36 hours of pain

Today’s post is simple – please help the victims and communities affected by the devastating flooding in Texas over the Fourth of July weekend. As of this post, the death toll is now over 80 people, and 10 young campers remain missing.

You can donate here.

Every dollar helps.

I was listening to an interview with Sam Altman, CEO of OpenAI, who recently said that in the age of AI, we’ll start valuing different types of people – not just those with the right answers, but those who know how to ask the right questions.

That’s always been true in leadership. The best operators, managers, and strategic thinkers don’t start with great strategic plans. They start by asking good, important questions.

What are we trying to solve here?
What would make this simpler, faster, more scalable, or more valuable?
What does success here look like?
If this fails, why will that have happened?

Like Altman, I am a techno-optimist. While the development side of AI is still very closed off and expensive, access to the fruits of that development – the knowledge – is super affordable and accessible.

The people who can ask the right questions – whether to their AI or to their teammates – are those who I believe will truly excel in the coming decades.

Bonus: Some good questions that managers should ask themselves every week.

Ever look up a recipe and find a short novel before the recipe itself?

Or maybe you received an email from someone, and after three paragraphs, you still don’t know what they want.

Maybe it’s a report or memo that buries the top line info in fluff and filler.

One of the best ways to get a response, earn respect, and win is by getting to the point.

It doesn’t mean being cold – you’re still a human communicating with another human, so respect is a must. It means being concise and clear.

Say what you mean and say it early.

Greetings from day one of my week of PTO. Seemed like a fitting time to talk about one of my favorite benefits: unlimited time off.

A lot of people say unlimited PTO is a scam. And in many companies, it is. But that’s not a failure of the policy; it’s a failure of leadership.

I stand behind unlimited PTO 100%. We use it at my organization, and we make an effort to ensure it gets used. And that’s the key: leaders have to take responsibility for making it work.

You have to build a culture that respects time off. Make it clear people aren’t to be bothered when they’re out. Do a regular inventory of who hasn’t taken time and ask why. Then fix those barriers.

Most of the time, what stops someone from taking PTO isn’t laziness or neglect; it’s guilt. They don’t want to burden their team. Or maybe they’re in the middle of a big project. Or they treat PTO like a golf score, where the lower the number, the more impressive it looks.

Those are all management issues. If someone feels like they can’t step away, that’s often on leadership. Do you have a contingency plan so people can unplug? Are your timelines so inflexible that a few days off will derail everything? What message are you sending – directly or indirectly – about time off?

Your team is too valuable to screw up with a poorly executed unlimited PTO program. Build the systems to make it work.

That $5 donor can become one of your biggest donors.

That new follower can become your future business partner.

The shy intern may run the organization one day.

I’ve been amazed in my career at what the small moments can turn into with some cultivation and patience.

Imagine you’re in a race with competitors flanking you on both sides.

After the starting pistol goes off, there’s a strong temptation to keep an eye on them. You want to see how fast they’re going, whether they’re gaining ground on you. But the more you look, the more you lose your own rhythm and risk stumbling behind.

I’ve seen the same thing happen to organizations and individuals alike. They have competitors – or peers – that they can’t stop keeping an eye on. Maybe it’s FOMO, or just traditional fear, but with every bit of ground a competitor seems to gain, there’s a risk of losing focus on your own lane.

Competitors exist, of course. Awareness is smart, but constant reaction is not.

You need to know your space and who’s in it, but you also need to establish your lane and own it. Someone else’s path is not the path for you. Comparison often disguises itself as clarity, but it usually leads to distraction, loss of direction, and even resentment

Run your own race in your own lane.