How to Delegate

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HANNAH BATES: Welcome to HBR on Leadership, case studies and conversations with the world’s top business and management experts, hand-selected to help you unlock the best in those around you. Delegating is a skill that’s often overlooked. And yet, it’s an essential part of leadership. Without it, how can you rise above the tactical grind and focus on strategic thinking? But delegating well is harder than it may seem. Today we bring you a conversation about how to get delegating right for everyone involved – with the help of leadership coach Deborah Grayson Riegel  and Jasmine LeFlore, an aerospace engineer who’s struggling with the awkward aspects of delegation. In this episode, you’ll learn how to decide which tasks to delegate and how to handle the specific challenges that come with delegating to peers in your organization – not just direct reports. This episode originally aired on Women at Work in April 2022, as part of a special series called “The Essentials.” Here it is.

AMY GALLO: You’re listening to Women at Work from Harvard Business Review. I’m Amy Gallo. To learn how to delegate in a way that delivers the results you were hoping for, we’re bringing in a rocket scientist. No, not because delegating effectively is rocket science. Even Jasmine Leflore, an aerospace engineer at Raytheon Technologies, finds assigning colleagues tasks to be tricky – so tricky that she doesn’t always ask for the help she needs in both her day job and in running a nonprofit that teaches girls about engineering and business. But now she’s ready to confront the difficult and awkward parts in order to delegate more and better.

JASMINE LEFLORE: I think delegation will definitely help me be more prepared and be able to focus on the things that I am best at and can have more deep work on.

AMY GALLO: These are the sorts of outcomes that make entrusting others with work worth doing for anyone, you and me included. Deborah Grayson Riegel coaches leaders on shifting their mindset and behaviors in order to delegate clearly, conscientiously, and productively. She’s here to talk us through practices that will not only ensure the work gets done, but also will leave you and the person you delegated to feeling good about the experience. Jasmine, Deb, thanks so much for joining me on the show today.


JASMINE LEFLORE: Thanks for having me, Amy. I’m happy to be here as well and nice to meet you, Deb.


AMY GALLO: Jasmine, I want to ask you, would you say delegation is something you do a lot of already or is it something you’re looking to do a lot more of?

JASMINE LEFLORE: I would say both. I would say for my nonprofit, delegation is definitely important. Right now, I have a co-founder and part-time staff. So, going from one person doing all the work to it’s about seven of us who are involved hands on in a matter of three months has been a lot of delegation. I think about the apprentice program I’ve started where some college students who are studying engineering are now helping teach students about engineering entrepreneurship. So, my co-founder and I, we’ve been doing this framework that has been going very well and I really enjoy doing it, but in the same breath as a founder, co-founder, executive director, I think my time is well suited working on the business instead of in the business, so to speak. So, teaching college students to teach this curriculum has been very rewarding to see where they have those fresh eyes and they’re providing feedback and showing me things that I didn’t even think about when I started developing this framework, and I would say my role at RTX, I delegate to a lot of my peers. So, that one is a little bit more sparse, but I intend to delegate more as I move up in my career.

AMY GALLO: Yeah. And just to clarify for our listeners, RTX is Raytheon Technologies. You can use that acronym now that we clarified it, but just want to make sure everyone knows what we’re talking about.

JASMINE LEFLORE: Thank you. Yes. Raytheon Technologies, business unit Collins Aerospace.

AMY GALLO: Yeah. And Deb, what do you hear in what Jasmine’s saying about the importance of delegation as well as the challenges that many of us face?

DEBORAH GRAYSON RIEGEL: I’m hearing Jasmine hit the nail on the head. As she delegates, she gets to lighten her workload, she gets to crossings off her to-do list, is she’s going to challenge herself, improve and increase her value to the organization, and there’s benefits to the team as well. And one of the things, Jasmine, that I heard you say that I want to, at some point, make sure we talk a little bit more about is delegating to your peers, right? We often think about delegating as something we do to direct reports, and I’m hearing that you’re in a situation where you’re delegating to colleagues which certainly has some benefits, right? It makes them feel more trusted or more respected. They have the opportunity to learn more skills, collaborate more, you might even get a day off every once in a while if you have people who know how to do what you know how to do. So, it sounds like Jasmine is really focused on the benefits not just to herself, but to the team and the organization. And I really like the idea of delegating to peers.

