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Manager Series, Part 4: Techniques for Managing Challenging Conversations

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Manager Series, Part 4: Techniques for Managing Challenging Conversations

This is Part 4 of a 7-part series on management best practices, tips and tricks, and what not to do.
Part 1 starts with the basics of being in management, and how to be a good manager.
Part 2 teaches you how to conduct a good employee performance evaluation.
Part 3 covers getting good job performance from your employees.
Part 5 helps you decide whether it’s time to fire someone.
Part 6 shows you how to fire someone properly.
Part 7 talks about how to tell the remaining members of your team that someone has been fired.


Okay, so you’re ready to have a workplace-appropriate (and hopefully effective) talk with an employee about one of their behaviors. You know where your flaming sword is, you’ve defined the outcome you want, and you’re prepared to ask them to repeat back what you’ve said.

Easy peasy … except that part where the employee responds. You have no idea how that part will go, but it’s a safe bet that they won’t react by turning cartwheels in appreciation. That’s why, in this installment, it’s time to play defense and look at some ways to move past initial reactions to make real progress.

But first, what NOT to do.

Here are some of the most common ways managers try to get employees to change their behavior, along with common outcomes:

#1.
The manager raises their voice, demands change, and ignores their employee’s response altogether. It sounds like this:

Boss: “CHAD! Next time you’re late delivering to that client, CALL THEM!!!”
Chad: “But …”
Boss: “No buts. DO IT.”

Managers think this works because Chad doesn’t talk back, his behavior possibly changes in the short term, and it’s a really fast and painless conversation. But here’s why it doesn’t: Chad feels resentful and unimportant, and he will often strike back. “Fine, you want me to call them? I’ll use my cell phone in the company truck while I’m driving. And when we get a bad review because I was caught talking on the phone, it’ll be your fault.”

#2.
The manager makes passive-aggressive suggestions, hoping the employees pick up on the hint. Here’s how it sounds:

Boss: “Hey, the client called and said you were late again. Do you know anything about that?”
Chad: “Oh yeah, I had to stop for gas and there was a big line …”
Boss: “Oh, well, we’re probably just going to lose the account, no big deal. I hope you got to listen to those podcasts you like so much.”

Managers use this tactic to avoid uncomfortable, direct confrontation. They think (read: hope) the employee will pick up on the behavior and change on their own. And, like the previous example, it’s pretty quick. It doesn’t work, however, because employees HATE it. They see it (and as a result, you) as childish, and the only likely behavior change is them rolling their eyes behind your back.

#3.
The manager says nothing. Instead, they just hope the employee notices their disappointment and changes their behavior. Sounds like this:

Chad: “Hey boss.”
Boss: “Hi.”
Chad: “Everything okay?”
Boss: “Yeah … it’s … fine … Chad.” (Cue disappointed face.)
Chad: “Okay, see ya.”

This one, too, is fast and non-confrontational, but the major flaw here is that most employees aren’t psychic mind readers. They might pick up on some negative energy or realize that the boss is mad, but beyond that they just find themselves stressed out over what it might be — or if it even had to do with them.

So, what does work?

The right way to have this type of conversation is going to take a lot longer than the super-fast-yet-completely-ineffective methods discussed above. But if you’ve been reading through the complete How to Manager series, you already have a few shortcuts in hand.

The most effective tactic in this particular situation is something that’s come to be known as verbal judo (or conversational judo, or emotional judo — they all refer to the same thing).

Judo is the art of using your opponent’s strength against them in a conflict. In its physical parallel, it’s like dodging out of the way when someone tries to punch you so they punch the brick wall behind you instead.

In workplace conflict, verbal judo plays off of 3 key concepts: Create an agreement to have the conversation, let them throw the first punch (at themselves), and start to rebuild once it’s all out in the open.

Step 1: Create an Agreement to Have the Conversation.
Believe it or not, one of the biggest sticking points in these types of conversations is whether they should even be occurring in the first place. Many conversations with employees can blow up with some version of “I don’t have time for this/I need to work on XYZ for major client ABC/I have to leave in 15 minutes for my daughter’s football game!”

