Four Questions That Can Change the Trajectory of Your Business
By Mark Moses, Founder and Executive Chairman of CEO Coaching International and Author of Built to Win BIG
A CEO can spend years building a successful business without ever stopping to ask what they really want.
I’ve seen it happen more times than I can count. Revenue is climbing, the team is getting BIGGER, and the CEO is working harder than ever.
From the outside, everything looks great.
But behind the scenes, that same CEO may be exhausted, frustrated, and wondering whether all the sacrifices are worth it.
That’s why one of the most important questions I ask CEOs is also one of the simplest: What do you want?
Not what your board wants, what your leadership team expects, or what you think you’re supposed to want.
What do YOU want?
It’s the first of four questions that have guided my approach to coaching CEOs for years.
What Are the Four Questions Every CEO Should Ask?
When CEOs ask me how to set BIGGER goals, focus their teams, and turn strategy into results, I come back to the same four questions from my Make BIG Happen methodology:
- What do you want? (Vision): Define a clear, measurable goal.
- What do you have to do? (Action): Identify the priorities required to achieve it.
- What could get in the way? (Anticipate): Recognize and prepare for obstacles.
- How do you hold yourself accountable? (Measure): Establish measurable outcomes and consistent accountability.
The Make BIG Happen methodology is a four-question framework I developed to help CEOs clarify their goals, identify the actions required, anticipate obstacles, and create accountability for results.
As I was writing my new book, Built to Win BIG, I realized how much these questions connect the stories of the CEOs and coaches featured throughout it.
The leaders in the book had different businesses, challenges, and goals. But they all answered the same fundamental questions.
Their stories show what can happen when CEOs get clear on their answers and have the right coach in their corner.
One of my favorite examples is Norm Curtis and his coach, David Sobel.
The Question That Changed the Conversation
I first met Norm Curtis in Winnipeg in 2009.
He was running Keystone Western, a struggling trucking company with 25 trucks, significant debt, and a reputation that needed rebuilding.
Norm had acquired the company with two partners, but he was carrying much of the responsibility himself. He was exhausted and didn’t have anyone holding him accountable.
We started working together. Over the years, Norm bought out his partners, rebuilt the business, and became a stronger, more confident leader.
Eventually, Keystone Western was growing, and Norm was ready for the next stage.
That’s when I introduced him to David Sobel, one of our coaches at CEO Coaching International.
David was down-to-earth, approachable, and someone I knew would connect with Norm’s team while keeping everyone focused and accountable.
Their work expanded beyond Norm to include his vice president and sales team. With David’s guidance, they built a sales playbook that dramatically improved their ability to win new business.
But one of the most important moments in their relationship didn’t happen in a boardroom.
It happened at a Winnipeg Jets game.
David turned to Norm and asked:
“What do you really want?”
Norm had spent years fighting to build a stronger business. But that question made him think about what he wanted the business to make possible in his life.
Saying his answer out loud changed something for him.
I’ll leave the rest of that story for the book.
The lesson is one every CEO should consider.
Sometimes you’re so focused on building the business that you lose sight of what you’re building it for.
A great coach helps you reconnect those two things.
The Four Make BIG Happen Questions
These questions are simple to remember. Answering them honestly takes work.
1. What Do You Want? Set a Clear Business Vision
Most CEOs have goals. Far fewer have absolute clarity about what they want.
They’ll tell me they want to grow revenue, increase profitability, or eventually sell the business.
That’s a start, but it’s not enough.
How much revenue? By when? What kind of profitability?
And most importantly: what will achieving those goals make possible for you and your family?
When the CEO isn’t clear about where the business is going, the leadership team starts guessing. Priorities compete. Decisions take longer.
Clarity changes that.
Your action: Write down one BIG, measurable goal for your business over the next three years.
Then ask yourself why it matters.
2. What Do You Have to Do? Identify Your Critical Priorities
Once you know what you want, you have to determine what it will take to achieve it.
This is where a lot of CEOs get stuck.
They have too many priorities all at once:
Improve sales. Expand into new markets. Hire more people. Implement new technology. Pursue acquisitions.
Because everything feels important, nothing gets the attention it deserves.
I’ve always believed in focusing on the critical few activities that will drive maximum impact in getting you where you want to go.
Maybe you need a stronger sales leader. Maybe you need to improve customer retention. Maybe you need to stop making every decision yourself.
Your action: Identify the top three things your business must accomplish over the next 90 days.
Then decide what you’re willing to stop doing so your team can focus on them.
