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How High Achievers Can Learn to Delegate: Coaching Conversation image

How High Achievers Can Learn to Delegate: Coaching Conversation

E7 · The Executive Coach for Moms Podcast
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Last episode, Andrea asked Leanna about what she's doing next, and she shared that she's relaunched her business and is coaching high achieving working moms.

This week, we're featuring a coaching session she did with two very high achievers about a topic perfectionists and high achievers can ALL relate to: delegation. They discuss how delegating work to other people can be challenging because of concerns about quality, speed, trust, and more. But delegation — at work AND at home — is also *essential* to accomplishing everything we want to accomplish in our lifetimes.

Even if you feel like you’ve mastered delegation, it’s likely someone on your team or in your life is having some of the thoughts and challenges that these women share today, so please share this episode with them!

If you’re interested in a complimentary coaching session that will be featured on the podcast, please sign up here

Full transcript can be found here.

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Transcript

Podcast Introduction

00:00:08
Speaker
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.

Meet Leanne Alaski McGrath

00:00:19
Speaker
I'm your host, Leanne Alaski 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.

Business Relaunch Journey

00:00:37
Speaker
So if you've been following along, I just finished up my three-part series with Andrea, who is 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.
00:01:01
Speaker
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

The Delegation Challenge Begins

00:01:16
Speaker
for yourself.
00:01:16
Speaker
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.
00:01:45
Speaker
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.
00:02:01
Speaker
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
00:02:21
Speaker
strategies and mindsets that they came up with to overcome that. Because if we're going to 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.
00:02:37
Speaker
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.
00:03:00
Speaker
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.

Coaching Session: Delegation

00:03:24
Speaker
Hey, Erica and Jen.
00:03:27
Speaker
I'm super excited to jump into talking about delegation because I know that's 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
00:03:41
Speaker
How would I kind of characterize like how they're coming at 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.
00:03:58
Speaker
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.
00:04:14
Speaker
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 going to have to teach them how to do it. And then they're going to do it. And what if they mess it up, then I'm going to have to go back and do it again.
00:04:30
Speaker
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 y'all's thoughts about this, I think Erica, your concern is probably more the quality. 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.
00:04:56
Speaker
because I know like perfectionism isn't as present for you 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's shown up for you all.
00:05:12
Speaker
Yeah, for me, 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 as
00:05:28
Speaker
He brought up a really good point that I'm able to ask myself now, like, do you not want to delegate 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.
00:05:49
Speaker
So that's been a helpful point of self-reflection for me. But yeah, we have a lot to do, and there's a pace that we have to keep up in order to make that happen. What are your thoughts, Erica? I would say I agree with Jen. I think they both show up in two different spaces. So if I'm at home, obviously with kids, speed is important. But also helping them learn and helping you around the house, it takes you have to help them learn it.
00:06:16
Speaker
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.
00:06:31
Speaker
or organizations 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 in those two different spaces. Yeah. And it's interesting. I think what I
00:06:57
Speaker
whenever you said, I don't have enough time, I was thinking about 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 what's most present for you all in your current situations?

