Shift & Thrive: CEO Insights on Driving Change

S&T_Bill Flynn
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[00:00:00]

Natalie Nathanson: Today's guest is a growth advisor and business strategist with more than 30 years of experience helping companies of all sizes navigate lots of change and complexity. He served as a vice president of sales in multiple roles, chief marketing officer twice, and led a division of a hundred million dollar IT services company.

Along the way, he drove numerous [00:01:00] successful exits, IPOs, and a major company turnaround. He spent the last 10 years leading his firm, catalyst Growth Advisors as an executive coach and consultant focused on helping leaders build stronger teams through smarter decisions. And he's also someone with far too many professional certifications and credentials for me to list right now.

I've known him for many years and I'm so excited to have him on the podcast. Bill Flynn, welcome to the show.

Bill Flynn: Thanks for having me on, Natalie. Looking forward to

it.

Natalie Nathanson: That's great to have you, and I know you have worked with many CEOs and leadership teams over the years, and I would say you bring a, a calm but direct energy that I would imagine like really helps executives reframe how they think about leadership and strategy.

Uh, which I view as, uh, you know, the, the very thing that we need in the somewhat chaotic environment that we're currently living in. And so, very much looking forward to talk with you about what it means to lead through change and kinda how to do that, uh, quote unquote the right way in [00:02:00] today's environment.

Start us off. I thought we would start with maybe a more personal, real world example of your own, uh, and I know you have a good one. So it was an experience where you took over a company, uh, right as things got maybe a bit tumultuous and then kind of how you led through that. So can you take us through that story, you know, first what happened and, and how did you respond?

Bill Flynn: Sure. Um, well, uh, as we've talked about, so I did 10 startups over about 25 years, and between startup five and six, I took some time off. And during that time I would, um, because I was relatively well known in the VC world and whatever, I would get calls from friends and people, Hey, can you come help me?

And one of them was this company, um, where the, um, fractional CFO said, Hey, this guy really needs some help. Can you come give him a hand? And so I met him, um, and he said, look, I need you to make me as big as he possibly can. I wanna sell this thing. I'm getting tired. He's been doing it for, I don't know, nine, nine years or something, and kind of doing it all on [00:03:00] his own.

And so I came in and, um, helped him, you know, sort of build out his sales infrastructure, worked on some other things. And then about a year or so later, the company was sold, uh, to mindshift, which is an IT services company here in the United States.

Um, and what we were doing was, uh, it was email hosting.

This was before Gmail, before Office 365 was actually the precursor to Office 365. Um, so I was asked to take over the division when he left. And my first official day, which I think was the fourth or 5th of January in 2009, I, I like to say it was the best and the worst day of my professional life, uh, because the email didn't get delivered to anybody, uh, for like two and a half days.

Um, it, it sort of worked, but it didn't really work very well and we lost like a thousand customers immediately and I had to go around the country and try to save some of our large partners. Some of them were really big, [00:04:00] you know, billion dollar partners, Ingram Micro for the tech folks out there. And, um, and a couple others.

Endurance who the company that bought, um, that bought, uh, what was Roving software. Um. And so what I had to do is I was like, okay, we gotta figure this thing out. Now, the company that bought us Mindshift was already working on the infrastructure and et cetera, but they had to accelerate that. Um, but I had 60 people working for me.

You know, I, I still had seven, 8,000 customers, so I had to do something to sort of make this thing better. So I took the team that I had and I said, okay, uh, I said, look, this is my first time I've been doing this. I've never run finance before. I've never run customer support before. I've never run, you know, tech, the tech side, I'm geeky, but you know, I've never developed a network infrastructure.

So I said, but you know, I, I have an idea of what I want it to look like when we're, when we're out of this mess. And so let's discuss and debate and decide what that looks like. And then I want each of you to draw a [00:05:00] roadmap from where you are now to, to there, and what you need from me and from us to help you get there.

Um, so they did that, um, and it worked. You know, wonderfully, uh, it was for those who know the world, it was sort of like a, an EOS kind of model that I put together. You know, I sort of said, here's what you know, here's what I'd like to do. Here's the process I want to go through. Um, and, uh, the numbers are great.

If you look at my LinkedIn profile, it has on there, all the stats were great, but the best part was two of the people I worked with sort of said the same thing to me when I left to go do the next startup about 18 months later or so. Um, and they said, I just want you to know that thing. You made me do that roadmap.

Hated it. It was really, really hard, but I'm so glad you made me do it because now I know how to do it right. It was sort of teaching people how to fish. Um, and, uh, so, so that went, so that [00:06:00] sort of put a thing in my, the back of my brain, which is why I'm doing what I'm doing now, uh, is that I, I wanted to do that again.

You know, all the other stuff was great. You know, we, we. We increased customer service, we doubled the size of the company. You know, I didn't lose any of the 60 employees who were, who were getting yelled at. Um, did all sorts of fun things with them. So, so learned a ton of stuff. Um, but I wanted to have that experience again with those two guys, right?

Where, where I can help someone really, you know, teach them how to do stuff. So I went on, I went on and did four more startups. These were, they were all miserable. Uh, none of them, I don't, I don't think any of them is still around or they're certainly not around in the same way that when I was there. Um, but in 2015 I sort of said, do I wanna do an 11 startup or not?

Uh, and I said I would do one, um, but I needed to figure out if I could interview a founder so I could find the right one. And I couldn't really convince myself that I didn't know how to do that. 'cause as you know, all founders are [00:07:00] sort of crazy. They have to have this reality distortion field, et cetera.

And, um, and it's much too easy to start a company now than it was when I first started in the nineties.

Um,

so I said, you know, let, what can I do to, to have that experience again? So I went out and looked a bunch of bus business operating systems. I did look at EEO SI looked at, I looked at like, I think five or six different ways to do it, and I settled on something called Scaling Up, which I became certified in.

Um, I'm no longer in scaling up, but I still use a lot of the principles there. So that's sort of how I got to where I am today. And I learned a lot of stuff. It's funny, I I, I, I was talking to someone the day on a podcast and said, I, I wish that I knew then what I know now, because it would've been a heck of a lot easier to do some of the things that we did.

