Dealing with Challenging Conversations
Leaders and managers often face the prospect of having challenging conversations with a team member. It could be about a client problem, performance issues or even a basic “fit.” For many of us, the initial reaction may be one of avoidance, adopting the cognitive bias known as the ostrich effect, or of defensiveness. For others, it is predicated on the need to win. None of these stances offers a good probability for a positive outcome. As JP Morgan CEO Jamie Dimon is fond of saying, problems don’t age well, and emotions, whether defensiveness or aggressiveness, will only prompt similar reactions in the other person. Instead, recognize that a multi-step approach offers the best opportunity to have a constructive encounter.
The first step is to realize that how you start will dictate how it all finishes. “Start” begins with ensuring that the team embodies a high trust culture, one feature of which is regular weekly or bi-weekly meetings between a leader or manager and each team member. Having such meetings promotes the best probability for really understanding the other person, both in the professional as well as personal sense. These encounters make it easier to engage when a problem arises, as opposed to a structure which allows for a single annual evaluation or 360º, punctuated by a meeting whenever a problem arises. If encounters tend to occur only during review time or when there is a problem, they will typically elicit a defensive response in the team member, and conversations can devolve quickly into contesting statements. Assuming your system promotes regular meetings, then prior to each, refamiliarize how the relationship began and how it has developed since the person started and fill in with what you have learned about their personal and professional habits, abilities and interests. Such a start will also be useful when special situations occur.
The second step is to frame the problem or issue in as constructive a manner as possible, according to communications expert Holly Weeks (Failure to Communicate), instead of focusing on giving negative feedback. It is critical to have clarity on the nature of the problem or issue and then to understand the outcome or solution you think best. Is the issue “fixable” in your estimation or not? That is, given all that you know, is there an opportunity for learning and growth and development on the part of the team member, and have you done all that you could in working on that growth? Or is this rather about a need for separation?
The last step involves your attitude as you approach the team member. Beginning from a position of vexation, defensiveness or arrogance can often devolve into debates on circumstance. Instead, adopt a quiet confidence and be curious to learn from the other person. Importantly, exhibit empathy from start to finish, adopting a mode of listening and questioning. Be considerate and not censorious. Rather than “why” questions, which can often put the other person on the defensive, asking “how” questions are often far less threatening to the other person. For example, open by asking “how do you see yourself growing here?” Or, “how do you think your time here is going?” If you believe termination is the best answer, such questions can help to elicit thoughtfulness and can move the conversation toward the person’s strengths that might be more suitable in another position. Then provide options about what the person might consider in taking a new role elsewhere and offer ways you might help.
If it is about dealing with a client problem, also begin by asking them about how things are going and how they feel about their development. Then you might ask , “how do you think this issue occurred?” Or, “Take me through your thought process.” Or, “with the advantage of hindsight, how might you have handled this differently?” Finally, ask “how do you think we can improve on this?” These questions are designed to foster growth and understanding rather than recriminations, especially when done as part of a sequence of regular meetings.
The key to dealing with challenging conversations first involves culture. If there is a high trust culture, then it is all the more important for the leader or manager to approach the person in a constructive way. In my own experience at a firm which had such a culture, we were often advised when dealing with these conversations to be hard on the issue and soft on the person. Approaching in anger or frustration will not only result in a defensive reaction by the person but will also tear at the fabric of the culture, as other team members note the difference between what you proclaim about safety and respect and how you act.
Next, it is about how you choose to frame the interaction. Elect to frame it as positive and leading to a better place. Understand clearly the outcome you prefer, and adopt an attitude of considerateness and empathy. If you choose this approach, more often than not both the other person and you will walk away in a more positive frame of mind.
About the author
Robert B. Seaberg, Ph. D., Visiting Faculty, Spanning a career of forty years in financial services, “Dr. Bob,” as he is known in the industry, began as a financial advisor and then moved into strategic marketing directorships. He has spent nearly two decades with Citi Smith Barney and Morgan Stanley as a Managing Director in charge of Wealth Advisory Solutions. He pioneered the use of regional wealth planning centers, helped develop an industry-leading HNW and UHNW training and designation program for select advisors (Family Wealth Advisor) and established the Philanthropy program.