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Charlotte Ward •

287: Extreme Delegation: How To Lead When Everything Changes At 4 PM On An Idle Tuesday; with Matt Dale

About this episode

A quiet Tuesday turns into a leadership stress test. We share the playbook for extreme delegation—those moments when a key lieutenant leaves, the CEO secondments you into a new role, or a surprise launch forces you to hand off mission-critical work fast without dropping standards. Matt Dale joins Charlotte Ward to unpack how to keep people safe, outcomes clear, and momentum steady when the plan changes mid-flight.

We start with the groundwork that makes speed possible: knowing your people, tools, and data; modeling calm, context-rich communication; and showing your work so others can replicate decisions. From there, we move into the safety contract that empowers new owners—explicit boundaries, time-boxed expectations, clear escalation paths, and a promise of advocacy when scope creeps or politics intrude. It’s still your accountability, and staying close with tight check-ins preserves agency while preventing drift.

Then we tackle ruthless prioritization. You can’t hand over your entire mental map and hope for the same outcome. Strip to essentials: customer promises that won’t bend, survival metrics, and the smallest system that delivers them. Pause nice-to-haves, and make smart, short-term investments—like an AI co-pilot or tighter knowledge flows—that shrink ramp time and amplify output. Real stories bring it to life: navigating a six-month secondment during acquisitions, replacing a leader mid-crunch, and accelerating an AI rollout to support hiring and scale.

This conversation is for support and CX leaders who have earned the reputation for getting it done and want a cleaner, calmer way to do it when chaos hits. You’ll leave with scripts, structures, and mindset shifts that turn a blindsiding week into a clear plan with confident owners. If this helped, follow the show, share it with a teammate who’s under pressure, and leave a review with your best extreme delegation tip.

Matt Dale

Transcript

Charlotte Ward: 0:13

Hello and welcome to episode two hundred and eighty-seven of the Customer Support Leaders Podcast. I’m Charlotte Ward. Today, welcome Matt Dale to talk about extreme delegation. Today, welcoming back after quite some time. Matt, it’s been or it’s been a minute, I think, as you Americans would say. I I’m not sure what I would say. It’s been a damn long time. It’s lovely to have you back.

Matt Dale: 0:44

Would you um lovely to be back? I love what you’ve done with the place, a new coat of paint. It feels like a whole new studio over in here.

Charlotte Ward: 0:50

It practically is a whole new studio. Uh yeah, it’s lovely to see you again after such a long time. Um for the uh for the benefit of people who are joining us anew in 2026, would you do a quick intro?

Matt Dale: 1:03

Sure, yeah. So I’m um Matt Dale. I run a small consultancy called Moxie CX LLC, and we help companies that are um like many of them out there need help with their CX, whether that’s helping people level up, finding the right tools, um, looking through processes and making them better, uh, basically doing all the fun things that companies need if they want to have a good CS or CX uh solution. I also work at a couple different uh companies uh as a consultant. Um, and so I’ve been, you know, in customer service, customer experience pretty much my whole life. Um and I love it. It’s good, it’s a good place to be. So I’m happy to be here with you today and talking about some fun stuff.

Charlotte Ward: 1:38

Yeah, yeah. Thank you so much for that re-intro. Um I like you, I’ve I’ve spent a lifetime in every every uh meaning of the word, a lifetime.

Matt Dale: 1:48

But sometimes just the last couple of weeks feel like a month, a lifetime, right? It’s not just uh, you know.

Charlotte Ward: 1:53

You need this is how I know we are kindred spirits because I said that and you immediately felt it. Yes, I’ve lived a lifetime today. I lived a lifetime last week, and uh it has actually been a lifetime as well. So uh I always love a good success story about a career in CX, a career in support, um, because I think there are a lot of people out there who don’t believe you can make a career out of this, right?

Matt Dale: 2:20

Yeah, and I I don’t know that I I know your story a little bit. I don’t know that either of us really set out trying to make a career out of it. It just sort of happened. One of these days I’ll figure out what I want to do when I’m an adult and grown up, and um, then I’ll go do that thing, but it hasn’t happened yet, and this is a great place to be until then.

Charlotte Ward: 2:35

It is. I you might have spotted that the listeners might have spot. I pulled a bit of a face when you said, I don’t know that we intended that we intended to be.

Matt Dale: 2:43

Maybe you were much more intentional than I was. You know, I mine was just kind of stumbling around.

Charlotte Ward: 2:47

Yeah, would it be really annoying if I was?

Matt Dale: 2:49

I mean, you know, if that’s where you’re at, I think that’s totally good too, you know. And and again, thinking about our audience, um those out there that have been dreaming of being that person, running those customer service, customer support, customer experience teams, um, you have a role model in Charlotte. You can look up to her, learn from her example, from a little girl. She was like, This is what I want to do. And she’s gone through her whole career in that direction. I I I took a long and winding path to get here. Um, and I’m not sure that I’m where I need to be, but I’m enjoying the process. So, you know.

Charlotte Ward: 3:20

I mean, it’s a continuum, isn’t it? So I didn’t mean to cackle quite so much at the thought of being a role model, but it’s very funny to me. Um, yeah, I mean, maybe not when I was a little girl, because when I was very small, I wanted to be a vet, which I suppose is just a different type of support. It’s it’s it really is.

Matt Dale: 3:36

You know, it’s healing, it’s taking care of people or things.