AMY GALLO: Yeah. The idea that delegation isn’t just good for you, I think is critically important. And I actually want to bring in some research that’s been done about delegation in women specifically, that women tend to delegate less. They also tend to feel more anxiety and guilt about doing so, and that’s partly because they see it as a dominant thing to do. The researchers who did these studies… actually, the advice they suggest is to do exactly what you were just saying, Deb, which is to focus on the benefits of delegating not just for yourself, but for others – how it helps them learn, how it helps them grow, and I think that’s something we lose sight of. Listening to both of you talk so far, I’m already thinking about the things on my to-do list. I’m like, who can do that? Who can do that and how it benefits me, but I think the other way of viewing delegation of like, who actually could learn from this task, who could develop their skills as a result of doing this task, it’s just a very different take and would allow for that delegation to peers in a way that wouldn’t feel necessarily uncomfortable or inappropriate.

DEBORAH GRAYSON RIEGEL: And I’m also thinking about the research that shows that when women get feedback from all genders, when women get feedback, it tends to be about her teamwork and collaboration and less about her leadership. So I want to be mindful that if we are encouraging anyone to delegate more, that we don’t just think about it as a teamwork and collaboration skill, we think about it as a leadership skill as well.

AMY GALLO: Jasmine, I see you nodding. Does that resonate with you?

JASMINE LEFLORE: It does as resonate with me. I like feedback so I feel like I don’t get enough of it, and when I do get it, does feel like sometimes it’s based around that collaboration or maybe just being organized, but not necessarily the leadership aspects that I’m showcasing.

AMY GALLO: And Deb, can you articulate exactly how delegation is a leadership skill?

DEBORAH GRAYSON RIEGEL: Well, in order for you to be a leader, you need to be thinking more strategically and less tactically. You need to enable other people to grow, develop, and take things on rather than you having your hands in every single thing. So, in order for you to become more visionary and strategic and coach and guide other people to do the work so that you can be working on other things, you can’t still be doing everything yourself.

AMY GALLO: So, we know delegation is a critical leadership skill. We know it benefits not just you, but other people. Let’s get into how you actually do it. Deb, what steps do you recommend we take to decide whether or not to delegate a task, a decision, a responsibility?

DEBORAH GRAYSON RIEGEL: There are some common misconceptions I think people have about what to delegate, and I think people think that they should delegate things that are really boring, things that are really small so that you can follow up really quickly. I want people to think more broadly about what they can and should be delegating. So, as you think about your own workload, you want to think about things that might feel routine for you, but may not feel routine for somebody that you’re trying to develop. You might want to think about something that has been fun for you and it’s time to share the fun with somebody else who might think it’s fun. You might want to think about tasks that other people can clearly do better than you can, tasks that eat up your time, tasks that will develop other people so that you can move on to other things, and so that they can move on to other things are really good things to think about in terms of delegating. And of course, there are some things that you just shouldn’t delegate. One example would be if somebody delegated something specifically to you because they want you to do it, don’t give that to somebody else.

AMY GALLO: Don’t pass the hot potato.

DEBORAH GRAYSON RIEGEL: Don’t pass the hot potato. The last thing that I would say when I coach leaders on delegation and teach workshops on it, number one thing that people go, “that’s something that I’m doing that now I realize I shouldn’t be doing” is that people delegate poorly defined tasks to other people where they’re not clear of the expectation. They’re not clear on the goal. They’re not clear on what success would look like, and they pass that on. And as you can imagine, it’s like a giant game of telephone. It just leaves you a mess.

AMY GALLO: Yeah. I want to get more into that in a moment, but there was something that came to mind also that I realized would be worthy of delegating, which is something you’ve done for a long time. and maybe someone with fresh eyes could do a little differently.

DEBORAH GRAYSON RIEGEL: Absolutely, and I’ll just share that part of delegating is expanding your comfort level and definition of what “can do it” means. So, if your definition of can do it means they can do it exactly the way I can do it and have always done it, that’s a pretty small pool of people that I could delegate to. Sometimes it’s n=0, but if I’m willing to expand my comfort level and understanding of what “can” means, I have a lot more options and it brings a lot more diversity of perspective, as you said.


AMY GALLO: So, Jasmine, as you’re listening to Deb, what tasks are coming to mind? What are you thinking about wanting to delegate?

JASMINE LEFLORE: Yeah. So, in my day job, I’m starting a new project where I’m going to be helping create some virtual interactive demos for our products. So, I’m coming up with almost like a one pager of what our technology does, the benefits of it, who it serves and being able to delegate that to our younger engineers or early careers to do that for all of our projects. So, I’m basically starting off with one of our key products. So, it might be a very specific piece that I am creating a story around, but being able to delegate that to someone to continue that work is something I’m looking forward to doing.

