CEO Is Driving You Insane? Ask Madeleine

January 21, 2023 Madeleine Homan Blanchard


Dear Madeleine,

I work for a bioengineering company that was a successful startup. It is now well into its seventh year and we still have our founding CEO. As the fairly new COO, I report directly to him and he is driving me insane. Every time he and the other leaders in the organization meet, we have new conversations but never follow up on past conversations. The agenda for these meetings is never clear, much less sent out in advance so that we can prepare.

I knew working for a founding CEO was going to be a challenge, but I just don’t see how anything is going to get done the way we are operating. Any tips for corralling our CEO?

Trying to Get a Grip


Dear Trying to Get a Grip,

It sounds like your boss fits the classic profile of the entrepreneur CEO: action oriented, risk taking, fast moving, and wildly creative. I grant these kinds of leaders can be maddening for others who are process and detail oriented. Since you are at the executive leadership level, would it be crazy for you to take on organization of leadership team meetings? Obviously you would want to ask your CEO first and get his agreement. He might just be waiting for someone else to take it on.

You could organize the meetings into sections:

  • Old action items, with updates on actions taken and obstacles to be aware of
  • New topics, with clearly stated owner of each topic and desired outcomes
  • News and announcements

This is just off the top of my head, but these are fairly standard. If you feel strongly about having an agenda, you will probably have to put it together yourself. If your CEO has a chief of staff it would be that person’s job, but it doesn’t sound like that is the case. You would have to ask your fellow leaders to give you their agenda items in time for you to put them on the agenda.

Another thing that might help you to gain some clarity on all of the conversations is some distinction for the kind of conversation you are having at a given time. When talking about possibilities, there are three kinds of conversations:

  1. Speculative: When you are brainstorming possibilities or an idea for something you might take on.
  2. Planning and evaluation: When you are attracted to an idea and are now playing it out and poking at what it might look like to execute if you decided it was worthwhile. You are playing devil’s advocate, sharing examples, anticipating obstacles, and evaluating whether a course of action would achieve the desired outcome.
  3. Decision making: You are deciding on a project or course of action and determining whether or not you will go ahead with it. This is where, as a team, you can use a RACI chart to make sure everyone knows (1) who is ultimately responsible for execution and achieving the outcome, (2) who needs to be accountable to that person for specific action items, (3) who needs to be consulted, and (4) who needs to be kept informed. For this conversation, you can flag specific milestone dates to put into that week’s meeting agenda so that the responsible team member can share updates.

I don’t know where these distinctions came from, but I learned them from my husband who is the president of our company and who fits your CEO’s profile. He would throw out ideas only to find out weeks later, to his dismay, that someone had started to execute them. He had to train his leadership and extended leadership team to recognize the difference between speculation conversations, planning and evaluation conversations, and decision making conversations. You might consider sharing these distinctions with your CEO so at any given moment you can ask what kind of conversation you are having.

If you try just these two ideas, I suspect you will feel a little more sane. Your CEO will still be himself, but there will be a bit more discipline in place so that the whole team will feel more grounded.

It sounds like you have your hands full but are in a position to add value and make an impact. Good luck.

Love, Madeleine

About Madeleine

Madeleine Homan Blanchard is a master certified coach, author, speaker, and cofounder of Blanchard Coaching Services. Madeleine’s Advice for the Well Intentioned Manager is a regular Saturday feature for a very select group: well intentioned managers. Leadership is hard—and the more you care, the harder it gets. Join us here each week for insight, resources, and conversation.

Got a question for Madeleine? Email Madeleine and look for your response soon. Please be advised that although she will do her best, Madeleine cannot respond to each letter personally. Letters will be edited for clarity and length.


About the Author

Madeleine Homan Blanchard

Madeleine Homan Blanchard is a Master Certified Coach and cofounder of Blanchard Coaching Services. She is coauthor of Blanchard’s Coaching Essentials training program, and several books including Leverage Your Best, Ditch the Rest, Coaching in Organizations, and Coaching for Leadership.

Follow on Twitter More Content by Madeleine Homan Blanchard
Previous Resource
How to Work with Anybody
How to Work with Anybody

Better knowledge of ourselves and others can turn a potential personality clash into a powerful alliance sa...

Next Resource
Using Temperament to Deepen Work Relationships
Using Temperament to Deepen Work Relationships

Understanding our Essential Motivators can be an important addition to self-awareness skill development say...