Charlotte Ward: 3:39

Things, yeah, things for people, actually. Same book.

Matt Dale: 3:43

And they can be emotional support animals now, so that’s actually a support adjacent, right?

Charlotte Ward: 3:47

It is, it is like things for people, different technology, that’s all I’m saying.

Matt Dale: 3:52

Like what meat meatware, is that what it’s called?

Charlotte Ward: 3:59

Oh god, that sounds awful. Yeah, it does, yes.

Matt Dale: 4:02

Dystopian or other, you know, cyberpunk or something, but nothing.

Charlotte Ward: 4:06

Let’s let’s stop this bit of the conversation, but but the danger of having me back on the show, Charlotte. Oh, it’s so true. It’s so true. I’m already regretting it. Um, I uh I um but I was I was sort of more intentional. I knew by the time I was at uni that this was sort of I was doing a computer science degree, and that was in in back in the day. That was quite engineering heavy. Um I knew but weirdly I didn’t want to be an engineer.

Matt Dale: 4:40

So I I actually I think we talked and I had a similar experience. I was doing um computer science at the in during my high school uh 12th grade year at community college, and and I was either gonna go full-on computer science, and I was accepted to start several schools for that, and the other option was doing classics, grade books. And I ended up going to classics grade books because I didn’t want to debug. Like I love writing code, but I don’t like finding the missing 70 colons, 15 lines up, where the compiler fails and and you just want to tear your hair out. And I was like, you know, the the robe diverged in a in the yellow wood, and I took the classics route rather than the program things and make a lot of money. Sure, yes, that’s the one. That’s I knew there was a quote from somewhere. Yeah, yeah.

Charlotte Ward: 5:20

Yeah, yeah, yeah. Well, you know, I’m I’m here if you want any classical English education, Matt. There you go. From the mother country or something. That’s right. And I’ll say, Yeah, sorry. Sorry, I should stop that. Um, but um, yeah, I I think like you, so I I I had that similar experience and I’ve written about it. Like I grew up with computers in the era maybe you did, you’re a little younger than I am, but maybe those this was still a thing, where programs were listed in the back for you to type in. Do you remember that? You did yeah, nodding into you.

Matt Dale: 5:55

And that was when I was we had an Apple IIe when I was little, you know. I went that route. So, yeah, yeah.

Charlotte Ward: 6:00

Yeah, I I knew very early on I did not care to find the missing semicolon. Like, I just yeah, yeah. Because it was never the missing semicolon you thought it was either.

Matt Dale: 6:10

It was always a like those compilers would always fail like 15 lines later. And so I I remember working on a C project for class, and it was like, what’s wrong? And it was actually missing like curly brace or something, but it was it it didn’t fail until many, many lines later, and I just remember being very frustrated and I’m like, is this what I want to do for my career? Um but there’s a pretty clear answer to that, and it was not yes, so yeah, that’s why we’re here.

Charlotte Ward: 6:35

And uh, and unlike you went the you went the you know the liberal arts um path. I stayed in my computer science degree, but I took everything in it that wasn’t engineering. So I ended up doing all the like discrete maths, functional, you know, formal specification, uh uh information man everything, information management. I took a planets course at one point just for the variety to make up a couple of credits. Like I was there, but not. Do you know what I mean?

Matt Dale: 7:05

I hear you 100%. Yep.

Charlotte Ward: 7:07

It says a lot, yeah. Um we are um we are here. I’m gonna see if I can segue us in from being here, but not.

Matt Dale: 7:15

I honestly don’t know that we can segue easily, but let’s just jam it in and and and jump into the topic. Let’s go.

Charlotte Ward: 7:20

I’m gonna I’m gonna jam it in. I’m gonna jam the segue in from my last line. You’re gonna pretend that it’s a natural segue and then we can talk. How about that?

Matt Dale: 7:28

I love it. Do it, let’s go.

Charlotte Ward: 7:30

Let’s do it. Let’s do it. Just roll with it, just roll with it. So in in the in the in the spirit of being kind of here but not, you know, do it. I I think that sort of might be a good segue into today’s topic, which is extreme delegation, which is in some ways being there but not. Did you see what I did there, Matt? Right? I think I love it.

Matt Dale: 7:50

That was an amazing, amazing way to translate what we were talking about into something that’s actually what the listeners here actually care about, what they showed up for. So I’m I’m excited, yeah.

Charlotte Ward: 7:59

I think they would care about everything, but that maybe that’s just me thinking that people care about what I say. So I’m gonna assume we’ve at least entertained them for five minutes, and now we’re going to inform them.

Matt Dale: 8:09

If only we can just entertain them, that’s good. Lynn informing that that comes next, but lately at least we’ve entertained.

Charlotte Ward: 8:14

We can we can we can can but try. We can but try, right? Yeah, yeah, yeah. Um, all right. So uh see, I had a segue and you’ve ruined it. So let’s go.

