How High Achievers Can Learn to Delegate: Coaching Conversation

Welcome to the executive coach for moms podcast where we support women who are attempting to find balance and joy while simultaneously leading people at work and at home. I'm your host, Leanna Laskey McGrath, former tech exec turned full time mom, recovering perfectionist and workaholic, and certified executive coach. 

Hi, everyone! Welcome back to today's episode, Episode Seven. So if you've been following along, I just finished up my three part series with Andrea, who was interviewing me about my story. And if you had a chance to listen to part three Andrea asks me about what I'm doing now and what's next for me. I talked about how I've relaunched my coaching business, and how now I'm doing executive coaching for high achieving women. And when she asked me what coaching is, I did my best to describe it in that moment. But it can be kind of tricky, because coaching can be so transformational. But it's just kind of hard to explain until you experience it for yourself. So I thought for this week, I would share a coaching session that I did that I think would be really helpful for anyone who's ever struggled with delegating, which is pretty much all of us. If you're a perfectionist, or a high achiever, it's likely that this is a struggle for you, or it's been a struggle for you, whether at work with your colleagues and employees or at home with your kids and your partner. And we talk about both in this session. 

So the two people that I'm talking to in this coaching conversation are Erica and Jen. Erica is a mom of three, who recently left the corporate world to start her own business. And Jen works in the corporate world as a senior manager and is a mom of two. Both Jen and Erica are very high achievers who have very high expectations of themselves. And I know that because I've actually worked with both of them in the past. So this conversation was so much fun, with lots of really great insights about what's stopping them both from delegating, as well as some insights and strategies and mindsets that they came up with to overcome that. Because if we're gonna get everything done that we want to achieve in this lifetime, we're going to have to learn to share the load, we're going to have to learn to delegate to others and let go a little bit. So I always love hearing coaching sessions. Because no matter what the topic, I feel like I always walk away with some insights that I can apply to my own life. So I'm really excited to hear about what your takeaways are, from listening to this coaching session, even if this is an area that you've already addressed. And you feel like, yeah, I've got delegation down pretty well. I think it's always fun to listen and see how far we've come and also what learning opportunities might still be present. Now, also, if you're interested in doing a coaching session for the podcast, look for the link in the show notes for more information. And now here's our coaching conversation, I hope you enjoy and have some really great takeaways. 

Hey, Erica, and Jen! I'm super excited to jump into talking about delegation, because I know that something that both of you have had challenges with, but I think both of you come at it from a different place. And when I was kind of thinking through, how would I kind of characterize like, how they're coming out this? I was thinking about that generally, delegation, I think is hard for us. For two reasons. One is that quality, so we're afraid that people aren't going to do it as well as we can. So maybe kind of like that perfectionism sneaking up, like it has to be done perfectly. And only I know how to do it the perfect way. And nobody else knows that. And then I think the other concern about delegation is speed. So I could just do it faster myself, I think is the thought that we often have about delegating, because it's like, okay, well, if I tell this other person to do it, I'm gonna have to teach them how to do it, and then they're gonna do it, and what if they mess it up? And I'm gonna have to go back and do it again. And I think that probably both are considerations, and both are challenges for everybody. But I would if I'm characterizing this correctly, and I'm very interested to hear your thoughts about this. I think Erica, your concern is probably more than equality. Like, I want to make sure it's perfect, and I want to make sure everybody, I want to make sure it gets done the way I want it to get done. And I think Jen, your primary concern is more speed, because I know like perfectionism isn't as present for you. Um, and it's more about being efficient, and making sure that everything gets done in the time that it's supposed to get done. So as I'm saying that I'm curious kind of like how that resonates? Or what shown up for you? Oh,

Jen  5:12  

Yeah, for me, it's, it's definitely a mix of both. There's the speed piece, because if the quality is not there, then I have to double back and do it myself. I've had a lot of conversations with my VP about this in the last year is, he brought up a really good point that I'm able to ask myself now, like, Do you not want to delegate some something because you want to control it? Or because you don't trust the quality of how it's going to be done? And the answer to that might be different depending on who I'm working with. And so that's been a really helpful thing that I can ask myself. So that's been a helpful point of self reflection for me. But yeah, we have a lot to do. And like, there's a pace that we have to keep up in order to make that happen.

