Question: Reporting to an overconfident boss


We are a multi-national outsourcing firm, and I am the CFO to a key leader who heads the largest industry vertical of clients. He is a 20 year veteran to the company and has held many different roles.

His deep experience in industry and the company cause him to downplay the advice of others and be ill prepared for potential disasters.

One example of the latter would be the loss of a key client account, that recently went bankrupt, that I had warned several months in advance.

While this will be huge hit to our P&L, my bigger concern is how can we learn from this experience. Key team members in support functions- general counsel, HR leader, myself and others are eager to give our best advice... if only our manager would listen.

7 Expert Insights


An executive coach could certainly help, but only if the leader wants to be coached. It doesn’t sound like this leader would be particularly interested in working with a coach.

I think you should frame the challenge not as fixing the leader’s ability to listen, but how you & your peers do a better job influencing the leader.

I recommend an article by my partner Marshall Goldsmith titled: Effectively Influencing Decision-Makers http://www.marshallgoldsmithlibrary.com/docs/articles/Effectively-Influencing-Decision-Makers.doc

Some of the points he makes are:

- Every decision that impacts our lives will be made by the person who has the power to make that decision – not the ‘right’ person, or the ‘smartest’ person, or the ‘best’ person – make peace with this fact

- When presenting ideas to decision makers, realize that it is your responsibility to sell – not their responsibility to buy.

- The effective influencer needs to be a good teacher.  Good teachers realize that communicating knowledge is often a greater challenge than possessing knowledge.

- Realize that powerful people are just as “human” as you are. It is realistic to expect decision makers to be competent; it is unrealistic to expect them to be anything other than normal humans.  Is there anything in the history of the human species that indicates when people achieve high levels of status, power, and money they become completely “wise” and “logical” or a good listener?  

- Successful people love getting ideas aimed at helping them achieve their goals for the future.  They dislike being “proven wrong” because of their mistakes in the past.  By focusing on the future you can concentrate on what can be achieved tomorrow, as opposed to what was not achieved yesterday.


While the situation may be challenging, fear not as solutions do exist. The key is not to change the way he communicates, but may be in altering the way you communicate with him.

Based on the limited information, it may be that if everyone is continually providing advice and he is not listening, the issue has as much to do with how the advice is being delivered as to how he is receiving it. This does not mean you are communicating poorly. It means that there is an issue around perspective, and how situations look to different individuals. Determining how he perceives situations, views situations, and communicates about situations will provide windows into potential ways to message effectively with him.

I would attempt to craft messaging that appears less like advice, and am happy to discuss this with you further.


The lack of collaboration and teamwork you describe is troubling.  Coupled with a huge customer loss, it could be devastating for your company.  It is time for your manager to get some help in the form of an executive coach.  An executive coach can reach places that you and his other key team members will not be able to go.  The coach will be able to help him learn from this failure and (hopefully) modify his leadership behaviors to bring about more positive results.

If you have a difficult time finding an appropriate coach in your area, you might also reach out to Vistage International.  The Vistage program can be found in most major cities and is an excellent source of development for senior executives.

Another suggestion to address the team collaboration issue is to look at Patrick Lencioni's work around The Five Dysfunctions of a Team http://amzn.com/0787960756 The book is a great resource.  In addition to that book, however, the Table Group has developed a workshop that helps teams work through the five dysfunctions.  The workshop begins with an assessment that allows one to identify the team's level of behavior in each of the areas.  The workshop is designed to end with clarity and commitments as to how the team will work together in a productive way.  I have facilitated this workshop for several clients and find it to be very helpful in "clearing the air" and getting the team on the right track.  Please let me know if you would like more details.


One trouble with leaders who won't listen is getting them to hear your concerns about their not listening. A strategy might be careful consideration of this leader's frame of reference. What is he most interested in? What is his communication style? It would seem the best way to engage this leader is to talk about whatever is his top priority. I'd be willing to bet that no matter what is his top priority, this issue represents a threat to his success. Along with perceiving this threat he would probably appreciate a proposed solution crafted by you and your colleagues.

The key might be avoiding a direct "You don't ever listen!" confrontation, but rather "We can create this early warning system that can help us be better prepared next time". Hopefully, the "if you would only listen" part can be left unsaid.


Tough spot, but not unusual.  There are a few approaches, depending on the political climate/culture.

1) Talk with your peers and explore the option of a 'confrontation' meeting - better if scheduled as something informal, a private dinner or lunch together, some pre-meeting coaching re: diplomacy and developing a strategy to broach the topic and surface the issue would likely be helpful;

2) If he has one or more close/trusted advisers you are aware of (within the company or circle of friends/colleagues), gaining their assistance to broach the subject  with him can be effective to bring him to the table with the team productively, but needs to be planned well so no one executive team member is put in a position of shouldering responsibility for the intervention;

3) Get the executive team together to request a one day, facilitated offsite to assess the business, how the leadership team functions as a leadership body and what needs to happen to optimally guide the company successfully forward. The design of the meeting would be based on interviews with executive team members and the consultant/facilitator would serve as diplomat and facilitator - coaching the leader going into the meeting and managing the dialogue so that this issue is put into a larger strategic context (versus being the whole picture/focus). (I've seen the greatest success with this last option). The consultant/facilitator needs to be highly experienced to design/manage this well (experience in strategic planning, leadership development, diplomacy and mediation).  


This is a tough situation for sure. From your description of the problem, it appears that the gentleman or gentlelady may not be as much overconfident as he/she is overbearing and bull-headed, in which case it may take a huge disaster to get the message across.

You did not mention a Board of Directors to whom the CEO reports, is there one? Why are they not taking action to either correct the problem through the company leader or without the leader? In many cases it takes the whole team working together to make changes.

I once worked for a Commanding Officer of a large ship in the Navy, who was much like the leader you describe. It was a tough situation. He eventually met his demise. In the mean time, we just kept working the organization despite his poor leadership. Sometimes that is what one has to do. Eventually, and hopefully, somehow truth will come to light and a change in leadership or leadership behavior will take place.

Keep the quest alive, keep the company vision in focus and keep climbing the hill. You will eventually reach the top.


An interesting and challenging situation.  It appears that  of the 'overconfident boss' is playing the role of expert given his vast experience and clearly not utilizing the remainder of the senior management team to help steer and grow the company.  And what a shame for I have too often witnessed this attitude as being the start of a down turn in business.  

It is safe to imagine that the 'boss' is bothered by the loss of a key client account and especially because you had raised the yellow flag of concern months ago.  And now I see a couple of steps you can take with the boss and for the well-being of the company.
1. Check in to get clarity on what you respective roles are as related to what this person counts on you to provide him for his benefit and that of the company.  My guess is he will verbalize what you see them to be even if that is not how he appears to be operating.

2. Tell him that you feel it is critical to evaluate the things that led up to the loss of this key account as a means of evaluating the system or lack thereof that allowed this to happen ... in order to avoid more such losses.  You see this as the responsibility of senior management and want that involvement.

As indicated, I have seen this elsewhere and provided you can get his buy-in (I mean you as CFO because success and profitability is your concern, focus and responsibility) this is a place that an external coach can play a meaningful role by creating the open and safe environment that will allow clear and non-threatening communication.  It's the time to seriously focus on the situation and not any individual(s).

I will be happy to have further communication with you if desired.