Artwork for podcast The Breakout CEO
53 - Diagnose Before You Scale: The CEO Discipline Most Skip
Episode 53 • Bonus Episode • 14th April 2026 • The Breakout CEO • Jeff Holman, General Counsel for Scaling CEOs and Founders
00:00:00 00:29:13

Share Episode

Shownotes

Many CEOs try to fix growth problems by adding more resources—more marketing, more hires, more tools. But according to advisor Jon Bassford, scaling problems rarely come from a lack of effort or investment. They come from failing to diagnose what’s actually broken inside the organization.

In this episode, Bassford explains why CEOs must diagnose operational and cultural breakdowns before trying to scale execution. He shares the signals he looks for when organizations stall and a practical process CEOs can use to uncover what’s really slowing growth.

00:01 — Host Welcome And Guest Introduction

01:05 — Bassford Background And Career Path

02:05 — Advisory Work With Scaling CEOs

03:10 — Leadership Mindset Culture Operations Framework

04:30 — Founder Triggers For Operational Help

06:10 — Diagnosing Alignment And Operational Gaps

08:20 — Psychological Safety And Team Voice

10:35 — Leadership Letting Go Of Control

12:10 — Process Mapping As Organizational Tool

15:05 — Operational Alignment And Decision Speed

17:10 — Freedom And Profit Impact For CEOs

19:50 — Fear Habits And Leadership Decision Paralysis

23:10 — Practical Process Mapping Framework

26:10 — Leadership As Orchestra Conductor

27:20 — Closing And Contact Information‍

Jon Bassford

Founder & CEO — Lateral Solutions

Website: https://think-lateral.com

Personal Website: https://jonbassford.com

LinkedIn: https://www.linkedin.com/in/jonbassford/

Think you'd be a great guest on the show?

Apply https://go.intellectualstrategies.com/

Get in Touch with Jeff Holman ⤵️

Website: https://www.intellectualstrategies.com/

Instagram: https://www.instagram.com/holmantech/

Facebook: https://www.facebook.com/jeff.holman.9678

LinkedIn: https://www.linkedin.com/in/holman/

Transcripts

Speaker:

The diagnosis piece is what a lot of founders and CEOs miss.

2

00:00:05,003 --> 00:00:08,277

They take what they already do and they throw more at it.

3

00:00:08,277 --> 00:00:11,276

The over analysis is a symptom of fear.

4

00:00:11,276 --> 00:00:13,408

Welcome back to the breakout CEO podcast.

5

00:00:13,408 --> 00:00:16,872

I'm your host Jeff Holman and I'm here today with John Bass for John.

6

00:00:16,872 --> 00:00:18,413

It's great to have you on the show.

7

00:00:19,313 --> 00:00:20,235

Yeah, of course.

8

00:00:20,235 --> 00:00:27,662

I was, I was talking to you just briefly before the show and we made the connection that

we're both JD MBAs.

9

00:00:27,723 --> 00:00:31,476

That's, that's a fun, fun little package to have her.

10

00:00:31,628 --> 00:00:34,130

Yeah, yeah, it's a, I'm a little different.

11

00:00:34,130 --> 00:00:40,022

I've never practiced and fell into a uh business operations side of the house and then

ended up getting my MBA.

12

00:00:40,022 --> 00:00:43,682

But there's no doubt I still use my law degree on a daily basis.

13

00:00:43,682 --> 00:00:49,107

Yeah, no, that's, mean, some attorneys would say, well, you're one of the lucky ones who

escaped the systems, right?

14

00:00:49,107 --> 00:00:52,029

So good for you though.

15

00:00:52,029 --> 00:00:56,753

But I imagine we both got our MBAs to learn more about how to speak business language.

16

00:00:56,753 --> 00:01:04,819

I always tell people I got my MBA, you know, I wanted to learn about all the other stuff

people were doing besides just getting patents at the time that that's what I was doing.

17

00:01:04,819 --> 00:01:13,238

And uh really came away with the vocabulary, which sounds simple, but if you don't know

the vocabulary of business, you're just, you're not even.

18

00:01:13,238 --> 00:01:15,827

It's, it's hard to have table stakes in the game.

19

00:01:15,982 --> 00:01:23,442

Yeah, for me, you know, I fell into operations side of, of association management

originally, then started working with startups and small businesses as well.

20

00:01:23,442 --> 00:01:28,522

And, you know, I didn't have any business education, high school, college, whatever.

21

00:01:28,642 --> 00:01:39,042

just kind of learned as I went along and, you know, I kind of got the MBA just to add the,

the letters after my name to, to add some more clout to, you know, the, the years of, of

22

00:01:39,042 --> 00:01:41,802

hard work I'd built in, in learning.

23

00:01:42,019 --> 00:01:44,713

the business side of the internal operations side of business.

24

00:01:44,713 --> 00:01:48,420

So I was overseeing accounting, finance, HR, legal, et cetera.

25

00:01:48,420 --> 00:01:53,128

And one of the education to back up what I'd been doing.

26

00:01:53,400 --> 00:01:53,970

that's awesome.

27

00:01:53,970 --> 00:01:54,870

That's awesome.

28

00:01:54,870 --> 00:01:58,551

mean, that's the route that a lot of our audience has taken, right?

29

00:01:58,551 --> 00:02:06,994

They haven't necessarily all got a lot of letters behind their name, but they've got a lot

of, uh we'll call it dirt under their fingernails and such.

30

00:02:06,994 --> 00:02:09,234

They've been down those paths.

31

00:02:09,273 --> 00:02:10,975

So no, it's a good place to be.

32

00:02:11,275 --> 00:02:22,178

Well, today's part of our advisory insights episodes for the month, and we're talking

about how CEOs of scaling companies evaluate and make big decisions in the company.