Leanna Laskey McGrath  5:59  

What are your thoughts, Erica?

Erica  6:00  

I would say I agree with Jen, and how I think they both show up into different spaces. So if I'm at home, obviously, with kids, speed is important. But also like helping them learn in helping you around the house it takes you have to help them learn it and teach them and that takes too long. And then before you know it, it's you don't have time, and you're not doing anything at the end of the day. So that's part where it shows up there. And then the whole, like, I don't like the quality, it's up to my standards, sometimes that shows up more in work, or organizations that I that I volunteer with, or any types of groups that I lead, it kind of shows up, like if I'm the leader on it, it reflects on me. So I want to make sure that it's done the right way the first time. And I also don't have enough time to have it like show up in a not the perfect way. That's kind of how it shows up for me those two different spaces.

Leanna Laskey McGrath  6:53  

Yeah. And it's, it's interesting, I think, what I, whenever you said, I don't have enough time, it's interesting how our brains do this thing where it's like, I don't have enough time to show someone else how to do it, and then correct them if they do it wrong. But I do have enough time to do everything. How is it showing up for each of you now, in terms of your kind of challenges with delegation, and you know, what's what's most present for you all in your current situations?

Jen  7:26  

I think for me, currently, I've come to a point where I realized I can't do it all. And I need to be able to delegate some of this to other people. And I was thinking about this on the way to our call this morning as I was in the car. And it feels so rewarding when you have someone do something, right. And they're an extension of yourself. And you're like, wow, I didn't even have to do that. Look how good it is, you know, but I've been trying to lean in on enhancing my coaching skills, because I can't do it all. And I'm at this point in my career where maybe I won't be in as much of an execution mode as I have been the last 10 or 12 years. And I might be more in a delegation mode. And so that requires this shift in how I approach people and how I approach projects and things. So that's been something that I've been processing through, like, how do I equip people to have that trust there with them to delegate?

Leanna Laskey McGrath  8:24  

And Jen, you said, it's rewarding when it goes really well? What is the opposite of that? How does it feel when it's doesn't go when you're not super impressed with them? 

Jen  8:33  

Yeah, I think it creates stress, it's like, okay, well, this was a decent start. But now we've got one more thing on the plate, you know, and when you delegate something, it feels like hopefully, I'm I'm taking this off my plate and then to have to add it back on almost feels like 2x from what it was originally because now we've got something else started that we have to unwind and then rebuild, which is time consuming.

Leanna Laskey McGrath  8:57  

Yeah. I wonder if there's a way to kind of shift the thought there a little bit I wonder if there's an opportunity there. Because I hear you saying like, it creates stress, it's 2x the word and for example and then I get it because I felt this as well. But I just wonder if there's a thought that might be a little bit more helpful than oh god like now it's two times the work maybe it's like I'm laying the foundation or for less work later or something along those lines like and that's just what came to me maybe there's something else that you all are coming up with but I don't know something that is a little bit more like okay, this is like a loss leader this is an investment now for later something along those lines.

Jen  9:41  

I think stepping stones when I heard you saying that, like this is a stepping stone to something better and different later, it being able to see it from that perspective, rather than the immediate here and now.

Leanna Laskey McGrath  9:56  

Yeah, so more of kind of like that longer term thinking maybe like a short term hurdle or slow down for long term success. Yeah. Erica, what about you, how's delegation showing up for you,

