She’s an entrepreneur who has led her company to a fair amount of success. After recently hitting a roadblock, she’s hired new talent and is looking to position her company for continued growth. Host Muriel Wilkins coaches her through how to adjust her leadership to keep pace with her growing business.
Further reading:
- How Do I Adapt My Leadership Style as My Team Grows?
- How Your Leadership Has to Change as Your Startup Scales
- As Your Team Gets Bigger, Your Leadership Style Has to Adapt
MURIEL WILKINS: I am Muriel Wilkins, and this is Coaching Real Leaders, part of the HBR Podcast Network. I’m a longtime executive coach who works with highly successful leaders who’ve hit a bump in the road. My job is to help them get over that bump by clarifying their goals and figuring out a way to reach them so that hopefully, they can lead with a little more ease. I typically work with clients over the course of several months, but on this show, we have a one-time coaching meeting focusing on a specific leadership challenge they’re facing.
Today’s guest is someone we’ll call Flynn to protect her confidentiality. She’s an entrepreneur and has led her business to a fair amount of success, but recently, she felt like things weren’t going as smoothly as they could, and she became frustrated with how effectively the company was running.
FLYNN: Basically, this started. I became aware of a need to change, and to be honest, it was a big birthday and it may coincide with what people call not a midlife crisis, it felt like a re-contemplation of things. And I realized, I was like, “Wait, I’m doing everything for everyone.” Me leading this company more looks like me cleaning up everyone’s stuff. I really took this all seriously. There’s a lot of things that need to be examined because I’m doing people’s work versus leading them to have their greatest success.
MURIEL WILKINS: Flynn even considered stepping away from the company, but while trying to sort out the issues she faced, she took steps to better develop herself and improve her leadership, and brought in some new team members.
FLYNN: I wanted to find stronger players. I actually worked with a headhunter and I filled some posts with stronger players. That was incredible because the type of people that came were very different than ones I had had in the past. The idea of where I was trying to get is really having people own their work. I have some great new people. Now we want to set this up for success, so I want to make sure I’m structuring my leadership in a new way where they’re doing their work. I’m not answering their questions so don’t come to me for everything.
MURIEL WILKINS: Now, Flynn wants to make sure she builds back better, putting her own leadership skills in check to avoid a situation where she can’t trust her team again. But first, I wanted to go back to the beginning to understand more about why she started her own business in the first place.
FLYNN: I’m from a world of entrepreneurs, so I’ve had businesses since I was seven on the bus making things that I sold to my friends, so starting a company is not something unusual, and everyone in my family is an entrepreneur. In my twenties, I had a job that didn’t pay very much, and on the side, I started a company which had a structure where I sold to clients that I had met during summer jobs as a student, and I did that on the weekends and it was very lucrative. That industry changed a little bit, and so I decided to go back to school. So I started, I went to design school. I did all the pattern making, did all the sewing, so that’s where we started. I’ve shifted as the environment has shifted, and it’s always been about quality and not spending money on things other than the quality.
We’ve developed ourselves into somewhat of a brand, but I’m finding that I probably need to invest in marketing now because I’ve been so under the radar that our clients come back and I’ve had most of them for the whole time we’ve been in business and we add, but we now need a new audience. And I’m not sure if I need to shift a little bit and look at where I’m spending my money, because I’ve gotten some coaches and they ask me to do things and I realized I’ve spent money there where I should look to myself as the expert. Like, “Why am I doing what you want to do?”
MURIEL WILKINS: Yeah, understood.
FLYNN: I need to be reading and figuring out what our core values are and go one step aside and do what I believe in. I give too much. I need to just stop all of that. I’m the boss and I actually know a lot, and I think I need to be more confident in my ideas, because I put money in these other people’s ideas and they really don’t know as much as I do.
MURIEL WILKINS: Yeah. Okay. All right, so we’re going to focus today on trying to figure out what your ideas are about the particular areas that you’re challenged with, and see if you can come to your own conclusions. I think that that’s a big part of coaching, is understanding what your answers are.
FLYNN: I’ve come to a lot of conclusions in basically writing down what I’m going to talk to you about and processing it and reprocessing it and reading these things, and it’s hilarious.
MURIEL WILKINS: Well, there you go. This might end up being a very brief coaching meeting.
