25 Great Questions Every CEO Needs To Know How To Answer

by Cheryl Powers

Lead, follow or get out of the way. That’s the sentiment I grew up with. My dad was a naval officer in WWII who served at the same time as Ronald Reagan was in the US Army. And my dad knew how to steer a ship. He was kind, consistent, and competent and he taught me a great deal about leadership.

Unfortunately, in today’s business climate I see far too many leaders turning over the helm to employees who haven’t a clue about leadership, budgets, revenue, selling, or management. Unless, of course, you consider how well the employees manage their bosses or how they manage to consistently underperform.

Why this lack of leadership now? Now, more than ever, companies need their leaders to be smart, strong, decisive, out in front. Today’s leaders need to be fearless in managing their businesses and their people. They need to be able to make decisions and get their employees to rally behind those decisions. They need to take massive daily action toward the company’s goals. Today’s leaders and managers must develop the skills necessary to recruit, hire, train, manage, coach, debrief, and partner with their employees in service of increased revenue, customer engagement, and innovation.

Most CEOs I meet with have no idea just how many opportunities they are leaving on the table by forfeiting their duty to set a bold vision, over communicate the details of the mission, and demand accountability to the subset of goals and targets that must be systematically achieved to make the vision a reality. For most, the opportunity can be measured dollars (usually in the range of multi-millions of dollars) and in respect (as in losing the respect of those who matter) from team members, shareholders, and customers.

The funny thing is that when we perform the analysis (request a sample here), calculate the numbers and they see in bold print how much they are losing, it’s as if they knew it in their gut all along but didn’t have a way to address it or approach it. Now that they see the path we have laid out to fix the problems that are keeping them from growing faster or more profitably, most want to right the ship. But wanting it is only a fraction of what it will take to make it happen.

“It’s going to be painful,” I tell them. “It’s going to take hard work, determination, and real accountability. If you’re not willing to do what it takes, let's not move forward together.” There simply is no point in paying us to help you start a job you're not prepared to finish.

Vision takes courage. Execution takes guts. Results take Leadership.

“It’s going to be painful,” I tell them. “It’s going to take hard work, determination, and real accountability. If you’re not willing to do what it takes, let's not move forward together.” There simply is no point in paying us to help you start a job you're not prepared to finish.

These are tough words to hear. They are tough to say but they need to be said. Leading change means taking personal responsibility for making it happen. It means implementing real accountability throughout the company with consequences for inaction. Let’s face it, many companies are like badly behaving teenagers. Chronic bad behavior has its roots in the chronic abdication of responsibility, which fosters a sense of entitlement and breeds a culture of drama and underachievement.

You can fix this. The first part of the solution is taking radical personal responsibility for your part in creating it in the first place and allowing it to be there. If you can have the tough conversation with yourself, forgive yourself completely for not knowing or doing better, and solemnly promise to do better now that you know better then you will be able to have the same tough conversations with your leadership team. You will also be modeling the type of conversations you will expect them to have with their teams going forward.

While some of your people simply will not be able or willing to make the changes necessary, many of them can and will turn their performance around when you provide the help they need and begin to hold them accountable to high performance. And there are high achievers in the workforce looking to go to work for serious leaders who are doing something worthwhile. Great people want to do great things. They want to excel. They want to follow greatness.

As for the underachievers, redeploy them to more suitable roles or as my dad would say, ship them out. I told you it was going to be tough but keeping chronic under-performers is not the answer --- for you or for them. Keeping them in a role that they are not suited for compromises the mission and the integrity of all involved.

Michelangelo said, "the greatest danger for most of us is not that our aim is too high and we miss it, but that it is too low and we reach it."

Here are some important questions you should be asking. There are many more but these 25 will get you started.

  1. How aligned are your leaders around your core mission?

  2. What execution skills are lacking in your core management team?

  3. Is your pipeline as robust and as full as it should be? Is your pipeline management system useful, effective, milestone-centric, and legacy?

  4. Are all of your salespeople capable of selling enough to help you reach goal and grow your company profitably?

  5. Who can sell more than they are now?

  6. Who will? And - Who wants to sell more but can’t because they don’t have the skills?

  7. Can any of your salespeople be performing 2X, 3X, 4X, or 10X better than they are now?

  8. What specific weaknesses are keeping your salespeople from reaching their full potential?

  9. How much do you and your sales managers regularly discount sales forecasts?

  10. How much does a sales call cost you?

  11. How much does an underperformed cost you?

  12. How aligned is your team around your value proposition?

  13. How effective are your managers at driving high performance?

  14. How effective are your managers at coaching and developing underachievers?

  15. What is the current growth potential of each individual contributor?

  16. What is the growth potential of the entire team?

  17. What is the current state of your managers' skills?

  18. What will it take to increase those skills to the level it needs to be?

  19. What has to change before your salespeople consistently sell at higher margins?

  20. Do you have the right people, the right managers in the right seats?

  21. What is your current action plan to improve revenue performance?

  22. Are you spending resources training the wrong people?

  23. Are you spending resources training the wrong things?

  24. How much time and money does it take to get a new producer in place when you lose one?

  25. If your top salesperson resigned today, what steps would you take to replace the revenue?


26. Are you ready to pull back the blindfold and get some real answers and a plan of action?

There’s a BIG payoff for winning the battle. You get to keep part of the winnings and you’ll feel great about yourself. And I’ll be here to help you every step of the way.

I'd love to hear your thoughts on growing revenue through leadership. Please leave your comments below or contact me directly at [email protected].

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