To create the conversation, start with a literal and direct question:

“Is now a good time to talk about your behavior?”

If the employee says no, respond with:

“Okay, what day and time would be good for you to discuss your behavior?”

Once the agreement has been made, the employee is locked in. If they try to back out halfway through the conversation with a statement like, “Oh, I think I just heard my phone ring … gotta go!”, you have the agreement to fall back on.

“You agreed earlier that this was a good time for this conversation, right? Okay, let’s continue.”

Step 2. Let Them Punch Themselves Out 
Yes, it sounds harsh at first blush, but here’s the reality: Except for the least self-aware employee, they know what you want to talk about — and they have *prepared*. They have spent hours, if not days, talking to their friends, spouses, and colleagues to justify, contextualize, and ready their response to you.

To effectively perform verbal judo here, start with this simple question:

“Before we begin talking about this behavior, is there anything you think I should know?”

This question will unleash the floodgates. Be prepared for the answer to take 10 or 20 minutes of nonstop defensiveness, accusation, fear, loathing, prayer, and defiance.

Whenever your employee stops talking, simply say:

“Thank you for sharing all of that with me. Is there anything else?”

Rinse and repeat until they have gotten everything out.

Many managers get extremely frustrated by this process. It’s long and arduous, and you’ll likely want to interject and say, “That’s not true!” or argue with the person. It can also be a very long 20 minutes when you’re sitting silently while someone spews out defenses of themselves. So why bother? Because although it’s not an easy process, it is effective for changing someone’s behavior.

Step 3. Begin the Hard Work of Changing Behavior
This is the step that happens after the answer to “Is there anything else?” is finally “No.” For this step, you’ll need to specifically name the behavior and get their agreement on what happened.

“You agreed to complete a task by Friday, and on Friday the task was not completed. Do we agree on that?”

If the employee tries to revert back to Step 2 here and all the reasons they didn’t do it, it’s important to cut them off to move forward. Like this:

“I’m sorry, but I’m going to stop you there. We’ve already gone over the reasons, and I understand them, and now we’re only talking about the behavior. Do you agree that this behavior occurred?”

Once you achieve that agreement, you move to the final step.

Step 4. Tell Them How You Want Them to Behave in the Future.
This is another simple statement, but it must be clear.

“In the future, if you think you will miss a deadline, for any reason, I want you to let me know as soon as you’re aware it’s going to be missed. Does that make sense?”

Don’t settle for a yes or no answer here. Instead, ask the employee to repeat the request back to you in their own words. Here’s one way to ask for that:

“Just so I can be sure we’re on the same page, will you please explain back to me the behavior I want to see from you in this situation next time?”

Once you’re satisfied that they understand what needs to go down, the final step of the conversation is to ask if they will need any help implementing the new behavior. If yes, what?

“So that you can be successful at this in the future, is there anything you will need?”

Step 5. Write Everything Down.
Once the conversation is over, write down everything that happened and everything that was said. You don’t necessarily need to send it to the employee, but it’s important to record the agreement in case there’s a question in the future about what was agreed to.

Following all of these steps — as painful as the process might be — can successfully create a change in behavior. Since it can be a little complicated, here’s a longer, more complete version of this type of conversation to help guide you.

We’ll call it “Crap! That was due yesterday?”

The Cast

  • Boss: Heather
  • Employee: Josh

The Scene

  • Recently, Josh missed a deadline to deliver a report to his client, Moonstruck Chocolate Company, and the client is mad that the deadline came and went without any communication.

Heather: Hey Josh, it’s 3:30. Is now still a good time for us to meet and talk about your behavior around the delivery of the Moonstruck report?

Josh: Yeah, I guess.

Heather: Okay, great. Before we start, is there anything you think I should know about this situation?

Josh: Well, yeah, the timeline on this was insane. We were never going to be able to get it done that fast. Also, I had a stomachache on Friday, and like, it was really bad. Plus, Tony didn’t get me his segments of the report until, like, 4:30, and it was due at 5. And frankly, I don’t even like working with this client. They’re super rude.

