Part 2: Burnout, Jaded Techs, and Growing Without Becoming That Guy

Seeing signs of madness, the screen.

Tara says tomorrow.

After caffeine. All right, chat's working.

This is working. You guys ready to light this candle?

Right.

I'll do proper intros in a second.

Oh man, unfiltered questions could be dangerous.

Just giving folks a few moments to decide they want to spend their middle of the day with us here.

I feel like I should be like kicking my feet, like just kicked something under my desk.

So, uh, while, while we're waiting here just a moment, um, just kind of talking about like, uh, the music, retro culture, all of that. My wife, who's an elementary school teacher, Was getting ready to leave this morning and had on— she always gets like very— takes her job very seriously, dressed up. Her dress had big poofy shoulders, which to me totally reminded me of like an '80s prom dress. It's just so funny how like little details become cyclical like that.

I think we're live.

No, we've been live. Yeah, some nonsense for a minute, you know, just Are you wearing a shirt that has the cup design on it?

Well, yes, I am.

That is awesome.

All right, friends, I will, uh, run through some intros here and then we will get into it. If you're watching live, we'd love to hear you in the chat. Otherwise, this is recorded and will be available for consumption Later. I am being dangerous and attempting to use the built-in slideshow presentation feature of Restream, which I don't normally do. So what could go wrong? Let's see if, uh, the first person who taught me I could do this, if Ray Orsini was here right now, he would either be really proud of me or, uh, really, really embarrassed for the mistake I'm about to make in doing this. But before we get into today's episode, that is a continuation of our talk around burnout, answering your questions, wonderful viewers, all zero of you. I have a little surprise. So one moment.

Phil, watch out.

You love shows signs of high-functioning burnout. Have you experienced any of the following symptoms working? Through lunch saying no worries when there are in fact many worries, becoming the backup plan for an entire department, answering Slack messages with the emotional tone of a hostage negotiator, or quietly turning caffeine and spite into billable productivity? If so, you may be entitled to join a class-action lawsuit against your own brain chemistry. You may be owed compensation for Unpaid emotional overtime. Excessive tactical vigilance. Chronic I'll just handle it myself syndrome. And damages related to being described as such a rockstar instead of being given actual support. Not a real lawsuit. Results may vary. Side effects of high-functioning burnout may include irritability, silent resentment, mystery shoulder tension, and becoming weirdly good at pretending you're fine. Call 1-800-TOO-MUCH today! I'm definitely not a real lawyer. All right. That is actually in— there's a course on Empath about burnout, and that's in the intro to the course.

Oh my God.

So if you don't know who I am at this point, it doesn't matter. Let's actually talk about our guests. I have with me the amazing, amazing Tara Brummer. Or Tara Rumer, if you want to be annoying, the Chief Community and Ecosystems Officer at ImmieBot, who has done many things, but most importantly has allowed me to be the godfather of her beautiful puppy, Divinus.

You really have got to take away your license for AI, babe.

I didn't make that image. That was not me. But that chin, that chin can cut glass right there.

That chin does not look like my chin.

That is the jawline I put a crown on right there.

Oh my God, just keep moving on.

Tara, the final point there though is what '80s movie would you live in?

Oh, uh, Sixteen Candles.

That's easy.

I had the biggest crush on Jake Ryan growing up. I had a shirt that had his face on it. Nobody that I was friends with knew who that man was.

Sure, I'm curious since we're asking this question. Matt Topper, what '80s movie would you live in?

Oh, I mean, it's got to be, uh, Major League. It's one of my favorite movies. Interesting.

See, I would have thought you'd given the same answer I would give based on our conversation behind stage. Topper and I both played the saxophone. I would go for The Lost Boys, and I would be the sax guy at the concert at the beginning of The Lost Boys.

There you go. That was just not a bad choice either.

I would perpetually live in that moment. And We have another guest with us. Who the heck is Matt Topper? I mean, he's got a bunch of professional credibility, but he's also the guy who started the single largest collection of MSPs anywhere, the subreddit r/MSP, and then created this monstrosity and very politely dipped out and said, not my problem, someone else manage it.

Pretty much.

Matt, what do you do day to day?

Good question. Everyone else is wondering that too. I spend a lot of time speaking, facilitating IT Nation Evolve groups, working on the other IT Nation events. And in my free time, like I'm doing an award speech here, I like to go running and fitness and other stuff like that.

Is it ever gonna get tiring of people knowing you as the guy that started RMSP?

You know, somehow that's like the one thing I got known for. Like any other— like I could cure cancer tomorrow and Started MSP would still be on my LinkedIn profile.

Yep.

You know, if you look at it a different way, and I would say the same thing to Martin who started Lab Tech Geek or Kelvin, you know, with his forum posts, you're all people that saw a need And realized that equity and availability of information was more important than yourself. And I think that's kind of cool because it is increasingly hard to have that kind of impact on the world. So I think it's a cool thing to take credit for that you connected all those people to share information and also to yell at each other and crap on each other's business practices.

That's the fun, right? We don't need positive reinforcement. We need internet trolling reinforcement.

Exactly.

