North Star Leaders Podcast

Lindsay Pedersen

The world needs what only your business can bring. And as a leader, it's your job to deliver. But where do you focus?

Where do you direct your time, your team, your budget, and your emotional energy? We're learning this together on the North Star Leaders Podcast. In this podcast, I talk to purpose-driven leaders about the choices that they make to create audacious economic value while also realizing their distinctive purpose.

I'm Lindsay Pedersen, brand strategist, author of Forging an Ironclad Brand, and host of the North Star Leaders Podcast. Let's get to it. Today, I am really happy to be joined by Bill Glenn.

Bill is SVP of marketing at Esper, the device management platform. Bill, welcome to the show.

Bill Glenn

Thanks, Lindsay. It's great to be here. Great to see you again.

Lindsay Pedersen

It's great to see you. Okay, to start us off, Bill, what is the most energizing part of your job that those of us on the outside wouldn't know?

Bill Glenn

Yeah, I think just because of where we're at right now in our performance review cycle, for me, a lot of folks dread the annual performance review cycle. And how do we have that conversation? How do we help people skill up?

How do we think about professional development plans? For me, that's the most energizing part of the job. And I think that's just the way that I've tried to live my whole career is how do I think about those who came before me and helped me develop my B2B marketing skills and get me to where I've gone over my career?

And who's given me the hard conversations at the times that I needed them the most in order to advance in my career? And so we're right here in the middle of it at Esper, and I really am enjoying the fact that I'm having these conversations with our leaders, understanding where they're at in terms of giving that type of feedback and or direction to their direct reports, and playing a little bit more of a mentorship role on both how can you be a better leader and manager? And then what are the honest conversations you're having with the folks that you're managing about where they want to go, what they want to be, whether that's six months, one year, six years, whatever it is, you can start that professional development planning now.

And that to me is maybe the most exciting part. And then you augment that with AI, which I think is an interesting layer in of tech meets the people side. And that's where I think it gets even more interesting of not so much the how do you make that more efficient, but actually how do you ensure that the types of messages you're delivering are unbiased?

Because you have oftentimes a whole year's worth of data that you're trying to process. And then how do you have almost like a co-pilot alongside with you to be like, well, what didn't I ask or what should I have picked up in this performance review that I need to go back to my manager later on and ask about that because I missed it during that conversation?

Lindsay Pedersen

Wow, there's so much there. The nitty gritty, sometimes challenging conversations that happen during performance review times, those really direct, sometimes difficult conversations. Have you always run toward those or is this new?

Bill Glenn

I would say semi-new only because I've been in this journey for quite some time, about 25 years. But I would say that probably only five to maybe eight years max have I been more comfortable with myself in trying to gear up for that honest conversation and be more direct in a way that my directs or those that I'm giving feedback to actually understand that that's coming from a place of growth and development and support and ultimately love. I'll just say that, like you want to be able to help that person the way that I feel like I got helped along the way with hard feedback and sometimes really direct feedback that I was like, oh, I don't know.

I don't feel like I'm prepared to like handle that. But in hindsight, I'm like, if I didn't get that in that moment, I don't think I'd be at where I'm at today. So the answer is it's taken me 15 to 20 years in the world of being a professional to really understand that direct feedback is the most important thing you can give and be uncomfortable and sit in that conversation.

And the uncomfortableness has always been challenging for me, even to this day, leading up to those conversations. I get the butterflies in my stomach and then I have to reset in my head. What am I actually trying to do here?

Get out of my own head. This isn't for me. This is for them.

So try to put myself more in their shoes. If I say this, how might it be ingested or how might it be received as opposed to how am I delivering it?

Lindsay Pedersen

Wow. It's amazing you use the word love here. And I want to get back to that.

When you have the butterflies even now, but you know that you value what's about to happen, how do you kind of tap into the wellspring behind that, the love, the goodwill that is so motivating and rewarding? What's the reframe in your head to go from the butterflies to the sheer energy?

Bill Glenn

Yeah, I think it is actually your own personal experience that you go through. And so I actually try to reflect back on the times that I was given either that direct positive feedback or direct negative feedback, and then recognize like, how did I respond to that? And what about that conversation if I didn't have a good positive response and like, take it the way that I think my direct managers were intending it?

