In this episode of the Make Work Not Suck podcast, Daniel Steere and Ryan Hodges dive into a scenario every business leader dreads—what happens when the boss goes on vacation? Whether work derails while they’re away or chaos erupts when they return, this episode unpacks the real reasons why things fall apart and how to stop it from happening.

From the visionary vs. integrator dynamic to the frustration of micromanaging from vacation, this episode addresses the hard truths of why work sucks when leadership isn’t around. You’ll hear firsthand experiences, including Ryan’s recent vacation-turned-nightmare and how a lack of strong leadership led to a “shit show” of a week for the team.

Key Points:

• Why many leaders don’t take enough vacation—and how it affects business.

• The importance of having a strong integrator in place to keep things running smoothly.

• How poor planning and miscommunication turn a simple vacation into a disaster.

• Strategies for leaders to prepare their teams before taking time off, and how employees can step up to ensure smooth operations.

Timestamps:

• [00:00] Work Sucks When the Boss Goes on Vacation

• [01:02] The Reality of Team Function When Leadership Is Absent

• [02:36] Why Leaders Don’t Take Enough Time Off and Its Consequences

• [04:25] Ryan’s Recent Nightmare Vacation: An Ineffective Integrator

• [06:17] The Visionary vs. Integrator Dynamic Explained

• [07:47] Why Work Falls Apart Without Strong Leadership

• [09:45] Micromanaging from Vacation and the Consequences

• [12:43] The Importance of Preparing Your Team for Your Absence

• [15:48] Senior vs. Junior Teams: Handling Time Away

• [23:54] Why Junior Teams Fail to Think Long-Term When the Boss is Absent

• [27:06] Leadership Mistakes: Returning to a Business That’s Not Ready for Growth

• [30:11] Vision, Journey, and Results: The Key to Keeping the Business Moving Forward

Whether you’re a CEO struggling to take a break or a team member frustrated with lack of direction when the boss leaves, this episode is packed with insights on how to keep things running smoothly. Don’t let your vacation become a work disaster—listen now and learn how to avoid it!

Is your team ready to run without you? Tune in to this episode of Make Work Not Suck and discover how proper planning, communication, and leadership dynamics can keep things on track when the boss steps away.

[00:08] Announcer:Welcome to the make work not suck podcast.

And the guy is away with when the boss is away, work is, like, you know, cats away, mice at play, but then when the boss comes back, it's a it's a nightmare and the next 2 weeks are hell. And so we fear when the boss goes out. I don't know.

[00:52] Ryan Hodges:the office. And I know this topic came up because I literally just got back from vacation and with pressure most of the time for everything that was going on. So

I was like, so does anybody work? Or, like, how do how do we get things done? I think a lot of this really depends on the seat that you're in. Right? So so let's talk about it from the boss's perspective, because that one might be probably the there's probably the most to unpack there.

So from the boss perspective, I would say, first of all, there's most of my clients, most of the, the business owners, CEOs, visionaries, entrepreneurs that I've worked with, most of them do not take enough vacation. And so I would say that's probably part of the problem, is they're not getting their batteries recharged, doing whatever it is that they do when they're not at work. And over time, just, you know, we all tend to deteriorate if we're not taking good care of ourselves, and I think vacation is an important part of that. I think the reason though for that is because most of those leaders haven't built an organization that can function without them.

Right. So I remember almost 2 years ago when I started working with tier 11, the CEO owner Ralph went on vacation literally, like, week 2. Like, we the first time I got with me was the quarterly meeting. Like, I joined the company, spent 2 days with the CEO at a Indian Reservation Hotel in Florida, and then 3 days later with the leadership team. And then, like, 2 weeks after that, he was out of town for in Taiwan for, like, 2 weeks.

Okay. It it was very successful, but I think that came down to you had the new person that was eager to jump in. You had a leadership team that was eager for change and, you know, been there, done that. Right? Like, that was my whole reason coming into the business was to to help turn it around.

So it was great for him. I mean, there was the pulse checks and, you know, how's things are going, but he came back to a company that had already made, you know, progress and changes, and it was great Right. Versus that was not my experience over the last week for me. It was the complete opposite. It was absolutely a shit show.

[03:52] Ryan Hodges:Yeah. Yeah. Well, man, this is one of those, like, cobbler shoes. Right? Mhmm.

Is there so many things going on? There's so many components, and I think it's one of those I'm probably I'm probably gonna air out too much dirty laundry here. I I think what the ultimate thing that came out of it is a ineffective integrator. Alright. So I can be the visionary or the integrator.

