36 hours of pain

Sometimes, “building the plane while you fly it” is unavoidable. You just have to take off, move fast, and figure it out on the way.

But here’s the real question: Are you building the plane with duct tape or rivets?

Too often, “building the plane as we fly it” becomes an excuse to cut corners. “Just get it done. We’ll fix it later.” But later rarely comes and temporary becomes permanent. And you’re left flying a patched-together machine at 30,000 feet.

Yes, getting thrown in the deep end can be a great way to grow. But what if you used the chaos to take a beat and build something that lasts?

Even in the rush, you usually have a choice.

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.

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.

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.

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.

One of the reasons I struggled in Spanish class was that I often confused the past tense with the imperfect tense. They looked similar, sounded similar, and both referred to the past… but they weren’t interchangeable.

Strategy and tactics are like that. Easy to confuse, but they play very different roles. It’s a common mistake, and I experience it often.

Think of strategy as the destination and tactics as the directions.

A good strategic goal should be simple and brief:

Increase brand saliency with Gen Z
Diversify donor base across three new geographic regions
Create a strong culture with above-average retention rates

The tactics are in the weeds: partner with Gen Z influencers, host fundraising events in X, Y, and Z cities, launch monthly employee surveys.

A quick gut check to help differentiate the two:

• If changing it would shift the overall goal, it’s the strategy
• If changing it would leave the goal intact but change how you get there, it’s a tactic

Strategy sets the direction, and tactics are the steps. If you and your team aren’t clear on the difference, you’ll end up debating details when you should be defining goals.