How to Prepare for a Difficult Conversation

If you’ve held a managerial role for any length of time, then you’ve probably experienced already the need to counsel one or more employees. Maybe the issue has been substandard performance, or there’s been a bit of misunderstanding that has gotten out of hand. Or perhaps there’s inappropriate behaviour – unwanted attention or vulgar language. Even immodest dress and lack of personal hygiene can become issues.

At some point you will have realised that you need to talk with that individual, because having failed to do so thus far, the other employees have started to get nervous. Rumour has it that one or two have begun to polish their CVs.

The Internet, not to mention books and magazines, is filled with advice on how to prepare and then conduct your meeting: Get your facts together, gather the evidence, and schedule a meeting or include it in your discussions at appraisal time (what a terrible idea that is). And when it’s time to sit down with that employee, you’ll be ready with your little agenda. You’ll know what to say and the order in which you should say it. Your planning will be so perfect that when it comes time to put it into practice you’ll sound just like a dispassionate parrot. Then you’ll tick the box that asks if you’ve followed all the steps in your little agenda, file your notes, and put a follow-up date in your diary. For most managers, that’s what a successful counselling session looks like.

Few people set out to disrupt the workplace. In fact, most begin each job with a certain enthusiasm – an expectation that they will enjoy the work, make new friends, and generally get on. And so when a problem does occur, it can be something of a surprise – for everyone.

It’s not unusual for the person who caused the ruckus to have intended to be helpful or to show some initiative. It is rarely to offend. He or she could still feel that it was the right thing to do and on that basis refuse to apologise. But whatever was done or said has now upset the proverbial apple cart, and it’s up to you to sort it out.

How should you handle it? By following the textbook counselling strategy described above, or by using another method?

“Gotta a minute? What do you think about . . . [the topic at hand described in the third person singular or plural]?”

Notice the informality.

You don’t ask this question by sticking your head out of your office door or by acting in a way that should give the other person any cause for concern.

Or you could say, “I heard that – “ and then in a few words explain what happened, leaving out any names if possible.

“I heard that there was a disagreement in the office; something about [the topic] . . .”

Then let the other person tell you what happened. Don’t pass judgement. Ask if there’s anything you can do. And when you do this, make sure that you are sincere. In other words, express concern because you are, not because you’re acting.

What usually happens? You leave a message in someone’s pigeon hole that says, “See me” or “Come to my office”. For the person involved, it could feel very much like “Wait ‘til your father gets home”!

What do you suppose goes through the mind of that person? What emotions do you think he or she is experiencing when someone picks up a message like that and then goes to your office, only to find that you’ve gone home for the weekend, or on a trip, or into a meeting lasting for most of the day?

One author has suggested a “direct” approach: “Joe, I want to talk to you about why something happened that you were responsible for and Mary asked about in the meeting. Let’s make it first thing tomorrow morning”.


That person could be scared all night, sick by the next day, or unproductive until you finally do meet.

You have to get back to the original question. What’s the goal? For what reason do you need to talk to this person?

If it’s only to solve the problem so that everyone can get back to business as usual, then you’re scuppered before you even start. That’s because things won’t get back to the way they were. They’ll either be better or worse; but they’ll never be the same. People change.

There can be hurt and then healing, or hurt and then more hurt. It’s your choice.

The most effective way to solve a problem, any problem, is to keep things as informal as possible for as long as you can. As soon as it feels formal, the game changes. The worry comes in. The productivity vanishes. Fear escalates. Insecurity takes hold. Defence barriers are raised.

If you want healing to come from this, then the goal must be to restore the relationship between the persons involved – the one at the centre of all this, his or her colleagues and you. When co-workers genuinely “make-up” – forgive one another – the humility that comes with it strengthens the relationships; and when that happens, the rest takes care of itself.

So how do you prepare for a difficult conversation? By dealing with it before it becomes difficult.

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