#91 | 4.18.25 - How to Have The Hard Conversation / The Most-Read Book Genres in Every State / Your Life in Months / Plot the Path of a Raindrop
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How to Have The Hard Conversation
I’ve been reflecting on this topic for the last several weeks, as it’s come up in several conversations. I don’t think I’ve met anyone who enjoys having hard conversations - probably why they’re named the way they are. But we’re not alone - according to a recent study, 70% of employees completely avoid them.
With the acknowledgment that, yes, these conversations are hard, we still need to be able to lead in this area, and I believe the ability to navigate these conversations effectively is one of the most valuable skills we can develop.
Here's a quick, step-by-step approach to having hard conversations in a way that builds relationships rather than damaging them.
1️⃣ Pause
Take time to ensure you’re not emotional. Pausing is a deliberate choice you can make that shifts your behavior from reactive to proactive, enabling you to act purposefully and with the intention you set.
Make sure your goal isn't to punish, shame, or "win." The best conversations aim for mutual understanding and resolution.
2️⃣ Schedule The Meeting - Soon | Short | Private
Soon - As soon as you’re calm and collected, schedule the meeting. As a friend of mine reminds me, “Delay = drama”. Give the person a heads-up about what you want to discuss. Also, be kind to the person you’ll be talking to, and make sure there’s no significant gap between when you send the invite and the actual meeting. I recommend no more than 48 hours.
Short - Set the meeting for long enough to dig in, but short enough to stay focused and not belabor the point. For most conversations, I recommend 25-30 minutes.
Private - Probably goes without saying, but find a quiet, private room where neither party feels cornered.
3️⃣ Plan, but Don’t Over-Plan
Be clear on what you want to get across. Make notes, but don’t write a script. Writing out notes is there to remind you of what you want to get across. The goal should be authenticity and genuineness.
4️⃣ Have the Conversation Using the S.A.N.D. Method
This is one of my favorite methods to have hard conversations:
🚫 Don’t have the conversation over text/teams/slack. As I’ve said before, don’t do conflict over a keyboard.
5️⃣ Listen with Curiosity
To quote Walt Whitman:
“Be curious, not judgmental”
Remember to give them space to process the information and then respond. Like the great Ted Lasso reminds us, dial up your curiosity, and listen. A few specific tips that help me:
Mirror key points. “I’m hearing that supplier delays were the core issue—did I get that right?”
Label emotions. “It sounds like you’re frustrated with the current process.” (Naming feelings defuses them.)
Silence ≠ weakness. A few seconds of quiet let insights surface; resist filling every gap.
6️⃣ Come To A Resolution
End the conversation, ensuring each person is clear on next steps and accountability.
What will they do and by when?
What will you do and by when?
7️⃣ Follow-up
Within 24 hours of your conversation, schedule a follow-up discussion for you each to talk about how things are going.
As they improve, recognize and call out their improvements, even the small ones.
If they don’t improve, help them recognize that it’s not getting better and what the next steps are.
The most meaningful relationships in our lives aren't the ones free from conflict—they're the ones where conflicts are addressed with honesty, empathy, and mutual respect. 😀
The Most-Read Book Genres in Every State
I thought I would get this right for my home state of Montana. Nope, I didn’t. 🤣
Your Life in Months
I enjoy a good visualization, and this site is no exception. You can also break it down to weeks and years.
Plot the Path of a Raindrop
This cool website allows you to plot the path of a raindrop anywhere on Earth to see where it ends up. Definitely worth checking out.
Your words will tell others what you think. Your actions will tell them what you believe.
- T.D. Jakes