Dear Joseph,

I am on the leadership team of an organization that is in the beginning stages of a significant cultural change. In reflecting on the work in front of us, I realized that I do not trust the CEO to lead us through this change. This is a person I like and respect, but it seems to me that she is not focused enough to keep us moving forward. Priorities are unclear and shift frequently, and often the tasks that she takes on are not completed. How can I engage in a conversation that supports greater clarity, focus and alignment—and helps us all work together to traverse this shift successfully?

Signed,
C.E.Uh-Oh.

Dear C.E.Uh-Oh.,

You have the potential of being the best friend your CEO has. I hope you will be. What you’ve said is that 1) you care about and respect your CEO; 2) you have information that might be crucial for her to know if she is to succeed in one of the most important efforts of her career. This is a no-brainer. The only question is, do you care about her and the company more than you care about your own comfort? If what you really want is to contribute to the company, and help someone you like and respect, then here’s how:

1. Test your story. You seem confident about your perspective. Be sure it’s based on solid data and not just your own judgments and preferences. Ask yourself:

• Have others called out similar patterns in her?
• Is this weakness as relevant to the project ahead as you’re making it out to be?
• Are there people with informed opinions who might see her substantially differently?

If your concerns seem well grounded, then . . .

2. Prepare your case. Gathering facts is the homework required for crucial conversations. If you are to be helpful to the CEO, you will need to have enough evidence of two things to persuade her that this is an issue:

• Concrete and compelling examples of the focus and follow-through problems you allege. You will need enough evidence to demonstrate that it is a pervasive pattern not easily explained away.
• A good argument for why these weaknesses will have a damaging effect on the change effort. When you feel you have a strong body of evidence, you must also . . .

3. Prepare a solution. What will you suggest she do? You will be of little help if your implied solution is “Change the basic work style and personality you’ve practiced for decades.” Options might include:

• • Deputize someone with aptitude for this effort.
  • Engage staff support to offset your weakness.
  • Step down in lieu of someone more qualified.

C is an extreme solution—but if it is what you believe is right for the company and for her, make your case. But if A or B could work, bring a proposal for one of those options.

4. Hold the conversation. I suggest the following steps as you engage your boss:

• Ask permission. Let her know you’ve been thinking deeply about the upcoming change project . . . and that you have some concerns. Ask her if it’s okay if you offer some feedback about it. Asking permission helps others feel more emotionally safe.
• Give her a “why.” Create more safety by properly framing your motivation for sharing. “I have some reasons to believe that the effort might fail. I’d like to share those. Of course this is my perspective, and you may disagree. But I’d feel less than loyal to you and to the company if I didn’t offer my view.”
• Offer evidence—if needed. Cut to the chase. Start by letting her know. “I think the most important predictor of success will be consistency and flawless follow-through. Those aren’t always your strengths.” At this point, you may need to share your evidence. If, however, she openly acknowledges these weaknesses, you may not need to prove an admitted fact.
• Invite dialogue. Having made your case, invite her to poke holes in it. “This is how I see it. And I know I could be wrong. I hope, however, you understand my intentions. Do you see this differently?”
• Propose a solution. If she shares your view, offer your solutions.

I wish you the best as you offer a gift of true friendship and loyalty.

Sincerely,
Joseph

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