We’ve all done it. You re-read the Slack message, you think about it at 3am, you swear today will be the day you bring it up, and then… you decide tomorrow's the day. Spoiler alert: it's not.

As a manager, difficult conversations at work come in all shapes - managing someone who's a personal friend, telling someone their performance isn’t what's expected, or telling another senior leader that their "leadership" is stressing out your team. Without a doubt, it's way easier to overthink or delay a hard talk than to actually have it. But that doesn’t help your team - or you.

So, here’s a sneak peek at how we're helping make those conversations happen in a way that’s human, clear and (dare we say!) effective (with tips below).

1. Actually Have the Conversation

This sounds obvious, but it’s where most people get stuck. We delay, hint or talk to everyone but the person we need to. But avoidiing the conversation just drags out discomfort, erodes trust, and often makes the issue worse. It’s not kinder, it’s just quieter - and silence usually feels louder to the person on the receiving end.

Before you say anything, take a moment. Literally - pause. Breathe. Then, commit to the idea that you’re going to have the conversation. That’s the first, and often most important, step.

2. Think About Them, Not Just You

When prepping, most of us get stuck in our stress - how awkward it’ll be for us, how they might react to us, how we’ll come off. But a powerful shift happens when you instead consider the other person’s perspective.

• What might they be going through?

• How would you want to be treated if you were in their shoes?

• What would help them hear this clearly, without feeling attacked?

This doesn’t mean watering things down. It means approaching by being clear and respectful - which often leads to better outcomes and working relationships.

3. Be Personally Clear on What You Want to Come Out of It

If you go into a conversation without a goal, you’ll likely come out of it with confusion (and they will, too). Don't wing it. Before you sit down, ask yourself: What do I want to be true after this talk?

• Do I want a behavior to change?

• Do I want us to be more aligned?

• Do I need to set a boundary or provide clear expecations?

Once you know that, you can “back into” the conversation. Think about the opening that will get you there without defensiveness or rambling. Example:

“I wanted to talk about our team meetings so that they're as collaborative and productive as possible. I’ve noticed you often jump in to lead the discussion right away, and while I know that’s coming from a good place and you have experience, I think it might unintentionally be discouraging others from speaking up or adding in their ideas. I’d love to work on creating more space for everyone.”

You don't need to give a TED Talk - just focus on the result you’re looking for and communicate in a genuine, human way.

For Managers: A New Tool to Help You With the Conversations That Matter Most

Difficult conversations don’t get easier - you just get better at them. And we want to make sure managers have the tools to do exactly that.

That’s why we created a brand-new bonus module in our Manager 101 course focused entirely on Difficult Conversations. This supplement goes deeper than just “what to say.” It walks through 13 of the most common types of tough conversations managers face - like addressing performance concerns, resetting expectations, navigating interpersonal tension, and even productively "managing up" when you need to.

Just like all modules of Manager 101, we pair short, conversational videos with a companion Resource Guide that’s packed with:

• Sample language and talking points

• Common traps to avoid

• What to keep in mind before, during and after the conversation

It’s designed to layer on top of the already-popular Manager 101 content, giving you even more practical tools you can use immediately - whether you’re managing your first team or your fifteenth.

Because the conversations you’ve been avoiding? They’re often the ones that matter most. And now you’ve got backup.

Want to explore Manager 101 for yourself or your managers? You can get instant access for yourself or learn more about organizational packages for a group of managers at managermethod.com/manager-101.