Six Paths to Leadership with Meredith Persily, CEO of Aspire at Work

Six Paths to Leadership with Meredith Persily, CEO of Aspire@Work

On this week’s episode of The Leadership Habit podcast, Jenn sat down with Meredith Persily to talk about her newest book that she co-authored, Six Paths to Leadership. Let me tell you a little more about Meredith.

Meredith is the CEO of Aspire at Work, leadership development and executive coaching firm based in Washington, DC. She is the co-author, as I said, of Six Paths to Leadership: Lessons from Successful Executives, Politicians, Entrepreneurs, and More. Meredith specializes in the leadership challenges of complex global organizations, including technology, healthcare, financial services, and government contractors. She has delivered leadership programs in 17 countries across five continents and 38 states, and the District of Columbia.

Meredith serves on the faculty of American University’s School of Public Administration’s Key Leadership Programs. She graduated with an MBA from the University of Chicago booth school of business and a B.A. with honors from Brown University. She earned a certificate in leadership coaching from Georgetown University and is credentialed as a Professional Certified Coach (P.C.C.) by the International Coach Federation. I hope you enjoy the conversation as Meredith and I talk about the book that she recently co-authored– Six Paths to Leadership. I promise you it will at least give some answers as to why you might have had some obstacles initially on the job or why you might be encountering obstacles with influence in your current role. Here she is.

Meet Meredith Persily, CEO of Aspire@Work

Jenn DeWall:  Oh my gosh. Hello. Hello, Leadership Habit audience! I am so excited to bring to you today, Meredith Persily, thank you so much for coming on the show. I got to read your book, Six Paths to Leadership. You already know what you’re talking about this on the pre-call. I loved your book because it’s just a unique perspective that I feel isn’t talked about at all, really at all. I actually have not seen this perspective before, and I read a lot on leadership. And so I was so jazzed to read it, get your findings, hear your perspective, cuz at the end of the day, this book, I feel like, and I know this feels like a big plug, but I just do think people need to hear it. It’s a way to help leaders feel seen of understanding why we may be successful or not might actually come down to our path to leadership. So Meredith, if you could just go ahead, tell our audience a little bit more about yourself, how you came to be or how you actually came to write this book, the six paths to leadership because you’re writing a book that I feel like is not talked about. Like the topic in here is just no one ever talks about how you got to leadership. They talk about the skills and you address that. But before I keep going, go ahead. Tell us about yourself and what inspired you to write this book.

Meredith Persily:  Great. Thanks, Jenn. It’s great to be here with you, and thanks for reading the book. Really appreciate it. So I work in Washington, DC as an executive coach, a leadership professor facilitator, and a consultant, and I work across sectors. So I work with government leaders both in the executive branch as well as in the legislative branch. So elected members, Congress, House and Senate. I also teach in an executive program for senior people the in the executive branch. So those are our federal agencies. And then, I work with nonprofits that intersect with kind of the D.C. world. And then, I work with corporations across the world, again as an executive coach and leadership professor. My personal mission is to, you know, help people to reach their potential. And I like to work at the leadership level because there’s a wonderful cascading effect, right?

Meredith Persily:  When we have effective leaders, they then influence their teams and organizations. And I believe really strongly that if people are fulfilled and happy at work, they bring that home to families, communities, and our society and, ultimately, our world. I love my work every single day and really want to make a contribution to the leadership field. And that brings us to book. I, one of the areas and I think many executive coaches work with is around onboarding executives into new positions. I often will help design these onboarding programs. You know, certainly doing the one-on-one coaching, but also designing leadership, designing programs to help onboard leaders effectively. So again, corporations, nonprofits, and then would support the orientation of new members of Congress and their senior staff. And as I looked across these sectors, it was very clear to me that what they needed to do in their first 90 days was very, very different.

Each Path to Leadership is Different

Meredith Persily:  And it’s not about writing about, you know, public sector leadership versus private sector leadership, but really what the distinction was, was how they came into their leadership position. And again, working with leaders more on an individual basis, what became clear to me is that there are both opportunities and challenges, and these opportunities weren’t being fully leveraged, and the challenges were not being proactively managed enough. And as we talk about some of the individual paths, then I can get into a little bit more detail and perhaps give you some stories, you know, from my experience.