Um, we just make it so hard on ourselves to run businesses and, uh, there there's a better way to do it. So that's what I'm trying to teach you,

Natalie Nathanson: Yeah. for sure. I often talk about, uh, kinda reinventing the wheel and when I'm doing it by accident and when [00:08:00] I'm doing it deliberately. right. And I think in my earlier years running the business, often it was reinventing the wheel unnecessarily and things that other people had already figured out rather than kind of when you're doing it because you have a different vision or a different approach of how to, uh, how to address something.

And then it becomes kind of part of, uh, your kind of leadership secret sauce or your company's secret sauce or something to that effect. Um, I wanna come back to, um, you know, the, the roadmap and exercise that you, that you gave your team, because I do love that. And like right away you can imagine the kind of like ownership and accountability the team felt and, uh, really the, the kind of role that I'm sure everyone felt they had in, uh, reaching that vision.

Where did that idea come from? I know you said there was kind of some EOS in your thinking, but it sounds like there was more to it. Like how did you as a leader go about figuring out that approach and were the people around you? Talk to me about that.

Bill Flynn: Well, I wish I was that savvy. I didn't know

EOS existed at the time. This was 2009. Right. Um, so I had no idea. So I was [00:09:00] inventing something that was already invented, you know, sort of the, the wheel thing that you mentioned.

I Yep. made my own wheel. I didn't need to, I could have just sort of grabbed what they had or scaling up or something.

But, um, so I've been doing a lot of reading. I've always read about business since I was, you know, for 30 something years now, and I had two or three really good CEOs. And so I, I took some things from that I learned from them that I really liked and, and, you know, some of the work that I did, and as I said, I sort of cobbled this together.

Um, you know, I said because I was in a situation where I, I, I didn't know anything. I was ignorant, right? I, I, there were several parts of the company that I had no idea how they worked or, uh, et cetera. So I was put in this position that I had to not be the answer person. Um, I had to be the person who set up the environment.

So we could work together. Um, and that was, you know, that was sort of what I did. And, and I just took a, a bunch of things that I, I, I remember [00:10:00] when we, um, I, I created a, a, um, a meeting rhythm, right? We would meet once a week and, you know, I had everyone write a report and we'd meet on Monday at 10 o'clock or something, and I said, it's, you know, the report needs to be in by five o'clock on Sunday night.

You can do it even before that, but at least it's gonna be. Be done before that because I want everyone to read what everyone else is writing.

Um,

and I remember the first meeting, uh, I can't remember who went first. Maybe it was Brian, and he starts reading his report and I just sort of, I'm, I'm a bit cheeky, so I sort of stopped him and I, and I said, Brian, I said, do you think I don't know how to read?

And uh, he's like, what do you mean? I said, I said, I read your report. I don't want you to read it. I said, you know, I want you to give, if there's something in there that's important for, you know, all of us or some of us to know that would help them do their job, great. Or if you have a question you have on anyone else's, whatever, do that.

Um, so, you know, I early on said, look, this isn't just a rehashing, this is, this is a working together model, right? This is where we're, we're helping each other [00:11:00] and we're challenging each other and supporting each other. Um, so each of us can reach a roadmap, um, destiny or destination. Um, so I did that, you know, I did, there was one really cool thing we did at, um, be Free, which we, uh, you could sting somebody.

And I sort of took that and, and the, the, um, the company that was sort of the container company was called Group Spark. So we invented this thing, or I invented this thing called sparking someone, uh, where, uh, anyone could spark someone else, uh, based upon really a service environment, right? So, so if, if you, if you see someone doing something really great for a customer or doing something for someone who's doing something great for a customer, anyone can, you know, shoot out an email.

Say, here's what I was assuming Natalie was doing this. I just wanna recognize Natalie for this, and you have to write quickly email. Um, and then once a month we would get together and all the ones that.

Um,

that were, that were [00:12:00] sparked, we would, um, if they wanted to, they could come up to the front of the room, we would give them a little ribbon.

Um, someone could tell a story if they wanted. Um, we did that every month. And then at the end of the year, I think we, you know, we, we gave them, I think, can we give 'em like a day off or something? And then at the end, we gave them, anyone had like a weekend, right? Uh, we pay for a weekend for them and their partner to go do something.

Um, and that was, you know, this is a bunch of, probably some, we were between 30 and 60 years old. Um, and so, you know, it was kind of hokey, right? With the little ribbon and stuff. But I gotta tell you, it was a cube environment and most people were cubes. And if you remember, if you remember the cube world, right, you'd sort of walk around and, and you'd sort of go to the entrance and that's where you could sort of see where they were.

Maybe you could see the top of their head if the cubes weren't too high. And ev almost every cube when you made that turn, that's where they put the ribbons. They wanted everyone to see, like the first thing they see is like, how many ribbons I got. Uh, so it really turned out to be a really [00:13:00] cool thing and people loved it.

Um, and it was a lot of fun. It was, and it wasn't, it wasn't me or anyone else. It was, you know, it was everyone. So it was sort of this way for everyone to sort of feel connected and, and to support each other. Um, so it was, uh, it was a, I don't, you know, so I just sort of stole stuff and put it together in my own way.

Um, that's sort of how I did it. Now I do it in a more, much more concerted way. Um, but that was the beginning of it.

Natalie Nathanson: Yeah. Uh, which like, it sounds like it really came out of necessity and then, but like, worked really well for you and helped you kind of develop some new, uh, uh, kind of new motions. I'll, I'll say, um, I'm curious to ask, you know, in your role there as, as CEO, it was something that, like you said, you were new to the business, didn't know kind of all the inner workings of the business.

A topic I've been thinking about is, you know, for the world ahead, like founders that come from the industry they serve, or professional services leader that [00:14:00] uh, kind of knows how to do a lot of the things in their business. Are those the ones that are better equipped for the years ahead, or are they at a disadvantage?

Like I've seen, you know, I'm speaking from personal experience too, you can get more mired in the details. You know, you hire differently. Um, any perspectives on out of how that might help or hurt, uh, a leader based on their, their background business they're in?