Realizations and Reflections on Delegation

00:07:26
Speaker
I think for me, currently, I've come to a point where I realize 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.
00:07:47
Speaker
You're like, wow, I didn't even have to do that. Look how good it is. But I've been trying to lean in on enhancing my coaching skills because I can't do it all. 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. That requires this shift in how I approach people and how I approach projects and things.
00:08:15
Speaker
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. And Jen, you said it's rewarding when it goes really well. What is the opposite of that? How does it feel when it doesn't go when you're not super impressed with them? 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
00:08:40
Speaker
When you delegate something, it feels like hopefully 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. Yeah.
00:08:58
Speaker
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 work. And for example, and 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, now it's two times the work. Maybe it's like, I'm laying the foundation for less work later, or something along those lines.
00:09:27
Speaker
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 lost leader. This is an investment now for later, something along those lines. I think stepping stones, when I heard you saying that, like this is a stepping stone to something better and different later and being able to see it from that perspective rather than the immediate here and now.
00:09:56
Speaker
Yeah, so more of kind of like that longer-term thinking, maybe like a short-term hurdle or slowdown for long-term success. Erika, what about you? How's delegation showing up for you? 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 what to look for when I'm looking for someone to delegate it to.
00:10:24
Speaker
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 to help me with that. It's hard for me. It's like the chicken or the egg kind of scenario. And I'm never like, I'm not a fluff person. So even when I was in sales, I was always the person that had to know everything in order to help
00:10:46
Speaker
people, I couldn't just fluff and pretend like I knew 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 and helpful, if I could at least know and say what I didn't know.
00:11:03
Speaker
And so I think the same thing, it kind of goes into delegation. Like it will 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'm trying 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 brand.
00:11:32
Speaker
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.
00:11:48
Speaker
and no action can happen until all the learning has happened. 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,
00:12:13
Speaker
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, I think Leanna would usually in that scenario, I have a circle of people who helped me or I've reached out to and they are there people that I know that can be really honest and say the learning is
00:12:38
Speaker
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 how to do this. I'm, you know, moving through this different iterations, but I don't know 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.
00:13:05
Speaker
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? Um, a couple of reasons. One is I have like 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.
00:13:33
Speaker
Like if I'm hiring Jen, I don't really necessarily know exactly what I don't know, what I need. I'm going to be wasting time, I think, in money to a friend. 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.
00:13:56
Speaker
so that I can have specific deliverables because I'm giving to them, paying them, and I need to know exactly what to expect that. I have done that, but I fumbled through it with people that I know who are more forgiving, more professional, but that circle is small. So that's kind of, that's where it's showing up professionally. What about personally, if you are comfortable talking about delegation at home?
00:14:17
Speaker
Um, 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 the things I need, I know that there's when 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.
00:14:35
Speaker
in 30 minutes or versus helping my kids teach you know teaching my kids how to do it just I 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 I have a little bit more of a handle on it.
00:14:51
Speaker
I guess I'm curious about what thoughts you're using or what's 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?
00:15:13
Speaker
I think I look at long-term, I'm like, it's going to happen. I just think of like me helping them become adults, raising kids, you know, I'm trying to make them adults. I think of long-term all the time with them. I've talked about this before and how like everything I do in their future. So it was easier for me to have that frame of thought at home because I'm always thinking about 10 years from now with the girls. It's interesting because I think that kind of relates to what Jen was talking about with kind of the short-term
00:15:40
Speaker
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.
00:15:53
Speaker
I definitely do think I should think more long-term. I think right now it's like, I get, it's like, Nancy, 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 looking at. It's really hard to see that. I'll let you sit with that for a minute. And I'm curious, Jen, what's coming up for you as your
00:16:17
Speaker
hearing Erica as an ad conversation. Yeah, a few things. One, like you may pour in all this effort.
00:16:25
Speaker
But unlike children that are yours to keep, there are employees who will move on after you, if I poured in this time and 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.
00:16:47
Speaker
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 approach different people is like is this person is not ready to say like are they worth the investment but.
00:17:04
Speaker
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. It's interesting, Gem, because I think immediately what I thought is like chicken and egg.
00:17:22
Speaker
Which one has to come first and so for you what you're saying is like i need to know that they're invested in 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.
00:17:40
Speaker
or because I totally get it and that makes sense. You want to invest in the people that are going to be there long-term and when you're trying to shift to a more long-term mindset than your kids who are your responsibility for life or an employee that's going to be there for a long time and has shown demonstrated interest in that makes sense. Maybe it sounds like maybe that's where it's easier for both of you to
00:18:06
Speaker
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 in shorter term people?
00:18:25
Speaker
When I think of shorter term, I think of money. I think of me. I mean, I kind of see where Jana is going because I'm spending time and energy into someone. You're not sure if they're going to be here a long time. Same for me. Like if I'm looking for someone to hire, I would rather them to work with me long term.
00:18:41
Speaker
But I guess just trying to make maybe shorter term like projects or just maybe I need Leanna for this small amount of time and have like a very clear start and 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 break up projects more of a short term.
