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Leadership Fails & Flexible Work Wins: A Story You Need to Hear with Gillian Brookes - ep. 101

• GILLIAN BROOKES, RICK HANEY, KALEEM CLARKSON • Season 1 • Episode 102

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In the latest episode of our NSFRW series, Gillian Brookes—New Zealand’s leading flexible work specialist and author of Flexperts—joins us for a candid, laugh-out-loud conversation about workplace chaos, executive misfires, and the surprising power of honest dialogue.

From a “hot-mess” holiday leadership meeting to a high-stakes workshop that goes hilariously off-track, Gillian shares the story of an overworked leadership team and a brutally honest chief exec that led to some awkward moments and surprising lessons. Along the way, Gillian opens up about her mission to help organizations thrive with flexible work practices, how to navigate uncomfortable workplace dynamics, and why reframing challenges is the secret to successful leadership.

Packed with both humor and wisdom, this episode is a perfect blend of entertainment and insights. Grab a coffee and tune in for a story you won’t forget—and a few lessons you can actually use!

Learn more about Gillian:

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Got to hear a story That made you red in the face Had you drop right to your knees Only without a trace Dog screwin in the background Little baby man throwin cake Come on, y'all, don't go berserk It's all good here, hold it Word! Not safe for remote, word What you've got to say, not safe for remote work, eh, eh. Zoom in day to day, not safe for remote.

Rick:

Welcome to Remotely One's NSFRW Not Safe for Remote Work. Where we invite employees at all levels to share their most outrageous moments while working remotely. Do you have a story to tell? We want to hear it. You could submit your story at remotelyone. com forward slash podcast. Today's guest is originally from South London and is now a resident of Wellington, New Zealand. She is New Zealand's flexible work specialist. And is the author of the book, Flexperts. Gillian Brooks, come on down!

Kaleem:

Gillian place is going crazy. I want to

Rick:

Look at these people. Look at these people. You people are Hey, hey, down in front. Down in front. Settle down. Settle down. Okay? Let's keep this together. This is a professional atmosphere, people.

Gillian:

guys.

Rick:

Gilliann, thank you so much for joining us and for tolerating us this far.

Gillian:

Oh, it's a pleasure. Absolute pleasure. Yeah.

Rick:

No, it's, it's great to have you. We're, we're so excited to hear your story.

Kaleem:

she's in the future. I can't believe she's in the future.

Rick:

Yeah, this is insane. This is absolutely insane. Like I'm sitting here drinking a beer after a full day's work and she's just having her morning tea. I don't know how to feel

Gillian:

I know. I know. I'm in the weekend and you're still on Friday. It's insane.

Kaleem:

Oh my god.

Gillian:

blows our minds.

Kaleem:

So Gillian We are here for not safe for remote work where everyone's just telling stories um, tell us a little bit about yourself and what it is that you're doing these days and then Let's set us up for the story. I want to hear what's going. I can't wait to hear The story.

Gillian:

Okay. Right. So, what I do for a living is I'm a self employed flexible work specialist. And so I do lots of training. I work with lots of leaders and leadership teams to help them, get the best from flex, basically, you know, kind of help them understand how to get the best of it, how to have better flexible work practice, how to connect it to their workforce strategy, all these sorts of things. And I work with lots of different organizations across New Zealand to help them. Yeah. Kind of just dial up the benefits really. Cause a lot of them are kind of living with it at the moment and they haven't quite worked out how to make the most of it. So that's what I spend my time doing. Yeah. Yeah.

Kaleem:

the best part of the show, what's up with the story that you want to tell everybody, please let us know, you know, give us all the details where you were. How long ago was it?

Rick:

Take us there. Gillian

Gillian:

Okay. All right. So we're in New Zealand. We're in Wellington. We're in a public service department over here and there are many of them. And I was working with one particular leadership team from a public service agency. And it was just before Christmas. And over here at Christmas, it's hot. Everyone's tired. There's the,

Kaleem:

is craziness.

Rick:

Yeah.

Kaleem:

Why is it hot? Why is it hot there?

Gillian:

Because the seasons are upside down in the Southern hemisphere.

Kaleem:

well, no, they could be right side up for you though.

Gillian:

Exactly. Exactly. We're the right way up and everyone else is upside down.

Rick:

Yeah, but mind you, you know, when we're at the beach sipping on our hard seltzers, they're in like, uh, You know, zip up jackets and

Gillian:

Yeah. Yeah. Yeah. And it's, yeah, exactly. Crazy. Crazy. The world.

Kaleem:

Okay. Okay. So, so it's, so it's hot.

Gillian:

it's hot. And the lead up to Christmas in, you know, in New Zealand, but particularly in the public service is everyone's tired. Everyone has this crazy idea that everything has to be finished before Christmas. That's it. And they forget that when Christmas comes and we go back to work in the new year that there are more days to come. They forget that because everything has to be done by Christmas.

