In our new episode I get to sit down with Sheila O'Sullivan, a formidable leader renowned for her strategic acumen and innovative frameworks that bolster effective communication.

Throughout our conversation, we explore Sheila's extensive experience in scaling startups to remarkable success, as well as her insights into the intricate dynamics of trust-building and high-stakes conversations.

In doing so, we illuminate the significance of understanding communication styles and the importance of fostering environments that nurture collaboration and inclusivity. Our discussion not only highlights the challenges women face in traditionally male-dominated industries but also underscores the transformative power of mentorship and shared experiences in shaping leadership trajectories.

Our Guest This Week:

Today we have a 🌟 High-Stakes Trust Builder 🌟 in our midst!  

Sheila O’Sullivan is a powerhouse strategy, operations, and go-to-market leader who has scaled startups from vision to multi-million-dollar exits. Known for her rare blend of systems thinking, data-driven decision-making, and human-centered leadership, she has built diverse, high-performing teams and guided them to create customer experiences that accelerate growth and deepen loyalty. 

A certified communication style coach, Sheila developed the *Communications Comfort Zone* framework, a battle-tested approach that helps leaders break down barriers, win trust rapidly, and master high-stakes conversations. Her work spans building and optimizing multi-sided platforms, reducing friction in fast-growth, acquisition-fueled environments, and championing women’s advancement in Web3 and emerging tech. With a track record of turning complexity into clarity, Sheila is on a mission to help leaders translate bold visions into reality while creating companies customers and employees love.

Takeaways:

• Sheila has extensive experience in building successful enterprises and emphasizes the significance of strategic communication.
• The discussion reveals how societal narratives have historically constrained women's roles, underscoring the need for a shift in leadership models.
• Communication effectiveness is stressed as a critical skill for leaders, particularly in navigating complex team dynamics and fostering collaboration.
• The episode highlights the transformative power of understanding one's communication style and adapting it to enhance interpersonal effectiveness within professional contexts.

Chapters:

02:37 Transformational Narratives and Intentions

11:18 Transformative Education and Career Reflections

15:30 The Journey of a Pioneer: My Mother's Business Story

25:05 Resilience in Business: Navigating Challenges and Growth

35:03 Transitioning to New Communication Frameworks

40:09 Understanding Communication Comfort Zones

44:21 Transition to Communication Insights

Burning Questions Answered:

1.How do you build trust and credibility in male-dominated industries without losing yourself?

2.What does it take to survive setbacks like losing your biggest client and still scale to a successful exit?

3.How can leaders use communication frameworks to unlock team potential and navigate high-stakes conversations?

4.Why visibility can be both a gift and a crutch for founders—and how to balance it.

5.What it really means to empower your team so the business thrives beyond the founder.

Favorite Quotes:

“It’s not too late to do the thing that you think you wanna do.”

“Sometimes it’s better to look in places where you can just soar.”

Guest Offers & Contact Information:

https://www.linkedin.com/in/sheilalosullivan/

Follow the #WisdomOfWomen show for more inspiring stories and insights from trailblazing women founders, investors, and experts in growth and prosperity.

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RSS Feed: https://feeds.captivate.fm/womengetfunded/ 

Coco Sellman, the host of #WisdomOfWomen, believes business is a force for good, especially with visionary women at the helm. With over 25 years of entrepreneurial experience, she has launched five companies and guided over 500 startups. As Founder & CEO of A Force for Good, Coco supports purpose-driven women founders in unlocking exponential growth and prosperity. Her recent venture, Allumé Home Care, reached eight-figure revenues and seven-figure profits in just four years before a successful exit in 2024. A venture investor and board director, Coco’s upcoming book, *A Force for Good*, reveals a roadmap for women to lead high-impact, high-growth companies.

Learn more about A Force for Good:

Website: https://aforceforgood.biz/ 

Are Your GROWING or PLATEAUING? https://aforceforgood.biz/quiz/

FFG Tool of the Week: https://aforceforgood.biz/weekly-tool/ 

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Growth Accelerator: https://aforceforgood.biz/accelerator/ 

Welcome to the Wisdom of Women show.

We are dedicated to amplifying the voice of women in business.

A new model of leadership is emerging and we are here to amplify the voices of women leading the way.

I am your host, Coco Sellman, five time founder, impact investor and creator of the Force for Good system.

Thank you for joining us today as we illuminate the path to unlocking opportunities and prosperity through for women led enterprises by amplifying the voice and wisdom of women.

Today we have a high stakes trust builder in our midst.