Bill Flynn: Sure. And I'm gonna steal from others, so, so this is not, this is not new, right? Michael Gerber wrote about this 50 years ago in E-Myth. Uh, you know, the technician has to understand that being great at making pies or whatever. I can't remember the story. I think it's something about apple pie or something.

Was, the story in the book has nothing to do with, with running a great business. It's a completely different set of skills. Um, but unfortunately, you know, what we do is. Especially founders, you know, you and and leaders of companies, you have to have confidence, you have to have an ego, but sometimes it gets in your way because you think just because you're good at one thing means you're gonna be good at the other thing [00:15:00] and you can't imagine why you're not good at it.

Um, and if you don't check in with others, like I know you're in an EO group and, and, and I I've talked to Vistage folks, unless you talk to others, you don't realize how little you know, or, or you know, the things that you don't know because you just think everything that you know is, is everything there is to know.

Um, so you act in this, in this way that really works against you. Um, because, and, and, and, and you know, and I even equate it to a larger sense is, is, is that, you know, you and I both grew up in the United States. We probably went to similar schools. You are rewarded for having the answer. You are rewarded for knowing stuff.

And that. Is just gets ingrained in you and so it feels odd when you know. To put yourself in a position where you don't know something or you have to admit that you don't know something,

um,

and you know, in, in a contrarian [00:16:00] way, that's actually the best possible thing that you could do to be a great leader, right?

Because your job is to now create the environment for other folks. To really run your business for you. 'cause your job is not running the business anymore, right? It's as, as the business grows, you should be removing yourself from the day to day as much as possible. Um, because the, the, your job is to create the future of the business, which is a, an innovation

act. It's,

it's an act of insight. And if you're busy all the time, you don't get insights. Right. And I, I, I asked this if, I can't remember if I asked you this over the years, but, and I apologize if I have, is so an insight happens when your brain actually fuses two things together that weren't fused together before.

And so those are your best ideas, right? Those are your ideas. So when, so Natalie, when you get your best ideas, what are you doing?

Natalie Nathanson: I am usually running, occasionally I am showering, I am not sitting at my desk, you know, typing away, checking email, all of that.[00:17:00]

Bill Flynn: Exactly right. So that's when, uh, when your brain is quiet

is when you actually get

your best ideas. Um, I had a guy yesterday, he's like, my best idea. He's like, I just got a really good idea and it was just when I was waking up,

uh,

I said, that's exactly right. 'cause your brain isn't really engaged in anything yet.

And so if you're, if you're, if you're the technician, if you're the doer, you don't give your, you never give your child your, your brain a chance to relax.

Um,

so you have to fire yourself from the day to day. And you know, you can't, you'll never completely fire yourself from the day to day. I mean, you still have to keep in touch, you have to have your meetings, et cetera, but you don't have to do it nearly as often as you do, as you do.

When I was a Vistage speaker, I would always ask, how much time do you spend in the company versus on the company? It was almost 80 20 in the room. And these are enlightened leaders. These are like people who are always trying to learn and grow, et cetera. And they're still spending 80% of their time. In the business, you know, I said, you know, my job is to get you to flip that, to be 20 in and, and 80 on, because that's when the business will start to accelerate in that velocity.

Eventually you will [00:18:00] be the reason why the business doesn't grow. Um, you know, there, there's the thing Vern Hard says all the time, which I really like, which is, you know, the bottle, the, the neck is at the top of the bottle, right? The bottleneck is at the top right? And you have to remember that, and your job is to, is to, you know, make it so you're not the bottleneck.

Uh, and that makes it very difficult for people because, you know, we pride ourselves. It's this identity of, you know, I make decisions, I solve problems. I am, you know, I, you know, it feels good. You're helping quote unquote helping people, but in the end you're actually not helping them. Um, so it's a very counterintuitive kind of thing.

And, and, and, and in the world that we're in today, which is getting stranger and stranger and faster and weirder, um, it's, it's actually accelerating. That issue for you as a leader, even where 10, 15 years ago it, it was a problem, but it wasn't as big a problem, but it's becoming a much larger problem.

Natalie Nathanson: Yeah. That's super helpful. Um, I wanna come back later to that theme around, uh, kinda why this becomes so [00:19:00] important in the world we're heading into. Um, but while we're on this topic of, um, you know, what the, you know, what the CEO and founder, uh, you know, needs to, needs to do kinda how to be, to surround themselves, I guess, with kinda excellence or people that know the functions better than them.

I'll share my own personal experience. You know, I see this all the time in the go to market arena. Um, and we work with some very, uh, kind of talented expert, a lot of like technical, uh, uh, executive leadership, um, who know a lot about, um, their, their industry, their field technology, not always as much on the, on the go to market side.

Um, and so we see this might be a place where CEOs can misstep is, uh, not always having the appreciation for what goes into the go to market strategy and, uh, kind of the foundations and how do you align kind of all of those motions. Um, and I know that's an area where you have some strong opinions and, [00:20:00] uh, also kind of deep, deep background, uh, earlier in your career.

Um, so I mean, what do you see as far as kind of where CEOs, uh, kind of what, what they might get wrong, I guess, when it comes to go to market, especially in like, the kinds of times, uh, we're living in today?

Bill Flynn: So,

um, my experience is we, we almost always solve that problem from the middle. Uh, which then gets in the way, right, is, um, a great go-to market strategy is a well-designed market strategy. Um, just like a well-designed house, um, or golf course or whatever, something where you put a lot more thought into it.

Um, we, we. Um, misconstrue starting with the entire journey. And we feel like, you know, we, we need to start quickly. And that, that makes, you know, it's, it's, it's, that's what should be rewarded. And I'm, I'm constantly telling my, my leaders to slow down and right, and actually don't start so quickly. Make sure that you've actually thought through [00:21:00] some things first, had some conversations, um, understand, you know, um, what causes your best customers.

Not all your customers, but your best customers to buy from you. And when I ask this question, everyone has an answer. And then I ask, well, how do you know? And those answers are less convincing, right? You know, well, I just know it's, you know, it's, uh, oh, I've talked to my customers and I said, well, what do you talk to 'em about?

