Triggers

There’s a certain kind of leader that triggers me, and they tend to have at least one of the following behaviors:

1. They are unable to say “I thought I was right, but it turns out I was wrong.”¹

2. They never ask “What do you think?”²

3. They repeatedly re-decide things when there is no new information.³

Some of this is about them, but some of this is about me. Over the last several years, I’ve been working on myself to get better at working with people like this. I’ve made progress, but to be honest, it’s still not easy.

I’m sharing this for two reasons.

First, if you can know your triggers, you can try to detect them during your interview process. For me, I’ll ask the CEO questions targeting #1 and #3: “Tell me about a time when you thought you were right but it turned out you were wrong?”, and “What’s the culture of the exec team when it comes to debate and decision making?”

Second, increasing your mindfulness can help you in the moments when it’s happening. Over time, you can get better at slowing down, realizing “oh, I’m in that situation again”, then take a beat and deploy the tools you’ve developed to work your way through it.

Everyone has their reactive moments, but the more we can be intentional and less driven by our subconscious, the better.

The Workshop

This is a newsletter-only section where I share a half-baked idea in hopes that y’all who are smarter than me can work it out with me.

For the last 15 months, I’ve been using Arc as my default browser on desktop and iPhone. I love it. They’ve really impressed me with the way they are thinking way beyond the traditional boundaries of what a browser is. Download it here.

In particular, I really like a feature of theirs where, for any Google search query, I also have the option for Arc to generate a custom answer page using GenAI. It includes all the links to their source material so I can dig deeper if I want to.

I wouldn’t be surprised if their end goal is to supplant my use of Google with Arc-powered search, and then start monetizing those results pages.

Anyway, the other day, I was using Arc on my phone, and Arc called me (huh?). I answered the call and this happened:

I then asked it what it was:

I gotta say, I hated this. I have no idea how I caused this call to happen (or was it not something I did?) and the interface was giving me Clippy flashbacks.

I’m pretty sure Apple is going to announce (possibly as soon as their developer event later this month) a new version of Siri, powered by OpenAI or Gemini, which I would expect to be a lot better, because of the unfair advantages Siri can have as something baked into the OS. So I’m not sure where Arc is wanting to go with this. But maybe I’m wrong, maybe conversational chatbots are a more successful UI than I realize.

If nothing else, I’m excited to see how all this plays out.

1  Being hypothesis-minded is the #1 must-have for me. Product is built on this admission that we don’t understand the world perfectly and we can’t predict the behavior of our users perfectly. Instead, we make hypotheses and then we test those hypotheses. Sometimes we’re right and sometimes we’re wrong, and we hope to get more and more right over time.

2  Collaboration in the form of having a voice is really important to me. The decision doesn’t have to go my way and it’s OK if no one agrees with me. But I want to feel like I was heard and had the opportunity to make my case.

3  I’ve written about this before — a culture of re-deciding can kill a company. It slows a company down to a crawl, as everyone is paralyzed because no one wants to get too far into a line of work just in case the decision gets reversed and their effort gets wasted. And, the credibility of leadership gets wrecked in the process.