Leadership

How to Hold Your CEO Accountable?

Written by Bahar Sen, Co-Founder | Jan 12, 2026 11:19:12 AM

Dear Bahar

I am in the leadership team of an organization in the early stages of a major transformation, and as I look at the work ahead of us and reflect, I realize that I no longer trust the CEO to lead us through this transformation.

This is a person I like and respect, but I don't feel he is focused enough to tackle this major transformation and keep us moving forward. His priorities are unclear and often change, and the work he needs to do is often not completed. He has behaviors that limit his career and the company's adaptation to the new world. The weaknesses we have known so far are now a threat to the transformation process ahead. First of all, how can I have a conversation with her that will support clarity and focus and help us all work together in this transformation, looking in the same direction?

Signature

CX-Offff

Dear CX-Offff,

you have the potential to be the best friend the CEO could have. I hope you will. The things you said 1) You respect and take care of your CEO 2) You are at the critical point for the CEO to succeed in one of the most important transformations of his or her career. These things are self-evident. The question is, do you care more about the company and its people than your own comfort? If what you really want to do is to contribute to the company and help someone you love and respect, here's what you can do:

  1. Test your story. You seem to be confident about your point of view. Make sure it is based on hard data, not just your judgments and preferences. Ask yourself the following:
  • Have other people noted similar patterns in her?
  • Are these weaknesses relevant to the success of the transformation process you are talking about?
  • Are there people who see it completely differently from the way you describe it and have valid and consistent information on these points? (Test Different Perspectives)

If there is a basis for your concerns, then...

  1. Prepare your case. Gathering the facts is the homework required in critical conversations. If you are going to help the CEO, you need to have enough evidence of two things to convince him that this is a problem:
  • Concrete and convincing examples of the clarity, focus and follow-through problems you claim. You need to have enough evidence to show that this view is pervasive in your organization and cannot be easily covered up.
  • Have a strong argument for why these weaknesses will have a detrimental effect in the transformation effort, and make sure that what you say is factual. If you feel you have strong evidence, you should also
  1. Prepare a solution. What are you going to advise him to do? If your implicit solution is "Change your basic way of working and change the personality you have had for decades" you will not be very helpful. Some of the options could be:
    • Appointing a competent person as his/her proxy who can support and represent him/her in matters where he/she is weak
    • Engaging the person or people who will support him/her to compensate for the areas limiting his/her career
    • Suggesting to leave the position for a more qualified person to take over

The third one may seem like an extreme suggestion - but if you really believe it is the right thing for the company and for him, present your case. But if the first or the second works for you, offer your suggestion for one of these options.

  1. Have the conversation. I suggest the following steps to follow when communicating with your boss:
  • Ask for permission. Let him/her know that you have been thinking deeply about the upcoming transformation project... and that you have some concerns about it. Ask if it would be okay for him/her to give some feedback about it. Asking for permission makes other people feel emotionally safer.
  • Give her a "why". Make the environment safer by properly framing her motivation for sharing. "I have some reasons to think that this transformation will fail. I would like to share them. Of course, this is my point of view and you may disagree. But I would feel less loyal to the company and to you if I didn't offer my opinion".
  • Provide evidence - if necessary. Get to the point. "I think the most important predictor of success is consistency and an uninterrupted follow-up. This is not always your strongest suit", start by letting her know. At this point, you may need to share your evidence. But if he openly acknowledges these weaknesses, you may not need to prove an accepted fact.
  • Invite dialogue. After presenting your case, invite him to examine the gaps. "This is how I see it. And I know I could be wrong. Nevertheless, I hope you understand my original intention. Do you see it differently?"
  • Offer solutions. If he agrees with your point of view, offer your solutions.

As Lao Tzu said, " Make friends who tell you your flaws. Beware, only those who tell you your flaws...''

I send you my best wishes for presenting the gift of true friendship and loyalty to your manager.

Love
Spring