You know, I'm, like, 98% integrator, 96% visionary or vice versa, I don't remember. But the problem is I can't do both at once.

[04:37] Ryan Hodges:I fail miserably, especially if I try to be the integrator of my own vision. I I fail miserably. And so in this scenario, there we have a junior integrator of a young lady that is very talented, very smart, very bright, but not experienced as an integrator. And what's happening is when when I had stepped away to be with well, for 1, I was on I was, doing a bunch of consulting workshops the previous week. I came home, was home for, like, maybe 48 hours, then the whole family flies out to California for a week long trip.

And so what what the the crux of this was is nobody really knew what to do, and I had an integrator that was too junior to be able to carry the vision, the team, etcetera. And then what happened is because she wasn't sure what to do, she went right into tactical mode, almost a little bit of visionary herself and coming up with ideas and trying to drive. And all we do is create chaos. Well, here I'm on vacation, right, with my family and and and some family friends is a very important trip that we're on. And I'm having to micromanage from afar because my integrator is not experienced enough to lead the company.

That's the crux of it right there is if you don't have a solid integrator to drive the leadership team and drive the business forward, then what you end up with is having to micromanage. And you know what? There's example this morning. I'd literally just got back from a one on one with another CEO of another company about literally the same problem. He can't go on vacation because he he when he's disconnected or when he's away, things don't move or the metrics slip, and that comes down to really, it's having a solid integrator.

Having a solid integrator.

And those two people desperately need each other. They don't always naturally gravitate towards each other, but, and you're usually wired for 1 or the other. Ryan's a little bit of a unique, exception there because he he can wear either hat, but one person kind of faces outwards towards the market. One person faces inwards towards the organization, and you kind of think about them being tied back to back. When those pairings work well, it is transformational to an organization.

But getting that to work is tough. And finding somebody, I would imagine as a visionary, finding somebody who sits in that role, sits in that number 2 role is really hard to do. So we're a little off topic of work sucks when the boss leaves. Maybe it's work sucks when the boss leaves and the integrator isn't ready to carry the weight of the organization.

And that's where you get frustrations. That's where you get short fuses. That's where you even get, like, little snappy remarks, which, you know, kinda seems like a morale beater, if you will, that'll bring down the morale of the team, which makes work suck.

And I can imagine

I found it's only, like, 12 ish messages back from September 11th. It is currently October 17th, and I said, here's the priority list. Is this list done? No. Then why are we asking why are we saying we don't know what to do?

[09:48] Ryan Hodges:Wasn't that long ago. That list is not done. It was tagged who needs to be doing what, what is the priority in each functional area, and here we go. We don't know how to we don't know how to so it's it's it for me, it's very frustrating because everybody goes, well, we don't know what to do. Bullshit.

Go go look in Slack. It's right there. Well, but but so for me Right. I'm pissed off as hell because it's like, I've explained this. I've shared it.

I've done that. What what sort of just me doing everybody's job is it gonna take to get the work done? But saying that doesn't build morale. It demorals morale. So as as almost as the as the visionary, you know, founder, owner, you know, etcetera, like, you're you're in a rock in a hard place.

And so, like, work sucks for me too. My vacation my vacation was half derailed. I mean, luckily, I've done this enough that I was able to put some rules in place and still have an enjoyable vacation, but I'm coming back to, you know, having to be the janitor and clean up on the backside. You know? And and I get the, you know, work life balance or work is hard.

It's like, well, how is this fair for me? Because guess what? Right. I still have to pay all you freaking people with all the crap. How is this fair?

I don't get to go on vacation, and I have to pay everybody's payroll for not

[11:12] Ryan Hodges:But then there's the, well, you should appreciate that we, you know, we worked hard. Great. You worked hard on wasting my money. Thank you. I appreciate it.

Here's a pat on the bat for wasting my money.

[11:29] Ryan Hodges:So I think it's I think, you know, I'm I'm I'm ranting here a little bit. But I think it's it's Yeah. If there was more work this this scenario makes work set for everybody. Yes. You know, I think too often there's the level of the you know, they say it's lonely at the top.

Right? Or they don't understand why is the CEO or the owner founder why are they just so focused on the results? Why are they focused on the revenue? Well, the money has to come from somewhere. Right?

Like, that creates and this is where I think it's the downward spiral, is everybody has a hand in solving this problem. And so I think the big thing is is when the boss is away, everybody should be going, okay. Remember how sucky that was last time? He's gone for a week into weeks. What roadblocks do we have that we should get addressed so that we don't have that again?