Kaleem:

Let's get it done today. There's

Gillian:

yeah. yeah. So everything's just like that needs to be done before Christmas Eve. Before we, we all have like strawberries and, you know, bubbles or whatever at Christmas Eve because it's summer. And so you have strawberries. So anyway, it's early December and everyone's tired. Everyone's hot and bothered. We're in this, we're in this room. I'm with the senior leadership team. There's about, I know, 12 people in there. So, And they're all just like, you know, big bags under their eyes and just like, what are we doing? Let's just, and, and what it is, right, is that they've decided that they want to kick off the new year with all this training for all their people leaders, which is great. So before we do it though, I want to spend some time with the senior leadership team to make sure they feel really good about what they're Good about what's going to come. They're really clear about the messaging they want to send out to their leaders. And so I run this workshop with the senior leadership teams, just kind of like, let's all gather together. I'll give you some context. What's going on with flex across the world, give you some data so that we're not overly swayed by those. Yeah, yeah, exactly. We're talking kind of facts and figures rather than like, Oh, well, I read this and I was talking to my mate and they said that, you know, like there's enough of that already. Right. So. bringing them together, having this conversation.

Kaleem:

Now, are you in person or you're remote?

Gillian:

so this is in person. We're kind of in person because they're trying to work out as an organization, how they can do more of this remote work, right? So it's, we're all in this hot room and it's, it's a little bit airless and not enough sunlight, sunlight, you know, it's just a bit stuffy. And We've been in this room for about at least an hour, at least. And we're going around the room and I've asked the question. Why is it that Flex matters to you as a senior leadership team? What is it that you want to see that's better than it, you know, the now once we've delivered all this training, like what's the real purpose for all this training? Why do you want to invest in this flexibility and doing it better? Right? Because there's so many answers to that question, right? It might be, we want to attract and retain talent. It might be, we want to have better diverse leadership teams. Yeah, exactly. We want kind of high levels of wellbeing, want to reduce the burnout risk for our people like. What is it that really matters to you as an, as a leadership team? And whenever I have that conversation, you go around and everyone's got their own version of that. And what I want them to get to is to all have the same, a bit of consensus or a bit of a common story so that when they're going out to their organization, they can be really all on the same page.

Kaleem:

Okay. I

Gillian:

So this is where the connection to strategy comes in, right? And we're going around and all the leaders, they're getting into it and they're kind of talking to each other. They go, Oh, that's really interesting. Yeah. How many thought of it like that? You know, how do we make sure this is like fair for everybody and everyone has more access to more choices. And I'm like, yeah, brilliant.

Kaleem:

mean, everyone's happy.

Gillian:

Everyone's like, well, they're engaged at least, you know, I wouldn't go as far as happy,

Kaleem:

No, I hear you. But I mean, you're, you're in the, as the facilitator to you, like you're pointing around and you're like, you know, you're doing your thing. You're loving

Gillian:

Yeah. Yeah. I'm loving it. I'm loving it. And then, and then I'm kind of writing up their different answers on the board so we can start to decide like which is the one that's kind of floating to the surface and is the one that's most important to them. And we get to the chief exec and, um, she sits back in a chair and she's at the head of the table. Right. And everyone kind of quietens down a bit. They're like, oh, oh dear. And she said, Gillian, can you stop asking me why this matters? Why I'm doing this? Can you just stop asking me that question? And I was like, oh God, oh God. And she said, um, I'm doing this because I have to, I wish I could stop talking about it. like, everyone's,

Rick:

do you do with that?

Gillian:

Shrinking. I'm the only person standing up in the room. Everyone else is sitting down. You can see them physically shrink. But I can't do that. I'm standing up. I'm at the whiteboard. Like writing down I'm like, Oh, no. And she's just like, I'm only doing this because I have to, do you know what? I wish I could stop talking about it. I just want us to move on. I just want us to stop kind of worrying about it. Like, let's just do the training and just move on. I was like, Oh, and I was like, okay. Um. There was a sort of ripple of discomfort through the team and people were kind of, you know, the shifty eyes when people are like looking at each other sideways and just like, do we do?

Rick:

What do we

Gillian:

now? There was a lot of that. And do you know what? Like, one of the beautiful things about being the external person. Is you don't have to save everybody, you know, like you could just, you can just let them be a bit uncomfortable and you're probably doing them a better service than trying to save everyone. Right. Cause you're like, herein lies your problem.

Kaleem:

So what happens? Wait, what happens? Like, so it's silent. Everyone's looking at it's like, damn, damn.

Gillian:

Yeah.

Rick:

Oh no, we've made teacher

Gillian:

And she So I said, well, the thing is, you could go out to your people and your leaders with that story. We're doing this because we have to but I don't think it's going to give you the shift that you're really looking for. You know, like maybe we could give that an upgrade. So why don't we like, have a little think about some of these other ideas on the board and see which ones of those you might want to.