Sheila o' Sullivan is a powerhouse strategy, operations and go to market leader who has scaled startups from vision to multimillion dollar exits.

Known for her rare blend of systems thinking, data driven decision making and human centered leadership, she has built diverse high performing teams and guided them to create customer experiences that accelerate growth and deepen loyalty.

A certified communication style coach, Sheila developed the Communications Comfort Zone Zone framework, a battle tested approach that helps leaders break down barriers, win trust rapidly and master high stakes conversations.

Her work spans building and optimizing multi set multi sited platforms, reducing friction and fast growth acquisition fueled environments and championing Women's advancement in Web3 and emerging tech.

With a track record of turning complexity into clarity, Sheila is on a mission to help leaders translate bold visions into reality while creating companies that customers and employees love.

We are so excited to have you today, Sheila.

Hi Koma.

Welcome.

Thank you.

It's great to be here.

I'm excited to be doing this with you.

I'm so excited too.

We've had all these wonderful little ways to connect.

I think.

How do we first connect?

I think we first found met at a conference.

Yeah, you were speaking about communication.

It was a technology platform.

And then we met randomly at Chief.

Yes, exactly.

We became members together in the whisper group with Carrie Kirpin.

Exactly.

I can't wait to see where we go next.

So what is a book written by a woman that has significantly influenced your life?

Okay, I'm going to take a little bit of left turn with this.

It was really more of a course and a book.

It was a course on women in film noir that I took at Georgetown.

One of the texts we read was by M. Kaplan.

The concept of this course and the book and the articles in this book talks about the deliberate choices that Hollywood made Post World War II to create content that convinced women that they needed to leave the factories they'd been working in when the men were overseas and go back home to their family lives.

It was a message essentially of you need to, you know, re Establish the natural order of things by telling stories of horror and terrible things that happen to women when they step outside of the traditional order.

One of the greatest examples of this is the movie Mildred Pierce.

And so Anne Kaplan's book has this article by Pam Cook talking about Mildred Pierce.

If you haven't seen it, there's a.

An updated version that I don't think I've seen.

But the original version had Joan Crawford, and she's fantastic.

In this movie, essentially, Mildred Pierce is a woman who develops her own business because her husband's a bit of a slacker and becomes extremely successful in this business.

Leaves her husband, takes on a lover, something.

You know, the movie starts with something terribly tragic happening to the lover.

And the way the filmmakers craft the film, they're implicating Mildred in his death right from the very start.

So you're watching Mildred this whole time with suspicion and like, you know, watching your actions.

Anyway, so what it did for me was it.

It transformed the way I thought about narrative and decision making.

It was the first time it really occurred to me that in art and business, in advertising and communication, and I think you see a lot of it now, if you watch Mad Men or something like that, you see it's much more prominent to talk about these things.

Back then, it wasn't apparent to me that people weren't just getting up and telling a story based on their experience.

I thought it was much more innocent.

What it really is, is there's an intention and an agenda behind what people are communicating.

And we are really all better served if we understand and try to figure out what that agenda is while we're consuming this information.

And it also teaches us how to speak to others when we know what our intention is and we want to get our attentions crossed to think about what do we include?

What do we leave out?

So it was like the veneer was sort of torn off of everything I saw around me.

And to try to, say, be a little bit more skeptical about, like, why are they delivering the message in this particular way?

And just ask the question to figure out what was going on behind the scenes.

So that was just transformational for me, for sure.

Fascinating.

And, you know, there's so many paths we could go with this, but there's.

There's that idea that we have been in this narrative as women to keep ourselves at home and not take a bigger role.

There's that narrative, but there's also the notion you work on with clients, too, around what creates good communication when you're working with a Team.

Right.

Even as you're saying that I'm like, what's my intention attention right now?

What's my motivation?

Right.

Certainly it's all these pieces say more about how it has impacted this notion of narrative and intention and manipulation.

How it has helped you or held you back in your career.

I think the way that it's helped me, I am sort of naturally a person who doesn't take things personally, sometimes to a fault.

That's.

I don't.

It wasn't a skill I developed.

It was literally just the way I kind of came out.

I think that helps me because in most cases I don't assume negative intention.

I assume there's something else going on and it's got nothing to do with me.

So I think that has helped me.

I think it helped me in being in some pretty male dominated industries.

I did not read things as gender coded for a very long time unless it was really slapped me across the face that was gender coded.

And then I was like, oh boy, that's a shock.

I think it helped me not second guess myself or give myself an additional handicap because I was a woman in these male environments.

It may have been there and I just didn't notice it.