You know, one thing I would just say just as an example is we have an entire chapter on family legacy leadership, and there’s a tremendous amount of advantage or opportunity that comes from being a family legacy leader. And are you stepping in fully to those advantages by leveraging the family story, leveraging the family values and identity, and are you managing that challenge of potential perception of entitlement directly, and how can leaders more effectively manage that perception? And so that was one I was, I was working with two family leaders and one was really leveraging those opportunities, and one was fighting against that opportunity. And so that was where, you know, I, I really started thinking through, we need to be doing this for all of the different leadership paths.

Jenn DeWall:  Yes. Well, and I, I do, because I think that often, you know, and obviously your book talks about this, you, you know, you, you come to leadership, but you don’t actually reflect on how did I get here. Unless maybe we’re talking about an elected official because then it makes sense or the appointed if you’re invited. But I think sometimes you just don’t reflect on, oh my gosh, how did I get here? And what do I want to do in the next 90 days? Or what does you know, why is that first 90 days even important?

Because I think a lot of people neglect to even consider the timeliness or the urgency that they have of what they need to do within the first 90 days to set themselves up for success. Too often. What I hear my work is more of that, oh, there’s that overwhelm that comes. There’s that I don’t know what to do. And you talk about some of the challenges too in the book, but it’s not necessarily looking at it from the outside of, okay, what’s gonna be working for or against me that will ultimately determine my success? And I know that you even quoted something from Harvard business review in this book that, and I was blown away by even that quote of what was it like 60% of executives fail within their first, you know, I forget the time period.

Meredith Persily:  It’s about six months. Yeah, yeah. I think it’s at least 50%. Yeah. Mm-hmm

Jenn DeWall:  <Affirmative> and that’s, you know, and I think again, if you understood how to look at it and do that analysis of what we were talking about in the pre-call the context, and maybe I’ll jump into that, then I think people would be a little bit kinder to themselves and a little bit more strategic in their approach instead of just feeling like, all right, I got the job perfect. And you know, your book talks about where, so where people get it wrong. So let’s maybe go into what’s wrong today. And what you’re seeing, or what, when we were talking about in the pre-call of the needs that organizations have of leaders today, where do you think this book kind of fits in and helping people navigate change or lead change as you were talking about?

What are the Six Paths to Leadership?

Meredith Persily:  Yeah. Well, let me let me step back just for one second, to orient the callers to what the six paths even are. And then, yeah, I’ll, I’ll jump into that. Because I, you and I could just jump right into each path. <Laugh> So the six paths real quickly are elected into the position appointed, which is both political appointees, which are really, really big positions, as well as board appointees. The next one is promoted from within then there’s the hired from the outside hired from the outside. We call that the outsider path. Then we have family legacy, which I talked about before. And then finally, the sixth path is the creator path or the founder path, right? So those are for the entrepreneurs who, you know, found a company and then grow that company to the point where they are in a leadership position.

Okay. So those are the six paths. You know, in the context of the past few years, all of the challenges that organizations have been facing, particularly with the fast changes around COVID but also the racial reckoning that is, that has happened particularly in the U.S. and organizations are, are pivoting very quickly and really counting on their leaders to be able to do that. And if you think about it, a very important, if not the most important part of leading change is about understanding your context and being able to move quickly, right. As a result. And if we go through each one of these paths, the issues that you need to think about are the same, but then there’s there’s a distinction, right?

So for example, if we think about our stakeholders, right your stakeholders as an elected leader are gonna be your constituents, the press leadership of your party as well as your staff. And then we have a whole bunch of other types of interest groups that would be your stakeholders, right. And so how are you thinking about understanding and leading those stakeholders right from the get go. Now, when you are internally promoted most of your stakeholders, if not, all of them are people that you’ve known for some time, you’ve already built those relationships, but those relationships have a lot of assumptions about who you are, what you’re capable of, that reputation is your greatest advantage and your greatest challenge, because it’s a lot harder to shift people’s perception when they’ve known it over time. But then when we have the outsider, right, the person coming in from the outside you know, they are hired more based on their credibility from their previous position.

Each Path to Leadership has Specific Challenges

Meredith Persily:  And they have to make first impressions on all of these new stakeholders and they have to understand you know, what are the wants and needs? How do they lead this new team effectively coming in from the outside and keep, and, you know, retain those individuals that they most want to retain. But then also make sure that they proactively own that building of relationships across this whole new stakeholder base. Again, those are just a few examples. I could go one by one. Yeah. And they’re really, really specific challenges.

