11 min read

DPM War Stories: The Difficult Conversation

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As someone who's managed projects in some capacity for more than 20 years, I've got stories to tell. I've decided to record my stories in written format, and possibly on video as well. Here goes my first one. I'd love your feedback or comments.


Being a project manager means that you have to do your best to relate to everyone on your team. And it’s not easy. For a long time I thought it just took time—that was until I was on an agency team for a couple years and still encountered issues with people. Sure, I had built pretty solid rapport with my team and we’d overcome a lot of project and client issues together. But when it came to the interpersonal stuff, we were a mess.

We were in the middle of creating a ton of work for a huge brand. It was millions of dollars in budget and the stakes were high. Typical for the type of client we worked with. Also typical for that kind of work is the soul crushing feeling you get when you’re on your 8th round of changes and legal review. It seriously takes a strong person to sustain a career in creative working with that type of client. As a team, there were times that we’d commiserate and even complain about the client and the work. It was natural team bonding, but also a “Am I crazy to think this??” kind of gut check that you just had to do (and probably shouldn’t do with management). At the time, it felt healthy, cathartic, even. That was until it just went too far.

Because when it comes to project work, the show must go on. You’ve got to put your emotions and disagreements aside in order to get the work done. But that doesn’t mean emotions don’t exist. Or that others can’t feel the emotions that you’re inadvertently expressing. And that was the case with one team member, who happened to be a friend. He was the ringleader of the complainers. Not only when it came to the project, but when it came to the company, the work, and pretty much anything else you could think of. he was a part of the team before I joined, and he honestly scared me. he was actually pretty welcoming and kind in a way that I did not expect, and I appreciated it. I also came to appreciate him point of view, professionalism (as it related to the actual work product), attention to detail and quality, and even him angry brand of sarcasm. he was fun to commiserate with because he got it, and he found a way to have a (dark) sense of humor about things. Little did I know, his particular brand of sarcasm wasn’t received well, appreciated, or really understood by most of the team. If you know me, you know my sense of humor is sacasting and maybe sometimes brash, but I’m level headed and I know when and how to use it. I think that’s important when you’re leading teams. You can’t communicate the same way to everyone. 

The issue

So anyway, back to the story. I’ll never forget the day when 2 team members came to me privately to talk about this person. They approached me at my desk, awkwardly and asked if I had a minute to speak in private?

Alarmed and slightly concerned, I accepted. We met briefly in an open conference room. I walked in and said, “Hey. What’s up?”

Right away, one of them came at me with, “We need to talk about Fred. his attitude is so terrible. I can’t work like this. Can you figure out a way to get him reassigned to another project?”

I thought to myself for a sec...I knew he was in a mood, but reassigned? That seemed harsh. So I said something like, “I think he’s really valuable to this project because he has so much experience with the brand and the client. Finding and onboarding someone new would be kind of tough to do. I’d rather try to fix the issue, if possible. What exactly is the problem?”

Oh they were ready and let’s be honest, I knew the answer.  “It’s the comments. The negativity. I feel like he hates the work, he hates the client, and it’s really bringing everyone down.”

I didn’t disagree, but I felt like I knew this person. He was my teammate, my friend. I felt like I had to try to do best by him, because...that’s what you had to do as a leader. So I just said I felt like it probably was just about his approach. Maybe I could talk to him about it and see if we can turn it around. I asked them, “What do you think?” and I wasn’t surprised to hear, “I doubt it will work, but you can try.”

Like I said, I was not completely blindsided by this. In fact, I was kind of feeling it. And I should have done something about it sooner. But I wasn’t senior, and sometimes in agencies thime isn’t much you can do about people when you’re a PM. Because you’re not a people manager, you’re a project manager. And, in this case,  I felt like I “got” this person and it wasn’t that big of an issue. Until another person came to me with a similar experience. Then a third. 

The next conversation reflected the last, and the theme was essentially, “he’s unhappy and it’s making us unhappy. And it’s affecting the work.”

I knew that I needed to address it. But how? Man, was I nervous. I had to talk to a coworker and friend about his attitude. All I could think was, "How did I get into this situation? Why me? Is this really my job??”

