Episode 49: 5 Reasons Delegation Is So Hard & How It’s Holding You Back
Feeling overwhelmed, overworked, and underutilized? Maybe all that work you are doing isn't meant for you?
Effective delegation is really hard for ambitious and driven people to get the hang of. But not empowering your team to meet their potential is also keeping you stuck in the weeds and without that promotion you deserve.
In this episode, I share the top reasons leaders struggle with delegation and what message it sends to their boss.
Full Transcript:
Welcome back to the Upgraded Leader Podcast, where we talk about all things managing up, building relationships, your personal brand, setting goals, setting boundaries effectively delegating to our team so we can both develop them and also not run around like a chicken with our heads cut off, and of course succeeding in our careers on our terms.
I'm your host Nicole Case, and today we are talking about one of the most important skills that an upgraded leader can have, which is effective delegation. So. I think this is one of the biggest things that holds leaders back from getting up to that next level because they are just so bogged down in the weeds.
They don't have the energy. You don't have the energy and the bandwidth to really do more of those strategic and value add activities. And again, this is just a theme with a lot of the clients that I have, and most recently had this [00:01:00] client who she. Was just so overwhelmed working crazy hours, but wanted to get to VP and she was senior director.
Been a senior director for several years, was leading her department. And she's like, I want that VP title. Like I, I want to be recognized and, and be promoted to that VP title. And I was like, well, what's keeping you, what's holding you back? Like, what do you think is, is going on here that, that you haven't been promoted to this already?
And she's like, wow. I just think it's just the workload, you know, the workload. It's just, I'm just too busy, you know, doing all the things. Um, you know, and it's keeping me from being able to do that strategic thinking, do that, you know, visioning and all of that stuff. You know, it's just, it's just too much work and Sure, yes, workload definitely can be part of it, but when we started to talk about what exactly it was that she was spending a lot of her time on.
She was working on things that she really shouldn't be working on at this point [00:02:00] or, or things that she didn't need to, or it was busy work and frankly, she was running around like a chicken with her head cut off. And in fact, in our very first session, I could just see the frantic, chaotic energy just in this tornado swirl all around her.
So much so that I had this pause to do some breathing exercises to help calm and clear and clear the mind. I can tell you that in my decade as an HR leader, I would be in these meetings where we're discussing who's getting the promotion, who's getting the raise, who's getting the expanded scope because of a reorg.
And so let me tell you what this whole thing looks to a senior leader. So if you are someone who, again, maybe you can relate to my client, you're doing a lot of work. You're feeling overwhelmed, you're feeling frantic. This is what this looks like to your senior leadership right now. You look like you don't know how to make decisions on what your top priorities are for yourself and for your team.
Maybe you've taken on too [00:03:00] much. Maybe you didn't feel like you could say no to certain things. You're just, you don't know how to make decisions and you don't know how to prioritize those needle movers, particularly for the things that you yourself should be working on versus what your team should be working on.
It also looks like you don't trust your team to handle the work that they were hired to do. Like again, my client, like she's been working over these last 18 months to like hire a team. And again, then that takes time and it takes time to get people onboarded and get people up and running. But it looks like you don't trust your team when you're not delegating effectively.
It looks like you don't trust them to handle what they were hired to do, and if that's accurate, like if you have some low performers on your team or people that are maybe, maybe struggling just aren't getting it, and you're like, yeah, I can't trust them to give them this stuff because it's so important.
What that's also showing your senior leadership is that you don't know how to effectively manage someone who is struggling or not performing, that you're just kind of ignoring a performance issue. And believe [00:04:00] me, that does not look good for you. That's not a good look for you as a, as a, as a, as a future senior leader.
And finally what this looks like to senior leaders, when you're just running around frantic, doing a bunch of stuff, doing all the things, being overwhelmed, being pulled in a million different directions, you look like a freaking amateur, which is a shame because you're not an amateur. You are a pro, you know what you're doing.
But for whatever reason that we'll get into here in a minute. Your inability or your refusal to step back and figure out what you should be working on, how you need to be delegating more effectively is keeping you from getting called up to the big leads. Because again, when leaders are sitting around talking about opportunities for people, they're saying, well, we can't give that person more stuff.