Erica  10:07  

you know how everything is new, I'm starting a new business. And so everything is new to me. So in order to delegate, I feel like I have to understand it before I can delegate it so that I know number one, who to look for, and like, what to look for when I'm looking for someone to delegate it to. And then also what are those requirements and how to measure it. And so for me, it's kind of a foreign area where everything is new to me. So I don't know what I don't know sometimes. And like trying to find someone helped me with that. It's hard for me, it's like the chicken or the egg kind of scenario, like, and I'm never like, I'm not a fluff person. So it's like, even when I was in sales, I was always a person that had to know everything. In order to help people, I couldn't just fluff and pretend like I knew what just to sell someone I really wanted to help and understand, which was always like an impediment, like with sales, like there was always like a fault. Kind of like, Eric, you don't have to know everything. But to me, I felt like I could be more genuine helpful, if I can at least know and say what I didn't know. And so I think the same thing, it kind of goes into delegation, like, it'll be hard for me to just like, hire someone, I feel like I need to know as much as possible so that I can really tell them what I need versus just saying, do this work. And then you bring it back. And I don't really like the work because I didn't really have a clear guideline in the first place. Like, you know, I tried to figure out how to get someone to do something that I don't even know really know how to do myself, and like how to balance that and say, I don't know how to do it. So if that makes sense. It's kind of like weird.

Leanna Laskey McGrath  11:32  

Yeah, it's interesting, because I think what is coming up for me in your description is kind of like where the learning happens, or maybe when the learning happens in the process. So for you, you want all the learning to happen upfront, and no action can happen until all the learning has happened. Yeah. And I wonder for you, if there's an opportunity to kind of shift that our learning process is a little bit wider, and there's action along the way. So for example, like, we learn something like we learn a little bit, we try something, we learn a little bit more, we try something we learn a little bit, right? Like we iterate, iterate, iterate in that way, like there's action happening alongside the learning, instead of kind of having the expectation that all the learning has to happen. Like it's a prerequisite to action. Yeah,

Erica  12:27  

I think Leanna usually, in that scenario, I have a circle of people who helped me or I reached out to and they are there people that I know. So I can be really honest and say learning is I'm not fully there yet, Leanna. But this is where you can help me fill in the gaps. But that kind of limits me to other people that I may not know. And who could be more helpful to me, my circle is kind of small right now. Because those are the people I trust and say, Hey, I don't know I do this. I'm, you know, moving through this different iterations. But I don't know what I what I'm doing right now. So I'm kind of like in that circle, but I feel like I can be missing out on some more resources, if that makes sense. 

Leanna Laskey McGrath  13:05  

Yeah. And it sounds like maybe there's a thought or belief that that can only happen with people that you know, and trust. Why is that? 

Erica  13:14  

Couple of reasons. One is, I'm bootstrapping. So I am very cognizant of like how much money I'm spending for professional help. I feel like that's part of it. And then I think another part is wasting time, I think maybe the money and wasting time kind of goes hand in hand. Like if I'm hiring gin, I don't really necessarily know exactly what I don't know what I need, I'm gonna be wasting time I think in money too upfront.

Leanna Laskey McGrath  13:42  

So if I'm kind of summarizing this, it's kind of like your belief is if I hire somebody, the best way to use my money is to give them all the information before I ask them to do anything.

Erica  13:56  

So that I can have specific deliverables because I'm giving them paying them and, and I need to know exactly what to expect that I have done that, but I fumble through it with people that I that I know are more forgiving, more professional, but that circle is small. So that's kind of that's where it's showing up professionally.

Leanna Laskey McGrath  14:12  

What about personally, if you are comfortable talking about delegation at home?

Erica  14:17  

Delegation at home, I kind of understand like the learning that goes into it. So in order for my kids to be responsible, or to help me out with things I need, I know that there's been it's it takes time to teach them but that was kind of hard. I've gotten better just knowing that the time is going to take a little longer than it will take me to clean up the bathroom in 30 minutes or versus have my kids teach, you know, talk teaching my kids how to do it just kind of I know that it's going to take longer, but sometimes I don't have that patience or time because it feeds into professionally, my work. So have a little bit more of a handle on it.

Leanna Laskey McGrath  14:51  

I guess I'm curious about what thoughts you're using or what shifting whenever you are allowing a little bit more Time for things to happen at home, what is the thought that is helpful for you, or you to kind of allow your girls to clean the bathroom and be okay with understanding, it's going to take more than 30 minutes?

