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High-performing women often have more barriers to overcome than their male counterparts, both internally and externally. To support their professional growth and to improve your own business, you need to understand what might be keeping them from leveling up and make sure they have the resources to succeed.

This week we talk to business coach Jodi Flynn of Women Taking the Lead on how to best nurture high-performing women.

Rich Brooks: Our guest today is an executive leadership coach, podcaster, author, speaker, and workshop facilitator. Women leaders hire her to develop the skills needed to thrive in senior leadership. She is the host of the critically acclaimed Women Taking the Lead Podcast and an Amazon bestselling author with her book, Accomplished: How to Go from Dreaming to Doing.

She is the President of the board for the Maine Women’s Conference, and has been featured in Entrepreneur and Forbes magazine. We’re looking forward to diving into what owners need to know about working with high performing women with Jodie Flynn. Jodi, welcome to the podcast.

Jodi Flynn: Thank you for having me, Rich and Yury. So good to be here. I’m honored. Really honored.

Yury Nabakov: Jodi, we are excited to have you and we have a big agenda for today. Actually, we’re going to unpack it throughout this conversation and let’s start with the basics. I want to know, you work with a lot of successful women as a coach. So how did you find yourself in this role and why did you choose this specific segment? Why women?

Jodi Flynn: Oh, that’s a great question. Because when I started my business I was actually coaching women and men. And it was more focused around businesses and the workplace and who these business owners were as leaders.

And I enjoyed working with men. I mean, men are straight shooters, which makes me laugh. They say it like it is, whatever they’re thinking, they’ll tell you they won’t hold back. And women, it can be a little bit different. But what I found with men is, they didn’t want to go into the emotional side of things as much. And when I was working with women, it almost felt like a calling.

I started working with women who were incredibly talented, capable, hardworking, but they were filled with so much self-doubt. And so like these standards for themselves that they just couldn’t meet that it started to feel like a calling. Like I really, my heart went out to these women. And I was one of those women. I know I’m smart. I know I’m talented. I was working really hard, but it never felt like it was good enough. I always had to do more to prove myself, and it took a lot to overcome a lot of those tendencies to go easier on myself. And so I really wanted to help these women because you can be highly successful without having to work so hard and take so much on yourself.

Rich Brooks: That makes a lot of sense. And I know you’re talking about other men because Yury and I are both very emotionally open and available. We just want everybody to know that. I cried at Guardians of the Galaxy 2. We’re open and emotional kind of people. But I know what you’re saying. Traditionally, especially men perhaps in Maine, have this sort of thing about being straight shooters and not necessarily being emotionally available.  I hear you. I feel you. I see you.

All right. You talk about three common struggles that high-performing women often have. And the first is that the idea that the high performing woman says, “I know what I need to do, but I’m just not doing it.” Now on this show, I know you’re working with these women, on this show we usually approach things from the owner or the leader in the company. So putting those shoes on Jodi, how might you approach helping this person with this struggle if you were their manager or the owner of the company?

Jodi Flynn: Right. So typically what is happening with, “I know what to do, I’m just not doing it”, is a person who has gotten the training or they see the value in changing their behavior. But when push comes to shove, they just are struggling with implementing that new behavior. And there are a couple of things that are going on with this.

Sometimes it’s just as basic as they need accountability, they need support. They need someone to be checking in with them to make sure that they’re doing these things. And especially people who are externally motivated, and I am. And if somebody is a people pleaser, they are externally motivated. They do want to meet your expectations. Just having accountability will help them.

The other thing is, and I’m going to mention a book, Rich, that I know you’ve read because you’ve mentioned it before, Atomic Habits by James Clear. One of the things he talks about in his book is it is extremely difficult to change a behavior if your identity goes against that behavior. You need to take on the identity that is in alignment with the behavior.

So for example, and I believe he uses this in his book, if you see yourself as a cigarette smoker, it is going to be really difficult to quit smoking because then you’re telling yourself I’m trying to quit smoking. But what is more powerful and more effective is to take on, “I do not smoke cigarettes, I am not a smoker”. And then your behavior, it’s easier to then align your behavior to your identity. So the point I’m making is, identity is stronger than behavior. So if you’re trying to change a behavior but it conflicts with your identity, you’re in a struggle. So to get at the heart of this and what I work on with my clients, is changing their identity so that they’re in alignment with the behavior.