One more that I, on the stakeholder front on the appointed. So in political appointee positions, there’s actually a term for the people that sit just under those political appointees, which are extremely senior positions in our government. And they call themselves the “We Bees”. And you might remember that from the book. So “we be here before you and we be here after you”, right. And so, you know, you’re, you have short timers. People who have to have an impact in a very short period of time, trying to lead people who are much longer term employees. It creates a very different dynamic than we might see in the promoted from within where you’re getting promoted. You know, your boss gets promoted, you get promoted into that position than other people are getting, you know, promoted behind you potentially. Right. So you know, very, very different dynamic.

How Different Leadership Paths Approach Change Management

Jenn DeWall:  So let’s get into talking about change, the ability to make change work fast, quick, efficient will depend on your path to leadership. And the book talks about multiple, and you did a ton of research on this too. So I just wanted to emphasize that, that this was a research-backed book in terms of how you even drew these conclusions. What were some of the key differences that you had talked about as it relates to, you know, the six paths? And I know you touched on a few in terms of reputation but maybe let’s, let’s dive into that to help our audience understand a little bit of the places that you need to consider. One, I think is also important to talk about is culture that your book talks about is yeah. You know, understanding what your role is in shaping the culture, what your attitude needs to be, but what are some of the key differences? I guess there are differences in terms of how you would approach it based on your path to leadership.

Meredith Persily:  Yeah. So, I mean, you know, we could go on and on down almost every single attribute in this area, but let me focus on a few. So what might be perspective, right? So what is kind of the lens through which you look at your leadership position and how that’s gonna be different depending on which path you’re on? So for example, the insider path has that real insider view, right? Again, that perspective comes from, you know, already knowing the organization, knowing, knowing what has succeeded and what has failed and, therefore, you know, again, great perspective, huge strength for that path. But on the opportunity or on the challenging side of that they might be less able or less willing to initiate change, right? Because they have that history of who’s tried what, what resistance they’re going to get you know, and they can be perceived as, and also have a much harder time being a change agent.

Meredith Persily:  You know, this, this layers onto perspective, as well as you know, the relationship piece. But imagine if you get promoted into your boss’s position, your boss gets promoted into that next position. And then now you wanna do things very differently from the way that your boss did them, right? Yeah. Much, much harder than if you were an outside hire, because, so you’re basically telling the person who promoted you and has probably been key to your success, that you have a better way of doing things, right. So really really challenging to be a change agent, really, really great in terms of quick assimilation, cultural fit and credibility because presumably there’s a reputation that you, that was positive that you can build on. And that’s why you got promoted.

Establishing Yourself as a Leader

Jenn DeWall:  To ask a clarifying question, you know, and most of my experience has been, you know, within the path that promoted from within. And so when I think about that, I think about the challenge of going against the green, which is what it can feel like if I had already established success within this organization, I was doing it. And heck, I mean, I’ve seen this in organizations where you might get promoted because you seem like that person that’s exactly like me. And so then I want you, which makes it hard to think about going against the grain, because then you might alienate yourself. So what advice or recommendation would you give to someone to maybe take that leap in navigating change and blazing their own trail?

Meredith Persily:  Yeah, I mean, I think I think for the promoted path, there are a couple things, right? So there’s, there is that resistance externally, but there’s also the resistance internally. And one of the things that when we were, you know, bouncing these ideas onto coaches that, that we talked about is this idea of trying on another path’s lens or hat. Right. So, you know, maybe because being a change agent is a lot harder in that promoted path to ask your client, how would you do this differently if you had been the founder of this company, or how would you do this differently if you in fact, were an outsider or what if you had the job security of the family legacy leader, how would you approach that differently? So I think, you know, that alone can kind of challenge one’s thoughts.

But then the other piece is that, you know, presumably, you have a lot of credibility. They know you’re on their team having been promoted from within, and so that’s currency to spend. Right. And so, you know, how can you both, I mean, it’s a great polarity. Hopefully you’ve walk, you’ve talked about polarities on this show, right? It’s that both and thinking and it’s a really great polarity. How can I be for both continuity and change, right? And as an internal, you know, promoted leader, you have a wonderful opportunity to talk about everything that’s working and how you might be able to make things better. Right. and so spend some of that currency and then try on that new hat to make yourself bold and courageous around, around change.

