Have the Hard Talk

Opening: Why We Avoid Hard Conversations

Shawna: Do you dread having those awkward conversations, so you just put them off forever and ever, and it gets you in trouble eventually because it catches up with you?

Well, I have the perfect guest to help us with this today. She is my friend, Dr. Janel Anderson.

Dr. Janel Anderson is a keynote speaker and communication expert who helps technical leaders navigate the interpersonal side of tech, where the hard work of getting people, teams, and ideas aligned actually happens. She is the author of Head On: How to Approach Difficult Conversations Directly, which gives leaders a practical, research-backed framework for the conversations most people avoid, myself included.

She brings the same approach to her podcast, Working Conversations, now five years strong. How many episodes?

Janel: 265, something like that.

Shawna: Amazing. When she’s not on stage, you’ll find her in the kitchen reverse engineering recipes from her favorite restaurants, or out on a walk with her rescue dog, the sweet Bailey the Golden. I love all of that. Janel, welcome to my show.

Janel: Thank you, Shawna. It’s so great to be here.

Shawna: And the other cool thing about Janel is she is my favoritest co-office worker ever. She’s my only co-office worker, in fact, she’s right next to me, and we’re in our studio, which is so cool. I’ve heard her in meetings, on calls, doing webinars, speaking all the time on difficult conversations. She’s so good at it, and I’m so bad at it that I knew I had to have her on the podcast.

When Is It Time to Have the Conversation?

Shawna: How do you know if you have to have a difficult conversation?

Janel: How you know if it’s time, or maybe a little past time, is if you keep thinking about that situation over and over in lots of situations. Maybe you’re driving, in the shower, or lying awake at 3:00 in the morning thinking about it. If it starts popping up in those different avenues of your life, then it’s time. It might even be a little past time.

Step 1: Emotional Regulation

Janel: Sometimes we come into conversations emotionally charged in a way that doesn’t promote resolution. The very first piece is emotional regulation, getting yourself emotionally in check before you have that conversation. If your mind is clouded with frustration or anger, the conversation isn’t going to go well. Set that aside. Don’t drag it into the conversation. Treat each conversation like it’s new, not the 13th version of the same issue.

With employees, have the conversation first thing in the day. Otherwise, you’ll put it off, and other things will interfere with your emotional state. The earlier in the day, the fewer outside frustrations influencing you.

Step 2: Start Without Triggering Defensiveness

Janel: We want to tee up the conversation in a way that doesn’t make the other person defensive. “We need to talk” is a terrible way to start. Instead, start with facts that the other person agrees with.

Example: “Phones start ringing every day at 8:00.” “Three times in the last two weeks, you weren’t logged in.”

The emphasis matters. Don’t emphasize “you.” Emphasize the behavior. Then tie it to impact: “When calls roll to voicemail during business hours, our reputation for excellent customer service is on the line.” Now it’s not about blame. It’s about the bigger picture.

Step 3: Listen and Let Silence Work

Janel: After stating the issue, stop talking. If needed, invite them in: “I’d love to hear what’s going on for you.” Then be quiet. Silence feels uncomfortable, but it’s where thinking happens. If you interrupt it, you kill the process.

Handling Excuses and Deflection

Janel: If they start bringing up unrelated issues: “If we need to have a conversation about transportation, we can. But right now, I need you to understand what’s at stake.” Keep bringing it back to the core issue.

Steps 4 & 5: Expect the Unexpected & Co-Create a Solution

Janel: As you listen, new issues may surface. Be ready for that. Don’t assume you already know the problem or the solution. Don’t prescribe the answer. Build it together. Ask: “What ideas do you have for how we might address this?” Even if the first idea is bad, stay neutral. “Interesting.” Keep adding ideas together, then evaluate them.

Step 6: Schedule a Follow-Up

Janel: Once you land on a solution: “Let’s try this for two weeks, then check in.” Put it on the calendar immediately. This creates accountability and gives you a chance to reinforce what’s working.

If the Conversation Goes Sideways

Janel: If things get heated: “I think this is as far as we’re going to get today. Let’s take some time and come back to this.” When people feel threatened, stress hormones take over. You won’t solve anything in that state.

Handling an Upset Customer

Janel: Upset customers are high intensity and negative. If you tell them to calm down, you’ll make it worse. Instead, match intensity briefly: “That must be really frustrating.” Then guide the tone downward. This uses mirror neurons. People tend to follow your emotional lead.

Some people just want to vent. Ask: “Are you looking for solutions, or do you just need to vent?” You can also set boundaries: “I’ve got five minutes right now. Tell me everything.” Use a timer if needed. Then offer solutions afterward.

Handling a Vendor Falling Short

Janel: Start from agreement: “Our relationship is really important to me.” Build facts: “The last three orders had discrepancies.” Avoid “but.” Use “and.” “I thought we had that fixed too, and it turns out we didn’t.” This keeps you on the same side of the problem.

Closing Thoughts and Resources

Janel: There’s a quiz to identify your pattern in difficult conversations — Improviser, Avoider, Escalator, or Deflector. Find it at janelanderson.com/hard-conversations-quiz.

Shawna: Dogs or cats?

Janel: Dogs.

Shawna: What is that other species? Cats belong in yoga, cat-cow pose. That’s where they belong. Thanks for listening. This has been Underestimated, and we’ll see you next time.