AMY GALLO: Yeah. Deb, is that something you recommend – that you either do a piece of the work or do an example of the work before you delegate it? What prep do you need to do before a task is actually ready to pass off?

DEBORAH GRAYSON RIEGEL: Yes. You do want to think about, how are they going to learn what it is that I’m looking for? So, some steps might include being really clear about what it is you are expecting in terms of the outcome. You might even provide an example of what a successful outcome can look like. This is also the place to distinguish whether it is a certain outcome or a range of acceptable outcomes that you’re looking for. You want to get really clear whether it has to look exactly like this or once we’ve agreed on what success looks like, there’s a range of possibilities. You certainly want, in addition to providing examples of what it would look like when done well, you want to clarify how the task you’re delegating fits into the big picture, and I think that’s a thing that a lot of people miss is putting it in the context of why this matters. So, even Jasmine, I heard you say that, “I’m delegating a part of something.” That’s totally fine. We also want to communicate how that part fits into the whole so that people can get that big picture. You want to talk about how you’re going to evaluate progress, process, and outcomes. So, those are the things that can really help set somebody up for success.

JASMINE LEFLORE: You made me think of setting parameters. So, in engineering you set up you want your length to look like this width so on and so forth. You made me think of how to set up parameters to set someone up for success. Do you think managers should be creating almost like a checklist parameters, so to speak, before they pass on a project to someone they’re delegating to?

DEBORAH GRAYSON RIEGEL: What strikes me is that if you do that, you reduce the risk of what we call micromanaging, right? So, nobody wants to be a micromanager. That is for sure and yet-

AMY GALLO: And no one wants to be micromanaged.

DEBORAH GRAYSON RIEGEL: Thank you for offering a fair and balanced perspective. Nobody wants to be the micromanager and nobody wants to be micromanaged, and yet I think we misunderstand what we mean by micromanaging, right? So, if there is somebody who has never done something before, has limited knowledge and limited experience, you showing them what success looks like and walking them through the process is managing. That’s not micromanaging. To do anything other than that would be under-leading them, right? So, Jasmine, it’s your first day on a particular task and I go, great, well, my door’s open. Let me know if you have any questions. That’s the opposite of micromanaging – that’s under-leading. So, I think what you’re describing Jasmine in terms of a checklist is absolutely something that can set people up for success so that they don’t micromanage and aren’t micromanaged.

AMY GALLO: Yeah. Well, I like the way you put the engineer take on it, Jasmine – that it’s these parameters, right? It’s the what, who, when, why, and where, right? Thinking that through very clearly. Though I have to say, I think most people want to delegate because they have way too much to do themselves, and yet what we’re describing is a very time intensive prep to pass this task, right?


AMY GALLO: Like, part of me wishes delegation was as easy as walking past someone’s desk, hopping on a Zoom and being like, “Can you do this task? Great. Thanks,” and then just get off. That’s the time crunch most of us are under.

JASMINE LEFLORE: Yeah, because I would say I spend a lot of time crafting that parameter message of whatever I’m delegating to, and sometimes I feel like I’m delaying them from doing the work because I’m putting a lot of effort into, okay, let me make sure I told them everything.

AMY GALLO: Yeah. How do you know you’re spending too much time preparing a delegate versus the right amount of time? Deb, what do you think?

DEBORAH GRAYSON RIEGEL: Most people’s instinct would be to say, this is taking too much time because if they believe that it’s taking too much time, they won’t do it and they won’t have to do it. I think we actually want to challenge our confirmation bias that this is taking more time and it would just be easier and faster for me to do it myself. It’s going to be more likely that it is taking the right amount of time which is longer than it feels comfortable. I would say that if every single thing you are delegating takes a significant amount of time, then you are probably not doing it right. So, I often think about tasks for which I have a very hard opinion. This is exactly what it needs to look like and how it needs to be done. Tasks for which I have a soft opinion, I’ve got some ideas of what I think success would look like, and I’m really open to yours. Then tasks around which I have no opinion, I don’t know how to do this. I don’t want to do it, you do, take it on, and if for all three of those tasks I’m spending hours and hours and there’s something wrong in my process.

JASMINE LEFLORE: I like that. You made me think about, I did the Jenny Blake assignment on how to decide what tasks to delegate, and she has this really great framework where it’s six Ts. So the six Ts are, Tiny, if it’s something super small, you don’t think about it; Tedious, something that you don’t necessarily want to do, but it has to get done; Time consuming, obviously time consuming; Teachable, teachable, you can pass it on and there might be some gate checks you want to do; Terrible at, meaning you’re not the expert. This is not what you do; and in time sensitive, it’s critical, it’s hot, you got to get it done. So, you made me think about the teachable tasks that I’m giving to the apprentices or just where it’s more of me doing a gate check of what they’ve created versus me having a hard line of this is what it must look like.