33

00:02:22,178 --> 00:02:31,385

You know, there's a lot of chances for CEOs to make decisions all day long, every day, but

we want to focus on what are those big pivotal decisions that they make and really what

34

00:02:31,385 --> 00:02:40,231

are the frameworks that they can draw on and, you know, maybe come to people like you and

say, hey, John, how do I approach this decision?

35

00:02:40,231 --> 00:02:42,402

This is a more meaningful decision in the business.

36

00:02:42,402 --> 00:02:47,596

Maybe it's, you know, maybe it's life changing or whatever, but it's a bigger decision.

37

00:02:48,076 --> 00:02:50,712

Man, I just want to be more careful about how I do this.

38

00:02:50,712 --> 00:02:52,613

than every other decision I do.

39

00:02:52,613 --> 00:02:54,744

So is that something you work with CEOs on?

40

00:02:54,744 --> 00:03:04,059

Sure, I work on the operational side of the house, but my business and my work has really

come to also include leadership mindset and culture.

41

00:03:04,059 --> 00:03:10,233

Throughout over the years, that's what I've really learned that to create sustainable

growth, you have to cover all three of those areas.

42

00:03:10,233 --> 00:03:18,497

The mindset of leadership, how they're thinking, how they're operating, the culture,

meaning how you bring the team along with you, the operations side of the house, which is

43

00:03:18,497 --> 00:03:19,928

how we function day day basis.

44

00:03:19,928 --> 00:03:23,222

And that really became the basis for uh

45

00:03:23,222 --> 00:03:30,626

my book, curious leader, where I talk about curious leaders change how we think, how we

work and how we connect.

46

00:03:30,626 --> 00:03:31,667

Yeah, I love that.

47

00:03:31,667 --> 00:03:34,922

I want to hear more about the curious leader and the curious leadership framework.

48

00:03:34,922 --> 00:03:36,394

think that you've got in the book.

49

00:03:36,394 --> 00:03:41,021

So, um, well, what's a typical engagement look like for you?

50

00:03:41,021 --> 00:03:42,403

Who do you work with?

51

00:03:42,403 --> 00:03:45,848

What level of, uh, contact do you have with the CEO?

52

00:03:45,848 --> 00:03:47,662

What types of companies are you working with?

53

00:03:47,662 --> 00:03:51,742

Yeah, usually the CEO or founder is my main contact.

54

00:03:51,742 --> 00:03:52,442

I'm usually working with that.

55

00:03:52,442 --> 00:03:56,142

So I'm working with small businesses, startups, nonprofits, associations.

56

00:03:56,142 --> 00:04:06,582

So it's, I'd say that sweet spot is, you know, kind of five to $50 million range, whether

that's revenue or fundraising coming in for a startup.

57

00:04:06,762 --> 00:04:10,362

I'd say the startup is a little different.

58

00:04:10,362 --> 00:04:13,462

I tend to work with them in the beginning phases.

59

00:04:13,762 --> 00:04:22,839

When they don't necessarily have the process procedures set up the way they should, they

don't really have someone, experienced person at least, overseeing the operational side of

60

00:04:22,839 --> 00:04:23,650

the house.

61

00:04:23,650 --> 00:04:29,534

Whereas the small business and association side is more about helping them break through

stagnation.

62

00:04:29,534 --> 00:04:35,318

oh So I'm going to meet those different industries at different places.

63

00:04:35,384 --> 00:04:36,274

Well, that makes sense.

64

00:04:36,274 --> 00:04:47,221

And every startup at those early stages is so, so uniquely tied to the, to the founder and

their vision and their personality that, that you kind of have to approach every one of

65

00:04:47,221 --> 00:04:48,361

those as its own engagement.

66

00:04:48,361 --> 00:04:58,107

um When you, when someone reaches out to you and says, Hey, I got this issue I'm dealing

with, or I'm looking to improve my business in this way.

67

00:04:58,107 --> 00:05:04,734

What, what usually triggers them to like, what's going on in the business where they just

say, man, I've been looking at these.

68

00:05:04,734 --> 00:05:11,566

these metrics or I've been seeing these signals in the business, I got to figure out how

to maybe draw on some additional expertise.

69

00:05:11,566 --> 00:05:12,046

Yeah.

70

00:05:12,046 --> 00:05:13,786

So usually a couple of scenarios here.

71

00:05:13,786 --> 00:05:17,586

One is, you know, thinking of like, know something is not working.

72

00:05:17,586 --> 00:05:18,966

I just don't know what it is.

73

00:05:18,966 --> 00:05:19,186

Right.

74

00:05:19,186 --> 00:05:21,586

Or I know what I know and I don't know.

75

00:05:21,586 --> 00:05:22,066

don't know.

76

00:05:22,066 --> 00:05:29,826

Like, you know, one of my conversations in last couple of weeks was, was with a, with a

lawyer who founded a law firm that was, you know, at two locations about to branch into a

77

00:05:29,826 --> 00:05:30,026

third.

78

00:05:30,026 --> 00:05:31,766

And he kind of like, he hit his wall.

79

00:05:31,766 --> 00:05:36,286

He's like, he's like, this is as far as I can take this operationally without some extra

help.

80

00:05:36,286 --> 00:05:39,662

And then the other thing is, piece of it is.

81

00:05:39,662 --> 00:05:43,302

You know, we built a good foundation or we built a good business.

82

00:05:43,302 --> 00:05:46,742

We are growing, but we want to go from five to 50 million.

83

00:05:46,742 --> 00:05:48,122

We want to go from 50 to 100 million.

84

00:05:48,122 --> 00:05:51,142

We want to make sure that we have the right foundation.

85

00:05:51,142 --> 00:05:57,482

And so that's the other place where they come in and say, Hey, look, you know, there

aren't any problems necessarily, but we know we could do a little bit better.

86

00:05:57,482 --> 00:05:59,362

We know we could create a better foundation.

87

00:05:59,362 --> 00:06:00,722

And how do we do that?