So I’ll bring it to an example that I would use with one of my clients, because this is very common. The practice of delegating and sustaining that delegation, not taking it back because the other person isn’t doing it exactly the way that you want to do it. Oftentimes my clients often struggle with giving away tasks that they see as highly important or client facing. The stuff the client is going to see, they have a hard time delegating that work. Now, if their identity is “I’m the doer, I’m the problem solver. I’m the one who saves the day, they’re really going to struggle with passing something off. But what we work on is changing their identity to, “I’m the person who develops leaders. I help other people be successful. I help other people shine when they take on that identity.”

And my client one time had a physical reaction when we talked about this. She’s like, “Oh my God. Yes, that’s exactly it. I want to be the person who develops other leaders.” And it was there she had a conversation with their team and it just started flowing because now the behavior she wanted to take on was in alignment with her identity and how she saw herself.

Rich Brooks: if I’m hearing you correctly. So if I have one of these people on my team. And just to get back to the original struggle that they have,” I know what I need to do, but I’m just not doing it”. It sounds like what I need to do is understand how she sees herself and what is intrinsically who she is, and if that’s not in alignment – which she needs to do – we need to have a conversation around that so maybe I can help her see how she should be looking at herself.

Like you said in this case, it might be delegation and other cases, it may be something else. But to ensure that she understands who she is within the company, perhaps, and who she is in general, that’s going to make those changes easier to implement.

Jodi Flynn: Absolutely. You want to get at the heart of how she sees herself and her role within the company. So asking questions, like, “What will it mean if you were to do this?” And getting back to that feeling place, how would you feel if somebody else were to take this on, and that sort of thing. You definitely want to get at the heart of that mentality.

Yury Nabakov: What if the person who you’re mentoring or coaching or basically trying to get to the heart of their identity, is not necessarily willing to share because they’re way too private, even though they may recognize the benefits of that type of self-assessment and self-discovery? Like, how do you get to that territory?

Jodi Flynn: Well, with my clients it’s a process that starts from the first touch point, even in my marketing. I am marketing myself as somebody who is trustworthy, reliable, non-judgmental, that approach. And then from the first consultation call when we’re talking about, okay, what’s going on in her world? Why is she looking for a coach? You know, how would we work together in the whole process? It’s building trust with that person, because there are some people who are more private than others. There’s nothing wrong with that. That is just kind of how they navigate the world. It’s just their nature. So it’s my job as their coach to build that trust level, to be non-judgmental and to provide a safe space where they can say anything.

And I am very conscious of sending cues – explicitly or implicitly – of, hey, say what’s on your mind, come as you are. I’m not going to judge. If you want to swear, you know, whenever I hear somebody say, “I’m trying to think of how to say this”, I’m like, say it the way you’re thinking it. I’m not going to judge you. And oftentimes we’ll laugh. And I think laughter provides that safe space to where ultimately they realize, okay, I can tell you this. You’re not going to judge me and it’s not going to go anywhere.

Yury Nabakov: Because the way I look at it, it’s a two way street. It’s a recipient of the message that I want to get to kind of like to the bottom or to the core of their identity. But, but then, from their point of view, what if they’ve never engaged in those types of conversations and out of nowhere, I’m like, “Hey, show me what’s on the inside.”

Jodi Flynn: Well, what’s your deepest fear, right?

Yury Nabakov: Exactly. So I’m just kind of curious how can I prepare myself as the leader to be more willing to be in that position, even though I may recognize that I may not want to do it because it’s something that is alien to me? But also, what steps I should be taking in easing that conversation or easing that mindset to start developing between me and my employees or my direct reports?

Jodi Flynn: Yeah. That’s a great question. And you have to have built rapport with your team, your employees. You have to have that open dialogue conversation. So, no, you’re exactly right. This isn’t a conversation you can have with somebody where you’re like, “What’s your name again? And let’s get at how you see yourself in the world and how you operate.” It goes back to the reason why you asked that question, Yury, is you’re curious. So what I say to people is rather than worrying about what questions do I ask or what do I say, take on a state of being and a state of mind that’s like caring and curious, and interested. If you’re caring, curious, interested, nonjudgmental, and they trust you to keep this conversation confidential. That’s vitally important as a business owner, a team leader, you keep these conversations confidential. They will over time open up more and more. But you have to have small wins before you can have the big win.

