When an employee isn’t doing what you need them to, it’s tough. You know you need to say something, but you don’t want to make it worse - like making them get defensive or feel like they’re failing altogether. And definitely not making them cry. But no one ever told you how to actually have these conversations.

So, most managers… just wing it.

If that’s you (or managers in your organization), you’re not alone. Most managers haven’t been trained on how to have these conversations. But with a few tips, you can support someone without micromanaging or making it awkward. In fact, the way you show up in these moments might be the most important part of your role.

In the video below - and in the tips that follow - you’ll find the reminders you’ve been looking for.

1. Take a Breath and Ask Yourself: What’s the Goal Here?

Before you say anything, pause for just a moment. Take a breath - not to delay the hard part, but to reset.

Ask yourself: “What’s the goal here?”

Is it to check a box? Do what you "have to" to get them off your team, or the organization? Or is it to genuinely help this person get back on track?

When you try that way of thinking - care, not "casting off" or control - you come across calmer, more supportive and more likely to get to the root of what’s going on.

Manager tip: Even a 10-second pause before the meeting can help you be more grounded, so the conversation feels supportive, not punitive.

2. Ask Questions Before Telling Them What to Do

Instead of jumping straight into what’s going wrong or what you think they should do next, take a moment to be clear about why you’re having the conversation - and then ask questions (and keep asking). Your team member’s first thought is probably, “Wait, what's this about?” So, being upfront (instead of vague) helps the conversation be more productive. But just as important is taking the time to listen. They might be dealing with something you didn’t see coming - and the only way to really understand is to ask.

An example is:

“I wanted to check in because I’ve noticed some things seem off, and I really just want to understand what’s going on so we can get to the bottom of it together. I'm here for you when things seem easy, but also when they don't. From your perspective, has anything been feeling harder than usual or different day to day?"

You can always adjust this for your voice and the situation, but it helps to have a place to start. Being clear about why you’re talking - and then truly listening - can set the tone for a more productive conversation and help keep the other person from immediately feeling defensive.

And if you want help phrasing it, try a ChatGPT prompt - I'm including an example in my weekly Manager Method Minute email (if you don't get them in your inbox - no worries, I include a link at the end of this blog where you can sign up).

3. Reiterate Why You're Having the Conversation

This part matters more than you might think.

Many people assume the worst when a manager asks to “talk.” They may have had experiences where performance conversations felt like punishment, not support.

So make it clear from the start:

“I know these conversations can feel uncomfortable - but they’re important. I want to help you in this job and in your career, and that means being honest and supportive when things feel off. I also really want to hear your perspective, because this should be a conversation, not just feedback coming at you.”

How you approach the conversation can greatly impact how it’s heard. That’s why it’s important to reiterate why you’re talking - to build trust and help the conversation be more productive.

4. Let Them Lead the Plan - Then Offer Support

Once you’ve talked about what’s going on, it can be tempting to jump in with your own ideas or just tell them what to do next. That can feel like the best option when you're busy. But taking just a few more minutes can make a far longer-lasting impact.

Ask them:

• “What are some different approaches you could take, and how might each one play out? I’m here to support you, but I have confidence in your judgment - I’d love to hear your thoughts first."

By letting them suggest ideas first, you’re sending an important message: I trust you. I believe you know yourself and your work. And I’m here to support you - not take control.

Then, you can build on what they suggest by offering support or ideas. For example:

• “Would it help to talk more about this - now or maybe Monday?”

• “If you’re not sure how this fits with everything else on your plate, let’s talk through it.”

• “Let’s check in on how this goes during our next 1:1.”

This gives them the opportunity to try something new, while also committing you to follow through. Add a quick note to your shared agenda or set a calendar reminder for yourself so you do actually bring it back up. Checking in is a small step a lot of managers forget (because you're human), but it goes a long way in showing you’re not viewing the conversation as a check-the-box.

5. This Could Be One of the Things You Remember Most in Your Career

Supporting someone through a tough moment isn’t easy - but it’s often these moments that leave a lasting impact throughout your career. That’s why it can help to get a few tips to make them a little easier.

When you handle a tough conversation with care, you're not just getting through it - you’re building your leadership skills. And you're making an impact on someone who needs it. You might not remember every meeting or project down the road, but you'll remember the time you made someone feel seen and supported. And they will, too.

Final Thought: You Don’t Have to Wing It

If you’ve ever thought, “I’m not sure how to say this,” or “I hope I don’t make it worse,” you’re not alone. That’s exactly why I create resources like this blog and Manager Method trainings. To help you have examples of what to actually do and say - to drive performance without driving team members out the door.

Want weekly tips like this? Subscribe to the Manager Method Minute - get a bonus tip every week in our email.

Need practical tools that help you run better 1:1s, give clear feedback and handle tough moments without second-guessing yourself?

Manager 101 gives managers the practical guidance they need on the real challenges they face—whether you're grabbing it for yourself or rolling it out across your organization. If you’re in HR or on the People team and your managers are flying blind, we’ve got their back - with scalable, customizable training that’s easy to implement and actually sticks.

Want to explore what this could look like for your organization? Schedule a call here.