AMY GALLO: Yeah. I’m thinking about this. There was a task I have done at HBR for years and years which is to write our Management Tip of the Day, and I just assumed no one else wanted to do this because no one ever raised their hand. Then as soon as we put it out to a few other people, there were lots of people who were like, that would be super helpful to learn how to condense the long form articles into short pieces of advice. It was like, all right, as soon as I thought of it as not this tedious thing – because it became tedious to me since I had done it for so long – but something that actually would allow someone to exercise a really specific skill, it became teachable rather than tedious.

DEBORAH GRAYSON RIEGEL: Amy, I want to highlight something you said, if I may, which is the idea of waiting for people to put up their hands, right? Which strikes me as culturally nuanced, right? So, I am a third generation New Yorker – if I want something I’m going to tell you to your face. There will be no mistaking that I want it or I want to do it.


DEBORAH GRAYSON RIEGEL: And as somebody who has worked all over the world, volunteering for assignments looks very different in different cultures, and I think if we are going to become better delegators, especially in a global marketplace and global business place, we may need to expand our understanding of what volunteering for a task might look like.

AMY GALLO: Yeah. Well, and I want to go back to what you were saying earlier about delegating to peers, because this is my role at HBR. I don’t manage anyone. I don’t have anyone who’s a natural person to delegate to. It would always be delegating to peers, and I think that’s why I was waiting for the volunteer, I assumed everyone knew that I was burnt out on doing this, but no one had any… I had never even articulated that. So, can you talk a little bit it about the delegating to peers versus direct reports?

DEBORAH GRAYSON RIEGEL: I want to reinforce the point that many people don’t think they can or should delegate to peers, right? Unless there’s an emergency and then it’s all hands on deck. There are many individual contributors and organizations who need to get some things off their plate and don’t have somebody to formally and officially hand it to. So, I think recognizing that delegation is a request, not a command, especially with peers, right? So, the definition of a request is something to which somebody can say yes, no, or make a counter-offer, right? I can’t take this thing off your plate, but I’d be happy to do that thing – and to really be explicit that this is a request around something to look for opportunities that you think people might be interested in, might want to learn, might help them get exposure to something or someone that you have had exposure to that they may not. So, like selling anything else, you may want to sell the benefits of it to them. Then to carry through the delegation to a peer, Amy, I come back to the Harvard Business Review article that you wrote about compassion and accountability, right? Not being in conflict. You had a much more eloquent way of putting that, but that when you are delegating to a peer, you definitely want to demonstrate compassion for what may be on their workload, and once they’ve said yes, you got to hold them accountable for results in the same way you might do a direct report.

AMY GALLO: Right. Jasmine, you’ve had experience doing this. What best for you when you’re delegating to a peer?

JASMINE LEFLORE: I think it’s gone well when it’s something that they’re the expert at. I work with a lot of technical specialists. So, most of the time when I’m delegating to that type of peer, it really only makes sense for it to be them, but in the same breath, with me not being their manager, sometimes it is about they already have a workload on their plate and then they need to talk to their manager if this is something else they can take on. So ,then it’s almost this like limbo of, oh, should I have asked or is this that important? And am I not the priority because it’s me as a peer asking versus me as your manager. I’ve seen instances like that, but I wouldn’t say that I’ve had like a negative one.

AMY GALLO: It’s just been a little more murky, the response.

JASMINE LEFLORE: Yeah, and I would say when it comes to delegation – and I know you talked about this a little bit in the beginning about, like, women delegating – I try to ask in a way that is the least taxing. So, I think that goes back to me, I’m preparing so much on my end and I’m spending a lot of time like trying to do this work that is verging into, okay, now I need an expert. Then they probably only need to vet or do 10% of what that actual project is, but I feel like I want to almost not ask anybody anything. So, when I ask, it’s usually like a small piece in the workplace.

DEBORAH GRAYSON RIEGEL: Jasmine, I’m hearing you align really nicely with the research that we talked about a little bit earlier, the idea of that when women delegate, they tend to delegate less, and when they do it, they do it with more guilt and anxiety associated with it. That makes a lot of sense that you wouldn’t want to burden someone. I think that shifting the mindset from number one, believing that you’re issuing a command versus making a request, right – If you’re making a request, somebody can say yes, no, or make a counter-offer – and number two is, if you can genuinely frame it in terms of some benefits for them, this is something you’re interested in. This is something you may want to learn as you get to the next level. This is going to give you some visibility that you haven’t had before, and I’d love for you to take advantage of that. If you can do that from a genuine place, you’re actually being of service to somebody rather than asking for a favor.

