How to Give Feedback Startup Founders Will Actually Hear

Entrepreneur Office Hours - Issue #276

I had a coffee this week with a colleague who also teaches entrepreneurship. During our chat, we found ourselves talking about one of the toughest challenges we face in the classroom: giving negative feedback.

If you haven’t noticed, students these days don’t love hearing it. And I get why. They’re under immense pressure. Everything feels high-stakes. One grade point drop seems like it means missing out on the dream job or internship or grad school offer they’ve been chasing for years. So when they hear constructive criticism, they don’t hear feedback. They hear threat. They hear you’re not good enough. They hear this might mess up your future.

But of course, that’s not what feedback is meant to be. Quite the opposite. When I take the time to give detailed feedback — especially critical feedback — I’m not doing it because I enjoy pointing out what’s wrong. I’m doing it because I care enough to want to help someone improve. It’s me saying, Hey, you’ve got potential, and I’m willing to spend my time and energy helping you unlock more of it.

So I asked my colleague how he approaches this issue. How does he help students — or entrepreneurs, for that matter — see feedback as a gift rather than a threat? His answer was simple but brilliant: he puts on a hat.

Not literally. Metaphorically. Though, he does do a pretend gesture of actually putting on the hat.

“When I’m giving feedback,” he said, “I always tell the entrepreneur what hat I’m wearing. Like, ‘Putting on my investor hat right now… here’s the problem I’d have with your pitch.’ Or, ‘Putting on my customer hat… here’s what I’d be confused about.’”

I love this approach to feedback because it shifts the frame and reminds the people receiving feedback that you’re not attacking them. You’re stepping into a different perspective — a different mindset — and offering insight from that vantage point. It’s not about tearing them down. It’s about helping them understand how someone else might view their work. In other words, it’s empathy in action.

Maybe that’s the real lesson here — not just for educators, but for entrepreneurs, managers, teammates, and creators of all kinds. If we want to give feedback people actually hear and value, we need to make it clear where it’s coming from. We need to model the kind of perspective-shifting we hope our students and colleagues will learn to do themselves.

Anyway, I’m not sure how many of you reading this newsletter are regularly in positions where you’re giving criticism to others, steal the same advice I’m going to steal and start your feedback by putting on a hat. Tell the people you’re critiquing whose eyes you’re seeing them through. And remember, in the end, feedback isn’t about being right. It’s about helping someone else see what they couldn’t see before.

-Aaron

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This week’s new articles…

What Founders Keep Getting Wrong About Entrepreneurship

To build a successful startup, you don’t need another productivity hack. You need a big perspective shift.

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Entrepreneurship Isn’t Supposed to Be Easy — That’s the Whole Point!

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Office Hours Q&A

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QUESTION:

Hey there, Aaron!

My question is about hiring, which is something I haven’t had to do before. I keep hearing the advice that “your first hire is the most important one,” and I’m starting to feel that pressure. I know I really need help, but I’m not sure who to hire first. Do I bring on someone technical? Someone to help with marketing? A generalist?

How do you figure out who your first hire should be—and how do you make sure you don’t screw it up?

Thanks,
Lena

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First of all, you’re absolutely right to be feeling the pressure. Your first hire isn’t just about hiring help. It’s about shaping the DNA of your startup. That first person you bring in is going to set a tone — not just for the work, but for how the work gets done, how decisions are made, and how your company starts to feel on the inside. No pressure, right?

So, how do you decide who that person should be?

The unsexy truth most people won’t tell you is that there’s no perfect formula… everyone is just guessing. And that’s because, quite honestly, the “right” hire depends on your current bottleneck. That’s it. That’s the question to ask yourself: What is the thing that’s slowing me down the most right now? Not what might slow you down in six months. Not what could go wrong if you don’t future-proof. What’s the specific, tangible problem you’re hitting today that, if solved, would unlock the next level of growth?

If you’re a technical founder drowning in code but with zero users, maybe you don’t need more engineering help — you need someone who can help with customer discovery or early sales. If you're great at pitching but can't ship product, then yeah, maybe you need a builder. If you're doing 12 things poorly, maybe it’s a generalist who can take a few off your plate and help you execute with focus.

What you don’t want to do is hire reactively — like bringing someone on just because you feel overwhelmed. Founders often hire to ease their own anxiety, but what you really want to hire for is momentum. Bring in the person who helps you move faster in the right direction, not just someone who helps you breathe easier in the short term.

And whatever you do, just remember your first hire isn’t about perfection. It’s about fit, flexibility, and the ability to figure things out together. That first hire won’t build the whole company. But if you choose right, the person will help you build the momentum to get there.

Got startup questions of your own? Reply to this email with whatever you want to know, and I’ll do my best to answer.