It's like, what was my role in that? And then also, if I felt like my manager at that time could have delivered something better, I just try to think about like, oh, I remember when I was sitting in that seat and I want to make sure I don't say this because that left such a negative impression with me. And I think there's still a way to deliver that message, but deliver it in a way that actually gets a positive response or is framed in a way that people understand that you're doing it to help them in their growth and development, not because you want to call out a weakness or a deficiency in what you saw throughout the year.

Lindsay Pedersen

It sounds like you're almost like you're channeling yourself in another moment when you are on the receiving end, and then that becomes the touchstone for what's that actual empathy in that conversation. Like that, what a tool.

Bill Glenn

Yeah, that's really well said. And I would also say, I'm trying to channel almost like, what was the manager thinking at that time too, in a way that I can be like, what did I really like about that conversation? And what do I want to make sure I sort of bring along?

I think about it almost like you have that head coach that has all these like assistant coaches underneath them. And then you start to see that spread throughout a league because you're like, Oh, well, they actually learned from sort of this tree of, you know, sort of the people management side of performance. And I want to be able to like, say, Oh, I took the best of a little bit of everybody.

Or I learned some really practical leadership skills from this particular leader in Seattle is such a small community. I feel like you can actually start to like, trace that back to be like, Oh, I think you actually worked with that person. Not because you say it the same way, but because your intent is similar, right?

And that you look back and you go, who are the people who really wanted to leave a legacy of being an inspiring leader as the one thing they're remembered by not necessarily like, how much performance as a company did we deliver? Yes, that's important. But as we all know, it starts with the people.

And if you don't have your people in that right mindset, and thinking about working together, because we're all on the same team, there is likely you probably won't hit your goals anyway, right?

Lindsay Pedersen

What do you think that you're like as a leader?

Bill Glenn

Again, maybe this is more recent, you know, sort of like last 10 years, I've flipped significantly from everything has to be perfect and I have to be the smartest person in the room to I want to make sure that we hire people that are smarter than me, different than us as a team, how do we think about bringing in different points of view? How do we think about diversity in our team?

And I think that the way people are viewing that is two things. One, I think they're saying, Oh, he's very transparent as a leader, I'm trying to be more direct in my messaging, so that it's, you know, not left a chance of like, what are our top priorities. But I think the bigger thing is, he's showing up authentically.

And to me, that is the most important thing is that if I can show that I'm not the smartest person in the room that I don't have all the answers like that infuses, I think, in the rest of the team like this, I want to contribute, I want to participate, and it's okay if I'm wrong. And it's more valuable to have your voice in the conversation than it is about, you know, sitting back because you're worried that whatever you say isn't going to be perfect.

Lindsay Pedersen

Yeah, what comes up for me with that is how much vulnerability that requires. And even when you started to say, it used to be that I wanted everything to be perfect. And there's so much fear that drives perfectionism, right?

Like, it's such an impediment to vulnerability. I mean, not vulnerability for its own sake, but vulnerability, because it unblocks this heartfelt leadership that you're describing. What happened that allowed you to overcome that fear?

Or do you still have the fear, you just ignore it?

Bill Glenn

You know, for me, it's always going to be there. I think it's just the way that I was raised and just trying to be living up to other people's expectations. And I think I am challenged by that every single day.

Like, how do I show up in a way that it's okay to be vulnerable? It's okay to be wrong. It's okay, because you're going to make mistakes, but you need to just own them.

That's a daily practice for me. And I'm far from good at that. And I've actually started to recently trying to stop using the word perfect.

Because, you know, as they say, right, perfect is the enemy of good. And in that way, I'm like, why would anybody try to drive for perfection? Because that is not the end game.

It's not the goal anymore. So I think maybe that's the key takeaway for me as I show up each day is, what am I going to like, I actually tried to do a walk every morning. Now, there's a little of a gratitude practice that I do on the walk, just to notice sort of what's around me, because we live in a beautiful area of the Pacific Northwest.

But the bigger thing in that moment is to say, you know what, life's going to throw at me some really bad stuff today, most likely, or not. But it's probably going to happen at some point, if not today. And it's not like a defeatist mindset.

It's more like this pragmatic mindset of when the bad comes, recognize there's good along with it. And the two together are what is called life. And so much of my previous living was like, create perfection, create perfection, and nothing can go wrong.

And the more guardrails and the more stress I put on myself to try to make that true, the less likely it was going to happen. And the more negative impact I think it had on those around me and even in myself internally.

Lindsay Pedersen

Wow. I mean, it's interesting, because I love that you're trying to stop using the word perfect and perfection and perfected. I think I'm going to adopt this practice of yours.

