I’ve probably mentioned this in a previous post, but assuming you’re not the one regular reader of this blog (who also happens to be named after its domain), over the past year and a half I’ve been managing teams. What exactly “managing” means is a question I still am not qualified to answer. But… one thing which I can say managing includes is having hard conversations with teammates.

As a manager, you are responsible for a number of different things like hiring, professional development, team cohesion, etc etc. But you’re really only judged by the output of your team, in the most reductionist of senses.

And so, when your team is composed of Bob, Sally, Mike, and Sue, and Mike’s output is dropping and he stops showing up to standup on time and his pull requests include no comments, dead code, and break all the test cases, you, as the manager, should probably have a conversation with Mike. I think I read that somewhere in a book.

So you think about what to say to Mike, and you’re not sure what to say but you’re pretty sure on what you don’t want to happen. You don’t want to hurt Mike’s feelings. You don’t want Mike to stop liking you. You don’t want Mike to leave the conversation thinking how miserable of a boss you are. And yet… you do want Mike’s output to miraculously sky rocket.

In short, you are being the world’s biggest baby. You are scared of having a hard conversation. You - the over-achiever who someone thought should manage other people for no other reason than your skill as an individual contributor - have never witnesed a hard conversation. You haven’t been on the receiving end. And all of your attempts at having them thus far have ended in confusing messages to a colleague who isn’t quite sure what you meant but is grateful for the cup of coffee you put on the company card.

If this sounds familiar, you should probably resign.

Just kidding, I’m pretty sure these feelings are shared across all new managers, or at least those who are not psychopaths. And the truth of the matter is that these conversations are one of the most important things you, as a manager, are responsible for. And yet, they are also one of the things you are least prepared for.

To be completely honest, they do not get less awkward or more exciting. But, you will (slowly) have less anxiety before them and become better at having them. Below are some tips that I have found useful for preparing for and having hard conversations.

How to prep for Doomsday

  • Identify problematic behavior

    The premise for a hard conversation is that something isn’t going well. To prep for a hard conversation, you should narrow in on what exactly is not going well. Is it carelessness? Is it lack of punctuality? Is it poor communication? You should try to limit the conversation to the most important thing that is not going well.[^1]

    Bad: You’re not at the level we need you to be.

    Good: I don’t believe you’re being as thoughtful as I know you can be with the code you submit in pull requests.

  • Identify specific examples

    By providing specific examples, you make the conversation actionable and divorced from the underlying person. Your teammate can no longer argue as to how thoughtful they are with their work when you reference the exact PRs that broke tests, had no documentation, and were littered with dead code and print statements.

    Bad: Over the past few weeks, you’ve consistently seemed checked out.

    Good: I noticed this across a number of the tickets from the last few sprints. For instance, I was really excited when I saw you were working to implement the magical widget in ticket 123 but felt bummed when I saw the state of the final PR. You left print statements and dead code throughout the submissions and all the integration tests failed. Most importantly, Marcia, on customer success, had specifically requested feature YYY and you neglected to implement it, despite the acceptance criteria requiring it.

  • Identify potential causes and remedies

    Your job is to get the best output from your team, not to be the best at blaming others for the lack of output. In that line of thinking, you should come prepared with potential causes and remedies. Why do you think this pattern of behavior may have occurred? If your various assumptions are correct, how could your teammate work to address them?

    Do not state these causes or remedies as fact and do not lead with them. First open up the floor to hear his or her reaction and thoughts. Press him or her on the why? Only after hearing their side, would it make sense to suggest some thoughts of your own.

    Causes could include a lack of motivation, something going on outside of work, not feeling empowered, a shift in type of work that makes he or she feel inept or unqualified, etc. Remedies could include training, providing more business context, a pump up talk, etc.

  • Write out talking points

    Why? Nerves. Until you’ve had a number of these conversations, the moment can be quite a blur. You immediately forget all of your remarks and the most salient points to get across. You look back and aren’t sure exactly what you said or how he or she perceived it. By writing it out, you can flush out your thoughts: the 2-3 points to get across, the best way to get into heart of the issue, and how you’d like the conversation to unfold. Moreover, by writing it out, you can run it by your manager or HR and get feedback on how best to approach the day.

    Don’t forget - take your notes with you!!! This is by no means an amateur move and shows that you’ve given the situation the thought and care that your report deserves.

  • Practice

    Run through your points a few times before. Make sure that you’re not softening the message or meandering. You owe your teammate honesty and clarity. Practice ensures this.

How to survive Doomsday

  • Break the ice

    Ask how they feel things are going. This is an opportunity for self-diagnosis. If they’re aware that things aren’t going well, you can dovetail on their thoughts. Otherwise, you can use this opportunity to gather more data.

  • Be clear

    The worst outcome is lack of clarity. You need to make the following clear: (a) current performance is not ok, (b) what exactly needs to be improved, (c) what next steps are.

  • Speak to behavior not character

    Always assume the best intentions behind people. Assume that they’re doing their best given their environment. Let them come away from the conversation with their pride in tact. The purpose of these moments is not to prove them wrong or put them down, but to help them become the best versions of themselves and simultaneously maximize the potential of your team.

  • Be vulnerable

    Don’t shy away from empathizing and sharing examples of similar situations that you have been in. Relatedly, you should let them do as much talking as possible and follow up with questions. The ideal outcome is that you land on the same page about the what, the why, and the how (the situation is going to be remedied). Additionally, you’re both making it clear that the status quo is unacceptable but also showing that you’re there to help.

  • Leave with action items

    Ask what they need from you. Suggest next steps. Assign dates and owners. It’s important that you follow up after these conversations. Otherwise, all of the prep and emotional toll was for nothing. More importantly, it shows that you take the matter seriously and increases the likelihood of resolving the matter.

[^1] Note: Often times, poor output may be the result of a number of behaviors. When this is the case, either try to find a specific higher level theme or pick the most problematic behavior. DO NOT try to broach multiple issues at once. This leaves people feeling defensive and dilutes the message.