AMY GALLO: Yeah. What do you do about the murky response of like, “oh, I’ll have to check with my manager.” Jasmine is describing that feeling of like, oh, should I have asked? Now I don’t know what’s going to happen. How do you manage that more clearly, Deb?

DEBORAH GRAYSON RIEGEL: Well, there’s the fact and then the story that we make up in our heads, right? So, the fact may be somebody said, “I need to ask my manager.” The story we make up is, “Now they’re mad at me for asking them, I’ve put them in a difficult place. I should have just kept it myself.” Separate out the fact from the story. I don’t know about you, but I’ve never made up a happy story, right? In the absence of information, I never made up, “Oh, my goodness they’re so excited. They don’t even know how to tell me.” So, if this is somebody with whom you have a good relationship and a clear communication and a history of feedback, you might just point it out to them. “Hey, I noticed that when I asked you if you could take this on, you said, ‘well, now I have to ask my manager.’ Is that something that you’re comfortable doing asking your manager, or is it something else? I’d really like to hear that.” So, it’s a little bit of calling them on it, but not in a combative way, in a way that demonstrates, you’re noticing that they had a reaction that you were actually clear about what it meant.

AMY GALLO: Yeah. Could you imagine doing that Jasmine?

JASMINE LEFLORE: I can imagine it. I have done it, but I don’t know if I received a positive response.

AMY GALLO: What response did you receive?

JASMINE LEFLORE: Well, I like to think of myself as a firm, but fair person or “let’s get straight to the issue,” and I don’t know if it’s surprising when I’m the person saying like, “Hey, can you tell me more about your reaction,” or “You mentioned you need to talk to your manager, but is there something else that’s coming up for you?” I think that’s something that isn’t typically done in the workplace or at least where I work, where people are ready to answer those type of questions truthfully.

AMY GALLO: So, do they not answer them or how do-

JASMINE LEFLORE: It’s like, “Well, I’ll see,” or “No, I’ll just talk to them.” It’s almost like I don’t get that answer outside of, “I’ll just talk to my manager.” This also kind of goes back to me saying, “I don’t think I get enough feedback for me to really understand how I’m being viewed or the perspective of my interactions with my peers and even my leaders.” So, I don’t mind almost like handholding to get the delegation done in terms of, “should I email your manager and CC you?” And maybe we can talk about it there. Should I set up a meeting with him? Like I’m almost willing to do that extra work just to make sure that you can get the task done, but I don’t think that that’s what I should be doing.

AMY GALLO: Why not?

JASMINE LEFLORE: I think it feels like I’m doing so much just to have you help me, and you are not really showing that you’re willing to do it without me overextending myself. It’s like, “I’ll ask my manager,” but back to what you said, Deborah, did you or are you going to?

AMY GALLO: When someone’s dragging their feet on a task, this could be a peer, like the situation with Jasmine this could be a direct report, how do you know how hard you should push versus just take it back or not ask next time? Deb, what do you think?

DEBORAH GRAYSON RIEGEL: I think dragging your feet is an interpretation that we may want to define a little clearer, right? So, dragging your feet could look like somebody sulking while doing it, right? It could be tone of voice, facial expressions. Dragging your feet could also look like missing deadlines, right? So, we want to be really clear about what behavior we’re observing that we’re interpreting as dragging their feet. Also, and this is both the coach in me and the mom in me that says, “I see people drag their feet, so we’ll take it back,” right?


DEBORAH GRAYSON RIEGEL: So, we want to be mindful about positively reinforcing a negative behavior if I know that every time I sulk, you’re going to be like, fine, I’ll do it, guess what I’m going to keep doing? Sulking, right?


DEBORAH GRAYSON RIEGEL: So, this is a place where that feedback culture is really important to say, “I’m noticing you’ve missed a couple of deadlines. I’m noticing that you’ve said, yes, you would do it, and then you made a face after. I’m curious, what’s going on there?” And that really does require that feedback is a regular part of your relationship and certainly a part of delegating.