Erica  15:13  

I think I look at long term, I'm like, it's gonna happen, I think of like me helping them become adult raising kids, you know, I'm trying to make them adults, I think long term all the time with them. I've talked about this before, and how like everything I do their future. So it was easier for me to have that frame of thought at home, because I'm always thinking about 20 years from now, with the girls. It's interesting,

Leanna Laskey McGrath  15:35  

because I think that kind of relates to what Jen was talking about with kind of the short term inconvenience for the long term learning and success. And I wonder if there's an opportunity for you to kind of take any of those thoughts into your professional work?

Erica  15:53  

I definitely do you think I should think more long term? I think right now it's like I get like antsy, you're in the now you want to make every decision based off of this year, you can't really see long term for me, it's really hard for me to see long term beyond five years is kind of what I've been, it's really hard to to see that.

Leanna Laskey McGrath  16:11  

I'll let you sit with that for a minute. And I'm curious, Jen, what's coming up for you, as you're hearing Eric, as in our conversation?

Jen  16:19  

Yeah. A few things. One, like you may pour in all this effort. But unlike children that are yours to keep, there are employees who will move on after you if I ordered in this time in this effort and built out a workflow that makes sense for you and for them. And so I feel like I'm hearing a little bit of that from Erica, you haven't said that explicitly. But that's where my mind was going, as you were talking through, like I can understand some of this desire, maybe not to invest in somebody because there's not the trust that they are going to be there long term. I think that's something that subconsciously I bring into my conversations with my team in the way I approach different people is like, is this person, it's not right to say like, are they worth the investment? But that's kind of what I'm thinking, like, do I think that they're actually in this for the long term with me? Or are they just going to be moving on to the next thing in six months? And if so, then it's not worth the time. On my side.

Leanna Laskey McGrath  17:17  

It's interesting, Jen, because I think immediately what I thought is like chicken and egg, which one has to come first. And so for you, what you're saying is like, I need to know that they're invested, and that they want to stay here long term. And for them, it might be, I need to know that my boss is investing in me in order for me to decide to stay here long term. So I just wonder, you know, what the opportunities are there too, or because I totally get it. And that makes sense. You want to invest in the people that you know, are going to be there long term. And when you're trying to shift to a more long term mindset, then your kids who are you responsibility for life, or an employee that's going to be there for a long time and has shown, you know, demonstrated an interest in in that makes sense. So maybe it sounds like maybe that's where it's easier for both of you to think a little bit more long term in terms of like the investment. And I just wonder, maybe you don't need to, but I wonder about, you know, like, what's the opportunity to think about shorter term people? How do we then delegate to what our brains are categorizing is shorter term people?

Erica  18:25  

When I think of shorter term, I think of money. I think of me, I mean, I kind of see where Jen is going, spending time and energy into someone and you're not sure if they're going to be here a longtime, same for me, like if I'm looking for someone to hire, I would rather them to work with me long term. But I guess just trying to make maybe shorter term like projects, or just maybe I need Liana for this small amount of time and have like a very clear start in in maybe I should try, I could try that to see like how that makes me feel and just kind of maybe turn it around and find short term people to use for short term, like kind of breakout projects more of a short short term, because I think mine always goes back to I think, I feel like they're not going to be good quality in order. In order for me to delegate in my space. Now I need to know everything so that I can hire the right person to make sure I'm getting a good quality. And you know, not just anything, and I need to know what that looks like because I don't know what the quality will look like if I don't know how to do everything. That's that's how it shows. That's how it's showing up for me. And I feel like that people bring in good quality, you know, I feel like I can do better or not, you know, I want to find someone who's going to do it just as much as I can. Or someone who gives the energy as much as I can or still stays longer, you know, who's invested more longer term than short term. I think that kind of just it always kind of goes goes back to that but maybe thinking of shorter term projects, and maybe that'll help ease break it up a little bit more. I was thinking about short term projects. Can you hear me now? 