I think too often, and this is where the executive team and the managers and whatnot I mean, even if you're even if you're an employee and you're you have a middle manager that's in this place, all it all applies. If you know they're going to be away and you wait until they're away to ask questions, you're probably going to piss them off. Reactivity

[12:44] Ryan Hodges:friends in this situation. Yes. So it's it comes down to yes. The integrator's role is to beat that drum and to drive that consistency, but in the absence of an integrator, it's up to the rest of the team to think ahead. You know?

I I don't I don't I would never and maybe I don't know if I have exception to a rule or if I'm, you know, the the rule. I would never be pissed off if someone said, here's the things I think I or I'm gonna attempt while you're gone. Is this okay? Or here's some roadblocks I think I'm gonna run into. Can you pre authorize these decisions or these money, you know, these expenses or whatever.

If someone came up to me with that a week or two before I left out of town and I blessed it, I'd much rather have that than getting text messages at 8 o'clock in the morning while I'm trying to get to Disneyland going, here's this plan. Do you authorize the expense? Fuck. No.

[13:42] Ryan Hodges:hell are you doing? So House. We gotta make we gotta mark this, this one's not friendly for kids, apparently.

Yeah. We'll we'll put the parental advisory on it, before we push it out live. Okay. So when when the boss goes on vacation, work sucks for the boss. Work can suck for the employees and the managers.

You kinda already go into what do we do about it. For the senior leader, I think one of the things we've not hit on, but it's probably worth it, is you need to communicate to your people in advance that you're gonna be gone. Right? And I'm not saying you didn't do that. I'm just saying that I have worked in organizations that the boss just disappears for 4 days.

And you're like, hold on. You are gonna tell me that, like, I can't talk to you for the next more days. So you've gotta communicate that to your people in advance, or don't be surprised if they're not prepared. Oh, totally. If you don't if you don't tell your people you're going on vacation or you're gonna be away, I mean, you

Next week, more various business meetings, and I'm gonna be disconnected. That travel plan has been known for everybody. Right. So it's it's not it's not been it's not blindsided anybody. So I just wanna make sure it's not it's not just when you're going on vacation.

You know, there's a lot of executives or founders, owners, exec, etcetera. They fly around and meet with customers. You know, a lot of them are the leading sales guy or driving sales or partnership efforts. So it's not just when you go on vacation. It's when you're out of the day to day.

Yes. As just kind of a general rule of thumb, to make sure you're prepared for me not being available for that day, 5 days, whatever it is. So that's first action item for the senior leader is make sure you're communicating to your team in advance of your inaccessibility or unavailability. Second thing that the senior leader can do, tell your team you're gonna be out, when you're gonna be out. The other thing you need to do is how how do you prepare them for your departure?

Prepare them for being on on vacation

There's less you know, it's more about making sure they're in sync with each other and, you know, with the thought of power in decision making while you're away. So let's say if you got a more see if you got a more senior leadership team, they're executing, the day to day is running smooth, it's really what decision making potentials, decision tree, if you will. Like, don't call me like, if 3 of you agree and we're within, you know, $5,000 of budget or, you know, of this expense, like, make their decision and go. If you're above that, call me. Right.

So a lot of times where I've seen is is running the day to day is not an issue. It's when there's a an oh, shit moment, and we need to we need to cross collaborate. And then it's well, normally, the tie breaker goes to the guy that's out. So how do we still maintain a decision and move forward? So that's one for more experience.

On the junior team, I think it's I think this gets into, like, thinking ahead. Like, what's your project are you working on? Do you have all the components lined out? Do you know what you need to get done? Do you know what done looks like?

Do you understand the objective? Okay. What roadblocks do you foresee? But I think I'm gonna I'm gonna challenge this a little bit because this is actually one of the problems that that I ran into is there's a level of challenging questions like that. But I think with a junior team member, they're trying to prove themselves.

Right? They're trying to show their worth. They're trying to be a super doer. They're trying to, you know, show that they've got what it takes and and progress their career, etcetera. The problem is in these scenarios, and this is literally what happened with with one of our individuals, is they had the answer before they thought about it.

It was you have what is the priority for this, and do you have the roadblocks? Already have it. What are those? No. No.

No. You're not thinking high enough. And so I think there's a level of no in these scenarios. You have to actually stop and think about it. It may take you 48 hours.

Think about it. List it. It's almost like the elevate and delegate, exercise. Mhmm. What are what what are my or or SWOT analysis.