Matt Dale: 8:26

And that’s the story of my life. I ruined things. That’s how I how I roll I roll. No, so like like talking about the topic here. Um for the audience, we got together a little earlier this week. Yeah and like you can tell with this, we just had a lovely time chatting and kind of getting caught back up in each other’s lives uh because it’s been it’s been far too long. Um but as we were talking through it, uh kind of a topic that that sounded like it had happened recently in your life and it really resonated with something that I experienced probably four or five years ago, um, but also kind of run into um in in different levels on kind of a day-to-day. It’s really that idea of um like we talk a lot about how do we how do we help our people who are are are under us, our director ports, how do we help them grow? Um we talk a lot about how as leaders sometimes it’s hard to delegate to let go of the things that we can do really well, but maybe someone else can not do quite as well, but at least it frees us up to focus on the things that we really need to be doing and that no one else can do. Um But there are there are times too where we find ourselves um in a situation where it ha we have to take that kind of to the next level. And usually that’s in times of stress. Um something crazy is happening at work, you’ve been pulled in a new direction, you’ve been seconded to another team where you have to do some different things, or you’ve been given a project that um is very big and busy and intense, um, or someone has left unexpectedly. Uh, I think my my my particular story we’ll kind of get into a little bit though. I I had a key um, you know, second-in-command lieutenant um that ended up leaving in the middle of kind of a complicated time at work. And when we’re in those situations when we’ve kind of broken out of our normal day in, day out, where things feel safe and fairly comfortable, but when we’re in those extreme, stressful, intense situations, sometimes we have to delegate. And and and that was kind of the topic that we we kind of came up that this would be something that hopefully will be helpful for for our listeners um as either looking at it from kind of a preparation, how do we get ready for this? Um, or what does it look like in the middle of it, or or I’m in the middle of this right now. Please promise me that this gets better, you know. Where wherever in the spectrum of that you might be find yourself, where that’s kind of what we’re gonna be talking about today.

Charlotte Ward: 10:33

Yeah, yeah. Um, you know, I I I was just um I I was sort of pondering this, and I’ve been pondering it since we last spoke. The the extreme part of extreme delegation, because I think, you know, you and I have both led teams in multiple organizations, formed teams, built teams, scaled up and down teams in multiple organizations. We’ve all we’ve been there, right? Um and uh in all of that, like the thing you first touch on touched on, which is like looking for opportunities to grow our people, like I that feels like be like BAU to me. Like you’re looking, here’s a task I’m comfortable with, I’m comfortable, I can explain, hand off, mentor, and I know just the person who’s to pick up this task or this little project or this kind of uh um some element of the role, you know, that you feel comfortable handing off. And I think that when you said when you talked about giving people opportunities to grow initially, I thought, well, that’s business as usual, like we should be doing that anyway. That is delegation, that’s not extreme delegation. And my mind just kind of went to of all things, this this is not an aside, I promise you. Of all things, the um do you remember that song that was released in 1999? I think it was the sunscreen song, you know, ladies and gentlemen of the class of 99. That one, the Baslerman.

Matt Dale: 12:01

Uh yes.

Charlotte Ward: 12:03

Yeah. Um it it was a he was dispensing advice to the class of 99, and it it was a headline advice was where sunscreen. But uh there’s a lyric in there, which is that the troubles in your life do apt are apt not to be things that are apt to be things that never crossed your worried mind, but the kind that blindsides you at 4 p.m. on some idle Tuesday. Um, and I was sort of thinking that’s that’s where extreme delegation lives. It’s in the unexpected, actually, and not in that BAU. Um, because BAU, you should be growing people, you should be creating opportunities. And extreme delegation, because you did go on to explain this, like to talk about this and touch on this. Well, extreme delegation, I think, lives in the space that you then described, which is where time and circumstance and uh you know organization like throws it on you as a necessity rather than just the the day-to-day expectation of any leader.

Matt Dale: 13:06

Yeah, I think it’s those those times that are that are intense and stressful that uh that is kind of what we’re talking about today, is really trying to go. And again, I think there’s an element of preparation that you can do today now. If you’re like, hey, I’m in business as usual mode, that’s wonderful, and we’re really excited for you. That’s a good good place to be. Um But I I think what what I’ve learned in my career, and I think again, we’ve talked, and I think you’ve shared that experience, is that it’s that four o’clock on a Tuesday when something comes completely off out of left field. Boss is like, hey, uh, can we meet real quick? Or again, maybe your your key, one of your key employees is like, hey, uh, you got a minute, and and and the whole perfectly crafted thing that you have in place and the way that you’ve got everything dialed and organized is suddenly either outdated or comes crashing down or or need to be like it going in a completely different direction. So sideways. Yeah, like so those are the moments where you say, hey, all right, you’re looking around and go, what are my resources? I’ve I’ve been given this new task where I’ve I’ve lost the key person, or something fundamental has changed. I mean, I’m it’s thinking back to you know the start of COVID. Um, that was uh one of those types of things where everything changed, and each of our businesses had to think about things in a different way. Were we gonna be able to meet our customers’ needs? Will we even have customers? You know, what did that look like? And so it’s typically something coming from external. Um, someone else has done something that then changes your world. And and the the the the place you find yourself in is how do I survive? How do I get through this period? Again, whether that’s freeing up space so that you can do the the new tasks that your CEO has given you, or whether that’s, you know, you you’ve had this lovely person that you worked with for years and you’ve trained up and they’ve been doing a fantastic job, and you’ve been delegating more and more and more business as usual, and suddenly they’re like, hey, I’ve I’ve got a great role at a new company, and and you’re excited for them and and you want that for them. That’s what you want to see as a as a leader is helping people grow and move into new and exciting roles. But all those things that they were doing are now on your plate, and and you’ve got to maybe hire someone new or whatever, you gotta get through a busy season. How do you make it to that point where you can live in that moment and and kind of go from there? So I think that’s kind of what we’re talking about today is okay, so something crazy happened, you know, where where do you go? How do we live here? How do we go from that moment and and uh and carry on? Um, so I think as we kind of look at that, as you’re starting off again, developing those relationships with your with your people that work for you, uh being the person you need to be to your to your boss or to the CEO, so they go, hey, yeah, Matt’s the kind of guy that can get stuff done, or Charlotte’s the kind of gal that can can can solve problems. Like you’re putting yourself in that situation, but it it’s it’s a good thing. And then when that lightning book comes from a blue sky or when that unexpected thing happens, what do you do in those moments? What do you how do you take stock of where you’re at and see what your options are so that you can kind of clear the field for that extreme delegation that we’re talking about?