Heather: Thank you for sharing this with me, it helps me understand your perspective. Is there anything else you think I should know?

Josh: Yeah, I mean, the deadline was never realistic, I don’t even know why we agreed to it. Also, I asked for 3 analysts and I only got 1.5, and the half was that new guy who kinda sucks, so he was really dragging me down with training instead of contributing anything. And do you even see how much training I do around here? Plus, you know we just bought a house, so I’ve been up all night assembling IKEA furniture, the cat hates the new house, and my wife wants to hire a “cat therapist,” which I didn’t even know is a thing. And frankly, I’m just feeling super burned out on all this stuff.

Heather: Oh wow, I didn’t know all of that. Thanks for telling me. Is there anything else you think I should know?

Josh: Ugh … no, I think that’s it.

Heather: Okay, thanks for letting me know. It really helps me understand how this went down from your perspective, and it sounds like you were under a lot of pressure to get this done! Now I’d like to move on to talking about your behavior. As I understand it, the report was due on Friday at 5, but you didn’t deliver the report, and you didn’t tell the client that we were going to miss the deadline. Is all that right?”

Josh: Yeah, but I asked for 3 analysts …

Heather: I totally understand, but we’ve already discussed that and now we’re focusing on your behavior. Is what I said correct? Regardless of the surrounding circumstances?

Josh: Yeah …

Heather: Okay, great. I understand there were reasons you missed your deadline, and right now what we’re talking about in this meeting is your behavior. In the future, if you’re going to miss a deadline for any reason, I want you to let me and the client know as soon as it’s clear to you that you won’t be able to make the deadline. Does that make sense?”

Josh: Got it.

Heather: Good. Just so I’m sure we’re on the same page, will you please repeat back to me what I want you to do if the same situation arises in the future?”

Josh: You want me to tell you and the client if I’m going to miss a deadline.

Heather: Yes. But let me be clear, I want you to let us know as soon as you know. If you know on Tuesday you can’t possibly make the deadline on Friday, don’t wait until Friday at 4:59 to tell us. Let us know on Tuesday, okay?

Josh: Yeah, okay.

Heather: Gosh, sometimes I think I sound like a 3rd-grade teacher! I promise, though, this method helps us both stay on the same page. So will you do me a favor and explain one more time in your own words what I want you to do in this situation next time?

Josh: Yeah. You want me to tell you and the client as soon as I know we’ll miss a deadline, and not to wait until the last minute.

Heather: Perfect, thank you for doing that. Is there anything you need from me to be successful in implementing this new behavior?

Josh: Yeah, I’m going to need an admin to keep track of my deadlines.

Heather: I’m sorry, but that’s not something I can offer you. I consider it a part of your job responsibilities to track your deadlines. Is there anything else?

Josh: Actually yeah, how about a big wall-sized calendar so I can write down my deadlines and not have them get lost in my email?

Heather: Absolutely. I’m happy to get one of those for you, thanks for asking. Is there anything else you need from me to be successful?

Josh: Not for this, but I do want to talk about resource allocation. I was set up to fail on this project.

Heather: That’s fair. We don’t have enough time to talk about that today, so let’s schedule another meeting to go over your concern.

And … scene.

The Bottom Line
Yes, having this type of conversation with an employee is a long process. Yes, it’s a slog. Yes, it’s way harder than the traditional ways of trying to get people to change their behavior. But the most important yes? It works.

Next up, “… but … some people need to be fired.”

Related content:
Manager Series, Part 1: What No One Ever Told You About Being a Manager
Manager Series, Part 2: How to Write an Employee Performance Review
Manager Series, Part 3: How to Get Your Employees to Give You What You Need
Manager Series, Part 5: Reasons to Fire an Employee
Manager Series, Part 6: How to Fire Someone
Manager Series, Part 7: Telling Your Team Someone Was Fired

Believe it or not, one of the biggest sticking points in these types of conversations is whether they should even be occurring in the first place.

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