All right. Um, if you've never seen a Managing Up before, which is entirely possible because we don't normally broadcast these live, the point of this series— it is an empath livestream meant as a continuing live education course to help empower emerging leaders, employees, and people at the MSP that want to know more about being in charge to start taking their first steps down that path. And as I have grown to regret over the last 2 years, every episode comes with a workbook page. Think before you speak, kids. That's a lot of effort. If you'd like to go ahead and download that workbook page for this episode, the QR code's right there. Same one we used on the last episode because I said I don't have time to make new workbook pages. The other ones are fine. Even though Princess, who's behind the scenes as our producer, was up my butt and created scheduled tasks for me on my calendar to do it anyways, which I ignored. So grab the worksheet. Uh, with all of that out of the way, last time we were talking about burnout, and specifically we were talking about high-functioning burnout, which is something that all of us individually have gone through and we see is a super common thing to happen in a helpdesk environment. First, quick refresher for anyone who doesn't remember. Generally speaking, burnout is when you've had enough, exhausted yourself mentally and emotionally. Traditional burnout, your performance and attitude tend to degrade pretty visibly. Functioning burnout, you power through even though you're dying inside until it becomes too much. Similar, but they have a different result. And Generally, Topper and Tara and myself, I think, all represent this. You could suffer from high-functioning burnout and still be sparkly and get everything done, even though you are dead inside. And that is why it is so insidious and such a problem in our space. And this type of work tends to reward that headspace. So with that, uh, sort of quickly out of the way, we had said last time, send us your questions so we could talk about them. And so That's kind of what we're going to get into here. Um, there's not that many questions that I picked. I think there's maybe like 6, so we have some time to chit-chat around them. So starting with this first one, how do you stay empathetic when you've answered the same question 500 times? Um, you start with Matt on this because, you know, before he was an internet celebrity, Matt actually worked for a living.

Oh, man. So I see a couple things here. And I hate to use the consultant it depends answer, but I think it does depend whether you're talking internal or a client question. I used to get asked the same things from internal people all the time. And I kind of did it to myself. I was described as the answer vending machine. After some time, like to the point where it hindered the rest of my team's development, right? I would just immediately solve problems for them. And one of the best things that I eventually learned how to do with this was to, you know, really not answer these frankly. Now, sometimes it was that blunt. Sometimes it was, I'll get back to you, but it's going to be like 2 days before you get an answer to your email. kind of stuff. And the way that I really handled this was trying to teach my team to be a little more self-reliant and, you know, watching over it, right? Like, based on the question, you could kind of tell, is this a real emergency that a client's going to be seriously impacted by? Or is this something that is worthwhile for that person to spend some time floundering for the betterment of their own career and development?

That's right.

And when it was the latter, My solution, and what finally did this, was to not answer them. Like, just spend more time and say, I'll get back to you when I can, and make them wait a little bit. For clients, it's a— you can take that tactic a little bit, but not quite the same degree. Usually it's a general reminder that one, stop emailing me directly, stop texting me, calling me, whatever. Depending on what it is, that could be a conversation with the primary contact at the client, or you have a problematic user, things like that. For internal stuff, though, which is really where the big frustration came from, the teach a man to fish adage sums it up pretty well. That's—

I think there's a bit of a spicy take buried in there. You know, you're so Demure that you, you downplayed it, but you, you said that you stopped answering, which I think there's, there's a lot of wisdom in that around burnout in general. Tara, you look like you have thoughts on this.

I do. So I actually did kind of this. It doesn't mean I'm not empathetic, but I also stopped answering, I would say, as quickly. So we all get the messages constantly on Teams, on Signal, on whatever you use. Slack. And I found that if I would give people a quick answer, they would come to me with another question that could be the same one or a different one. But I had now trained them that I could just give them the answers that they were looking for. So I started just delaying my responses. And usually people would be like, oh, don't worry, I figured it out. Like, if you give somebody 30 minutes without a response, and I, I just don't like having my chats up, I find them to be a distraction. Um, especially if I'm actually trying to get shit done. But I actually have something on my desk, and I've had it— I rewrote it, um, the other day, but it's been on my desk for years. And it's, if I'm being asked the same question 500 times, I have to kind of look at myself and go, okay, is it the same person asking the question 500 times, or is it a different person that just maybe is uninformed? And on my, on my sticky note, it literally says Is this a people problem, a process problem, or a technology problem? Because usually it comes down to one of the 3. So instead of answering that question for the 500th time, I'd go, okay, maybe we didn't document this. Maybe you can't find the document if it is documented. How do we— what's the roadblock of people finding their own way?

So all of us have, at least now, are in, I don't know what I could consider to be some sort of leadership role. So we do have some freedoms extended to us to manage our engagements a little bit. What if you're level 1 on the help desk and you're suffering from this, where either your coworker or a client is asking you the same thing over and over again, and you, you can't, you can't take longer to answer. You can't deflect. You can't really do anything other than just do it. How do you stay empathetic and not get angry? In that situation, any tips for any of our poor frontline people?

You know, it's going to sound dismissive, but if you think you can't take longer to answer, you probably still can. Like, and what I mean by that is if there really is an overreliance on you, or if there is some resourcing issue, no one's going to know if you keep playing Superman and superhero and just solving the problem anyway. That becomes the default. You almost have to be okay with causing some pain, which is hard for us. We tend to empathize with our coworkers and our clients that we want them to be friction-free and everything goes smoothly. But if you're overloaded, you have to let the symptoms of overload show in the end result. So I would say that you do have time to take longer to answer because you're overloaded and let the rest of the world and company and see that.

Well, and I think some of it is being honest with— if you're a level 1, you clearly have a boss, right? So it's, it's the honest conversation of, hey, like, I'm answering the same questions 500 times from— it's vastly different if it's an internal staff member versus a client. Clients, I'm sorry, guys, we just have to deal with it sometimes. Like, we have to put our personal feelings to the side. But that can be an education point because maybe you're not getting your work done now. And I've had, I've had staff, our technical staff come to me with this. I can't get my work done because I'm constantly answering questions for this person. So that is a person problem and a process problem because realistically, there should be a process for this, right? But you have to be having that conversation with whoever's above you that can help you.

So I, I like both of your answers. I'll offer up a non-empathetic engineering-only answer. This, this is an equation with a known variable. If, if we know we're answering a question this many times, we should be able to predict for that and design a better situation where it doesn't happen. And I, I think all too often, especially those of us that are subject to just doing it. I have messages sitting right now in our Empath Slack that are driving me crazy during this livestream because I feel rude not responding instantly, even though no one's asked me to. Uh, is— and engineer out the conditions at play. If there's a question that has to be answered this many times, the answer being given clearly isn't clear, or resources that are available to answer it aren't clear, or the end user's desire to find them isn't easy or clear. There's a variable we can eliminate.

