Podcast: How to Get Delegation Right, Part 1 of 3

And yet, It’s an enduring problem that strikes professionals at all levels. It’s wrapped up in all this stuff—fears, insecurities, your own sense of purpose—and it’s not always clear how to play it.

“The strategy is more about reading the room, understanding the strengths and weaknesses of your team, making sure you are clear about your own expectations, and then communicating that clearly to others,” says Brenda Ellington-Booth, a clinical professor of management and organizations and an executive coach.

In this three-part edition of Ask Insight, we talk to Ellington-Booth about how to do that. We hit on the basics, first.

(You can find episode 2 here and episode 3 here.)

Podcast Transcript

Laura PAVIN: Delegation is a crucial part of management and leadership. You know it, we know it. However ...

Brenda ELLINGTON-BOOTH: Quite frankly, it’s complicated.

PAVIN: That’s Brenda Ellington Booth. She’s an executive coach. And she says delegation is like a dance between two extremes. Extremes she sees all the time:

ELLINGTON-BOOTH: Sometimes leaders delegate more than they should just because their workload, or the demands on them, is really great. And they don’t have an option, and then things fall through the cracks, and that becomes problematic. And now it becomes more work than less work. And then people delegate not enough because of a lot of reasons. So people feel like, “Oh, well, they do it right. You know, my reputation is on the line as the manager.”

PAVIN: You’re listening to Ask Insight, where The Insightful Leader takes a burning question to a Kellogg professor for answers. I’m Laura Pavin.

Brenda Ellington Booth is a clinical professor of management and organizations here at Kellogg and she joined us for a three-part series all about delegation. In this three-parter, you’ll hear why it’s so hard to get right, how to trust your team to get the job done, especially when the stakes are high, and how to manage grief about handing over work you really love.

Today, we’ll kick it off with the basics of delegation: playing to your team’s strengths, providing clear expectations, and giving constructive feedback.

Jess Love, Insight’s editor in chief, spoke with Ellington-Booth for this series. She speaks next. Ellington Booth follows:

Jess LOVE: So when I think of some of the things that are the hardest to do, especially as a new manager, you’re new to actually overseeing a team, I think delegation is at the top of that list. And I am curious if that is also something that you have seen in your many years of experience working with executives. Sorry, I wanted to make you sound very experienced, not like 80.

ELLINGTON-BOOTH: They can’t see the eye roll. Okay. Um, delegation is hard, particularly for new managers, people that haven’t had people reporting to them. And I think it’s hard for a number of reasons, So. I think first and foremost is just, it’s new. It’s a new skill. People are used to being individual contributors and you know, there’s not necessarily a guidebook unless you have experienced a really good boss that taught you how to delegate well. And even then, if you had a good role model, you still have to find your own rhythm, your own voice. And circumstances could be different, you know?

So there’s a lot of different factors that go into delegation that makes it quite challenging. So, there’s a lot of kind of psychological inner chatter that goes on that makes people want to hold the reins tight. And then there’s also just your confidence and trust in the employees. And so, you don’t want to delegate to someone that’s brand new because they don’t know the ropes, and you don’t know how well someone is going to do until you actually see it.

And so, to some degree, there’s a little bit of trial and error. And a lot of times in the workplace, particularly in today’s workplace, where accuracy and speed is really important, you don’t want to have that person mess up.

LOVE: Yeah. It’s kind of like you want to reap all of the benefits of a highly experienced team that all trusts one another, but you don’t always allow enough kind of low-stakes opportunities to get that training in.

ELLINGTON-BOOTH: Yeah. Yeah. Yeah. And sometimes the work doesn’t lend itself to those low-stakes opportunities as well.

LOVE: Like what kind of situation do you have in mind?

ELLINGTON-BOOTH: Well if you’re talking to, like, an accountant, okay, that has like a year-end close, and they have, you know, a bunch of junior accountants reporting to them, and the stakes are always high in that situation because there’s deadlines and, um, accuracy is really, really important. And so when there’s time, pressure, and accuracy, and when someone is learning something new, it’s just hard to kind of let go in that situation.