And I think that ignorance helped me in a weird way.

It just helped me kind of assume that I was being treated like everybody else, even if I wasn't.

And then again, when I realized when it would cut through, it was because it was clearly like, okay, no, you're not supposed to be here.

The intention was you're not supposed to be here.

And we're going to make sure that you understand that you're not really supposed to be here.

Yeah.

Oh, wow.

I think about how all the different versions of that for women, for underrepresented people, for different socioeconomic class, you know, people in different.

In the, you know, in crossing boundaries, barriers, et cetera, and how all pervasive it can be and how, you know, there is being able to understand that a lot of this stuff isn't about me personally or you personally.

Right.

It's what's in the narrative, it's what's in the context.

And the power of seeing it helps you not be hurt by it as much.

Exactly.

One of my favorite jobs was on the trading desk at DLJ in high yield loans and distress loans.

And I got that job because my first job out of college was at a law firm where the clients were doing this work.

And I thought I wanted to be a lawyer and change the world for various reasons.

But I Made the very good decision of saying, I'm not going to go to law school without seeing what lawyers do in real life first.

So I went to Erin Gray.

Very small firm that was a growing firm, was a boutique law firm.

The partners had left the big law firms in New York because they wanted to create a different version that was more human, more client services.

They're fantastic guys.

I just had a wonderful experience with them.

But I learned I didn't want to be a lawyer.

And so I went to go work for dlj, which was one of our clients.

My boss on the desk, the guy who ran the desk, was one of the most brilliant people I have ever run across in my life.

I have so much admiration for him.

He was literally creating new financial products.

Just a genius.

And so he hired me to the desk.

At the time, the trader on the desk was someone I knew socially because he was friends with my boyfriend.

And when I got to the desk, this trader said to me, oh, you know, I didn't know that you were in this space.

And I said, yes.

And he said, oh, well, you realize you can't tell your boyfriend anything we do here.

That was one of those moments where I was stunned.

I had literally just been hired by a brilliant man who, you know, didn't care what gender, what race.

He just saw me as a smart person who could help him achieve his goals.

And he was like, yeah, yeah.

To then walk straight into another guy on the desk who was like, oh, yeah, you're.

You're the little girlfriend of a friend of mine, so how should I take you seriously?

And that was a message, and it was a great lesson in, you know, some people are just never going to be won over.

I knew ultimately that I wasn't going to be able to return after business school to that desk because that trader was in line to be one of the senior people at that desk.

And I think there's plenty of other spots where I know they're not going to look at me the same way as he looks at me.

So I'm just not going to try to challenge that head on.

Yeah, sometimes it's better to look in places where you can just soar, especially early in a career.

Right?

Yeah, exactly.

They're real champions.

There are.

Yes, absolutely.

So let's go.

You know, I want to.

We've talked.

You've given us a couple of moments already in your life, I think, already presenting our listeners who you are as a person.

Your intelligence, your willingness to go into new areas, your financial.

You're also Very adept with communication and tell us.

We, we need to know more about you.

So tell us about the moments of your life.

Three poignant moments that have really shaped who you are.

That maybe have been personal, professional, bold moments, scared moments, heartbreaking moments.

What three moments?

Tell us this is who Sheila is.

I grew up Catholic and ended up at Jesuit schools.

I made the choice to go to them because they were the best education at the time.

I was like, of course I'm going to go to Catholic school school.

So I'm gonna end up at the best Jesuit education institutions I could.

But it really was transformational in my thinking and going out in the world.

The Jesuits do a phenomenal job of two things in particular in my mind.

Constant questioning and self examination and the benefit of that and not being afraid of that.

They do that most famously in a religious context where they ask you to question your relationship with religion and God and everything and examine it really fully.

But they do it also intellectually where they teach you to challenge concepts and think critically.

The other thing they really do is imbue in you this sense of for the greater glory of God to be a man or woman for others.

We're here on this earth and if you have certain gifts, you're meant to share those gifts with the world to make the world a better place.

It's just that simple, right?

The people that I knew in those schools, the people who I've come up with in life, really embody and have that sense of when you go out in the world and you build a business or you interact with people or you try to create value around, you're doing it for yourself, sure.

But you're also doing it for the greater glory of the world around you.

That doesn't leave me.

It's always there and it always manages the decisions that I make.

One of the second things I'll share with you is the.

A big moment of realization for me was I left the law firm.

I went to work at dlj.

I went to business school full time and went back into Wall Street.

When I went back, I went to Lehman Brothers and landed in the high yield trading space.

I can't tell you how much I loved the environment of the trading desk.

