76 Self-Aware Leadership and the Future of Work with Jonathan Boone

In this episode of the Knowing Self,Knowing Others podcast, host Nia Thomas is joined by Jonathan Boone, a seasoned strategic operations leader with a diverse background spanning technology, finance, and education. Jonathan shares insights from his extensive career, discussing the evolution of self-awareness in leadership, the importance of maintaining organizational and personal purpose, and the role of civility in the workplace.

Jonathan dives into his experiences across different sectors, comparing leadership dynamics in finance and education, and highlighting the challenges of managing high performers who may lack self-awareness. He also explores the shifting landscape of work in the face of AI and digital transformation, emphasizing the need for balancing technological advancements with human-centered leadership.

Jonathan also introduces his podcast, How to Fail, which turns personal failures into learning opportunities for others. He shares how this project began as a legacy for his son and has grown into a platform for helping others navigate their own challenges.

Tune in for a thought-provoking conversation on leadership, self-awareness, and the future of work.

Key Topics:

• Jonathan’s career journey and leadership philosophy
• The concept of civility-minded leadership
• The evolving nature of self-awareness
• Organizational and personal purpose
• The impact of AI and technology on the future of work
• Insights from Jonathan’s podcast, How to Fail

Remember to check out the new feature of the Knowing Self, Knowing Others podcast—now you can send a text message directly to the show! Find the link in the show notes to connect with Nia and her guests.

Listen to Jon's podcast

Transcript

[00:00:00] 

Nia: Hello and welcome to the Knowing Self, Knowing Others podcast, where we discuss self aware leadership with thinkers from around the globe. I'm your host, Nia Thomas. Join me as we talk to today's guest.

A very big welcome to today's show to Jonathan Boone, who is a seasoned strategic operations leader with a diverse background in technology, finance, and education. With degrees in criminal justice and history, an MBA in project management, and a doctorate in juris, Jonathan's extensive education is complemented by his professional Scrum Master II certification.

His career includes impactful roles at Bank of America Merrill Lynch, where he enhanced efficiency as an operations project manager and developed bespoke financial strategies as a wealth manager. At Wageworks Health Equity Bank, [00:01:00] he drove significant operational improvements as director of operations at Brookline College and CEO at Virginia college, he implemented strategies that boosted enrollment and financial health. Jonathan, it's brilliant to have you here today. 

Jonathan: I'm glad to be with you today. 

Nia: It's brilliant to have the conversation. So tell us a little bit about your career so far. 

Jonathan: Yeah, so, so far, , I have worked in a number of different educational entities. I've done everything from recruiting to strategic leadership. I've done financial aid et cetera, et cetera, all the way up to CEO and president of a couple of different schools and colleges. I then pivoted into finance and I've been in finance for about six years working for a couple of different banks leading teams and leading people and basically trying to have a more civil minded leadership style in today's corporate America.

Nia: Interesting. So tell us what civil minded means. [00:02:00] What is it is 

Jonathan: a big initiative that we have been rolling out here in the U. S. for sure, in terms of our corporate landscape. The reality and the thought process of it is essentially having conversations and treating people in respectful manners, and not just as human capital to accomplish strategic initiatives and OKRs.

As unfortunately here in America, we definitely have struggled with, we lost our way some while ago and you know, the human side of human resources and we started just looking at people as resources. So being civility minded and having civility initiatives essentially just says, Hey, we want to make sure that our people feel valued and that we take into account their mental health on a day to day.

basis. 

Nia: Interestingly, I had a, another guest on the show a couple of episodes ago, and it was Radhika Nair who was talking about civility and respect in the national health service in the [00:03:00] UK. And actually it's a very popular podcast. It's one that's had a lot of people listening to it. So I think civility and respect in the workplace is really important.

I think that low level civility and respect has the potential as a As an early intervention before things become bullying and harassment. 

Jonathan: Yeah, totally agree. 

Nia: So tell us about self awareness. Obviously on this podcast, we're interested in self awareness and self aware leadership, particularly, what does self awareness mean to you?

How would you define it? 

Jonathan: I think that self awareness and how I would define it it's something that's going to be consistently and constantly evolving. I think a lot of times we look at things like self awareness or healing as destinations when in fact I believe them to be journeys, right?