They're already too overwhelmed. No one is gonna give you more responsibility if it appears that you don't know how to make decisions. You don't know what your top priorities are, and that you don't trust the team that you've built to handle the work that you were hired to do. No one's promoting you to that next level if this is, if this is what you're giving [00:05:00] off, right?
So. Because you are running around, like you're in the space of chaos and franticness. That's not what you were hired to do either. That's not what they didn't, you know, you didn't get hired to run around like a chicken with your head cut off. So again, um, my client and I, we had been working on this for the last several months and.
You know, working on, again, setting her priorities, you know, figuring out what she can delegate, how she, how can she delegate? And again, it doesn't happen overnight. So we were, we've been working on that little by little. And in her last meeting with her boss, you know, she was ready. Like, I'm ready to go in and I'm ready to like, have this conversation about next level.
And, um, in this last meeting that she had with her boss just a few weeks ago, he said, yeah, like, totally see the progress that you've made. You've really built this team up. You know, and they're just on their way to finalizing. You know, the final details for her VP promotion, which is amazing. And I know that she says that she just feels more calm and more in control and feels like she can just, she can take on [00:06:00] more and it, it's freeing her up to really do the work that she's supposed to be doing as a strategic senior leader.
So. Why is it so hard for us to delegate? Why is this frankly one of the number one reasons why people come to me? They might not say, Nicole, I'm, I need some help with delegation. That's why I wanna hire you as my coach. That's not what they say to me. They come to me, they say they're, they're like, I am overwhelmed.
I don't know, you know, my up from down, because I'm just so torn in so many different directions. You know, I don't feel good. I am, you know, burnt out. You know, my life at home is suffering as a result of all of this. And when we dig down deep into it, this is one of the, the foundational issues is that we are not delegating effectively.
So why is this so hard? Why is this such a hard thing to do? So here are five reasons that I've come up with on why it's so difficult for leaders to delegate. First and foremost, you think that you don't have the time and I. Hear you, that delegation does take [00:07:00] time. It takes, it takes a lot of time upfront and a lot of times, you know, you might just be feeling like, well, you know, it's just faster and easier if I just do it myself.
And while that might be true in the short term to continue to have that, to have that um, perspective or to. Continue to perpetuate that over time, you're gonna find yourself with a bunch of those little things continuing to pile up and compound on themselves. And once again, you know, your, your top, you know, c-suite leaders are looking down at you thinking like, what the hell is she doing down there, working on that thing?
Even though, yeah, maybe it took you five seconds to do, like, that's not what they hired you to do. So once you do figure out who to, who to delegate to, who to pass this task off to. Again, it's gonna take some time to kind of get them up and running, especially if they're a new employee or if it's a new thing for them.
But once you are able to effectively do that, then that will free up the time, not even just the time, but the energy and the brain space to, [00:08:00] to really truly work on the things that are the most important and that is going to move the needle for the team. And I get it, you might be understaffed, you might not have all the team members that you need, and the work needs to get done by somebody, so it might as well be you.
And this is where your communication, your influence with your boss comes in. This is where the decision making is gonna come in, which is a whole other episode on decision making and priorities. Um, but this is where that skill is gonna come in, where you're like, listen, you know, we don't have enough staff to get all of this done.
We need to, we need, again, priorit, we need to prioritize. And there's gonna be maybe some difficult conversations or some, you know, uncomfortable conversations to be had to, you know, to really figure, figure this out in the interim. Number two. The other reason, another reason why it's so difficult for leaders to delegate is one, you just don't know how to do it effectively.
Like this is a skill, delegation is a skill that has some steps to it, right? Delegation is not just shooting off an email or an instant [00:09:00] message to be like, Hey, can you take care of this for me? Or, Hey, I am gonna assign this to you. Uh, you know, delegation requires a couple of steps. Um, you know, first you have to decide what it is that you're gonna delegate.
For a lot of my senior leaders, I I, my clients, I will give them a tool that talks about like what it is that you need to delegate, what it is that you need to do, or what it is that you need to delete altogether. And so once you kind of figure that out and figure out what it is that you are going to delegate, what makes sense to delegate, you have to pick the right person to do that.
Now, I get it, maybe you're a team of two, or maybe it's not, you know, you don't have a whole lot of people to choose from, but you still need to pick the right person to delegate that thing to.
