Five Questions Guaranteed to Make a Lasting Impression on Your CEO
As the saying goes, "knowledge is power." And when it comes to your CEO, there's no better way to gain that knowledge than by asking the right questions.
In today's fast-paced business world, understanding your CEO's vision is crucial to your team's success. That's why we've compiled a list of five questions guaranteed to leave a lasting impression on your CEO and help you seek advice for your future. By asking the right questions, you gain valuable insights into the company's objectives, values, and challenges and position yourself and your team for success. So, grab a pen and paper, and let's get started.
You can use these questions during Town Halls, Ask-Me-Anything events (AMAs), or one-on-one meetings. These questions can also be asked of any executive, business leader, or subject matter expert, as many of these individuals think like or are on the path to becoming the coveted CEO professional.
"Asking the right questions takes as much skill as giving the right answers."
--Robert Half, CEO of Global Human Resource Consulting Firm
Our Five Questions Guaranteed to Make a Lasting Impression on Your CEO:
How do you hope to change, transform, or disrupt our industry?
Of our competitors, which CEO or company head do you respect the most and why?
What is the best advice someone has given you, and why was it so helpful?
What is something you wish you had known before becoming CEO?
Was becoming a CEO always part of your career plan, and if so, at what point did you decide to pursue it, and how did you know you were ready?
5 Questions to Ask Your CEO
How do you hope to change, transform, or disrupt our industry?
Understanding how your CEO sees the industry developing is essential if you want to understand their vision and find your place in it. One way to do that is by asking how they hope to change, transform, or disrupt the industry.
This question conveys your interest in your CEO's vision. But, most importantly, it gives you a glimpse into how their minds work and think. Thinking like your boss helps you make better, thoughtful decisions and convey the company's objectives more meaningfully to your teams.
By asking this question, you open the conversation to discuss new ideas and opportunities for growth. You can learn about potential market shifts, emerging technologies, or innovative business models your CEO sees as potential game-changers. This knowledge can help set up your team for future success in the sector.
The question also communicates your commitment to staying ahead of the curve and anticipating change. You can better position yourself to make informed decisions and adjust your strategy by arming yourself with knowledge about potential industry changes.
Read our article: 5 Benefits of a Bold Vision for Your Organization.
Of our competitors, which CEO or company head do you respect the most and why?
You can learn a lot about the traits and principles your CEO believes are necessary for success in the industry by asking them if they admire the CEO of a competitor. It shows that you are interested in learning from others and open to new ideas, but, most importantly, you don’t underestimate or plan to ignore your rivals in the space. By understanding what your CEO values in a competitor, you can incorporate those qualities into your work and approach.
This simple question is compelling whether you're trying to get ahead at work, anticipate potential disruptions to your objectives and priorities, start a new business venture, or better understand the industry.
For example, the CEO of a start-up might admire their competitor's innovative problem-solving approaches. On the other hand, the CEO of a retail chain may be impressed by a rival's talent for creating customer loyalty programs. Either way, delving into what your CEO looks for in a competition, you can use this information to your advantage and employ similar tactics or strategies to help you achieve comparable levels of success.
Utilizing the experience and insights of respected players in the industry can be a great way to set yourself apart from your peers. So remember to underestimate the power of understanding what your CEO admires in the competition. These insights can be invaluable in helping you reach the next level in your career and influencing others.
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What is the best advice someone has given you, and why was it so helpful?
Often, the most straightforward and crucial advice makes the most significant impact. As business leaders, CEOs have much information and resources to draw from and benefit from being around like-minded, talented professionals. As a result, the answers to this question can provide valuable insight into their decisions, industry outlook, and how they approach personal and professional development.
Examples of the best advice a CEO has received…
"The best piece of advice ever imparted to me comes from my mom, who is fond of saying, 'What you say matters less than what people hear and understand.' As a teacher, she was a brilliant listener, and she used what she heard to build a bridge between what she needed to teach and how the student needed to learn. From that, she taught me to focus my efforts on helping people understand rather than on what I wanted to tell them. She taught me how to hear, and it is the single most important skill in my professional success."
