You Can't Delegate What You Can't Explain

Here's something I find fascinating about founders who struggle to delegate product decisions.

Ask them why they overrode their product manager's recommendation, and they'll say something like "they don’t get it" or "that's not how we do things" or "I know this customer base better." Press a little harder on what specifically didn't feel right, and you often get a pause. Then something vague about intuition or experience.

Now, I'm not dismissing intuition. Intuition is real. It's pattern recognition that's been compressed below the level of conscious thought. A founder who's spent five years talking to customers and shipping product has genuinely learned things that are hard to articulate.

But here's the problem: if you can't articulate it, you can't transfer it. And if you can't transfer it, you've made yourself a permanent bottleneck. Not because you're the only one smart enough to make good decisions. Because you're the only one who has access to the decision-making process, and you've kept it locked inside your head.

Let me put it differently. When a founder says "nobody else can make this call as well as I can," that's usually not a statement about the team's capability. It's a statement about the founder's inability to explain how they think. Those are very different problems with very different solutions.

The real work

Most advice about founder delegation focuses on the emotional part. Let go. Trust your team. Accept that things won't be done exactly how you'd do them. Learn to live with 80% quality.

I think this framing is backwards, and honestly a bit insulting to everyone involved. It assumes the founder's way is the right way, and the team's job is to approximate it as closely as possible. That's not delegation. That's resigned acceptance of lower standards.

The actual work is both emotional and intellectual, and it's hard in a way that most founders don't expect. The work is this: you have to understand your own thinking well enough to explain it at the level of first principles. Not "here's what I decided" but "here's how I approach this type of decision, here are the factors I weigh, here's what I'm optimizing for, here's what I'd need to see to change my mind."

Most people have never done this. It's way easier to just make the call yourself. It's way easier to review someone else's work and say "no, not that" than to explain the underlying logic that would let them get it right the first time. It's way easier to blame your team for not understanding than to do the introspective work required to make yourself understandable.

Why this is so hard

Here's a thing I've noticed. The founders who are most confident in their product judgment are often the least able to explain it.

This seems like a paradox, but it isn't. When something has become intuitive, you've lost access to the steps. You just see the answer. Asking you to explain your product instincts is like asking you to explain how you recognize a face. You can do it instantly, but you'd struggle to write down the algorithm.

There's a famous bit from Richard Feynman where he talks about the difference between knowing the name of something and understanding it. You can know that a bird is called a "brown-throated thrush" in English and "Chalung" in Chinese, and still know absolutely nothing about the bird itself. The names don't give you any insight into what the bird actually does, how it lives, why it behaves the way it behaves.

I think something similar happens with product intuition. Founders accumulate all this implicit knowledge about their customers, their market, their product. But they've never had to unpack it. They just have a feel for things. And that feel is real! It represents genuine understanding. But it's understanding that's been compressed into a black box labeled "my gut."

This dynamic gets even more dangerous when junior people are watching. When a founder or product executive makes gut-based calls without explaining their reasoning, junior PMs learn that this is what good product leadership looks like. They pattern themselves after it. They start making gut-based calls of their own, except they don't have the ten years of customer conversations and shipped products that made the founder's gut worth trusting. They have vibes. I worked for a product leader once who constantly encouraged the team to "trust your instincts" and "make the call." It sounded empowering. In practice, the team built a lot of total crap, because they were imitating the confidence without having access to the underlying competence. The leader was genuinely good at product. But by failing to unpack what made them good, they bred a team of overconfident guessers.

The delegation problem isn't that the team needs to learn to approximate your gut. The problem is that your gut isn't a transferable asset. You have to decompress it back into principles, and that's a kind of intellectual work most founders have never had to do.

What decomposition looks like

Let me give you an example of what I mean.

Say a product manager brings you a feature proposal and your immediate reaction is "no, that's wrong." You could just say no. You could give some vague feedback about it not being the right direction. The PM will go back and guess at what you want, maybe get closer, maybe not, and you'll do this dance a few more times until either they land on something you like or everyone gets frustrated.

Or you could pause and ask yourself: why do I think this is wrong?

And not accept your first answer. If your first answer is "it just doesn't fit our product," okay, but what makes something fit? What are the characteristics of features that fit versus features that don't? Is it about the customer segment they serve? The complexity they add? The strategic direction they imply? The way they interact with existing functionality?

Keep pushing. Get specific. Find the actual criteria you're applying, even if you weren't aware you were applying them.

Now you have something transferable. You can tell the PM: "Here's how I think about whether a feature belongs in our product. I ask these three questions. The proposal you brought fails on the second one, and here's why." The PM learns something. Next time, they can ask those questions themselves. They might come to a different answer than you would, but at least they're reasoning from the same principles.

This is the work. It's not letting go. It's opening up.

The excuse that falls apart

Founders often tell me they don't have time to explain their thinking at this level. They have too many decisions to make. It's faster to just make the call.

This is true in the short term and catastrophically false in the long term.

Every decision you make yourself is a decision you'll have to keep making. Every decision you make without explaining your reasoning is a training opportunity you've wasted. You're not saving time. You're borrowing it from your future self at an obscene interest rate.

Meanwhile, every hour you spend articulating your principles is an hour that pays dividends forever. Once a principle is understood, it can be applied to hundreds of decisions without your involvement. The math is so favorable it's almost embarrassing that founders don't do more of this.

But here's why they don't: it's genuinely difficult. Much harder than just making the call. It requires a kind of introspection that many successful people have never practiced. The founders who built something real often did it by moving fast and trusting their instincts. Now I'm asking them to slow down and interrogate those instincts. That's not a natural motion for them.

And there's an ego component too, if we're being honest. There's something satisfying about being the one with the answers. Something flattering about a team that needs you to make every important call. Articulating your principles means giving away the magic. Some founders would rather stay indispensable than scale their impact.

What changes when you do this

The shift isn't from "founder makes decisions" to "team makes worse decisions but at least they're moving." That's the version of delegation that everyone's afraid of, and reasonably so.

The shift is from "founder makes decisions using invisible criteria" to "team makes decisions using shared criteria that the founder helped develop." The decisions don't get worse. They get more consistent, more scalable, and often better, because you've stress-tested your own thinking by trying to explain it.

Here's the part that surprises founders who actually do this work: sometimes, in the process of articulating a principle, you realize the principle doesn't hold up. You've been making decisions based on a heuristic that made sense three years ago but doesn't make sense anymore. You couldn't see that when it was intuition. You can see it when you try to write it down and it sounds stupid.

This is a feature, not a bug. Explaining your thinking isn't just about transferring knowledge. It's about examining knowledge. And founders who've been running on instinct for years often have some beliefs that could use examination.

The question worth asking

If you're a founder who's struggling to delegate product decisions, I'd ask you to try something.

Next time you override someone's recommendation, don't just tell them no. Sit with it for a while and try to write down, in simple language, the actual reasoning behind your objection. Not "it didn't feel right" but the specific factors that made it feel wrong. The principles you're applying. The things you know about your customers or your market or your product that inform your judgment.

If you can do that, you've created something valuable. Share it. Let people internalize it. See if they can apply it without you next time.

And if you can't do it, if you try to explain your reasoning and come up empty, that's worth knowing too. It means the work isn't delegation. The work is self-understanding. You can't transfer what you haven't unpacked.

The founders who scale aren't the ones who learned to accept worse decisions from their team. They're the ones who did the hard work of understanding their own thinking well enough to give it away.