Charlotte Ward: 16:05

And and it is it is interesting. You talked about a little there about the groundwork that you can put in. Like there is an element of prep you can do. And I think some of that prep is just like to your point, what you just came to there was like understanding what your resources are. And this isn’t something you can do at 3.59 p.m. on an idle Tuesday. You have to know your people, you have to know your tools, you have to know your data, you have to put the legwork in so that when it’s necessary, you can make quick decisions, you can hand things off quickly, you can bring people up to speed quickly, you can change tools, you can change tax. And I think that you know, I I think some of that is experience, but I I think that it’s not you know, and I know you’ve been in these situations where you have to roll in a completely different direction roll with it in a completely different direction at 4 p.m. on an idle Tuesday. That seems to be the theme today, but but that um you don’t get there like experience helps. It certainly does because you get practiced at doing it, you get practice practiced at doing it at different magnitudes, but but it’s not just experience that enables you to do that, and it’s not um it’s not, you know, a superpower in the kind of you know, it’s not magic. Like this is this is the fundamentals of knowing your job inside out and knowing what your team needs to do inside out, right? And I think that anyone at any stage of their career can put that groundwork in and should be for their own personal growth anyway.

Matt Dale: 17:47

When I I think you naturally are too, like as you grow in your role, yeah. Um if I think back to the things um that were a big deal early in my career, to the things that are happening now, uh, some of the stuff that used to stress me out a lot is is laughable. Um I I was a Boy Scout uh in my my youth. And um one of the projects in American Boy Scouts is you have to do an Eagle Scout project to get the highest rank. And I remember at the time, like, and it took me like a year and a half. You had to you had to do some planning, you had to organize some people. Um, and it was this really big, gnarly, crazy thing uh as a as a 17-year-old. Um looking back on that now, uh I my my kids are in scouts, and I was kind of like, what did you do for your project, Papa? And we talked about it. And looking back, I’m like, that was such a minor like I do these things multiple times a day. They’re much more intense and and and so I think again, if you’re a listener in this this show and and maybe you’re the early part of your career, you go, well, that sounds really, really crazy. What’s it like when you have have a situation like that? I think the things that you’re going through today, the the muscles that you’re developing as a manager, as a leader of people, um, those are the skills that you will need when that lightning bolt comes out of the blue sky or the sideswiped on a Tuesday, whatever, whatever that metaphor that you’re looking at, the things that you’re building up now are all skills and abilities that you need to be able to engage with um in that in that moment of of intensity or in crisis or whatever’s happening.

Charlotte Ward: 19:17

I agree. And I and I think that um this is I think for me, this is one of many reasons why I love leading managers and team leads. I love leading people who are early in their leadership career because you you communicate with them differently, you’re bringing them on differently, you’re helping them grow differently. And I think that um that first step into leadership from an IC role is quite eye opening. And it’s certainly just just um in case there’s any future employees of mine listening out there, um it’s certainly eye opening when you step into a leadership role underneath me because. I’m as transparent as I possibly can be about the realities. And I think that is something that at least I hope sets my managers and team leads up for success in the future. Like I I don’t have a formal speech, but I almost feel like I should. Like when you come in to report to me, like you’re going to hear things as as they truly are. Like you’re going to hear the limitations that we’re working inside. You’re going to hear what we definitely can and can’t do, what we should and shouldn’t do, and uh and my expectations. I’m I I don’t want to come across as like a demanding boss, but I think this is just about like for me, it’s about transparency. Here’s what we need to achieve, here’s how I think we get there. Get on board and give me your ideas because unless you fully engage quickly and early in your leadership career, I think that you’re going to continue to be surprised by the constraints and the you know, the bombshells on an idle Tuesday. And to your point, you can learn some of that in scouts, right?

Matt Dale: 21:06

Yeah, and early youth and in childhood, early adulthood, like there’s there’s things that we do that are preparing us for these moments of crisis or intensity. Um I I I I think too, as leaders, kind of building on that point, I think it’s important to share and be transparent with our people, but it’s also important to show our work. Um, I’ve got two folks that I’m working with uh in my current role. Um and we we just got out of a meeting this morning and it was with the marketing team, and a couple junior leaders on that team, and they were they had an ask for us. Um, and we left the meeting, and one of my director ports said, Wow, that’s not how that’s not how you show us to do stuff. Like, there was no like, hey, let’s have a nice interaction first, let’s kind of warm each other up to this task that they were asking. It was like, let’s go. There was, you know, uh one of the people was like, Well, there’s no foreplay on that one. And it was, it was like, yeah, like as we think about our interactions with people, as leaders, we’re modeling the behavior that we want our subordinates to learn and to see. And it was really cool for me because it was like, I had intentionally, like, I hadn’t that wasn’t one that’d been explicitly like showing my work, but both of them were like, oh, this is this is how we should be doing things, not like they did over here. Wow, that’s such a contrast to what seems like is is winsome and what seems like we’ll get the job done. And so um, so yeah, like I think I think being able to share transparently, being able to model the behavior, showing our work to say, hey, this is how I’m thinking about the problem. What are you folks seeing? Where where are you at? Let’s let’s engage in discussion and and and hopefully get to something that it at least is good as what I was thinking about, but hopefully it’s better because it has the context from those other people that have a different perspective.

