11: Awkward Conversations with Hilary Dudek

Charlotte Ward 0:14
Hello, and welcome to Episode 11 of the Customer Support Leaders podcast. I’m Charlotte Ward. Our theme for this week is Awkward Conversations. So stay tuned for five leaders talking about that very topic. I’d like to welcome to the podcast today, Hilary Dudek. Hilary, would you like to introduce yourself?

Hilary Dudek 0:39
Thank you so much, Charlotte. I’m a Michigan girl and 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 Glooko. It’s a diabetes management app.

Charlotte Ward 0:57
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.

So 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 isn’t personal. 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. I don’t know if it’s a performance issue, for example, you 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 often, you don’t know.

Yeah, being quite intentional with your language and, and kind of careful, is what you’re saying. But how does that affect your demeanour in those type of conversations? Are we talking Pokerface Hilary at this point or, or is this something else?

Hilary Dudek 2:40
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 and 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 has…. He’s the best at pokerface where I tell him something, it’s just 😐 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 a person, that’s next best thing, you know, no one wants an email, you know, even a voice call if they can see your face. That’s better.

Charlotte Ward 3:17
That’s really important, actually, isn’t it? Because distributed or not, I mean, that even if you happen to be in an office, no, 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’s 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?

Hilary Dudek 4:05
Um, I will say I have found myself crying sympathy tears with somebody before. Umm, just a little bit. I’m pathetic, and it’s just kind of happened. So, but I just let them know, you know, this was 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 you 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. 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 Oh, because I was too taken by surprise at first. And that was the first time this was with a previous company. He was a previous boss. And so he learned over time, okay, like, this is a 10-minute meeting, I’m gonna deliver what I need to say, I’m going to go away and then we’ll reconvene and you know, half a day or something, he kind of learned that over time, that pattern.

Charlotte Ward 5:13
It’s really important to proactively offer that I think – that opportunity to follow up. 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 opportunity, is 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. Yeah,

Hilary Dudek 5:54
And I didn’t realise 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 funny too. It was the co-founder of the company that I reported to and very strong email and he was thankfully very kind. He’s like, I see you have some feelings about this, like, Let’s meet in a couple days.

Charlotte Ward 6:17
Okay. So that’s good though, right that he recognised it as a need and, and actually gave you an extra couple of days after your email.

Hilary Dudek 6:27
I was like you wanted to talk to me. He’s like, well, we’ll just wait.

Charlotte Ward 6:36
That’s it for today. Go to customersupportleaders.com/11 for the show notes, and I’ll see you next time.