You probably don’t need a podcast

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.

Not everyone should be a manager. More people need to say that out loud.

We think moving up means moving into management. Organizational leaders assume the only way to promote someone is to give them people to manage. Early career professionals assume it is the only path to advancement and higher pay.

One of the worst, most draining mistakes you can make is stepping into management when you are meant to be a strong individual contributor.

Management means putting down your craft to lead people and develop the next generation. Being an individual contributor means building deep expertise. Both paths are valuable. Both are needed. You have to know which one fits you.

Management brings its own stress: hard decisions, hard conversations, and responsibilities you can’t just check off. But the reward of helping others grow is real.

Some people thrive as specialized individual contributors. They become highly valued and well paid, without managing a team.

Success comes in many forms. Pick the one that fits you.

Neither is your organization. I know that’s really hard to hear or accept.

You’re not so unique that the basics of leadership, systems, and clarity don’t apply to you.

You’re not so unique that you just happen to attract bad hires. Maybe you have weak management.

You’re not so unique that setting clear goals, building a healthy culture, and creating clarity somehow aren’t “your thing.”

Saying you’re unique is convenient. It’s a way to avoid change, sidestep responsibility, and ignore the hard truths every other leader eventually has to face.

The good news is, you’re not alone. But you’re not exempt either.

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.

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’ve sometimes seen a desire to throw $100,000 in salary and benefits at a “bandwidth problem” when it’s really just a prioritization problem.

Sometimes, hiring is absolutely the right decision. But sometimes, the better solution isn’t hiring, it’s doing fewer things better.

Before you hire, ask these questions:

• Are we trying to do too much? The instinct to say yes to everything creates artificial capacity problems. What if the issue isn’t a lack of people, but a lack of focus?
• Can we cut or pause lower-priority projects? Every initiative competes for attention. Which ones could you shelve without meaningfully impacting your core objectives?
• Are we clear on what actually created results? If you can’t identify your highest-impact activities, adding more people just increases the confusion.
• Could we streamline operations or automate some work first? Process improvements and automation often free up more bandwidth than a new hire, without the ongoing cost.

Hiring should be a strategic growth move, not a reflex to wrangle chaos. Sometimes the real answer isn’t adding people, it’s tightening focus.