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CEO Evaluation: Inspiration For Great Conversations

October 28, 2019

Posted in: WATSON Views


It’s time for the CEO debrief and both sides are dreading the conversation – but not for the usual reasons. The CEO is a high performer and no matter what or who is asked, there is rarely any new or developmental feedback. It’s important to celebrate success, but after several years of glowing feedback the process feels stale…

How do you make the most of the conversation, regardless of the situation or feedback? The conversation will look different at different points in the CEO’s tenure and career stage and depending on the nature of the feedback. While different, each conversation can bring unique value – to the board, the CEO, and the organization.

Part 1— CEO Evaluation: Conversations With Real Impact and Part 2 — CEO Evaluation: What Does A Great Conversation Look Like of the Demystifying Debriefs series share guidance on how to structure and design the conversation. In the last part of the series, we focus on how to customize the conversation to you CEO and organization’s unique situation and point in time. These are ideas to get you started. And don’t forget – it’s the CEO’s conversation too, so ask them to come to the discussion with their own questions as well.

Sample Thought Starters… and Situations They are Great for


  • Performance – challenged, mixed, solid, or high?
  • Feedback – is there actionable feedback? Is it new or has it come up before?
  • Career stage and tenure – how long will they be with you? Is this their last intended role? What comes next for them?

Great Questions When:

  • Feedback is not new ❶
  • Feedback is new and there is opportunity for change ❷
  • Leader is close to the end of their tenure ❸
  • Leader is close to the end of their career ❹
  • Leader is so high performing there is little feedback ❺
  • Feedback suggests some challenges or issues ❻
  • Anytime! ❼

  • How are we going to make a change this year, given some of this feedback is not new? ❶❸❻
  • How can the board support you in addressing this feedback? What do you need from us to set you up for success? ❶❷❻❼
  • How can the board support your growth as a leader? ❷❻❼
  • How can we build on and reinforce your strengths? ❹❺❼
  • How can you become an even more impactful leader? ❷❺❼
  • How can you use this feedback to elevate your performance? What can we put in place to support and reinforce this? ❷❻❼
  • How do we build a strong leadership team to carry the organization’s work forward? ❸❹❺❼
  • How do we help you prepare for what’s next while keeping you challenged here? ❸❺
  • How do you plan to action the feedback in the year ahead? ❶❷❸❻
  • How do you plan to grow and develop your team? ❸❹❺❼
  • How do you role model and reinforce our values? Where could this be even stronger? ❸❹❺❼
  • How will you reflect on this feedback and establish a plan to move forward? ❶❷❸❻
  • If a newspaper article came out in a year saying the organization had failed or struggled, in what areas would you expect to find the issues? Where do you think your own (or the organization’s) blind spots would be found? ❹❺❼
  • What are the unleveraged opportunities within the organization? Where are the places where we could look at things completely differently? ❸❹❺❼
  • Where could we do (even) better in terms of efficiency, quality, process, cost, etc.? ❹❺❼
  • What comes next and how do we help set you up for success while keeping you engaged here? ❸❺
  • What could we do more structurally (roles, processes, etc.) to play to your strengths and adapt around your development areas? ❶❷❻
  • What do you aspire to, at this organization and beyond? ❸❺
  • What do you need to help the organization achieve its strategic objectives? What are the barriers? ❸❺
  • What do you want your legacy to be? ❸❹❺❼
  • How do we build a strong leadership team to carry the work forward? ❸❹❺❼
  • What impact would it have on the top team and the organization for you to do things differently as a result of this feedback? ❶❷❻‘
  • What is your feedback for the board? How can we work together more effectively? How can you and your team engage with us to strengthen the board’s performance? ❸❹❺❼
  • What opportunities do you see to strengthen this organization in terms of people, culture, and leadership? ❸❹❺❼
  • What support do you need from the board? ❶❷❻❼
  • What support, learning, or resources do you need? ❶❷❻❼
  • What would the impact be if we could address this feedback this year? ❶❷❸❹❻
  • What would you regret not having accomplished if you retired tomorrow? ❸❹❺❼
  • Where are the places where we could look at things completely differently? ❸❹❺❼
  • Where can you add the most value in the year ahead? What would an amazing year look like? ❷❸❹❼
  • Where do you want to grow from here? ❷❸❺❼
  • How do we help you work through this feedback and strengthen your leadership? ❶❷❻
  • You have much to offer the leaders around you. How can you further support others to grow? What opportunities can we create? ❸❹❺


Flip your context and situation from a challenge to a powerful opportunity to frame the feedback conversation and bring value to the process.