FLYNN: No, no, no, no, it won’t, because we can take it, but I just kind of like, what can I do on my own so that what I do with Muriel is going to be very helpful?
MURIEL WILKINS: Oh my gosh. Oh my gosh. Okay, so now, it sounds like what’s happened is there was a period in time where you were finding some challenges with some of your team members. Those team members are no longer there. You now feel like you have a pretty good team or a very good team, and so the question is… Well, what’s the question as it relates to your… If you could say it in a one sentence question, what’s the question as it relates to your current team?
FLYNN: I think that there is still some repositioning of responsibilities where I see weakness in characters. How much do I have to worry about what they’re learning and getting? Has this environment really changed? Do I need to do the KPIs and what their goals are personally as well as the corporate goals? Because I feel like coming out of this experience, we’re in a whole new world of what people consider work to be.
MURIEL WILKINS: Consider work to be, okay. And so what I’m hearing from you is in what ways do you need to adapt, if any?
FLYNN: If any, and I think I’ve come up with some things. I want to hear if you support those or think that I don’t need to go that far.
MURIEL WILKINS: Well, let me caveat that. Whether I support it, it’s very interesting because you just said, “I am paying all these people to give me ideas and I have to come up with. I realize, no, I know what’s right for my company and I can come up with my own answers.” And a few minutes later you said, “I want to know if you support those ideas.” So I think we’re going to, during this conversation, actually put into practice what you shared a few minutes ago, which is it really doesn’t matter whether I support the idea or not because I’m not the one running this business. You are. What we’ll do is maybe work through what your different options are, what are the different ways that you’re thinking about it, and are you coming to a conclusion or are you getting to a decision that is aligned with ultimately what you want for your team and your business? Because that’s all really that matters, is is there alignment? Are the decisions that you’re making aligned with what you want the outcome to be?
FLYNN: Agreed. And another thing that I’m really doing is trying to take control of my future, shall we say, because I think sometimes I’m going to have to be bold and do things that are uncomfortable. It’s my job to restructure things for success for the company.
MURIEL WILKINS: Okay. So let’s take a step back, because what I heard you say is in what way do you need to lead any differently than you have? Do you need to lead a new way so that it adapts to the team that you have? Am I phrasing that right?
FLYNN: Mm-hmm. The leading in a new way really has to do with I used to finish people’s job and be very hands-on, and now I’m leading in a new way and telling them their responsibilities, setting KPIs and speaking to them about their successes, and also asking questions to try to get them to answer so they can grow and become independent in their work. And that’s been working very well. And also, I’ve been giving a lot more responsibility to people instead of micromanaging, and in fact, I’m finding that some people have a lot more talent than you realize and a lot more capabilities, and you also find that some people don’t.
MURIEL WILKINS: Right. Okay. So what do you do in the situations where they don’t have the capabilities?
FLYNN: Exactly. What have I done? I tried to do a KPI review. I have not utilized that with all of my team, only where I saw issues. I think that I need to insert KPIs and speak to everyone at a certain cadence to make sure they’re growing and the company’s moving forward, which takes more work on my part to decide what they are, but I think I’m going to have to start putting that into action because the company’s stalled in growth a little bit, and I think they haven’t held people accountable enough.
MURIEL WILKINS: Okay. All right. So I think there’s an underlying question here, which is how do you set expectations and hold them accountable to those expectations with consistency and proactively, rather than wait until there’s a problem to then hold them accountable retroactively?
FLYNN: Agreed.
MURIEL WILKINS: Okay?
FLYNN: That’s a great question. So, I think I need to spend time really outlining what success looks like in each position, which I have started to do. Where people are really performing to a high level, I guess the answer is I still need to do that. Correct?
MURIEL WILKINS: Well, let’s work through that. What do you have to gain and what do you have to lose by doing that across the board, regardless of what the current performance is in that role?
FLYNN: Thinking of one role, what you have to lose is that if someone really seems to be at a high level and I’ve been really happy with this person, I don’t want them to think I’m being overly judgmental when they are doing a very good job.
MURIEL WILKINS: And in what way are setting KPIs or setting expectations judgmental?
FLYNN: Maybe they’re not actually, because this person would like to know that they’re having success, so talking about the amount of sales coming from their work or the successes of different people, upon thinking about it, they would probably like that. I guess my thought was they might think I was judgy in a creative field, but I think you’re right. The person’s a professional, they really wouldn’t care.
