Managing Difficult Conversations

There are all types of difficult conversations, but we’re going to focus on five key levels. The first level is awkward conversations. Awkward conversations can include a friend having their fly down or a colleague having lettuce in their teeth before a big presentation or perhaps somebody at work has a horrible gum-smacking habit and nobody wants to tell them. There’s “self-talk” you first have to give yourself when you’re preparing for an awkward conversation: your discomfort is less important than your colleague’s embarrassment. Then, you simply just tell them in a straightforward and discrete way. This is something you should do all of the time. You want to be the kind of person who will have that awkward conversation to help a colleague or friend. This actually wins you a lot of points and fosters instant trust building.

The second level of difficult conversations is alignment. Misalignment occurs all the time in business. Perhaps teams have different metrics that start clashing and cause friction. Or maybe one team is depending on another, but that team isn’t going to deliver on time because the priorities are misaligned. These are natural occurrences, and we have to be able to have difficult conversations when misalignment happens. The first thing you must do when dealing with misalignment is walk in your colleague’s shoes. You need to be able to phrase the argument from their standpoint, not just from your own. You also need to realize that it’s not personal. While you may feel a great deal of frustration because you’re unable to move this conversation forward, this is just a natural part of business—it’s very unlikely that this person is trying to sabotage you and your work. They’re probably just trying to meet their metrics. The script to dealing with misalignment has three parts: 1) state the misalignment openly; 2) empathize with your peer; and 3) seek input. For example, you might go to your colleague and say, “Hey, you’ve actually been optimizing on this project for economics, and I’ve been optimizing for performance. These are different trade-offs, and they’re both really important. But they’ve led us to make different recommendations, and we seem to be at an impasse. What can we do to try and get into alignment?” And then you can wrap the conversation up with: “Hey, if we’re unable to reach alignment, maybe we can go together to the next level to get more input on our decision.”

The third level of difficult conversations is the apology. You will make a lot of apologies for when things go wrong in business and in other areas of life. In business, you actually own accountability for everything your team does in addition to everything that you do. So, as you grow in leadership, you will be making apologies a lot. One thing that most people don’t realize is that if you are willing to apologize and do it quickly, it will actually diffuse many of the negative emotions that may be surrounding the situation. The script to solving this is that you must own both the problem and the remediation for the problem. If you or your team’s wrong-doing caused someone personal harm, you should also ask for forgiveness. In this case, you will 1) own what you’ve done; 2) talk through what you’re going to do better in the future; and 3) ask if they can forgive you. This can be incredibly powerful in remedying things that have gone wrong in business relationships.

The fourth level of difficult conversations is feedback. This is necessary when someone on your team has a behavioral issue that is holding them back, and you would like to give them feedback. Most people are very tempted to do this thing called a “shit sandwich.” This is when you put the feedback between two compliments. What happens when you do this is that it dilutes the message and leaves the person totally confused as to whether they are totally awesome or need to fix something. However, when you’re giving feedback, your whole goal is to help them be better at what they do. So, you really want to focus the conversation on the feedback that you think will help them improve. There are three parts to this script: 1) note the behavior that’s holding them back; 2) explain why that behavior is causing an important problem; and 3) ask them to reflect back the importance of that behavior and let the person “own” the remediation to the problem. The conversation might go something like this, “Hey, I’ve noticed that you’re often off by an order of magnitude on your estimates, but this time, it actually delayed our launch of the new app and we had to cancel our PR. Do you understand why this is so important?” Let that person reflect back, and then ask them, “what’s your suggestion for making sure this doesn’t happen in the future?” If you let the person reflect and “own” how they can make it better in the future, they’re more likely to stick to a change in behavior as opposed to you suggesting what they should do.

Last up, we have agonizing conversations. These are conversations where you’re going to have to deliver news to someone that’s going to negatively impact their life. For example, you may have to lay someone off or there is going to be a major reorg that’s going to change what they’re working on or their paygrade. The key aspect to dealing with an agonizing conversation is to really empathize with the person. The script then goes as follows: 1) acknowledge that the news you have to share is going to be something they don’t want to hear and incredibly difficult; 2) stop talking after you deliver the news; 3) let the person respond; 4) listen; and 5) once they’ve had time to process, you’re going to offer to help, and you’re going to mean it. If you offer to help and you mean it (i.e. help person find a new job or a different role within the organization), these things can actually turn out well.

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