Charlotte Ward: 22:46

Yeah, and and that thinking, I think, like showing my work, but also explaining why I’ve reached why why do I report on this thing? Why do I pull this number in this way with these exclusions and this constraint and this narrative? It’s because of constraints, it’s because of, you know, how I want to present to a customer or to the business. Like explaining yourself is the first step to being able to hand things off, isn’t it?

Matt Dale: 23:16

And so to kind of come back to our topic at hand, because I think I’ve driven us a little far afield here, I think that groundwork that we’re laying with our people today is what then allows us to, when something changes, to say, okay, situation’s different. I always recommend taking a little time to think about things. So when I one particular example, my boss came to me and said, Hey, Matt, I want you to be moving into an operations role for a six-month period of time. I’m gonna bring in a person to replace you temporarily, a consultant to replace you temporarily. I’ve worked with her before. She’s fantastic. I need you 100% out of support for six months so that I can have you working on this other stuff for the whole customer experience team. Um, he’s like, used a very British trainwork. I’m gonna second you over to this other team. You’re gonna be working directly with me, you’re gonna be doing a bunch of stuff that’s scary that to me was very scary at the time. But I need you to hand everything off to this person. And also, by the way, we’re going through um several acquisitions that are gonna then result in some layoffs. And and this is all gonna happen while you’re there, but not there, and your team needs to have this continuity. And so, like, I took, okay, I’ll do the job because that’s what you’re asking of me. But then I took a little bit of time before I then touched base with the people that reported directly to me that I had a good relationship with. Said, here’s what’s gonna happen. You know, here’s what’s going on, here’s what here’s how I’m thinking about it, here’s how you’re gonna be okay. Because I think in these situations, people often go to, what does this mean for me? Is my job safe? Am I safe? Is this gonna be okay? Is this thing, this hard thing you’re asking me to do? Is there an end of the light at the end of the tunnel? Um how do you help meet their needs? And again, the first step is giving yourself a little time to think through your emotions, having a chance for those to kind of come down from, oh my gosh, I’m terrified, or this is horrible news. Yeah. Yeah. Being able to breathe and say, okay, I’ve processed, I’m I’m ready. Now let’s look at this clearly and say, let’s make a plan.

Charlotte Ward: 25:05

How how long do you think you should take to process?

Matt Dale: 25:09

I I think it I think more time is better, but often in these situations, we don’t have much time.

Charlotte Ward: 25:15

Exactly.

Matt Dale: 25:15

So I think it can kind of depend on the on the context. In this particular case, I there are three examples of extreme delegation in my career that I’ve been kind of thinking of. This one that I just shared was um I had basically that afternoon. It was like a three o’clock on a Tuesday, not quite four, but it was it was close to the end of the day. Um, and I had some time to think about it. And I just said, hey, great. I’m gonna, I I didn’t have anything major going on the rest of the day. I took a walk around the building and then I then I went home early and and had a conversation with my wife. I took another walk. I talked to a close uh friend um who was in a different business, but we’ve we’ve been friends for a long time, and really just trying to kind of wrap my head around first of all what I was being asked to do and the changing scenario that I found myself in. And then, okay, now that I’ve kind of thought through this, what does this mean for my team? How can I set them up for success? They’ve got this new person coming in. Nobody knows this new person. I don’t even know this new person. I’m I’m I’m accepting her based on my CEO’s, this is what we’re doing. Um, and I’ve worked with her before, and she’s great. Okay, so I’ve got to I’ve got to build out a plan so I can get to know this person rather quickly. I can hand off cleanly and clearly the whole part of my organization. We have 60 plus people in the US and the whole team in the uh in India. How do I, how do I neatly put a bow on this, hand this off to this person, and also set my direct reports, my my uh directors and and my leadership team, the managers and team leads, how do I set them up for success to be able to welcome this person and have the continuity that of this thing that I’ve built that’s been very stable and safe and that we know how to do stuff. How do we how do we weather this next six months? Um, and and again, getting my head right. I had the luxury of that, that day, that evening, talking to the people, being able to come in the next morning and share the news with my direct reports and giving them time to breathe, you know, take the morning off, go think about things, go get some coffee, whatever. All right, let’s come back in the afternoon and start kind of planning what this looks like and be able to start building an action plan rather than having to dive in right away and process emotions at the same time.

