10 Tips for having difficult conversations with employees

At work and in life, we all have to face difficult conversations. For managers, having tough talks with employees can have a big impact on their engagement, development, and the relationships you have with each member of your team. That can feel intimidating, but these tips for having difficult conversations with employees will help you make tough discussions truly productive. That way, you and your employee both walk away with a little more understanding, and a much clearer sense of what comes next.

Tips for having difficult conversations with employees

A difficult conversation could be about anything from employee personal issues, to performance troubles, or peer conflict resolution. You might even have to address difficult employee behavior directly. Whatever difficult topic you need to discuss, these tips will help you have a more productive conversation.

1. Schedule an appropriate time 

When having a challenging conversation, be sure to schedule a time to meet in person or over video chat. If you’re communicating delicate information, all the nonverbal cues and body language that help deliver your message may be lost when typing through Slack or email.

Schedule a one-on-one meeting with your employee. Set a few talking points in the agenda so you both know what to expect, and ask your team member to add some talking points or questions, too. Of course you want to arrive prepared, and your team members should have the chance to do the same.

2. Plan your conversation 

In a tough conversation, you don’t want to appear to be communicating on the fly. It’s important to be intentional with what you say, and have your key points prepared. One great way to plan your discussion is to use a difficult conversation framework. You don’t need to have an entire speech planned, but take the time to write down what you’d like to get across.

Make sure to give yourself 5-10 minutes to prepare the broad strokes of what you’d like to say. Practice saying the difficult points out loud before you meet with your employee. A little bit of thinking ahead will go a long way when it comes to delivering these challenging messages! 

3. Stick to the facts 

When thinking through your talking points, it’s always important to stick to the facts. Point out observable behaviors, and explain the outcome or result of what you’re sharing. The most important thing is to leave emotion and personal attacks out of the conversation. Laying out the facts ahead of time — and weeding out anything subjective or unproductive — helps you manage your emotions during the discussion.

4. Flex your empathy

As a manager, practicing empathy is one of the greatest ways to connect with your team. Especially when you’re having a hard conversation, don’t let professionalism overpower your humanity. As you prepare and deliver a difficult message, make sure to put yourself in your employee’s shoes. Take a moment to imagine that you are on the other side of the situation.

Having empathy for yourself is equally important, so don’t ignore how you feel. It’s only natural for emotions to arise when there’s tension or something important is at stake. Remind yourself that challenging conversations, are challenging. Give yourself a few mindful breaths before the conversation, and go for a walk or decompress once the conversation is done. 

5. Be honest, and be open

To make space for your employee to be honest and open with you, you need to be honest and open with them. Respecting someone enough to be upfront with them shows that you care, so be direct with what you have to say, but always be compassionate. You might even start the conversation by telling them your positive intent.

Vulnerability and an open mind can really help move the conversation along. If an employee made a mistake, you might open up about a time that you made a mistake too to show them its okay. Or if they failed to reach a deadline, you could tell them about a time when you dropped the ball and what you learned from it. A big part of building trust is opening up and being vulnerable.

6. Check for a common understanding

Check in throughout the conversation, and at the end to make sure you’re both on the same page and understanding each other. This means asking them to explain what they’ve understood, but also asking them to explain more what they’re saying. The point is for you both to hear each other out, a conversation shouldn’t be one-directional.

“The single biggest problem in communication is the illusion that it has taken place.”

George Bernard Shaw

7. Brainstorm solutions together

Try to let go of any specific plan you have for the best path forward and open it into a two-way conversation. Ask your employee what they think would be the best course of action or if they see an opportunity to make a change. Of course, share your ideas as well, but bring them up as possibilities rather than assignments.

If there isn’t necessarily a solution to be determined, make sure you discuss learnings. What can be gained from the situation, and what might apply to your future work or planning? There might be an opportunity to share what you’ve discussed with your team or your own boss. Just be sure to give time to a discussion around what comes next.

8. Build an action plan

Once you’ve discussed some possible next steps, decide on a few that make the most sense to you both and create an action plan together. Write down some action items and come up with a timeline for following through. You might consider setting a goal for your employee.

Be open to taking on some action items, too. There might be things you can do as a manager to be a part of the solution. Whether it’s talking with another team member, accessing resources, or connecting them with someone else in the organization, offer to help.

Details matter! Decide on who will do what, when, why, and how.

9. Follow up on agreements

Whatever action plan you create, be sure to touch base with your employee soon after your difficult discussion. Even if you don’t set specific action items, it’s good to check in at your next one-on-one meeting to see how your team member is feeling, and how things are progressing.

It’s also important to hold yourself accountable to the commitments you made. If you told your employee you’d reach out to the HR department, let them know what you found out from that conversation. If you offered to take on a task, tell your team member when it’s complete.

10. Develop your feedback culture

The human brain is like velcro when it comes to negative feedback and hard conversations. Employees may be doing a great job in other areas, but when they hear something negative about them, it can stick and hurt their morale which can then decrease their engagement.

If you create a culture of feedback on your team, then having hard conversations won’t feel so out of place. Make it a regular practice to share both positive and negative feedback with your employees during one-on-ones. That way, they won’t feel as shook or worried when you do have something constructive to share with them.

Make difficult conversations easier and more productive

With these tips for having difficult conversations with employees, you’re sure to turn every tough talk into a positive outcome. No matter what needs to be discussed, and how difficult it may be, you can show your employees that you care and support them in moving forward with confidence.

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