3. What Could Get in the Way? Anticipate Obstacles to Growth
Every CEO has a plan.
Then something happens.
A major customer leaves. A key executive resigns. Costs increase. The market changes.
You can’t predict every challenge. But you can anticipate what might prevent you from achieving your goals.
Sometimes, the biggest obstacle is the CEO.
I’ve coached founders who built successful companies by making every decision and solving every problem themselves.
That worked when the business was small.
But as the company grew, those same habits became obstacles.
Decisions piled up. The leadership team waited for answers. The business couldn’t move faster than one person.
A great coach helps CEOs recognize patterns and confront what they may not want to see.
Your action: Ask your leadership team to identify the three biggest obstacles standing between your business and its goals.
Then ask:
What am I doing as CEO that could be getting in the way?
Be willing to hear the answer.
4. How Do You Hold Yourself Accountable? Measure What Matters
This is the question that separates good intentions from results.
Salespeople have quotas. Operations leaders have performance targets. Finance teams have budgets.
But who’s holding the CEO accountable?
Who’s asking whether you followed through on the difficult conversation you committed to having?
Who’s challenging you when your priorities keep slipping?
In Built to Win BIG, I explain why accountability is liberation.
When people know what they’re responsible for, when it’s due, and how success will be measured, the entire organization becomes more effective.
That includes the CEO.
Your action: For each of your top three priorities, identify one accountable owner, one measurable outcome, and one deadline.
Review progress every week.
And make sure someone is holding you accountable, too.
How to Put the Four Questions to Work in 60 Minutes
You don’t need a three-day offsite to start applying these questions.
Try this exercise at your next leadership meeting.
Minutes 0–15: What do you want?
Have each leader write down where the company should be in three years. Compare answers and agree on one clear, measurable destination.
Minutes 15–30: What do you have to do?
Identify the three priorities that will have the greatest impact over the next 90 days.
Minutes 30–45: What could get in the way?
Discuss the biggest obstacles, including talent, resources, systems, and leadership. Don’t leave the CEO out of the conversation.
Minutes 45–60: How do you hold yourself accountable?
Assign an owner, measurable target, and deadline to each priority. Schedule weekly reviews and agree on what everyone will accomplish in the next seven days.
Including the CEO.
One hour. Four questions. A clear plan for moving forward.
The value isn’t in having the meeting. It’s in following through on what you commit to.
The Questions Matter. So Does Who’s Asking Them.
There’s something about David Sobel’s conversation with Norm Curtis that has stayed with me.
David had already helped Norm strengthen his sales team and build a more effective sales process.
But that night, he asked a question that went beyond the business.
He asked Norm to think about what he truly wanted from the company he’d spent so much of his life building.
That’s what great coaching looks like.
It’s not always about having the answers.
Sometimes it’s about knowing which question to ask.
In Built to Win BIG, I share stories of CEOs who faced extraordinary challenges, made difficult decisions, and discovered what was possible with the right coach in their corner.
Their stories aren’t just about revenue or profitability.
They’re about becoming better leaders, building stronger teams, and creating businesses that support the lives they want to live.
The four Make BIG Happen questions are a powerful place to start.
But knowing the questions and having someone who will hold you accountable to the answers are two very different things.
Because nobody wins alone.
That’s how you Make BIG Happen.
And that’s how you build a business that’s Built to Win BIG.
Want to discover what happened after David Sobel asked Norm Curtis that question at the Winnipeg Jets game? Read his story in Chapter 11, “Grit That Lasts,” of Built to Win BIG.
Frequently Asked Questions
What are the four questions in the Make BIG Happen methodology?
The four questions are: What do you want? What do you have to do? What could get in the way? And how do you hold yourself accountable? Together, they help CEOs establish a clear vision, identify priorities, anticipate obstacles, and measure progress.
Why is accountability important for CEOs?
Accountability helps CEOs turn strategic goals into consistent execution. Clear ownership, measurable targets, deadlines, and regular reviews keep leadership teams aligned and make it easier to address problems before they become bigger.
How does a CEO coach help a business grow?
A CEO coach challenges assumptions, helps leaders clarify their goals, identifies blind spots, and provides accountability. The right coach helps a CEO make better decisions, develop stronger leadership teams, and stay focused on what matters most.
About Mark Moses
Mark Moses is the Founder and Executive Chairman of CEO Coaching International and the author of Make BIG Happen and Built to Win BIG. He helps CEOs build stronger businesses, become better leaders, and achieve extraordinary results.
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