CEO Is Making A Colossal Mistake—and You’re Holding the Bag? Ask Madeleine

Dear Madeleine,

I am the COO for a medium sized, mostly US-based specialty product business. Our CEO was always the idea guy and I was execution. Our business used to be straightforward, but we recently expanded with services and a couple of storefronts—against my recommendation.

Our CEO is a visionary and expects his executive team to figure things out. I thought we might be okay until I realized our CFO and the person who leads our IT department are completely in over their heads. The CFO has no experience at all with the complexities of offering services, how to get people paid, etc., and our technology guy keeps suggesting new software platforms, none of which seem to work with one another. We are spending more money than we anticipated. I feel like we are in a free fall, but my CEO has no interest in details.

I am at my wits’ end. I can’t possibly solve all our problems by myself. We had a perfectly good business, and I am furious with my CEO for blowing it all up. I told him making these big moves before we had some infrastructure in place was going to be a train wreck, but he becomes less reasonable by the day.

Part of me just wants to throw my hands up and walk away. I would lose equity but the way things are going, it will be a share of not much. The CEO and I were friends but the friendship seems to have gone down the tubes. I’m just not sure any of this can be salvaged. Thoughts?

Free Fall


Dear Free Fall,

Well, you won’t be the first person in history to not be able to stop someone from making colossal mistakes only to end up holding the bag, and you won’t be the last. I am so, so sorry.

I think you already know what you are going to do, Free Fall. What you read next will only confirm it.

There are a few separate issues here. I will list them out and I don’t claim to have the priorities in the right order. Some of these things are more fixable than others.

  1. Your people do not have the skill sets required to lead the new parts of the business. (This can be fixed. Not as quickly as you’d like, but still.)
  2. There was not enough time spent planning and getting the right resources in place to pull off these big plans. (This is blood under the bridge—you can’t change the past.)
  3.  Your CEO seems to have abdicated all responsibility, possibly after having lost his mind. (I suspect this is not something you can influence, since you have already tried.)
  4. The relationship between the two of you seems to be damaged beyond repair (unless, over time, you decide to let bygones be bygones).
  5. It sounds like you have a very lean operation with no other executives to support you. (It is hard to tell from your letter. If there are, in fact, some competent folks who can help, now is the time to call on them.)
  6. Your anger and frustration are clouding your ability to think straight. (This you have control over. The sooner you get hold of yourself, the better.)

Does that sound right?

I think your first job is to find a way to calm down so that you can make your first big decision: Is this worth fighting for or not? Whatever you normally do to calm yourself down will work: meditation, prayer, exercise, listening to opera. Turn off your phone. Take a night off and calm yourself down. Get a decent night’s sleep. Then if, as you have expressed, you are truly on your own here, ask yourself whether you have it in you to tackle this situation and get it turned around. If the answer is a hard no, there you have it.

If you do think you might have it in you, decide exactly what you are willing to do and for how long. The length of time matters; otherwise you will be stuck seeing the whole mess through to either success or failure, and who knows how long that will take. You’ll want to be at your best, and if you are overcome by your anger and frustration, you will need to find a way to park that or let it go.

Accepting the stark reality of the situation is the only way you will see what needs to be done. I am not saying your CEO isn’t to blame for your pain and suffering—I am saying putting a lot of energy into placing blame is not a good use of your time.

You might consider getting your CEO to agree, in writing, to a hefty bonus if you are able to turn things around. That might help you find the motivation to save the day.

Let’s say you put a stake in the ground and decide “Okay, I am going to give this my all for three months.” Then make a list of everything that needs doing. You are smart enough to know most of what needs to be done even if you don’t know how to do it. These things might include:

  • Get help: call on a friend or mentor with business savvy for advice.
  • Hire someone who knows what they are doing, or at the very least a consultant who can work on a contract basis.
  • Make a plan of what to do and in what order.
  • Delay anything that can be delayed.
  • Tackle the big problems first and knock them down, one by one.

If this all makes you feel the kind of despair that makes you want to go to bed for the rest of your life, again you have your answer: either this has gone too far to fix or you just don’t care anymore.

Once you get all the emotion out of the way, it will be much easier to see the full reality and assess your willingness and ability to rise to the challenge.

At this point you are either thinking “I can do this” or “Run, don’t walk away from this mess.”

I wish you clarity, and the courage of your convictions.

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.

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