Q&A: How to Delegate Without Guilt and Still Get Promoted

A Chief of Staff named Samir asks for advice about being overloaded at a startup, struggling to delegate, and never taking real breaks. Emily Sander suggests Samir update his boss on his workload, start delegating in small steps, and actually schedule and enjoy a vacation - sharing her own tips for disconnecting, including going snuba diving and ignoring email except for real emergencies. The episode highlights the importance of building a team that can function without you.

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Who Am I?
If we haven’t met before - Hi👋 I’m Emily, Chief of Staff turned Executive Leadership Coach. After a thrilling ride up the corporate ladder, I’m focusing on what I love - working with people to realize their professional and personal goals. Through my videos here on this channel, books, podcast guest spots, and newsletter, I share new ideas and practical and tactical tools to help you be more productive and build the career and life you want.
 
Time Stamps:
00:25 Listener Question: Overwhelmed at Work
01:19 Communicating with Your Boss
02:30 The Art of Delegation
03:42 Learning from Your Role Model
04:29 Preparing for Promotion
05:19 The Importance of Taking a Break
07:38 Tips for a Successful Vacation
11:34 Final Thoughts and Recommendations

Transcript

emily-sander_1_12-05-2025_091802: 0:25

All right, listener question time. Samir asks Samir from the UAE, which is very cool, says, Hey Emily. I'm Samir. I'm a chief of staff at a startup and my boss is this super successful founder. I really look up to, like part of me hopes I can do something like that one day too. Very cool. Lately, I too become the person who does dot, dot, dot, everything. Okay, so lately I've, I've also become the person who does dot, dot, dot, everything. More teams, more project. It all keeps just coming to me. I know I should, in quotes, be handing stuff off. Yes. Um, but I'm really not doing it. Hmm. Okay. I also don't feel like I can tell my boss about anything about it, and I don't even know what he actually sees of how I work. I haven't taken a real break in a long time and it's just getting a lot. Not sure what to do next. Any thoughts? Okay, Samir, thank you for this question. There's a lot of good stuff to talk about in here. So the first thing I would say is it was interesting that, I don't feel like I can tell my boss. About it. So I would, I would tell your boss what you're doing, not like a blow by blow, here's this 47 point list that I'm going to just recite to you. But it is just letting him know in a informative, helpful, relevant way of what types of things you're working on. Sometimes I have done this where I forget what I have given someone. I forget what my team members, I've asked of them. And so when I say, can you please do this thing? And they're like, uh, yes. Um, do you want me to do the thing you just said or the thing you said a month ago? And I'm like, oh, oh yeah. Or like the five other things that I've said over the course of time and I just forget. And it's not like malicious, it's not trying to overload them. It's just, I, I have all these things going on and I just happen to forget, Something similar could be happening with your boss, where if you keep him a little bit more in tuned and dialed into what you're doing, He might distribute that workload a little bit more. If he doesn't. That's another conversation around what's a reasonable workload? Okay. The next thing is, um, I know I should be handing stuff off, but I'm not really doing it. Alright, so Samir, delegate, baby, delegate Away. Do it. You'll feel great. They'll feel great. It'll all be great. one thing I wanna remind you of is delegation is not. Binary. It's not on off all or nothing. There's levels and gradients and gray areas of this thing. So it might be, for you, it might be more comfortable to delegate a little bit or delegate this one step or delegate this small project. To start with, I would ramp yourself up pretty steadily though. Um, in some cases it might be helpful to delegate in. Baby steps or bite-sized chunks for your team if it's brand new. So that could be an effective way to go, but I would get yourself started with something, start something this week, and then build on that over time and keep a pretty rapid clip, um, of how you're building that up. Or it doesn't have to be rapid, fast, per se. It just needs to be a deliberate and consistently steadily moving delegation process. You're delegating more and more and more. Okay. What else? What else? So the other thing that. Caught my attention. Oh yes. Was you mentioned you wanna be like your founder. So you look up to this person, wanna be like them. Ask yourself, does this person delegate or do they micromanage and take everything on? Some founders do and they microwave. Microwave. They microwave food and they also micromanage sometimes, sometimes at the same time. Um, they. We'll either be in the weeds or they'll be like, I don't even wanna touch that. I'm having a vision, I'm having an idea. Someone else take care of that. So you might kind of take a look at that model that he is presenting and say, what part of that works well? What part of that doesn't? What makes you look up to him? There might be some of these elements. All of that. So how is he, uh, thinking about workload or where is he spending his time and energy. also, also if you want to be like this founder and you want to, and or you wanna move up in the company that you're at in this startup as it grows, you have to have, team in place that can hold the work themselves. Even if your founder wanted to promote you, but they knew the work would fall down without you, it's hard to do that, right? So they're hard pressed to be like, yeah, Samir, come over here. Oh no, no. Like this stuff can't fall. You have to keep making sure this stuff happens. So part of putting yourself in position to be promoted and to become more and more like your founder. Is to create a backfill or a team that can stand on its own or, um, mentor and train and guide a successor in place. So having all that in place helps you level up, helps you get promoted in the long run. Let's see here. The, the last thing I'd say here is, uh, take a break. Literally go schedule a vacation Right now, just schedule, it doesn't have to be next week, but schedule it so there's a stake in the ground, and then you and your team can work toward, okay, hey, I'm gonna be out for a week in, you know, whatever, three months or six months or a month, or whatever you wanna do. But have that be a forcing function. Have that be something that everyone's driving to. Hey, like, Samir's gonna be out. Okay. Get people ready, get people handed off, get people the information they need. And then this is also a really good test for if you've set up your team well, a team should be able to run without you for a week. So, so Samir and