304: Reverse One-to-Ones; with Greg Skirving

Your one-on-ones shouldn’t feel like a weekly status treadmill where we do all the talking and our team does all the nodding. Charlotte Ward sits down with Greg Skirving to unpack a deceptively simple leadership shift: the reverse one-on-one, where the direct report leads with their perspective instead of waiting for the manager’s agenda. 

Greg walks us through his practical structure a three-slide monthly check-in covering accomplishments, challenges, and what the person wants to improve next. We talk about why this works especially well in customer support and technical support environments that are drowning in metrics like tickets closed and MTTR, while so much real value goes uncounted: mentoring, onboarding, process fixes, cross-functional help, and customer moments that protect renewals. The goal isn’t more paperwork, it’s clearer thinking, better coaching, and a more honest view of impact. 

We also dig into the change management piece: why the first few rounds can be awkward, how to coach ICs who dislike “talking about themselves,” and how presenting internally becomes a safe way to build communication and confidence that carries into customer calls, incident leadership, and even career moves into pre-sales, implementation, or project roles. By the end, we connect the dots to a simple career advantage: building an ongoing evidence file that makes self-evaluations and promotion conversations easier because the proof is already collected. 

If you want one-on-ones that create growth and not just updates, listen now, then subscribe, share with a fellow support leader, and leave a review. What would you change about your one-on-ones first?

Transcript

Welcome And The Big Idea

Charlotte Ward 0:13

Hello and welcome to episode three hundred and four of the Customer Support Leaders Podcast. I'm Charlotte Ward. Today, welcome Greg Skirving to talk about reverse one-to-ones. Hi Greg, lovely to have you back on the podcast so soon. Um it's been a a good year when I get to talk to you a couple of times so early in the year. Um before before we're halfway, so I feel like, you know, I've peaked maybe. Uh nice to be nice to have you back. Welcome.

Greg Skirving 0:52

Thank you, and uh always love to be back. Thanks for having me.

Charlotte Ward 0:56

Yeah, I know. Uh now we were talking today about reverse uh one-to-one, one-on-ones, I think you said briefly at one point, which is like let's just clear that up for for um my sanity, if not for the sanity of our listeners. Um, one-to-one or one-on-one sync meetings, what do we call them?

Greg Skirving 1:17

So, well, yes, yes, yes. I don't think there's an incorrect answer, but I would say one-on-one. That's maybe North American, Canadian. I'm Canadian, of course. Um, so, but again, you know, I feel one-to-one.

Charlotte Ward 1:33

I'm gonna put this out there. I do hear Americans particularly and now Canadians say one-on-one, and it always sounds a little bit like a fight to me. But uh, I know that's not the the uh the intent of any of these meetings, right? But we're gonna use I might slip slip out with one-to-one, which is what I tend to call them, which you know, rightly or wrongly, that's my comfort place, that's your comfort place. We're talking about the same thing. Other people call them sync meetings, like weekly catch-ups, all of those things that you're doing broadly with your direct reports. Yes. Yeah,

What A Reverse One-on-One Is

Charlotte Ward 2:08

cool. All right, let's dive into it then. So um, I think most leaders would have a kind of well-established uh view that the one-on-one is where you meet with your direct report, you get status from them on everything they're working from, you might ask them to bring in any blockers or anything like that, and then like, okay, see you next week, right? But what what's reverse? How do we reverse that whole that whole thing? What do you really mean by that?

Greg Skirving 2:38

Yeah, so um I did actually, it's funny, just before I got out the uh before this podcast, I got out the abacus and the slide rule and realized that I've been involved in roughly 7,000 uh one one-on-one, one-to-one in my career, including myself with my my boss and then my direct reports. Um and a few years back, I keep saying that, but we lost two years with COVID. It was probably about 18 or 19. Um, um, I was in a a one on one, two-one with a made you conscious now, haven't I?

Charlotte Ward 3:19

I'm so sorry.

