How to survive a tough conversation at work

Mar 30, 2020 |Posted by Jared Simmons | Coaching

At some point in your career, you’ll be faced with the need to have a tough conversation with a colleague, boss, or team member. There are countless guides on how to master these conversations, what to do and what not to do.

Here are some things I try to keep in mind as I prepare to have a tough conversation, or suddenly find myself involved in one.

Timing is critical – have it as soon as possible

If you are prompting the discussion, try to have it as soon as you can after recognizing the need. There’s an old adage that bad news doesn’t get better with age; similarly, tough conversations don’t get any easier by delaying them.

Stick to the facts

Tough conversations are often a result of emotionally charged situations. It’s easy to let your focus shift to the way someone made you feel, or your assumptions around why they behaved the way they did. Try to keep the conversation anchored in what actually happened and the real tangible outcomes. You can address the emotional side of things as well, but only as additional context – the icing on your fact-based cake.

Assume positive intent

We are human. We naturally want to connect some sort of intention to the behavior of others. I find that reminding myself to assume that the other person was well-intentioned keeps me focused on their actions and the implications of them; and not the potentially sinister intent behind them. Even if they don’t mean well, this rarely changes your options for resolving the situation. And if it was a well-intentioned mistake, you can now address the actions and strengthen the working relationship.

Ask questions

Tough conversations tend to make me defensive. I feel like I must state my case by highlighting my observations and the implications of their behavior. Over time, I learned to treat these things as supporting context for genuinely curious questions. You can learn a lot more from questions like, “Would it surprise you to know that your teammates stayed late to correct the mistakes you made in your presentation?” than you can from simply informing them of their colleagues’ sacrifice.

Own your part of the situation

No one is perfect. Making a mistake doesn’t mean that you can’t have a tough conversation with others about their actions. Acknowledge your contribution to the poor outcome and offer solutions of how you’ll avoid similar mistakes in the future. This creates a perfect segue to ask about their behavior, its implications, and whether they’ve considered how they’ll avoid such outcomes. And because you’ve shared your own side of things, it creates an environment where it’s easier for the other person to cast a critical eye on their own behavior.

No one is an expert. We all walk away from tough conversations thinking about all of the things we could’ve or should’ve said. So, if you remember to do 2 or 3 of these things in the moment, consider it a wild success. Don’t judge your ability to have tough conversations by the outcomes of each discussion; there are a thousand factors at play, and no two discussions are alike. Figure out what works best for you. Do your best to prepare yourself for a positive outcome, and try to cut yourself some slack if things don’t turn out exactly the way you had intended.

Ultimately, winning is leaving a tough conversation with the confidence in your ability to handle them intact.

Picture of Jared Simmons

Jared Simmons

Jared is the founder of Outlast Consulting LLC, a consulting firm that helps individuals and organizations with strategy, process improvement, and professional development. He is an engineer by training with experience in market research, product development, innovation, management consulting, and strategic planning at P&G, McKinsey, and Coca-Cola.


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