And luckily, I’m able to build that with my clients so that they can get to the point where they just say it like it is, to the point where they may even reveal things about themselves that they could be judged on. That may make other people think they’re a horrible person. You know, those things where people say like,” Oh, I’m going to say this and I’m going to sound like a horrible person.” But they’re able to just say it. But when they’re able to say it and tell the truth about how they see things, that’s when we can make a difference for people.

Rich Brooks: I also think there’s a difference between what you’re doing Jodi, because you’re coaching people, and at the end of the day you can’t fire them. They actually can fire you. It may be tougher for any employee, but especially maybe women, in a situation to feel like they can open up to a boss, especially if that boss is a man. And I think that’s really something that we have to be as leaders, we have to be very aware that we sometimes can intimidate the people underneath us that may feel that, “Oh my gosh, that person’s name is on my paycheck every week. I can’t be as open, as forthright.”

And it’s been my experience because, I’ve been at this way too long, is that being vulnerable yourself and sharing something that might be embarrassing or telling about yourself is certainly one step towards building that deeper relationship where you can have more of those important conversations that really can change the trajectory of somebody’s life and career. But you have to be willing to embarrass yourself and be able to make fun of yourself as well. And so, because it can be tricky when you are the one who’s writing your name on somebody’s paycheck for them to open up and tell you that they feel like they’re unworthy or they’re a fraud or anything like that.

Jodi Flynn: Absolutely. And you know, I’ll use this example even though it’s not in the workplace. I have a friend who, at this point in our friendship, I love and adore and can say anything to her. But when we first met, I felt like I had to sit up straight when I was around her because she never swore, she never said anything inappropriate. She almost seemed too unbelievable, too kind. And you know, as human beings that’s suspicious. It’s like, what’s the deal here? Like, is this PR can they let their hair down? So, you know, you’re on guard because they’re behaving so appropriately you feel like you have to behave appropriately.

And eventually this friend finally dropped an F-bomb and I was like, “Oh”, I even said out loud, “Thank God”.

Yury Nabakov: I would expect you to say something different.

Jodi Flynn: But it let me know, okay, this is a human being who has flaws, can get upset, and has that underbelly, that emotion. And I felt like I could be more myself and share more of myself with her. Now, as a boss, there’s a certain level you’re going to maintain. It’s not going to be like interacting with a friend, but you can show your human side. Share stories about when you were up and coming in your career and the mistakes you made and what helped you and that sort of thing. That’s very helpful, that lets us know that our leaders are human, they weren’t born this way, they developed this way. Because we can have this assumption like, “Oh Rich, you’re just really good because you’ve always been really good at this. You’re always this intuitive and you have this great understanding about clients and the market and employees”. When the reality is, it was from making mistakes and learning from your mistakes over time that you’ve gotten to this place. We just assume if we don’t know the background story, that someone was just innately this good. They know when to bite their tongue. They know when to speak up. But no, those are things that we learn over time. So by revealing some of our own mistakes, some of our own flaws, it helps people open the door to having those conversations around, “Okay. I’m struggling with that, too.”

Yury Nabakov: I like what you said about being human. And in a lot of situations where we think about high-performing individuals, it feels like they have this notion of, “Oh, I got this. They’re not going to go ask for help. They don’t need anything. They’re like the superhuman, they know their answers, and they know what needs to be done. And if they just put in extra time they will get where they want to get.

But do you have any recommendations for managers and the leaders, how can they encourage those high-performing individuals to be more like us, more human, and ask for help when help is needed? Or maybe even how can that individual recognize that there is an opportunity to ask for help?

Jodi Flynn: And I want to make a distinction, and it’s a little bit of inflection here. There’s a difference between the confident, “I got this!” Oh yeah, I got this confidence. And the person who’s like, “I got this”, rejecting all help, all assistance. Like I got this. Right. And, you know, for the leaders of these people, what’s really important is modeling. You’re asking for help. You’re asking for assistance. You’re accepting help when help is needed. Guiding them to realize they don’t have to do it all on their own. And typically a person who has that mentality of, “I got this, I can do it on my own”, there’s things going on there. There’s an insecurity, even though they’re high, they’re probably one of the best people on your team. There’s this insecurity that if I asked for help, it means I’m incompetent or incapable, or I wasn’t the person I was supposed to be for this role, this job, I don’t deserve it.