Jenn DeWall:  So then let’s look at the difference if you were appointed, because if you’re appointed, and I feel like maybe, you know, just the, the similarities between appointed and elected, I feel like people are used to, like, this is what we want, or I guess, appointed, they want the results in a different way in terms of their own profitability, but how should they, how should they approach that? Like how should they approach change or how should they leverage that?

Meredith Persily:  Yeah. So gosh, those are two actually quite different paths, even though they’re both found in, or among our public service leaders there’s, there’s a number of challenges for the appointed leader. One of them is that their, one of them that’s both strength and a challenge is that their power really comes from the principal who appointed them. Right. So there’s a lot of positional power that’s based on both authority. And again, you know, were they appointed by the governor or by the president? And at the end of the day, the agenda is really being set for them by the principal, you know, and obviously the principal senior staff. And so, you know, how are you leveraging that positional power is a really important thing to think about. But one of the biggest challenges for that appointed leader is I mean, there’s certainly a lot of the cultural, you know, cultural changes that we talked about before coming in.

Meredith Persily:  But in general, those positions are extremely demanding. And most the average time that people are in those positions is actually only 18 months. There’s a lot of turnover at the two-year point an incredible amount of turnover at the four-year point. But it’s very hard for these are kind of 24-7 positions, many of them. And so, you know, we see a lot of turnover among those positions for a variety of reasons. And certainly with new administrations, those jobs turn as well. And so in the context of change, right, you have to, you know, when we think about change so much about change is about positioning organizations for the future, right? But when you’re only in position for 18 months, you’re trying to have an impact for your principal in a very short period of time. And so the strategies and stories that we outlined the most from people who’ve held those positions were really about figuring out what are the most important priorities, where can you have an impact and getting, working on those focus areas as soon as possible.

Power Dynamics and the Paths to Leadership

Jenn DeWall: I love how the book talks about power, because again, a lot of people, I wanna, you, you brought that in like where your power comes from, whether you’re appointed, you get the power, what, and if you’re obviously promoted from within you have that because of your established reputation and success, but then we have, and I’m sure a lot of leaders who are listening to this right now, the people that are coming from the outside, I mean, we’re seeing what call it the big quit, the great resignation, whatever you want to call it. So a lot of people are likely, you know, they’re at this point of a fresh start, a new lens, how, or what advice would you give for them to make change or even understand their power? Because it’s easy to say, like you actually have either limited power because people don’t know you. I mean, your book, it’s important to say that we’re talking about a few of these differences, but there’s key themes that everyone reputation trust your first impression where your power comes from culture. There’s so many different lenses, but if you were pointed from, or excuse me, you’ve taken from the outside. So if you were brought in from the outside, how do you need to approach and understand power as it relates to your ability influence?

Meredith Persily:  Yeah. And I think, you know, you’re absolutely right. The great resignation, is it really important trend happening right now at the leadership level? Right. We do see, you know, we do see movement but, but you know, high-level leadership positions are still gonna be quite competitive. And that’s important because so much of your power does come from that credibility of a competitive recruitment process. Right. So, you know, let me I’ll, I’ll kind of go through on power. I’m looking at table 1.1 for those who who buy the book and they can see, you know, right across the board. So you already mentioned the when it comes to power and authority, the insider you know, it’s their powers through connections. All right. But they might struggle with power over former peers. Right. How do you create a– or, how do you have, and build additional power against former peers that used to hang out with and complain about the boss with right.

Then you have the external hire credibility from a competitive process, but also, you know, companies tend to go to the outside because they don’t have that skill, knowledge, experience from within. So that’s also, it comes with additional power from, you know, it’s like a scarce asset, right. That you’re bringing in. Then if we looked at electeds, that power is very clearly delineated through the leadership positions, you have the caucuses that you’re, you’re a member of and then relationship power through you know, if you are not, not in a leadership position yourself, how strong is your relationship with those who do have more have more power in our elected system? And, you know, I can’t emphasize enough the importance of, you know, how much more power people in leadership, at least in the legislative branch have over people who are outside of leadership, where really your power is more about your vote.

