12 Tips for Handling Difficult Conversations at Work

When you were a kid, we're willing to bet you had a sure-fire solution for making monsters go away. Remember it? You hid under the covers. If you can’t see it, it can’t see you - it worked every time.

Unfortunately, this childhood catch-all fares poorly in the real (and much scarier) adult world. Your problems won’t disappear just because you’re not looking. In fact, they often get worse if you don’t pay attention to them.

If you’ve ever had a problem colleague at work and watched the manager purposefully overlook their behavior to avoid having to deal with a difficult conversation, you know all too well what we mean.

But what do you do when it’s you in the manager’s position? When you’re in charge of having the difficult conversation?

You can regress to hiding under the covers – or you can deal with the problem like an adult. Here’s how!

1. Reframe the conversation in your mind

If you think of the conversation as a difficult one, dreading it is unavoidable. Realise that the employee might actually be grateful for your discussion. Most people don’t purposely do badly in their jobs - they likely can’t see that they’re causing problems.

It’s your job as a good manager or HR person to act as a coach and mentor as well as a leader. Think of your meeting as a constructive conversation that helps both the company and the employee. By helping them see where they’re going wrong, you’re developing them as a person and allowing them to progress in their careers.

2. Understand your fears

There’s a good reason why most people don’t enjoy having difficult conversations. We’re worried that the other person will react badly – as well they might. No one likes having their mistakes and failings pointed out to them, especially in the workplace where their livelihood depends on being good at their job. They might be upset, indignant, or flat-out angry if they believe they’re being unfairly called out.

However, by preparing well – as you obviously are by reading this article - you’ve already drastically reduced the chances of things going wrong. Relax!

3. Choose an appropriate setting

Where you hold the meeting sets the tone for the conversation. If you have a private office, that’s usually the best place. If not, try to secure a meeting room, or a coffee shop for a more casual feel. Use your own judgement to determine what’s appropriate for the seriousness of the conversation and your company culture.

Wherever you choose, make sure it’s private and out of earshot of other colleagues. Embarrassing the employee won’t make for a productive meeting. No one that’s not directly involved or affected by the situation should know what’s happening.

4. Practice, practice, practice

Plan and practice what you’re going to say in advance so that you get the point across fairly without being condescending or accusatory. You don’t need a script, but preparing answers to possible questions or objections will keep you cool, calm and collected in the moment.

5. Listen to their side of the story

Make sure not to dismiss their point of view, particularly if the issue is regarding a complaint from another member of staff. Even if, for instance, you know that they can say nothing in their own defence, giving them the opportunity to talk and paying attention when they do will allow them to be less defensive. Not to mention, it will help create a dialogue of open communication and make things easier for everyone. 

6. Give them time and space

People aren’t their best selves when put on the spot. Give the person you’re talking to plenty of time to consider what you’re saying by speaking slowly and pausing regularly. That way, you end up with fewer indignant excuses and more reasonable, thought-out responses. 

7. Prepare real evidence

If possible, use only your own observations as a backup during a difficult conversation. This avoids any 'he said, she said, they said' nonsense and helps you get right to the points that need to be made.

The more real evidence you have of problematic behaviour, the easier it is to state your case clearly and the harder it is for the employee in question to accuse you of being unfair. 

8. Avoid emotional language

Don’t tell the person you're speaking to how you ‘feel’ or express personal disappointment – this makes it more about you than the issue you're discussing. It also adds unnecessary emotional drama to an already charged conversation.

Instead, remain as neutral as you can to create the best outcome for everyone involved. 

9. Bring a witness

If the offence is serious or if you’ll need to take disciplinary measures, bring along an impartial witness to verify that procedure was followed on all sides. This ensures the legitimacy of the conversation and the actions taken, subsequently avoiding any more potential issues down the line. 

10. Have policies in place

Make sure none of your company’s rules are unspoken to reduce you and your company’s liability. For example, it will be difficult to formally discipline an employee for late-coming when there’s no formal working hours policy.

Making sure your rules are set in stone and widely available so that you’re in the clear should the problem employee decide they are being unfairly singled out.

11. Create a plan for progress

When you have a difficult conversation at work, you need to be ready to discuss more than just the issue at hand. Not only should you be able to define exactly what the problem is, but you should also be able to explain how you’d like the employe to improve.

Depending on the issue at hand, you could put in place regular performance reviews, schedule catch-up meetings, or assign them a mentor.

12. Document the conflict

If you need to take further disciplinary action, it will be helpful to have a record of your conversation, including the next steps you’ve agreed on and the metrics for improvement you’ll be monitoring if necessary. If additional issues arise in the future, proper documentation can also help you come to, justify, and support the necessary resolutions.

 
Ultimately, dealing with the issue at hand will have better results in the long run than letting a bad situation fester. Your colleagues - even the troublesome ones – will respect you more for ditching the safety blanket and dealing with the situation head-on. 


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