Haunting Questions

  1. October 20th, 2022  | 

  2. Print This Post
Published in Leadership, Productivity

Planning Season is Scary for Some

Twelve years ago the first edition of That’s A Great Question was published.

During the pandemic, I updated the book, providing more guidance on asking great questions with new chapters: “Asking Questions Isn’t Enough,” “Leading with Questions” and “Getting (and Giving) Great Coaching.” Three categories of questions were added (“Values + Culture,” “Strategy + Problem-Solving” and “Risk”). And five hundred new questions were added, doubling the number of questions from the first edition.

My workshop on this topic is growing in popularity as leaders realize the art and science of asking great questions has typically occurred organically in their organizations rather than being developed intentionally like any other skill.

Last week I was in Charlotte, North Carolina, delivering this workshop at the request of #Vistage Chair Kurt Graves. 

Before the workshop began, Kurt asked each of the chief executives of his two groups to share with their peers their best “go-to” question.

Useful Questions

Kurt’s request was met with enthusiasm, though a few executives admitted that asking questions was not one of their strengths.

Given time to think, however, they each shared a question. Here are ten useful questions to ask—whether it’s of yourself or other people:

  • “Can I look my kid in the eye, explain my decision and feel good?”
  • “If you did know the answer [when someone tells you they don’t], what would it be?”
  • “If you were me, how would you solve this problem?”
  • “How can I help you?”
  • “What am I doing to create what I say I don’t want?”
  • “What’s the problem your business solves?”
  • “What’s the most important thing we should be doing right now?”
  • “How do we make this possible?”
  • “What do you do best?”
  • “Am I pursuing the things in life that give me purpose?”

The Impact of Questions

Halloween is upon us and so is strategic planning season. It’s a scary time for many.

“The greatest danger in the strategic process is the failure to discuss meaty issues that are hindering individual and organizational performance.”

I wrote those words eight years ago in a post entitled “Scary Times.” [October 2014]

I described leading a planning session and asking six company leaders a simple question:

What’s one principle you wished the people in this room practiced more consistently?
It was a scary question for that group because the answers that emerged indicated that trust was absent with one of the executives.
The discussion was awkward. After the session, the CEO told me how uncomfortable he’d been during the discussion. He wondered if the issue could have been handled differently.
Were you aware this situation existed? I asked. Yes, replied the CEO, but I was hoping it would fix itself. How long, I asked, have you known this situation existed? Months, the CEO replied. Then what, I asked, causes you to believe the situation would fix itself without the conversation we had this afternoon? No answer.
Sixty days later, the executive who was the source of the trust issues had been dismissed from the company. Morale rose. Results improved.
The impact of that single question addressed an issue that was undermining morale and hindering performance.
It’s a scenario I observe regularly, watching leaders struggle to tackle head-on difficult issues. It often falls to me to get things moving with a series of questions. During a planning session thirty days ago, I posed this question to a group of company leaders:
What’s the elephant in the room that everyone is thinking about but no one is talking about

An awkward moment ensued before the “elephant” was named, discussed, and dealt with.

The ability of a senior leadership team to handle conflict is predictive of the size of problems the team can address on its way to becoming a high-performance organization. “Facts do not cease to exist,” wrote Aldous Huxley, “because they are ignored.”

If you’re interested in discussing how you and your team can elevate your performance, please email me at greg.bustin@bustin.com to schedule a free consultation.

The only thing scarier than answering pointed questions is not asking them at all.

About the Author: Greg Bustin advises some of the world’s most admired companies and leaders, and he’s dedicated a career to working with CEOs and the leadership teams of hundreds of companies in a range of industries. He’s facilitated more than 250 strategic planning sessions, he’s delivered more than 600 keynotes and workshops on every continent except Antarctica, and he coaches leaders who are inspired to take their career to the next level. His fourth leadership book— Accountability: The Key to Driving a High-Performance Culture (McGraw-Hill) —is a Soundview Executive Best Business Book.

Ready to reset?


Attend my free Accountability webinar: I Did It! to set and achieve your 2021 goals.

REGISTER FOR FREE

  • February 17th from 11 AM – 12:30 PM Central Time
  • My free webinar will help you:
    – Sharpen your personal goals
    – Improve time management
    – Tackle tough work-related issues
    – Support remote workers

Learn More
To dive even deeper into the topic of accountability, I invite you to purchase a copy of my bestselling book, “Accountability: The Key to Driving a High-Performance Culture.”

Get The Book

Become a better leader.


Download my three free e-books.

Greg Bustin

Please enter your information below to access a digital download link for my three free eBooks. Once submitted, you will receive an email with a link to download the eBooks.

Free Tips


Sign up to receive free tips on business, leadership, and life.

Greg Bustin

Please enter your information below to start receiving free tips on business, leadership, and life.

Sign up for my free bimonthly email button