Have the Hard Conversation

There’s a tough conversation I’ve been meaning to have with a coworker for several months, but I put it off.

I put it off partially because I wanted to ask her to change how her team does some things. My reasons are noble: I want her team to do things more consistently with standard project management processes, so that my project management team can provide better service on projects that involve her team. But when I ask people to change—at least in ways that don’t have obvious, immediate benefits for them—I expect resistance. So I wasn’t looking forward to that.

I also put it off because I wasn’t confident in my ability to explain the changes I wanted and why. Our “standard” project management practices, while normal for many of our teams, are not well-codified. This is the type of conversation I would have preferred to have in the context of well-codified PM practices with clearly documented value. It’s a high-priority goal of mine to codify our practices, but it’s also a big project that I haven’t had time for. Real-life project management is messy! In the meantime, we’ve run into enough snags with this team that I didn’t feel it could wait. I’d need to just do my best and stumble through it.

There are all sorts of reasons we put off hard conversations. Sometimes it’s fear of conflict or lack of confidence in explaining ourselves, like in my case above. Sometimes we’re delaying what we expect to be a negative outcome, or we don’t want to admit we did something wrong or failed. All of these reasons, while not productive, are understandable.

I probably would have put this conversation off longer, but a brand-new monthly project that heavily involves this coworker’s team forced the issue. Suddenly I couldn’t move that project forward in an effective way until I took some time to explain to her at a higher level why I want the project run the way I do. So I sent a meeting invitation with a partial explanation of what I wanted to discuss, and I got ready to barrel through something I only felt partially prepared for.

I did try to pull my thoughts together in advance. I’d found a helpful narrative (that I believe!) about how each of our teams has grown more integrated with our company in the last few years, and our teams’ integration with each other hasn’t kept pace with this. I’d identified some of the major categories of projects and situations where I wanted certain types of changes, and which projects would be fine to stay as they are.

My boss and I also landed on a good approach where I would come into the conversation with some possible solutions, but also invite my coworker’s input so that I’m not forcing something on her team that she didn’t participate in.

All this planning was great, but I knew I’d still be nervous and probably wouldn’t get all this across as succinctly as I wanted to. But I was out of time and didn’t know how else to prepare, so I braced myself for a conversation that would probably be awkward and just okay.

As I write this, I've just finished having that conversation. And guess what?  I was right, it went just okay. I made some of my points, probably not in the clearest order because I was nervous. She was not defensive, but seemed to only partially pick up what I was trying to lay down…maybe because I only partially laid it down.

So what can I say on the other side of a hard work conversation?

I’m glad I got the discussion started. Even if I didn’t get everything across today, I laid a foundation so that I can reference, and hopefully clarify, my general goals as snags come up in the future on specific projects.

A “just okay” conversation can still be effective, especially when there’s follow-up. I’ve now heard some of her reactions, and maybe my next pass at expressing my ideas will get across to her more clearly because I’ve gotten some feedback from her. Part of my nerves were about not knowing how to express myself because I had no information about how my ideas would hit her. Now I have some.

I’m glad I didn’t put it off any longer. I’d been living with snags on these projects for a few months. Now we have the beginning of a path to make them better. If I’d waited to have a perfect means of expressing myself, I would have lived with the snags much longer (and it’s questionable whether more preparation time would have helped the conversation go better).

Openness and collaboration trumps silence, even when it starts awkwardly. When I was younger I used to think through hard conversations ad-nauseum in advance so I knew exactly what I wanted to say. But when I did this once with a close friend in college, she let me know how hurt she was that I’d tried to solve our mutual problem without her. I take this lesson into my work life—a project manager needs other people to get anything done, and a collaborative spirit about solving problems builds a better team. As my boss and I concluded: come in with some formed thoughts and ideas, but work toward a solution where everyone has input and buy-in. Be willing to adapt.

As project managers, we have plenty of hard conversations in our path. The fact that we have these conversations, that we push through when it’s tough, is one of the reasons we have the superpower to unite diverse people to create coherent, meaningful project results. Being fresh off a hard conversation myself, I do recommend you prepare some, but don’t wait too long to just have the conversation, because having it sooner will open doors sooner.  Even if you think the conversation will go just okay.

And also, I suspect the more conversations like this where I just shrug, walk in, and say “here it goes,” the more accustomed I’ll feel to the awkwardness, and the less awkward I’ll start to feel. So let’s keep diving in together.