Having difficult conversations: a manager’s guide to tough talks

What to say and how to follow up, so even the toughest conversations lead to productive outcomes.

Being a team leader is an incredibly rewarding role—but like any great job, it comes with its challenges. Part of that is having difficult conversations with employees. Do you have the skills to tackle tough talks? Whether it’s about poor performance, team conflict, or personal issues, dive in to see how you can handle a tough conversation with a team member. 

Having difficult conversations: do’s and don’ts

Preparing for a productive conversation

Knowing that you need to have a constructive conversation with an employee on your team, you want to take the time to plan what you’ll say. Start by scheduling one-on-one meetings and set the talking point in your meeting agenda so you both have visibility on what you’ll discuss. Use a shared agenda so employees can add their own talking points, too. Of course you want to arrive prepared, and your team member should have the chance to do the same.

Write down the key points you’d like to address, and practice how you’ll say them. Seek out someone you trust as a sounding board before having difficult conversations (but be mindful of what information you share). It’s easy to get so caught up in what we want to say, that we forget to think about how it will land.

Put yourself in their shoes: Take a moment to imagine that you are on the other side of the situation. Consider 3-5 possible emotions your team member might have. Could they be disappointed? Frustrated? Jealous? Embarrassed? Remember that you don’t know what they think or how they feel, and go into the conversation seeking to understand.

3 top tips for having difficult conversations

1. Focus on facts, not emotion

Part of this comes in your planning; you want to sort out the facts of the situation from how you feel about it. Having this clearly laid out helps keep a challenging conversation focused and grounded. You can even bring notes, or if you’re using Officevibe, add personal notes to your one on one tool agenda that are visible to you only :

• What happened to warrant a difficult discussion?
• What is the impact?
• What needs to change or be adjusted?
• What will happen if not?

When you know the answers to these questions you avoid speaking in hypotheticals or getting sidetracked. That way, you’ll talk about what really matters, and not end up in an unproductive debate over something subjective.

Don’t ignore how you feel: it’s only natural for emotions to arise when there’s tension or something important is at stake. When you’ve nailed down the facts, it’s easier to manage your emotions and keep a hard conversation on track.

2. Create an environment for honesty

When one or both people enter a conversation with reservations or a negative attitude, it hinders the potential to reach a positive outcome. Open the conversation by stating your positive intent, whether it’s conflict resolution, understanding, or creating an action plan. You can try asking coaching questions in your one-on-one to give your team member the chance to express themselves.

You also want to foster a culture of honesty and openness with employees on an ongoing basis. Recurring one-on-one meetings with each member of your team let you to touch base and discuss what matters most. With Officevibe’s one-on-one software, you can build a shared agenda where you and your employee can both add talking points. Then, set trackable action items that carry over week to week. Centralizing your one-on-ones makes them quicker to plan each week, simplifies your yearly reviews, and helps everyone follow through on commitments made.

3. Come up with a solution together

At the end of any difficult discussion, you want to establish some next steps so that you and your employee are both clear on expectations moving forward. There may be times where action items are predetermined, but when they’re not, it’s best to discuss possibilities together and agree on what makes the most sense. This means letting go of any preconceived notion that you know what the best path forward is, or that your direct report must come up with it on their own.

Being the kind of manager who makes themselves a part of the solution is one of the best ways to lead by example. When employees see you implementing meaningful change, they’ll follow suit. Offer up any ideas that you have, and be open to your team member’s ideas as well. Be ready to pitch in or take responsibility for some of the action items you set.

Following up after having difficult conversations

What’s the purpose of action items if we don’t follow up on them? After having difficult conversations, follow-through is especially important because you want to see the issue resolved. Set a talking point for your next one-on-one to make sure the tough talk leads to the desired outcome. Officevibe’s one-on-one software lets you set action items together, so it’s easy to track the efforts your team member is making.

Beyond following up on practical matters, make a point of checking in on a more personal level as well. Talking about sensitive or contentious subjects can be upsetting or awkward, and it’s good to reconvene once the dust has settled.

Follow-up questions to ask:

• How are you progressing on the action items we set last time?
• Is there anything on your mind from our last one-on-one?
• Do you have any thoughts or questions about our last discussion?
• How are you feeling since we last spoke?

Difficult conversation examples: real-life scenarios

These difficult conversation examples apply the best practices from this guide to real-life scenarios.

Managing peer conflict

“I sensed some tension in our team brainstorm yesterday, and I’m curious to hear your perspective on it. It’s natural that we won’t always see eye-to-eye with each other, but respect is a non-negotiable team value. I want to make sure we address any friction before it impacts our collaboration.”

Dealing with difficult behavior

“I’ve noticed that when you challenge people’s ideas you don’t always offer an alternative solution. It’s okay not to have the answers, but it can come across as though you’re simply shutting others down. I wanted to bring this up with you because I know you care about the team’s collective success. How can we make these conversations more productive?”

Dealing with a troublesome teammate? Read our complete blog post on how to deal with a difficult employee.

Addressing underperformance

“You haven’t been hitting your targets lately, and I want to make sure you have everything you need to succeed. Are there any processes we can review together? Do you think having coaching sessions would help? Let’s walk through your workload to make sure you can prioritize your most impactful tasks.”

Letting a member of your team go

An unfortunate reality of people management, letting an employee go is never easy. Our complete blog post on how to fire an employee with empathy and support your team offers tips to manage this difficult situation.

“I’m sorry to say that because of [name the reason they are being fired], we have to let you go. Thank you for everything you’ve accomplished over the last [state how long they’ve been employed]. We really value the work you’ve done on the team and for the organization.”

Tip: If you’re prepared to, offer to be a reference for them in their job hunt.

Discussing employee personal issues

“Let me know if you’re not comfortable discussing it, but I noticed that you seem a bit down these days. Do you feel you have enough work-life balance? Is there anything going on that I should know about, or that I might be able to help with? I want you to know that I’m here for you, as your manager and as a friend.”

Discussing a difficult topic at work is tough for any manager. The more comfortable you get, the more each uncomfortable conversation will lead to a successful outcome. If you can keep an open mind and approach awkward one-on-ones with curiosity, you’re sure to get employees on track to succeed as a team.