88

00:06:00,870 --> 00:06:10,128

Yeah, I think a lot of businesses I mean they need that right because they they've grown

from just scrappiness and kind of patching things together and Pivoting from one thing to

89

00:06:10,128 --> 00:06:15,642

the next to the next with some maybe some tech debt and just some culture debt along the

way, right?

90

00:06:15,642 --> 00:06:27,162

How do people how do people come to the point where they say I think this is foundational

I think I need to step back and and rework the the you know tools or the processes or the

91

00:06:27,162 --> 00:06:30,274

team that I've got and and put a

92

00:06:30,274 --> 00:06:33,634

the right things in place now that I know where I'm headed.

93

00:06:33,634 --> 00:06:35,954

Like how do they get to that decision point?

94

00:06:36,014 --> 00:06:37,294

Yeah, so I think a couple of things.

95

00:06:37,294 --> 00:06:42,314

One is when the CEO founder is still finding himself constantly working in the business.

96

00:06:42,434 --> 00:06:45,734

Everything comes through then, they touch everything, they want to see everything.

97

00:06:45,734 --> 00:06:47,374

They know that that's not sustainable.

98

00:06:47,374 --> 00:06:49,034

mean, that's one of the first things.

99

00:06:49,254 --> 00:06:53,514

seeing that the team and decision making alignment just isn't there.

100

00:06:53,914 --> 00:06:56,054

There's constant slowness and stagnation.

101

00:06:56,054 --> 00:06:57,574

Again, you're getting the work done.

102

00:06:58,254 --> 00:07:04,054

Things aren't falling apart per se, but they feel the cog in the wheel.

103

00:07:04,054 --> 00:07:05,070

And I'd say

104

00:07:05,070 --> 00:07:07,330

Nine times out of 10, it's a gut feeling.

105

00:07:07,330 --> 00:07:08,730

They don't know really what's going on.

106

00:07:08,730 --> 00:07:10,070

They don't use the word foundation.

107

00:07:10,070 --> 00:07:11,930

They don't use the words alignment.

108

00:07:12,590 --> 00:07:15,770

It's something they feel, it's just off.

109

00:07:16,450 --> 00:07:20,870

what we do is, our framework is called clarity to execution.

110

00:07:20,870 --> 00:07:27,550

We're helping them go in, diagnose what's wrong, create a plan to fix those holes, and

then execute on that.

111

00:07:27,550 --> 00:07:33,170

And the diagnosis piece is what a lot of founders and CEOs miss.

112

00:07:33,170 --> 00:07:35,046

They take what they already do,

113

00:07:35,231 --> 00:07:36,665

and they throw more at it, right?

114

00:07:36,665 --> 00:07:42,956

More ad spend, more marketing, more people without ever taking the time to diagnose where

they are at the moment.

115

00:07:42,956 --> 00:07:43,376

Yeah.

116

00:07:43,376 --> 00:07:47,727

So, I mean, it seems like they're, I mean, that's classical strengths finders type stuff,

right?

117

00:07:47,727 --> 00:07:52,009

Build on your strengths, just keep doing more of the same, but maybe that's not always the

solution.

118

00:07:52,009 --> 00:07:56,370

You know, as you're explaining that, I'm thinking about my own evolution in my business.

119

00:07:56,370 --> 00:08:01,471

And I'm saying to myself, there are some times that maybe you're describing.

120

00:08:01,471 --> 00:08:04,872

So I'm just going to throw them out there, see if these are the things that people come up

with.

121

00:08:04,872 --> 00:08:09,473

You know, and I've said to myself, gosh, I feel like I'm the only one coming up with

solutions.

122

00:08:09,473 --> 00:08:12,600

There's a lot of work to be done and I've got good people.

123

00:08:12,600 --> 00:08:22,353

But when we need to go to the next level or we encounter a new situation, everyone stops

and says, Hey Jeff, what do you want to do?

124

00:08:22,353 --> 00:08:28,095

And like to me, I, I don't mind coming up with solutions because I like solving puzzles.

125

00:08:28,095 --> 00:08:31,626

That's probably the, the engineer and the attorney inside of me.

126

00:08:31,626 --> 00:08:31,886

Right.

127

00:08:31,886 --> 00:08:36,357

But, it's not necessarily as scalable if I'm the guy doing all that.

128

00:08:36,357 --> 00:08:37,978

Is that kind of what you're describing?

129

00:08:37,978 --> 00:08:38,348

Yeah.

130

00:08:38,348 --> 00:08:39,178

That's a big part of it.

131

00:08:39,178 --> 00:08:40,359

That's the culture piece.

132

00:08:40,359 --> 00:08:45,411

So so again that's another piece that people miss is uh you know right.

133

00:08:45,411 --> 00:08:51,443

The Curious Leader book when I talk about how to how we just how we connect that's that's

the culture piece how we bring our team along with us.

134

00:08:51,443 --> 00:08:57,006

And if we're going to continue to grow scale and innovate the founder CEO cannot be the

only one.

135

00:08:57,006 --> 00:09:00,107

uh There's actually a study by Google.

136

00:09:00,107 --> 00:09:05,569

Google is trying to figure out what made teams within Google successful.

137

00:09:05,569 --> 00:09:08,290

So they did thousands of interviews questionnaires etc.

138

00:09:08,462 --> 00:09:15,705

It was called Project Aristotle, uh stolen from Aristotle's view of that the whole is

better than the parts.

139

00:09:16,105 --> 00:09:19,327

And what they came back with was psychological safety.

140

00:09:19,847 --> 00:09:27,670

What that means is the leaders creating an environment that encourages people to speak up,

speak out, bring ideas, point out problems.

141

00:09:27,891 --> 00:09:36,174

And the thought that always comes to my head when talking about this is we've probably all

experienced some version of this story where the CEO founder

142

00:09:36,302 --> 00:09:40,122

you know, through some work that they're doing, discover some problem.

143

00:09:40,122 --> 00:09:41,722

And they're so excited about it.