So modeling that even as the business owner or high level person in an organization that you asked for help, you get guidance, that sort of thing. It makes it okay. It normalizes asking for help.

Yury Nabakov: Awesome. Thank you.

Rich Brooks: The third thing that you brought up was a novelty to me when I first heard of it. And it’s the person who says, I’m afraid of taking on more work or bigger projects because I’m afraid to fail. What does that look like and how might a leader help a person struggling with that?

Jodi Flynn: Right. And you know what, typically you’re not going to hear them say this, and that’s probably why this is novelty Rich, because this is a deep, dark secret. A lot of high performers, when they have a sense that they’ve plateaued, “I’m at the highest level I can manage and I’m already making sacrifices to my health, my family, a whole bunch of things are taking the hit because I have to invest so much energy to be highly successful here. I don’t want to take on more because I’m afraid that will be the death of me.”

I even had a client say, “If I accept that promotion, in three years I’ll be dead. I will be dead because I’m already giving up too much and I’m already sacrificing so much.” So there is this, but they won’t say it out loud. Instead, if a new project is offered like, “Hey, I think you’d be great for this”, or there’s a potential other promotion coming up, they’re going to deflect and try to keep it a secret that they’re barely holding on. Because again, their identity is, “I am the high performer. I am the person who delivers. I am the person who can save the day and solve the problems”. But now they’re stuck. Right? And they’re stuck and they’re falling into the other traps. They’re not asking for help. They’re not doing what they’ve been trained to do. And so it becomes this vicious cycle, and if they don’t break it, they will spiral down and become more unwell.

Yury Nabakov: Clearly I’m not an expert in this area, but I’m listening to your insights and it feels like a lot of people get boxed into this very narrow vision of what success is. And it’s purely from the output related to your career or your job. Because when you actually strive to achieve balance. And when I say balance, it doesn’t mean that you equally apply yourself to your family, your social life, or your career. When you truly identify the priorities and you can manage those priorities that are related to your vocational and financial needs, then we can start talking about the successes. But again, it may just be a very limited belief that I have when it comes down to career and the successes. But who knows, maybe I’m just too young and I haven’t experienced life the way that people did.

Rich Brooks: He’s calling us old, Jodi, I don’t know if you noticed that.

Jodi Flynn: I chose to ignore it, Rich.

Rich Brooks: I can’t, I can’t let it go. 

Jodi Flynn: You’re correct, Yury. That a lot of, I mean, this isn’t just women. A lot of people just in general lay success on the external indicators of success, the measurements, how are other people doing, the comparisons, what I’m supposed to have achieved by this point in my career. I mean, I think a lot of business owners can relate to the expression of, “I thought I’d be further along by now”. Right? Because there’s this story about what milestones you’re supposed to hit at year one, year five, year 10, you know, and all of those things.

And you’re exactly right. Getting more in touch within an internal indication of success, of am I living according to my values. How fulfilled do I feel, am I checking the boxes of feeling close to my family, to my friends, is more of my life getting attention? Because I’ll tell you, at one of the most successful points in my career, I spent the weekends resting up on the couch, because I was so exhausted from giving so much to my job Monday through Friday and sometimes even hours on the weekend, too. That if I got the laundry done, I got a workout in, I was fed and I showered, that was a successful weekend. I was ready to go on Monday to give it my all, all over again. And it got to the point where when people would want to make plans on Friday night I was like, I can’t do Friday nights. Because I would be utterly exhausted at that point.

Rich Brooks: Jodi, I think a lot of high performing people, women especially, they don’t want to be seen as weak. And I think that there’s a lot of owners and leaders out there who are like, as long as my people are performing, I have no problems with them. And it’s only when something becomes so evident that we have to step in. Obviously this is not the best way to run a business in 2020. In this day and age, I like to think that we’re a little bit more evolved than this, and we understand work/life balance and those kinds of ideas.

So if we’re not going to hear from our team that they’re struggling with some of these issues, what are some of the signs that we might see that would help us identify this? And then how can we kind of interject ourselves to make sure that they don’t burn out, as it sounds like you almost did back then?

