The Key to Leading Difficult Conversations: Strategies for High Performers

If you’ve ever caught a rerun of the 1980s sitcom Designing Women, you may be familiar with Julia Sugarbaker’s epic takedowns.

No matter what was happening in the episode, this character was laser-focused and whip-smart. She had a comeback for everything and a skill for putting bad actors in their place.

And she never broke a sweat doing it.

In real life, most of us don’t handle difficult conversations with this level of aplomb. We’re usually sweating it out to some degree—whether it’s before, during, or after the confrontation. Maybe all three!

While it’s not easy to stay cool and collected during difficult conversations, doing so tends to result in better outcomes.

Sometimes, it’s nothing less than required that we stay cool, especially at work.

For high-performing people, these high-stakes situations might come around more often than average. After all, with a lot of responsibility come a lot of moving pieces.

You might find yourself not only participating in but leading difficult conversations…

And the key to success is preparation.

Keep Yourself Grounded

Before you can successfully lead difficult conversations, you need to be aware of your own triggers. To stay in control of a challenging discussion, not only must you start from a calm place—you must also remain calm, even if the other person does not.

Begin by noticing how your body feels when a conversation escalates, or when you get upset in general. Do you notice your muscles tensing, your heart rate speeding up, or your breathing becoming shallow?

If you aren’t used to noticing your thought patterns or the way your emotions show up as sensations in your body, mindfulness training may help.

If you do find yourself in a heightened state of stress, try to ground yourself again by focusing on your senses. For example, touching something solid—like the desk in front of you—and focusing your attention on it for a few seconds may be enough to clear your head and bring your awareness back to the present.

You may also choose to focus on your breathing. An intentional exercise—like inhaling for four seconds, holding your breath for four seconds, and then exhaling for four seconds—can be helpful here.

Be mindful of how your body language may change as your own inner tension escalates. Adjust and assume a more relaxed posture or position, as possible.

Preparation is Key to Leading Difficult Conversations

Preparation is key when it comes to leading difficult conversations. As a high-performer, you’re likely very good at anticipating a variety of possible outcomes—you’ll utilize that skill here.

What’s your end goal? 

Go into the conversation knowing in advance what an acceptable outcome will be. What do you want to achieve? If the other person isn’t willing or able to give what you’d like, are there acceptable alternatives? Know ahead of time where you’re comfortable compromising.

Are you already familiar with this person’s conversation style or approach?

If you’ve known your discussion partner’s temperament to be calm and accommodating, there’s no sense in fighting with them in your head beforehand!

But if you can reasonably expect the person you’re engaging to be upset or emotional at the confrontation, then visualize yourself staying calm in the face of their reaction. Additionally, if you can anticipate what a trigger might be for them in the conversation, see if you can figure out a way to avoid broaching it.

What responsibility can you take for the situation you’re addressing?

Leading a difficult conversation will be a far more successful endeavor if you’re open and honest about the role you’ve played in the situation you’re addressing. For example, if you need to approach an employee about poor performance on a project, be open to the possibility that you could have provided more support, or that there was a miscommunication along the way.

Plan for a soft start. 

Approaching someone with a statement like, “We have a problem we need to discuss” is sure to put them on the defensive immediately. Instead, try phrases like, “I’m curious about..” or “I think we may have had a misunderstanding—I’d like your help in figuring it out.” Beginning a difficult conversation with a soft start sets a supportive tone that will ultimately go further toward an acceptable resolution.

Curiosity Is the Best Tool in Your Tool Belt

Stay mentally and emotionally present when leading a difficult conversation. You don’t want to feel like you’ve lost control of the discussion at any point; if you begin to, it’s best you hit the pause button, and revisit it later.

But staying in control doesn’t mean being harsh or aggressive. Practice active listening, and ask questions to truly understand the other person’s perspective.

Curiosity is the best tool in your belt when leading difficult conversations. It will ultimately allow you to feel and show the kind of empathy that usually disarms a potentially combative discussion partner.

Curiosity also provides an opportunity for learning. When you’re able to dig more deeply—to the root of an issue—you can better understand how to avoid disappointments next time.

If active listening winds up uncovering blame or responsibility on your part, meet that feedback with acceptance. As high-performers, we’re used to being the problem solvers, so it can be difficult to accept that we’ve done something imperfectly. But none of us are immune to making mistakes.

Instead of getting defensive, try responding with statements like the following:

  • “Thank you for expressing your frustration. I see that I could have approached that differently.”
  • “I hadn’t realized my actions were being interpreted that way. I’ll make sure to check in earlier in the process as we move forward.”
  • “I appreciate your honesty, and I’m sorry you didn’t feel comfortable bringing this up earlier.”

Don’t be afraid to jump into the details, where it’s appropriate. While you don’t want to dwell on any negative points, it can be valuable to gather more information about the other person’s “why”—as well as share your own.

Make Time for the Repair

Leading a difficult conversation means you’ll also be in a position to end a difficult conversation. Make sure you do so on a positive note—recap the discussion you’ve had, restate the agreements made, and identify steps for moving forward.

Do your best to repair, as necessary. Thank the other person for taking time for the conversation, appreciate them for their honesty, and give them a chance to ask any final questions or share remaining concerns.

And while it’s much easier to engage in this process around a new topic and have time to prepare yourself for the conversation, it’s absolutely possible to use it if the discussion has already happened—even if it got a little heated.

In this case, approach the other person openly and honestly, take accountability, and use the steps outlined above in a new and fresh discussion.


If you’re a high-performing executive looking for support and guidance, consider working with a clinical psychologist to help find balance and reach your goals. >>


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