Almost run a SWOT analysis. Sleep on it for 24 hours, and then go through it again. Because if you think you know the objective and the person's gonna leave and you have an immediate answer for it, I'm gonna bet you're probably 20 to 40% off track. Mhmm. Because you're trying to prove you have the information.

But in this particular case, I mean, I think even before I left, 2 weeks ago, I challenged, have you thought through this? Yes. Show me. That's not good enough. Think through it again.

But then it came in then it became, well, why are you challenging me? Do you not trust me to get it done? It's like, no. It's not that I don't trust you. You're not thinking far enough ahead for the duration of my leave.

You're thinking one week ahead. I need you to think 2 to 3 weeks ahead. Because think if I'm gone a week, that doesn't I mean, really, you need to be thinking 3 weeks ahead because you got the week you're gone. You got a week of catch up Right. And still decisions that need to be made.

Good. So I would say, I I would almost go if you're gonna be gone for 1 week, you need to give 2 weeks notice, and they need to be thinking 6 weeks ahead. 2 weeks 2 weeks prior, the week you're going, and the 3 that follow it. And that's the problem. People only think, oh, you're gone a week.

I only think of the next week. Right? It's 2 we're 10 yeah.

And so I've seen that particularly early on in in startups. It's harder for a founder to step away from a startup because there just isn't any organizational muscle memory there. Whereas with larger organizations, it you know, we've done this for so many years that it it's not really gonna change that much whether or not he's here or not.

Mhmm. If you go into this, like, you manage your day to day task list, you're going to miss the mark by, like, a lot. Right? Yeah. Versus if you cut if you step out of routine process and use adaptive learning and think out like, I'd use a phrase, think outside the box, novel, then then that that's the level of thinking.

It goes, again, goes back. Routine process is thinking the next week ahead versus I just told you if you're gone if the boss is gone for 1 week, you need to be thinking about 6. Well, if your routine process is to think 1 week ahead, are you going to think are you gonna you're gonna miss it. You're gonna miss it by 5 weeks. And then what happens to the performance of the business?

And I'll tell you the the other side of this is you get back and you're frustrated with it. Here it is 2 weeks later. Well, for me, it's 2 days, but I can tell you I can tell you what this is gonna look like in 2 weeks. And 2 weeks later, everybody's frustrated. You're trying to clean up the mess.

You're trying to pick up all the pieces and keep moving again. And because you're thinking in a 1 week cycle, you go, well, what in this past week was so wrong that we went off the rails? I just looked at my message here. This started September 11th. The priority list was set September 11th, and you just said that was what?

5 weeks ago? Actually, we're past the 30 day mark. So we're we're past 30 days. Mhmm. So, clearly, we did not think 6 weeks in advance when it was set that far ahead.

Yeah. Yep. So you know? Trying to get out of rent.

Yippee. And then I get a little older, a little more mature. Like, I need to be planning a week, like, my whole week out. And I'm listening to you, and I'm like, Ryan's planning months, like, maybe quarters at a time. And I think that's a really helpful thing for people to understand is is that, look, as a as a young employee, yeah, you should be planning your day.

That's definitely the right thing to be doing. But understand that your boss's job is to plan the week or maybe 2 weeks, and their boss's job is to be thinking monthly. And in order for for any of us to begin to move up and take on more responsibilities, get that promotion, you've gotta be thinking out over a longer time horizon.

Like, the king's off in the crusades, you know, conquering, expanding the empire, and doing all the goodwill and whatnot. And, you know, the the local, you know, sheriff and the local guy are just taking advantage, and then, of course, you got the hero Robin Hood. But what I like at the end of the movie is the king comes back, and he's like, what the hell? This is a shit show. He's like, what the hell have you people been doing?

He's like, luckily, this Robin Hood guy had some sense to try to put this out and alright. Thank you for unsaved or thank you for making it right. Paraphrasing all this here. But Mhmm. That's like, that's that's what I can't stand, and it's frustrating is, like you just said, you know, I think quarters you know, some cases, you know, half a year, year, year and a half in advance.

And, like, this particular set of trips that I've been on is, like I said, here are the things I set out to accomplish, and I'm gonna come back. I'm gonna go conquer territory, and I need the team to be ready to support this new territory I'm gonna go conquer. Mhmm. Here I come back from my crusades. We've won, and I'm like, you guys aren't ready for shit.

What what the hell to do while we've had this idea and we went left field and we thought this and we're trying to and what why? I just told you. I'm gonna go conquer over here, and you need to be prepared to support. And you come back to like, that's the problem is, you know, the these series of trips, they were planned almost 6 months in advance.