AMY GALLO: Yeah. You mentioned being a mom and I will tell you with a teenager, this is a daily exercise because I’ve learned, “You need to get out the door right now,” doesn’t work as well as “What do you need from me right now to get out the door,” and I think the positive reframing of, “I’m here to help you, but you really need to leave right now or you’re going to miss the bus” – and I do think we can apply that to work of… I think about something I delegated that someone was late on for like four weeks in a row, and I had to say, “Okay, what can we do to help you make sure you can do it on time as opposed to taking it back which honestly is what I wanted to do because I was like, this will just be easier if I just do it, but trying to problem solve and being open to hearing why it was taking so much time. Have you tried something like that, Jasmine? Like, what do you need from me to get this done?

JASMINE LEFLORE: Yes. Exactly that phrasing, what do you need from me? What can I help you do to make sure that we’re successful with this project? A lot of times when I ask that I don’t get a response that is tangible. It’s more like, “Oh, I’ll let you know.”

AMY GALLO: Well, and in the cases where they say, “Oh, yeah, I’ll let you know,” I don’t know, Deb, do you have a different phrasing you would use that would encourage a more accountable response?

DEBORAH GRAYSON RIEGEL: Well, I’m going to push back at the overuse of the word “we.” So, this is something that I hear all the time. “What do we need to do to get this done? When could we expect this, right? When will we see the next step?” No, right? As soon as it’s “we,” right? We say that because it’s friendly, it feels collaborative. It’s more teamwork, right? There’s no “I” in team, but one person is accountable, and so, I’m going to invite people who feel like perhaps they’re a little too soft when it comes to delegating to get rid of the word “we,” unless the word “we” is absolutely what you mean. So, “When will you have this done? When will you let me know progress? When will you tell me the next step,” really points the spotlight on, “Who is getting this done?”

JASMINE LEFLORE: I like that. Yeah. Thank you for that because I said it, but you made me think of, like, a RACI chart, R-A-C-I – Responsible, Accountable, Consulted, Informed. Usually, the A means that person is accountable for getting the work done, and there’s usually only one person that is an A on the team. You might have a few Rs, you might have few Cs, a few Is, but usually it’s only one person on the team that’s an A, the accountable person. So, I feel like what you said fits that very well in terms of what does that person need? What do they have to do? What does that accountable person need to do to get it done?

AMY GALLO: I want to continue on this language question because I have worked with an executive around my speaking and consulting business. Her job is to support me. My job is to delegate things to her, and I still struggle with the right language to introduce new tasks. So, “I need you to” feels somehow, like, too assertive or even abrasive, but “can you do this thing” is disingenuous because she needs to do the thing. I’m not actually asking her, “can she,” I’m telling her she has to. Deb, any advice about the right language to introduce a task like that?

DEBORAH GRAYSON RIEGEL: In your case, Amy, I might even ask her, “When I share a task with you, what language makes it clear, feel okay to you.” It strikes you as respectful. So, I would always go to the source. What I might do is to say, “Here’s a task that’s coming up. Here’s why it’s important.” So, remember to put it in the context and to say, “I will want your help on this. When is a good time for us to talk about it in more detail?” Schedule something like that, but I kind of just put it on the table and then talk a little bit about timing and deliverables for having the delegation conversation.

AMY GALLO: I like the idea of asking her because I have a feeling she would say, “Well, just tell me what I have to do.” She probably has impatience with the hemming and hawing I do in the language, but that’s just a hunch, and why not just ask her, right?


AMY GALLO: Deb. So, you’ve delegated. What questions do you ask to assess whether they’re actually ready to go off and do the thing? That they actually understand the expectations, all of that.

DEBORAH GRAYSON RIEGEL: I’m a big fan of asking them to sum up what they heard me say. Quite often when people delegate, the delegator is the one who sums it up. So, “I just want to be clear, Jasmine, you’re going to do this by this date and here’s when our milestones are going to be.” Well, all that means is that I, as the delegator, knows it doesn’t tell me anything about what Jasmine might understand, right? So, ask the other person to sum up what they’re hearing if it’s appropriate, ask them to put it in an email so that you can capture their understanding of it. When I went to coaching school, we learned three questions that you ask at the end of coaching engagement which is, “What are you going to do next, by when, and how will you let me know or when should we check in about it?” I think when you are delegating to somebody who is new to a task, you would tell them rather than answer that. So, here’s what I need you to do next, by when, and here’s what I want to check in about it. As you are delegating things where people actually feel more educated and empowered, you would want to shift from answering those yourself to asking them.

AMY GALLO: Jasmine, what do you do when you’re assigning a task?

JASMINE LEFLORE: I’m a big proponent of using project management tools like ClickUp and Trello and just seeing cards move from “to do” and “work complete.” So, when I see that my virtual assistant is complete with a task or has some questions, sometimes she’ll just add some notes into our click up of, okay, I’ve done this, but can you clarify this? Do you think that’s effective when it comes to working with a virtual assistant in terms of tools as your place of conversation or clarification?