Because well, number one, it's an illusion, or it's an asymptote. And B, it blocks you from people, right? It blocks you from connection.

Maybe it's because it does come from fear. Leadership, it's really just people. It's connection among people.

And if you kind of hold the bad with the good, the hard with the easy, and sort of banish the idea of the goal is all good, all easy, all this, all that, then it allows everything to be more rich. It's so interesting how our brainstem is so smart, like it will detect dishonesty, because it benefited our species for us to be able to detect dishonesty. If somebody in the tribe set was dishonest and said, there's a water source over there, and they're lying, that could be the death of the tribe.

And so now as leaders, or as people in an organization who are looking to a leader, we have that same thing. We feel that. And this is kind of related to something else I wanted to talk to you about, which is resiliency and mental health.

How has this interwoven with the kind of leader that you are, that you want to be? How do you bring that in?

Bill Glenn

Yeah, I'm going to use a recent example, and we actually haven't gone through it yet. But the thing that I've been going through most recently, I've been turned on to a couple of different organizations. One is Scott Barker, and he has the Wake Up Call podcast now, and it's really about folks that are trying to reset and sort of have been in that hustle culture.

In his case, he suffered from workaholism, and he took a year off, and he's been traveling, but he's coming back with the podcast and writings, and he's on Substack now. It really is about slowing down to speed up and kind of being more self-aware and kind of recognizing that while AI is inherently good, there is a lot of risk with it if you don't manage that tool and that process the right way for you as an individual. So the Wake Up Call was number one.

And then something that I've been recently looking into, and by the way, this is not self-promotion or promoting these organizations, I just believe in them, but there's an organization called Second Harvest, and that is put on by Richard Banfield and Devin McDonald, and they're based out of Boston. And they're doing retreats now for those who are looking to find their next phase of life, and what does that look like? And sometimes that can come in your 30s, and sometimes that comes in your 50s or 60s.

But either way, I think there is sort of this Wake Up Call meets Second Harvest of whatever got me here isn't going to get me to the next level. And I think that that's the mental health kind of movement that I'm trying to foster is all those things that we thought we were rewarded for, what our parents sort of tried to push on us as this is what success looks like. That's not it, at least for me.

And I always speak for myself, but it ties all the way back to perfectionism and what was deemed as like, this is what's deemed the social norm. And over time, I've just been like, you know, some of this stuff doesn't work for me. And how do you do this without necessarily being a rebel, but also like be true to yourself and say, you know, if this isn't working for me, like, don't push that on anybody else.

But don't live in that just because society suggests that that's the only way that you should or could live to be accepted. So for me, the mental health every day is sort of wake up of what are my values? What do I care about the most?

How do I make sure that I am trying to do my best to live up to those values, knowing that I will fail throughout the day and throughout the week and throughout the year. But if I can just keep trying to show up as my best self, and maybe the biggest part of the mental health is like owning my mistakes and admitting when I'm wrong. And I'll just say like, maybe that's been the hardest part of my entire life is like just being able to say, you know what, get rid of the perfectionism.

And in the moment when you're wrong, just say it and own it and move on. Because those two are always in incongruence. And until I flip that switch to again, perfectionism is not the goal.

It's the ownership of mistakes. And then what did I learn from them? And how do I grow from that?

That maybe is the biggest shift in my mental health. Because if I live in that world of perfectionism, I will continuously fail, maybe for the rest of my life. So I was like, you know what, I can't just say like, it's black and white, and I don't do that anymore.

But every day, I'm going to try to pivot more towards the ownership of mistakes. Because that's the only way that I can forgive myself at the end of the day and be like, I'm just human. I'm just trying to do the best that I can.

Lindsay Pedersen

It's interesting how much mental health and just living the kind of life that you want to live, how much it involves deprogramming. Yes, you know, messages from our upbringing, from social conditioning, what are the cultural norms that you grew up with that are surrounding you, and like tapping into something that is true for you and is in some places and in sometimes downright counter cultural. You know, if we were having this conversation 30 years ago, and said that perfect is a word we're going to banish from our lexicon, it would be kind of weird, right?

It's interesting how it's like, there's like a stripping of things that don't serve. And that's our growth edge as people. And therefore, as leaders, it's not about adding something, it's about removing something.

Bill Glenn

That's right. And I would say that maybe that was the most interesting part of Scott Barker's conversation so far, is that he's in his thirties. And so I think a lot of times people are like, oh, well, you know, you're in your fifties.