[27:12] Ryan Hodges:Yep. And so for me, coming back and seeing that the team not only didn't make any progress, they just rode the boat in a circle That's right. In the park. Like, we didn't even get out to open seas. We, like, got 10 feet from the pier and just rode in circles.

And then we want the pat on the back that we rode really hard. Great job. And here I'm like, where's the Armada ready to set sail? Like, we got we conquered. Anyways, I think that goes into, like, that you have to keep that mindset.

Like, if if you know they're going out to on conquest, then you've got to go, what are you conquesting? What are you going after? What what what do we need to come prepared with? What what does success look like? What are where we need to be?

And I think too often, we lose sight of of that component. You know, I'm definitely showing off my pissed darkness here. He says the boss is pissed. Oh, hell yeah. I'm pissed.

Team is frustrated. I'm pretty sure I can read it. I can read the line between the lines and slacks. It says putting feelings aside, how do we get back on target? It goes back to what's the vision.

What are we trying to do here? Mhmm. At the end of the day, I think if if everybody goes look back like, that's the whole red line, green light. Right? We had a perceived high value.

We thought our plans and these ideas we came up when the boss was away were gonna be good ideas. The problem was is we didn't reality check the vision. And the only way to get back on track is not come up with new ideas. It's to go back to what is the vision. What are we trying to achieve?

And how do we how do we you know, you gotta set feelings aside. Everybody screwed up. Whether the boss didn't communicate clearly, which I know I'm I'm sure there's some components of. Whether my assistant didn't communicate something that she should have, I'm sure she's guilty of that. Whether the team misunderstood and didn't ask clarifying questions, I'm sure they're guilty of that.

At the end of the day, everybody's guilty. So we have to put all of that aside and go, alright. We fucked up. But what's the vision here? What are we trying to do, and how do we get back on track?

So results, like, where are the sales? And it's like, well, if you wanted to have 10 customers, you probably needed to have a 100 demos, which means you probably need to have a 1,000, you know, phone calls. Did you make a 1,000 phone calls? No. Well, then why do you expect that you've got 10 you would have 10 paying customers right now?

Like, you didn't do the journey, so don't expect the results.

Okay. So you didn't make the phone calls as planned, and you came up with an idea that you have no results on. Right.

[30:34] Ryan Hodges:Well, yeah. Well, then you go back down to I think that's that's a component of it there. Like, don't change the vision. The vision is not clear. Right.

Like, that that and that goes into that prep work ahead of time. If the vision is not clear, you've gotta get understanding on the vision. The journey shouldn't change. The problem is when the when you're trying to get to the result at the expense of the journey or you're just trying to get to a result and you're creating vision along the way. And I think that's a lot of what happened while I was gone this last week is the the vision and

Break force results any way possible. And, and, yeah, it it creates a mess.

Like, let's let's unwind this. We didn't hit the result. We all this is retrospective. We we didn't hit any results. We screwed up.

So then we go to the culture and go, do we really have a bad culture? No. I'm sure if you look at everybody's well intentions, etcetera, then let's go back up to the vision. What's the vision we need to achieve and what's the journey to get to it to get to the results? Almost like a sideways hour hourglass.

And I think, again, I think people go too much vision results. Well, we didn't hit that. So let's go back to the vision, then go journey. I agree. But from a retrospective standpoint, what happens is too often now this is this is dangerous.

Too often, we'll go culture and we'll start finger pointing who didn't get the result. So first and foremost, you have to go, we missed it. It is what it is. Do we have the right culture and people on the bus? Okay.

We've got good people. We're good. Let's go back up to the vision. Alright. What's our vision?

What are we trying to achieve? What was our plan? How do we agree to do it, the journey? Let's apply our good culture people to deliver the result. Yeah.

And I think that that applies doesn't matter where in the organization you are. Everybody I mean, even the the frontline or the the, you know, individual employee, individual contributor is is you everybody's gotta look in the mirror and go, how did I contribute to this failure? And what can I do to to fix it?

It's not a pleasant conversation to have with yourself, certainly not a pleasant conversation to have with your boss. But if we don't have those conversations, we can't get better and work just continues to suck more and more. So, I like the way you talked about that as retrospective. We didn't hit the goal. Do we have the right people?

Are they committed? Are they doing the right things? Do we have the right vision? Do we have the right processes in place? And at some point, the answer is going to be no.

Find out where that answer is no and go fix it. Yep. And that's how I would make work not suck when the boss is away.