AMY GALLO: I think so. I think that the idea of – right now I’m like, okay, I need to start a Trello Board because I do think that… because there’s so many conversations where I’m like, where does that thing stand? What happened with that – where I’m following up, and if it was visible to me in some way, it would eliminate the need for us to go back and forth, and I do get concerned that my constant questioning signals a lack of trust. So, if I could actually see it, then I wouldn’t have to convey that I’m doubting that she did it, even though I’m really just curious whether she has. I don’t know. What do you think, Deb?

DEBORAH GRAYSON RIEGEL: I think if you have tools that work for both of you, have at it.

AMY GALLO: Yeah. Let’s talk about that tracking for a moment because we’re talking about the wanting to be hands off, to let someone have the room to do what they need to do without being micromanaged. And it will depend on the task of course, but once you’ve actually entrusted someone with a task, how do you assess how involved you need to be?

DEBORAH GRAYSON RIEGEL: I think at the beginning, when somebody is new to a task, you should be involved, right? If they are just learning how to do it is not micromanaging them for you to be involved. It would be underleading them for you not to be involved. At a certain point, there is going to be a shift in the ownership or the responsibility of it, and in my mind, that’s a conversation, right? “Up until now, I’ve been checking all along the way. At this point, I think you’ve demonstrated that you know how to do this, I’d like you to now take these steps without me and then let’s plan to check in for the next part.” So, I think it’s a continuum. I often think about it in terms of when my kids were learning to drive at a certain point, I needed to stop grabbing the wheel. I don’t know that that will actually ever happen, but I wasn’t going to stop grabbing the wheel for as long as they actually didn’t know what to do or how to do this, right?

AMY GALLO: That’s a helpful metaphor. Yeah.

DEBORAH GRAYSON RIEGEL: So, having a conversation based on your observation of what their skill level is, what their knowledge is, and their motivation to do it as well. So, they may be really skilled, but if they hate doing it, you can be assured that they will drag their feet. In that case, they might need a little cheerleading as opposed to instruction.

JASMINE LEFLORE: Deborah, when it comes to taking that wheel, how do you do that in a way that doesn’t make that person feel like they’re not doing it right?

DEBORAH GRAYSON RIEGEL: A couple of thoughts: Number one is to say exactly that – actually communicate your intentions. “There may be parts of this project where I need to put my hands back on the wheel. Even though I said you’re the driver, when that happens, I will let you know and I will explain why.” And of course, if you’re in a crisis, you don’t have to let them know and you don’t have to explain why. That can come after, right? You also want to think about timing that there may just be things where the risk is too high and you just need to take it back, and you may also want to have after action reviews about how a process went. “Do you think that I gave you enough responsibility earlier on? Do you think I let you go too long without me stepping in?” This is again, one of the reasons why having a culture of feedback with anybody that you’re delegating to is really important.

AMY GALLO: Yeah. Is that helpful, Jasmine?

JASMINE LEFLORE: That’s very helpful.

AMY GALLO: Yeah. Deb, what if you’ve delegated something to someone and the person just isn’t doing a good enough job? Perhaps you could have delegated the work better in the first place or you tried to reset and it didn’t actually work, how can you take the task back without damaging their morale or their confidence?

DEBORAH GRAYSON RIEGEL: There’s the damage of somebody’s confidence or morale that comes with doing something poorly, and there’s the damage of somebody’s confidence and morale that comes with you taking something back, right?

AMY GALLO: Good point. Yeah.

DEBORAH GRAYSON RIEGEL: I think that this is, where is there going to be less harm done? And in many cases, less harm is done by actually taking the task back and getting it done right, and it’s worth having a conversation. So, to talk about, “Look, I recognize that I delegated something to you, it didn’t turn out the way either of us hoped and I took it back. I imagine that that had an impact on you and I want to hear about that. Let me start by sharing my contribution of how I actually might not have set you off on the right foot. I think that’s what I did. Would you share with me a little bit about how you think you might have contributed to this not turning out the way either of us had hoped?” So, get rid of fault, get rid of blame, get rid of shame, and talk about contributions because chances are, you both had some.

AMY GALLO: Yeah. When you first used the word contribution, I thought you were going to say, talk to them about what they did contribute even if it wasn’t completely filling the task, right? Like, “You got me the first step there, I’m going to take it back. This was an important step, but I need to own it from here on out because we’re not getting the results we need.”