Greg Skirving 3:20

That's quite all right. And uh and and I realized, I realized that that your typical one-on-one is oh Charlotte, you're doing a really good job at this. Please keep that up. Um, I'd like you to improve in these areas. And then, you know, as you're sort of closing up your notebook or your laptop, you're saying, is there anything I can help with? Right. And it just became regular and mundane. And um I'm I'm very particular about making sure that my I have my one-on-ones with my people. Um others aren't, and I'm religious about it. Anyway, so I hearkened back to my time in support when we did QBRs. Um, but this is no different than a than a managerial and br and services or support. And uh and and and and I said, you know what? Let's let's take those three things, you know, what what what have you been successful at? Um what are you working on and and what challenges you have? And I and I said, you know what? I'm gonna I'm gonna I'm gonna reverse that. So so what I did is I created a program, you know, basically it was a it was a slide deck with three slides, and I said, you know, I want you to think about all of the great things that you did last month, um and and put them down. Um and uh and then there's another slide for challenges and then another slide for for what you want to work on and improve on the the next month. Um what what is uh and and at the time I worked at a metrics heavy um um company excuse me like we all do, MTTR and you know uh tickets closed and blah blah blah blah blah. And there's no there's no escalation report, there's no there's no reports on a lot of things. So I kind of wanted to change the focus. And what I really wanted was to hear from people. Instead of me saying you're doing a good job and I think you're doing well, and you might be challenged with this, and you might I wanted to hear from people. I wanted to hear what and of course everybody's a little different, so those so exact same topics, not changing anything, but the reverse part is is now my people come back to me and and we talk about the same things, but it's from their perspective. So that's that's kind of the premise after having done many of these and think this is so boring and mundane. What can I do to to liven it up? And uh so that's what I did.

Charlotte Ward 5:58

Okay, okay. And and how I I guess the first thing that I mean it makes a ton of sense. It really does. The the first thing that springs to mind is uh um that we get kind of stuck in a rut with our one-to-ones in in the format prior, you know, that you described um prior to putting your new uh your new reverse one-on-one in place. Um but also our direct reports kind of get stuck in those cycles as well. And so what I experience running some one-to-one sometimes is like they'll come expecting me to talk first. They might not like, you know, I try and give them space, try and encourage. But I think what's really interesting about this is that even if even if you give space and encourage and ask towards the end of the session, do you have anything else to cover? Have you got anything you need my help on? Those kind of questions. Um, because they're towards the end of the session, often, you know, we've covered most things, or um, you know, because I've been driving the initial part of the conversation and and maybe hopefully I'm already a relatively informed boss, um, you know, I've covered most of the items they wanted to cover anyway. So the the tail end of one-to-ones in my experience has often been, yeah, no, I think it's, I think we're good. Yeah, see you next week. Um Exactly. But uh but the direct reports, your individual contributors can be conditioned to that as well, can't they? So they can almost turn up expecting you to have the agenda and not necessarily prepping enough. Did was there, I guess my first question is, in a landscape where your direct reports presumably were conditioned in that way, in the way you'd previously been running one-to-ones, did it take them a while to kind of switch over? Were they, was there a transitionary period where you know this felt a bit weird to them and you had to kind of it's change, right? Bit of change management in the experience.

Getting Past The Awkward Start

Charlotte Ward 7:58

What was that like for them? How did that sort of uh you know manifest in the meetings?

