’s useful.
Sales is a skill. It’s learnable. And once you reframe it as helping rather than selling, it gets a lot easier.
Why this is the golden age for founders
This year has been brutal. Markets are volatile. AI is throwing curve balls. Caitlin has had countless conversations with founders asking, “Am I insane? Should I just get a job?”
Her answer caught me off guard: you’re not crazy. But you’re also standing at one of the most interesting inflection points for building a business.
AI is disruptive, yes. But disruption creates opportunity. The internet didn’t decimate industries—it created net new jobs by opening up problems that didn’t exist before. AI will do the same.
Founders who figure out how to fold AI into their businesses in unique ways, or who become experts in the new problems AI creates, are positioning themselves as first-movers in a massive shift.
If you’re on the fence, don’t give up. Take a different lens on it. This is a golden age if you know where to look.
This essay is adapted from my conversation with Caitlin Ferguson on the Generalist World podcast. [Listen to the full episode here.] Caitlin does embedded operations for founders, helping them build businesses that thrive without burning out. You can find her at coopilots.io or on LinkedIn. She’s also part of the Generalist World community.