Yeah.

That's a great place to go because maybe you can't turn off your brain's ability to answer the question 500 times. So just prevent the question from being asked and maybe that'll solve it.

Yeah. Um, not that I'd necessarily advocate for this, but kind of along the line of my original answer is sometimes the solution is to answer the question and then miss a deadline that you said you could meet. Not necessarily a good thing to be doing. But if the reality is that you spend so much time answering questions that your own work can't get done, let that come out.

That, kids, is called scarcity. You can learn that and more in Matt Topper's Guide to Sandler Style Selling, available now.

Funny.

So let's move on to our next question. This one is, it's kind of a long question, but I really like it because thematically, it's aligned with, I think, an increasing problem that we're going to see more and more of in our space with burnout. So with AI implemented in most businesses, management seems to think that we can just Do more. I mean, literally, it is a magical efficiency multiplier, right? The feeling of finishing a project and celebrating that moment has vanished with it. The will to go above and beyond because team members know there is no pat on the back, just a new list of things to do. So what's the best way to stay encouraged and motivated when the goalpost keeps moving? Before either one of you answer, I just want to say to whoever wrote this, you deserve a hug. You are clear. Seriously, like, whoever wrote this, you do. You've been in some pain and I'm sorry and you deserve a hug and you Your company does appreciate you, even if they're not telling you that. So, Tara.

Dean, I want you to answer this one first. I have to think about my answer. I knew you were gonna call on me, and I was like, I don't have an answer yet. Well, because I was gonna be like, listen, can you make the question bigger so I can read? Sorry, I'm the worst. Okay, go ahead, you can talk.

Need some glasses there? So I think the, the basically what's being asked here is not a new problem. It's the scale and the speed of it. Because really, if you've been— not if you've been a sysadmin, but if you've been MSPing for a while, then you already understand part of our job is to do more with less and build efficiency. And we also know that generally speaking, in the workplace, high-performing, competent employees are often rewarded with more work, either voluntarily or against their will. Those are known things. It's just AI makes this now like, oh, whoopsie, like that all can happen in like 30 minutes instead of over the period of like 6 months. We've experienced that here at Empath. I've talked to partners that have experienced that. I'm sure both of you have engaged with MSPs that are experiencing this, or even internally at your own organizations. And I don't know that we really have a good answer yet on the right thing to do other than you need to be able to communicate workload and capacity. We all have a finite amount of capacity and efficiency multipliers, which most tools are efficiency multipliers, can trick you into thinking you have a lot more capacity than you do. This is true of any tool. Uh, being a protector of your own capacity, necessarily protector of your calendar, but just a protector of literally what you can get accomplished within a given timeframe is really, really important because your manager, whoever's asking you to do more work, I guarantee you they are not doing it because they disrespect you or don't care. In their head, they don't really visualize your capacity the way you do. And they're assuming, I think generally, you would speak up if You were overcapacity. You're a funnel. And unless that funnel is plugged or clogged, they're just gonna assume, put stuff on the funnel, and the funnel's working. So very broad strokes here, but I would say in general, if this is happening to you, without complaining, you just need to kind of raise your hand and say, hey, I need to slow down a little bit, or that's one thing too many, or I need to share this, or we need to bump out the deadline, and then be able to explain that just because AI has been involved and has sped up a piece.

Yeah.

doesn't mean that it's actually reduced your capacity to execute the task magically. I don't know. What do you two think?

I think you hit it when you said this isn't necessarily a new problem. One step forward is in the wrong direction. Yeah. Shit. I just lost it. This isn't a new— sorry. This isn't a new problem. MSPs and IT people in general are freaking terrible about celebrating wins. And we are really good at moving goalposts. So I think some of this comes down to, it's really hard when you're the staff member. And I'm speaking to staff members and leaders here. Stop moving the fucking goalposts. Like, sorry to curse, but you have to know when done is done. And at that point, don't immediately tack something else on. We actually talk about this a lot with EmmyBot. And when we're doing like these long drawn-out giant parts of the product that we want to build. After that point, we stop and we say, okay, we did this thing. Let's give them some quick wins. Let's give them something fun to work on. Let's give them something that's not going to kill their brains because they've been building this part of the product for 6 months straight. It's balancing that, right? And I think the efficiencies we're gaining doesn't mean we need to fill every second of every single day constantly. Because if you keep doing that, your people are going to get so burnt out so fast. Like, if they did something faster for you than you expected or you projected, if you have the ability, give them a day off. Give them something. Like, reward them for doing something great for you would be my opinion. But that falls on leadership. But it also, like you said, Dean, it falls on the employee to have that open conversation. Before getting to that burnout point going, my capacity is reached. I get that AI made this easier or faster. It doesn't mean it didn't take my brainpower to actually get AI there.

I don't, by the way, like for anybody listening, I don't do a good job of that personally. We're launching 2 new products and both of them in theory need somebody to do a bunch of client-facing materials for it. And recently on a leadership call, it was just, and Dean, you're going to do this and this. And I was just like, Okay. Which, what I should have said is, gosh, like, that's way too much to do on top of what I'm doing. We need to stretch this out, or I need to involve Caitlin on our team to help with that. And I didn't say that. I just went okie dokie.

And so, so Israel Lang, years ago, he was our facilitator in Evolve peer groups. I will never forget sitting in there and he said, you overestimate what you can get done in a short amount of time and you underestimate what you can get done in a longer amount of time. So I think a lot of that is the realistic goal setting on the front end. And I will say, God, I love you tech people. I love our devs. I love our technical engineers. You people think you could get everything done tomorrow. That is even with AI, that's not usually the freaking case. So like you need to, maybe you need that third person to come in and go, okay, I'm going to be in charge of saying what the final thing is, what good looks like, or whatever you want to call it. And then we're going to spend a little time. And we bought— we threw— and we bought a birthday party one time because like we hit a milestone. And instead of just starting on the next thing, it was like, no, we're gonna, we're gonna buy a cake and we're gonna throw a freaking party because we did this thing. But somebody has to be accountable to actually making sure that thing happens.

