How To Handle Difficult Leadership Team Members

As unfortunate as it might sound, there seems to be at least one difficult member on most leadership teams. We all know the profile—they struggle to collaborate, feel like they are always right, and dismiss others’ perspectives. In fact, there has been quite a bit written about dealing with difficult people at work. While I agree with much of it, I think the solutions often are a bit simplistic.

Of course, toxic executives who are unethical or demeaning to others have no place in any organization and as challenging as it might be they should be counseled out. However, solutions aren’t quite as straightforward when dealing with high performing, talented senior leaders who frequently display difficult behaviors. I recognize that this notion goes against current conventional wisdom, but the reality is that superior senior leadership talent and expertise is worth a great deal to any organization and can sometimes outweigh the pattern of difficult behaviors individuals might exhibit. I am not suggesting that bad behaviors should not be dealt with, but I am submitting that ‘just fire him’ or ‘demote her’ are much easier to say than to do. This is especially true when the senior leaders in question are effective technicians such as a CFO who is masterful at shaping high value acquisitions or a CMO who has led the development of products that set her organization apart.

To bring the challenge to life let me provide a real-life example pulled from our client experience. Charlie is an extremely talented and well-regarded CFO in the government contracting industry with 30+ years of experience. He was the orchestrator of several successful sales to large industry players and when I met him, he was working with another young CEO, Tanya, to help position her company for acquisition. Tanya looked far and wide to find someone with Charlie’s capabilities and track record and was very pleased with his financial engineering efforts. Unfortunately, Charlie became a pariah to his colleagues on the leadership team. They appreciated his experience but were put off by his dismissive “been there, done that” approach to almost every conversation.

Comments like the following were commonplace: “I’ve been doing this for over 30 years, and I know without a doubt that what you are suggesting won’t work.” Charlie also wanted to be included in the decision making of every facet of the organization but was quite proprietary when it came to his own area. Team members confronted Tanya and suggested that Charlie “had to go” or the company would start to lose other senior leaders and employees. Given that Charlie’s abrasive style was counter to her own, Tanya agreed that some action needed to be taken but was she concerned about setting back the progress that had been made to get the company in strong financial shape.

Tanya engaged me to help repair her increasingly dysfunctional leadership team. While certainly not the only challenge the team was facing, Charlie was the biggest elephant in the room so the balance of this article will focus on the actions Tanya and her team took to address a difficult teammate.

Like all good consultants I started by interviewing the members of the leadership team as well as Charlie’s direct reports. Tanya was frustrated that the team couldn’t see the incredible value that Charlie was bringing to the organization. “Sure, he can be abrasive at times, but they just don’t seem to see the big picture.” A few teammates seemed to recognize the value but struggled to see how the CEO could let Charlie behave so poorly. “I know he’s done a great job positioning us for sale for which we will all benefit greatly but we have also played a big part in the company’s success, and he often makes our job much harder than they should be.”

The bulk of the team had little to no appreciation for Charlie’s ‘so-called value.’ “We certainly can find another capable CFO who is better to work with and who cares about the contributions and perspectives of his colleagues.” Charlie’s direct reports were torn as they too felt the dismissive ‘my way is best’ air but they also witnessed Charlie’s amazing talent first-hand. “While he can be very difficult to work for, I have learned more from him than any other person I have ever worked for.” When I finally spoke with Charlie, he suggested that he thought the team worked pretty well together but people got their feelings hurt too easy and spent too much time on trivial issues. “When I am asked my opinion, I give it and sometimes people don’t like that I am direct and don’t agree with them.”

As I debriefed the highlights of the interviews with Tanya, it became quite clear to both of us what actions needed to be taken.

1. Action One – Coaching. Given that Charlie’s behavior was clearly holding the team back, Tanya met first with Charlie to discuss the challenge and help him think through how to strengthen relationships with his teammates. It wasn’t a surprise to Charlie how his colleagues felt about him, but he was a bit alarmed by Tanya’s level of concern about the harm it was causing the team. “Your behavior is shutting down important dialogue, putting a rift between finance and other departments, and generally sapping the energy of the team.” Charlie was a bit defensive at first but given Tanya’s direct but supportive approach, he finally admitted that he could do better. With Tanya’s coaching he agreed to reach out to his colleagues to let them know he was committed to being a better teammate. “I commit to listening to your perspective and regardless of my opinion I will speak with you with the respect and courtesy you deserve.” These discussions were very helpful in preparing for the team level discussions associated with action two.

2. Action Two – Assumptions & Expectations. While Charlie’s behavior clearly needed to be addressed, Tanya wanted to highlight that the entire team including her had some work to do. She started the next leadership team meeting by revealing that she sometimes unfairly categorizes colleagues who have much different styles and approaches than she does as difficult. “I am pretty reflective and need a bit of time to think through challenges before reacting or committing and when I encounter others who think out loud and make quick decisions, I sometimes falsely assume they are arrogant and rash.” She challenged the team to reflect on the assumptions they might be making about teammates that could be inaccurate. “We might be right but there is a good chance that our assumptions might be wrong or at least partially wrong which is a lost opportunity.”

Tanya then turned to the team’s operating principles—the expectations for how they agreed to work together as a team. She placed particular emphasis on two of the principles: respect and listening. For the first—we commit to treating each other with respect—Tanya emphasized that she would not tolerate disrespectful behavior from anyone. She underscored that while each team member is a bit different and each does things that annoy others sometimes—talk too much, get distracted easily, ask too many questions—there this is no reason to lash out, ignore or disparage colleagues. “We have too many important things to deal with every day as an organization to let disrespect get in the way.” She acknowledged that she had tolerated disrespectful behavior from some of in the past and committed to holding everyone accountable in the future.

For the second principle—we commit to listen and consider each other’s perspectives—she made it clear that while Charlie’s delivery needed to improve, each team member also needed to do a better job truly listening and seeking to understand views that are counter to their own. “Sometimes we need to have a thicker skin and work hard to get beyond how something is being delivered and consider what is being said. This sense of curiosity will make us and all our employees better.” Tanya finished by reiterating that it was up to each team member to live by these operating principles and to acknowledge when we flounder and lift each other up.

3. Action Three – Accountability. Tanya recognized right from the start that Charlie’s work to become a better teammate would not be easy. Not only had she let him get away with poor behavior for quite some time, but she also realized that he had likely be operating with this style and approach for most of his career. She committed to being a sounding board for Charlie to think through how to engage more productively and respectfully and was also quite clear that she would be watching and would call him out directly when she saw him fall. “I value your contribution immensely, but I will not let you or anyone else detract from the important work we do together as a team.” Tanya also encouraged teammates to address challenges directly with each other but indicated that she was more than happy to get involved when authentic efforts were at a stalemate.

This is what great leaders do. They gain agreement on expectations (in this case behavioral expectations); do their part to live by the expectations; and hold each other accountable.