The reality of the situation was that there was an issue on my project, and the success of the overall project was at risk. So, yeah dude, it’s on you. If you’re a PM and you’re facing any kind of issue on a project—whether it’s related to goals, deadlines, budget, people, etc.—it’s on you to address it. So I did just that. 

Immediately after the third complaint over two days, I reached out to my teammate to talk. Because we’d already been to lunch and out for coffees, even to happy hours, I felt comfortable inviting him to lunch. Of course, he tried to make it a group lunch and I awkwardly had to say, “Actually, I want to talk about some project stuff, so can it just be us?” Thankfully, he accepted. 

I knew that I had to be open and honest, and just go with my gut. I figured I had earned him trust, and that he knew I wouldn’t ever want to cause negativity or drama. At the same time, I truly had no idea how he would receive the news. So, I wanted to get him out of the office in a public place while we could speak comfortably and privately. I also wanted to make sure there were no spectators. Every conference room in the office had a glass door, so you could see what was going on, and the last thing I needed was one of my other teammates passing by, making eye contact, or even seeing me talking to him. 

Plus, I had no idea how he’d react! Would I get laughed at? Would he stand up and leave? Yell? Cry? I had no clue what to expect, but I knew that I had to address it and hope for the best. And the best thing to do was keep this confidential, so being out of the office was best. So we had lunch at one of our favorite spots the next day.

All I could think about that night was what was going to happen. I had an image of this person telling me off loudly and walking out of a restaurant. Then I imagined him going back to the office and telling my boss that I was out of line. My mind got the best of me, which can happen when this kind of stress comes on. I talked myself out of the stress and came up with a plan. I’d sit down, state the issue, and listen. Then drive the conversation to a resolution—though I wasn’t sure what I wanted it to be until I spoke to him. 

The Meeting

We sat down and ordered. While we were waiting for our food, I spit it out.

“Ok, I just want to talk to you for a few minutes about an issue I’m hearing from the team. Essentially, your attitude is affecting the team. I know things are less than optimal, and we openly complain about work a lot. I’m totally guilty of that and need to get better. But a few people came to me because they feel like your negative comments about the work and the client are dragging them down. So I’m worried and wanted to talk through it with you.”

I felt like I was lobbing a lead ball across the table. It landed with a profound silence and a dead stare at me, as if I did something wrong. And then the tone changed quickly. First it was a laugh. Then it was, “Are you f-ing kidding me?”

No, actually, I wasn’t joking. And he knew it. I wanted to jump in and say how awkward this is and that I knew him, but I felt like I needed to stay on task, on message. I needed to understand what was going on. I mean, I felt like I already understood it, but maybe I was wrong. Either way, I needed to address it and make it less awkward. It felt terrible. I was anxious, but I tried my best to stay cool. After a few short breaths, he continued. The tone got very serious.

He said, “Listen, you know my personality. I’m sarcastic. I guess people don’t get that. Yes, the work sucks. Do I want to do this? No, but it’s my job. My coping mechanism for getting through this crap project. I cannot believe that people would complain to you about this. It’s ridiculous.”

So we talked it through. I told him that, fortunately, I understood him personality. And I actually enjoyed working with him, but I could understand how some people might not feel the same way. I even tried to bring some levity to the conversation when I told him that when we first started working together he made me nervous. That it took me a few months to “get” him, and that I had to find ways to relate. I was lucky that I felt comfortable saying that. But I felt like I had to do everything I could to get him to understand the point of view. But at the same time, I didn’t want him to think that I’d ever expect his personality to change for a job. 

What he COULD do was find better ways of expressing his frustration, particularly when the whole team was present. So we talked about things, back and forth while eating, in an open way. It was all positive, and relaxed - THANKFULLY it wasn’t the blood bath I had stressed about the night before, so I already felt like I was winning. The thing was, we ended up just talking like friends. And it wasn’t going anywhere that I could see there would be an actual change. So I asked one question that changed everything. I said, “Alright, thanks for hearing me out and talking through this. What are we going to do to turn the situation around?”

