My former marketing director had just reviewed a plan with my team to drive traffic and sales into local restaurants. It was full of interesting activities, but the strategy was less clear. When it came time for questions, I asked my director specifically about the strategy behind the tactics. What I heard next was — nothing. The stretch of silence that came after my question prompted me to check my phone to ensure I hadn’t accidentally pressed the mute button. When my director eventually followed up with a few confusing sentences, I realized I had unintentionally caught him off guard; he wasn’t prepared to answer my question. Shortly after we hung up from the call, my phone rang again. It was my director calling to tell me that I needed to watch my tone.

Another period of awkward silence followed, which, this time, I initiated. I was baffled at what felt like his attempt to make his lack of preparation my problem — and even more upset that I had been tone-policed, a racial microaggression that Black women are commonly subjected to.

And, just like that, I was invited to have a hard conversation.

Over the course of the summer you will also be invited to have hard conversations — and mediate them too. These can emerge anywhere, at any time, between anyone. They can surface among fellow summer staff, between campers, or involve a combination of the two. They can bubble up over nearly any topic — including boundaries, work and communication styles, camp culture, politics, religion, and race.

Regardless of how and why they manifest, though, hard conversations can be made more palatable if you use the following strategies.

Before the Conversation . . .

. . . Evaluate the Risk

Hard conversations often feel risky and therefore require courage. Before you’ve uttered a word, your mind wastes no time playing out worst-case scenarios of how things could end — with you losing respect, a sense of self, your job, or professional momentum. Your mind is simply doing its thing — trying to keep you safe — no matter how irrational that may be. When conjuring courage, it’s important that you evaluate risks to help determine which of them are real and which are imagined. One of the easiest and most impactful ways to do this is to simply ask yourself the question, “What is the risk?” Interrupting a negative and emotional thought loop with this question brings you back to the present and the ability to think rationally. You’ll want to be sure that you detect the real risks of having a difficult conversation and of not having it at all. While avoiding the conversation may feel more comfortable in the moment, it’s important to understand that staying mum could be riskier and have bigger consequences in the end. You could (and probably would) be trading an opportunity for personal growth and development for comfort.

I believe an important reason why people don’t have hard conversations is because their emotions don’t allow them to take time to sort through the risks. Having a difficult discussion with my boss meant that I’d risk making him uncomfortable and resentful, which could have resulted in my being isolated from important projects. Not having the conversation, though, could have led to passivity in the workplace (a go-along-to-get-along approach), stressful internal conflict — or, in my case, a perpetuation of the notion that Black women must speak in a way that’s not too confident, too loud, or too direct to make some people feel comfortable. You have to decide which risk is more impactful.

. . . Clarify Your Why and Your What

Consider this: why would you expose yourself to potential rejection, embarrassment, failure, and discomfort in the process of having a hard conversation?

It should be because you’ve got an internal drive to do so. Being internally motivated means that you take an action to extend and exercise your capabilities. It means your values and actions are connected. Your why is your anchor and plays a critical role in helping you navigate through challenging parts of a conversation and its aftermath (especially if the aftermath isn’t pretty). With an internal motivation, you’re not engaging in difficult dialogue because someone double-dog-dared you, for attention, or for a pat on the back. The fear associated with hard conversations is often too strong and overwhelming to be overcome by motivations that are primarily outside of yourself. So, it’s important to know before going into a hard conversation what your motivation is. Is it about something inside or outside of you? I was motivated to have a conversation with my director to honor myself  — to stand up and speak up for myself.

Some difficult conversations come at you fast and hard with little time to prepare. But there’s no rule that you must have the conversation in the moment. I wasn’t prepared to have a difficult exchange with my director at the time of his call, so I asked if we could schedule time later in the week to talk about it further. He agreed. With whatever time you have, consider what you’d like to get out of the conversation. Having an intended outcome will help you navigate through the conversation efficiently and help bring it back to center if emotions cause it to go sideways.