Greg Skirving 8:05

Yeah, that's a great point. And and you know I'm big on perspective. So from the managerial perspective, it's like, my God, this is like nobody's even talking. I'm doing all the talking. But you're right, people need to go through uh a transitionary period. So the way I set it up is uh within the first week of each month, um, people will present. And I I really try and and and have people, I like I'll bring in different uh different members of the organization to provide exposure for different people. So it's it's it's a it's a it's a true, it's it's a it's a it's really an MBR. It's really an MBR. But um it's it's it's about them. But um yeah, absolutely. And what I do is when I onboard people, they they they start right away. What I tell people is is wherever you start, there's no good or bad. It's just where you are and how I can help you to to communicate um um and celebrate the successes that that you had last month. Where's we get so metrics driven, and there's so many things that people um um provide value to the organization working on little projects and and um helping hire, helping on board, mentorship. And there's no report for that. And and again, again, sort of sort of expanding and having people say, I'm proud of of what I accomplished last month, and and here are the mountains I climbed last month. We stop and we we we we celebrate that, you know, and then and then we talk about metaphorically, here are the mountains I'm gonna climb next month, here are the development things I'm gonna work on, here are my my KPR uh targets I'm trying to to achieve. Here are uh uh here's my contribution to you know non-core activities. And I really wanted to make it about them and and how they feel and and and uh um um there's a couple other things that I want to add to that, but I think I think that's what I do. But there's definitely a transitionary period because people, especially tech support people, they don't know how to present. One of the one of the I used to I used to get an objection all the time. My boss makes me do a PowerPoint every month, and I say, well, let's break this down. What is a presentation? So a presentation is collecting, capturing um uh salient, pertinent thoughts and communicating them in a contextual, valuable, uh persuasive manner, both written and orally. And I think cheese, cheese, don't you do that hundreds of times a day in your customer interactions?

Charlotte Ward 11:10

Right, yeah, yeah.

Greg Skirving 11:11

So can a consider it practice, but b, this is about you. Be be proud. Tell me what you did, tell me what you want to accomplish, tell me where you want to go in your career. So that was that was that was kind of the evolution from my side, but getting back to your original question. Yeah, it's it's not common. Um but uh once people get into it, it's you know, they love it. One more thing, I know everybody's asking, geez, Greg, this, you know, that's how how much time? It's an hour investment each month. Um when people get get good, they'll put their slides together. Well, they'll capture throughout the month with their slides forget. It takes about a half hour. And uh about a half hour to present. And it's for their benefit. It's not for me, and it's not me telling. I get to understand what people think and where they're coming from and what they what they consider success.

Charlotte Ward 12:04

And yeah, and and you know, to your point, like often tech support people who I work uh with most closely more than the wider um customer support, um, you know, so could can be so conditioned to be like heads down, solve the problem in front of you and move on. And you you get on that treadmill. And even though as a species generally we are quite introverted, um we're we're great at talking to customers, even at the very technical end. But but that introversion doesn't necessarily um, I mean, it it it uh I think makes people somewhat introspective, but that also means that they're not very good at talking about that introspection and what their actual ambitions and goals are, or or even what they might possibly be, you know, because when you are heads down talking about the problem in front of you every day, sometimes it's actually frankly just like quite hard to think beyond the the day-to-day and to to have, you know, those those uh you know bigger picture thoughts or or um you know hopes and dreams, right? They must be in there though. So this really forces the thinking and forces the conversation.

Greg Skirving 13:23

Yeah, exactly. And what one of the things that I like to do, one of the successes in my role is what I call graduating people to other roles and uh within the organization. Um, and that's a retention strategy for me, right? Um, having people stay within the company but move on to different roles. And um, and that means um um project management, that means uh post-sales implementation where you have to deal with customers, pre-sales. Um I've I've helped people become systems engineers, sales engineers on the pre-sale side where we're being able to collect thoughts, present them in an oral in a written manner that's persuasive and on point. Um, and uh, you know, just just the pure skill of being able to present alone helps people grow because they don't typically know how to do it. And they are um um um I've had people say, well, I don't like talking about myself. Well, yeah, just be objective. It's just the facts. Here's what I achieved. You know, I I uh in in my uh in my skills assessment uh last month, I realized that uh I'm weak in this area. So, you know, I want to take these courses uh to help uh help fill that gap and improve my uh ability to service customers and hence my

Skills Gained And Proof Collected

Greg Skirving 14:45

value to the organization. So it's it's it's a little bit of a a different uh different uh thought process.

Charlotte Ward 14:52

Yeah, yeah, yeah. That makes sense. That makes sense. What um what is this? Uh what benefits have you seen this bring over time? You've been doing this for some years now. What what what was the arc that these uh individual contributors went on in the the first few months of doing this and now presumably years down the line?