Charlotte Ward: 27:10

I I think you use the word uh there’s a couple of things I want to draw on there, but the first thing I want to draw on is a word you used, which is, you know, make them feel safe. Safe is the word that really where my ears pricked up because I think under huge change, whether it is growth or reduction or you know, I’m stepping out for a period of time, but I’ll be back, and that you know, there’s a you know, workload is gonna shift significantly to the left, whatever it might be. Um that safety is is what like really the first principle we should put into play, I think, when it comes to extreme delegation, because extreme delegation to your point, to the recipients of those tasks, those roles, those responsibilities, it can feel like more work, it can feel uh risky, it can feel exposed. And I and I think and you know, and it can feel uncertain at best, you know. Um, I’ve not done this before because that this is the nature of it being extreme. It’s not that data that you handed off some reporting to three months ago. It’s this is an extreme situation. And so reassurance that you’ve got this, they’ve got this. This is actually something that if you all sit and think about it together, you’re actually well prepared for, even though in the moment it doesn’t feel like it for a minute. Just take that minute, however long you need, process it at all levels, yourself and the people you’re delegating to, and um establish the ground rules would be like part of that like safety, you know, like this is what’s gonna happen. These are the boundaries. This is if you can time bound it or change bound it. These are the these are the parameters in which we’re gonna be working for a period of time. Yeah.

Matt Dale: 29:07

And and also kind of giving them that escape clause or the the hey, if things are going sideways, or if you’re you’re worried, the this is when you can come bring me back in. I’m I’m I’m not available maybe 100% of the time, but in these cases, or if you’re feeling this way, please, I’m here. I want to see you succeed. We’re gonna get through this. Let me know. Raise the flag. If it’s not working out, in this case with the with the the new gal that’s coming in to replace me for six months, and you’re stressed or you’re having problems communicating with her, we don’t know who she is. So come come talk to me. I’m here for you. I I I need to be focused on this major project. We need to figure out a bunch of stuff and and you know how to how to reduce costs and and make the make the board happy, but but I still have time for you in the in these situations. So giving those rules of engagement, and here’s what I need you to do, but here’s how I’m here for you, and here’s when you can raise the flag. I think those are really important to kind of again build that safety, let the people know it’s gonna be okay.

Charlotte Ward: 30:02

Yeah, because ultimately this is delegation, not exit. And so you’re still at the end of a DM or a Zoom or whatever, if they need to talk things over. You can you can re-explain stuff, you can reframe thinking, you can be a sounding board if the parameters change suddenly, right?

Matt Dale: 30:19

But or even an advocate, right? Like if some if they need something, I I have a I have more weight perhaps than they do in the organization. And I can if this person that they’re bringing in, she ended up being fantastic. She was awesome to work with, love her a lot. But in that early moments, it was like, who is this person going to be in? And if if they need me to advocate on their behalf or on our team’s behalf, I want to make sure that we’ve got that clear communication so they feel safe. And that safety and that that relationship is the stuff you’re building in the business as usual time, right? Like that’s the foundation that you’re laying that then allows you to be successful in this time of extreme delegation.

Charlotte Ward: 30:53

Yeah, yeah, a hundred percent. I think reminding them that you’re there, uh, that safety, that trust, all of that is is, you know, BAU leading into the and advocacy is a huge one, I think, as well, because I think advocacy, if they raise the flag in a timely manner, you know, is it’s a superpower when it comes to the person who is delegating, handing off those tasks, that work, those responsibilities, that accountability, even. In in some ways, the accountability isn’t theirs, but you want to, yes, the buck does still stop with you, it should, but but you want them to not feel like they have no agency because they they, you know, the just because the accountability is ultimately still yours, you want them to feel that agency. And and having your advocacy in those situations significantly improves their feeling of agency, I think, and uh self-determinism. And and the the other point I would make in that landscape is that being the ongoing advocate with to your point, like more weight, more, you know, uh more visibility, more accountability, like visible accountability. I’m I’m using a lot of words here, but you know, ultimately more more more connectedness to the business, more used to speaking to a to a different group of people to uh at a certain level. Um that advocacy can also help limit the parameters if they are threatened in any way. So it’s not it’s not necessarily about just uh you know, helping that person build that agency or build that visibility themselves, but also, you know, this is support and things get thrown at us all the time. And so while you might set off with good intentions on that idle Tuesday or Wednesday morning, um, that to say, right, this is what’s going to happen for the next six months. Before you know it, two months in, something else has happened. There’s a product launch or there’s an acquisition and things change again. And when the parameters change significantly, it’s probably you that has more weight to say no. That’s not reasonable under these circumstances. And here’s why I think we should stick to the plan we made two months ago or whenever it might have been, right?

Matt Dale: 33:17

And I and I think that’s a good point, the the fact that things change and that we need to be able to re-evaluate and and and uh change with them. And and to do that, as we talk about how do we how do we do extreme delegation well, that’s being connected to the person that you’re delegate or the people you’re delegating to and making sure that it’s not just uh, okay, here you go. I’m I’m gone for six months. Um good luck. Like it’s a there was very much intentional time on my part through that situation where I was still meeting with um my two um uh directors that were reporting to me and and just saying, hey, how are things going? What’s what’s going on? When there was a big change, we had a we had a rather unexpected uh group of people that um were terminated for cause and it several were on my team, and there was there was a whole kerfuffle and there was a lot of organizational change and things weren’t going super well as often happens in in software as a service and and private equity companies. Um through that process, I was much more engaged with the team. I was working with uh the person that had come in to step in. We were we were making some of the plans that um that if it wasn’t extreme delegation time, I would have been making, or with my with my direct reports, the three of us would have made. We had a had a four four four-way conversation. We talked through some things, we provided context to this person that was coming in and having to you know sit in this meeting saying, Hey, you no longer work here, to some of the folks, and being able to provide that context and hopefully give them dignity and keep the team stable throughout the whole thing. Um, that requires you to still be engaged. It’s not the same as, okay, I’ve I’ve handed this thing off uh during business as usual time. A lot of times than that, you still want to check in and make sure things are okay, but sometimes you can go, cool, like I’m completely done with this thing. I think in extreme delegation, you still need to have your finger on the pulse, you still need to kind of know what’s going on on the stuff that you’ve given off, because otherwise it may make it very sideways and and and then it you have to come and fix it later. And it’s better just to kind of stay on top.

