The future belongs to those who ask the right questions

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.

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    The biggest crisis facing young Americans today is a lack of purpose. They wander through life weighed down by hopelessness, convinced the future isn’t worth fighting for. They can’t afford basic necessities because of rising costs and stagnant wages. They’re told they’ll never have homes. Marriage and kids are, for many, out of the realm of possibilities. And to make it all worse, the climate doomers say they won’t have a future because climate change will suffocate us all.

    The emptiness many young people feel today is profound, and originates from multiple sources, but one especially stands out: climate doomerism, the belief humanity is on an unstoppable march toward destruction, has become a defining feature of our generation.

    The story told to millions of young people is the planet is dying, the system is rigged, and the future is lost. When that message becomes the moral framework for a generation, what hope is there?

  • The Four Foundations of Impactful Organizations

    If you dive into books or articles on building great organizations, you’ll find no shortage of frameworks, models, or operating systems. I’ve studied and used pieces of nearly all of them for about a decade now. But none quite fit the kind of organizations I’ve worked in: organizations created to solve big problems and create lasting impact.

    After a decade of leading organizations, I’ve come to learn that every healthy and effective organization is built upon four foundations – Impact, Talent, Operations, and Ownership. And when these foundations are built well, they allow every corner of the organization to fire on all cylinders.

  • Personal systems take time

    One of the most common issues I see in management, especially with early-career employees, is a struggle to stay organized and manage time well.

    I have empathy for it because I was the same way. In college and my early career, I bounced between to-do apps, note-taking systems, project management tools, paper journals, and weekly planning templates. It wasn’t until my late 20s that I landed on a system that not only worked, but that I could actually stick to.

    Personal systems take time to develop. And they should be deeply personal. You can’t just adopt someone else’s setup and expect it to work without modification. Everyone’s wired differently. What clicks for me might drive you crazy – and vice versa.

    When we talk about personal systems, we often think of task lists and calendars. But it’s broader than that:

    • Macro tracking for fitness or nutrition
    • Personal reviews and reflections
    • Goal tracking
    • Morning routines or end-of-day resets

    All of these systems help us stay on track, but ask anyone who uses one and they’ll tell you they are tough to master. Good systems take time to create and refine, and they should make your life easier, not harder. If you’re constantly fighting to maintain it, it’s the wrong one.

    If you’re still figuring it out, be patient. Experiment, reflect, and adjust as needed. The goal isn’t to get it perfect; it’s to get something that helps you show up for yourself and others consistently.

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  • Own your lane

    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.

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  • Building the plane while you fly it

    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.

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  • Be strict with yourself and tolerant of others

    The great Stoic philosopher, Marcus Aurelius, said that. And I forget it all the time.

    Like when my partner loads the dishwasher in a way that makes my eye twitch. After all, I’ve spent almost a decade figuring out the most optimized way to load the dishwasher, and they’re throwing dishes in there like it’s a trash bin.

    This is how I’m wired – and I know it’s not always easy to be around. But I value order and systems. I like things done with care, done efficiently, and done right. And I hold myself to that standard.

    A problem arises, though, when I hold others to this high standard. I expect people to think the same way, act the same way, and have the same general mindset. And, surprise, that leads to way more frustration than contentment.

    When I get too rigid about how others should operate, I’ve noticed that resentment begins to creep in. I start to feel frustrated and silently hold people to expectations they never agreed to. I get annoyed when they don’t approach things the way I would.

    That’s not leadership. That’s immaturity. And it’s something I wanted to share that I’m working on in case anyone else relates to this dynamic.

    The Stoics got it right – focus only on what you can control – even if that’s easier said than done.

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