And then once you pick the right person to do this task or do this thing, whatever it is that you're delegating, you have to set really clear expectations. And this is a big one again, that I think that we gloss over or we forget about. Because to us, a lot of times these tasks are things that you can do, you know, with your hand tied behind your back.
You know, they're super simple for you. [00:10:00] You've done 'em for years, whatever. And you just kind of toss it off in the ether to the person that you want, want them, want to do it, and you haven't set clear expectations about what good looks like if there are very, very specific parameters that you need them to work within.
You know, if we're not setting clear expectations, you might not be getting back what it is, what it is that you're looking for. So we need to take the time to set those clear expectations and check in with them to say, Hey, how's it going? Let you know. Maybe set some milestones. But if we're not doing that, that's when you're gonna gonna get frustrated and you're going to, you're gonna say, holy cow, I should have done this myself.
Because you're not getting back exactly what it is that you were looking for. So again, it's really important to set those really clear expectations and then continue to check in and give feedback along the way. And finally, we have to also give them the why. So when you're delegating something to someone.
You have to let them know why you're giving it to them. Why, what's the, what's the importance [00:11:00] or the value of this particular task and of them doing it. You're not just dumping, you're not just dumping on them or whatever. You know, there is a reason why you're, there's a strategic reason why you're giving this person this particular task, and it also might be really, really great for their development.
And so that's something that you wanna make sure that you're highlighting as well, that, Hey, you know, this particular task are you representing in this meeting. You know, is really great for your visibility, it's great for your development, so I wanna make sure that you're getting opportunities to do that.
So sometimes just taking that extra, you know, 15 seconds to explain that can really go a long way for one building. You know, that trust and that rapport with your employee to see that you care about their development and you're giving them. Tasks to support that, and it's also helping them understand kind of the bigger picture of why this particular thing needs to get done.
The third reason why I see leaders not wanting to delegate is a fear of losing control. A lot of us, I'm sure on the listening to this podcast, have very, very high [00:12:00] expectations and maybe a touch. Or two of perfectionism. And sometimes we can think that only we can do this thing, only we can do this thing.
And that is probably not true. Now, as part of your, again, as part of your decision making and prioritizing, you know, there is a question of what is, what is the only, what's the thing that only I can do? And you retain those types of things. But I can promise you that not everything is a task that only you can do and that only you can do well.
So a lot of times what I'll say to leaders when they're delegating and they're setting expectations about what things need to look like, my question to them, and my question now to you is, is this a requirement or is this a preference? So if you're giving somebody a particular task. Are all of these parameters that you're giving are those requirements or are those preferences?
So we wanna make sure we ha where, where and when we can. We're giving our employees the space to be able to do their work in the way that they wanna do their [00:13:00] work. Right. So just because you complete a certain task or you send a particular email or write a particular communication in a certain way, we have to.
Where again, where we can allow our employees to do the same thing. So again, if you want to really think back on this, are these parameters that you're giving of requirement or are they a preference? And I can promise you that the more times you recognize that, hey, this is a preference and not a requirement, and you can kind of let that go again, the less pressure you're gonna have on yourself, the less pressure the employee's gonna have on themselves to create something that might not feel as natural for them.
Another part to losing control is that you're confusing the doing with the leading just because now you're a senior leader, you know, you're, you're, um, leading your teams. You're now no longer responsible for the doing. You're not responsible for the doing, so you're confusing the doing with the leading, and [00:14:00] that is not what you're being paid to do anymore.
And I know that you might have felt really comfortable with these tasks that you've previously maybe wrapped up your value in doing these tasks really, really well in the past. So it can feel really uncomfortable handing them off to someone else. Um, I had a, a client last year. She was, was a senior vice president at a really large pharmaceutical company, and she all of a sudden did not have her own client portfolio.
She had in the past, you know, had, you know, maybe seven or eight of her own clients that, you know, a portfolio of, of projects that she was leading and she was running and now she's leading the entire department. So she doesn't have as many client meetings. I. This made her really, really uncomfortable because she had some empty space on her calendar now, and previously she was putting her value in, you know, how full her calendar seemed.