MURIEL WILKINS: Yeah. You’ve articulated the thought and I don’t know if that thought really serves you, right?
FLYNN: It doesn’t serve me.
MURIEL WILKINS: I only share expectations, or I only share whether it’s in the form of KPIs or any other way, or I only give feedback if the person’s not doing a good job. Is that necessarily true?
FLYNN: I share feedback on a more casual basis if it’s a good job, so I only hold meetings about these things when disaster is starting to occur.
MURIEL WILKINS: Got it. So, systems and processes don’t come into play unless.
FLYNN: A little bit, because if you’re going along well, you’re saying what they’re doing well as you go. It’s just I think the hard conversations, I think, I may be not be good at the hard stuff, so it piles up a little bit and then it becomes a more serious meeting. Does that make sense?
MURIEL WILKINS: Yeah. I think it sounds to me that if I was a casual observer in your company and walking around the halls and hung around for a little bit, is that these conversations become an event rather than-
FLYNN: The hard ones.
MURIEL WILKINS: Right. But the fact that you’re labeling them as hard rather than saying, “These are just conversations we need to be having consistently about what the expectations are. How are we meeting expectations? What’s working, what’s not working?” And keeping track of that. If that is happening consistently, it’s not a hard or easy conversation. It’s just a normal conversation to have, which by the way is what leads to holding people accountable.
FLYNN: I tend to keep track with numbers and Excels add then, comments on them, and then I think I should be sharing that information with the people, the different members of the team. So if I’m keeping track, to me, it looks more like a monthly meeting where you’re going over successes and areas of working too, because I’m writing it down somewhere, if that makes sense.. Versus casual, that was successful, good email. It should be more numeric and trackable.
MURIEL WILKINS: Flynn started her company at the ground level, and in part, because of that, she’s run into some of the pitfalls and ambiguity that comes with entrepreneurship, especially as the company grows. While she originally came to the coaching session with issues around underperforming employees, she was ready and willing to think about ways she could take responsibility for that performance and create better systems in the future. That’s a good first step, the desire to take accountability and to put in the work of thinking through ways to improve. In some ways, this is just a small slice of an issue that happens with so many leaders, being able to back away from the day-to-day crises, focusing on the product and services you’re selling, and thinking about how you can really scale up your leadership.
Sometimes as an entrepreneur, it’s even easier to stay in the weeds of doing the work yourself because you know it so well, and building systems to manage people can be really tricky. But Flynn is ready to take the first steps towards creating a better system, and while it is just one part of the issue she’s facing, I think it’ll be helpful to talk through it a bit more in depth to have her test out why and how she might move forward with a different kind of approach.
What it sounds like is in your mind, you are thinking, Oh, if everything’s going good, I can keep it casual, and if things aren’t going good, I’ve got to create a process and structure. And maybe in the spirit of what you said, how do you need to potentially structure your leadership in a new way? Maybe the new way is that there is no, This is what happens when things are good, and this is how I deal with things when things are bad. It’s more around how do I ensure that I am managing performance and managing deliverables consistently, and therefore, I’m having these meetings and I’m keeping track and I’m sharing feedback one way or the other with a regularity across all of my team members, regardless of where they are?
FLYNN: Yes.
MURIEL WILKINS: What difference do you think that would make for you and for the team?
FLYNN: For me, I think it would be taking a bit more time to reflect and setting up structure around each person’s position, which is fine. And for the team, I think it creates a bit more equitability in my interaction with each of them because if I’m pulling people in who are not having success to go over and try to boost them and help them improve, then it feels like they’re being pulled into the teacher’s office a little bit, when if people are successful, I’m not having the same time with them in a formal meeting.
MURIEL WILKINS: So, it becomes an expectation of you in terms of the way that you lead them?
FLYNN: Yes, but I can see the success of that already. I also do think that me restructuring someone who’s not having success leading is an obvious thing to do, so I need to be comfortable shifting people’s positions as appropriate.
MURIEL WILKINS: And what is your level of comfort with doing that now?
FLYNN: I’ve been moving forward with that quite a bit recently. So if you had spoken to me last year before I had done all of this work, I would not have