Then when we have the appointed again, your power comes from the principal who appointed you as well as specific legal authorities that are granted to those positions. And you cannot go, you know, above or below. Those things are very clearly delineated, especially around budgets and legal authority. And then we have the founder path, where does their power come from? Well, theirs is, you know, usually there’re also the, a majority shareholder or the owner, right. Usually not necessarily, it really depends on where over the course of their growth, that you’re, that you’re looking at it, but again, their power comes from that origination story. That brings so much credibility. But then also that for many of them they’ve been unilaterally making, you know, many of the decisions up until a period of time.

Meredith Persily:  And then finally we have the family, right. And so again, similar to the creator there’s ownership, the ownership structure gives them additional power, and then they have that positional power as well. On the, you know, the downside, it can be a very subjective use of power and our best practices in order to temper that are to have some more objective governance structures to help people through those challenging positions.

Jenn DeWall:  So I appreciate you going through, so there’s a table in the book that details, you know, the different themes and variations across the six paths. And just talking about how or what that actually looks like.

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What Mistakes to People Make on their Paths to Leadership?

Jenn DeWall:  Where do you think maybe we could go through and talk about a few of the missteps that people make at each of the levels because they have to be mindful and, and they’ll maybe then hear those themes coming out through that. But let’s talk about some of the mistakes that maybe if we can go through the table too, let’s talk about some of the mistakes that an insider might make. I know that this is a different piece of the book.

Meredith Persily:  Yeah, no, no, no. That’s great. one of the things that I would just say applies across all paths first, and then when we get into the specifics, you’re gonna see this even more is that when you’re new in a leadership position, you are in the fishbowl, right. People are watching you and you’re gonna have some level of insecurity about, you know, you know, are people gonna like me? Are they gonna follow me? What should I even be doing? Because this is a new job. Yeah. And yet when we think about what in fact is the definition of leadership, it’s about, you know, inspiring and engaging your followers. And so at this time, when you’re very kind of self, you know, self-involved concerned about self the most important thing you need to be doing is thinking about everybody else that you’re trying to lead, right.

And how do I win over the hearts and minds? And so the missteps, I wanted to start with that because the missteps really have to do with that. It’s about thinking too much about yourself and not thinking enough about others. So what is the misstep in the insider path? It’s that, it’s that it’s that former peers and not renegotiating that relationship enough. Right. Still trying to be their friend, which is okay. And you have to, you know, lift it up in terms of providing that guidance, you know, setting direction and sometimes even creating some separation.

We had some stories about you know, effective leaders, really having to renegotiate those relationships in an effective way. The most important one being how much time are they gonna be able to, you know, give these individuals, especially when their stakeholders move more externally, like in a CEO position. And so that would be the first one. And so, you know, when, when, when someone gets promoted and is leading former peers, they need to be really thinking about, you know, which team members do I wanna keep, and what’s my plan for keeping them. And then also, who might I not wanna keep? And what’s my plan for moving those individuals out, because maybe, you know, they are never going to buy into that promotion.

Jenn DeWall:  Right. They’ll always undermine your efforts or continue that chatter and be your potential enemy. And, and, and you’re in the book, talks photo that for a variety of reasons, you could have been their competition. They wanted that role and they didn’t get it. And so they’re just not going to buy in because that of their own, you know, kind of challenges or disappointment.

Renegotiating Leadership Relationships After a Promotion

Meredith Persily:  Yeah. Now on the outsider path, there are number of missteps that they make. The one that I’m going to highlight is the outsider who comes from the competition. And so, you know, from the outsider’s perspective, the reason you hired me was to bring in this new perspective, the, and the experience of being better than you, right? Yeah. But are you coming in with arrogance? Are you coming in with humility? And you know, especially in cutthroat industries, you know, you were the enemy <laugh> right.

And so you come in, and they’re supposed to trust you when they’ve been fighting against you all of this time. And you know, some of the stories that were you know, most rejected were individuals who, you know, were in fact brought in because they came from the number one, maybe now they’re going to the number three or number four, but then they overuse that. And they say, well at, you know, X company, we did this. And at X company, we did that and people get pretty tired of it. And so, you know, our recommendation on that one is to figure out what you like about the new company and give that a lot of, you know honor that as well. Right. You know, why you came, and really show that you are one of them now. And why you’re so excited about being part of their team. But you gotta proactively manage that transition. Right.