everyone listening, your team should be able to run without you for a week if you've set it up so it falls down without you, you've not set it up correctly. I've seen a lot of people do this intentionally. Some, sometimes intentionally, sometimes subconsciously.'cause their ego won't allow them to do anything differently, and you're, you're just setting, setting that whole thing up for failure. If you do that, if you are the single point of failure and you're, and you wanna be in that position, so you're needed and you hoard information and you do all these things, um. I would, I would go a different direction with that because it's not good for you, it's not good for your team, it's not good for the company. I think a far stronger and more secure leader would say, let me set this up for success. Let me build the system. Let me build up my people so that. I can be a human being and take a break and everything is fine and people even get the opportunity to step up and maybe for that week get to be in different types of meetings and they're proxying for you or get to be in different types of projects. They're taking point on. All these things are good to give people reps on your team. So I would literally, I would go schedule a vacation. It can be. like a, I'm taking a plane and going to a different location. It can be, Hey, I'm taking a 90 minute drive and checking out a cool Airbnb on the coast of wherever, or like in a nice little area or just a different area than you're used to being in, um, something relaxing, something rejuvenating, And when you go on vacation, actually go on vacation. Actually be on vacation, So meaning don't just move yourself to a different physical, geographical location and then work all day long. That's not the point, actually go on vacation. And here's a few, few quick tips for, for doing this on vacation. So, um, when I go on vacation, I still check in on email once a day. Um, for anything critical or anything urgent, sometimes twice a day. But I try to be, I try to be. Careful and deliberate with that. When I was working in corporate, this was really tough for me. This was like, I, I, I didn't wanna go to the pool, I didn't wanna go to this excursion, I didn't wanna do all these things'cause like it's taking me away from the internet and from my computer, which is like not the point of being on vacation. But that's how I felt. These other things were getting in the way of me actually sitting down in the hotel and working all day long. so what I would do is I would say, I'm gonna take an hour. To check email and the things I'm looking for are things that are actually critical, that are actually exception cases where this is out of the ordinary run of the mill, turn the crank operation stuff I had set my teams up to do and I had to let them do that even though I was like, well, I see it and I'm, and I'm right here so I could do it really quickly. That's not the point. That's not the point. The filter is, are there any critical items? If it's truly urgent and important for you to do on vacation and other people can't handle that, like literally like something's burning down or you are the only person who has access level to this bank and something crazy has gone on with a customer that happened once. Those types of things are what I'm talking about. if it's, hey, like there's a client escalation. This is kind of urgent and important, but it's run of the mill escalation, and the teams can handle that, let that go. Critical, urgent and important exception cases was the filter. I would also set a timer for 30 minutes. So it's like Emily, you're halfway through, like halfway through and then for 50 minutes. So like, Hey Emily, you have 10 minutes left. Wrap this stuff up. Anything you wanna get done or have to get done in the next 10 minutes, start doing that now'cause you're about to be done on your time block. So I would do that, Now I'm actually pretty good. I will check it maybe once or twice a day, but if I'm done in 10 minutes, I'm done in 10 minutes. If there's nothing urgent or out of the ordinary or critical or whatever, I'm like, I'm done because. What I wanna be doing is actually spending time with the people I'm on vacation with or just taking some time to walk on a beach or go see something cool that's historical. All these things, that's the point of the vacation. Um, oh, the other thing I would do is if you're like, I, I'm bad at discipline. Even if I set a where I'm not gonna do it, go do something where you cannot be on your phone. So I used to go, I still go, um, suba diving with family and friends, not scuba diving'cause that's, scary and takes certification. Um, but Suba with n which means you have the little mouthpiece. And the tanks sit on, on the surface they're like on little floaty things on the surface of the water. And there's a big cord where you can go down, um, further than you can snorkeling and you can stay down there. And so it's like kind of in between snorkeling and scuba diving. It's scuba diving. And I do this in Hawaii with, last year I went with my nephew and we both went scuba diving and it was, um. Whale mating season. And so the whales under their surface were going crazy with their like whale calls and like mating calls and like all these different things and you could hear them and it was amazing. And it was so beautiful. And you can't be checking your emails when you're scuba diving. You can't be, you're not even thinking about that stuff'cause you're like, wow, I'm seeing amazing things in the ocean. I'm hearing sounds, I, I never hear on land or in the air. And that's just. Uh, a memory and experience with my nephew in that way. So you can, you can build these, build these events in or excursions in to your time away. Uh, you know, if you go to a hike where there's no cell reception and they're like, there's no point in checking your phone or even maybe, you know, bringing your computer, then, then you can structure things like that. So anyway, so Samir, I would just thank you for, for your message and thank you for being honest about this stuff. I think that's really awesome of you. I'm, I know that other people listening are going through the same or similar things as you. Uh, so thank you for sharing and, I would, I would tell your boss what you're up to. I would start delegating, even if it's small baby steps, I would start setting the team up and the structure up so you can lift out. And when you get promoted, and I would go on vacation, I would go scuba diving. That's the point of this whole episode really, is to go scuba diving and listen to whale mating calls. That's my recommendation to you, Samir, and to the listeners, go, go listen to whale calls and if you don't have access to an ocean, then you can watch Finding Nemo and the scene where Ellen DeGeneres as Dory makes the whale sounds because that's awesome and that will suffice as well. I'll catch you next week on leveraging leadership.