00:19:04
Speaker
Because I think mine always goes back to, I think, I feel like they're not going to be good quality. 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 they're going to be good quality and 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 how it's showing up for me. And I feel like that people bring in good quality. I feel like I can do it better or not. I want to find someone who's going to do it just as much as I can.
00:19:34
Speaker
or someone who gives the energy as much as I can, or someone who stays longer, you know, who's invested more longer term than short term. I think that kind of just, it always kind of goes back to that, but maybe thinking of shorter term projects and maybe that'll help ease. Break it up a little bit more.
00:19:50
Speaker
I was thinking about shorter term projects. Can you hear me? Yeah, and I'm wondering for you, Erica, and you too, Jen, but I'm wondering if like, I think we have, 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 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?
00:20:19
Speaker
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 going to take longer, but like, do we have the data to prove that? No.
00:20:46
Speaker
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. And actually, Leanne, I mean, think about it. Like I'm always like scared of wasting money, but actually time is money. And me not getting someone trying it and messing up that could, like you said, I haven't had the data, but it could be more money of me like not getting someone to try it. Maybe that is wasting money.
00:21:11
Speaker
more money and I don't have the data to even show any of that so that is a good point. Jen, I'm curious where are you at? I see your eyes going up which usually means you're thinking about something. Yeah, I don't have the data either. I think when it happens for me, it's very in the moment of I'm trying to
00:21:34
Speaker
get past this week to get to next week. And then I'm trying to get past that week, 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. 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. Makes sense. What's going on for you, Erica?
00:22:02
Speaker
I'm still thinking about like, how do you even get data? I think my, I kind of step there, like what, and I don't have the data for it, but how would I 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, but contrast data just, I'm just thinking about that. Well, right now, how are you making that determination that it's going to take more time? Um, which part take more time for someone else to learn and then we hire them. And I am using like,
00:22:31
Speaker
previously, like for instance, I used a long time ago, I hired someone to like a web developer, it ended up being so much money, like communication was horrible. I mean, I waste a lot of money from that and I learned a lot of good lessons. So I think that's where it stems from, some losses that I've taken. But it sounds like there were some gains there too with the learning. Sure. Yeah, that's something that
00:22:56
Speaker
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 at 50% done, how much time would that have taken me to get them to 50% and like that's a gain. 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
00:23:23
Speaker
your time, Erica, what is that worth? Is it worth the investment, even though you had to backtrack? And 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 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 aren't perfect or not up to,
00:23:52
Speaker
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.
00:24:03
Speaker
What is that worth? That totally makes sense. Yeah. That's really interesting. It's like 50%. It's more than 0%. Right. Yeah. It's so interesting. I have like my husband is 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 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. And the second time it was like easy.
00:24:31
Speaker
for him, but his his whole idea and 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 confident at delegating. And it's almost like I can see how how the end game is for him, but also can see like how he doesn't know everything. And I'm always like resentful like
00:24:51
Speaker
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 against my, it's like my personality is so opposite of that. But I can see in real time how him just like getting someone help trying messing up and then like messing up for a little bit, but then in the long run, it works out for him. Now that you say that, like how much time does it take to just 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 as what Jen said? Yeah.
00:25:20
Speaker
Yeah. And I think the other thing that I was thinking about when both of you were 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 too. It's hard to measure of course, but like, what do you learn in the process? What do you learn about yourself? What do you learn about delegation? You know, what do you learn?
00:25:49
Speaker
in your example, Erica, about like how to do it 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?
00:26:02
Speaker
to make it into a longer term success. Those are gains too. As we're kind of wrapping up a little bit, just curious what you're taking away, kind of what are the biggest insights that you're having here in this conversation?
00:26:20
Speaker
I feel like something just like, like a light bulb is lit 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 gains, like the growth mindset.
00:26:39
Speaker
when it comes to like messing up and learning, like those things that may not necessarily equal like dollar amount, but those experiences that people get when they run businesses because of the experience. And those are all things that are important to me that kind of lost sight of. 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,
00:27:08
Speaker
When I think about my team and what they're doing and carrying on a daily basis, I'm really talking about a 10% to 15% of new initiative. These are not the everyday things that people are doing and they're great at and just rock stars in their role.
00:27:27
Speaker
these are the new things that we're trying together 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. Yeah. I think obviously we, we've all done amazing things in our,
00:27:54
Speaker
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
00:28:05
Speaker
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've 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 and an approach that I never would have thought of. And maybe they found a way to do it even faster and better.
00:28:34
Speaker
And if I hadn't let go a little bit and shared that opportunity, I never would have learned. And maybe it gets messed up, quote unquote, right? 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 it's like, OK, well, that didn't get done exactly how we needed it to. But there was some really interesting thing that happened in the process of getting it done.
00:29:04
Speaker
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? This was great. Thank you. It really was. Thank you. 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.
00:29:24
Speaker
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.