Charlotte Ward: 35:15

I I agree, I do agree, and ultimately that accountability is yours, that hasn’t gone. So so I there is not a world in which I don’t want to understand the things that I am accountable for.

Matt Dale: 35:27

Yeah, exactly. A lot of negatives in there, but I get what you’re saying, yeah.

Charlotte Ward: 35:32

Yeah, I I fully want to understand my remit and the success measures that are being applied to me as an individual and to my and then and through me to my team. So yeah, absolutely, absolutely. Um, and I I think that you know check-ins, whether they’re informal, whether they are formalized, you know, I’m still gonna like you’re gonna do this, but we’re gonna have half an hour a week or something. There’s m there’s a spectrum of ways in which you can manage that accountability, those touch points, that reassurance, um, and that, you know, mentoring, frankly. Um the other thing that strikes me um as important in this landscape, and I don’t know if it’s the final piece, but it’s certainly a key piece from my point of view is extreme prioritization.

Matt Dale: 36:21

Yes.

Charlotte Ward: 36:21

Um, because you, as somebody full-time in that role, will be trying to do all the things or have your team do all the things while you innovate at the edges, while you develop, while you forge a path forward on one or multiple branches at a time. But you can’t expect someone stepping in in a sort of pseudo emergency, let’s face it, it’s an idle Tuesday going into a Wednesday morning at this point. Um, that you can’t expect someone stepping into that to pick up all of the threads of your thinking with equal priority because you’ve already done a lot of that prioritization. You’re you’re you know doubling down on this thing over here while you’re exploring that thing over there. If you just hand off all of your files and say, there you go, that’s everything. Like there’s no way you can expect someone to pick that up reasonably and successfully without saying these are the important things. If you concentrate on nothing else, get this right. This thing over here, if you’ve got time, great, love it. Continue to explore, report back to me because that’s that’s longer term thinking. That’s probably when I’m going to be back in seat after this six months project. And uh, you know, we could work on it together at that point. Like that’s an up another opportunity, right? But extreme prioritization, I think, is critical. And you have to communicate that really clearly. These are the things we are doing, these are the things that we can leave. If you do nothing else, communicate that.

Matt Dale: 37:57

Yeah, and I I think kind of at its core too, when you talk about prioritization, what are the what are the things that are need-to-haves for us to survive? And what are the things that are the nice to have’s? And the nice to have’s all go by the wayside, right? Like, yeah, if we can get them, great. But what what’s our core function? And I in organizations, it like you said earlier, it’s very easy for support um to be seen as, oh, let’s have them do it. You know, like this is this is we’ll we’ll have them do this project. We’ll have them and during business’s usual normal times, we can plan for that and we can build bandwidth. Um, but when something extreme happens, and one of my other situations was actually both of those direct reports from that story ended up leaving at different times. And and I ended up doing some extreme delegation when each of them left because I went from having two people that were highly competent, that would work together for years, to one person. And on the job search, trying to find someone, was it gonna be internal, external? Um, and then bringing that person in and helping train them up and get them going. Like that was another type of extreme delegation where I was in charge the whole time, but my workload went from my normal workload to I have a full other person’s workload that I’m trying to do and the stuff that that the senior leadership are asking me to do and accomplish for our team. And so I think in those cases, you have to sit down as you build that plan and as you talk, look at your resources, whoever’s around the table with you, what do we have? What can we like, what levers can we pull? And what are the things that we absolutely must do? And and what are the other things that we’ve been doing that are nice to have, but they’re not the absolute must-dos. Let’s make that list, let’s prioritize it, like you’re saying, and then decide we’re gonna do these things, but we’re not gonna do those other things. And it may involve, like we had a conversation with leadership on one of the other situations where this is the customer experience we’re going to be delivering. It is not what we want to be delivering, and it’s not doing all of the things for our customers that we would normally do. But because of the situations in this time, this is what has to happen. And and and getting that buy in from up above, like you said earlier, knowing what you’re responsible and what you’re what you’re being held accountable to, those are the things then. That that if you can redefine some of that because of the extremeness of the situation, that can help you and your team be successful as you move through it. And so again, prioritization, but but kind of redefine what are we trying to do, or let’s get back to the core. All right, let’s let’s we let’s make a plan and then let’s take a care of it and do it.