144

00:09:41,722 --> 00:09:48,882

And they come to the team, you know, describe the problem, go to the person who tactfully

handles that issue every single day.

145

00:09:48,882 --> 00:09:51,002

And the person's like, yeah, I know.

146

00:09:51,462 --> 00:09:53,062

I've known for six months.

147

00:09:53,482 --> 00:09:56,002

And what always happens, the leader gets mad at the employee.

148

00:09:56,002 --> 00:09:57,862

Why didn't you speak up?

149

00:09:58,262 --> 00:10:02,422

But what I always turn it back around, I'm like, why didn't you create an environment

where they did speak up?

150

00:10:02,422 --> 00:10:05,286

Why aren't you creating those mechanisms in

151

00:10:05,334 --> 00:10:11,370

and how this employee is managed, whether it's the CEO or someone between the two, that's

tapping into them.

152

00:10:11,370 --> 00:10:12,561

Hey, what are you seeing?

153

00:10:12,561 --> 00:10:13,391

What's wrong?

154

00:10:13,391 --> 00:10:14,923

How can we do things differently?

155

00:10:14,923 --> 00:10:22,600

Those are the conversations that are missing in organizations to where all ideas have to

flow from the top.

156

00:10:22,604 --> 00:10:24,455

Yeah, I've brought this up on other episodes.

157

00:10:24,455 --> 00:10:29,037

I don't mean to keep breaking it up, but it's maybe so basic and so fundamental.

158

00:10:29,037 --> 00:10:38,341

Patrick Lindsay on these five dysfunctions of a team, When you talk about psychological

safety, that's how you get trust and how you get the buy-in, what is it, the weigh-in, the

159

00:10:38,341 --> 00:10:44,683

buy-in layers of uh a functional team as opposed to the absence of those in a

dysfunctional team.

160

00:10:45,764 --> 00:10:48,565

yeah, the psychological safety, that's a great topic.

161

00:10:48,885 --> 00:10:50,966

And one that...

162

00:10:51,542 --> 00:10:58,646

I for lot of leaders feels like it's just, know, like I want it and I want to accomplish

it, but do I have time?

163

00:10:58,646 --> 00:11:02,848

I'm running fast, maybe hustling or grinding a few of those words.

164

00:11:02,848 --> 00:11:14,454

But you know, how does a busy leader em incorporate more psychological safety into what

they're doing on top of the other things that they're trying to accomplish?

165

00:11:14,734 --> 00:11:20,174

So this usually begins my work with working the CEO of focusing on the leadership mindset,

first of all.

166

00:11:20,194 --> 00:11:23,554

one of the biggest things I have to work with him on and letting go, right?

167

00:11:23,554 --> 00:11:24,594

Letting go of control.

168

00:11:24,594 --> 00:11:34,534

mean, the, was working with a young, ridiculously smart startup founder working 20 hours a

day, burning out his team left and right, but he wanted to touch and see everything.

169

00:11:34,534 --> 00:11:39,714

And like, I had to get through to him and like, buddy, like you don't need to see a bill

until it's ready to be paid.

170

00:11:39,714 --> 00:11:44,046

Like, like, like you don't need to see a bill coming through the process, five different

steps.

171

00:11:44,046 --> 00:11:45,747

ah And like I had to work with him.

172

00:11:45,747 --> 00:11:50,650

like, you know, those are the type of little things I often have to work with them on

first is to free up that time.

173

00:11:50,650 --> 00:11:55,232

uh The other piece of that is it doesn't take as much time as you think.

174

00:11:55,873 --> 00:12:01,175

And like, and here's here's a small suggestion to give them a just a tweak of what you

already do.

175

00:12:01,676 --> 00:12:10,551

When we're in a meeting as leaders, managers, and there's, you know, we're rehashing a

problem, a launch, whatever it may be, the leader manager comes in and says, Hey, this

176

00:12:10,551 --> 00:12:11,641

happened.

177

00:12:11,661 --> 00:12:13,026

These are my thoughts.

178

00:12:13,026 --> 00:12:14,687

Here's what I think we should do about it.

179

00:12:14,687 --> 00:12:15,868

Blah, blah, blah.

180

00:12:15,868 --> 00:12:18,549

And then they say, what do you guys think?

181

00:12:19,069 --> 00:12:22,131

You just brought that entire team your direction.

182

00:12:22,131 --> 00:12:28,174

You just made no one speak up to discount what you said, regardless of how they feel.

183

00:12:28,174 --> 00:12:32,236

So one simple suggestion is just flip the order.

184

00:12:32,637 --> 00:12:41,001

Ask them what they think first, get their perspectives as the people working on the

ground, seeing what's really going on, and then engage in the conversation.

185

00:12:41,001 --> 00:12:42,892

So it doesn't take any more time.

186

00:12:42,892 --> 00:12:53,669

just a reframing of how we approach our staff and how we change our mindset to show them

that we value their opinion and what their perspective is and how this organization runs.

187

00:12:53,902 --> 00:12:55,263

mean, that all makes sense.

188

00:12:55,263 --> 00:12:58,075

Easier said than done, perhaps, but still doable, right?

189

00:12:58,075 --> 00:13:06,910

Do you have some situations with founders or CEOs that you've worked with where you've

seen this uh kind of create magic in the business for them?

190

00:13:07,170 --> 00:13:08,050

Yeah, a hundred percent.

191

00:13:08,050 --> 00:13:21,354

uh know, just, just the amount of, of business owners who think they have a process, just

because there's just, there's steps, know, steps to do things or things are getting done.

192

00:13:21,374 --> 00:13:24,935

And I work with them and I'm like, you don't trust your team.

193

00:13:24,935 --> 00:13:26,515

You don't trust the process.

194

00:13:26,515 --> 00:13:27,936

Let's see what a real process is.

195

00:13:27,936 --> 00:13:29,636

Let me show you how to trust your team.