And I think this was probably an unconscious thing, right? Like nobody's looking at their calendar saying like, you know, whenever you're [00:15:00] in 10 meetings every single day back to back, and you're like, oh good, you know, goodness, you know, please more meetings so I can feel more important. Nobody's probably thinking that.
But unconsciously, she's like, oh man, you know, now all of a sudden I'm not needed anymore. You know, I'm not being invited. I don't have as many meetings. And so what we had to work on was, again, articulating what it is that she was being paid to do now, which was the strategic leadership, the vision. She, you know, escalations, you know, she's not, she doesn't need to be in every, in every customer meeting, but she's there for those escalations and.
Supporting ongoing business development. So once we were finally able to kind of really, truly hone in on what were those top things again, that she needed to retain herself because these are the things that she is responsible for, then she could better plan her day. She could, um, you know, schedule specific time to get out and talk and, and to talk to customers in a more, in more of a proactive way versus a reactive way.
So [00:16:00] that just really shifted her whole mindset around this. The third reason why a lot of leaders struggle to delegate effectively is because they're afraid of what it's gonna look like to others. And I can't tell you how often I hear this on a lot of different topics, like, well, I don't wanna look stupid if I speak up in this meeting.
You know, I don't wanna, I don't want other people to think that I'm bragging. Like there's this whole thing about people so worried about what everybody else thinks about them. That, and by the way, it doesn't matter where you're at in, in the organization or, or how long you've been in the workplace, like.
These insecurities and concerns continue, you know, continue. But I hear a lot from leaders that like, oh, I'm a servant leader. I don't wanna look like I'm dumping on my team. Again, you're not dumping on your team. You know, you're, you're not like tossing out. I. Tasks because you know, they're now like so beneath you.
It's not, it's not that. It's just that it's your job to direct your team on, on what they need to be working on. Plus, your team probably [00:17:00] wants this stuff. I have a client we just talked last week, and her boss keeps keeping things to himself and like keeping tasks or meetings or whatever to himself that clearly should go to my client.
And it's frustrating for her because she's like, why am I even here? Like, what value am I even bringing if my boss just keeps all the work and she really started down the shit spiral of my boss doesn't trust me, they don't think I'm capable. You know, all of these things when really her boss just doesn't know how to effectively delegate.
I. That's really what, what it is. The other part to this is sometimes you're trying to look like a hero, you know, or trying or, or maybe you have this belief that the more that you work, the more tasks that you do. You know that the hard work, you know, this whole idea that, you know, again, the more work that I do.
The better that you're gonna look. And this is giving some Harry Potter martyr vibes. Like let your friends help you, let your friend team help you. And by the way, Harry Potter could not have done all of that [00:18:00] on his own. He would've literally died if Hermione wasn't there. So let your team help you. That is literally why they exist.
Your team is there to help you get this job done, get this work done. It's also giving some vibes around like, I have to look busy or else I'm not worthy of my role. Or you know, or you know, again, back to like my client who's like, ah, I've wrapped up all my entire existence and my entire worth into how many meetings I have on my calendar, and now I have less.
And that's weird. So this is just your ego talking, right? We all have got this, we've all, you know, our ego kind of crops up and tries to take over. And this is also just kind of your insecurities just on full display here. And, and again, I'm not trying to call anybody out or anything like that, but it, this is like totally normal.
So it's. And what I'm saying here is that when we can notice it, then we can start addressing it, right? If we continue to keep these feelings buried underneath, then we're never gonna be able to truly address them. So just [00:19:00] to remember that it's not how hard you work, it's not how much you work. It is making sure that you are working on the right things because that's what an upgraded leader does.
And finally, one of the reasons why it's really challenging for leaders to delegate effectively is that maybe you like the thing, maybe you like it the higher, but the higher up that you go in your career, you get further away from the thing. Unfortunately, that's what ends up being the trade off. You're not really able to do the thing anymore, and.
This can be a really, really hard transition to make. 'cause you were probably recognized and praised a lot earlier in your career for this thing, the skill that you have. Maybe you got a lot of promotions as a result of that previously, but there comes a time when you become, um, a more senior leader that.