--Courtney Buechert, founder and CEO of creative marketing agency Eleven, Inc.
“He said successful people bring energy into the room. They don’t suck air out of it. They don’t dominate the room and they don’t negatively impact the group. I thought that was really good advice and a great skill to have.”
Carilion Clinic CEO Nancy Howell Agee considers two distinct but related thoughts among the most personally influential she has received. “The best advice is to say yes to the opportunities, lean in, raise your hand. And there’s a difference between doing what’s easy and doing the right thing. Sometimes the right things are hard.”
Asking this question can be a great way to get to know your CEO better, learn from their experience and create a more robust company culture. It also encourages accountability and transparency, which catalyzes positive organizational change. Being on the receiving end of the best advice your CEO has received can be a guiding light to a successful and opportunistic career path.
What is something you wish you had known before becoming CEO?
To gain critical insight into your CEO's approach to their role, you must inquire about the qualities required for effective leadership and what they wish they had known before taking on such an important position. In addition, understanding the rates that they hold in high regard can help you develop your leadership skills and strategies. In large organizations, people with leadership positions frequently need a skill or capability that they may have undervalued or underdeveloped earlier in their careers.
Examples of CEOs reflecting on what they wish they had known…
"As an entrepreneur, taking risks is extremely important but it is the resilience and perseverance in the face of adversity that really counts. It is important to take risks and learn to be comfortable with being uncomfortable as you persevere in the face of adversity."
"When I left Salesforce to launch Zuora, I figured I could rinse and repeat what worked before to produce the same results. The reality was much different, and I quickly learned that success comes from learning in specific situations, not blindly repeating the past. The key to avoiding sophomore entrepreneur syndrome is remembering to bring out a blank sheet of paper for everything, building for each specific moment in time and each individual customer."
By uncovering what skills, wisdom, or perspectives they wish they had, you can act proactively and add them to your development plan. You can also better coach your employees, especially those who want to pursue more senior leadership opportunities.
Once you have asked them about these skills and gained their perspective, it's important to ask a follow-up question that can provide even deeper insights. For example, "What is the most important skill for a CEO to have?" Aspiring leaders making career plans can benefit significantly from the answer to this question. It can help you avoid potential pitfalls, understand the importance of specific skills, and better understand what it takes to excel in a leadership role. So, as you listen to their response, consider applying their insights to your life and work.
Was becoming a CEO always part of your career plan, and if so, at what point did you decide to pursue it, and how did you know you were ready?
Whether becoming a CEO was always part of their career plan can shed light on a CEO's path and vision for their future. So as you listen to your CEO's response, please pay close attention to the turning points and skills they honed to be where they are today. Did they set their sights on the CEO role early, or did it come about unexpectedly? What made them realize they were ready to lead a company?
By understanding your CEO's journey, you can gain valuable insights into the qualities and skills necessary for success. For example, they may have taken on various roles, learned from each experience, or pursued advanced education to gain the expertise required to lead their organization. They may have also leaped into a new sector or changed their job type, sparking a new, unexpected journey. This new understanding can help you see possibilities and pathways you may have yet to consider.
Asking this question can also help you identify potential areas for growth in your career path by seeing how your CEO navigated their professional journey. Ultimately, the discussion is your opportunity to learn from someone who’s “walked the path” and risen to the top of their field. In addition, it can offer valuable advice to those looking to follow in their footsteps.
In conclusion
Using the five questions outlined in this article, you can better understand your CEO's goals and aspirations, the company's values and challenges, and position yourself for success. You’ll also become a better coach and mentor to those who want to lead and disrupt.
Read our article: Six thoughtful questions for your next 1-on-1
Follow @designACE.ca on Instagram to discover solutions for remote & hybrid team engagement. #NewWaysOfWorking
