Three Hard Conversations Every Manager Needs to Have

Communication is key to being a good manager. When your responsibilities include hiring, training, scheduling, directing, rewarding, and disciplining a team of people—your peers, if you were promoted internally—having difficult or challenging conversations can be a daily occurrence. Being able to connect with people and discuss important issues in a positive, constructive way is a pretty crucial skill for anyone, but one you’ll definitely need if you’re hoping to be successful as a manager.

Among many others, three conversations stuck out to us as practically unavoidable for any manager. If you’re hiring, it’s likely you’ll also have to fire someone at some point. Unless all your employees are perfect, you’ll have to address a performance or behavior issue. And if you follow good performance management habits, you’ll have to check in with people on a semi-regular basis. All of these conversations might seem challenging at first, and anything involving disciplinary action will likely remain somewhat daunting forever. That said, if you can keep your head straight and the following tips in mind, you’ll have an easier time sitting down for these discussions.

How to discuss termination

Believe it or not, informing someone about their termination isn’t as hard as you might think. We don’t mean to sound heartless or cruel; it’s never an easy conversation. But assuming you’ve followed all the right steps in determining your reasons for and right to termination, the interaction should be relatively straightforward if you follow these three steps:

Don’t explore the “why”

This is probably the toughest rule to follow, because our instinct as the person inflicting harm is to explain away what might seem arbitrary or cruel. Be kind, be gentle, be considerate, but don’t get into a discussion about why you’re letting someone go. Simply tell them that the decision’s been made and that parting ways is the best thing for them as well as the company. If you never get into the reasoning, you’ll save yourself from any argument and you’ll be much less likely to say something that creates cause for disputing the termination.

Have your ducks in a row

Are there keys or keycards to collect? A laptop or other property to turn in? Documents to sign? A severance package to award? Know the answers to these and any other questions beforehand, and prepare in advance so events move swiftly and efficiently. Even though it may seem like a good idea to get it over with as soon as possible, the last thing you want is to leave issues unresolved or have to ask an employee to come back for some reason. Even if you separate on good terms, they’ll likely be annoyed or reluctant to return.

Bring backup

Unless you’re in HR yourself (and even if you are), it’s advisable to have a representative from your HR or legal team present during the conversation. This is for two reasons: first, they’ll be versed in the rules and consequences of proper and improper termination, which provides a safety net for you. Second, while it might seem overly cautious, having a second person in the room protects you and your organization from damaging effects, whether from physical violence or false testimony.

How to Manage Three Challenging Conversations at Work

Things get trickier when it’s time to talk about an employee’s poor performance or inappropriate behavior. There are rules to follow just like there are for termination, but with one big difference: you have to maintain a working relationship with the employee. That means the conversation needs to do more than just inform; it also needs to provide next steps to follow for the people involved.

Focus on the positive

Unless there’s a serious miscommunication, the negative side of any performance or behavior conversation will be pretty clear from the time you inform them why it’s happening…or it will be when you talk about documenting the incident. To maintain balance and preserve good relations, dwell on the upsides as much as possible: you value their contribution, and you’re offering them a chance to correct or improve their behavior so they can continue as a member of your team.

Don’t make assumptions

It’s not your place to wonder at the root cause of whatever brought you and your employee together for this talk, even if you’re certain you know the reason. If they want to bring it up, that’s fine. But suggesting a reason leaves you open to liability; you might guess wrong and cause offense, or you might even provide an excuse for them to claim protection under the ADA. And if you’re not familiar with the ADA, read up on it, because if the reason they provide falls under protection, you’re responsible for reporting it.

Leave paperwork until the end

If you want to guarantee an employee will miss some or most of a conversation, hand them a piece of paper at the beginning and tell them it’s going in their file. Yes, it’s likely required that you document any performance issues or disciplinary action, but producing physical documentation up front can weigh heavily on the conversation. Unless your policy requires the paper to come first, better to talk about what happened and what the plan is for the future before you serve up the slip. Let them read it on their own. If they have questions, you’re going to follow up anyway, right?

How to have regular check-ins

Why would anyone feel nervous about something as benign as a status meeting? Well, it may surprise you to know that many people get nervous about any kind of one-on-one, whatever the reason or role they may be playing in it. But regular check-ins are a critical part of good performance management; they offer a chance to praise great work, and an opportunity to uncover and resolve issues before they get too complex. So the question isn’t whether to have regular check-ins, it’s how to do them right.

Take it easy

Whether it’s social anxiety or a Pavlovian response acquired after dozens of childhood visits to the principal’s office, for some of us the prospect of a face-to-face can be stressful to the point of nausea. If you’re a manager, it’s something to remember even when you think everything’s hunky-dory. Kick things off with a smile, be clear about the nature of the meeting (even if it’s on the calendar like it should be), and finish with an encouraging message.

No surprises

Check-ins should happen on a regular, recurring schedule so nobody is wondering why they’re meeting with the boss. If you have something serious to discuss, consider making a separate appointment; it may even be required, depending on the issue. Status meetings aren’t the place to talk about HR infractions, job/title changes, or issues that involve other departments.

Have a plan and follow up

If you want an employee to feel undervalued, first make sure you have nothing to talk about, then forget what you two discussed in your last meeting. On the other hand, if you do want them to feel valued, do this: think about the meeting in advance, take notes, review your notes, and ask questions…so you can take even more notes. If you set goals, discuss problems, and see how things are progressing from meeting to meeting, you’ll have a better idea of how your employee is doing over time. And they’ll feel like you care, which we hope you do.

These are only a few of the many conversations you’re likely to have as a manager. Some of them will be easy, some will be hard; most will be necessary. Remember this: your first responsibility is to your people. Good managers know their team on a personal as well as a professional level, because that’s the best way to plan for success and avoid conflicts before they happen. And the only way to know people (well, the only non-creepy way) is to talk to them. So get talking.