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.
For the first five years, our organization operated without written values.
At first, it didn’t seem to matter. We were small, close-knit, and aligned by instinct. But as we grew, the cracks began to show. Departments started working in silos, communication broke down, turnover climbed, and morale slipped.
Our culture wasn’t toxic; it was just undefined. In many ways, it was accidental instead of intentional.
That tension finally pushed us to sit down as a team and define who we wanted to be, and how we wanted to work together.
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.
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.
The world doesn’t need another podcast. But this post isn’t really about podcasts. It’s about the pressure to jump on what other organizations are doing – a newsletter, a blog, an influencer program, a local ambassador program, you name it.
These things could very well advance your organization. But “because everyone else is doing it” is not a strategy. And for us, these were intentional add-ons that pay returns.
Start with the problem you’re trying to solve or a specific audience you’re trying to reach. Then ask: Is this the best tool for that job?
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.
