Why Smart Founders Make Bad Business Decisions (And Keep Making Them)

I worked with a founder who kept hiring the wrong people.

Not once. Five times in two years.

Different roles. Different skillsets. Same outcome: within three months, she'd realise they weren't right, spend weeks agonising over what to do, then let them go and start the process again.

She's not stupid. She runs a successful business. She's strategic, thoughtful, good at spotting problems in other people's companies.

But she couldn't see the pattern in her own.

Every time, she hired someone who presented well in interviews. Articulate. Confident. Said all the right things.

And every time, once they started, she'd discover they couldn't execute without detailed direction. They needed her to think for them.

She kept hiring people who looked capable but required her to do the thinking.

Because what she actually needed – someone who could take real ownership and reduce her cognitive load – scared her. If someone else could do the strategic thinking, what was her role?

Easier to hire someone who needed managing. Kept her indispensable.

She didn't realise she was doing it. That's the point.

Intelligence doesn't protect you from patterns

Smart founders make bad decisions all the time.

Not because they lack information. Not because they're not thinking it through.

Because they're caught in a pattern they can't see from inside it.

The founder who keeps saying yes to clients who don't respect boundaries. Different industries, different projects, same dynamic. She can articulate exactly why it's a problem. She just keeps doing it.

The one who undercharges every single time. He knows his worth. He's done the pricing calculations. But when it comes to the actual conversation, he drops his rate. Then resents the client for three months.

The founder who hires for potential instead of capability. Always believes this person will grow into the role. They never do. She's surprised every time.

These aren't stupid people making careless mistakes.

They're capable people repeating patterns they don't recognise.

Why patterns repeat

Because the decision feels different each time.

Different client. Different situation. Different context.

Your brain doesn't flag it as the same decision because the surface details have changed.

But underneath? Same pattern.

You're saying yes because you're worried about money, even though you know this client will be difficult. Last time it was a different worry – maybe credibility, maybe keeping busy – but the mechanism is identical. Fear-based yes.

You're hiring someone who interviews well but can't execute independently. Last time they had a different background, different experience. But the pattern – articulate in theory, struggles in practice – is the same.

You're undercharging because you don't want to lose the opportunity. The project is different. The client is different. The reason you're telling yourself is different. But the behaviour is identical.

And because it feels different, you don't connect it to the last time. Or the time before that.

What makes smart people repeat bad decisions

Pattern blindness. You can see patterns in other people's behaviour easily. In your own? Nearly impossible. You're too close. Your brain justifies each decision as distinct.

Recency bias. You remember the last version of this mistake but not the one before that. So it feels like an isolated incident, not a pattern.

Lack of external perspective. No one's watching your decision-making across months or years, spotting the common thread. You're making decisions in isolation, so the pattern stays invisible.

Rationalisation. Your brain is very good at explaining why this time is different. This client really is worth the boundary violation. This hire really will be the exception. This price really is strategic, not fear-based.

I see this constantly. A founder will tell me about a difficult client situation and I'll ask "has this happened before?"

They'll pause. Think. Then realise: yes. Three times in the last year. Different clients, same dynamic.

They genuinely didn't connect them until I asked.

So what actually helps?

Not better decision-making frameworks. You're already smart enough to make good decisions.

What helps is pattern recognition.

Tracking your decisions over time, not just evaluating them in the moment. When you say yes to something, note it. When you hire someone, write down why. When you set a price, record your reasoning.

Then review it. Not immediately. Six months later.

You'll spot the pattern. The fear-based yeses. The hiring for charm over capability. The pricing that's always just slightly too low.

Once you see it, you can interrupt it.

One client started tracking every time she said yes to a project. Within three months, the pattern was obvious: she only said yes when she was worried about money. Didn't matter if the project was right. If her bank balance dipped, she'd take anything.

Seeing that changed her decision-making immediately. Not because she suddenly had more discipline. Because she could finally see what she was doing.

The uncomfortable bit

Sometimes the pattern serves you.

Hiring people who need direction keeps you central. Undercharging keeps you safe from the risk of people saying no. Taking on difficult clients gives you a reason why the business is hard.

Not consciously. But patterns don't repeat for no reason.

They repeat because on some level, they're solving a problem. Just not the one you think.

And until you're willing to see what the pattern is actually protecting you from, you'll keep making the same decision in different packaging.

If you keep making the same mistakes

If you can describe the problem clearly but keep doing it anyway.

If you feel like you should know better by now.

If the details change but the outcome stays the same.

You're not lacking intelligence. You're lacking pattern recognition.

And you can't see your own patterns without someone outside them.

Here's how we could work together:

One-off mentoring session (£325): 90 minutes where we map the decisions you've been making and spot the pattern underneath. Usually it's glaringly obvious once someone points it out. Book a session

Ongoing mentorship: Monthly support for founders who need consistent pattern-spotting across time. I track what you're doing, spot when you're about to repeat the same decision, and interrupt it before you do. Learn more about mentorship

Because the most expensive business decisions aren't the ones you get wrong once.

They're the ones you keep getting wrong without realising it's the same decision.