The fact that I'm self aware at 20 or 25 or 30 that self awareness that I have at those ages doesn't necessarily translate. To the man I am at 40. And that's something that I definitely have you know, worked through and done work [00:04:00] with as I talk about in my podcast, it's one of those things where Self awareness is taking that that honest inventory of oneself and seeing how we can improve and leaning towards my actions and the things that I'm doing versus immediately Looking to become a victim or pointing to the other person and whatever the interaction is as being the cause of me doing something or feeling something.

Nia: I'm glad you said that because actually the title of my book is the Self Awareness Super Highway. I always talk about self awareness as a journey of self awareness, not a journey to self awareness. So we're definitely aligned on that. So you've already told us a little bit about the organizations that you've worked in, what's been your experience of people who are self aware and people who aren't self aware?

How has that felt in the organizations that you've worked in? 

Jonathan: Definitely. The easiest way to look at it is if we [00:05:00] look, or if we say we had a, let's say we had a matrix and it was a square, Let's say on one side we had a self aware person and on the other side we had someone who's highly un self aware, right?

And then at the two bottom points we had someone who was highly functional, let's say a top performer, and on the other side we had someone who was not a high performer. Oftentimes what I've found is the higher the performer, A lot of times the less self aware they are, right. Because performance in this country dictates behavior.

And that's kind of a, an initiative that my leadership style has tried to tackle, right. A lot of times in most of these companies and large organizations, your best performers are kind of the jerks at work, right? They're the people who seem to transcend the corporate level at the highest level, the fastest, because they have the [00:06:00] performance background.

And unfortunately, that doesn't necessarily always correlate. To having a journey that's self aware on how your performance or how your behavior affects other people's behavior in your organization. So for me, if we're talking about that square in terms of what I'm looking for in terms of leadership and when I'm developing leaders, I would rather have a highly self aware person who's a medium performer than a person who's a high performer and has no self awareness.

The person with no self awareness is going to be less coachable they're going to be a lot more dedicated to their particular leadership style as opposed to the person who's self aware being able to be coachable and more adaptable as the work changes and we need to look at different things.

Nia: I've spoken to a few people about this, this dichotomy of people who are at the very top of organizations who are not people people and we often talk about Elon Musk and then Steve Jobs when we're talking about these people, but it's interesting that you [00:07:00] say that you're seeing that at different levels and different organizations.

Are you noticing that there is a difference within educational organizations than finance organizations? And I asked that on the basis that. finance is more technical and you may have people who are more technical expertise than people expertise. 

Jonathan: You know, what's interesting is education and finance are almost exactly the same these days.

Education is so driven these days by technology that it's a lot of the same sort of people at the top of both types of organizations. What I would say is honest is, I find more self aware people at the top of financial organizations and institutions than I find at the top of educational organizations.

We go through a lot for our education, right? We go through. You know, the ups and downs of studying and writing and getting published and [00:08:00] having our work critiqued and looked at, and you would think that would create a very self aware individual, but it doesn't really, though. What it does is it really creates people who become regimented.

In a system of trying to accomplish your goal. But what you'll find is a lot of professors. This is a, this is a perfect example, I wrote a paper for one of my courses when I was in law school. And my professor that that was in, I was in the class for, she looked at it and she assessed it. And she said that it was average, let's say C quality.

I don't know how you guys grade and scale works over those. C for us is like a 70%. So she looked at it and she assessed it at being about a 70%. I had another professor in a writing course look at it for me and she assessed it at a 90. So what happens is, We are always evaluating things based on our personal perspectives, right?

So if you have an inability to put yourself in the [00:09:00] shoes or the position of the person that you are evaluating, a lot of times you can end up stifling people who are looking for opportunities to get better or to achieve and get to the levels that you are at. And in education, unfortunately, a lot of times we don't.

There's not a lot of checks and balances in terms of those systems versus banking, which is so much more highly regulated that I think sometimes you know, more non self aware people slip through the cracks on the educational side versus the financial side. 

Nia: That's really interesting and something that I certainly talk to colleagues about and my team about is knowing your audience.

And I think that's something about how do you step into those individuals shoes to be able to see things from their perspective and talk to them about what is relevant to them and what is impactful to them. So interesting that you say that. So if we think about. All of those things. How do you describe somebody who is an [00:10:00] effective leader?