Kaleem:

let's have a

Rick:

I mean, it really doesn't bode well for her leadership, for her to say, I'm only doing this because I have to.

Kaleem:

So what was, what was the final result of the policy of what ended up happening?

Gillian:

I think she was really uncomfortable. I think she was like, Oh shit. I've, Oh, sorry, I probably can't say that.

Kaleem:

No, No, no, this is an nc. Yeah, this is an NC 17 show. We throw, we throw

Gillian:

Brilliant. Okay.

Kaleem:

what? See what shit sticks. Yeah.

Rick:

Does she look at you and say, oh, that was a real cock up? No. No. That was a real cock up. I'm really in the piss now, aren't I? Ain't it? Heh heh heh heh heh.

Gillian:

she was all of a sudden really fascinated by her phone and then she, um, She suddenly had an emergency she needed to attend to, which I kind of thought was interesting because all of her senior leaders were already in the room that she was in. So I'm not quite sure, maybe it was, you know, something was going on with the ministers or something, you know,

Rick:

up her desk. That's what was going on.

Gillian:

so awkward.

Kaleem:

I'm curious about the end result of the policy. So you guys were talking about workplace flexibility and stuff like that. So what was kind of the end result? What they end

Gillian:

So, when she kind of left, she kind of left and left everybody else to kind of carry on. And I was like, okay, so where do you want to take this people? You know, do you want that story that we're doing this because we have to? Or do you want a better, do you want a different story? And they were kind of like, you know, it's obvious what the answer was. And so we kind of cobbled together something about making flexible work. Fairer for everybody and with everybody having more access to some choices, which was a an easy line Everyone you had to say it, you know It's not complicated and we went with that in the end, but honestly, I I've never had so many apologies from people in the room there was so not not from the senior leader hasten to add but from All of the rest of the leadership team, they were coming up to me, I was just going, I'm so sorry, I don't know. What's like, there's a lot going on right now. There's, you know, it's that lead up to Christmas time. Everyone's a bit stressed, like, I'm really sorry. That's not how she normally shows up. Like that's, that's just what we got.

Rick:

yeah, no, but that's, that says a lot about the respect that they had for you because they were put In an uncomfortable spot by one of their own and they didn't want you to think badly of them because she was mistreating you. So, I mean, that's good for you.

Gillian:

It was, it was. And do you know what? I think you're right. I think you're right. And do you know what I said to them? I said, do you know what? At least she was honest. Like, there are so many senior leaders who will be thinking that living by that belief that they've got in their heads, but they're not going to be brave enough to say it out loud. I said, at least she had the courage of that conviction to just be honest. Yes, it was uncomfortable, but at least we know what we're dealing with. If that's how she's feeling. We can operate with that in mind, you know? And so when I was then delivering the training out to all the people leaders, like there's about, I don't know, 120 people leaders that I then went on to train. I was able to kind of really Put voice to that feeling that some of them might have had, which is, Oh God, why are we doing this? You know, and I could just front foot it. And I could say, look, you might be feeling like, Oh, I'm doing this because I have to, you know, I'm doing this because it's, we've got no choice. My back's against the wall and here's how we can reframe it. You know? So it was kind of a bit of a blessing in the end, but God, it was uncomfortable.

Rick:

Oh, I would imagine so.

Kaleem:

love. Stop asking me. Just stop it. We're doing this because we have to.

Gillian:

this.

Kaleem:

Damn it, bitch. Why you keep asking me this question? It's like you brought me here to do this. Why are you yelling at me?

Gillian:

Yeah. Why are you yelling at

Kaleem:

Why are you

Gillian:

my

Kaleem:

at me? Yes

Rick:

I'm only showing up because the state tells me I have to

Kaleem:

right. I'm here cuz y'all paid me. Why are you mad at me? I don't get it such a weird dynamic and they're like you're the leaders Like I'm here to give you a softball. So, so great. Well, thank you so much for that story. Gillian, can you tell our listeners and viewers and our audience, where can they find you online? Where can they find you to, to, to

Gillian:

Yeah, of course. Thanks, Kaleem. Yeah. So you can find me@jillianbrooks.co nz, because I'm New Zealand based. That's where you can find me or you can find me on LinkedIn, Gillian Brooks and I'll pop up. And also, yeah, you can check out my book FlexBets, which you'll be able to grab online or, you know, an e copy. Yeah. So I hope you enjoy it. It's a very practical guide. It's not highfalutin or anything. It's just lots of practical tips about how to make the best of flexible work.

Kaleem:

Well, thank you so much. We really appreciate the story and I know our audience will like it too. Thank you so much. Yeah. Good stuff. Good stuff.

Rick:

it was really great to connect with you.

Kaleem:

Awesome. We'll talk to you later. Peace.

People on this episode

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Kaleem Clarkson

Co-host
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Rick Haney

Co-host