During the Conversation . . .

. . . Drop Your Weapons

It’s common to anticipate a battle when you enter into a difficult conversation, but there doesn’t have to be one. You and the person you’re talking with don’t need to recreate Daniel Son’s final fight in the movie The Karate Kid. Assume that the other person has good intentions. This, undoubtedly, can be hard to do if you have strong feelings invested, which is another reason why giving yourself time to prepare for the conversation can be helpful. When you bring a lighter energy to the conversation (please don’t confuse being lighter with being nonchalant), you can inspire the person you’re talking with to adjust their energy to match yours. Dropping your defenses also allows you to listen — truly listen — to the other person rather than anxiously preparing a response to their commentary.

. . . Ask Questions

Questions are your friend when you’re in the middle of a hard conversation, because they serve multiple purposes. Internal questions help you sort out the accuracy and usefulness of thoughts you may have if your emotions begin to overwhelm you. For example, What assumptions am I making? What is the evidence that supports this? Is there another way of looking at it?

You can also ask these questions of yourself before you enter into a conversation to help unpack what you might be feeling before getting in front of the other person.

External questions are critical too. These are the ones you ask out loud in the room. External questions such as, “Can you explain that in more detail?” or “Can you give me an example of that?” help create clarity in a conversation. They can also serve as buffers to give you more time to regain control of your emotions, if necessary, before diving deeper in dialogue. External questions additionally encourage the person you’re speaking with to articulate their opinion rather than spew a series of counter statements or arguments. Questions like “What is your perspective on . . . ” and “Do you think . . . ” encourage the person you’re talking with to think carefully about their opinions, beliefs, and answers — because they’re committing to their words when they speak them aloud. In the process of sorting through their thoughts to answer these questions, they may further open themselves to your perspective.

After the Conversation . . .

. . . Give Yourself Credit

When the conversation is over, regardless of what happened, give yourself credit for taking a risk to engage in difficult dialogue. You tested your skills, and you should now have more insight into how reliable those skills are. As you have additional difficult conversations, you’ll become increasingly better at navigating through them with openness and ease.

. . . Find the Positive

Reflecting on the conversation by finding three positive aspects or experiences within it can be helpful. Sometimes, it may seem as though there’s nothing positive to talk about once a conversation is done — but there always is. Don’t overlook things such as:

  • Being able to share your perspective
  • Keeping your emotions under control
  • Ending the conversation with clear follow-up actions
  • Releasing tension
  • Getting clarity

The conversation with my director lasted over an hour and was particularly challenging at times. There were moments when he fiercely defended himself and moments when I felt like I wasn’t being heard. In the end, he apologized for his comment about my tone and accepted some responsibility for the circumstances that led to our conversation. We also agreed to talk in advance about his plans that impacted my team so he could get my input on the front end rather than the back end.

Conjuring your courage to have a hard conversation doesn’t promise that the discussion will end successfully — or as you intend. But it will always promise to open the door to possibility.

Summer camp provides an unmatched space for campers to grow and develop. That’s because camp is fertile ground for campers to take risks. You’ll also find yourself growing and developing as you take risks and say yes to the invitations you’ll undoubtedly receive to engage in difficult dialogue. And when you do, don’t forget to leverage these strategies before, during, and after the conversation.

Discussion Questions

  1. In the past, what has prevented you from having difficult conversations?
  2. Which strategy listed do you think would be the most impactful in helping you have a hard conversation?
  3. What situations do you expect will arise this summer that may require a difficult discussion with a camper? A fellow counselor? Camp leadership?

Candace Doby is a courage coach, host of The Courage Hotline podcast, and author of the book A Cool Girl’s Guide to Courage. She works with universities and organizations to help emerging leaders activate personal courage to perform to their potential at work and in the world. When she’s not speaking, she’s working on new designs for her greeting card and gift company, Pep Talker.

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