I said, well, I ask them what they want. And I said, then what do they say? And they say, tell me what they want. And I said, well, is it actually what they paid for? Well, no, you know, so, 'cause. We, we, we as consumers, we buy differently than we're sold to, right? There's a supply side and a demand side,

and

we don't really understand, not enough of us understand the demand side of selling, right?

And marketing is that, uh, we, you know, we have these, and I'm not sure what your model is, right? But, you know, I, I always focus on, hey, it's, it's awareness first. Then there's interest generation, there's [00:22:00] qualification, then there's some sort of, you know, um, needs awareness, you know, needs analysis, et cetera.

Then you demonstrate something and then you go through the negotiation close, et cetera. Um, and that's how we sell. But that is not how people buy, right? People buy, um, through two real,

two

main processes. One is that,

You know,

there needs to be some sort of struggle. Some sort of, uh, dissatisfaction that they have to have.

If there's no dissatisfaction, they're not going to move. We don't like to move the brain like status quo. You know, a lot of things have to have us move and we can't assume just because we think our product is awesome, that people are gonna think the same thing. And I would say this to folks all the time, and I would ask them, you know, why do people buy from you?

And basically the answer was, because we are awesome. And I say, I'm, I'm, I'm, I'm sorry to disappoint you, but people don't really care how awesome you are. They only care how much your awesomeness does for them,

Right.

It's a very self-interested model. So, you know, we, [00:23:00] we have to have this dissatisfaction.

Um, and then, you know, so there's this model called Jobs to be Done, which, which has this process that people go through, which is, you know, there's, you know, you have to have some sort of thing that sparks your interest. Either it's a push or a pull, right? And if it's a push, it's like, you know, you know, something broke or you're dissatisfied, or something's working, or whatever that's pushing you, or you see something that.

Like, Ooh, that's looks good. Um, but then you just sort of think about it for a while, right? And, and you're, and you're not really actively doing anything. And then something else happens. Maybe, let's say my, my example is always like a lawnmower, right? It, it, then the lawnmower finally breaks, or it's the third time you've had its service and you're like, I just gotta get a new lawnmower.

Um, and now you start actively looking for lawnmowers. Um, and so you're, you're, maybe you're going to a shop or you're seeing things you're advertising, et cetera, and then you, you begin now the decision process, you n narrow it down to two or three different things. But what also happens is in that model is, so that's the push and the pull, and that's moving you [00:24:00] towards progress.

But there are also two aspects, two forces that are causing you not to move, which is habit and anxiety. Which is, you know, well, you know, these new lawnmowers are really fancy. You know, I'm I gonna look stupid in my front lawn if I don't, you know, know how to do it, or, you know,

Uh, it's probably gonna be a lot more expensive to fix because there are all these moving parts.

You know, you have all these reasons to not do stuff and we, as we as sellers and marketers don't realize that that's part of our process. We have to help them have to ease that anxiety and that habit. And if you haven't done all that work. So that's my long way of saying if you haven't done all that work before you do your go to market, then your go-to market is now a guess and, and you're hoping much more for luck.

Um, and, and you could have made it a lot easier on yourself if you really just spent, you know, one or two weeks probably doing some work up front

that would've changed what you did.

Um, and the story I tell here, and then I'll let you talk. Um, the story I tell here is [00:25:00] I worked at a company called Live Vault, which was an online data backup company in early two thousands.

And when I first came in, um, as the head of sales. And they were already nine years old. They had customers, um, they were doing, you know, they were doing okay, but they were sort of, you know, stuck. And I said, look, I, I just gimme two or three weeks. Uh, I wanna do some research. I wanna go talk to our best customers, and I wanna know, I'm gonna figure out why, you know, why they bought from us.

It'll help me understand how to organize the team, how to hire people, et cetera. And I went through this interview process and the, there was one question on there which someone gave to me, which I just, I, I love and loved, which was, what is the most valuable thing that you got from using our service? And these are small to medium business owners, you know, had lots of things to do.

Um, and I talked to, I think 17 people, uh, over a couple of weeks, and 12 of them said the exact same words to me when I asked them that [00:26:00] question,

which was

said it and forget

it.

However, when I asked the CEO, the head of marketing and sales, the head of marketing, the head of product, why do you think our customers buy from us?

They said insurance, which I still thought was a decent answer, but that wasn't the main reason they were buying from us. So we were selling them insurance, right? Because they're saying, you know, they're, they're gonna pay us a little bit of money every month. If the data, if the something happens to the, the server, they can get their data back, you know, uh, pretty quickly, hopefully all of it, et cetera.

Which, which certainly was in their mind. But the main reason they were buying was because they said, so, I don't have to buy tapes. I don't have to label them. I don't have to store them. I don't have to figure out which one's Monday, Tuesday, whatever. I don't have to do that anymore. I hit four or five buttons and that's it.

I never have to think about it again. Like, how much does that cost? Like they would pay almost anything to take that off of their plate. 'cause it would, it would, they would spend hours a week doing this and worrying about it and all this kind of stuff. And so. Sometimes we think we know why our customers buy from [00:27:00] us, but unless we actually go and ask them and, and figure out, you know, and really understand what they get from using our stuff, we don't know, which then affects your go to market.

Um, and I think I would say 80 to 90% of people, and you probably tell me more than that, don't do that work upfront. And they struggle on the go to market later.

Natalie Nathanson: Yeah. Yeah. I have so much I could respond to that. Um, very much, uh, aligned, I would say on the, you know, starting with the foundations, I know it can feel, uh, kind of frivolous or, you know, we just need leads.

We don't, like, we don't have the time to kind of go through the, the squishy stuff, the messaging, the targeting, the segmentation. Uh, but unfortunately it's so much more costly later to realize that you've kind of placed your eggs in the wrong baskets. and you've now aligned sometimes who you hire, right?