Jonathan: I think someone who's an effective leader. For me, I still believe that. And I now know that there are lots of different leadership styles. I know that different types of leadership styles exist and work for different types of people. So I don't think there's one sort of person who's an effective leader, right?

I think that you have to be a different type of leader in different organizations and each organization needs its effective leader, which may be different from the next organization. So for me, I know I'm being the most effective leader that I can be when I'm leading from place of servitude. I am very much a service oriented leader.

I like to lead from the bottom up. So I'm not going to ask my people to do things that I'm not willing to do myself. I wanna make sure that I have a really good understanding of the things that I'm asking them to do on a day to day basis. I wanna make sure I understand the buttons that they push in their day to day roles.

I'm not a A top down leadership [00:11:00] style of individuals. So for me, an effective leader is someone who can relate to and understand the daily plights of their people and work with them to accomplish the organization's goals on a day to day basis. 

Nia: So if we think about, as you said, the, the fact that you need to be a different leader to be able to lead different organisations, what have you noticed about those senior leaders and whether they are self aware?

And again, it's a question that I ask on the basis that in my research, when I looked at the literature, it was saying to me that, yes, there is a definite link between senior leaders And high levels of self awareness. But actually when I did my research, it told me exactly the opposite. And when I used to speak to people and I still speak to people about whether they think senior leaders are self aware, they, they usually give me a right chuckle and then they say, not so much.

What are you finding in the organizations you've worked in? 

Jonathan: I think that is absolutely true. I [00:12:00] know for me I've had both. I've had leaders who were, my last two leaders were really self aware. . They both, you know, understood themselves. And because they understood themselves, they were able to understand me quickly more than likely from the interview.

Those are the types of leaders that I typically respond to best. The leaders who understand what their shortcomings are, who understand their strengths, and they are able to use that to personify what I need. to learn from them in order to be effective in my day to day role. Leaders who are very self aware are able to teach, is what I've found.

Leaders who are not self aware don't understand why you can't do something because they can do it. Right. So I think that's the flip side of it. So for me and leader who understands who they are, they're able to say, okay, I understand Jon and I understand how I can relate this thing to him so that he can understand it and effectively carry it [00:13:00] out.

And then another thing that self aware leaders do is they, they communicate they communicate, they over communicate and they do their best to make sure that you get a really good understanding on what it is they're looking for from an expectation perspective so that you can actually be successful.

Nia: Yes. Again, it comes back to that issue of knowing your audience and also understanding your people to be able to relate to them and to resonate with what they need at the point in time. 

Jonathan: Yes. 

Nia: You recently started a podcast called How to Fail. Tell us about the background of that and what's the purpose of that podcast?

Jonathan: Yeah. So how to fail is a podcast that takes my personal failures and essentially gives them the opportunity to become anecdotal stories that people can learn from so that hopefully.

They don't make the same mistakes, or they can become more self aware. See what I did there? And they can use those lessons to [00:14:00] be more effective in the things that they are trying to do. What I wanted to do was, wanted to leave kind of a manual to my son, Who is three on on different things that I've gone through.

So in the event that something happens to me, I had gone through a cancer scare I wanted to be able to leave him something that he could go and watch and learn from as well as other people And just other people who live life because as we all live life, we all have failures and sometimes it's hard for us to learn from those because we see them as negatives or they can be trauma inducing and sometimes those things don't always give us the opportunity to look at them as learning opportunities.

So how to fail at its very core is hopefully just a self help guide for people. 

Nia: I think that's a really important message that it's about sharing your learning and it's not [00:15:00] only about us. Corporate learning or business learning, but maybe your family and children have the opportunity to learn because one thing that we do know from our podcasts and our videos is what the once they're on the internet, they're going to be out there forevermore.

Whilst we still got electricity, we will still be able to access these things. 

Jonathan: You got it. Yes, ma'am. 

Nia: One of your podcast episodes that I was watching, you talk about purpose. What are your thoughts on organizational purpose and I suppose individual purpose as part of that? 

Jonathan: Yeah, I think organizational purpose is just as important as personal purpose.

