Every morning, Max and I begin our walk exactly the same way.
We leave the house, head down the sidewalk in front of our yard, and make our way toward the corner at the end of the block.
Up to that point, there’s really only one direction to go.
But once we reach the corner, everything changes.
We might continue straight toward the neighborhood park. We might turn left, adding extra distance and exploring a few quieter streets. Or we might turn right and take the shortest route around just our immediate block if we’re pressed for time and/or energy.
Sometimes the decision is practical.
For example, if it’s already getting hot, we’ll choose the shadier direction or even just the side of the street that offers the most shade.
Sometimes the decision is made because of Max and his needs. If we spot another dog coming our way, we’ll often head in a different direction. Max still carries a little uncertainty from whatever happened before he came to live with us, and giving him a little extra space usually makes for a happier walk.
And every now and then, I turn the decision-making completely over to Max. His nose catches an interesting scent, and suddenly we’re headed somewhere I hadn’t planned or even really considered.
The funny thing is, every walk begins exactly the same.
But then one small pause at the corner changes everything that follows.
It occurred to me recently that my business has corners like that, too.
Not literal street corners, of course. But rather moments where I pause long enough to ask a different question before deciding which direction to take next.
Because the direction of my business isn’t determined by where I start each morning.
It’s determined by the questions I ask before I choose where to go.
🌿 Welcome to the YOU, Inc. Series
This article is part of a leadership series for work-from-home entrepreneurs.
Each week, we’re exploring practical ways to run your business like a CEO while leading the most important company you’ll ever build:
YOU, Inc.
Together, we’ll keep returning to one simple question:
What would the CEO of YOU, Inc. choose?
✨ In This Article
If you’ve ever felt stuck solving the same problems over and over again, it may not be because you need better answers.
It may be because you need better questions.
In this article, you’ll discover why thoughtful questions help entrepreneurs make better decisions, notice new opportunities, and intentionally choose the direction of their business instead of simply following the path that’s already in front of them.
Most of Us Ask Survival Questions
When life gets busy, our focus narrows and our questions tend to shrink. We start asking things like:
- How do I catch up?
- How do I answer all these emails?
- How do I get through today’s to-do list?
Those aren’t bad questions.
They’re simply survival questions.
The problem is that while survival questions naturally keep us focused on what we need to do to survive today, they rarely invite us to think about tomorrow.
That’s one of the reasons a Weekly CEO Meeting has become such an important leadership habit for me.
It gives me permission to step out of the weeds of daily work long enough to ask bigger questions.
Not because I expect immediate answers.
But because better questions change what I notice.
The Pause at the Corner
I’ve come to realize that what I love most about my walks with Max isn’t really the actual walking …
It’s the pause.
It’s those moments when, for just a moment, we stop. We look around and notice what’s going on around us. We consider our options. Then we choose how to proceed.
I’ve also come to realize that business leadership works the same way.
Without the pause, it’s easy to keep moving in the same direction simply because that’s where we were already headed.
Leadership lives in the pause.
The pause is the space between reacting and choosing. It’s the moment when you stop asking, “What’s next?” and begin asking, “What kind of business am I trying to build?” or “What kind of week do I need?”
Some days call for longer walks. And some days call for shorter ones.
Some days call for quiet. Others invite exploration.
The best choice on any given day depends on where you are, what you need, and what season you’re in.
On any given day – whether it’s on a walk or in your business – the pause is where you make that intentional choice.
Better Questions Reveal Better Possibilities
Years ago, I believed leadership meant having the right answers.
Now I think it has much more to do with asking thoughtful questions.
Questions like …
- What’s working better than I realize?
- What have I been avoiding?
- What deserves more of my attention?
- What’s no longer serving me?
- What opportunity am I not seeing yet?
Notice something about those questions?
None of them demand immediate action. They simply invite awareness.
And awareness almost always comes before meaningful change.
The Quality of Your Questions Shapes Your Leadership
It’s tempting to believe that successful entrepreneurs simply know more.
I don’t think that’s true.
Instead of knowing more, I think they stay curious longer.
They resist the urge to grab the first answer that appears. Instead, they explore. They reflect. They notice patterns. They ask one more question … and then another.
And often, that’s where the breakthrough begins.
Not because the answer magically appears …
But because the right question changes what they’re able to see.
You Don’t Need All the Answers Today
One of the most freeing realizations I’ve had over the years is that not every CEO Meeting has to end with a decision.
Sometimes the most valuable outcome is simply identifying a question that’s worth carrying into the week.
Instead of rushing to solve it, you let it simmer. You notice what comes up during conversations. You pay attention to the ideas that arrive while you’re walking the dogs. Or working in the garden. Or folding laundry.
Our brains have a remarkable way of continuing to work on thoughtful questions when we give them the time and space to do so.
Sometimes the answer doesn’t arrive because you worked harder.
Sometimes it arrives because you finally stopped demanding that it appear immediately.
🌿 Action Step for This Week
During your next Weekly CEO Meeting, choose just one leadership question.
Don’t try to answer it right away.
Instead, write it at the top of a page and carry it with you throughout the week.
Notice what conversations, ideas, experiences, or observations begin connecting back to that question.
Then ask yourself:
What changed simply because I started paying attention?
You may discover that the most important shift wasn’t finding a better answer.
It was learning to ask a better question.
🌿 A Question Worth Sitting With
If I changed nothing about my business except the questions I ask myself each week … what new direction might become possible?
You don’t have to answer it today.
Just let it keep you company for a while.
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💛 This Month’s Mini Power Tool
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FAQs
Here are some frequently asked questions around the idea of leadership questions for entrepreneurs that can change the direction of your business.
Helpful leadership questions include: What’s working better than I realize? What have I been avoiding? What deserves more of my attention? What’s no longer serving me? And what opportunity am I not seeing yet? These questions create awareness, reveal new possibilities, and support more intentional decisions.
Better questions change what you notice. Instead of keeping your attention focused only on immediate tasks and problems, thoughtful questions help you recognize patterns, explore opportunities, reconsider assumptions, and make decisions with greater clarity.
A survival question focuses primarily on getting through the immediate workload. Questions such as “How do I catch up?” or “How do I finish today’s to-do list?” can be useful, but they rarely create space for strategic thinking or long-term leadership.
A Weekly CEO Meeting creates dedicated space to step away from daily tasks, consider what is working, identify what deserves attention, and explore important questions before making decisions. The goal is not always to leave with an immediate answer; sometimes identifying the right question is the most valuable outcome.
No. Some questions are worth carrying with you throughout the week. Giving a thoughtful question time to “simmer” can help you notice relevant ideas, conversations, experiences, and patterns without forcing an immediate answer.
Begin by pausing long enough to consider your goals, current needs, available resources, and the season you’re in. The best direction is not always the longest, fastest, or most ambitious route. It is the one that intentionally supports the business and life you are trying to build.
“Leadership lives in the pause” means that intentional leadership often happens in the space between reacting and choosing. Pausing gives you time to notice what is happening, consider your options, ask a better question, and decide how you want to move forward.