196

00:13:29,636 --> 00:13:33,077

And they're just like, man, this is so much easier.

197

00:13:33,177 --> 00:13:37,016

Like I am spending five hours a week on accounting.

198

00:13:37,016 --> 00:13:40,018

which I shouldn't be in at all, know, just those little things.

199

00:13:40,018 --> 00:13:52,277

And the light bulb you see uh go off in a leader's head when they finally start trusting

their team, when they take one little step, it's small and simple little steps you can

200

00:13:52,277 --> 00:14:01,704

take to transform the culture where you're really empowering your team to get things done

and just seeing that so much more gets done quicker.

201

00:14:01,824 --> 00:14:04,396

So many problems are brought to life sooner.

202

00:14:04,406 --> 00:14:06,167

And so many new ideas are brought up.

203

00:14:06,167 --> 00:14:08,278

Like that's, that's where the real magic happens.

204

00:14:08,278 --> 00:14:13,150

That the process stuff we work on to help the leaders get there, save time, save money,

all that type of stuff.

205

00:14:13,150 --> 00:14:22,304

But when they really see the work of their team come to life and bring their unique

perspectives and make things better, that's where the real magic flies.

206

00:14:22,360 --> 00:14:23,673

Okay, I mean that all makes sense.

207

00:14:23,673 --> 00:14:30,936

you say trust the process, excuse me, we've kind of been talking about trusting the team,

but you also add in trust the process.

208

00:14:30,936 --> 00:14:32,942

Are those the same thing or are those different?

209

00:14:32,942 --> 00:14:33,832

They overlap.

210

00:14:33,832 --> 00:14:37,963

mean, the process to me is always got to include the team.

211

00:14:38,264 --> 00:14:51,687

So if you have the steps, the things to do, again, I think I can see a lot about a

leadership mindset, the operation and the cultural organization by watching how they work

212

00:14:51,687 --> 00:14:52,347

in accounting.

213

00:14:52,347 --> 00:15:01,730

ah It is one of those things like the number of times I've worked with a CEO who does not

trust anyone in their business.

214

00:15:01,806 --> 00:15:05,848

to send out an invoice but themselves to a client shows me a lot.

215

00:15:05,848 --> 00:15:17,101

So you're actually saying that you use the accounting, the CEO uh finance or CEO

accounting relationship as maybe a broader diagnostic tool.

216

00:15:17,386 --> 00:15:25,028

It shows me so much about their mindset, their control, the operations they have and how

the team works.

217

00:15:25,028 --> 00:15:36,171

when you, you may be doing all the right things to have an efficient accounting process,

but if you still aren't trusting the team and you're still dipping your toe in every step

218

00:15:36,171 --> 00:15:39,813

of this, even though the process is right, you don't really trust the process.

219

00:15:39,813 --> 00:15:45,228

The process has to include trusting your team to get it to the places it needs to be.

220

00:15:45,228 --> 00:15:55,143

as it goes up and you only being involved in that final approval stage, whether it's

paying the bill or final improvement of the bill to be paid, you you don't need to step

221

00:15:55,143 --> 00:15:55,493

into that.

222

00:15:55,493 --> 00:16:01,038

So absolutely the process is the full process, but trusting the team is.

223

00:16:01,038 --> 00:16:01,818

that.

224

00:16:01,958 --> 00:16:03,058

that all makes sense.

225

00:16:03,058 --> 00:16:11,898

So if you were to step into say my business doing a few million or you were to step into

one of my clients businesses in ecommerce doing or SaaS doing you know 30 40 million

226

00:16:11,898 --> 00:16:14,398

dollars like what would what would that look like?

227

00:16:14,398 --> 00:16:20,398

You would go in and you would say hey let's just sit down let's talk and by the way I want

to just observe a little bit.

228

00:16:20,398 --> 00:16:22,778

Do you have any accounting meetings coming up?

229

00:16:23,570 --> 00:16:26,512

Yeah, a little more framework than that.

230

00:16:26,512 --> 00:16:30,073

I have a series of assessments and diagnostic tools I use.

231

00:16:30,973 --> 00:16:35,355

Some of them are, you know, software tools that I use, some are discussion.

232

00:16:35,355 --> 00:16:46,260

But you know, the software or the accounting stuff, I sit down and talk to whoever is

overseeing, you know, the admin side of things, finance, HR, etc.

233

00:16:46,260 --> 00:16:48,531

It's just conversation, right, about how things are flowing.

234

00:16:48,531 --> 00:16:52,302

You know, nine times out of ten,

235

00:16:52,728 --> 00:16:55,079

The person doing it knows what's working and not working.

236

00:16:55,079 --> 00:16:56,499

They know where the hurdles are.

237

00:16:56,499 --> 00:16:57,880

Just no one's asking them, right?

238

00:16:57,880 --> 00:16:59,680

They know there's a better way to do it.

239

00:16:59,680 --> 00:17:01,241

They know the CO needs to step out of it.

240

00:17:01,241 --> 00:17:11,484

So I tend to go to that person actually doing the work to get the intel as opposed to the

CO when it comes to those internal functions because I don't want the CO's version of

241

00:17:11,484 --> 00:17:12,304

this.

242

00:17:12,485 --> 00:17:16,646

I want the true actual workings day in and day out that are happening.

243

00:17:16,802 --> 00:17:18,403

And how does this translate?

244

00:17:18,403 --> 00:17:27,089

It sounds like what you're doing is you're really going to get the parts and pieces in

place so that the machine, if we can call it that, just operates a lot more smoothly,

245

00:17:27,089 --> 00:17:29,201

which then allows the CEO to step out.

246

00:17:29,201 --> 00:17:30,602

Then they can do visionary stuff.

247

00:17:30,602 --> 00:17:32,993

Then they can grow and they can delegate.

248

00:17:33,274 --> 00:17:41,339

you know, how does this play into or lead up to these big decisions?