And so that only comes with wisdom of age and experience. And it's like, no, not necessarily. Like other people are recognizing this now.

And I do think sort of the trajectory of AI is creating that additional amount of pressure because of the condensing of time and the condensing of sort of like seeking out to getting answers has been so shortened. You know, everything, no matter what age, what decade you're in, in our workforce, you're now feeling that same pressure and it's just hitting people at different times and at different stress levels or different points in their career based on, you know, how ingrained they are in sort of like making work their number one focus. And I've seen a lot of 20 year olds that absolutely could use a reset.

And I've seen plenty of 60 year olds who are maybe kind of hit that phase one of their career is done, but then they're like, now what? And if I'm not in tech anymore, like, how do I stay relevant? Especially for folks like myself who have been in tech for 25, 30 years, I'm doing a complete rethink on like, should tech even be part of my next phase?

And maybe it will be in some way, but it doesn't necessarily have to be because I want to, I guess, open the aperture a little more to what else is out there and what is going to serve me well and how can I take my talents and give that back to those who I'm surrounding myself with much more so. So a lot of people call that servant leadership. I don't view it that way.

I look at it as like, we only have so much time on this earth. And when I look back and I think this is an exercise a lot of folks do is write your obituary now. And it's like, what do you want to be known for?

And that is helping me to like try to weed out some of the things I don't want and get more focused on if there's only so much time left, what do you want to make sure you do? And it's not, you know, we all talk about, oh, you want to travel and do more and you know, it's not bucket list. It's like, no, living with intentionality right now so that when you look back, you go, I didn't wait until my 70s or 80s to do that because maybe I don't even get there.

No matter where you're at, whatever age, when you have this epiphany moment, I think it's like, listen to yourself. That's the wake up call and take advantage of it while you're feeling it.

Lindsay Pedersen

Yes. So talk to me about mentorship. And I mean, mentorship that you've given and received over the years and what it's meant to you.

Bill Glenn

Well, first of all, I'll just say that that's the gift that I never realized growing up that was available to me. And I was fortunate to receive that gift. I would say it was almost sort of like forced upon me by, you know, a friend who became a mentor who really I sort of look at as like the sage for me over the course of my go-to-market career.

His name was Bill Lawler. And hopefully he hears this at some point because he knows how valuable he has been to me in my career. And he actually ran a consulting shop on the sales side, but he was a math major in college.

And he also worked at, I believe at both Apple and Dell in the eighties and helped grow their sales organization, both sales organizations. And he really took like that data-driven approach long before people started talking about data-driven approach. But as a math major, he's like, you can sort of break all the B2B go-to-market, you know, the funnel management, if you will, down to the numbers.

And him just kind of taking me aside, being like, hey, your gut has gotten you to this part in your career. And like 95% of the time you're close. You're not always right, but like directionally you're right.

But if you don't have the data to back it up, you're not going to do well in board meetings and you're going to do well with CEOs. And we need to like kind of do a math 101 exercise, but apply to the B2B funnel. And I remember him sitting me down and I was like, you know, what's this guy talking about?

I'm in product marketing. I'm not even in demand. I don't even understand why he's telling me this.

We have a demand person, go talk to that person. And maybe that was the biggest moment in my career where I was like, you know what? I don't know everything far from it.

And this person didn't just give me a math lesson. He gave me a life lesson for asking for help, even when I didn't know I needed it. And I think that changed my whole mindset of like, it's okay to ask for help.

And it's okay to like get curious about things that you don't know, and then go ask the people who have lived it, breathed it, then you may still believe you're smarter than them, but they actually have a perspective that you do not have. And you need if you want to be a better people, leader, manager, and just doer of your job every single day. So to me, that's where it started.

And once I figured that out, he actually was there to support me. And he was really, again, kind of going back to like, he was showing me love in a way that I didn't even know how to ingest and take in and thank him for for years later. But once I did, I was like, man, that might have been the best gift that I've ever received in my professional career.

And I just said, how do I then translate that to other people? Because that moment for me was a huge unlock moment. And I want to be able to do the same for others.

And so I was fortunate enough to get introduced to the University of Washington's Foster School of Business MBA formal mentorship program. I participated in that for five years. And it was the most rewarding thing that I've ever done in terms of watching folks, most of them were in the professional environment for a few years, but we're going back to get their MBA.