Jenn DeWall:  I think that’s an important piece of how are you showing up when you come in there? Are you like, well, they brought me in because I worked for the competition. So I have all the smarts and solutions that this organization doesn’t have. Right. I mean, we’ve seen that, that ego-centric like, look at me, look at me instead of understanding that people are naturally then going to resist you because they don’t have that trust because they have been working against you. So if you do that, then you lose your influence ability.

Meredith Persily:  Absolutely. On the elected side I’d say the big, there’s so many missteps as well that we can get into the details of like hiring the wrong people, hiring people, you can’t fire things like that. But I would say from a leadership perspective focusing on too much on what you’re not able to do, as opposed to what you are able to do elected positions, obviously with the exception of the presidency, which, you know, has a tremendous amount of power, but when you start going into the legislative branch, so executive branch positions, governors, mayors president, they, they do oversee an awful lot, but again on the legislative side you know, they’re not they’re not able to do a lot of the things that they want to be able to influence. And so there are those leaders who get frustrated with that, but then there are others who really look at the power that they do have, and focus on that.

And one of the things we talk about with some great stories from former elected leaders is the power to convene, right. Just having that power to call the meeting, to get different stakeholders together, to help move things can be really, really powerful. So how do you, how do you leverage the opportunities that might not be as obvious to you where you can also have an impact just maybe not in the way you would most like to have that impact?

On the appointed front, the missteps are definitely about disrespecting that group right underneath them. They are the key to your success. They’re the ones that make things happen that implement your ideas and policies. And so not treating them with respect will really set you up for failure. So, you know, we had really great stories of effective leaders who you know, interviewed them right away asked them how they could be helpful you know, would go visit them instead of just calling them into their office. And so honoring their public service history and the expertise that they bring

Meredith Persily:  On the creator side, you know, it’s interesting the family business and the creators make some of the same mistakes. And a lot of it is about that personal and professional overlap. Right? If you found your company with a bunch of buddies, harder decisions down the road. Same thing with family, how do you make some of those hard decisions? And so in both cases, you know, we want to encourage through the stories of successful leaders. You know, more objectivity, more self-awareness thinking about how do you compliment your skill and make sure that, you know, there are people there to cover your blind spots. So I think those, I think that covers all of them. Right. Yeah.

Establishing Credibility as a Legacy Leader

Jenn DeWall:  I wanna ask one more question about the legacy, because I think that I naturally might, you know, as an individual might be like, yeah, like, did you get it because you actually deserved it or did you get it because your name? So how do you actually, you know, build trust from the legacy perspective? Because I think that, that I naturally, as an outsider and looking at it as like, well, of course, like, they’re just gonna keep promoting whether or not we’re bringing you in whether or not you’re capable or competent, whatever that might be. And I know that’s unfair, that’s a bias on my part, but how do you build that trust?

Meredith Persily:  Yeah. Yeah. Great question. You know I really I learned so much in this chapter and my empathy for people running successful family businesses really just went up tremendously. Appreciating, you know, how complex it is to have so much personal investment in these companies, both in terms of the success, as well as the relationships that are behind them. And it’s so hard in this, you know, in these times where we wanna separate work in life. You know, it’s very difficult, you know, at, at the holiday table when extended family are all, you know shareholders of the business, many of them working in the business. And how do you, you know, create some of those separations

Jenn DeWall:  I’m picturing the show Succession right now. <Laugh> like, as you’re talking about them, then just sitting around and undermining, like, that’s what goes through my head. Yeah.

Meredith Persily:  It’s very, very complicated. And so, you know, what we found in terms of best practice here is really making sure that you’re bringing in some non-family members at the senior level for one, right. Some real industry experts and people who have a different approach to the business than you. A different perspective, because we always want diversity of perspective. But then the other piece is, you know, you talk about how others might be judging them. They’re also judging themselves, you know, am I here because of my family or am I here because I really deserve these positions. And so the family businesses that seem to get this right, they set up objective criteria for their family members to hold those positions. And you know, some standard criteria, you know, might be certain level of education, you know, oftentimes graduate school, you know, MBA and such.

The other is that they have to have a certain number of years of experience outside of the family business. And they have to have been successful. So they have to have been promoted and shown a success track record in another business before they’re able to hold a senior position in their business. And then just in general, you know, having very, very clear governance documents that are not about specific individuals, but are equally applied to all members of the family. All of those things seem to be really, really helpful. Both in terms of that internal story around entitlement and managing it, but then certainly around that external story as well.