I asked John O'Brien in the chat, um, how he handles this on his service desk, and he said not well because he's not well. Does the same thing. And I would bet, and, you know, John, feel free to chime in or not, uh, but my guess would be that acting this way is largely what has helped you get to where you are in your MSP, you know, because, because at a certain point, this— we talked about this in the last episode— some of this burnout behavior is what makes you successful for a while until it isn't. And gosh, is that a hard thing to turn off in your brain if there's a pattern of behavior that has generally worked in your favor for a while, to then stop or to dial it back suddenly. I mean, that goes against everything we, we know. Um, Matt, what about you? What do you think?

This is, um, there's a lot of nuance to this issue more so than I realized when I originally read this question. So I actually see a couple of things that are somewhat intermixed here. One is the feeling of finishing a project and celebrating that moment. I won't speak for anyone else, but for me, even at my busiest, at most burnt out, that never went away. It was immediately followed by, I have all this other work to do. But I never stopped getting that, you know, almost that like accomplishment high when, when something finished. With, with AI and the move to automation, that's turned into something more like I just found a new thing to automate. So there, that's still a good feeling. And the will to go above and beyond is, for many of us, what got us to this point in the first place. Um, I think though, it's really interesting, the flip side of this issue, which is that, yes, there, there is a risk of burning out techs and staff and employees. But there's also on the employer side, this idea of, if all you do is make your team more efficient, without filling in that extra time, all you've really done is increased your cost without you know, getting any more work done. So it— both sides really need to play on this.

I— that's a really, uh, salient point. I was having dinner last week with one of our BDRs, um, who I don't know if he wants to be named in public, uh, but this is somebody who dials people all day and is mostly told no. And, you know, has a quantity of dials he estimates. There's this It's a shitty job. I wouldn't want to do it. All of you that do that for a living, you are, you're the real MVP. And he was making a comment because they're, they're now using Claude to kind of help with, with lists and planning. And he was just saying to me, I feel like now I no longer have the time to focus on quality because so much of what we're doing with AI pushes me towards quantity. And for like, for those that, that may or may not know, Alex and Wes certainly aren't in the office telling people do 1,000 dials a day and make them crappy. I mean, they, they want quality dials, but I, I thought like, what a great observation from that BDR to be like, the tools, the process make me feel like I have to rush for quantity and can't take a minute to focus on quality. Which I understand. I, it's, uh, I remember having this problem when BCDR stuff first started becoming mostly automated of like, oh cool, our backups are now, you know, pretty much like report on themselves. This is great. And you almost start to dial back on the quality because of the quantity.

Yeah. And then I like, I don't want to fixate on this issue too much, but I also want to be cognizant of if the net result of you implementing AI and automation is that your utilization drops to 20%, that's not sustainable either.

Sorry, I forgot how to use Restream for a minute. Sorry everybody, I just gave you all a headache. Um, Matt, I don't know if you saw it, but when, uh, I had John's comment up, he just ran a half marathon on Monday. So he's a fellow runner.

Nice.

Matt, John, if you're still watching, Matt's one of the lunatics that does the fun runs early before large conferences, so you can go find him.

We take them super slow. It's a fun run.

There's like you and Brandon Martinez and John Harden are all like super serious, and then there's all the rest of us.

Yeah, me and John, Brandon, and, uh, Who else? Oh, and Brad.

Josh is the runner as well, right?

Yes, yes he is.

And, uh, I'm probably eating breakfast or sleeping in. Uh, so next question: how do you stop carrying responsibilities that were never actually yours?

I literally am building an entire slide deck about this right now. Well, rebuilding it and why delegation sucks. So.

I, I'm, if possible, Tara, can you give us also a version of this for the regular peon level employee? Unless that's what you're already doing. Sorry.

Well, it's for both, right? Because you're, I was the peon level employee for a long time, but I kept taking more and more and. Some of it relates back to, I think, question 1, where people are constantly asking you the same things. You're training them to come to you, which means you start carrying these responsibilities, right? So I think the question that even your basic-level employee would have to ask is, I can help with this, or does this belong to me? Because I don't know if you guys have ever heard the, like, what is it, like the something about pass the monkey or like the monkey's now yours or whatever. I don't remember the parable that goes with it. But I think as high performers, level 1, level 2, level 3, it doesn't matter. We are accidentally, because we are the problem solvers and we are the superheroes, we start carrying other people's responsibilities. And some of that is on ourselves to, to take that step back and be like, no, um, like, I'll answer this for you. However, like, I can't do this moving forward. Like, you have to set boundaries. Boundary setting is not bad. Um, that's something that took me a really long time to learn through my career. I still am learning it, I feel like. Um, and I think in small companies, like, it doesn't matter what kind of company, even like a level 1 employee, you feel a lot of ownership for things and you put a lot of pressure on yourself. And so you just start naturally taking these responsibilities over.

This is my version of the monkey, by the way.

Okay.

For those, for those that know.

Uh, I don't know. I don't get it. Maybe Matt does. But yeah, that's how you end up with 12 hats. And, um, just because you're capable doesn't mean that it's what you should be doing, I suppose. And you have to set boundaries. If that all made sense.

It does. What do you think, Matt? How do you stop carrying responsibilities that never actually yours? As a man who carries responsibilities now that were never actually yours.