Jodi Flynn: Yes. And I think it goes back to the question Yury asked about how do you get to that point where you can ask this question or have this conversation. It’s have regular check-ins, build rapport, ask them how they’re doing. You know, not just how’s that project coming along, but like really, how are you doing?

And I’m going to go back to modeling again, too. Model taking breaks, model taking days off, model taking vacations, because there’s what our leaders say. You know that they want for us, like, “Hey, I want you to be happy. I want you to be well rested. I want you to be able to enjoy your personal life”, and then there’s what our leaders do. And if our leaders are not modeling that behavior, we’re going to go, “Well, what they say is this, but what they really want is for us to behave like they behave”. And as leaders, sometimes we lose sight that people look to our behavior more than they listen to our words. So we have to model that behavior, check-in, provide that accountability, have those conversations.

But I will say this. If it gets to a point where you’ve hit your limit, because like you said earlier, Rich, it’s a different dynamic that I have with my clients that a boss will have with their employee, because I’m hired by them. They are my clients. And so the dynamic is a little different in some regards to there may be only so much you can do. And at that point, I would say, if it’s possible hierarchical for them or ask them if they’re interested in having a coach hired for them that can work with them all in all this stuff.

Now I will say all the recommendations we’ve given up to this point will help the majority of people. But there may be a few cases where someone is just struggling or the leader is like, this is beyond me and beyond what I’m capable of, and that’s when you need to bring in a professional. And it’s very common for companies to hire me or other executive coaches like me to work with their people to get that added layer of support. Especially for people that you don’t want to lose. You know that they’ll be a great asset to your business for years to come, but if they’re burnt out, you’re not going to get a lot from them.

Yury Nabakov: Jodi, you talk a lot about different dynamics that play a critical role in the way high-performing people are being managed. Has the process of managing high performing women changed during COVID due to all the changes in the dynamic; working from home, remote learning, there are so many new things that we may have not experienced or even entertained as an option and now it’s just, it’s here, what’s happening. So any thoughts, ideas, insights where we are and what we should do with our high performing women or in general employees who are in that new reality?

Jodi Flynn: I think this is the heartbreaking question, right? Because in September, record numbers of women completely left the workforce. These are not numbers that include people who are on unemployment, who are seeking work. These are women who willfully took themselves out of the game because of the pressures put on them to take care of their families and have a job. They’re just playing too many roles and there’s only so much a company can do to help these women.

Now I have seen some changes, especially in my clients that they’ve been making for their team members who have young children or school-aged children or aging parents and have to do double duties. And as much as, God knows as much as men have really stepped up their game in terms of sharing the workload at home, the reality is the majority of the burden is still on women to do that, to play those roles.

But what I’ve seen my clients doing has really helped them in their businesses, is being more flexible with the hours and when the work gets done. So it’s not, you know, you’re on the clock at nine till your lunch break and then you’re on the clock till five. It’s other than client meetings and this deadline, the work can get done at any point in between. They’re also investing in systems and processes that make what they do in their business more efficient, so not as many hours are required of their employees to provide high value work. And I think sometimes we equate hours with value, and that absolutely is not true. Because if you look at most offices, the amount of breaks that people take in an office is outstanding. You know, I think one study I saw said in an eight hour day, an employee will perform about five hours’ worth of work.

Yury Nabakov: Four.

Jodi Flynn: Four or five.

Yury Nabakov: I know exactly what you’re referencing. That was a very interesting,

Jodi Flynn: So why do we make people lock into an eight hour shift when they take intermittent breaks. And as someone who works from home, doing the laundry doesn’t feel like a chore when I want the break anyway. It’s just, I’m doing something different. And then I can come back to my desk refreshed and continue to do good work.

So we want to look at what is the value that each of our employees provide rather than how many hours are they clocking. So reframing the value that an employee brings to a company can help these women as well, because if there’s less pressure on them to work an eight hour shift between 8:00 and 5:00 or whatever those hours may be.

Because this is the thing with these high performing women, they don’t want to fail. They hate failing and it hurts them. They would rather take themselves out than be a failure. They would rather avoid trying something new than be a failure. Now is this something to work on in their mentality? Absolutely. But can we support them with where they are right now and help them to feel and be successful within these organizations while we’re going through a pandemic? Because wouldn’t it be great to still have your female employees at the end of 2021?