Jenn DeWall:  The complexity of a legacy is just, I mean, thank goodness. I never had that opportunity because I don’t know what I would do because at the end of the day, even from my perspective or the chair that I sit in, when I read this book is like, how do you even get people to leverage their confidence? Because all of these, I feel like are vulnerable to imposter syndrome. They are vulnerable to, will I actually be effective? How will I even know? And so how do you like going back to that 90 days and maybe this is a great closing consideration, but what are some of, how would you even start a 90 day expectation or plan for yourself and then how do you measure that success? I don’t, that’s too high-level, but like,

Knowing Your Path to Leadership in Order to Lead Your Stakeholders

Meredith Persily:  Yeah, that’s, that’s a lot, but I’ll give you a couple things right there. Yeah. you know, the first is, is about your learning plan which both includes, you know, the people that you’re gonna interview and the questions that you’re going to ask them, depending on your path. Okay. So again, this goes back to knowing who your stakeholders are and asking those questions. There’s, there’s a lot of great work, Michael Watkins, who actually wrote a book called The First 90 days talks about the the listening tour that you’re supposed to go on. We, we do a variation of that in our book that’s by path. Who should be part of that listening tour and what are the different types of questions you should be asking depending on the path.

Meredith Persily:  And so just as one example if you’re promoted from within versus an external hire if you’re coming in from the outside, you’re really just trying to understand like the networks, how things work, you know, norms and practices, the culture. But if you’re internally promoted you know, what are you, what assumptions are you making based on the way things were done at that level. And then how do you integrate into that new level in terms of norms and practices across the organization with new peers, etc. And so, you know, that’s gonna be absolutely key. Again, the, that issue around your team, right? Winning over the hearts and minds of the team or your other stakeholders. Again, depending on what that path is, you need to think about that team really differently.

Meredith Persily:  Creators, they’ve been there since the beginning. So they’re gonna have you know, they’re not gonna have that same concept of kind of 90 days. But then what we wanna think about with them is like, what is the point that you need to mix things up, bring in bring in new decision makers. What we see as you know, one of the biggest challenges with founders is distributing their decision-making authority. They tend to have the worst reputation for being kind of micromanagers and overly involved, because at some point they did in fact do every job. And so how do they lift up? And so, you know, how do they make for themselves these kind of artificial transitions that enable them to scale the business, to move to that new level of leadership? Because if they keep on doing things the way they’ve always done another great book out there is Marshall, Goldsmith’s, What Got You Here, Won’t Get You There.

Right. Really applies to creators. Who’ve, you know, something has made them successful, but now they need to operate at a new level right. And distribute, especially their power because they don’t distribute, they power. They’re gonna be a bottleneck. And people aren’t gonna be inspired to stay and, and work there. Right. so you know, those, again are some of those different ideas. I think on the family legacy side, you know, some of the great stories that we heard about is, again, how that family DNA story gets told over time. And so we wanna make sure that that’s a huge strength and that as new family legacy leaders come in, that they’re really well versed in what that family story is, and that you build that connection. Because the further they get away from that first generation, they might not have all of that history. And it’s a huge advantage for the family legacy leader.

Who Should Read Six Paths to Leadership?

Jenn DeWall:  I’m going back to like some of my post-it notes in here, but, you know, in, in closing, because there’s no way we can encapsulate everything that the book had talked about. And there’s so much research here, but this book can serve a lot of people, whether it’s the individual that is the leader, whether it’s someone that’s supporting the leader. So as we close, who do you think could benefit from reading this book?

Meredith Persily: Yeah, well, I think you know, any, any person who’s new into a leadership position should certainly, you know, read the book, focus on the chapter of whatever their path is and also to read the chapter, whatever their path was and so that they can understand that new lens and what some of those biases might be from their previous path. So definitely, you know, people new into leadership positions. It’s a great gift for someone when they get that promotion. Yeah. And then,

Jenn DeWall:  Well, again, they get to feel heard, like, I feel like this eliminates some of that extra noise or head trash that comes into play when we’re not paying attention to the context of what got us there. So yes, give this to them. Like I swear as a coach, I feel like people would just, the confidence that would flourish in that, you know, they would give a little bit more grace to themselves if they understood that perspective.