So I read this as different than a delegation type problem. I read this more as a, like, support desk person who's doing something that's technically outside of their JD and somebody else should be doing, but they're— they believe so strongly in trying to keep the lights on that they just take it. This one's tough. This one is going to take some coordination. This is not one where I would advocate just letting things slip as easily as I would have the previous question, just because you're, you're likely going to have some more significantly negative outcome when the company's processes all of a sudden— now, I'm not saying be okay with doing all this extra work, but I am saying without— I was trying not to just say, like, talk to your manager because it feels like such a cop-out answer. That is part of it. What you need to do is make it clear with whoever is responsible for work, your manager, whatever department work you're doing, or whoever, that this is not sustainable, that you're not able to do your regular tasks. Or if for some reason you're the right person, you should have been the right person to do this all along, then you need to drop something else or make it a officially part of your job description. That's not something you can do yourself. To me, this is not one that you can self-fix as easily. You need support from the rest of the org to really get past this.

That's a good take because there's— I think you both have addressed different levels of this. There's definitely— there's certain things that sort of a tactical or a micro level are small responsibilities that you have just picked up that you probably should just stop and delegate. But then, as Matt's pointing out, there's other things, you know, maybe, maybe at your MSP, maybe your MSP is under 15 people and you're the only tech that can log in and really manage all the security tools. And it's not technically your job description, but if you stop, no one does it. And then it's sort of de facto. your problem. And I was trying to format this small enough so I could drag the Karen hair over Matt when he said talk to the manager, but I couldn't do it quickly enough.

Listen, it's so often the right answer, but I feel like I'm cheating when I just say that as, as my answer to stuff. Like, yeah, duh.

Yes and no, because most of the things— think about all the issues you've had internally within your company and what is like One of the biggest feedback that we get from clients, it's how shitty communication is. And so people— like, it may feel like a cop-out answer, but people don't like to have an uncomfortable conversation because they don't want to feel like they're less helpful. Um, internal issues with this? Yes, absolutely, internal issues. That was the private chat, wasn't it? Uh, absolutely. Like It's every company has it. Like we've had a company, our company for 20 years. This is something we still struggle with. And it's not that we're not having the conversations. It's that sometimes we're not having the right conversations, I would say. And we're assuming that people can do more or we've, we've kind of always been the company that was like, oh, you picked it up. It's yours now. Well, something is different than ownership.

To that point as well with communication, once again, at a macro level. What's the easiest way to ensure that communication is handled perfectly? Just do it yourself. If you're the only person that's going to do something and you have full accountability and authority for it, well, you're the only one that has to communicate or be communicated to. And it kind of goes back to what we talked about with burnout. That works initially. It really does. Like, you pick anything at either, either one of your organizations. And if you just said, this is mine, go away, and you just took 100% control over it for a period of time, that's effective. The thing is, it breaks down over time and then it becomes less effective and you have to either dump more effort in to keep it going, hence the burnout, or you start looking performatively incompetent. Um, I would bring up one other take on this, and this is just myself. Uh, there are times where there are responsibilities I'm carrying. that are not actually mine, but someone has to do them. And then I don't want to give them up, even though I do. And I'm curious if either one of you ever had that happen in your brains at all. Um, there, there have been— for those who don't know, here at Empath, I manage effectively what would be like 4 or 5 departments worth of work because someone has to do them, and I just kind of volunteered to do it. Um, when we hired Mike Riggs, uh, Mike volunteered to take over support, which is actually would have been a huge weight off my shoulders and something I secretly wanted. And I got bitchy because by that point it was like, I don't want this, but also mine, hands off, go away. I do support. You'll do it wrong. And like, it was an almost irrational response. I'm curious if that ever happened to either one of you. Like, you have this— you've actually had now the opportunity to get rid of her. Oh yeah, it wasn't yours. And when that moment finally arrived, you were like, actually, no, no, that's, that's mine. You can't have that.

Yeah, for sure. You get attached to it, right? It's the same issue that you— that we always have around delegation. There's this, um, belief that it won't happen as well, that different people won't be able to do it to your standard, you know, etc. And there's also just frankly like an emotional attachment to some these, you almost feel like an ownership of it, kind of the same way at MSPs, when you have a client you're responsible for, you start to think of it as like your client, not the company's client, right? It's, it's very hard to give up after a while, which frankly, you know, there's some organizational thing if you have a belief that it's your client to begin with. But if you have a job duty that you don't want to give up, I don't think In almost any organization, nobody has said that your job description can't change and that for that to become part of your job officially. I think it does require a conversation of based on capacity, what do you have to give up to make that part of your job? And is there somebody else to pick up the slack? I think it's worth acknowledging though that it's not always an irrational thing to think like that, to think that, hey, I found something I enjoy doing and I'm good at. Let's see if we can find a way to officially make this part of my job description based on what other, other things I'm responsible for? Sometimes it is, sometimes just the needs of the organization don't allow it. But have that conversation, right? See if, if there's a way to do it. What I wouldn't recommend doing, what I've seen happen all the time is, you know, being told to give that away to someone, silently brooding and like resentment building. Don't do that.

My toys.

So you said something really important, I think, Matt, there. You said something you like doing. So years ago, I did this before I had a leadership title or a director title.

We—

I did an accountability map, basically. I wrote out all these different roles. I think I probably pulled it from online, all these different roles within MSP and I started filling it out. And I was in like 30 of the boxes. And so I was going, oh my God, how am I functioning? And then we started, like, I started diving through it and going, OK, what is something that realistically shouldn't be in my role? Because they were those quiet things that I just kind of picked up. And so I did this exercise without Brett and Darren's knowledge. And it was like, no, I actually have 4 jobs that we probably need to hire for. We need to have this conversation that I'm splitting my time, which means nothing's being done really well because nothing's becoming a focus. But in doing that, there were things I didn't want to give up because I was good at them and I was fast at them and I liked doing it. So it was like that quick hit of adrenaline and just dopamine that you get. Like, I don't know, for our neurodivergent people, I need that with my ADHD. And so I love procurement. And I loved quoting. I could knock— it would take people hours to build a quote. It could take me like 12 minutes and I would be done. Um, and no one understood. And it was because I actually liked doing it because I was getting that quick hit. So I think it's the— there's an exercise like got it, want it, capacity to do it or something. Um, I think that's really important that maybe you sit down if you are feeling over overwhelmed. Doesn't matter what your role is in a company because our small companies, your job description is fluid. But writing down kind of everything you do and being like, is this realistic for my role and does my job description need to change or is this helping in the trajectory for what my next role should be?