Like what your website looks like across your digital presence. Uh, so I think kind of undoing what has been done when you've moved in the wrong direction [00:28:00] is, uh, unfortunately a place where I see a lot of companies struggle. And then you're digging out of an even. Bigger hole, right? Because then you've already kind of sunk investments in the wrong places and, and all of that.

So I think all of that to say that, you know, making those investments upfront, um, and especially in the world that we live in with an AI and automation, like it's, it's never been easier to create something mediocre. It's never been easier to kinda scale up in the wrong direction. Um, you know, conversation I was just having, uh, yesterday, uh, with a prospective customer was a company that needs a website, um, and you know, was, uh, talking back and forth around the need for, you know, us as an outside organization to help work through the messaging.

Let's look at the competitive landscape, let's do that market analysis, which for us, I would say, you know, 80, 90% of the time, that is how we start working with a client is we help them through that. Um, and then the risks of only leaning on the internal executive team, like, oh, we know our markets. We know we can, [00:29:00] we can fill this in for you.

Um, your example of talking, why you talk to the customers, why you look externally in the market, and whether it's, you know, an outside kind of third party marketing firm or an internal marketer that kinda knows that discipline and how to go about that. Uh, kind of the right way. Um, just, uh, kind of pays, pays its dividends.

Um, and I know it can be a tough pill to swallow and you've got, uh, you know, pipeline, uh, revenue to hit, you know, all of

that. Payroll, a board, whatever. Um, um,

and I think too, you know, we were talking about the, uh, you know, how people buy, um, versus how companies sell, which I think is a very interesting one, uh, because I do feel like it's what you said has always been true.

Um, but the environment has shifted and today's buyers have. Very little patience for going through kind of playing the vendor's game if it's not kind of the way that they want to, uh, [00:30:00] learn about a company, get information, interact with sales. Um, and I think that's a place where, you know, some, some companies are very smart and attuned to that and, uh, trying to meet buyers where they are.

Um, but a lot of companies I think are really struggling with that.

Bill Flynn: Yeah. Well, so, and you bring up one other thing which we haven't talked about, which is, so we as buyers don't really know what we want.

Right.

It's not our job. It's not our job to, to say, I need you to make me one of these. Our job is to complain. And to, and to, and say, here's what sucks in, in, you know, or whatever, or, you know, I'm trying to, I'm trying to make this thing happen.

Right? As opposed

to, you know, the, the best example I always give is, is, you know, I I, I'm sure this, I made this up right, but the, it's Steve Jobs, right? What, this is what he was really great at, in my opinion, is that he didn't go and say, um, how do I, how do I make a better Walkman for you? Right? He went to someone and said, why do you have that?

What purpose does it serve for you? Um, how [00:31:00] is it making your life better? H how, what are you struggling with? What is, what disappoints you about it? Right? And then so he, he did, he would go through all these questions and they say, well, you know, I really like it. I, you know, obviously portable music, I, it's now, I don't need a radio anymore.

I can actually have my own music, you know, but, you know, let's assume it's the CD one. Um, you know, I have to have all these CDs right? And I have to carry them all around. I only really like two or three songs on it, and, you know, when I'm running it's skips and, you know, it's really big and bulky and, you know, whatever.

So he, so he said, okay, great. And, and, and. He went, finally went back and he said to Johnny E and he said, look, we want to make, he didn't even tell him what to make. He said, make me something that is a thousand songs that fit in someone's pocket. That's what we need to make, it needs to be Apple, right? So it needs to be super easy to, to use, got great design, all that kinda stuff.

And my understanding is that it took two years. They had, they designed it, but Toshiba didn't make the disc small enough to fit in a pocket. So they waited two years and then they, then they put [00:32:00] it up because they, they said this, he said, this is what they want. Right? Um, and clearly he was right. Um, we don't do that at all.

We don't, we don't, we, we think that the customer knows what they want and we really don't. You know, we never would've come up with the iPhone. We never would've combined a browser and a phone and a music player together. We never would've said that as users. Right. You know, it would be great if, if all these things, I'm sure there are some people out there that would, but most of us are not that.

You know, savvy or futuristic looking. Um, so, but if you a, if you interrogate them in a, in a good way to understand, you know, not only what's pushing them and pulling 'em towards progress, but what's keeping them from doing it, then you can make something that they really want and then they'll be like, wow, how did you, I'd never told you that.

How did you know, you know, that I wanted that. Um, and it's because, you know, we did a good job of really the word is interrogating and, and that's a bad word for most people, but interrogating is not, you know, shining a light on someone's head and saying, where were you on Tuesday? And it's, it's [00:33:00] it helping them to remember things that they didn't really realize they knew.

Right. You know, so a good investigator will say, you know, so tell us, you know, you witnessed a crime. Tell us what you, what you witnessed. And they'll say something and they said,

okay.

You know, like, and I can't really remember his face or whatever, you know, and they say, okay, so was it, was it sunny out or windy out?

You know, was it

a Tuesday? Who

were you with? And they know that when you, when you get, let them associate with other memories that will trigger, uh, uh, that thing and they'll actually remember something that they didn't even know they, they've remembered.

That's

what a really good marketer does in my opinion, is they're, they're able to pull things out of a, a customer that they didn't even know that they were thinking.

And

when you're good at that, then again, you go to market, it is a lot easier. 'cause they'll be like, they'll, they'll wait in line, you know, for days on end to buy your product from you.

[00:34:00]

Natalie Nathanson: ~And I think that's, you know, spot on for what we've experienced as well as for, uh, kinda where we're headed in the, in the world ahead.~

One of the things I'm thinking about, kinda going beyond the go to market is this concept of curiosity. And then knowing what to do with it. Right. as you just discussed, how that applies to kind of marketing and go to market.

Um, but I think as we're looking at how do you kinda innovate, how do you bring customers to places where they don't know they have,

uh, kind of a need or can't imagine, like what the solution looks like.

Um, I'm curious to hear from you, like, what, what do you think are the most, uh, [00:35:00] kinda important, uh, skill sets for CEO founder? Uh, for the future?

Bill Flynn: Uh, skill sets, that's

a good one.