DEBORAH GRAYSON RIEGEL: Yes. So, that idea of giving some positive feedback, even if the feedback isn’t about the outcome, but the feedback is about the process or a part of the progress that they made or even how well they handled the feedback that you needed to take it back, absolutely.

AMY GALLO: Yeah. Deb, our last episode was about managing up, and I imagine there’s times when you need to tell your boss that you’ve delegated something, that you need to keep them informed of why you’re doing that. In order to manage perceptions of you so that you don’t look like you’re just trying to toss off work to someone else, what are some situations where you think it might be helpful to keep your boss informed of when you delegated versus when it’s just the normal course of business?

DEBORAH GRAYSON RIEGEL: I think there’s the business-as-usual delegation where you may want to ask your boss, “How much of that do you want to be informed about?” Because some bosses want to know about everything and some bosses are like, “Tell me if something blew up in your face, other than that, I don’t need to know.” So, number one is asking them for their expectations. If you are delegating something to somebody so that you can focus on a development area for yourself, you want to tell your boss that, right? So, an example might be, “In our last performance review, you told me that one of the things that I really need to work on is being more innovative. In order for me to spend more time being innovative, these are the tasks I’ve delegated so that I can focus that.” That is a win-win right there, right? I heard your feedback, I’m taking the feedback, and I’m giving things away so that I can work on that. You also want to be mindful that part of your job is to be an ally, an advocate, and developer for the people that you are managing. So, if you are delegating things to people on your team that you hope will give them increased visibility, grow their own skill sets, work on their own career development, you may want to bring that up to your manager as well so that they can see the progress that you see.

AMY GALLO: Right. Jasmine, you told us at the beginning there’s some tasks you haven’t delegated yet that you’d like to. What are you taking from this conversation in terms of how to actually get those things off your plate?

JASMINE LEFLORE: Yeah. So, what’s coming up for me are the tedious tasks. Right now I’m doing a robotics program where I’m interacting with students and parents, and I have to take attendance, that type of thing. That’s a task that I don’t think I need to do, but it’s something that doesn’t have this hard line of, “it must look this way.” So, that to me is a task I can easily delegate to my virtual assistant. She can come up with this spreadsheet herself and propose it to me, and I can give her a timeline of when I’m looking to see that work done and using the phrasing, “When can you have this done by and do you understand the goal of this task, and do you have questions for me,” more definitively than me coming up with the entire Excel sheet and all these different things for her. This is the type of task that has a lot of flexibility. The goal is track the students in the program and track their parents registering them.

AMY GALLO: Right. Deb, any final thought what Jasmine’s saying around what she’s going to do differently and how she’s going to do it?

DEBORAH GRAYSON RIEGEL: Yeah. I’m appreciating that you are using individually accountable language, right? “What are you going to do? When can I expect to see something from you as well?” And I’m also noticing that you have some close ended questions in there like, “Do you understand?” I would also compliment that with some open-ended questions – “What parts of this do you understand the best? What parts of this still feel confusing for you?” – so that you make it okay for people to not completely understand it and they have choices beyond yes and no. I’m getting the sense that you are really ready to lean into your own impact and the respect that you deserve from the amount of work that you’ve put into your role to now ask people to take on things so that you can continue to develop.

AMY GALLO: Thank you both so much. Jasmine, I have to say I think you’re our first rocket scientist ever to be on the podcast. Thank you for upping our game. Deb, thank you so much for sharing your always very practical advice. This has been really helpful to me.

JASMINE LEFLORE: Thank you for having me.

DEBORAH GRAYSON RIEGEL: Thank you so much for having me.

HANNAH BATES: That was leadership coach Deborah Grayson Riegel and aerospace engineer Jasmine LeFlore in conversation with Amy Gallo on Women at Work. We’ll be back next Wednesday with another hand-picked conversation about leadership from the Harvard Business Review. If you found this episode helpful, share it with your friends and colleagues, and follow our show on Apple Podcasts, Spotify, or wherever you get your podcasts. While you’re there, be sure to leave us a review. We’re a production of the Harvard Business Review – if you want more articles, case studies, books, and videos like this, find it all at HBR dot org. This episode was produced by Amanda Kersey, Anne Saini, and me, Hannah Bates. Ian Fox is our editor. Music by Coma Media. Special thanks to Rob Eckhardt, Tina Tobey Mack, Erica Truxler, Maureen Hoch, Adi Ignatius, Karen Player, Ramsey Khabbaz, Nicole Smith, Anne Bartholomew, and you – our listener. See you next week.

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