Again, this is not what you're now being paid to do. You are now being paid to help and [00:20:00] enable others to do that thing really, really well. So if you were, for example, a rockstar software developer and now you're a senior director, leading the team, leading the whole, the whole department of this particular product line, you're not coding anymore, right?
You're not developing anymore. And I get like wanting to keep your skills sharp. And either you're doing that through a passion project or you're doing that. At work on something that is very, very narrowly focused so you don't get bogged down. But again, this is just not your role anymore to do. I, I had a, a client last summer who actually shifted out of, um, full-time corporate work and decided to start her own consulting.
Business. And she was a UX designer and she was, you know, a, a, a senior director, you know, leading UX design teams for many years. And when we were talking about packaging and pricing her, her new consulting work, I was like, there is a [00:21:00] price for the senior director vision. Planning sort of work. And then there's a different price for the UX design work.
Those are two different pricings, two different packaging because it just, it requires different skills and a different level of experience. Look, she has both experiences and she is choosing to continue to, to tap into both of those things. But again, what I was sharing with her, I was like, you, you're gonna be charging more for that more strategic vision setting sort of consulting versus an hourly rate for doing the actual UX design tasks.
Those are two different things, and we have to remember that when we are in our. In our full-time corporate roles that again, there's a difference between being that senior leader, leading the department versus the person doing the thing. And I get it, it can kind of be sad, right? Like, I mean, you're excited that, you know, you've [00:22:00] continued to move up and, and to grow in your career in this different, in new way.
But it can be kind of sad. And we just have to remember that we have to let go of what we were before in order to step into this next level leader. So we have to remember what we're being paid. To do. So if you're like, Nicole, get it, hear you. But what are some things that I can start kind of dipping my toe into to doing some, um, effective delegation?
What are just some things that I can delegate kind of right off the bat that are, that might be easy for me to transition to? So here are a couple of things, and now again, there could be some nuances depending on how big your team is, where you're at in the organization. But here are just a couple of things that.
Um, you can kind of get the wheels going a little bit. First and foremost, I think everybody needs to take a look at their calendar and see what meetings they're in and be like, I don't need to be in this one. I very easily I can have a team member represent in this meeting and then have them just debrief me later on.
Um, so this is especially easy if you ha if you are going to meetings and you're seeing that you have other team members that ha like some PE people on your team who have also been invited to this and. That's an easy one to be like, uh, if I've, if I see another team member in this, in this meeting, that is a signal to me that I do not need to be here.
And then I'm gonna let you know the person on my team represent us in here. And again, they're probably gonna feel really good about that. That employee's gonna be like, oh yeah, you know, I'm the one representing, representing the team that's actually gonna feel really good for them. That's a visibility opportunity for them that they are really, really gonna appreciate.
Another kind of thought around meetings is just sometimes the organization of maybe some internal project meetings or some internal team meetings. You don't need to be the one that's trying to like find the time on the calendar book the conference room, if you're in person, you know, set up all the things.
That's something you can very easily delegate out to someone and say, Hey, listen, I need you to own this meeting. Can you like get this meeting series together? I need you to own this. And then. Maybe they lead it, who knows, that might be the right thing. Or you know, you, maybe you still retain, um, the leading of the meeting.
Now, here's another thing you, you might be able to delegate easily, is if you are leading the meeting, you do not need to be taking the meeting notes. Somebody else can be doing that. Either you rotate that throughout the, the other team members, or maybe we just say, Hey, we're all adults here and we can all take our own meeting notes.
You know, we might not need a whole thing. Or maybe you have an AI tool. Um, that can take the meeting minutes for you. The action items for you, I actually just implemented this with my clients. Um, I have a new tool that I, that I've been using called read.io that just latches onto your, zoom to your teams, whatever, and it records for you, records the meeting for you, and then the AI tool goes back through and like creates chapters of highlights.
That you can just click right into and it creates, like, here are the questions that were asked, here were the action items that were collected. It's really, really cool. So, um, so again, I've been, I'm now using that with my own clients. Um, I can see that being super useful in corporate if you have, um, if you have some meetings that require something like that.
Another thing that can be really easily delegated is data gathering and research. So I can tell you that Taylor Swift was probably not researching possible design firms to design her stage for her Aris tour. Uh, somebody else clearly did that. I mean, I'm sure she shared her vision, I'm sure. Um, you know, she sat down with her team and said, this is the vibes that I'm going for.