Meredith Persily:  Yeah. And then, you know, there are a few other groups, you know, we think and benefit, certainly everyone who supports leaders. So coaches, consultants, head hunters, you know, recruiters. All of them. It’s really helpful to understand those advantages and disadvantages. The hiring committees who are responsible for onboarding new leaders. They need to be thinking about, you know if they’re debating between a promotion or an outside hire, how do they, how do they set either one of them up for success? So those are critical for young leaders or people earlier in their career. You know, we do, we have a whole chapter kind of around, you know, one of the closing, I would say in one of the closing chapters, we, we talk a lot about, you know, how do you think about path relative to your own career path?

There’s No Such Thing as One-Size-Fits-All Leadership

Meredith Persily: If you’re someone who’s great at first impression, that outsider path might be good. If you’re someone who really likes to build up reputation relationships over time, you might wanna think about, you know, joining organizations where there’s gonna be lots of opportunity on that promoted path, right. So, you know, match up your own strengths. And we have a, we have a little tool just for that, like match up your own strengths and, and development areas against the different paths. And then finally we want our book. And again, I wanna mention my co-author Mark Clark. I could not have done this work without him. He’s a professor in the Cogo school of business at an American university. And you know, for the two of us and again, this lens, which is, you know, even more academic we want leadership writers and theorists and professors to think about these paths and make sure that we get away from this kind of one-size-fits-all approach to leadership.

And that we bring this framework into, you know, all other attributes that we see as key to leadership. So, you know, of course emotional intelligence, which is written out written about an awful lot is being key to leadership. Effectiveness is important, but if we, if we take the E.Q. skills, right, and we layer that against path you’re gonna have different opportunities and challenges, right? So, you know, one of the things is just, is, you know is kind of conflict management and as well as, you know, networks and the politics of an organization. Layer that against path, and you’re gonna have different approaches to building that competency.

Jenn DeWall:  It’s relevant for so many people. I know that I will be using this book for, I absolutely will be because it, it just provides a better lens to understand what strategy is going to be effective. And if you’re looking for strategies, if you’re looking for approaches, this book details, you know, the opportunities that you have, the challenges that you’re gonna run into, as well as the strategies that you can leverage. And I just appreciate, again, this unique perspective that I have not seen out there. I’ve done a ton of podcast interviews. So I’m not just saying this, I just appreciate this different voice, because I think it’s much more helpful for your long term success to understand this context, especially as it relates to going back to the first topic- change – or whatever you’re trying to accomplish Meredith, how can people get in touch with you?

Where to Find More From Meredith Persily

Meredith Persily:  Well, certainly they can you know, find me on LinkedIn again. That’s Meredith Persily. And then my website is That’s the name of my business dot com.

Jenn DeWall: Fair to thank you so much for being on the show. Thank you so much for writing this book, because again, it’s a void within the leadership space and it was great to have this conversation. We could not even cover everything that you know, this book talks about. So I would highly recommend to get it. It’s going to give you a unique point of view and how you can look at yourself or even look at how you support others. And I swear, I’m not saying this just to get in Meredith’s good graces. I just legitimately think it’s a very, very foundational, helpful tool to understand what you’re up against when you actually come into leadership. So thank you so much for writing this book, Six Paths to Leadership: Lessons From Successful Executives, Politicians, Entrepreneurs, and More. So go and get a copy of your book. Meredith, thank you so much for joining us on the show.

Meredith Persily:  Thank you, Jenn. Really appreciate the time with you.

Jenn DeWall:  Thank you so much for listening to this episode of The Leadership Habit podcast. I hope you enjoyed today’s conversation and it had you reflecting and thinking about how you might approach things differently based on your path to leadership. Now, if you want to connect with Meredith, you can head on over to There you can find out more information about her services and also purchase the book SIx Paths to Leadership, I promise you it will not disappoint. And of course, if you know someone that could benefit from hearing this message or conversation, share this podcast episode with them, and please leave us a review on your favorite podcast streaming service. Your reviews are what helps us go to the top and gets our message heard. And finally, if you enjoyed this and you’re looking to further develop your leadership development needs, head out over to We would love to connect with you. And in exchange, we would offer you a complimentary leadership workshop. So please connect with us, reach out to us and help us develop better leaders for your organization.