This was the kind of question he was used to hearing me asking in meetings, so it wasn’t totally unexpected. It led to some discussion about next steps, which were essentially about finding better outlets for grievances, toning down the negativity in team meetings (on both of our parts), and following up. We left the restaurant with an agreement that we’d follow-up in one week to talk about how we were feeling.

It didn’t end there

We got back to the office and within 10 minutes, one of the folks who had complained to me sent me an instant message asking how lunch was. Interesting, because I told no one about my conversations with team members, or the fact that we’d be having lunch or discussing the issue. My response was simple, “Good, thanks.”

Then I thought for a minute. This issue wasn’t all about the person I just spoke to at the restaurant. Sure, the attitude was a little extra, but it wasn’t dire. The immediate follow-up bothered me—it felt icky. Like I was being checked up on, played with. I mean, the bottom line is that when you have an issue with a team member, you should address it directly with them. And I typically would have just said that to these folks, because as a PM, I try my best to be Switzerland—completely neutral. The only reason I intervened in this situation was because a few people piled on! I never suspected that they’d conspired to all talk to me. I figured that out quickly by asking some simple questions of all three. It was such a disappointment to find out that I was basically being gamed. Over staffing!

So I called a meeting with the three of them. We sat down in a conference room, and I asked them a very direct question: “Why did you all come to me separately about Fred? What did you expect to get out of this?”

Again, it was uncomfortable. But not for me, because I was Pissed, with a capital “P”. They looked at one another and the one who came to me first said, “Well, we all have been talking about how the negativity is affecting us, so we wanted help fixing the situation.”

I told them I understood, and that I actually appreciated the sentiment. But the approach? Not okay. Essentially, by creating their own backchannel, they were only making the issue worse. I needed to make sure that this was limited to them. and not the other 4 people on the team. Thankfully it was. 

At the same time, I knew that I could not divulge ANY of the lunch conversation, because, well, that would just be wrong. And it would completely damage the trust I’d built with that person. So I said something that I’d hoped would end the situation:

“Please know that I’ve heard your issues and have addressed them. This is not an overnight change, because we’re not kicking a talented person off the team over a misunderstanding. And I happen to think that we’ll see some changes due to the conversation we had. But, at the same time, can you please commit to being more honest and open about issues in the future? Right now I’m feeling like you all used me to get what you want out of the situation, and that is not okay. Not only because I’m not a puppet master or even a people manager, but we don’t just move people around because of a personality difference. If we want this team to work well, and for our clients to be happy, we have to be honest and direct in our communications, and our intent. That means if you have an issue with a person, address it yourself. I’m always here to support, but I’m not your messenger, or your fixer.”

It was harsh, but it was the truth. I felt like a babysitter, and that is never what I wanted out of my role. So I did my best to be honest, set the record straight and move on. Thankfully, they all did too.

I checked in a week later, separately, with all of them. I wanted to be sure they all knew that I hadn’t forgotten, and that I was serious about making a change for the better. The follow-up with Fred was simple, because he got it. I told him he could always come to me with complaints and sarcasm, and I’d always hear him out and give him my honest response. I told he wouldn’t always like my response, but he needed a voice of reason. As for the other three, well, they didn’t have to change much aside from not being gossipy, but I felt like I set a very clear expectation with them about it. And I never heard another complaint from them.

The moral of the story

Looking back on this situation, of course there are some things I could have done and said differently. But at the end of the day, everything was resolved. It’s actually kind of funny, too, because having the meetings I had with all four people earned me a new kind of respect with those folks. I guess they liked my “no BS” approach, because a week later I got a spot bonus due to an anonymous employee recognition program. And later that year I found out that I had become the PM they wanted to work with more often. I guess acting fast, being honest, having some empathy, and embracing your own feelings can help you be a better PM.

So...that difficult conversation ended well for me. I’m sure you’ve had situations like this arise on your projects, or even in your office. How did you handle them? OR, should I have done something different here? Let’s discuss--Leave a comment below. And if you liked this, how would you feel about a video version of this story? It's an idea I'm working on, and I'd love your input, and maybe even your stories!