Greg Skirving 15:13

Yeah, yes, it's really funny as uh you talked about people adjusting and how they change. Um, I've adjusted. I'm a tinkerer, I'm a recovering perfectionist, and I'll still tinker with this process. Um but uh just a funny story. The first ones I ever did, I have three slides, you know, accomplishments in in April, challenges, and what I'm gonna work on in uh in uh uh in May or whatever. And uh and people would show up with blank slides, and I'm like, did you I mean you don't think you did anything? And then I'm like, okay, okay, I'll adjust. And then I went ex example. You know, uh this or did this, and then people would show up, they just took the EXs off. I'm like, okay, I gotta find a way to get people to think about this. So I I've changed. But here are the benefits to this program. Um, you you you get to hear from people um and what they think, right? Because you know, not that you're forcing them to talk, but when you talk, they just nod and say yes and blah blah blah. Right? I want to hear, I truly want to hear, I really value my relationships with my people, and I truly care and I want to know. So now they're kind of forced to do it. And eventually they they open up and they become more comfortable and better at it. Number two, presentation skills, which is a direct uh uh uh tie-in with communicating with customers a day.

Charlotte Ward 16:43

Yeah, yeah, yeah.

Greg Skirving 16:44

Goodness. Um another little uh another little throw-in. Um we all do self-evaluations at the end of the year. We've got 12 beautiful receptacles, which we which they can cut cut and paste from. Um you touched on something about how people think, and and what I want to do is is make sure that people look beyond that myopic, I've got a ticket, what's the next step? Here's your solution, can I close the ticket? It's like you bring so much more value to the organization um that you don't even think about. Uh one of the things that I do is I say, um, we do six ads, so you get the formal stuff, but I'm saying you get recognition all the time, but your radar's not on. Right. And so what I do is I have people go through an evolutionary process. If on a ticket somebody said, Hey, Charlotte, thanks for taking the extra time to help me with that, I'll be able to, you know, cut like people have some of my folks will show up with three pages of recognition literally from customers.

Charlotte Ward 17:50

I I completely agree. There's nothing in that, I mean, I call it like an evidence file, you know, it's just a a little drop box, a little Notion page, a little Google Doc, whatever it is, just something that you can dump screenshots and text into with uh, you know, half a line context if you can, if it's not clear, so that exactly when you have these opportunities, whether they come once a month or your annual review, um, you know, or you're making a case um for yourself, like at promotion time, whatever it is, it's crucial that you keep that paper trail, isn't it? And and one-to-ones are to your point, however they're conducted, are an opportunity to um build that further. But yeah, what a great way to have like 12 clear kind of inputs, fixed inputs before the year ends.

Greg Skirving 18:41

I forgot what I had for breakfast. You you you want me to do uh a self-evaluation of what I did 11 months ago. I hadn't a clue, right? So yeah. Um yeah, it's it's good for that. And and like I said, there's been some direct help with people that have gone, especially into pre-sales, but even post sales, you know, I I I like to say that there are, you know, everybody get everybody on post-sales, if I got sales, I'll never do sales. And until you've done it, you don't really understand it. Maybe that's a problem for another day. But but there's a lot people can do with the two key uh skill sets that we have in in support, and that's technical skills and customer fixing skills. And and you can do that post-sales, you can do that implementation, you can do that pre-sales. So when you look at it like that, it's a different perspective. This helps with that.

Charlotte Ward 19:32

Um and I really, I really love the parallel you drew before as well. Like these communications that we are really good at in support, communicating with customers, you know, translating things for the audience, um, phrasing things in a politic way, or, you know, or a or a you know, a helpful way, um, or or you know, like helping the customer themselves go the extra mile, never mind you going the extra mile for them. Um all of those skills and and actually, you know, carrying an incident, carrying a hot customer call, all of those things, the things that support teams have to do all the time. Um everything you're talking about here just builds those skills further. So it's actually, I think, quite symbiotic. Like having good customer communication habits and skills will manifest when you begin to give people the opportunity to talk to the business. But also, also the reverse is true. You know, if you're if you have like less confident staff who and we've all had them, we have one or two ICs who like try and avoid getting on Zoom with the customer, they'll just send one more reply, even though they are skilled enough to be able to get that customer to a solution. Sometimes a call goes a long way, but you know, for whatever reason, there's a lack of confidence

Beyond Tickets Toward Business Impact

Charlotte Ward 20:55

there because it's the getting in front of people and talking in an environment where things might be a little unpredictable because it's people. Um you can carry those skills out of the business context, your one-to-ones, particularly if you're putting them in front of other other folks. Um they're all people, but it's a safer space, and those skills build to carry over more confidence in customer conversations as well.

