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/

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Get in Touch with Jeff Holman ⤵️

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

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

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

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

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

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The over analysis is a symptom of fear.

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Welcome back to the breakout CEO podcast.

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

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It's great to have you on the show.

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Yeah, of course.

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

we're both JD MBAs.

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

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

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

ended up getting my MBA.

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

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

escaped the systems, right?

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So good for you though.

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

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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.

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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.

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

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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.

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

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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

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hard work I'd built in, in learning.

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the business side of the internal operations side of business.

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

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

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that's awesome.

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That's awesome.

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

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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.

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They've been down those paths.

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

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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.

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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

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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?

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This is a more meaningful decision in the business.

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

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

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than every other decision I do.

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So is that something you work with CEOs on?

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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.

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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.

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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

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how we function day day basis.

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And that really became the basis for uh

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

work and how we connect.

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Yeah, I love that.

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

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think that you've got in the book.

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

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Who do you work with?

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

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What types of companies are you working with?

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

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I'm usually working with that.

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

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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.

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I'd say the startup is a little different.

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I tend to work with them in the beginning phases.

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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

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the house.

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

stagnation.

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

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Well, that makes sense.

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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

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those as its own engagement.

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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.

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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.

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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.

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Yeah.

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So usually a couple of scenarios here.

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

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I just don't know what it is.

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Right.

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

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don't know.

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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

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third.

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And he kind of like, he hit his wall.

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

help.

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

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

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

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We want to go from 50 to 100 million.

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

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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.

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We know we could create a better foundation.

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And how do we do that?

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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

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

way, right?

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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

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team that I've got and and put a

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

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Like how do they get to that decision point?

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Yeah, so I think a couple of things.

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

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

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They know that that's not sustainable.

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mean, that's one of the first things.

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

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There's constant slowness and stagnation.

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Again, you're getting the work done.

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

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And I'd say

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

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

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They don't use the word foundation.

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They don't use the words alignment.

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

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

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

then execute on that.

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

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They take what they already do,

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and they throw more at it, right?

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

they are at the moment.

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Yeah.

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

right?

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

solution.

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

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

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

with.

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

solutions.

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

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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?

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

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

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Right.

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

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Is that kind of what you're describing?

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Yeah.

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That's a big part of it.

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That's the culture piece.

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

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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.

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

only one.

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uh There's actually a study by Google.

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

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So they did thousands of interviews questionnaires etc.

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

better than the parts.

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And what they came back with was psychological safety.

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

speak out, bring ideas, point out problems.

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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

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

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And they're so excited about it.

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

handles that issue every single day.

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

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I've known for six months.

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

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Why didn't you speak up?

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

where they did speak up?

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Why aren't you creating those mechanisms in

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

tapping into them.

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Hey, what are you seeing?

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What's wrong?

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How can we do things differently?

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

flow from the top.

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

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

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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

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

dysfunctional team.

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

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And one that...

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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?

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

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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?

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

first of all.

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

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Letting go of control.

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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.

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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.

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

steps.

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ah And like I had to work with him.

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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.

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

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

already do.

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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

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happened.

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These are my thoughts.

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

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Blah, blah, blah.

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And then they say, what do you guys think?

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You just brought that entire team your direction.

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

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So one simple suggestion is just flip the order.

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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.

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So it doesn't take any more time.

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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.

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mean, that all makes sense.

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

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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?

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Yeah, a hundred percent.

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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.

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

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You don't trust the process.

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Let's see what a real process is.

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Let me show you how to trust your team.

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

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Like I am spending five hours a week on accounting.

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

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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

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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.

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So many problems are brought to life sooner.

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And so many new ideas are brought up.

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

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

all that type of stuff.

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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.

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Okay, I mean that all makes sense.

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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.

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Are those the same thing or are those different?

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They overlap.

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

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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

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in accounting.

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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.

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

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

accounting relationship as maybe a broader diagnostic tool.

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

the team works.

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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

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

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

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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

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into that.

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

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that.

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that all makes sense.

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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

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dollars like what would what would that look like?

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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.

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Do you have any accounting meetings coming up?

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Yeah, a little more framework than that.

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

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

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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.

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

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You know, nine times out of ten,

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

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They know where the hurdles are.

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Just no one's asking them, right?

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

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They know the CO needs to step out of it.

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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

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this.

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

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And how does this translate?

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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,

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which then allows the CEO to step out.

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Then they can do visionary stuff.

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Then they can grow and they can delegate.

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

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

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

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

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Yeah, I think there's a couple ways.

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One is the alignment, right?

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

well as your entire staff.

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Decisions flow much quicker.

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

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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?

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That's when problems happen.

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

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And then the operational efficiency side of it,

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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.

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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

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

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It'd change everything.

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

people go through this process with you?

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the freedom, right?

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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

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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.

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The other thing is the amount of net income increase.

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that the business sees by working on these internal functions.

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It was like doing the inner work.

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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.

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

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And these are not sometimes the sexy flashy things.

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

ROAS.

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I don't have that quick straight through line.

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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

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comes together.

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

net profit in 6 to 12 months.

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Yeah, no, that makes sense.

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

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

that.

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

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

some businesses.

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

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

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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

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jump.

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But then you see them stall.

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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.

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Is there a reason for that?

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Fear.

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

comfort.

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

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

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

time, right?

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

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

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

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

dream something different.

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

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Even, talking about decision making.

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

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

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The over analysis is a symptom of fear.

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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.

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Yeah.

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And that's the hardest part to get over.

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

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

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

components come into play.

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

situations and try new things.

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Yeah, that makes sense.

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

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

checklist, whatever it might be?

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

types of people we're describing and talking about.

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

that into place?

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you know, next week.

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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.

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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.

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We've all been there, right?

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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.

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That's where you start.

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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

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operations all come together where that connectivity happens.

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is where the magic shines.

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

wrong.

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And I'm going to act on it.

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Right?

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

mindset.

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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.

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Or the actions we take are the busy work.

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They don't really move the needle.

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

to take.

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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.

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So here's what you do.

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You bring your team together.

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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.

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

analyzing it.

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So first you map it, then you analyze.

341

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

a new process, and then you execute it.

343

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

That's the best way to move forward.

345

Man, I love that.

346

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

347

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

they would work.

348

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

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

Almost instead of.

351

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

help them both grow better.

353

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

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

355

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

you know, some, some, some hair.

357

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

358

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

359

Yeah.

360

Um, but they never talk to anyone.

361

Right.

362

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

363

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

They want to go back.

365

Right.

366

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

367

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

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

trained conductor.

369

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

370

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

rhythm, they keep the flow.

371

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

372

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

373

They trust the team, they trust the process.

374

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

375

That's their job.

376

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

377

I love that.

378

I love that.

379

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

discussion that we've had.

380

So I really appreciate that.

381

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

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

383

What would be a good way to do

384

that.

385

Sure.

386

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

first last name.com.

387

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

388

You'll reach out to me through those websites.

389

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

390

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

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

392

And anyway, I can do that.

393

I'd love to help.

394

I love it.

395

I love it.

396

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

397

Your Juris Doctor.

398

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

399

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

400

Yeah.

401

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

Breakout CEO.

402

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

403

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

404

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

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

406

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