How to Have the Tough Conversations: 3 Shifts to Make Tough Conversations Feel Manageable
Change is hard - Employ These 3 Shifts to Make It Easier
Adjusting how you approach stuff can be a big change. In the past few weeks, we’ve talked about how important it is to not avoid the tough conversations and to give you and your team the chances you both deserve to grow. And, well, be better so you can do better.
This week, we’re talking about 3 easy shifts to make those tough conversations a bit more bearable. Or manageable. Or approachable.
1. From Punishment to Partnership
Old thinking: "I need to tell them what they're doing wrong."
New thinking: "How can we solve this together?"
The goal isn't to make someone feel bad about their performance. It's to partner with them to find solutions that help them succeed.
2. From Perfect Timing to Good Enough Timing
Old thinking: "I need to wait for the perfect moment to have this conversation."
New thinking: "The best time to have this conversation was last month. The second-best time is now."
Perfect timing is a myth. Good enough timing with genuine care and intention is always better than continued avoidance.
3. From Protecting Feelings to Protecting Growth
Old thinking: "I don't want to hurt their feelings or make things weird."
New thinking: "Not giving them this feedback is actually limiting their potential."
The kindest thing you can do for someone is give them the information they need to succeed. Withholding feedback isn't protecting them—it's holding them back from growth they deserve.
Start Small: 3 Conversations You Could Have This Week
If the idea of addressing everything at once feels overwhelming, just pick one of these:
1. Give someone specific recognition
Pick one person who's been doing solid work and tell them exactly what you've noticed. Be specific about the behavior and why it matters.
"I wanted to mention that the way you handled that client concern yesterday was really excellent. You stayed calm, asked thoughtful questions, and found a solution that worked for everyone. That's exactly the kind of problem-solving that builds real client trust."
2. Address one small thing before it becomes a big thing
Think of someone who has a minor performance issue that could grow into something bigger if you keep ignoring it. Have a quick, supportive conversation.
"I've noticed you've been running a few minutes late to our team meetings lately. Everything okay on your end? I want to make sure you're not missing important stuff at the beginning."
3. Just ask how they're doing
Check in with someone about their actual experience at work and what support they might need.
"How are you feeling about your workload these days? Are there areas where you'd like more challenge, or places where you could use more support?"
The Bottom Line
Every single day you put off a difficult conversation is another day that problems get bigger, trust gets weaker, and opportunities for real growth slip away.
But every difficult conversation you have with genuine care and intention? That's an investment in your team's success, your own growth as a leader, and the kind of workplace culture you're building together.
That conversation you've been avoiding? It's probably not nearly as hard as you've built it up to be in your head. And the cost of continuing to put it off is definitely higher than the temporary discomfort of just having it.
Your team is waiting for you to step up and lead. They're hoping you care enough to have the conversations that actually matter.
So what conversation are you going to have first? Download our free toolkit to help you get ready.