249

00:17:41,339 --> 00:17:45,888

Do you find that the team gets more involved in big decisions going forward?

250

00:17:45,888 --> 00:17:52,647

Or are you, uh I don't know, does the CEO, are they able to hand off big decisions?

251

00:17:52,647 --> 00:17:58,030

Or how does all this translate into evaluating and making big decisions in a business?

252

00:17:58,030 --> 00:17:59,470

Yeah, I think there's a couple ways.

253

00:17:59,470 --> 00:18:00,670

One is the alignment, right?

254

00:18:00,670 --> 00:18:07,850

When your executive team's aligned, when your leadership management team's aligned, as

well as your entire staff.

255

00:18:08,190 --> 00:18:09,950

Decisions flow much quicker.

256

00:18:09,990 --> 00:18:13,550

You all are rowing the same boat, the same direction.

257

00:18:13,610 --> 00:18:20,130

Where we're in stall, we have one side of the boat rowing left, one side of the boat

rowing right, or some going reverse, right?

258

00:18:20,130 --> 00:18:21,930

That's when problems happen.

259

00:18:21,930 --> 00:18:24,490

so, one of first things we look at is alignment.

260

00:18:24,630 --> 00:18:28,014

And then the operational efficiency side of it,

261

00:18:28,014 --> 00:18:34,794

Yeah, one of the biggest things I can help a CEO do is get out of the operations, make it

more efficient so they can step out of it.

262

00:18:34,794 --> 00:18:46,154

And if most CEOs and founders, if you ask them, what would, know, stepping out of working

in the business, five to 15 hours a week, to work on the business, the strategy, the

263

00:18:46,154 --> 00:18:49,314

vision, the execution, what would that do for your business?

264

00:18:49,314 --> 00:18:50,714

It'd change everything.

265

00:18:51,119 --> 00:18:57,194

In some of the engagements you've had, what are some of the most shocking outcomes when

people go through this process with you?

266

00:18:57,506 --> 00:18:58,607

the freedom, right?

267

00:18:58,607 --> 00:19:10,165

I think the CEO's freedom to do what they want to do, to feel the confidence to step away

is a key thing that I always hear back and forth is just like, wow, like, now I have, you

268

00:19:10,165 --> 00:19:19,742

know, use the phrase, process I can trust where I can step out of my business, I no longer

feel it is going to explode in a negative way every time I walk away.

269

00:19:19,782 --> 00:19:25,346

The other thing is the amount of net income increase.

270

00:19:25,698 --> 00:19:29,120

that the business sees by working on these internal functions.

271

00:19:29,120 --> 00:19:31,359

It was like doing the inner work.

272

00:19:31,359 --> 00:19:37,278

We have to do the inner work on ourselves to be the right mindset for leadership in our

families and showing up how we show up every day.

273

00:19:37,278 --> 00:19:39,704

You got to do the same inner work for your business.

274

00:19:40,044 --> 00:19:44,226

And these are not sometimes the sexy flashy things.

275

00:19:44,286 --> 00:19:51,269

I'm not uh an ad marketer who's going to say, if you put X number dollars, I will 10X your

ROAS.

276

00:19:51,309 --> 00:19:53,950

I don't have that quick straight through line.

277

00:19:54,326 --> 00:20:02,685

As they're sitting in and they're seeing the alignment start happening, they see the

efficiency happening, they improve their operational strength and maturity, everything

278

00:20:02,685 --> 00:20:04,057

comes together.

279

00:20:04,057 --> 00:20:12,940

Most of our businesses that really follow our plans start seeing a 10 to 12 % increase in

net profit in 6 to 12 months.

280

00:20:12,940 --> 00:20:14,831

Yeah, no, that makes sense.

281

00:20:14,831 --> 00:20:18,515

And I feel like we're talking a lot about the benefits and the context around it.

282

00:20:18,515 --> 00:20:24,480

um I want to get to maybe if you have like a step by step framework or something like

that.

283

00:20:24,480 --> 00:20:29,424

I'd love to kind of hear that and let the audience take something away if that applies.

284

00:20:30,105 --> 00:20:35,910

while we're before we get to that point, I just want to address one situation I've seen in

some businesses.

285

00:20:35,910 --> 00:20:40,756

And that is that I feel like I talked to some CEOs and teams.

286

00:20:40,756 --> 00:20:46,110

And I see them and they all want to make this, they want to make this switch.

287

00:20:46,110 --> 00:20:55,956

They want to jump and level up to the, you know, go from 1 million to 2 million or 5 to 8

or, you know, 20 to 25, whatever that number is, they want to, they want to make this

288

00:20:55,956 --> 00:20:56,857

jump.

289

00:20:56,857 --> 00:20:58,498

But then you see them stall.

290

00:20:58,498 --> 00:21:10,376

It's like everyone's on board and the team seems to function, but getting the results or

just putting things in place for some reason just never takes hold.

291

00:21:10,376 --> 00:21:11,955

Is there a reason for that?

292

00:21:12,302 --> 00:21:13,242

Fear.

293

00:21:13,282 --> 00:21:17,542

mean, that's one of the things I talk about on a regular basis is fear, habits, and

comfort.

294

00:21:17,542 --> 00:21:21,442

I mean, these are natural elements in the human condition.

295

00:21:22,062 --> 00:21:27,262

You want to look at evolutionary-wise, biology, psychology, whatever you want call that.

296

00:21:27,262 --> 00:21:32,502

Fear, comfort, and habits allows us to survive on a daily basis and has for some kind of

time, right?

297

00:21:32,502 --> 00:21:35,642

But when it comes to innovation, growth, and change, they're the enemy.

298

00:21:35,962 --> 00:21:39,802

So that's why you have to create that mechanism to break through that.

299

00:21:39,802 --> 00:21:42,072

And that's, me, where curiosity comes into play.

300

00:21:42,072 --> 00:21:47,866

Curiosity is what allows us to look beyond our current situation limitations and dare to

dream something different.

