You’ve got a colleague who hasn’t performed at their best lately. Maybe they messed up the last client project. Maybe they’ve been making the same mistakes for a while now. You’re feeling like they’re making you or the company look bad. It seems like they just don’t get it, or they just don’t care. 

What do you do?

Dealing with a situation like this can be frustrating, awkward, and irritating.

You know their boss has talked to them about it. HR has been involved. And guess what? You’re about to work with them again. Ugh!

Okay, annoyance aside, what do you want to happen here? You probably want to catch any mistakes. Ideally, you want to prevent mistakes from happening in the first place. 

You kind of want to say something, but you’re not sure how to approach the conversation. 

How to have tough conversations

Talk to this person

Nothing gets any better by cutting off communication lines and keeping things pent up. 

Go in with the intent to help

Your intent in this scenario makes a huge difference. Set aside your negative feelings for a moment and check in with yourself. I bet that you really do want to help. You want to make internal collaboration smoother. You want to provide a high-quality product or service to your client. You want everyone to contribute and get the job done.

You’re there to help. You’re not here to pile on. You’re not here to warn them, or tell them how tired you are of them messing it up for everyone. Repeat after me: you’re there to help!

Going into this conversation with the intention to help will make a world of difference. How you communicate with your words and body language will follow suit. 

You’ll help your colleague keep an open mind with positive intentions rather than shutting them down by making them feel like they’re getting a talking to.

Gather data

Most of the people that I coach in scenarios like this are making a lot of assumptions. They project their own feelings. They make up stories. It’s what we do as humans when we don’t have information—we make guesses. 

Sometimes we think we do have information. We’ve “heard things,” but these sources are rarely unbiased and don’t have the whole story.

Ask yourself: where is this person coming from and where are they at right now? Do they know they’re messing up and really want to get better? Are they really trying? Or, do they simply not care? Or, perhaps even worse, are they under the impression they’re doing a great job because no one has been honest with them?

Is the issue related to knowledge or technical skill? Do they literally not know how to do something? Is this a new type of project? Is this something you could help with?

Is the issue situational or a one-off? If they’ve got the skills, what’s keeping them from applying their skillset? Is it bandwidth? Maybe they’re getting slammed and you simply weren’t aware. Was there an interaction with the last client that sent things sideways? Is something going on outside of work that’s affecting their performance?

Think about how you’d like your colleague to think and feel as a result of your conversation

For example: I want them to feel like they can come to me without judgment. I want them to be more thorough in the information they deliver to the client or the internal team.

Another example: I want them to know that this is serious—that they could be fired if things don’t improve. I want them to know I’m going to schedule more internal check-ins with the project team. I want them to know what kind of information and updates to bring to those meetings. 

If you know what you want to get from the conversation, it will be a lot easier to get there. There are lots of ways the conversation could unfold, but having a general destination in mind will do you a lot of good.

Here are a couple other prompts for determining your goal: What needs to happen for this person and project to be successful? If I do nothing else, what are the top two most important things I need to convey?

Brainstorm this person’s strengths

This will help you see them as a whole person and not just a source of frustration. Have these at the ready to fold into the conversation. Besides their strengths at work, what are their hobbies or interests?

Pick your setting and timing carefully

You want this conversation to feel as casual as possible. If you work from home, are there days you know they’ll be in the office that you could drop in? Are there days when you’re usually both in the office anyways? Do you sit nearby and could easily chat in between meetings? Maybe you could go out to lunch sometime. Can you schedule a quick Zoom call without raising questions?

How to start the conversation

Getting started can feel like the hardest part. Once you’ve started the conversation will flow naturally. Here are some ideas for kicking things off.

Lead with an open-ended question or statement

• “What do you think about...?” 

• “How are you feeling going into...?” 

• “How’s...going so far?” 

Try something a little more specific

• “I saw that the last project was a bit of a challenge. How are you doing?” 

• “Hey, I just wanted to say, since we’re both working on X, I’m more than happy to meet up with you on it…”

• “I’ve been on a whole bunch of these types of projects, so if you have any questions, just let me know. Honestly, I’m here for anything…”

• “I know the last project was challenging, I’ve been on a number of these, how can I help with this one?”

Share something personal

• “I remember my first project like this...” 

• “When I was struggling with something before…”

• “I’ve learned over the years…”

Of course, the conversation starter you choose will depend on your own experience, skillset, and the relationship you have with your colleague. 

Hard conversations can be rewarding conversations

Having this kind of conversation, while hard, can be very rewarding. You could learn a lot of new, helpful, and relevant information. You can improve your relationship and learn to work better with your colleague. You can solve a problem and put past issues behind you.

And don’t forget: showing your colleague that you’ve got the time for them could mean a lot. Taking the time to reach out and have a thoughtful conversation shows them that you care personally. This can go a long way for both of you.

Even if nothing changes and this person gets taken off the project or let go from the company, you did all you could. And, you’ll feel good knowing that.

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About The Author

Emily Sander is an ICF-certified leadership coach with more than 15 years of experience in the business world and the author of Hacking Executive Leadership. She’s been featured in several print publications, online articles, and podcasts, including CEO Today Magazine, Leading to Fulfillment, and Leadership Powered by Common Sense. 

Emily has a passion for helping business leaders reach their full potential. Go here to read her story from seasoned executive to knowledgeable coach. If you want to send Emily a quick message, then visit her contact page here.