Um, it's more of a, to me it's more of a mindset than a skillset because, um, so, so PE people follow leaders. Right. And, and you know, I, I go to these, I haven't gone in a while, but I used to all these conferences and, you know, and you get people up there and they say, this is what a leader is.

A leader is humble and charismatic and you know, and curious and whatever. And, you know, and I would say, you know, Steve Jobs wasn't really that humble. Um, Warren Buffett isn't that charismatic. Um, you know, and I could go through all these different leaders and, and they're all really different, but there's, there's some sort of gravity that they create that says to a certain person, I want to follow that person.

Right? So, um, what I've come to believe is that you only need two things as a leader. [00:36:00] Uh, you can have all the other stuff and it'll be great and it'll add, add, you know, it'll be additive, you know. Um, but there's only two things that all great leaders have in common. One is they have a compelling vision.

Because people wanna know where are we going? Right? I'm, I'm following you. Tell me where we're going. Right? Describe Oz for me, or describe whatever it is that you think is gonna end. You know, we want to end up, you need to be able to describe that in such vivid detail that I can see it as if it already happened.

Then what you are doing is you're obviously attracting them to you, but you're also giving them a lot of great information that will allow them to do their job better. And they say, well, if that's where we're going, then here's how I can contribute. And I'm now pushing you and pushing the company by saying, okay, this is what I think we should do.

If, if that's true, as opposed to you having to pull everybody. Right. And, and the larger the company gets, the harder it is to pull, gets heavier and heavier. So that's one thing. You have to have some sort of compelling vision. Um, and it's not a sentence, right? It's a, it's, it's a picture that you're painting.

I just wanna be very clear. Uh, and then the other is courage. The [00:37:00] only other thing that I've seen every other leader have is courage. And, you know, the, the courage to you, you're doing something that's unusual, um, that's difficult. You know, you're having to sort of take a leap of faith. You have to have the courage to give away your company, the people that haven't run it.

You have to have the courage to say, I don't know, I'm sorry. And, and, and can you help me? So you can create a psychologically safe environment. There's so many things that you need to be courageous about that. I think those are the only two things that all leaders have in common. Now, if you want to be an even better leader, I'm a big fan of, you need to be humble.

Um, you need to be hungry and not hungry just to grow, but hungry, like just hungry, getting better and, and, and improving yourself, improving the company. Um, you have to be a learner. Um, uh, and you have to be comfortable challenging the status quo. You have to constantly say, you know, but I know that's the way we did it, but is that still the best way to do it?

You know, uh, are we, are we actually, um,

doing

everything we possibly can? Is this the optimal? And I think if you have those characteristics, and that's, that's sort of how I [00:38:00] pick my clients. If you don't have those four characteristics, I can't help you. If you have three out of the four characteristics, I still can't help you because I'm gonna come in and ask a bunch of questions.

And if you are not humble, you're gonna feel challenged by me. You're gonna think I'm saying you're not a good leader. But I'm not, I'm not doing that. I'm just.

you know,

I'm saying, I come in with a beginner's mindset and say, well, why do you do it that way? And how do you know, and, you know, defend that position.

You can't just say, I wanna do this, you have to defend it. Right. Give us your reasons for doing that. Um, and a lot of people don't like that. Uh, so, you know, uh, so, so that's, I think if you wanna be a, a leader these days, you have to have, you certainly have to have the first two things, and it'll make it a lot easier for you if you have the other four as well, but most people don't.

I've found, I'd say 90% of the leaders I talk to don't have those four characteristics. Maybe not even have all six, which is why I say, you know, I, I have a very small set group of people that I can work with.[00:39:00]

Natalie Nathanson: I think that's also one of the reasons I've always enjoyed our discussion so much, is that, uh, kind of profile really resonates, uh, with me and, and, you know, my, my own values.

Um, I'm curious though, to hear what of those, uh, you know, characteristics are, uh, innate. Like either you have it or you don't, and what can be learned, right? So if someone comes to you and says. Like, I, I recognize my leadership skills to date are not gonna take me where, you know, where we need to go in the years ahead.

Like what of those areas can be changed? And, uh, can I, do you work with, with clients in that way and how?

Bill Flynn: So, uh, I think you know this, I'm a bit of a neuroscience geek, uh, and, uh, so to me there, there are three things that, that you have, uh, that are available to you as a person and as a, as a, as a contributor to a company, you have abilities, you have skills, and you have knowledge,

skills, and knowledge

can be learned.

Right. And, and most skills and knowledge can be learned. You know, you, you, if you're three foot six, you [00:40:00] can't dunk a basketball. Right? But, you know, if you're, if you have the general, um, uh, uh, format, then you can probably, you can learn just about anything.

Um.

abilities are really hard to learn. Your parents gave them to you, either through their DNA and through their nurturing and your friends and, and et cetera.

So you, you come mostly formed when you, when you are now in the workforce, can you change those things? Absolutely. You can change them, but they're really hard and they probably take a long time. Right? Because you're now, um, having to go against something that is, is, feels to you like it's just natural. Um, so for instance, you know, I, I, when I talk to leaders, I say, your job.

Isn't to make a well-rounded person. There's no such thing. Um, we are all spiky and idiosyncratic, but your job is to create a well-rounded team out of these spiky people. [00:41:00] But first you have to understand, you know, what that team looks like. And, and, um, I'm now mess, I'm now with this new metaphor, which I can't remember if I told you last time we spoke, is, um, most of the time when we're, when we're take, we take over a team, we're sort of given this, this opportunity to say, Hey, here you go, make a great team.

And it's, to me, it's the equivalent of, of saying, Hey, I want you to create a high performance vehicle and the garage is over there. Um, good luck, right? All the parts are in there. And then you go into the garage and you're like, you know, you like, you grab, you know, grab an engine and you grab a pipe and you know, you're like fitting them together.

You're taping things up and, you know, pushing things together, you know, to see if they'll fit and whatever. Um. But we never, and then, and then you're like, okay, that's the best I can do. But we never like step back and say, okay, am I building a Formula One car? Am I building a a car for Dakar, which is a desert race?

