25 Questions to Ask a Guest Speaker about Leadership

When you book a top leadership speaker such as Carey Lorenz or Trent Shelton for your event, time is precious. You booked your keynote speaker for their proven knowledge and experience in enhancing growth and development, but you only have their ear for a short time. And while there may be no such thing as a dumb question, you do want to come prepared.

Great questions to ask your leadership speaker are not overly broad or specific. Vague questions may lead to stock answers and even platitudes. At the same time, overly-specific questions that apply to a narrow situation will lack meaningful takeaways for both you and your audience. You want to ask your professional speaker and successful businessperson questions that will provide lasting value over multiple situations.

Here we have provided 25 questions to consider asking your executive coach or leadership speaker to challenge them and get the most from your time.

Leadership style

While no two leadership styles are quite the same, accomplished leaders have faced similar issues. From real estate mogul Grant Cardone to Tomcat fighter pilot Lohrenz, many successful leaders have developed their leadership styles under high pressure. Take advantage of that knowledge by asking:

1. How has your leadership style evolved over time and why?
2. What attributes most helped you become a successful leader, and what do you look for in others?
3. How do you balance inspiring teams to innovate while also maintaining order and the need for standard procedures?
4. Please name a current leader that you admire. What about their leadership style do you like most?
5. What is your overall philosophy of leadership, and what are its overarching benefits?

Leadership lessons for building a positive corporate culture

Successful leaders surround themselves with others who share their vision of success. Steve Jobs and Steve Wozniak had little in common, but they shared a dream for Apple. But as a company grows, it becomes more complicated. Additional staff and, in fact, entire corporate divisions present challenges to maintaining a unified corporate vision. The best leadership speakers have met the challenges and built excellence. While you have their attention, consider asking them:

1. What advice do you have to balance building a positive internal culture while also remaining 100% client-focused?
2. How do you handle a situation where someone serves as a valuable company asset, but also displays a negative attitude around others?
3. What have you found to be the most useful tools or methods in helping teams and cross-teams bond?
4. What methods or processes have you used to make every employee at any level feel that they are part of the same corporate team?

Communications and conflict resolution

If you face internal strife that holds back company growth, odds are it involves cross-team communications meltdowns. Sometimes, actual conflicts arise among staff and management and across teams. Too much of your valuable time may be spent putting out fires rather than doing what you do best—meeting consumer demand and growing the company. Step back and think broadly. Questions to consider asking your booked leadership speaker may include:

1. What steps do you take when a team leader consistently performs at or above your expectations, but several of their staff find them difficult to work with?
2. What has been your most difficult situation where separate but interdependent teams communicated poorly, and how did you resolve it?
3. Marketing and product development [or others pertinent to your situation] can have very different understandings of objectives. What has worked best for you to improve cross-team cohesion and communication?
4. Companies sometimes need to pivot. How do you communicate transformational change so that every employee understands their value in meeting new goals?

Evaluating your team and addressing low performance

Every level of leadership demands performance evaluations. They may occur formally every month, six months or each year. Payment compensation or promotions may depend on them. And while employee reviews are stressful for your staff, they are stressful for you, too. After all, you want to make the most of the situation to grow your company and encourage employees with potential. Sometimes, low-performing workers present a particular challenge. Learn what you can from your leadership coach or speaker by asking:

1. What questions have you found most valuable in a one-on-one performance review?
2. When an employee who has proven valuable in the past appears to underperform, how soon do you act and what actions do you take?
3. Please tell us about a time you had to let an employee go due to poor performance. What first steps did you take, and would you address the situation differently in retrospect?
4. Tell us about a time you were faced with a talented employee intending to leave the company, but you managed to pull them back as a valuable asset. What worked best?

Setting goals and following through

Company goals aren’t a company wish list. They are reasonable, actionable expectations within a timeline. When new data presents itself, goals may even change—sometimes drastically. Experienced leadership speakers have been through it. Take advantage of their leadership experience in keeping teams on the same page by inviting feedback with questions such as:

1. What advice do you have for keeping multiple teams on the same deadline schedule?
2. When a new opportunity presents itself, how have you best rallied your team around meeting new goals?
3. When is it important to communicate new goals throughout every level of the company, and how do you communicate them?
4. Tell us about a time you found a particular manager or team not meeting their goals, and how did you get them back on track?

Leadership lessons in developing resilience and facing setbacks

Even with well-aligned goals, a cohesive team and the best planning, we all face setbacks—both individually and as a company. The strongest leaders aren’t the ones who never failed, but those who failed and came through stronger. Your leadership coach or speaker has assuredly experienced setbacks, yet they worked through them. They became stronger. Learn from their experience in overcoming personal and professional setbacks by asking:

1. Please tell us about a time you failed to meet an important goal or objective. What initial steps did you take from there?
2. What procedures or company programs have you found most effective in helping associates build optimism and resilience?
3. When you or a team member takes a calculated risk that fails in its objectives, what are your next steps?
4. Was there ever a time when a major project appeared at the brink of collapse, and how did you lead your team through it?

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