LOVE: So, if you were going to advise a manager who kind of found themselves in this situation where they were in these high-pressure situations with an untested team that they just felt like they couldn’t trust, like ... what? It seems like there’s something bigger-picture that needs to happen. How would you advise them to start even thinking about that bigger picture?

ELLINGTON-BOOTH: I really have them think about literally kind of mapping their employees in their head, in terms of where they are in terms of skill, and just the amount of confidence they have in their employees, the ability to get the work done. You know, it’s still about trial and error, and giving people the grace to fail, and being comfortable with giving constructive feedback. So that’s another skill that I think is largely, I mean, everyone knows it’s important, but I don’t think organizations do a good job of really training people how to give good feedback that doesn’t make the manager feel like, well, you know, I have to criticize this person. And getting over just that psychological barrier if they haven’t had any role models to know how to do that, well, that’s just challenging in general.

LOVE: I really like what you just said now, which is almost this idea of, like, I don’t want to hurt people’s feelings, or I don’t want to be mean. And I think there is an element of leadership or management that is kind of saying, like, “no, this is what you are going to do. And this is what you are going to do. And this is not like a full, uh, democracy here.” Is that something that you find leaders sort of who are newer in that position struggling to accept?

ELLINGTON-BOOTH: Yeah, I think it’s not an either–or. It’s not either you’re strong and tough or you’re too soft. There is this notion that you need to be self-assured and confident and, um, having true self-confidence, which a colleague of mine, Harry Kramer, will say is knowing what you know, and knowing what you don’t know, and being okay with both. And, you know, just knowing that for yourself, it’s really finding the balance. And it’s really about you communicating, giving people an opportunity to show what they can do and knowing when to, like, “okay, this person has got it, I can give them more.” And then it’s like, “ooh, this person needs a little bit more hands on.” And so there’s no one-size-fits-all for delegating each employee that you have. And that’s what makes this work—leadership, management, delegating—really hard.

LOVE: Yeah, it’s interesting because, of course, my next question was going to be like, “well, what’s the one, you know, magical strategy for making sure that you’re delegating everybody, you know, the right amount of things in the right amount of clarity?” And what you’re kind of saying is it’s almost like a read-the-room type situation where you have to know your team and their capabilities and the context of the work environment, so clearly that that is going to be what informs strategy.

ELLINGTON-BOOTH: Absolutely. So the strategy is more about reading the room, understanding, the strengths and weaknesses of your team, making sure you are clear about your own expectations, and then communicating that clearly to others.

I think the biggest thing that I see in organizations in these roles is just people make so many assumptions.

LOVE: Hmm.

ELLINGTON-BOOTH: And they forget that, you know, maybe their direct reports don’t have the same experience-base that they do. Or they forget that they learned how to do this because it was trial and error, and they kind of figured it out on their own. And then they want to kind of spoon-feed the employees too much. And so it’s really ... I think the strategy, if you will, is to really do some critical thinking about what’s expected, and how do I want their product—the direct report’s product—to be, and being really clear about it. It’s just, I like to think of managing as this Rubik’s Cube that keeps changing every day.

LOVE: Mm, I guess that’s why we’re here talking about it today. That’s why people are like, whoa, how do I get this right?

Does delegation really change that much as you move up in an organization as you become more senior? So on the one hand, you know, certainly the tasks that you’re delegating are probably going to change significantly as you move along in your career, but does your philosophy or strategy for thinking about it change? Are there sort of some things that you should always be keeping in mind and looking out for?

ELLINGTON-BOOTH: That’s a great question. In my mind, there’s a distinction between the “what” versus the “how,” and maybe the “what” might be clear, but the “how” might be different as you move up in the organization.

LOVE: Say more about that, yeah.

ELLINGTON-BOOTH: So you still have the same basic strategy where you have, you know, direct reports instead of now them being entry-level employees. They might be managers or even directors and they have their own team. So the “what” is getting things done through other people. But the “how” is different. Different because there’s another layer of it, because the other layer is not only getting things done through those managers that have direct reports, but also helping them coach and mentor on the people side of things, as well.

