My Single Biggest Takeaway from Lunch with Jason Fried and Troy Henikoff

We recently had the pleasure of having lunch with the very successful Troy Henikoff (CEO of Excelerate Labs) and Jason Fried (President of 37Signals).  We discussed a number of topics, all centered around Unbranded Designs and what we are trying to achieve.  A number of learnings came from the discussion, but perhaps the most impactful one didn’t surface until after we had finished lunch.  After dropping Jason back at his office, Troy turned to us and said, “Friendly feedback. Sometimes you need to just shut up and listen.”

As we recapped the discussion, Troy pointed out that we spent much of the meeting talking.  In our minds, we were trying to give Jason, someone who knew nothing about our business, as much information as possible, so that he could offer informed feedback back to us.  Unfortunately, in trying to do so, we rendered someone far smarter than us practically mute for large parts of the discussion.

And here’s the really scary part: we would never have known that we were doing that if Troy hadn’t pointed it out!  On the surface, the conversation was lively and free-flowing, and we still walked away with a number of great takeaways.  But as I look back, I realize how much more we could’ve gotten from the conversation by simply prompting Jason with some very basic thoughts and letting him ask and probe from there.

Looking back, I also realized that Jason engaged in this type of “active listening” a number of times during our lunch.  We would be discussing some random topic and he would ask an open-ended question to the group and sit back and listen, sometimes pushing the discussion forward with a follow-up.  Now I have no idea if he intentionally tries to do this, or it just comes naturally, but it speaks volumes that someone so successful (and opinionated) spends much of his time listening.

So to all of you meeting with advisers, investors, and others whose guidance you really want, keep this story in mind.  Sometimes it pays to just shut up and listen, even if it is really hard.  As Troy said, “you have two ears and one mouth for a reason.”


12 thoughts on “My Single Biggest Takeaway from Lunch with Jason Fried and Troy Henikoff

  1. Mike Ghano says:

    Pretty interesting advice. Don’t you think there’s a tangible benefit to offering up a really solid overview of what you are doing though? That way, you can guide the conversation to get feedback in the areas you really want input on.

    • Sameer says:

      Sure it’s always a balance, but the point is that it’s easy to overshare and waste time when you could be getting more feedback and letting the other people in the conversation draw out their own insights

  2. Kat V. says:

    This is seriously good advice. I am constantly amazed at how often people choose to talk and inflate the room with their presence instead of sitting back and listening. There’s always something to learn, regardless of who you are talking to, especially with someone like Jason Fried!

  3. Kunal says:

    I mean, this is a fine post in a vacuum. The harder part is actually sitting back and shutting up in the heat of the moment. I agree with Sameer that there is value in it, but not sure if the difficult part is simply recognizing it, or actively practicing it in situations like this.

  4. Matilda says:

    I don’t know who either of these guys are (I’m a designer, sorry!) but good feedback for design world too. Too many times designers are stuck in their own visions, aren’t willing to sit back and listen to advice and guidance from others who have far more experience.

    Sometimes can be a fine line whether you want to compromise on your artistic vision, but still it’s a valid point that you should take the time to listen to those around you!

    Sameer – what else did you learn from the conversation?

    • Sameer says:

      Thanks for the comment. A lot of the discussion focused around what we should be immediately trying to accomplish, as well as having a clear vision of who we are and what we believe. Interesting stuff overall

      • Matilda says:

        Fascinating! I think it’s so cool what you guys are trying to do, it’s fun to hear from the other side the kinds of things you learn about! I hope you keep doing these sorts of posts

  5. Janine says:

    The hard part is not sitting back and listening, the hard part is getting a lunch with people like Troy and Jason in the first place….

  6. Jake says:

    This post was cool beans! I’d love a follow-up post on some of the other things you learned from the conversation

  7. Anonymous says:

    Great Advice!

  8. Jon Kindder says:

    Sound advice. Agree that this is very difficult to actually accomplish when you have a million thoughts running through your head!

  9. Bryan says:

    Nice post Sameer

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