Yury Nabakov: This is a fantastic insight, Jodi. And I think a lot of listeners, especially managers – regardless of their gender – should take it to heart and to know that we are in position to prevent those type of situations from happening where successful, talented, hardworking people simply removing themselves from the marketplace just to sustain their home duties and raising kids.

And I think it’s not necessarily just the loss of those talents, it’s the contribution to the economy and the society in general that we can impact as leaders in organizations. So thank you for that. That’s very deep and heavy. And there was a big room for considerations in the ideation. So thank you for that.

Rich Brooks: Jodi, this has been great. And we always ask one question of all of our guests who come on the show for the Fast Forward Maine Podcast. And it’s this, what one thing would you change if you could to improve the business ecosystem here in Maine?

Jodi Flynn: Well, taking on a feminine level of leadership – which is all about collaboration – I tapped into some of my friends who are women business owners and asked them this question. And one thing that trended out more than anything else was the mentality that you can’t do business in Maine, or you can’t have a highly successful business in Maine.

There’s this concept that Maine’s too small or there’s not enough money here. I have to fight that mindset as well that businesses in Maine will not pay me the same price as a business in Boston. And it’s just not true. It doesn’t play out. And sometimes our mindsets can create these self-fulfilling prophecies. We don’t think we can earn what we can earn in a different market in Maine, so we lower our prices or we compromise. And more and more when talking to these friends they’re like, “I’m competing with the Boston and the Chicago markets, and I’m doing just as well, if not better than most of those people there.” So there’s this myth that Maine is too small and the money’s not here. But I think what we’re seeing, especially with some of the money that’s being poured into Maine right now, is the money is here. We just have to get over that mentality.

Yury Nabakov: That is great. Jodi, for the listeners who want to learn more about you, your business and the services that you provide, and potentially how you may help them, where should they go to find you, or where do you interact and spend most of your time?

Jodi Flynn: Well my hub is my website, which is womentakingthelead.com. And I’m also pretty active on LinkedIn and it’s becoming one of my new favorite platforms to be on. And you can find me there as Jodi Flynn or linkedin.com/in/jodimflynn.

Yury Nabakov: Perfect testing. Thank you,

Rich Brooks: Jodi, this has been great. Thank you so much for coming by and sharing your expertise with us.

Jodi Flynn: Thank you, Rich and Yury. I’m excited to be here. Go Maine.

Rich: Great interview with Jodi. An absolute pleasure to have her on the show. I’ve known her for years, just very smart and very emotionally intelligent person. I always love our conversations. In fact, in the pre-interview chat it was just so great to see her because we hadn’t seen each other for so long because of COVID. So it was just fantastic to catch up with her. For a full transcript of everything that Jodi shared with us, along with the links to her website, you can head on over to fastforwardmaine.com/66. Yeah, that’s right, this is our 66th episode. We were just talking about that right before I hit the record button.

Yury is ecstatic about the number 66. Apparently he thinks we’re doing a great job. Hopefully you do, too. This is the part of the show where we do our “fast takes”. So Yury, what was your “fast take” today?

Yury: So my “fast take” is, if you are expecting to see certain changes in behaviors or you want to elevate a specific aspect of your high-performing employees, you shouldn’t be focused on the task. You should be focusing on enhancing or changing the identity in the sense that will help your employees to be that kind of person that you wish them to be. But ultimately it starts with you. So if you want to see your employees asking for help or offering help or taking on novelty initiatives, you need to be modeling that behavior yourself. So before going in expecting a mile long list of things that your people should be doing, you should be displaying it yourself and be willing to not be afraid to fail. And nurture the relationship with your high-performing employees. So that is the “fast take” for me. Rich, what is your “fast take”?

Rich: Well, I think we’re in alignment here because I agree. My “fast take” was high-performing women, really have high-performing employees, but especially women, they’re not going to necessarily come to you with their problems because they don’t want to fail and they don’t want to be seen as failures. So it’s important as leaders to create an environment where employees feel safe. And that may mean sharing your own failures with them and being vulnerable in front of your team, which is a really difficult thing for a lot of leaders to do. But if we want to get the best out of our people and if we want to raise them up, that’s the kind of behavior that we have to be partaking in.

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