Eventually in your career as a manager, you'll have to sit down and have a candid conversation with an employee who's frustrated or unhappy. They might be upset with a colleague, disappointed about a performance review, or misaligned with the team or company direction. Whatever the case, approaching these difficult conversations is never easy, even for the most experienced manager.

When you have to deal with a difficult employee, one of the first things you should do is schedule a one-on-one meeting with them to talk things through. Having direct, honest conversations with your team members is a part of the job and crucial when challenges arise.

With a little bit of planning, you can make a one-on-one meeting with a difficult employee constructive, and lead this difficult discussion to a productive outcome.

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How to manage a difficult employee in a one-on-one meeting

Whether there's been a misunderstanding, conflicts between employees, or you sense something is off with one of your direct reports, you want to address it directly. A one-on-one meeting is the best place to deal with an unhappy employee because it's in a private setting, and you've created a dedicated time and space to address the situation.

These pointers on managing a difficult employee in a one-on-one meeting help you show up prepared and carry out the conversation more effectively.

Schedule the one-on-one meeting

First and foremost, you have to book a time to meet with your employee. Schedule your meeting time with enough notice that both of you can prepare, but don't delay difficult conversations with employees. The best timeframe is somewhere between a few hours and one business day in advance. Any more than that, it could cause anxiety or frustration to build. Any less, and they could feel like they're being put on the spot.

Tip: Send the meeting invite out during the first half of the business day. If someone sees an invitation come through right before they log off, it could weigh on their mind through the evening. But if they get it in the morning, they have time to process it through the day and reach out to you with any questions.

Set a meeting agenda

Send your employee a clear meeting agenda with the talking points you want to discuss. Even if you both know what the conversation's about, having it written down will help ease their nerves and let them prepare. Establish it as a two-way conversation from the start by letting them know that there will be time for them to bring up their own talking points or questions.

Tip: If you're unsure how to structure this type of discussion, a one-on-one meeting template for difficult conversations could help.

Enter the conversation with an open mind

It's unlikely that a tough conversation will turn productive if you enter it with the mindset that you're dealing with a toxic employee. Try to avoid making assumptions about what's made a person unhappy or why they're acting a certain way. You never know what might be going on behind the scenes or in someone's personal life. A positive approach makes a big difference in where the conversation will go, so work to break down your preconceived notions before you start a tough talk and make understanding your goal for the one-on-one meeting.

Tip: Even the most positive people have bad days, so give your employee the space to vent or decompress if they need to. While you might want to move the conversation into the next steps, sometimes people need to lay everything out before they can start to action plan.

Figure out why your employee is frustrated

When you're having a difficult conversation at work, it's good to start by trying to understand the other person's perspective. Ask your employee to share their experience and view of the situation. As you listen, try to understand what's behind their bad attitude or frustration. When you approach the discussion with empathy and understanding, the other person will be more open to sharing how they really feel.

Tip: Try asking an open-ended one-on-one meeting question like 'What's been causing you stress lately at work?' or 'How are you feeling right now on the team?'. Avoid asking a direct question that could seem confrontational, like 'Why do you think I called this meeting today?'

Acknowledge what they share with you

Whether or not you see things in the same light as your employee, you want to let them know that you've heard them and understood what they've said. Acknowledging someone's perspective doesn't have to mean agreeing with it. A simple 'I hear you' before you respond lets your team member know that you're really listening, and not just waiting for your turn to talk.

Tip: Sometimes, it can be helpful to echo back what you've heard from the other person. But be mindful of when you choose to do this. If someone is agitated, they might take this as you reframing their perspective in a negative light or putting words in their mouth.

Focus on performance, not personality

Whether or not it's an official performance review meeting, focusing the conversation on employee performance helps you keep it grounded in facts. When you slip into subjective opinions on how work should be done — or worse, take a judgmental approach — it's difficult to have a productive, meaningful conversation that leads anywhere. So try to ground a conversation with an underperforming employee in something concrete. Discuss their goals, deadlines, and other objective measures of performance.

Tip: If an employee is on a performance improvement plan, aim to support their performance development more than monitor their progress. A manager's role is to empower and help an underperforming employee, not micromanage them.

Give constructive, direct feedback

Sometimes managing a challenging employee means delivering negative feedback on something they've worked on or their behaviors. When you give tough feedback, you want to make sure that you're honest, direct, and most importantly, kind. Especially when you're giving behavioral feedback, it's important to be sensitive and avoid letting your frustration get in the way of being constructive. Your words have a real impact on people, so choose them mindfully.

Tip: Before you give honest feedback, ask yourself: What is my intention with this feedback? What outcome do I hope to come from sharing it? How could the other person apply this feedback in the future?

Get to know their career goals

Often, employees become dissatisfied when they don't see a future for themselves in their job. As a manager, you should be the go-to person for your team member when they feel uncertain or misaligned in their roles. But if you don't have a strong understanding of their career goals, it's hard for you to play that role and coach employees towards success. Excellent managers find the overlap between business needs and employee ambitions and set their team members up to move both the team and their career forward.

Tip: Every 3-6 months, sit down with your direct reports and talk about their career development. Discuss how they might make strides towards this bigger picture in their current job and how you can coach them in your one-on-one meetings to get there.

Take meeting notes throughout

You want to keep track of the one-on-one conversations you have with employees, especially when there's tension or you address any problematic or bad behavior. Having a clear record of what you've discussed helps you follow up in your next conversation. And if ever you need to address a pattern of behavior with an employee, you'll have concrete examples to draw from. Ideally, you'll be able to work through things together in your one-on-ones. But if you ever need to consult with your current HR managers, it's important to have meeting notes.

Tip: A one-on-one software like Officevibe can help you centralize your meeting notes so you have a record of your conversations with each employee on your team. You can create shared one-on-one agendas and action items and keep private meeting notes in the app that only you can see.

Close out with a conversation recap

Finally, the best way to end any one-on-one meeting with an employee is to recap the key talking points you went over. Save 5-10 minutes at the end of your discussion to share your takeaways and ask them to do the same. Based on this, you might set an action item or discuss a corrective action that your employee (or you) can take to address the situation. Either way, be sure to align and take a breather together so you both walk away feeling more on the same page and ready for the future.

Tip: Follow up the conversation by sending your employee some bullet-point notes of what you shared and what you heard them share during the meeting. Include subjects to check in on in your next one-on-one and ask your employee if there's anything you missed.

All managers will eventually have a one-on-one with a difficult employee

You're not alone in this, and you may not get it perfect. The most important thing is to adopt the right mindset and approach a difficult discussion with the intention of walking away with a little more understanding. When you treat your employees with respect, they'll do the same. And this makes even the most challenging conversations a little bit easier.

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