Are you holding your business back?

Why your business won’t evolve until you do—and 25 questions to start the process

I can’t stop thinking about the story Gui Loureiro told me when he appeared on my podcast last month.

At the time, he had been CEO at Walmart Mexico for about a year. The company was performing well. The team was strong. From the outside, it looked like a textbook success story.

But Gui had a bold vision: to lead the company into the digital era. He called in his executive coach, Carlos Marin, and asked for help convincing his executive committee to move fast—despite the fact that Walmart Mexico was already ahead by traditional standards.

Carlos listened, then asked Gui a question that stopped him cold:

“Who’s going to be the CEO when we transform the company?”

Gui, already the CEO, was a little confused by the question, and replied: “It’s me, Carlos!”

But his coach shook his head. “You grew up in command and control,” he told Gui. “When you think you’re right, you don’t listen. You cannot be the CEO of a much more agile company, much more digital [company]. You’re not the right guy.”

Gui was stunned. He had the title. He had the results. But he didn’t yet have the mindset.

That conversation became a turning point. He committed to change how he listened, how he empowered others, and how he navigated uncertainty. As he told me:

“I had to change to deserve the job I already had.”

Boy, that line has stuck with me.

Because titles don’t transform companies. People do. And sometimes the biggest barrier to progress is the person in charge. That’s why every leader needs to ask:

Am I the problem?

Not because you’re failing. But because your company’s growth is tied to yourgrowth.

And sometimes, a business isn’t limited because of the team, or the strategy, or the market. It’s limited because of its leader.

If you are brave enough to explore those limitations in yourself—and honest enough with how you respond—you can keep growing into the leader your business needs you to be.

And to help, I’ve put together 25 questions to prompt the kind of reflection that Gui received from his coach.

Now, I’ll be honest: some of these questions might make you squirm in your seat, but as my good friend and former IBM CEO Ginni Romettywisely says, “You only grow when you’re uncomfortable.”

So let’s go!

How Do I Manage My Mindset?

Leading others starts with leading yourself. Your mindset shapes your tone, your decisions, and the expectations you set. When you’re not managing your internal world—when you're reactive, distracted, or operating from fear—it doesn’t stay contained. It leaks into your team’s energy and effectiveness.

To keep your mindset sharp, ask these questions:

• How often do I slow down to think strategically instead of just reacting?
• When was the last time I paused to question my default approach?
• What assumptions am I making that might no longer serve the team?
• In what ways might my certainty be limiting others’ ideas?
• Where might fear—of failure, conflict, or perception—be shaping my decisions?

How Do I Support My Team?

Your job isn’t just to keep the machine running. It’s to unite your team and unlock what’s possible when they work together. That means seeing where people shine. Making space for their input. And making sure they have what they need to succeed. When leaders miss the mark here, it doesn’t just hurt morale. It limits innovation, slows execution, and chips away at trust.

If you want to bring out the best in your team, ask yourself:

• What kind of culture am I shaping through the way I celebrate, critique, and coach?
• How do I handle personalities or styles that frustrate me?
• When someone pushes back or disagrees with me, how do I respond?
• What’s a recent moment where I intentionally stepped back so someone else could lead?
• Who’s bringing value that I’ve unintentionally overlooked or undervalued?

How Do I Handle Change and Pressure?

The way you respond under pressure sets the tone for everyone else. Leaders cast a shadow! If you shut down, spin out, or hold too tightly to control, your team will mirror that. But if you bring steadiness, clarity, and a calm sense of direction, you help your team believe they can move forward, even in the unknown.

Try these questions to reflect on how you lead when stakes are high:

• What do I do (both mentally and physically) when I feel overwhelmed?
• What story would my team tell about how I showed up in our last high-stakes moment?
• How does my communication style change when I am under pressure?
• When change happens, do I tend to become more controlling, more curious, or something else?
• Where might my own lack of clarity be adding to others’ stress?

How Do I Build Relationships?

Results matter. But over time, relationships are what sustain performance. The best leaders aren’t just trusted because of what they achieve. They’re trusted because of how they connect. If your relationships feel transactional or brittle, it’s worth reflecting on what you’re putting into them.

Here are a few questions to help you do just that:

• How much time do I invest in knowing people beyond the role they play?
• What gets in the way of building trust with the people I work alongside?
• When’s the last time I initiated a meaningful, non-transactional conversation?
• Do I make space for others to feel heard, or is my focus on getting my own point across?
• What strategies do I use to create margin and buffer space for nurturing relationships?

How Do I Model Growth and Humility?

Your team won’t grow past your example. If you’re not learning, listening, and evolving, you’re telling everyone around you it’s optional. Great leaders go first. They show what it looks like to own mistakes, stay curious, and keep growing.

Take time to reflect on these big questions this week:

• What’s the last thing I learned that changed how I lead?
• What skills do I need to gain or strengthen, and why haven’t I pursued them yet?
• Where do I still lead from insecurity instead of confidence?
• What systems do I have in place to surround myself with new insights and knowledge?
• How often do I invite feedback, and what do I actually do with it?

Here’s what I know: Your title may not automatically make you the right leader for the next chapter.

But your willingness to ask the hard questions and develop yourself just might.

So this week, take a few minutes and pick a few questions from this list that hit hardest. Sit with them. Talk about them with someone you trust. Let your reflection gently guide you toward an even better version of yourself.

Because like Gui said: You may already have the job. But are you growing into the leader your business actually needs?

So, I have to ask: which question hit home for you? Let me know in the comments, and then tag a leader who isn’t afraid to grow along with you.

Tip: Hit the “save” button by this article’s headline so you can refer back to these questions over the coming months.

Your Next Step

Make the How Leaders Lead app part of your daily leadership routine! It’s 100% free to download and use, no catch.

[Get it now in the App Store]