This is the experience that I want my audience to walk away from. Um, and then somebody on her team went off and did that research, like, okay, who's the right design firm? You know, and brought and, and made that decision, brought them in. They, and they probably designed a couple of renderings and, and perhaps she had a final approval on in that stage, but there would've been a lot of work that needed to be done in between there.
And I can tell you that she personally did not do that herself. And there are lots of pieces of data out there that I'm sure you're probably needing to gather. So like, um, I had, uh, so like my, my client example, um, who's trying to get to VP just the other week, she was at sales kickoff and one of, you know, one, it's one time of year that all the senior leaders are coming together and they're um, and they're presenting to each other kind of on the state of the business, kind of an annual business re big annual business review.
And I told her. Like as we were, we were working on her presentation together and you know, kind of struck like, how do we wanna structure this? What's the most important information? And so her and I worked on that part. What was the most important information that she needed to share with that particular audience?
What was the asks, you know, what was it that she needed from them? All of those things. That's the strategic part that she needed to do as the leader. Then I said, and then instead of you then trying to like spend hours digging through all of these spreadsheets or all of these tools to pull out whatever pieces of data are are necessary, delegate that out to your team because one, again, they're probably gonna be able to do it way faster than you.
And again, your value here is recognizing the right data to track and then translating that data into a story for. You know, the other leaders, the other decision makers to either get behind your initiative or for them to make additional other company-wide and department decisions. So get your team to help you gather, gather data, and you know, again, especially for you to say, Hey, you own this area of the department, or you own this area of the business.
You're responsible for your, for your metrics, and pulling that, and we're sharing those with me on, on whatever cadence or whatever regular basis that. You decide. So again, data gathering and research is a really, really great task to, um, to, to, to delegate out to your team. And the last thing that you might consider delegating out is drafting communications and presentations.
Maybe again, the first draft. So this might, might not make sense for everyone, but I can tell you that when I was in HR earlier in my career, it was not my VP of HR who is crafting. Department-wide communications about the annual performance review process. I would create the draft. Other people would take a look at it, would do some editing, and then it would finally roll up to her, like almost like the final, final, and then she would do a final review and then she would send it out.
Now again, this was an annual process that didn't change a whole lot from year to year. Now, if this was something completely big, completely different or new, or just a huge change, maybe she probably would've had a bigger hand in the communication, but it, it didn't make sense for her to spend a bunch of time.
Drafting a communication for a process that was annualized. And so it made sense for someone like me to start, start the draft and um, roll it up to her. So maybe you, maybe you create a template. Of the overall of like maybe the presentation that needs to go out every month to someone, or maybe you say, Hey, can you craft a, a, a communication?
Here are the five things that need to be included. Can you get it started on it? And I know just even for me, just in general, that. Writing emails and writing communications can take a long time for me, just personally, so having somebody get started on something so I don't have to start from scratch with a blank cursor is, it can be really, really helpful.
So. Maybe there's some other tasks out there that are similar to that, that like, you know what, it would just be really helpful if somebody on the team could like get it going and then I can finish it, take it over the finish line, that kind of thing. So those are some of the reasons why it can be really, really difficult for us.
To delegate as leaders. I get it. I hear you. I see you. It's something, again, I hear so much with my clients and then hopefully there that you found a couple of things or started thinking about a few things that you can start delegating that you're like, yeah, you know what? I really should start doing that.
I know I've been holding onto it for too long, so hopefully. You are feeling brave, you're feeling more confident that you can get out there and start more effectively delegating to free yourself up from the chaos and the overwhelm so you can be focused on the right things that you need to be so that you're able to elevate yourself and elevate your team in the process.
So [00:23:00] if this was helpful for you, if you're like, gosh Nicole, you were speaking right to me, I could use some one-on-One help with this, and just kind of overall supporting your desire to, to really get to that next level in your career. I still have some openings on, I. My client calendar for some private one-on-one coaching clients.
So reach out to me either through email at nicole@theupgradedleader.com or find me over in the dms over on LinkedIn and send me a note and we can talk more about what that could look like. So thank you so much for, for hanging out here with me today, and until next time, remember, your career deserves an upgrade.
