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Filipe Névola

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Voltar19/04/2025, 14:27

Do We Need Asshole Leaders?

tl;dr: be outcome-obsessed and candid, not cruel. DRIVE problems to solutions fast.

Hey, I hope you're having a great weekend (in Brazil we have two holidays so a long weekend for most).

I need 7 minutes of your time to share two pieces of content I consumed recently and my thoughts on this past week:

  • DHH's rant from March — "Apple needs a new asshole in charge." He argues Apple lost its edge because nobody's willing to play the Steve-Jobs-style hard-nose these days.
  • James Currier on My First Million podcast — he says that a Savage Founder is someone focused on speed. Not speed in any direction, but speed to adapt fast toward success.

Coincidentally, this week I was struggling with how to behave when I need people to deliver more, be more engaged, and specifically what my posture should be. It boils down to the question:

Is acting like a jerk just the price of shipping greatness at incredible velocity?

I think we first need to define what exactly is a jerk or an asshole?

DHH isn't praising generic workplace cruelty; he's talking about someone who puts outcomes as the overall goal of a business project.

In his text, he shows an excellent example where Steve asked: "Can anyone tell me what MobileMe is supposed to do?" and then followed up with "So why the fuck doesn't it do that?"

I don't believe this is being an asshole. This is plain and simple: asking why the outcome doesn't match the expectation directly to the people responsible.

DHH compared this with an interview of Siri leadership defending people not delivering good enough results on AI. Their defense was based on feelings, emotions, hard work, etc.

Hard work doesn't matter; what matters is the outcome. If you need to work hard, great, do it. If you don't, great as well. Focus on the results.

Now, back to the second content: James's talk with Shaan.

James was asked what makes a Savage Founder and he said: "Speed." Not speed in the first direction that was set, but speed to move and adapt to whatever is necessary to achieve goals.

James is the "network effect" guy, so he also talked about relationships. In my experience, the most important network effects come from being friends with people, being fair, and avoiding harm to others regardless of circumstances.

Over time, we accumulate great people around us, creating a network of friends willing to help with whatever we want to do. This is the spirit of a great soccer team and also of a great business team.

You're probably thinking: "What do being an asshole and having a great network have to do with each other?"

Fair question hehe. I'll explain and wrap up:

I believe a great leader is someone willing to be candid at all times, treat people fairly, and change direction fast.

So, do we need the asshole?

No—we need a leader who is:

  • Outcome-obsessed
  • Speed-obsessed
  • Trusted by the team
  • Extremely skilled at the job to be done
  • Bluntly honest, at all times, especially in delicate moments

As I said, I was questioning myself this week on how to behave, and I believe I acted exactly as described above. Here were the steps:

  • I asked the team how I could help and what we could do better by text first; so they had time to think
  • Later we had a video call to look each other in the eyes and discuss candidly what was happening and why the outcomes weren't meeting expectations
  • After we identified the problems without hiding or faking, we started discussing ideas for improvement
  • I ended the video call by tasking the team with writing down the changes we would make moving forward
  • Now we need to check soon to see if things are improving or not
  • If they are, great
  • If they aren't, repeat, be candid again, make changes, and try one more time

If you want a short framework:

  • Define the problem clearly
  • Raise the issue to the team
  • Ideate solutions together
  • Validate the plan
  • Execute immediately

DRIVE steps can be completed in hours, if not minutes.

Is something bothering you right now as a leader? DRIVE it with your team and act!

By the way, if the road diverges from the map, adapt your map, the road is what matters (thought adapted from Gustavo Caetano). You DRIVE on the road, not on the map.