301

00:21:47,866 --> 00:21:52,409

uh Leaders get stuck because of fear, majority of the time.

302

00:21:52,549 --> 00:21:55,291

Even, talking about decision making.

303

00:21:55,291 --> 00:22:03,797

em Nine times out of 10, a decision maker is not making the decision because of fear.

304

00:22:03,797 --> 00:22:07,819

Now we use terms like paralysis by analysis and all those things.

305

00:22:08,060 --> 00:22:11,950

The over analysis is a symptom of fear.

306

00:22:11,950 --> 00:22:21,875

because they're afraid to get the wrong answer and leaders will sit and what they know

doesn't work will not move them forward because they're afraid of trying something new.

307

00:22:21,875 --> 00:22:22,215

Yeah.

308

00:22:22,215 --> 00:22:23,716

And that's the hardest part to get over.

309

00:22:23,716 --> 00:22:28,298

Like that's a psychology, psychological component, a mindset component.

310

00:22:28,298 --> 00:22:32,160

And that's, know, I got to get COs to lower their guard.

311

00:22:32,160 --> 00:22:37,742

And that's where letting go, letting go of control, letting go of fear, all of those

components come into play.

312

00:22:37,800 --> 00:22:42,690

If you really want to innovate, grow and change, you've got to look beyond your current

situations and try new things.

313

00:22:42,690 --> 00:22:44,111

Yeah, that makes sense.

314

00:22:44,111 --> 00:22:48,953

I think there are entire topics around fear that I would love to explore in depth.

315

00:22:48,953 --> 00:22:59,037

um But for now, just in this episode, what's a framework or maybe a step-by-step

checklist, whatever it might be?

316

00:22:59,037 --> 00:23:06,220

What's something our audience who are scaling CEOs, building businesses, busy, they're the

types of people we're describing and talking about.

317

00:23:06,220 --> 00:23:11,042

What's something they could take away from this episode and say, okay, I think I can put

that into place?

318

00:23:11,052 --> 00:23:11,864

you know, next week.

319

00:23:11,864 --> 00:23:18,132

I might need some help, might need to call John, but that's something that I'd like to

start to try to implement with my team.

320

00:23:18,586 --> 00:23:27,389

I think every founder, every CEO out there, every manager out there has something in their

business and their department that their gut tells them isn't working right.

321

00:23:27,670 --> 00:23:28,550

We've all been there, right?

322

00:23:28,550 --> 00:23:34,812

Like just something that like we don't ever talk about it, but just something in our

operations or some aspect that just doesn't seem right.

323

00:23:35,113 --> 00:23:36,513

That's where you start.

324

00:23:36,513 --> 00:23:45,117

That place where your gut is telling you something is off and what you do is you map the

process and you literally you and this is where the mindset, the culture and the

325

00:23:45,117 --> 00:23:48,226

operations all come together where that connectivity happens.

326

00:23:48,226 --> 00:23:49,627

is where the magic shines.

327

00:23:49,627 --> 00:23:55,009

And so you have to have the leadership mindset to say, Hey, look, I feel something's

wrong.

328

00:23:55,009 --> 00:23:56,209

And I'm going to act on it.

329

00:23:56,209 --> 00:23:56,539

Right?

330

00:23:56,539 --> 00:24:02,532

the, you know, Carol Dweck is considered like the foremost thought leader on, on growth

mindset.

331

00:24:02,532 --> 00:24:10,075

And she warns about a false growth mindset, which is we're always thinking we always had

these ideas, but they never turn to action.

332

00:24:10,075 --> 00:24:12,316

Or the actions we take are the busy work.

333

00:24:12,316 --> 00:24:13,556

They don't really move the needle.

334

00:24:13,556 --> 00:24:17,888

We dive into the accounting, we dive into this and that, but it's not the actions we need

to take.

335

00:24:17,900 --> 00:24:25,452

So you have to get beyond that false growth mindset and understand there's something wrong

or least have the perception there might be something wrong and take the action.

336

00:24:25,452 --> 00:24:26,352

So here's what you do.

337

00:24:26,352 --> 00:24:27,493

You bring your team together.

338

00:24:27,493 --> 00:24:37,275

Anyone who touches this project process, whatever it may be, bring them all in because

everyone's got a unique perspective into how this operates and you draw out the process.

339

00:24:37,296 --> 00:24:43,367

What goes where, when and why, who touches it and lay it all out and then you start

analyzing it.

340

00:24:43,367 --> 00:24:46,326

So first you map it, then you analyze.

341

00:24:46,326 --> 00:24:54,442

You find the gaps and holes, you find the ways to make it more efficient, you find the

right tool that's going to help it all better, and you brainstorm together, and you draft

342

00:24:54,442 --> 00:24:56,904

a new process, and then you execute it.

343

00:24:56,904 --> 00:25:06,461

And the last part of that is pinpoint someone in that process who has decision-making

authority to keep it running, keep it running correctly.

344

00:25:06,461 --> 00:25:08,092

That's the best way to move forward.

345

00:25:08,278 --> 00:25:09,238

Man, I love that.

346

00:25:09,238 --> 00:25:13,420

uh we might need to put those into like a list for the show notes or something.

347

00:25:13,420 --> 00:25:18,822

As I'm thinking about it, you know, the steps obviously sound, sound good and seem like

they would work.

348

00:25:18,822 --> 00:25:26,245

But the thing that stands out to me is that, you know, we started talking about team

culture and how a team operates effectively.

349

00:25:26,245 --> 00:25:35,869

And then we're talking more about process and, uh, what you just described this one, you

know, pretty simple action that anybody could take next week.

350

00:25:35,929 --> 00:25:38,380

Almost instead of.

351

00:25:38,894 --> 00:25:52,576

team and process being at odds with each other, it sounds to me like doing this process,

or doing this type of activity, I'll call it, will bring process and team together and

352

00:25:52,576 --> 00:25:54,402

help them both grow better.

