How to take a punch

I'm baaaack

Hello to my new and longtime followers. This week, I got back into the newsletter game with a post on Lenny’s Newsletter called “How to become a supermanager with AI.” If you have a chance, give it a read (and maybe a like!). I’ve spent the past year experimenting with AI as a management tool and have been genuinely surprised by just how useful it can be.

How to become a supermanager with AI

Here are a few tools I’ve had fun building:

1. The Executive Editor: Paste in any draft message you’ve written and it will offer you specific suggestions for improving your writing for an executive audience.

2. Product Logic Coach: Logic games for PMs. Type “Go” and have fun.

3. 30 days of GPT: If you are not sure where to start with AI, or feel like you have given it a try but struggle to get an actually usable output, this training guide is for you. I made it to help you develop an instinct for how to collaborate with AI in less than three minutes a day.

Anyway, I didn’t originally plan to write about AI. The original concept I pitched to Lenny was called “How to Take a Punch,” and it explores what I believe to be the most essential skills for thriving at work: learning to face threats to your ego without defensiveness and counter-programming negative impressions.

Lenny correctly predicted that people were more interested in AI than emotional regulation, and I am grateful for his guidance. Still, I liked the essay so I thought I would share it with you all.

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To grow in your career, you have to put yourself out there: speak up in meetings, champion your team, pitch the CEO. You can improve your communication skills and build your confidence, but this will only get you so far. When you err toward speaking up, you will inevitably stumble and say the wrong thing.

Imagine you’re recapping a successful product launch in an All-Hands. Someone asks: “Why did you prioritize this over xyz thing that every customer wants?” You sense contempt in their voice. Or are you imagining it? You freeze and respond defensively: “Well, prioritizing is hard. We can’t let every customer request chew up our limited resources.” You see members of the audience exchange looks. Immediately you know you’ve lost the room. You endure a few more questions and slink back to your seat. What now?

You’ve stepped in it, and you’re probably in your head about it. You may want to pretend it never happened and hope everyone forgets — or try to rectify the situation. Neither will effectively disabuse anyone of the impression you gave them.

You might reach out, apologize, and explain the business case for your new product. This can backfire. You're asking them to reassure you (which can seem needy) and over-explaining feature choices (which can make you seem defensive). More importantly, it doesn't address the their fundamental concern that you dismiss customer feedback, lack empathy, or make inflexible decisions.

Rather than drawing more attention to your misstep, learn to counter-program the negative impression you may have left:

💡 Ask yourself what negative impressions the other party may have of you, then come up with one quick way to demonstrate that those impressions are wrong. 💡

It can be hard to do this if you start getting defensive. Signs you are getting defensive include: you become overly focused on the faults of the other person’s delivery (“they should have messaged me that privately instead of putting me on the spot”), you start justifying your own actions (“Sure, if I had unlimited resources I could built their feature request, but they don’t understand my constraints”), or you start identifying what you think is wrong or unfair about their feedback in order to “cancel out” what might have been right about it.

Try to notice if you regularly find yourself getting defensive in these times. Emotional regulation takes focused work but it pays itself off in dividends. One way to better process defensiveness is the “two lists” method. When someone says something that triggers your defensiveness, draw a vertical line on a piece of paper. On the right side of the line, write down what might be “wrong” about their feedback. Then on the other side, put yourself in their shoes and write down what might be “right” about it. This allows you to hold two things in your mind at once: nurse your wounds and have your well-deserved pity party (you do deserve it!!), while also giving them the benefit of the doubt and searching for kernels of truth in what they were saying.

Then comes the most important step: do something about it. Don’t focus on what happened. Identify the negative narrative that person might have about you in their head, then take action. “Action” is not litigating the past. It is asking yourself, “What kind of person do I want that person to think I am? And what action would irrefutably demonstrate that I am that kind of person?”

I work at WHOOP, and once had an executive suggest I add psychedelic tracking to a feature we were reviewing. I chuckled, thinking it was a joke. It was not. She asked me not to make light of addiction.

I was gutted. I take addiction and mental health seriously, and being misunderstood on such a deep level was physically painful. On top of that, I didn’t want her to think I was dismissing an opportunity to address emerging health issues before they became mainstream. It’s not exactly good when executives doubt your ability to anticipate where the future is headed.

After the meeting, I challenged myself to find one small way to demonstrate that I care about addiction issues and this moment in public health as quickly as possible. I asked Perplexity to pull recent articles on an issue I see looming in the space: gambling addiction in young people, fueled by sports betting. I sent a note, making sure to cite my sources:

I love that you’re thinking about this—it’s such an important area. I’ve been tracking similar trends in behaviors that could spiral into widespread health crises. Sports betting and gambling addiction are real concerns, particularly among young people. We might explore tracking their health impacts to stay ahead of a growing public health challenge.

This turned into a fruitful conversation and the executive thanked me for driving it forward.

People might not remember exactly what you said, but they’ll remember the impression you left. You can’t unsay something, but you can always shift how people see you through what you do next.

(BTW, we just launched psychedelic tracking in WHOOP.)