Got a Difficult Conversation Coming Up? Consider These Three Factors

Do you have a tough conversation coming up with a team member, co-worker or your boss?

Maybe you have to have deliver one of those year-end performance conversations that begins with, "You're not meeting my expectations."

Or, you're feeling like you should be earning substantially more money and you're ready to ask your boss for a raise.

A lot of forethought needs to happen before you conduct a difficult conversation with a subordinate, peer, or your boss. Here are three factors to consider when planning such a meeting.

Factor Number One: Your Relationship to the Other Party

How you approach and conduct a conversation with someone is entirely dependent on the relationship you have or don’t have with the person you’re speaking with. It would stand to reason that the way you would approach someone you’ve known for years would be very different than someone you met for the first time last week.

Say you’ve worked with someone in a previous job. Experience tells you that this person doesn’t react well to surprises.

Before having “the big talk,” you know that you better have spoken about the topic at hand (more than once), or this individual will not react kindly.

Now suppose the employee you need to speak with is someone you met for the first time last week. In this case, you’d want to broach the topic that’s weighing on your mind carefully.

It would help if you thought through what you might do if the conversation doesn’t go as well as you hope, and how you might respond should things go better than expected.

Factor Number Two: Timing

Have you ever noticed how some people have impeccable timing while others seem to be oblivious as to what’s going on around them? I have.

Take the example of an employee asking for a raise ten minutes after the company announces a significant drop in earnings. Or the boss that comes into your office on a Friday at 5:00 p.m., sees you packing up for the weekend, and begins a discussion that you know will go well into the evening hours.

There’s a time and place for everything, including the handling of challenging conversations.

We’ll get to place in a moment. When deciding the best time to take on a situation, think less about yourself and more about the person you’ll be addressing.

Let’s say you’re disappointed with how your boss handled a particular matter. You’ve made the decision that you are going to speak up and express your dismay. You check your manager’s schedule and see he will be in back-to-back meetings until 2:00 p.m. Anxious to get the conversation over with, you grab the 2:00 p.m. time slot.

I can pretty much predict how this conversation is going to go based on your timing.

Your boss will be distracted as he thinks about how he’s going to get to all the calls and emails that are now waiting for him. He may even be feeling a bit exhausted, having just attended a string of endless meetings.

This is not the time to say what’s on your mind.

Do yourself a favor. Look for an appointment time when your manager’s schedule is less frantic. You’ll be glad you did.

When it comes to timing, we tend to underestimate how much time is needed to address delicate matters. Take those dreaded “I have to let you go” conversations.

You go in thinking that you’ll deliver the news, the person will take a few moments to absorb what you’ve just said, maybe they’ll ask a few questions, and they’ll be out the door in no time. Thirty minutes should be fine, right?

That’s not how these discussions typically go.

You may have had time to prepare yourself for what is, no doubt, one of the most challenging conversations any manager may have. However, the person on the receiving end of this news has just had his or her life turned completely upside down. They may very well need more than the thirty minutes you’ve allocated on your calendar.

In situations like this one, you’re best off booking more time than you think you’ll need. I’m sure you’ll have no problem finding something to do should you find yourself suddenly with a few spare minutes.

Factor Number Three: Location

Where you hold a meeting matters as much as what you plan on saying. I write about this in detail in my new book, Can We Talk.

I’ve walked by conference rooms where it was obvious to me (and everyone else) that one of “those” types of conversations were taking place. I felt badly for the person sobbing in their chair and embarrassed for the other party, who didn’t have enough sense to at least draw the blinds.

Finding private space these days isn’t easy. The popular open office concept has resulted in droves of employees walking up and down the corridors looking for a quiet place to convene. It’s no wonder why Starbucks seems to have become an extension of some people’s offices.

Just because there’s space to have a challenging work meeting at a coffee shop, doesn’t mean you should. Too many opportunities for people around you to hear the conversation.

The coronavirus pandemic has changed forever the way we work. Before the pandemic, it was considered bad form to terminate an employee or ask your boss for a raise from afar. Now it’s deemed to be acceptable to have these life-changing conversations over Zoom or by phone.

There’s no telling what the “new normal” will look like. However, one thing’s for sure. Virtual workplace conversations will not be going away anytime soon, which will add more complexity to what used to be a simple decision in terms of location—“My office or yours?”

Of course, circumstances outside of your control may dictate where you’re to meet. If possible, face-to-face meetings in the same location are preferable for those heart-to-heart work conversations.

Difficult work conversations are here to stay, so you might as well get good at handling them.

Could your management team benefit from working with a coach to help?improve the way difficult work conversations are being handled? If so, schedule a call with me.?

?Best,

Roberta