How to Discuss the Undiscussable

Claire, the Chief Operational Officer (COO) for Master Investments, was facing a dilemma. She was responsible for all operational aspect of the hedge fund. As the founder and portfolio manager John Master told her, “You run the firm, and I focus on the investments.” One of Claire’s direct reports was Lewis, the firm’s manager of information technology (IT). Lewis was a weak performer, and despite Claire’s constructive feedback and mentoring, he was unable to improve. It was time to replace Lewis and hire a new IT manager who would be able to fill the role effectively.

The problem was that John and Lewis were old college buddies, and John had personally made the decision to hire him. Claire felt extremely uncomfortable complaining to her boss about his close friend, and worried about the repercussions. At the same time, she felt uncomfortable remaining silent, and indeed felt that out of loyalty to John she had to speak up. Hence her dilemma.

When you need to raise a difficult topic, here are some tips:

Tip #1: Acknowledge that this is a difficult topic to raise. While the uncomfortable context may be obvious, explicitly naming it can help everyone relax a bit and get through the conversation with less stress.

Example: John, I need to talk to you about Lewis. I know he is your close friend, which makes this a difficult topic to bring up. Forgive me if this doesn’t come out right, and know that I am doing my best to discuss this openly and honestly.

Tip #2: Don’t beat around the bush – state your concern right up front. Given the stressful nature of the topic, many people resort to long introductions or evasions that only serve to confuse their counterpart and waste time. This often makes an already difficult conversation even more difficult. Instead, describe the topic with an opening sentence or two that tells your counterpart exactly where you are going.

Example: I am very concerned about Lewis’ performance, and I think we may need to talk about replacing him. It’s not something I raise lightly, and I want to discuss it. I know he is your friend, so I am sure you will have strong reactions of your own. Nevertheless, I have a lot of information about his performance that I need to share with you so you can understand where I am coming from.

Tip #3: Don’t rush. This is the flip side of the previous advice. Once you have shared the essence of what you plan to discuss and the uncomfortable topic is out in the open, resist the urge to quickly state everything you can to make your case. Slow down, and make sure to monitor your counterpart’s reaction, inviting their input along the way.

Example: I have seen Lewis make several serious mistakes that could jeopardize the fund. We’ve been lucky so far, but I feel it only a matter of time before something goes seriously wrong. I am happy to share some examples with you of what I mean. How would you like to proceed?

In the end, difficult topics will always be hard to discuss. You can do everything right, and the other person will still have a strong negative reaction. Keep in mind that the initial reaction is not necessarily the other side’s ultimate decision on the topic. Once you’ve opened up a dialogue, be patient and recognize that it might take more than one conversation to get through the issue.

Good luck!