353

00:25:54,402 --> 00:26:04,311

Yeah, you know, writing my book and the more I've worked, grown in my consulting with

operations, like it's impossible to separate leadership mindset, culture and operations.

354

00:26:04,311 --> 00:26:07,765

You have to work on all the three of those simultaneously.

355

00:26:07,765 --> 00:26:18,294

You know, another good example that I'll use is we've all also been an experience where,

you know, the founder CEO manager comes into the situation and says they got something,

356

00:26:18,294 --> 00:26:20,246

you know, some, some, some hair.

357

00:26:20,330 --> 00:26:22,312

Uh, you know, on the back of their neck stood up.

358

00:26:22,312 --> 00:26:24,574

said, I'm, I'm going to, I'm going to solve this problem.

359

00:26:24,574 --> 00:26:25,114

Yeah.

360

00:26:25,114 --> 00:26:26,736

Um, but they never talk to anyone.

361

00:26:26,736 --> 00:26:27,110

Right.

362

00:26:27,110 --> 00:26:30,559

And, and, and the usually happens is they're solving the wrong problem.

363

00:26:30,559 --> 00:26:37,267

You know, and it makes the work harder and everyone's who's doing the work is rolling

their eyes and they're like, yeah, we're going to make his change for two weeks.

364

00:26:37,267 --> 00:26:37,935

They want to go back.

365

00:26:37,935 --> 00:26:38,225

Right.

366

00:26:38,225 --> 00:26:40,487

Cause they don't bring the team along with you.

367

00:26:40,487 --> 00:26:48,573

Like the most important thing in letting go is letting go of, of, of ego, uh, for our

leader and thinking you have to have all the right answers.

368

00:26:48,952 --> 00:26:54,625

being a leader should be looked at much more as being a conductor of orchestra, not a

trained conductor.

369

00:26:54,625 --> 00:27:00,749

um With orchestra, the conductor, their job is to prep the team.

370

00:27:00,749 --> 00:27:07,813

In practice, get them ready, set the tone for everything, and in concert, they keep the

rhythm, they keep the flow.

371

00:27:07,813 --> 00:27:12,095

You never see a conductor get down, scold someone for messing up.

372

00:27:12,095 --> 00:27:15,257

You don't see the conductor picking up someone's instrument, playing it for them.

373

00:27:15,257 --> 00:27:17,784

They trust the team, they trust the process.

374

00:27:17,784 --> 00:27:22,709

They're there to keep the rhythm and help the team get successfully to that last note.

375

00:27:22,709 --> 00:27:23,972

That's their job.

376

00:27:23,972 --> 00:27:26,056

And that's how we have to look at leadership.

377

00:27:26,522 --> 00:27:27,243

I love that.

378

00:27:27,243 --> 00:27:28,344

I love that.

379

00:27:28,344 --> 00:27:33,480

I'm thinking about process and team a little bit differently now, even after this short

discussion that we've had.

380

00:27:33,480 --> 00:27:35,012

So I really appreciate that.

381

00:27:35,012 --> 00:27:44,262

Well, if other people listening to this podcast are thinking the same thing I am, they're

like, gosh, this sounds like something I could probably implement in my business.

382

00:27:44,262 --> 00:27:46,655

Where would they be able to connect with you, reach out to you?

383

00:27:46,655 --> 00:27:47,758

What would be a good way to do

384

00:27:47,758 --> 00:27:48,378

that.

385

00:27:48,378 --> 00:27:48,698

Sure.

386

00:27:48,698 --> 00:27:55,223

So I have two websites, one on the personal brand site, which is johnbassford.com, just my

first last name.com.

387

00:27:55,223 --> 00:28:00,327

And my consulting firm is Lateral Solutions and the URL for that is think-lateral.com.

388

00:28:00,327 --> 00:28:03,428

You'll reach out to me through those websites.

389

00:28:03,509 --> 00:28:09,913

I'll give your guests my email is just johnjowin at think-lateral.com and reach out to me.

390

00:28:09,913 --> 00:28:16,898

Always happy to do an initial consult uh to figure out what's going on and see if we could

help you kind of break through some things.

391

00:28:17,182 --> 00:28:21,548

And just, you know, my mission, my purpose is to help leaders and organizations grow.

392

00:28:21,548 --> 00:28:22,779

And anyway, I can do that.

393

00:28:22,779 --> 00:28:23,502

I'd love to help.

394

00:28:23,502 --> 00:28:24,022

I love it.

395

00:28:24,022 --> 00:28:24,382

I love it.

396

00:28:24,382 --> 00:28:28,142

And just for the record, it doesn't sound like you've wasted your JD at all.

397

00:28:28,142 --> 00:28:29,022

Your Juris Doctor.

398

00:28:29,022 --> 00:28:31,442

You're putting all this to good use for everybody.

399

00:28:31,442 --> 00:28:35,822

So I appreciate you coming on the show and sharing your insights and perspectives with us.

400

00:28:36,602 --> 00:28:36,782

Yeah.

401

00:28:36,782 --> 00:28:41,402

And to our listeners who've joined us for this episode, thanks again for joining us on The

Breakout CEO.

402

00:28:42,662 --> 00:28:46,502

Be sure to follow or subscribe on your favorite podcast platform.

403

00:28:46,502 --> 00:28:51,422

And if you enjoy the show, a rating or a review goes a long way.

404

00:28:51,786 --> 00:29:04,111

Our mission is to promote the stories of breakout CEOs in scaling SaaS, e-commerce, and

tech companies to equip peer CEOs with valuable perspectives and confidence.

405

00:29:04,472 --> 00:29:09,354

Thanks again for joining us on this episode of The Breakout CEO.

406

00:29:09,374 --> 00:29:12,215

I'm Jeff Holman, and I'll see you next time.

Links

Chapters

Video

More from YouTube