Leanna Laskey McGrath  19:54  

Yeah. And I'm wondering for you, Erica, and you too Jen, but I'm wondering if like if I think we have there's, there's a mindset of like it's going to take longer. And that seems to be a fear and a reason not to delegate. Right? Like it will, it will take longer. And I just wonder how we measure that. So like, in your example, Erica, are you measuring the amount of time it takes to learn, quote unquote, everything? And then it takes to find a person who has as much or more energy and enthusiasm as you and then how much time it takes to transfer the knowledge and then how much it takes to get it done? Are you measuring that amount of time versus let's try something mess up, fix it, try something mess up, fix it until you get to the end? It sounds like our brains are making this assumption that it's just gonna take longer, but like, do we have the data to prove that?

Erica  20:45  

No. And I have never been that type of person. And I always want it to be like that type of person. Just try it. Mess up, I am that person. But when it comes to like my own thing, I have not been an actually Liana, we think about it. Like I'm always like, scared of wasting money. But actually, time is money. It means not getting someone trying it and messing it up that could like you said, I haven't analyzed the data. But it could be more money of me like not getting someone to try it. Maybe that is wasting more more money. And I don't have the data to even show like any of that. So that is a going point.

Leanna Laskey McGrath  21:18  

Jen, I'm curious, where are you at? What are you kind of I see like your eyes going up, which usually means you're thinking about something.

Jen  21:25  

Yeah, yeah, I don't have the data either. I think when it happens for me, it's like very in the moment of I'm trying to get past this week to get to next week. And then I'm trying to get past that we're not in a way of like, I don't enjoy what I'm doing or I want this just hurry up and you know, move on to the next thing. But it's it can feel challenging to have so much like bubble up on onto my plate. Yeah. And that's the hardest part when the delegation doesn't work out is having it come back onto my plate when I thought, Oh, I thought we were going to be good with this. 

Leanna Laskey McGrath  22:01  

Makes sense. What's going on for you, Erica?

Erica  22:03  

I'm still thinking about like, how do you even get data? I think my I kind of stuck there. Like what, and I don't have the data for it. But I wouldn't even get the data. I mean, I guess just learning how to understand like my time and how it's spent would be a way, by contrast data just I'm just thinking about,

Leanna Laskey McGrath  22:19  

Well, right now, how are you making that determination that it's going to take more time?

Erica  22:24  

Which part take more time for someone else to learn, and then me hire them? And I am using like, previously, like, for instance, I used go a long time ago, I hired a hired someone to like a web developer, it ended up being so much money, like the communication was horrible. I mean, I wasted a lot of money that from that. And I learned a lot of that lessons. So I think that's where it stems from some losses that I've taken.

Leanna Laskey McGrath  22:50  

But it sounds like there were some gains there too, with the learning.

Jen  22:54  

For sure. Yeah, that's something that I'm processing through as I think about, like how I would get the data. I think, for me, it would be what are all those things that I've delegated? And if they come back to me, 50% done, how much time would that have taken me to get them to 50%. And like, that's again, even though we had to backtrack, and even though we had to take it from 50 to 100, or 75 to 100, there's still that amount that was gained, which when you think about your time, Erica, what is that worth? Is it worth the investment, even though you had to backtrack? And you know, for me in my role, it is it's worth it. I mean, it's not coming out of my pocket directly. But as I actually like, mentally make a list of all the things that I have delegated and have to delegate, just to keep things going. There is no way that I could do it. And so even when things are aren't perfect or not up to where we need them to be, maybe that's okay, because when you look at the reverse of like, what would be lost, had they not tried or not done the pieces that they did, what is that worth? That totally makes sense?

Leanna Laskey McGrath  24:06  

Now that's really interesting. It's like 50% is more than 0%. Right? 

Jen  24:10  

Yeah.