Sure. I think broadly with this question, this is more, more evident of a problem at a smaller organization because just simply if you have a small number of teammates, Regardless of your role, everybody's going to do some sharing of responsibilities. And I really liked the way you, you, you framed that, Tara. I also think this is super common at larger companies that tend to have very distinct carved out roles. I think it's a little less risky until you have sat in that role for a very long time, whether you have a senior title or not, when you're a senior person in that role, this also tends to happen. And one of the things that Tara said, I think, is a really good tactic to kind of bring it back to when we were talking about burnout, the cost of output. Having agency, that is taking it from something I do to something I am choosing to do in light of an outcome or with an intentional trade-off, is very helpful. Like Tara's saying, these are 4 different roles we ought to hire for. It doesn't mean You can hire for them today or maybe even in a year, but now it's documented. Now you understand I'm choosing to continue to do this and we have a plan at some point with this goal to hire one person for this part of it. That's very helpful for your brain just to help manage this type of stress and not just keep absorbing.

Well, I think it's helpful and it's helpful for leadership to know Because they— God love Brett and Darren, they are not the most intuitive, or, um, they don't notice things. And so they're, they're deep in their own heads doing their own shit, as is probably everybody else in your company, that they may not notice you're struggling. They may not notice that quiet stuff that you're just taking. So when you build it out that way and you go, okay, I am actually doing all of these different roles. Well, if somebody's already in that role, the question could come up of why aren't they doing that? How did this fall onto you now? Right. It may open some uncomfortable conversations.

Yeah.

I think, um, trying to think how to say this exactly. Um, Response—

dealing with responsibilities that weren't really yours is also kind of hashtag startup life and small company life. And if you're in that kind of organization, you know, without— right, nobody go back and say Matt said quit your job, but think about if that's the kind of organization, like, are you— if you want something siloed and more defined, it may make more sense to be with a bigger, more established company.

Is it right for you? I think I mentioned this in a group chat this weekend. You have to take into account what's right for you at that time. Startup life is not for everybody. MSP life is not for everybody. And if it was 5 years ago, that's totally fine. But you have to think about— Quit your job. But I agree with you. Don't just Marie Kondo your whole life and be like, I'm quitting everything. But maybe, maybe that's your indicator that you're not at the right spot. Absolutely.

I mean, this is, gosh, startup, not counting my MSP that accidentally stopped being a startup. This is startup number 4 for me. And I both hate all of what both of you just said. But also I keep signing up for this because I secretly love it.

So I love the chaos, in all honesty. Like, I— while I have a pretty defined role in what I do, I love knowing what, you know, the devs are doing. I love having some input in our product even though I'm not on the product team. I don't know that I'd ever leave a startup. or like a small company, honestly. And I will say this, I have worked with a lot of large companies and they run like startups. There are a lot that don't have this shit in place. I've been in peer groups with them and I've had a lot of conversations about it where it's shocking the amount of process and other things that we have been able to put in place that they are not able to get in place because now they're so large, they're having to play catch up and it's just not worth their time at that point.

John O'Brien's also a masochist and says it's the good kind of addiction.

It is. It is. I love it.

So this is, I think, the same question framed differently. I'm the person everyone relies on. How do I step back without screwing over my coworkers? And of course, the answer is super simple. Just document everything and store that in a file repository and leave, because that's all you have to do, right?

Jesus.

That's it.

Until no one looks at it.

Duh.

Well, don't say that too loud. You might offend the people who founded the company I work for. You mean people won't just learn just from reading something? So, but seriously, how do we, how do we do this? I actually, let me ask, uh, Tara, you first, because when I first met you, you were 100% of the event and sort of field marketing for IMMI, plus the coordinator and the scheduler and the event planner. And eventually you stepped back from some of those roles and you ended up actually bringing in another person. But how did you do that without screwing over IMMIbot?

What do you mean? I mean, the reality, the reality is you shouldn't be in the same place forever. And if— unless you're really comfortable with that, right? That wasn't like my best use of time. Um, and once we started doing— when we were doing 12 events a year, I could do all of that. That was— that was— we're up to 30-something events a year. It's not realistic, especially if I'm the traveler. I became the bottleneck very quickly. And then I started seeing the gaps of the, you know, the partner success wasn't getting done, the this, that, and the other wasn't getting done. And it's just because my time was so taken up with the minutiae and the logistics that I brought somebody on that I know is very good at details and can do the logistics. But I think I've always said I'm trying to automate and hire my way out of a job, every job I have. Like, it's, it's the reality of it, because there's always something else I'm going to need to do, right? So I became a single point of failure, I would say. And you can't, you can't have that, right? So some of this comes back to when people ask you these questions, and, and, and people rely on you for stuff, you start redirecting them. This is where you find that. This is how you find this. You start helping them. You start training them on these things so that you're not. And that's a big— if you look at me, Anna, and Kayla now, for most things, both of— 2 of us at least know how to do it. So like, if I speak at an event, Anna can give almost every talk I can give. Now, the ones about leadership and building teams and building companies, she can't. Um, but most of the things I do, one of the other two know how to do. I— you, you wanna— guys, I wanna take a vacation. Like, people can rely on you to, to know, you know, you gotta— I think some of this comes from— sorry, I just keep talking— but some of this comes from the, the, the need to hoard information To feel relevant. Oh geez! And once you get past that, I love not being involved in decisions. It is one of the most freeing things when I'm like, "Oh, you guys hired someone? Cool. Moving on with my life." Like, great. Maybe I'll meet them at some point. But it's it's having the reality that I need a life out of this this company. Like, I need autonomy from this company, either of them. Sorry, that was just a rant. Did I answer? I don't know if I answered.

