Today's episode is for everyone who's ever had a hard conversation at work. Which is everyone.
When you know you need to have a hard conversation with someone—but your stomach is tense and your hands are sweating and you want to put it off for as long as you can… how do you find the courage—and the plan—to have a conversation that delivers a better outcome while preserving the relationship?
Modern Mentor is hosted by Rachel Cooke. A transcript is available at Simplecast.
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Hey, it’s Rachel Cooke, your Modern Mentor. And today’s episode is for anyone who’s ever had to have a hard conversation at work. Which is everyone. Because those conversations—the ones that make your head sweat and your stomach clench—they need to happen in order for us to get a better outcome. So how can we do it in a way that's empathetic, strategic, and sure to maintain your relationship? Here are my thoughts.
Last week I was catching up with my friend Sam. When I told him I had to go, he gave me the sad-eyes and the giant sigh of a guy not looking forward to something. I asked him what was up and he told me one of his colleagues had been dropping balls lately. Like, a lot of them. A missed client deliverable, a messy meeting not well-prepped for, an unpaid invoice resulting in late fees…the list went on.
“I’m not his boss,” Sam told me. “It doesn’t feel like my place to give him feedback. But something’s gotta give here.”
Whether a friend has disappointed you one too many times, your boss just won’t give you a straight answer about that promotion, your doctor’s advice leaves you feeling like she hasn’t heard a word you’ve said…you’ve been left feeling sad or scared or hurt or mad…we’ve all been in situations requiring us to have an icky conversation. They’re hard and awkward and we postpone them until we just can’t anymore.
So if you are—or have ever been—where Sam is, let’s talk about how to have one of these difficult conversations well.
Before you dive into the difficult, be clear about what you want. Because if all you want right now is to vent, then phone a friend, friend, and do not engage with the object of your angst.
A great question to ask yourself is—is this annoying or is this a problem? Your teammate who checks his phone one too many times during your presentation may be annoying. But your teammate who continuously cuts you off while you’re speaking is likely a problem.
We’re focused here on the problematic situations—the actions or behaviors that are infringing on your ability to be successful.
In Sam’s case, he was dealing with a problem. There were business impacts resulting from his colleague’s misses.
Having a positive difficult conversation begins with choosing the right conversation to have.
OK—with the right topic chosen (something you’re actually ready to solve), it’s time to open the conversation.
You could just cut to the chase and say “Hey, we need to talk about all the balls you’re dropping lately.” The upside here is there’s no ambiguity about what’s on your mind.
The downside—do you really need me to spell it out? Imagine being on the receiving end of an open like that. Your ears would smoke, your eyes would burn, your claws would come out. Problem-solving in that state is a pretty hard thing to do. And yes, I’ve tried this approach with my poor husband and can assure you—it doesn’t work out.
So what’s the alternative? You do want to be honest, but also kind and empathetic. Something more like “Hey, I was wondering if we could talk about a few projects that have gone pear-shaped lately. I’d love to share my experience of the past month, to hear yours, and to see what we can do to make sure all is on track.”
In this second approach, you’re still letting your colleague know something difficult is coming. But you’re inviting a dialog—not making an accusation—-and letting them know you’re hungry for ideas. This leaves room for real conversation and problem-solving.
Imagine Sam approaches his colleague saying “you’re not paying attention, you’ve stopped caring about your work, and you’re not thinking about the impact this is having on anyone around you.”
I mean, this should yield a positive response—right? Um, not so much. There are WAY too many assumptions in here that Sam’s making. Sam has no way of knowing what his colleague cares or thinks about.
OK, now let’s give Sam a redo. Imagine instead he says “I’m concerned about the feedback we got from the client on that late report. And Finance needs us to justify the late charges on that invoice—the cost comes out of our budget. Any insight on what happened?”
These are indisputable facts. Why those things happen—well, the colleague gets to weigh in there. But the fact that they happened seems hard to deny.
Facts give you something real to work with. Just make sure your intel is accurate.
You’ve laid out the truth and you’ve done so with kindness and compassion.
But maybe you’re feeling angry that you’ve had to pick up the slack. And maybe your colleague feels stung by the truth. It does, as they say, sometimes hurt.
Just be prepared for the possibility that having this conversation the right way doesn’t guarantee all rainbows and sunshine. It may still be painful.
If emotions escalate quickly, be ready to take a time out. And agree to come back once people have had a chance to collect themselves and regroup.
And please know that emotion is not a signal that you’ve done a bad job. It just means you and the other person are human.
Also, fear of emotion is not an excuse to avoid a difficult conversation.
You’ve made your case, you’ve invited their perspective and now it’s time to hear it openly. Maybe it’s true they don’t care about clients or the work anymore. Or maybe they’re dealing with a sick family member or haven’t received a critical training or have received conflicting requests from the client. Or—gasp—maybe you weren’t clear in setting an expectation or a timeline.
Your job here is to listen. And if you do it well, often a solution will present itself. Also, be prepared to take some accountability as well.
Maybe they need a leave of absence, or you need to sign them up for that training, or you both need to set better boundaries with the client.
Your goal here is to identify a possible step in the right direction.
Often the next step includes action on both of your parts. Having listened and listened well, suggest what might come next.
Maybe you’ll put your expectations in writing and they’ll send you weekly updates so you both know you’re on track.
Maybe you offer to take a priority off their plate. Or maybe they choose to take a leave.
There’s no right answer—only one you both agree will move you forward. Even just a tiny step.
Using this approach may not land you in a place of perfection. But likely it will do the job of opening a conversation, addressing some key issues, identifying a possible solution, and—critically—preserve your relationship.
Hope you’ll join me next week for another great episode. Until then, you can follow Modern Mentor on Apple Podcasts, Spotify, or wherever you listen to podcasts. Check out my website at leadabovenoise.com – or follow me on the Modern Mentor podcast page on LinkedIn. Thanks so much for listening and have a successful week.