And what becomes really challenging the higher up you go in organizations is that you lose touch with how managers work ... are really doing ... or how those entry-level employees ... what their experience is. How do you really know what’s really going on?

LOVE: Yeah, it almost becomes like a game of telephone at a certain point where you don’t really know because every single point of connection, there’s some opportunity for information flow to be lost.

ELLINGTON-BOOTH: Absolutely. Yeah.

LOVE: Have you ever encountered a scenario where a leader was struggling to delegate because to delegate would require them to know what they actually wanted out of a project?

ELLINGTON-BOOTH: Yes. All the time.

LOVE: You said that very quickly.

ELLINGTON-BOOTH: Well, that’s like the main thing that I see all the time.

LOVE: Really?

ELLINGTON-BOOTH: The biggest mistake most managers make, seasoned and unseasoned, is not being clear about expectations.

LOVE: Mm hmm. Mm hmm.

ELLINGTON-BOOTH: Being clear about, first of all, their own expectations. A lot of times a manager and their boss, they may or may not be on the same page. And so if there’s not alignment with that relationship, that cascades down. And managers tend to sometimes not know how clear to be about expectations. And people either fall into ... they over-explain, they micromanage, or it’s like, “well, I want to give people autonomy.” And then it’s like too little, but it’s almost like the Goldilocks syndrome where you just kind of have to get that just-right spot. I mean, I’ll even use myself as an example: So before, you know, I became this quote-unquote “expert” that you said I am ...

LOVE: You are. I have. Objectively.

ELLINGTON-BOOTH: Yeah. I worked in an organization, and I had a manager that was not good in terms of explaining her expectations to me. And so, you know, she was kind of hands-off. And then I thought I did a good job. And then when I presented my work to her, she was like, “this is horrible.” And I was mortified. And it would have been helpful if she had shown me an example.

LOVE: But did she even have an example?

ELLINGTON-BOOTH: She did.

LOVE: Or was it like a “I know it when I see it” type situation?

ELLINGTON-BOOTH: I think she had an example in my case. And ...

LOVE: ... she just didn’t tell you?

ELLINGTON-BOOTH: She didn’t tell me. But to your point, there’s another ... “I know it when I see it.” And that can be hard. But, it’s one of those things where people have to be really clear about what a really good product looks like.

LOVE: Mm hmm. Yeah, and it sounds like it would just be way more difficult in a really creative profession.

ELLINGTON-BOOTH: Absolutely. Yeah, I mean, that job I was talking to you about was an advertising agency. So you can’t get any more creative and subjective than that. So when there’s that level of subjectivity, how do you know when it is? Or, you know, it’s one of those, “well, it depends.” And that’s really hard to train, other than maybe getting input from other people, having a lot of different eyes look at it. And that kind of should be hopefully baked into the process. But a lot of times it’s not.

PAVIN: So, delegation is still pretty nebulous. You have to read the room. You need to know what you want from a project. But Brenda’s helped us get a lot closer to figuring this all out. She said that understanding your employees is key. Map out their strengths and weaknesses, be clear about your expectations, and offer clear constructive feedback. Allow space for trial and error where the stakes are lower, then build up as you gain trust in your employees’ abilities.

But how does all this translate to real-life management decisions? In part two of this series, we’ll go a little deeper. What should managers delegate more of? And what should they avoid delegating?

Delegation can go very wrong when the stakes are high, but sometimes it’s worth doing anyways. Find out more next time on Ask Insight.

[CREDITS]

PAVIN: This episode of The Insightful Leader was produced and mixed by Isabel Robertson. It was produced and edited by Laura Pavin, Jessica Love, Fred Schmalz, Abraham Kim, Maja Kos, and Blake Goble. Special thanks to Brenda Ellington-Booth. Want more The Insightful Leader episodes? You can find us on iTunes, Spotify, or our website: insight.kellogg.northwestern.edu. See you next time.