I think it's the exact yin to the yang of a personal purpose, right? I once worked for a company that was extremely successful. I'm talking about an industry leader in education. And because they lost their purpose, they ended up losing the company. The company actually ended up going bankrupt.

It wasn't because the professors and the teachers and the way that we delivered the education [00:16:00] became worse, they didn't, they were still at the top of the industry, but we started to acquire other schools. So what we would do is we would schools that were going bankrupt, we would acquire them and bring them into the fold of our company, but we didn't have a real vision other than wanting to grow our overall footprint.

So when we brought in these schools that had these problems, it was hard for us to get them. To the same level of educational standard that we had from the parent organization and what it ultimately did was it ended up diluting the entire organization, and the entire organization ended up becoming non profitable because the schools that started.

We're carrying all the schools that we acquired. That's a 100 percent organizational purpose failure. Not understanding what your purpose is or understanding what you want your purpose to be, right? Grow my footprint, but not doing the right thing. The [00:17:00] necessary work to do it in a way that's healthy and doesn't disturb the ecosystem of the , the organization.

And that happens for us as people as well, right? So say for instance I know you probably can't tell right now, but like, let's say right now I was a a stud. I was a muscle stud. I had muscles popping out everywhere. I decided all of a sudden that I also wanted to you know, become an excellent athlete.

So I wanted to use the muscles that I had to become the fastest person in the world. Well, just because you go to the gym and you're really good at that, that doesn't mean that you're going to be the fastest person when you go out into the track. So by losing my focus on being this really fit Person and using what I have in order to you know, be successful and be healthy because I'm trying to pivot into something that I'm not necessarily capable of doing, or I have the necessary training to do.

I can end up you know, hurting myself. I can end up losing the things that I'm good at et cetera, [00:18:00] et cetera. So having organizational purpose and personal purpose, I think are kind of one in the same one being for. You know, organizations and one being for people. 

Nia: In terms of your team, how do you ensure that your team are clear about your purpose, both, I suppose, as a manager to make sure that you've got your individual's purpose feeding into the team and that team feeding into the wider organizational purpose?

Jonathan: Yes, ma'am. So the way that I do that is first by understanding their purpose. So before I ever talk about goals, before I ever talk about you know, evaluations or these types of things that we look at as an organization, I want to understand what are your goals? Why are you on my team? Why are you in this organization?

What is it that you are looking to do? Now, when I ask that question, I'm not looking for a canned answer, right? We all have those answers that we just, you know, Can, can say, I want to know what the real answer is. You know, if you're here working at the [00:19:00] bank and you want to be a chef, I want to know that because I can set you up to be a chef, I can have you cater all of our team events.

I can have you work with our food services department. Like just because you have goals that don't necessarily fit the goal of the overall team doesn't mean that I can't help you accomplish your goals. And if I help you accomplish your goals, More than likely, you're going to be more open to helping me accomplish my goals.

So the first step is having a real understanding of what their goal is and then using their goal to help push along my goal and the goal of the overall organization. 

Nia: I'm, I'm reminded I had a conversation with another podcast guest Turab and Turab's day job is that he's a dentist. So he's also got an interest in, in leadership.

And he was talking about recruitment and how he brings people into the organization. And he said one of the challenges he has is that. He sees people less [00:20:00] willing to put in the effort to be able to, to develop those goals, to understand where they fit in the organization. And he, he found that a lot of people were saying, well, actually, if you want me to test out my skills as part of this interview process, you, you need to pay me.

What is your experience of recruiting and getting people into the organization and linking them to those values? 

Jonathan: You know, it's interesting for me. , I would agree. I would agree with with your, your guest that was a dentist. However, I think one of the things that you can do is have clear expectations on how you're going to help them develop and if they can see a reason to do it that works for them.

I think they're more enamored to try to give you that effort right up front. I think one of the things that you want to do with people is create psychological safety. Psychological safety being the ability [00:21:00] to be comfortable in feeling safe sharing any ideals or ideas that you have.

In a in a specified setting. So if you're creating spaces that are safe for people, then people tend to be willing to take more of a risk and show you what it is they're truly thinking and who they really are in terms of your organization. So I think that's a key. 

Nia: So you recently took my self awareness compass quiz.