But a lot of times they were missing sort of the people skills or that sort of like the what's the next level of leadership that you can't get in the classroom. And I tried to build a lot of my mentoring around what does it mean to be a better networker to be a better connector to be in a sort out in the world sharing what you know, whether that's through social media or being comfortable speaking on stage, you know, think about that give back mentality, the more you put yourself out there, even though it's uncomfortable, the more likely you're going to get back and you're going to build a really strong professional network that's going to help you along the way. So that to me was maybe the most rewarding five years that I've had, I will say, like, I think I'm going to go back and do it. But what I have done is through other b2b marketing communities, is when I kind of introduce myself, and they say, you know, what are your superpowers?

Mentorship is almost the first, you know, it's not the first thing, it's within the top three that I list. And I can't tell you how many informal mentorships that I've taken on from that. And I have a couple going right now.

And there's two gentlemen that I'm working with that are just phenomenal in their own right. But they're just, you know, so they've never been at that true marketing leaders level, or they've only done it for about six months. And I love kind of putting myself back in their shoes of like, Oh, yeah, I remember when I was feeling that.

And here's what I did both good and bad. So take what you want from that. But it's really interesting to sort of see other people ask for that help.

And they're doing a proactively where I didn't. So I'm like, clearly you all are further ahead in your professional development than I was in mine. But again, it's been richly rewarding, even if it's not an informal program.

Lindsay Pedersen

Yeah, I mean, how satisfying to see that. And I love the openness, allowing these people who are receiving mentorship may be more open to the mentoring than you were at one time. And also just kind of like letting that be what it is.

Wow. Oh, my gosh, Bill, this has been such a great conversation. I have some just sort of fun, rapid fire questions as we finish.

Okay, I've got five of them. One word answers. What time do you wake up?

Bill Glenn

6am.

Lindsay Pedersen

When you travel, do you arrive at the airport early or just barely in time for the flight?

Bill Glenn

Just barely. I kind of love it. It's like a little adrenaline rush.

Lindsay Pedersen

What's a small habit that's had an outsized impact on your life?

Bill Glenn

So the most recent one that's having a huge impact is trying to go to bed at nearly the same time every night and getting a minimum of seven hours of sleep. And it's a night and day difference for me. If I get those seven hours and mostly uninterrupted, it actually helps with my mental health as well.

Lindsay Pedersen

Back to basics. Get sleep. What is a purchase under $50 that's improved your life more than you'd expect it?

Bill Glenn

Under $50, I would say.. I don't have it on me, right? Oh, actually, I do have it on me. This is my trusty Timex Ironman watch.

It used to be $50. Maybe it's a little bit more now. But I love it because it has all the things that you might want on it for running and tracking things.

But it's also like 1980s style tech, where it's like, it's just basic. And honestly, like, once I put that on, it just reminds me of like, make sure that you do something active. And like, set your day off right by, you know, getting some steps in or going to the gym.

And it is my alarm clock. Like I actually have a separate alarm clock that has an alarm on it. But I just choose to use this one because the alarm on it is like the thing that my body is trained to like, wake up and I wake up with a positive vibe.

Lindsay Pedersen

It's like so analog. It's not like listeners can't see it. But it really is like a 1980s.

You could picture Rob Lowe wearing it in St. Elmo's Fire or something. Okay, last but not least, what is the most recent song you've had on repeat on your phone?

Bill Glenn

This is fully dating myself. It's Harvest Moon by Neil Young.

Part of it is because I'm trying to get back into guitar again. And it's a song that I think I can play. And part of it is actually bringing me back to like, sort of in my teenage to 20s years of kind of going off on my own and becoming my own person.

And that whole sort of classic rock era was kind of what I grew up on. And it also what kind of carried me through my 20s when I moved to San Francisco on my own, and tried to figure out life as no longer a Midwesterner, which was pretty awesome, but also pretty scary. So fun to have those memories come back with that song and that genre.

Lindsay Pedersen

Tapping into your younger self.

Well, this has been such a soulful conversation. Where can people find out more about you if they want to connect with you online?

Bill Glenn

Absolutely. So predominantly, it is LinkedIn. And so it's William W. Glenn with two Ns is my LinkedIn handle. And yeah, happy to connect with folks there. Awesome.

Lindsay Pedersen

Thanks so much, Bill.

Thanks for listening to this episode of North Star Leaders. Make sure you don't miss an episode by subscribing on your favorite podcast app. If you know of a North Star Leader whose insights would be valuable for this community, please message me on ironcladbrandstrategy.com.

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