Erica  24:10  

It's so interesting. My husband has like a really good at his entire philosophy is more is better, like the more people in his circle is better. Like just he just wants addition. And I remember him like failing, kind of like not failing, but he ran for office, and then he lost the first time. But he had so many people helping him and he learned so much the second time, it was like easy for him. But his his whole idea in theory is like addition, like everyone can come in my circle and I'm like the opposite of that. But I see like how he is very competent at delegating. And it's almost like I can see how how the end gain is for him but also can see like how he doesn't know everything. And I'm always like, resentful, like you don't even know what you're doing but you're getting people to do it for you. And I guess I could learn from that. But it's like a against my purpose. Like my personality is so opposite of that. But I can see in real time how him just like getting someone to help trying messing up and then like messing up for a little bit. But then in the long run it works works out for him. Now that you say that, like, how much time does it take to kind of mess up? Or like, is it really worth it? If you kind of messed up a little bit? And then totally worth it like Jen said?

Leanna Laskey McGrath  25:19  

Yeah, yeah. And I think the other thing that I was thinking about when both of you are talking there is on top of the gain of productivity, like to the to the task, right? So on top of the 50%, in Jen's example of getting something done, what is learned there, right, like that's a gain to it's hard to measure, of course, but like, what do you learn? In the process of what do you learn about yourself? What do you learn about delegation? You know, what do you learn? In your example, Erica about like, how to do a better next time. So next time you run for office, it's only a fail if you stop at that point, right? And so what do you learn from that, quote, unquote, fail to make it into a longer term success? Those are gains two, totally, they are, as we're kind of wrapping up a little bit, just curious what you're taking away, you know, kind of what what are the biggest insights that you're having here in this conversation,

Erica  26:20  

I feel like something just like, like a light bulb is clicked for me. I feel like like butterflies almost like butterflies, because I feel like I am just try it. And I'm usually that type of person, like, just try it. And, but it's something that's so close to me, like my own company. But also like the learning I need to stay thinking about the learning games, like the growth mindset, when it comes to like, messing up at learning, like those things that may not necessarily equal like dollar amount. But those experiences that people get when they run businesses, and they know they grow because of the experience. And those are all things that are important to me that I kind of lost sight of,

Jen  26:55  

I think for me, I feel humbled in a sense, like I who am I to think that I can do all the things and there you have to delegate like it's, it's not even a choice. And so when I think about my team, and what they're doing and caring on a daily basis, like, I'm really talking about a 10 to 15%, of new initiative. You know, these are not the everyday things that people are doing, and they're great at and, you know, just rock stars in their role. But these are the new things that we're trying to gather. And we're learning together. And I'm figuring out what makes sense to delegate what makes sense to keep all that kind of stuff as we grow and change. But yeah, mostly feeling humbled in the fact that I can't do all the things and I shouldn't I shouldn't see myself that way. Because it's not accurate. 

Leanna Laskey McGrath  27:50  

Yeah, I think, obviously, we, we've all done amazing things in our lives and careers. And so we have a high level of trust in ourselves, and confidence in the work that we know that we can put out there. And there are also people out there who can do it better. That's a hard one for me to remember sometimes, too. But I think there have been so many times where I have in my career kind of delegated something, even not just in my career, but even to my four year old daughter, like, let's see what she does with it. And then, you know, an employee or my kid will come back with like something that I never would have thought of an approach that I never would have thought of, and maybe they found a way to do it even faster and better. And if I hadn't, like let go a little bit, and share that opportunity, I never would have learned, you know, and maybe it gets messed up, quote unquote, right, like, maybe it's not the way that I envisioned it, but we learned something in the process, and that we can apply to making something more efficient, or make right like it's like, okay, well, that didn't get done exactly how we needed it to. But like there was some really interesting thing that happened in the process of getting it done, that we can apply here to our future tasks that we need to get done. Awesome. All right. Well, anything else? Any final thoughts that either of you want to share? 

Jen  29:14  

This was great, thank you!

Erica  29:15  

It really was, thank you!

Leanna Laskey McGrath  29:16  

Awesome. Well, thank you both so much! This was fun. I'm glad that we got to do it. And thank you both for showing up!

Thanks so much for tuning in to the executive coach for moms podcast. Please like, subscribe or follow the show so you'll be notified when the next episode is available. I hope you'll join me again next time. Take care

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