What did you learn? And you don't have to give us all of your answers. But what did you learn about either the process or what did you learn about the feedback that people were giving you? 

Jonathan: I think the, I think the thing that's cool about those types of things is that there's always an opportunity to learn.

So for me, believing that I was one way and then having the opportunity to you know, talk to people and give feedback. It's like, okay, these are some things that I can work on. One of the things that I found was sometimes I can be too [00:22:00] positive was one of the the feedbacks that I get from somebody.

So sometimes they think that, me wanting to look at things from a positive perspective all the time can be sometimes detrimental. So they want me to also make sure that I'm also keeping things level. So, you know, if situations are bad or tough being able to communicate that in a more effective way as opposed to taking a sunny side up look at every single thing.

I definitely agreed with a lot of the things that's said. You know, my leadership style was tending to be more self aware, which is positive. But in that self awareness, you also want to make sure that you are you know adaptable and always, like what we talked about earlier, it's a journey.

It's not a, it's not just a, just because I got good on this report card doesn't mean that the, the next one will be just as good if I close myself off. 

Nia: Amazing. Well, I'm glad you, had a discovery and it was something useful and positive. Yes, 

Jonathan: ma'am. 

Nia: Where do you think [00:23:00] that the world of work is going in the future?

So we've got AI, we've got flexible working, we've got hybrid working. What are you seeing and where do you think we're going to go? 

Jonathan: I think these are all great things. I think that embracing all of these things is going to give us the best chance to be more effective. And honestly, I think it's going to give people a better quality of life.

I think organizations that embrace these things early develop ethical standards and codes for how to and when to use them. It's going to give people the opportunity to attract the best talent because it's going to give people A better opportunity to specialize when the day to day things are being handled by you know, machine learning or AI, then you can have people who are really good with people who are really good in certain situations, focused on just those aspects as opposed to the administrative aspects that we all tend to get.

Down with [00:24:00] sometimes in the day to day of doing any job or any role. So I like these things. I hope that my organization and other organizations continue to embrace them. And yeah, I think that they mean that people will have you know, better quality of life amongst all types of organizations.

Nia: I'm starting to develop this idea that if we are moving towards ultra digitalism, we also need to balance that seesaw to, to ensure that we have hyper humanism as well. And I think that's very similar to what you're talking about is that this person centered human element that it's going to be very important for us to focus on that.

Jonathan: I would agree. 

Nia: Jonathan, if people want to get in touch with you or find out more about your podcast, how can they do that? 

Jonathan: Definitely the easiest way to do it is definitely socials, that's always the easiest thing. TikTok is John, J O N J Boone. And that's pretty much where I am on Facebook and Instagram as well.

Emails for corporate speaking or for if you just have a [00:25:00] question about something that you saw on my podcast I can be reached at JJ Boone llc@gmail.com. And if you go to any place that you listen to podcasts and you. Type in 'How To Fail' my podcast is right there as well. 

Nia: Amazing. We will make sure that there's some of those links are in the show notes.

And actually we have a new function on the podcast that if you do want to text the show You can go to the show notes and at the very top of the the show notes You will see that you can text the show So if you want to drop a line to john or myself, then you're very welcome to do that John, I've really had a good conversation today.

I've enjoyed having you on the show. Thank you very much for joining me 

Jonathan: I agree. Same thing. Thank you, ma'am.

Nia: Are you a chief executive or a senior leader within your organisation? If so, it would be great to have you join me on the podcast to share your journey, experiences and light bulb moments along the way. Drop me an email at info at [00:26:00] knowingselfknowingothers. co. uk if you'd be interested in having a conversation.

Francesca: The Knowing Self, Knowing Others podcast has a new feature. You can now send a text message directly to the show. Check out the show notes in your favorite podcast player. And in the top left of the notes, you'll see a link to text the show. Click on it to be taken to your messaging app and send a text directly to Nia and this week's guest.

Join the community and be a part of our learning journey.

Nia: Thank you for joining me on today's episode where we aim to develop self aware leaders around the globe to generate kinder, more respectful, and creative working relationships through reflection, recognition, and regulation. Head over to my website at knowingselfknowingothers. co. uk to sign up to my newsletter to keep up to date with my blog, podcast, and book.

Looking forward to having you on my learning journey.

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