Customer Support Leaders

From The Archives: 11: Awkward Conversations with Hilary Dudek

Charlotte Ward

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What if handling awkward workplace conversations could be less daunting and more compassionate? Join us as we sit down with Hilary Dudek from Gluco, who shares her expert strategies for navigating these challenging discussions with grace and empathy. With five years of tech support experience under her belt, Hilary emphasizes the importance of putting yourself in the other person's shoes and maintaining a balance between professionalism and warmth. She explains how intentional language and face-to-face communication, even via Zoom, can transform a difficult conversation into a constructive dialogue. 

Listen to Hilary's heartfelt recounts of empathy, from shedding sympathy tears to offering team members the space they need to process difficult news. She candidly discusses her own struggles with maintaining a poker face and the emotional complexities of delivering tough feedback. Learn practical advice on allowing employees to revisit conversations after some time, providing a thoughtful approach to difficult workplace interactions. This episode is a must-listen for anyone looking to master the art of compassionate communication in the workplace.

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Speaker 1:

Hello, welcome to the Customer Support Leaders podcast. I'm Charlotte Ward. Today we're listening to one of my favorite episodes from the archives. I'd like to welcome to the podcast today Hilary Dudek. Hilary, would you like to introduce yourself?

Speaker 2:

Thank you so much, charlotte. I'm a Michigan girl. I'm just living my best support life here. I've been in tech support for about five years now and I live with my husband and two wonderful children. I am currently with a company called Gluco. It's a diabetes management app.

Speaker 1:

The topic for this week is awkward conversations. I'd love to know if you have any particular gems of wisdom around how you conduct awkward conversations with your team, whether you've got strategies for coping with any fallout from awkward conversations, or indeed, if you've got any particularly excruciating stories to tell.

Speaker 2:

Yeah, no one likes awkward conversations, that is for sure. My number one strategy I think this applies to a lot of things, not just awkward conversations is coming at it from the other person's point of view and speaking to them the way you would want to be spoken to if you were on the receiving end of an awkward conversation. So what I try to keep in mind first and foremost, and then I also try to curve or filter the content or the words that I use by remembering this is business. This is impersonal To me. I'm a very warm person, so to me these conversations feel cold, but they're not cold as much as they're just very filtered to me If it's a performance issue for, know, we didn't see X, y and Z, so hence ABC, you know. Just let me know how I can help you. I'm here for you, but kind of capping it at that and not going into backstories or my boss thought this about you, but I said this and you don't need to know any of that.

Speaker 1:

Yeah, being quite intentional with your language and and kind of careful is what you're saying, but how does that affect your demeanor in those type of conversations? Are we talking poker face Hillary at this point, or or is there something else at play there?

Speaker 2:

I mean that's the goal, right, but I don't have a poker face at all, so it's usually a very serious face, but I think they probably can read it a little more than they should be able to. But I'm working on it. I'm working on it. My two-year-old son he's the master of poker face where I tell him something is just and he'll stay like that forever. So. But I mean, I always try to do these in a Zoom call, though I mean that if we can't, my team's entirely distributed, so if we can't be in person, that's an XX thing. You know, no one wants an email. You know, even a voice call if they can see your face, it's better.

Speaker 1:

That's really important, actually, isn't it? Because, distributed or not, I mean, even if you happen to be in an office, as you said, nobody wants that email. So, even if you're maintaining some personal and emotional distance from the subject matter, you actually still have the advantage of being able to deliver it personally, and face-to-face allows you to. Well, it makes it two-way for a start, right, it's not just you delivering something. How do you cope when the other person isn't so detached as you are? Because you've had the chance to prep as you go into these conversations, right? So if it's a surprise to the other party and I'm assuming we're generally talking, not a pleasant surprise how do you deal with the fallout on the other side of that conversation?

Speaker 2:

I will say I have found myself crying sympathy tears with somebody before just a little bit. I'm empathetic and it's just kind of happened so but I just let them know. You know this is coming as a surprise to you. I mean, what you just said, this is a surprise to you. Like I knew this was coming. You know, take the time we need to process. We can process right now in this call or because me personally I like to take it, go away for a couple hours and then come back and revisit it.

Speaker 2:

So I offer them that option as well. You know, if you need to go, process this and digest this and come back with your talking points, absolutely let's do that. I've had conversations like that where it was sort of a surprise. It hit me and then I got off the call and I hadn't asked like 1400 questions that I had just thought of, because I was too taken by surprise at first, and that was the first time this was at a previous company with the previous boss, and so he learned over time okay, this is a 10-minute meeting, I'm going to deliver what I need to say, I'm going to go away and then we'll reconvene in half a day or something he learned that over time, that pattern, it's really important to proactively offer that, I think, that opportunity to follow up.

Speaker 1:

I know as someone who's been on the receiving end of some of those awkward conversations as well. Not all managers do that, not all leaders do that. I think there's one thing I've learned is that if I am on the receiving end of those conversations and the leader doesn't offer that opportunities to just take the bull by the horns and ask for it, don't assume that because you're experiencing all of this, you know all of this shock, that that's the end of the story because you haven't been offered that in the meeting. It's kind of go away and be at one with those feelings for a while, but then follow up and ask to discuss.

Speaker 2:

Yeah, and I didn't realize at first that I could take the bull by the horns. That was pretty painful, but I figured it out. I wrote a strongly worded email. It was fun too. It was the co-founder of the company that I reported to and I wrote a very strong email and he was, thankfully, very kind. He's like. I see you have some feelings about this. Let's meet in a couple of days, okay.

Speaker 1:

So that's good, though right that he recognized it as a need and actually gave you an extra couple of days after your email.

Speaker 2:

I was like he wanted to talk to me. He's like, well, we'll just wait.

Speaker 1:

That's it for today. Go to customersupportleaderscom. Forward. Slash 11 for the show notes, and I'll see you next time.