Yeah. Matt, what about you?

So I think Tara nailed this, that the only thing that I'll add without just repeating the whole answer is if you want to minimize the amount of damage you do or the amount of disruption you cause in the— in your organization. The answer to this question is that you have to do it gradually. It is not an overnight fix to get yourself out of this. Now, you, you can decide that overnight, I'm just going to go back to verbatim what the JD says, and that's all I'm going to do. You will cause a lot of problems in your organization, most likely, if you decide to do that. And, you know, nobody would necessarily fault you for that. Like, I get the whole Yeah, you know, I need to get my personal life and work-life balance back in order. If your main goal is to do this without causing disruption, then set yourself up for a decently long journey to solve this. It didn't get this way overnight, then it won't get back to a balanced state overnight either.

Uh, I think you two answered this brilliantly, so I'll do what I did a couple questions ago, just give a very engineering kind of an answer here. Uh, the building, building a system that can exist without you really requires designing it at the lowest common denominator. And doing that initially requires a level of process design and almost procedure that will cause resistance both from yourself and from others. But that is the cost you have to pay to Take your cognitive excellence out of whatever it is and make it so other people can do stuff. And like Matt said, it takes time. And like Tara said, you are making yourself effectively replaceable, which, by the way, uh, you ever want to freak out a boss, uh, talk like that about how you're designing a system to make yourself replaceable because you're thinking like an ops person. They'll just get scared that, uh, the rock star said scary leaving questions, which is a good segue. Into our next question here. What do you do as a leader when you learn one of your better performers is looking for another role? Well, that's very easy. You break their legs. No, you don't. Done.

No, you don't. That is not what you do.

Oh, no, no. I remember you taught me this at CanITCon. Uh, you hit them in the face with the non-compete and the non-solicitation and tell them you'll sue them into the ground if they even try to cross you, right?

Absolutely. That's exactly what you do.

Perfect.

Legalese will save us all from anyone leaving ever. No.

What do you do? That's what you do, obviously. I mean, I, I see it as 2, 2 separate things, right?

Yeah.

If they want to stay and they're not because of something like pay or job responsibilities or something, then yes, maybe you can work with them and figure it out. If they're leaving because they just found like the coolest job ever, like, that's just— be supportive. Or if there's— if they are leaving because they found some salary that there's no way you can match, or there's some position they want that you can't match, then You know, I don't want to be holding them back. And I think the reality is a lot of the time, by the time someone is actively looking for a new career, even if they want to stay, it's, you know, they're probably leaving anyway.

Yeah.

Um, so I think you hit on something, Matt, of you need to find out— it's not need, but it would be nice to understand why they want to Right. Because I know in the past when we've had people leave our companies, because we're not huge on firing people, we'll try to save for better or worse as many people as we can. We took it pretty bad. Like, it was almost like a breakup. Like, they are rejecting us. And that's not the reality. At some point, we just said it earlier in another question, startup culture isn't for everybody. Small business culture isn't for everybody. Maybe it's just not a fit for them right now. Maybe they've got personal things that they just need to handle. Or maybe they've— maybe they found their dream frickin' job. But the reality is, as a leader and as people who are owning or running companies or a middle manager, your job isn't to handcuff people into working for you. That is the fastest way to ruin your culture, right? So I think opening up the conversation as to the why are they looking, can you accommodate so that they won't, or if it's something that's fixable, right, or something that they want to stay, it's just XYZ problem. Or, well, no, I mean, the point isn't to handcuff everybody into your company. to, it's to build a culture they actually want to stay at. So while I've never formally looked for other roles elsewhere, I've been approached by other companies, right? Um, but there's a reason I stay with Brett and Darren, and I have through 2 companies now. It's they've built a culture and companies I, I believe in and I want to be part of. Um, so I think, I think Get curious, uh, and don't do what so many— I have heard this from so many companies— don't immediately panic. Don't immediately treat them differently. Like, I've heard people start treating others horribly when they find this out, like, like they're a traitor. That's, that's not what they're doing. Like, don't get defensive.

Yeah, yeah.

Don't get me started on, uh, on non-competes.

That last, that last part right there. And I'm a big fan of doing this. I'm managing up to always try and get employees to get in an owner or a leader's headspace. Uh, I was guilty of that early on. I, very black and white in my mind, you know, uh, a contract is a contract, a job, you should be loyal and you're working here. And the first MSP I worked at, the owner there, Nathan, hi Nathan, if you're watching, he taught me. This thought that like, kind of like scorched earth never benefits anyone, even when it feels good. And so you got to remember that like most of the time as employees, when we actually communicate we're looking for another role, it's typically either combined with an ask or it's something that got its way to our leadership without us telling them. And so putting yourself in the leader's headspace, that can come across either as an ultimatum, which is going to trigger potentially a negative response, or they can feel like almost it was dishonest because you didn't tell them yourself, even though you're not obligated to. So knowing that, I think, is good because it, it just tells you as an employee that, like, you're not a bad per— first of all, you are not a bad person for doing due diligence. Just like we would say to any of our MSP clients, there's nothing wrong with doing due diligence on the vendors you use. If you work somewhere for a while, there's nothing wrong with thermometer checking how the industry is going, what's around you. That's okay. A good company that you want to work for, you will choose to continue working there. That's not the same as actively looking. And so it's just kind of learning a little bit of that headspace and giving your leadership a little grace. if they don't react perfectly instantly, just as much as they ought to give you some grace. And, uh, I think generally if you're a leader who's watching this, your job, like Tara said, is not to handcuff people. Although in the state of Massachusetts, you can handcuff your employees to their desks. You just have to handcuff everybody equally with the same handcuffs to the same type of desk. Um, I'm not joking. Uh, you can get away with quite a lot in right-to-work states as long as you apply it equitably.