Charlotte Ward: 40:17

Yeah, and sometimes it is coming back to the core, and sometimes it’s quickly investing in things that are going to accelerate, like make things easier in the super short term, but that actually do have long-term gain. I mean, I have a very similar parallel story, which I won’t deep dive on, but in a three-week period, one um well, actually, I suppose in a in a in a month, we brought in a new AI tool, an AI co-pilot. One of my support managers gave notice on very good terms, super pleased they were going on to a really good role. Um, and I was handed program management at a whole business transformation level and had to backfill that support manager position. So that all happened in like a five-week period. Um, and it was like dominoes one after the other. And so there was a period of like two months, whereas managing a program, managing a team, onboarding a new tool and hiring. And it like that was three jobs for a few months there, you know, effectively. And uh the thing is that the AI tool would have if if that come along four weeks later, I would have said, There’s no way I’m gonna invest any of my time in that. We just happened to just bring it in-house a couple of weeks before on trial. And part of the prioritization was, you know, this this actually has the opportunity to help us move quickly with new hires and everything, which suddenly was a priority. And uh it’s like we should probably double down on AI of all of all the ludicrous times to do it. Um, let’s just like really accelerate that part of, you know, it w it started as an experiment, but like we just need to go for it at this point and make it work. Yeah. You’ve got to know what’s important.

Matt Dale: 42:05

You do, and I I think just listening to you share that story too, like that’s sort of a perfect storm of everything lining up in all the wrong time to just cause craziness. And I think as leaders, one of the things that we need to do is sometimes those times happen. And so that communication as you negotiate with the senior leadership and you talk to the people that are your direct reports, I think you also have to be looking at yourself and saying, am I doing the things that are going to allow me to be successful through this really rough time? Am I am I getting enough sleep? Am I eating the right-ish foods? I’ve never wanted to eat really great foods. I’m I’m I’m terrible. But in general, like, am I doing the things that take care of my body? Am I doing the things that take care of my soul? Have I communicated with my family? Do they know that it’s gonna be like these things all just lined up? The, the, the, the, the mom that you were gonna be, or the dad that I am, or the spouse that that we are, like the people in our relationships, we need to be thoughtful about what that effect that has. Because sometimes you just need to gut things out. And if there’s nobody else to do the job and you’ve pared it down as much as you can, and you’ve got the prioritization as tight as you can, and you’ve got the resources lined up as perfectly as you can, there’s still maybe some very long nights. And you know, often we’re on a salary position rather than hourly, because our part of our role is expected to, in those times of crisis, be able to pull together and and get it done. And so I think just like you’re checking in with your people, you need to be checking in with yourself and with your personal life, with your family and and friends to make sure that at least you’re communicating and at least they can see the context too. This is this is a six-month second. I’m gonna be doing this thing. We’re working on these major projects. I think they’re gonna be done in in three months, and things will get better stairs step down from where we’re at right now. But right now we’re DEF CON 5 or whatever, and it’s it’s creating maybe DEF CON. We’re in a bad situation, and we’ve gotta, it’s, we’ve gotta get better. Um and I and I and like to my family, maybe I need I need your support right now, you know. Yeah, maybe I’m gonna be asking more. The things that I do around the house are gonna slip a little bit, and my my kids need to step up to help Papa and get things done.

Charlotte Ward: 44:06

Oh, I wish. I wish.

Matt Dale: 44:08

This is the perfect world, right? Yeah.

Charlotte Ward: 44:10

Yeah. I’m gonna, I’m gonna, I’m gonna uh I’m gonna close out on one final thought there, which is something you just said about getting it done. And I think the positive side of all of this is that you probably wouldn’t be in any of these situations unless you had the reputation of someone who gets it done. And um, and I think that that’s the lesson that we and the opportunity we have to give our our uh you know reporters who are being the recipient of all of this extreme delegation. Like it’s it’s the lesson that it’s you know, you get it done. Like that, that’s actually that’s what we do in support. And and that’s that’s why these situations are handed to us, those projects or whatever that cause these idle Tuesdays to sweep us sideways. Um, they’re given to us because we get it done. And we we there through that we create the opportunity for people we’re handing stuff off to to demonstrate that skill as well. And I think personally, I think there’s almost no greater skill on the planet than getting it done. So um I’m gonna take that as a positive in every respect.

Matt Dale: 45:22

No, I I love that. And I think too, as we reflect on who we’re delegating to, they’re also the people that get it done. And this is a chance as we have that dialogue to say, look, um, I’ve been called into this new thing, or we’ve we’ve had this situation thrust upon us. Um I’m leaning on you, I’m delegating to you because you have a track record, because you’ve proven yourself to be the type of person that gets things done. I can rely on you. Let’s partner together, let’s build that, let’s build out a plan, let’s let’s figure out who’s gonna do what, let’s divide the pie. Um, but together, we’re gonna get this thing done. And when we come out of it, um, this is a this is an opportunity. This is a this is something that will grow our business muscles, our problem-solving muscles, so that when the next opportunity happens, the next thing happens, like we’re going to be leveling up. And so there is a benefit to this, even though it feels really tough right now, even though it feels like this nasty thing that we don’t want to do. Um, we have a chance here to look at this and and frame it in a way that is this is good for us and gonna help us be better um when we get it done. So yeah. Extreme delegation, all kinds of fun.

Charlotte Ward: 46:24

Extreme delegation. We got it done. Uh what a what a fantastic what a fantastic discussion. Thank you so much for meandering through this with me. Um, let’s let’s call this a wrap for today. We got this one done. Thank you so much for spending time with me after all this time, Matt. Will you please, please come back and record another conversation with me soon?

Matt Dale: 46:42

I would love to. It’s just such a joy to be here. Thanks so much for having me back. I’m excited that the podcast is back up and running, and I’ll definitely be back in the next couple of weeks and months.

Charlotte Ward: 46:54

That’s it for today. Go to customersupportleaders.com forward slash two eight seven for the show notes, and I’ll see you next time.

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