I was recently interviewed by a person writing an article on coaching and they posed this question to me: “Who is the most difficult person you have ever had to coach?” Great question. There have been some difficult ones.

– There was the plant manager who ran his organization as a dictatorship. He was sure that none of the problems were his fault, and that if only his subordinates would listen to him and do exactly what he told them to do then the organization would start reaching its potential. Whenever we would broach the subject of how he might be creating some of these challenges he would instantly clam up, change the subject, or conveniently remember a meeting he had to get to.

– There was the senior leader of a defense firm that was a victim of “management’s” incompetence. “They” were the problem, “they” were the reason she was struggling. It was always someone else’s fault, including her coach for bringing up the idea that she might also be playing her part.

There were several other difficult coaching clients, all of whom challenged me as a coach and put my skills to the test; but they all pale in comparison to the single most difficult coaching client I have ever had. Here are some of his difficulties:

– He was extremely opinionated. Some of these offerings were actually in his area of expertise, though most were just opinions, not grounded in fact or experience. Take social media. This guy stated one time that he would never use social media because, as he put it, “It is a waste of time, I do not know of a single client that uses it, plus I do not want to be one of those people who tweets about what I am eating at Starbucks.”

– He was sometimes both lazy and over-committed. This coachee would talk a good game. He would make bold declarations about what he would do as a business leader and what the next steps were for business success. He would commit to certain sales goals, only to see them not be met, usually by a lack of focus or effort, then come up with powerful excuses – and I am sure he believed them himself.

– He was often very moody. Now if you had asked him? He would have said he was just sharing his reality at the time, being open, and that usually he sees himself as very positive. He would admit that at times he was in a bad mood, but in his eyes the moods were usually justified and they blew over with time.

– He was unwilling to face some of his blind spots. Whether it was his attention to detail, or the need to have a difficult conversation with a client. His usual brush off was something along the lines of, “Oh, that’s not a big deal,” or my favorite, “Whatever.”

This coachee fortunately has been a long-term client and I feel I can say that over time he has actually changed for the better. As he has learned to let go of his assessments of how the world should be and instead focused on what he can control, he has started to become a better observer of himself and others. He has started to explore his use of language when making requests and when seeking effective conversations with his clients. This has brought greater productivity. He has become aware of how his moods and emotions influence how he is perceiving the world and how changing that view can lead to a change in outcomes. This coachee is still a work in progress — but he is less and less my most difficult client.

You might have guessed who this person is by now.

It’s me.

This is the challenge all leaders face: the most difficult person you will ever have to lead is yourself. The more you are coachable, the more you are willing to become the person you would like to see in others, the more time you can spend transferring those insights and skills to your followers. Today is always a good day to start. As for me, I want to go jump on social media and have some powerful conversations.

About Croft Edwards

Croft Edwards, MCC, leadership coach and speaker, is a thought leader in the field of leadership and organizational change. He is the President of CROFT + Company, a global leadership and organizational change firm with clients spanning the spectrum from oil companies and manufacturing firms, to government entities and non-profits, to small businesses and start-ups. He has coached hundreds of leaders at all levels of organizations from front-line supervisors to CEOs and Social Entrepreneurs. His speciality is the study of LeadershipFlow, the melding of the emerging study of Flow with the field of Ontological Coaching which looks at how leaders show up in their use of language, moods and emotions and the body. Croft is also a retired Army officer with a decorated career as a command and staff officer in the United States Army, both active and reserve.


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