| Daily Briefing

The 6-step roadmap for that tough conversation

In an earlier post, I shared 5 ways to prepare yourself to have any tough conversation, whether that means giving an employee difficult performance feedback, sharing challenging news about your organization, or bringing up complicated issues around diversity and inclusion.

5 ways to get ready for a tough conversation

But even after you've identified the value-driven reasons why it's important to have these difficult conversations, you may feel trepidation mounting as the "big talk" approaches. So how can you make the conversation as easy as possible—both for yourself and for the person you're speaking with?

Here are six strategies.

1. Plan out your approach

This doesn't mean you need to rigidly script yourself. It does not even mean you cannot alter your plan during the actual conversation! However, having a plan will give you the courage to get started.

As you make your plan, think through how to:

  • Directly state the reality of the situation. If a colleague has upset someone with a careless remark, for instance, you might begin the conversation with, "A lot of people were hurt by your remark, and it's important we talk about it";

  • Explain why it's important the challenge be addressed. Put another way, what important, shared value do you advance by having the conversation? For example, if opening a conversation with your team about inclusion, you might say, "It's important to me that we have an inclusive workplace, and that we aim to be empathetic with each other"; and

  • Share your initial plan for the conversation. Don't be rigid about how every element of the conversation must unfold, but do think through how to start and structure the conversation. For example, if you're building understanding in an emotionally charged situation, you might say, "I propose that we begin the conversation by all listing two emotions we've felt across the past week."

2. Find the right time for the conversation

Finding the "right time" is admittedly an inexact science! Consider these guardrails:

  • First, try to identify the moment where you realize, "We need to talk about this";

  • Then, give yourself some space to process your personal, emotional reaction. You need some distance from that reaction before you have the conversation;

  • But try not to wait too long. You want to engage close enough to your "we need to talk" realization for the conversation to be relevant.

So what time is "just right"? Use the guidance in #1 as your guide: "Just right" is likely the moment when you've had enough time to craft a thoughtful approach, but not much after that.

That said, one of the best rules I learned about thank you notes and sympathy cards was "better late than never." If you feel that so much time has passed since the catalyzing event that people might not understand the conversation's relevance, you can say something like, "I realize I should have talked to you about this sooner. Let me explain why I want to talk about it now."

3. Be aware of the identities you bring to the conversation

All of us are influenced by various aspects of our identity: gender, age, race, nationality, religious/spiritual affiliation, social-economic status—to name a few.

To approach tough conversations inclusively, it's wise to think about how our identities shape us. As we do so, pay particular attention to identities you think about the least often.

Why? Because these unconsidered identities are places where you may hold a lot of privilege—unearned access to resources only readily available to some people as a result of their advantaged social group membership—in relation to others.

For example, in predominantly white spaces, white people may minimize whiteness as part of their identity and its associated privilege. In predominantly heterosexual spaces, heterosexuals may minimize heterosexuality as part of their identity and its associated privilege. Those with enough money to make ends meet may not think about their socio-economic status.

Awareness of our identities helps us not makes assumptions that those identities apply to others, and that usually leads us to ask better questions and to listen to how people answer them. For example, a leader aware of his or her Christian religious affiliation may, as a result of that awareness, display more sensitivity to the religious beliefs of a non-Christian in a tough conversation about leave requests.

4. Listen more than you talk

This can be easier said than done! To encourage yourself to actively listen, try the following tips:

  • Limit distractions. When having a tough conversation virtually, turn over your cell phone, close your email, and block the 30 minutes after the meeting so you don't feel pressured to end early. Do everything you can to direct attention to the conversation itself;

  • Embrace pauses. Breaks in dialogue are natural and give you a chance to collect your thoughts;

  • Use "minimal encouragers." In conversations held over the phone or Zoom, your conversational partners can sometimes misinterpret silence as a sign of a dropped call or technical problems—or they may simply worry you're checking your email in another window. To fight this impression, use so-called "minimal encouragers": subtle sounds such as "mmhmm" or "I see" that let the other person know you're still listening without disrupting their commentary;

  • Pay attention to what is being said, not what you want to say. One way to do this is to strive to repeat the goal of repeating the last sentence of what others say. That sustains your attention on what they say until they are done, instead of diverting your attention to how you will respond; and

  • Paraphrase and test for accuracy. Say things like "Let me see if I heard you correctly..." to pressure-test whether you are hearing and perceiving comments accurately.

5. Own when you get it wrong

This is a key part of a growth mindset. We all intend to be good people, but we inevitably will say or do the wrong thing sometimes—especially in a difficult conversation, where the "right thing" can be so hard to identify.

A key trait of inclusive leaders is not the absence of error or bias, but awareness and a willingness to accept that you'll get it wrong sometimes.

When you get it wrong, do not minimize. Do not focus your apology on your good intent. Instead, focus your apology on empathizing with the hurt caused and learning how you can do better next time.

6. Follow up (in the right way) when the conversation is done

Bear in mind that, while the conversation was difficult for you, it may have been even more difficult for the person you were speaking to! Take time to express your gratitude in writing, whether via email or a handwritten note, for their participation. In that note, try to indicate specific areas of appreciation, such as a perspective that was shared, moments where you learned, or places where active listening was displayed.

Then, indicate a specific action you will take in response to the conversation, and commit to a date for that next step's completion. You might write, for example, "I will talk to ___ about ___," or, "I will exhibit greater consciousness and sensitivity about ___." You might also set a date on which you will seek feedback as to the effectiveness of your next step.






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