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CEO Evaluation: What Does A Great Conversation Look Like?

October 21, 2019

Posted in: WATSON Views


The meeting is booked, invites are sent, and the CEO evaluation report is in the CEO’s hands. It’s time to draft the agenda and figure out how to meaningfully fill an hour…

Part 1 of the Demystifying Debriefs series answered your burning questions on how to set up the conversation. Now we turn to conversation design – the anatomy of the conversation itself and some tips and questions to guide the way.

Conversation Flow

Every conversation is different. The flow will vary depending on comfort and familiarity with these kinds of conversations, the CEO’s point in their tenure and career, the organization’s context, and the nature of the feedback itself. Regardless of the situation, thoughtful preparation and intentional design are key to a constructive conversation. The conversation flow set out below can act as a starting point – to be tailored to your situation and context.

Top Tips

  • Ensure you have enough time to do it properly
  • Bring a calm, measured demeanor – if you are uncomfortable with the task, they will be too
  • Make sure not to just dive into the critical feedback – speaking about how their strengths can be used more is a powerful conversation
  • When discussing quantitative ratings, focus on the story the data tells – it’s not about the numbers, it’s about the highs and lows and how they align with the CEO’s own perceptions of their performance
  • You don’t have to have all the answers
  • Be open to another perspective, and to receiving feedback
  • Ask curious, open-ended questions – start early in the conversation, to set the tone that this is a dialogue
  • Be conscious of the “judgement rut” – magic question is “what can you (we) learn from this?

Thought Starter Questions

  • What feedback are you most proud of?
  • What feedback was tricky for you to see?
  • Are there any immediate steps, including any communications, that you envision?
  • What are your initial thoughts on how you move forward beyond the immediate?
  • Would you like some of the board’s observations around the key takeaways?
    • Here are the themes of the feedback that show the board what unique value you bring to the organization…
    • Here are some of the areas the board would like you to focus on in the year ahead…
    • Here are a couple of things you might want to do to play to your strengths and develop some of your weaker areas…
  • Do you have any feedback for us or the board?


Get good data though a professional evaluation process, then put it to work with a powerful conversation that deepens the relationship and sets the stage for the year ahead. Stay tuned for Part 3 of the Demystifying Debriefs series.