I do have a question, though, because it sounds like this is a, this is a leader of a company. And if this is a high performer, and you're surprised, are you surprised by this would be my question. If so, are you having conversations with this person regularly? What is your cadence to talk to this? Like, why, why didn't we know that something was wrong or something was changing? Or are we not doing one-on-ones?

Like, Just the distinction there. I, uh, what Tara said, why don't we know something's wrong or changing? That's the question, not why didn't we know they were looking. It is unlikely that most employees will have a relationship with their supervisor where they're going to feel totally safe saying, hey, I'm thinking about looking for another job. They're probably just going to say the second part of that sentence, the things about their current job that are frustrating them or bothering them or stressing them out. So. I think what Tara said, just sorry to interrupt. That's, that's a really important point.

But that's the thing is people don't typically just up and look for another job unless there's some kind of stressor or financial or they're overworked or burnt out. Like you need to be having these conversations ahead of time so that you're not slapped in the face when a high performer wants to leave. Right.

Or like, like we said, when we presented on high functioning burnout in London. Somebody with high functioning burnout will lie to you when you ask them this question directly. And in their mind, it may not even be a lie, but they will lie to you. And that is just something you have to learn how to look for the signs of output and the cost of that output to see through that in high performers. Because I've— Tara will tell you, I've had stressful months here at Empath where I've complained to her about something. If One of the boys were to call me and be like, how are things going? And be like, great. Because first of all, I don't want to burden them with, you know, enough they got to worry about as founders of a startup. But secondly, what do you do in that situation? So you have to learn to look for those signs. And in a company that I think generally has a healthy culture, someone is doing that within the org, even if it's not your direct supervisor, which it's just, it's always good to communicate internally and Uh, if you're a coworker of somebody that is struggling, um, I'm not saying go to HR and be like, they're looking for another job, but maybe that's something that you say to their boss at some point. Like, hey, I've noticed that Bobby, Susie is coming into work every morning on time, but they've looked exhausted for the past month. Maybe we should talk to them.

Yep.

So you just, you don't know what you don't know. It's kind of my whole point here with With what I was saying. So whatever side you're on on this, just remember, we don't know.

When you're a leader, you really have to get— I mean, it's such a vastly different skill set than like an individual contributor, right? You have to get really good at reading people and like those micro just things. It can be even just like a change. I said to someone one time, I can't remember who it was, but I was like, They're smiling at me and they're nodding, but there's like no smile. Like, their face isn't like— they're not happy. You can usually see it in someone's eyes or in, in their mannerisms, etc. I'm sorry, did we just skip a question?

Well, because we're out of— we're out of time.

Uh, I think we need that question because I think I know what it is.

We're out of— we're out of time though.

Uh, I can't go back. Oh wait, can I? Wait, was that me? Am I doing that?

Yes.

How does Princess manage to deal with Dean and not go insane?

We don't have to answer this question.

We're all wondering.

Uh, my question is, is there anyone sane at Empath?

I would just like to point out, and I learned this from Tara, I am a delight. First of all, I should have worn that shirt.

Next time we'll have Princess on and we'll only ask her questions about Dean.

I mean, I'm fine with that. Princess, it was really fun to talk to you. Unfortunately, we have run out of time talking about this subject yet again because it is such a good subject to talk about. Kind of on a related topic, on the next episode of Managing Up, we are going to have on some technical guests. I believe we're going to have our director of engineering, Chris, and Mike Riggs on. We're going to talk a little bit about why technical people understand more than technology, or the best really ought to. And it's going to be a fun conversation around how your engineers cannot just be the stereotype of the basement-dwelling, sunlight-afraid sysadmin anymore. They, they have to know a little more than tech. And They probably do. So we'll see you there. Um, Tara, Matt, thank you so much for joining me today and putting up with me.

Where—

uh, that's not correct. I should have pulled that slide out. I'm sorry. I'm gonna say, uh, where can people see the two of you next if they'd like to?

Matt?

I'm doing a lot of local type events. Probably won't see me too much. I guess I'll be at IT Nation as my next big industry event. But until then, it's a lot of, you know, one-off shows for MSPs and their clients.

Very nice.

I'll be at the dog park with my dog.

It's Tobias Toblerone.

He's like, Dad.

Hi, Toby.

I will be at PAX 8 peer groups next week in Dallas. I am speaking to some groups, I'm presenting during a lunch and I'm presenting during the community day, so come say hi. I am doing IR games with you, I think, this month?

Yes, it's going to be the end of October. It is wizarding themed, unless we want to get a C&D from Warner Brothers, They made me—

I've never, I've never done it.

God only knows. Princess wants me to be Draco.

I want to be Luna. She told me I'm Hermione. Um, and then I will also be— Ali will also be at IT Nation Connect as well, uh, with, uh, Darren and Brett, the founders of Immibot. And then I think we're helping out with the community pre-day that Rocket Fuel is putting on. And then I will be headed over to Australia for— I'm not— I just got back from that one for Kaseya Connect APAC. So I've got a lot coming up.

I was trying to figure out how to turn your video upside down, but I couldn't do it in time.

He's so cute.

Oh, here we go. We did not have some of these LinkedIn comments in chat during the stream. That's my fault. Sorry. Kayla says she's a delight.

She has a shirt on right now that says she's a delight.

Mark says he's not only insane, he's out sane and besides sane.

Besides sane, see?

Nice.

And that episode of IR Games, we— October 23rd. This is going to be the first time I've done a serious IR Games and have not had Amanda Doucette on my team to carry the actual thinking weight of the Exercise for me, so a little nervous about that.

Yeah, I don't want to have to think. Is this a thinking game?

Kind of. I mean, we're doing a lot of different fonts.

Oh great, great.

And I'm just going to spend the whole time just casting spells and being in costume.

So we're just having fun here, guys. Great.

All right, friends, thank you so much for joining us. I gotta end the stream or princess will beat me. Thank you all once again. Have an amazing rest of your day.

Bye, Toby.

Bye. Bye.