Greg Skirving 21:20

Yeah. And one more thing that I forgot to mention, um, it changes the scope of the value of the contribution. It's not just tickets. Again, when I came up with this this concept, it was metrics heavy. And it's like, Charlotte, you're a top third performer. It's like you're a bottom third performer, you better shape up, right?

Charlotte Ward 21:38

That sounds more accurate, to be honest.

Greg Skirving 21:42

I'm in that, I'm in that category, not an exclusive club. But but but having people understand that you close three tickets a day, what does that mean? Well, wait a second. That's the transactional. part that builds into the relational part of the of the the the customer's perspective of dealing with us as an organization. So I'll have even people come in and say, you know, worked with a uh an an S E to help them do a demo and we landed a sale or you know worked with this customer and they recently renewed their support contract. So I get people thinking about just numbers and 18 tickets and blah blah blah to no no you help shape the customer's perspective of why they want to continue to deal with us why they want to be um why they want to buy more product or service why they want to so important.

Charlotte Ward 22:46

Yeah why they want to stay customers right so important. And uh um I I think this is exactly what we were talking about is like looking beyond the ticket. You know if you if you as a support engineer only look or as you know customer support agent whatever are only looking at the next ticket in front of you and not connecting it to the bigger picture then the that is the entirety of the value that you think you add. And actually um forcing that thinking like getting people to answer why why why is that important? Why the fact why is it an achievement that you solved three tickets today you know and why is kind of a difficult one for people to answer sometimes a slightly harsher forcing phrase I sometimes use is so what? So what you know like why should I care? Like obviously I care I'm your leader and like this is our core function but but like what if somebody else in the business so what? So what Charlotte sold three tickets today. So what is that good or bad? I don't know I don't know you know but connecting it to other outcomes particularly retention you know customer success um renewal sales all of those things it sometimes takes a couple of leaps to your point while I worked with the sales engineer and the sales engineer then did this and then the customer that like you you are as a support person aware enough of what customers um needs and and aims and goals with the platform are so it shouldn't be so long as you just switch that view a little bit it shouldn't be too hard to make similar leaps organizationally I think yeah I I go with uh I go with uh three C's capture did you capture all the important things and oftentimes I'm saying didn't you do that?

Greg Skirving 24:42

Didn't you handle that S Oh yeah oh yeah um how you construct your bullets and typically I get you know uh had a call with customer and solve ticket it's like well what does that really mean where so what right so it was funny so well that's what I get up to so what right you know you they they were down you brought them up and then how you speak so anyway it's kind of a uh uh uh I'm I I haven't invented the the concept it's just a little tweak you know it's that we're we talk about the same things it's nothing different it's just that it comes from the customer side I mean if uh I and I would say I would say if anybody wants to know how to do it you know contact me if you want but it's pretty basic together and you've got you know accomplishments from last month you know challenges that I need your help with and here are my goals for this month. It's pretty basic and yeah cat can kind of funny something that we've done thousands of times in our lives and yeah and never really examined yeah one rainy day I went I'm sick of this yeah yeah I changed it up and it's been successful for me so yeah that's awesome thank you so much for sharing that with us today Greg.

Charlotte Ward 26:00

Um I'm gonna go away and have a a constructive rethink of my own one-to-ones or one-on-ones

Final Takeaways And Next Steps

Charlotte Ward 26:05

and uh yeah it's uh it it's it's super fascinating to think about how we can actually change those conversations we don't need to like cookie cutter them. So yeah thank you so much. Well thank you that's it for today go to customersupportleaders dot com forward slash three zero four for the show notes and I'll see you next time.