My Most Successful Tough Conversations with Coworkers

When you’re having tough conversations it’s critical to be honest, kind, and sets standards for the future. It not only sets you apart as a leader on the team but it helps people work more effectively. It also sets the team up for success. I actually have 6 great reasons why you want to have the tough conversations (and 3 of them specifically benefit you) recorded in this week’s YouTube video. Click here to watch it. In this blog post though, we’ll not only cover great examples of tough conversations but also the risks of avoiding them. Ready to get more comfortable with the uncomfortable? Let’s dive in.

Paths of least resistance to tough conversations

We all know the go-to for tough conversations with your peers. Odds are you did it repeatedly in school for group projects. That’s right, we ignore the problem and take on the work ourselves. Stop doing that. Taking on the work just sets the standard for others that you will handle it and they’ll still get credit. Eventually, the other person will be taken off projects with you sure, but you’ll be seen as so effective that you really can do it all yourself. Not what we’re going for. Unless you are, then tout that you did all that work all day long. Take credit for the work you did. Stop with the we when you’re sharing what you achieved and replace it with I.

The other option for those tough conversations, involving the boss. Now, I’m never going to tell you to not go to your leader for help. That is literally what they are there for, to support you, their employee. In some of my courses I refer to telling the boss as the get out of jail free card. While that is true most of the time, you only want to use that card when it’s really needed. Otherwise, your boss starts asking questions like:

• Do you really consider this jail? Seems more like a fence you could have hopped.
• Why is it that you’re always in jail? I’m tired of coming to the rescue.
• Are you in jail again? I’m running low on bail money.

A silly metaphor I know but, I think you know what I mean. Every boss has their own limit on when they’ll start asking the questions too so it’s a good idea to have a strong alternative.

A few tough conversation successes

Telling Jim to pull his weight.

A group of 5 of us were working on a project that would take months to complete. Each of us had a designated role that was pretty clear cut. Because we had such limited people for the size of the project, we each needed to be diligent in completing our piece of the pie. We were also all leaders. So on top of our typical work and this project, we all had teams to be responsible for. One member of the group, Jim, had stopped working the project because he needed to focus on the team.

I was frustrated with his attitude and effort and several other members of the team had voiced concerns also. So, I set time with him outside of the project meetings. I agreed and empathized with him on the struggles of balancing team needs and the project. Then, I shared some of my strategies to keep that balance. He had plenty of reasons why those strategies wouldn’t work for him and his group. So, I very plainly said, Then, you’ll need to find a strategy of your own. As a leader you are expected to be able to lead people and complete work. If you don’t complete it this project will fail.

Explaining to Becca why people avoid her.

Working in a consultant role I was part of a very small team. Each of us did a similar type of work but served and supported separate groups. For the most part our groups only interacted with their identified consultant, but we could back each other up as needed. I was bringing one of my teammates, Becca, up to speed on a situation that her group had brought to me and she confided that they weren’t bringing any questions to her. She got all of the information second hand through some member of our team.

Our little team was very tight knit and we all really cared about each other. With all of the compassion in the world I explained what was going on. You are crazy smart, but pretty intimidating. It makes people want to put in a buffer. I explained that when I was hired and needed to ask a lot of questions, I had an order for who to go to and she was last on that list. I went on. Becca, you know so much and it comes as such second nature that when people ask you a ‘dumb question’ you are really sharp. Plus, your face is giving a little too much away. It was a very hard conversation with someone I considered a friend, but I couldn’t let her go on feeling like everyone was going around her.

Ensuring Steph takes responsibility.

If you’ve ever been emersed in volunteer work you know it can be very easy to develop an ‘us vs them’ mentality. It happens everywhere but is even more prevalent in volunteerism because we start to think that we’re the good ones because we’re taking action. For us to be good, those who aren’t volunteering must be bad in some way.

I was working in one such group when a fellow volunteer, Steph, noticed there was a mistake in the financials. Steph was sure others weren’t following the process we had put in place. The mistake was a small onetime issue that wouldn’t make a difference in our work. Yet, Steph just kept bringing it up. Because Steph was talking about it months after it happened, I decided to look into it. After digging in I realized it was actually her mistake. Still small, still no impact, but the them accusation was actually her.

Not wanting to embarrass Steph, or add to the continued conversation, I pulled her aside one afternoon. I looked at the document after our last conversation and it looks like you entered the inaccurate information. As we’ve been saying for a while, it doesn’t impact us going forward. We all make mistakes. I think at this point we can put this one to rest. Steph was surprised and annoyed but said she would look again. She must have found the same thing because she never brought it up going forward.

What did all those tough conversations have in common?

I didn’t sugar coat the truth. There was a clear issue to be addressed for all of them and while it might have been more comfortable to ignore it, I knew that wouldn’t have a positive effect long term. It is hard to tell people when they are doing something wrong but ultimately addressing it is always best.

Regardless of how I felt in those situations I was kind. My face has been known to give a little more information about how I’m feeling (Becca and I are kindred souls) but I didn’t beat them up. Instead, we created a path forward, through these tough conversations. Yes, we were honest about the past but we didn’t dwell there. Just like I didn’t want Steph to beat the dead horse when we thought others made a mistake, I didn’t want to beat her down either. Even when I was irritated with my peers or they were in the wrong, we focused the conversation on the future.

Looking to the future not only helps you handle the moment you’re in with grace, it also propels you forward. I’ll be honest, I didn’t like Jim. I didn’t really care if I extended a lot of grace to him. I did however want that project to be successful. By setting the standard of what was expected of all of us, and not dwelling on the team’s or my feelings, we could be more effective as a group.

What happens after those tough conversations?

Once you’ve had the conversation with your teammate, as hard as it was, don’t let that be the end of it. There are three very important things I want you to do to make sure you’re making the most of this opportunity. First, make sure you share what happened with your boss. Communicate it positively starting with the results. I talked to Jim, and now we’re better aligned on responsibilities. He’ll be responsible for X,Y, and Z going forward. Your boss is very likely to ask questions. This is a chance to double down on objective, kind, forward thinking.

Then, hold your ground. Whatever result was achieved and decided on in the conversation needs to be held as the standard. Finally, make sure that this is on your resume. Now, you can’t say Helped Sara not be such a bag. But you can say, Developed team members to facilitate collaboration resulting in excellent work utilizing all skill sets on deadline.

In the end though, I know these things rarely have clean, once and done results. If you have specific issues to work through to better work with your teammates, click here to set up a time to talk about how we can set you up for success.