Am I, am I building, you know, a monster truck or what, you know, what, what, what is it that I'm actually creating First? We don't even step [00:42:00] back and say, what would that look like? First, forget the people, forget the parts. Like, how would that look, right? What, what would I need to do that? Then you go in the garage and you say, okay, let me, now I know what to look for and I'll know what's missing, and I'll know, oh, I can, that's not quite there, but I think I can tweak that a little bit and, you know, I can put a little, um, heat on that and flange it out and it'll fit onto this thing.

Um, but we never do that. And then we're, so we're always similar to your go to market. We're always solving the problem from the middle, and we don't even know what great looks like first. Um, so if you don't have, if you don't have that ability to understand how your team is, then you're not gonna be the best possible leader, right?

So you have to sort of have this, i, i, I call it the architect mindset, right? Which is, you have to understand that you're, you're architecting things and you used to be a hero, which was great. And actually what's interesting is all the things that you did that got you to where you are, are now [00:43:00] almost the exact opposite of what you have to do going forward, right?

Because you can't be decision maker, you can't be solving all the problems, you can't have all the answers. You have to create the environment. So, and, and feel good about the fact that you didn't, which is really weird for people 'cause they're like, it doesn't feel right. So, um, if you don't have that as your mindset, then you're always gonna struggle as a leader, in my opinion.

Or you're gonna do everything yourself and just have a horrible life.

Natalie Nathanson: Um, I believe, and correct me if I'm wrong, that this is kind of in the, the, the vein of what you have, uh, kind of developed of a hero to architect. Is that right?

Bill Flynn: Yeah. Yeah. I just, I just wrote a book.

um, I just wrote a bunch of books, but the first one that will come out hopefully will be, uh, it's called A Hero to Architect. Yes. Where you, you have to, you have to transfer from being a hero to being an architect.

Natalie Nathanson: Which is a, I think such a, an interesting, uh, framework and I think speaks to that shift that a lot of leaders need to make. Um, I know, [00:44:00] um, a concept that you taught me and then recommended a, a wonderful book around it.

I think leaders make the world or Make the Future. sorry, um, had, um, kind of banny, BANI, uh, can you kind of explain that for, for our listeners and you know, how that ties in with this concept?

Bill Flynn: so some people might know vuca, uh, which is volatile in certain, I can't remember the other two, um, that came outta the war college, um, in,

in the

eighties, I think seventies or eighties, which basically said, you know, here's the world that you're in as leaders, you know, in a, in a, in a military environment.

Um, and that then was applied to business, right? And

that's

generally true, but what wasn't, what has been added in the BANNEY world, which is brittle, anxious, non-linear and incomprehensible, is this emotional part of things, right? This anxious, right? Luca didn't have any anxiety and it was all sort of very tactical stuff.

Um, and you have to understand that you're, you're in this, in this [00:45:00] world where. Stuff is happening and you can't, one, one, you can't even fathom that it's happening and then it's happening so fast, right? And you can't even like, catch your breath. Um, I, um, fortunately, or, or unfortunately I am, I am going out with a woman who works at Silicon Valley Bank and we were in Mexico, uh, or just on our way to Mexico when everything happened there a couple years ago when $42 billion was removed from the bank in like 24 hours.

Uh, and the leaders were doing everything that they thought was the right thing to do, right? So they were actually solving perfectly the, the problem, but for the wrong situation,

right?

So, so, and then the world basically told them, you know, this doesn't work. And, um, unfortunately, you know, they, they, you know, basically had to go into receivership and it's just a lot of stuff they had to do.

Um, I think that is one of the most. Um, dramatic examples of this world that we're in. [00:46:00] Um, but you know, like the Southwest, um, problem they had with their, um, reservation systems and, uh, you know, that, that all of a sudden just happened and they were surprised by it. Um, there are so many other examples that we have that shows us, not that we're entering this world, but we've been in this world for a while and we just haven't noticed.

Right. And no one's really paying attention to it. Um, and we're not prepared for it. Right? Uh,

you, this word resilience right, is a thing. Um, you, you, you know, I, I'm, I'm now moving my clients from doing a lot of planning, you know, to doing some planning, but I'm saying, Hey, but at any point we may have to shift the plan, right?

If something crazy happens in your world. So you have to create the environment. So one, you can detect the shift as early as possible. And that means that anyone in your organization needs to be aware. 'cause you might not see it, but someone on the front line might see it. Um, so you have to create that environment.

So you're [00:47:00] sort of doing this detection thing, and then you have to create this environment where you can shift quickly, right? Is that you can, you have the, the things in place to move. Um, when the world moves, when the cheese moves, so to speak, very quickly, then you are already set up to do that. But we don't do that.

We have these, you know, sort of, um, hierarchical models where the information gets flowed up to the top. We make a decision, then we push the thing back down. By the time you did that, something else has changed, right? And you're already behind, right? So you have to create this environment where, again, you are not making all decisions, but you're creating an environment where those things can happen really quickly.

Yes, with your guidance, but you don't have to be there. You, you know, in some cases you might be on vacation. Okay. And see what happens. Um, and I know that, um, Reed Hastings did this a number of years ago. He didn't do it purposely. Um, but now when you read about it, it, you know, it almost, it makes it sound like he, like, did this experiment.

Um, but he's a big fan of taking time off. So he, he would take six weeks off at a time and unplug from the company and [00:48:00] see what, and then he wanted to see, also see how they worked. Right. How did they do without him there? Um, and mostly they did pretty well. There were some parts of the company that didn't do as well.

Usually the things that he's good at. Right. Which is usually what happens. Right? The stuff that we're really great at is where a company is weak. Um, but you wanna be able to be in a situation where is, if this happens, you don't have to be the person making the decision all the time, because it may happen many, many times and you can't be in all these places at once.

So that's the architect, right? That's where you're creating the environment. You're, you know, you're, you're really saying, okay. Why are we building this building? You know, what are, what are the tenants trying to get out of it? You know, what is the person who owned wants to get out of it? How tall is it gonna be?

Where is it gonna be in the city? Should it be north facing, south facing? You know, there's all these things you have to think about as an architect. Then you build the building, right? You know, back to your go to market. What happens with go to market is they just start building the kitchen, and they hadn't thought about the rest of the house, [00:49:00] uh, yet, but they're like, you know, well, the kitchen is the most important thing, right?

It's where stuff happens, et cetera. And then you have a really nice kitchen, and then, you know, what happens is the ki the house falls over and so does the kitchen, but it's a really good looking kitchen,

Natalie Nathanson: But

it didn't have the right foundations.

Bill Flynn: Exactly

right. Yeah. So that's sort of, that's sort of what this banty, this, this banty world that we are in, uh, means, is that you have to understand that things are brittle, right?

Things will, things that you think are strong. Like the SVB folks, they thought they had a really strong business and then all of a sudden they didn't. Um, and it was incomprehensible to them. I mean, they, while it was happening, so I was witnessing it while it was happening because c uh, Kristen would be on the call, like, and I'm sitting there, you know, on the couch listening to her, to her call.

I'm like, wow. They're like, they're like, they're like, well, I don't know what happened. Why did this happen? They were like, they were just, just as amazed as everyone else and they worked there.

Natalie Nathanson: Yeah. well unfortunately I think we are gonna see more of that unless organizations really kinda evolve how they're looking, uh, looking at these, uh, [00:50:00] areas.

Um, I, I know Bill, we don't have that much time left. Um, I wanted to ask, um, you know, if you have any advice for, for CEOs, whether it's, you know, things that we haven't yet covered or in a summary of some of what we've talked about, CEOs who wanna better equip themselves and their organizations for the decade ahead.

Any kind of top line recommendations there.

Bill Flynn: Yeah,

And a lot of this is sort of motherhood apple pie. So, um, the, to me, the team, so I teach three things, team operating system and has cash as your fin financial metric, right? Is that's the way you wanna do it. To me, team is always the most important thing. Um, you know, you can have a decent, you know, I mean, EOS is pretty good.

It's not great. You know, scaling up has some stuff, but, but not having one is much worse than even having one. That's okay. Right? So, so, so, but, but if you don't have, if you haven't surrounded yourself with a great team, then you are always at a deficit, uh, because, you know. One of the things that I did, which I think, think still holds true.

When I was, when I was [00:51:00] doing the Vistage speaking, I would always start off, I did the same, you know, I did like, I did 40, 50 times and I did the same thing, right? And I would go in and I'd say, what is the greatest barrier? What's the biggest barrier to your business right now, to your growth of your business?

And then they would all write it down on a sticky, and then I would put it up on the wall. And,

and I

would say most of the time, 80% of the, of the answers were operational, right? We're not doing things right, we're not doing them on time, we're not doing them well, whatever. Um, and I said, so what are you executing on?

And you know, I trying to get them to, you're executing on a strategy, right? And, and so I said, so if, what would happen if I walked into your. Monday morning meeting at 10 o'clock and, and everyone around the room say, can you write down in your own words what our company, our current company strategy is?

And we all read them out loud and I said, what would happen? And they all do that, what you did, they smile, they laugh, right? And say, oh, they'd be all over the place. And I said, well, yes. So, so maybe your execution frustrations are that they're executing really well on what they think the strategy is, [00:52:00] right?

So you gotta get 'em on on the same page, but they have to help you get on the page, right? So you have to have people

who.

can round out your thinking that think that, believe what you believe, but think differently than you do, because that's what elevates the conversation, right? You want dissonance, you want disagreement.

You want people to say, yeah, but what about this? And what about that? And you know, the customer and the supplier. And you know, we have to sort of think about the whole set of stakeholders in the ecosystem. And that's why you have all these wonderful people. If you don't have them, then you have to do it.

And

it's just hard. That's what I said. You could probably do it, but eventually you'll stop. Right. I I, I have a client that I just lost, which I've been trying to get him to, to get out of the way and he knows to get outta the way, but we just, after five years, you know, we both basically just gave up.

'cause he's in the way and he's, I see him on Instagram and whatever, and he is still in the way

Natalie Nathanson: Which is back to that bottleneck example that you

Bill Flynn: right? And, and the

Natalie Nathanson: like lead, uh, organizations only grow as [00:53:00] much as the, the leader is ready to, to grow them.

Bill Flynn: Right.

and even, even though he's lost 13, I, I worked in five years. There were 13 different people on the executive team since I started with them

and only seven

or eight people on the executive team. So he's gone through. And he's still not getting it right. And that's what I think happens to a lot of leaders, unfortunately, right?

Is, is that they don't realize that they have to let go, right? They have to have that courage to let go, hire great people who are gonna challenge you, you know, make you feel like you don't know. It's, it's better to say, I don't know the answer, right? And let's, but let's figure out the answer, right? I know the destination, I know what it wants to, I want it to look like.

But, you know, not knowing how to get there is a really uncomfortable place for most leaders because again, they've been rewarded since they were seven on knowing how to do something. Uh, so I think that's, that's gonna be the challenge for, for leaders.

Natalie Nathanson: Well put, bill, I think that's a great place to wrap. Uh, if our listeners want to reach you, what's the best way to get in touch?

Bill Flynn: Uh, catalyst Growth Advisors is my website. [00:54:00] Um, so if you wanna reach my phone number, my calendar there, my book is on there for free. Hopefully other books will be on there at some point as well. Um, so that's the best place, www.catalystgrowthadvisors.com,

Natalie Nathanson: Perfect. Perfect. Well, thank you so much. This was a fantastic conversation

Bill Flynn: as

always.

Natalie Nathanson: thank you so much for all those insights and thank you too to everyone that's listening.

I know I loved hearing about so much of what Bill shared with kind of the new CEO mindsets and notice I said mindsets and not skills, bill, uh, you know, the Hero to Architect framework and you know, some of the, the dialogue around, you know, how we all need to evolve our own, uh, kind of thinking and, and ways of working to help us, uh, really, you know, set ourselves up for success, uh, for, for the future.

So thank you so much Bill, and this has been another amazing conversation on Shift and Thrive. I'll see you all next time.

[00:55:00]