I loved the energy of it.

I love the constant change and curiosity and had the opportunity at Lehman to sit with them on the mortgage backed securities desk for a while where there were literal rocket scientists designing the product.

Obviously that all created one of the bigger problems that ended up taking Lehman Brothers down.

But when I was there, it Was still this environment of creating financial instruments for natural buyers.

There are buyers who need different things based on the reasons they're buying the securities in the first place.

And so these geniuses were literally ripping apart loans and taking pieces of those loans so that they could serve as different investors.

It got out of hand for various different reasons that I think have nothing to do with what they were creating.

But it was really cool intellectually.

It's all fascinating.

For me, I went to the high yield desk and it was a great group of people.

It was much more well established than the desk I had been at dlj.

And it was bonus time.

I don't remember if these were the exact numbers, but I'll just say there were two sales guys.

One got paid like a 7:50 bonus, the other got paid like a million dollar bonus.

And you know, I was like, what?

That is so much money.

That's insane.

But I just remember being really surprised because the person who got 7:50 was upset in a mood.

I was so confused.

I was like, you just got paid a huge amount of money.

Like how could you possibly be upset?

But he was upset because the other guy got paid more.

And the realization I had at that moment was, I am in the wrong place.

Because I would have been thrilled with that 750.

And here's what it meant to me.

It meant to me that making money for the sake of making money was not what drove me and it was what was driving the people around me.

And because of that, I was never going to be as good at that job as they were.

And it was almost like a disservice for me to be taking up the seat that I was taking up.

I had competed for that seat because there are limited numbers.

I just like, I am in the wrong place.

Sometimes you see things better in hindsight.

It occurred to me that one of the things that was so important to me for getting up every day at DLJ and at the law firm that I was working at was we were building something together.

And I thought, aha, that's the missing piece.

At the same time, my mother had just started a business.

So my mother had a phenomenal career.

She's just got like this amazing story.

She was a schoolteacher when I was little.

She left being a schoolteacher to start working part time as a marketing copywriter for a manufacturing firm.

Because school teaching was paying like nothing.

They were paying her, I think by the article.

And so they hired her.

And then all of a sudden she was like, wait a minute, they're Paying me by the article.

They only gave me these two assignments.

Let me go around and get more assignments.

And without, you know, being told she had created this whole marketing library.

And they were impressed with her initiative, her writing, everything.

So they decided to hire her full time and then promoted her to sales management.

Then they sent her to University of Chicago Business School to get an executive MBA.

They promoted her to president of the company.

The only woman in that space, one of the few women in that industry.

She's a recognized pioneer.

It's food service equipment manufacturing.

She's a recognized pioneer in that industry.

And then she leaves that business in her early 50s and decides, I'm going to retire.

And we're all like, yeah, right.

And then she comes with a partner and says, you know what?

I'm going to start this.

We're going to fund this business.

He's going to fund it with me.

I'm going to build it.

That to me, was way more attractive than what I was doing at Lehman Brothers, but it wasn't going to pay me enough in the beginning.

She was approached by a team out of Silicon Valley who said, we like this concept that you've built, but we think you should have an E commerce component, and we think we should raise venture capital.

I said to her, that is something I want to be part of with you for sure.

She said, you're coming to the investor meeting with me.

I said, sounds great.

We go to the investor meeting.

It's the principal lead for the VC round they were looking to raise.

She was on the way up saying, I don't know what to tell these guys.

I don't know anything about finance.

I'm a salesperson, a marketing person.

I've built my business through networking, and I don't know what to talk to these VC guys about.

And she's like, I'm glad you're with me because you have the finance language.

And I said, sure, that's fine.

Well, we sat down and they said, tell us your story about why you're building this business.

So we're sitting across this big boardroom table, and it's.

We're on one side, and on the other side of the table, it's the principal, the associate, and the partner.

First the associate was like this.

And then he leaned forward to put his elbows on the table.

And then the principal, who had been like this, you know, foot crosses him.

And then the partner uncrossed his arms and leaned Forward on the table.

I was like, we've got this money.

And we did.

And there are a lot of things that happened after that, but that's just.

Those were some pretty big moments.

Wow.

I love these three choices that you just shared with us.

These three moments.

It makes sense, like going to a Jesuit school, to not only have a good education, but be really grounded in being of service to the world and sharing your glory with the world.

I think that's profound.

This whole conversation about being in finance and realizing my husband's in the finance world and he's, you know, like, they are truly many of them in the business to make money.

And that is it.

And it is a different motivation, certainly for me.

I love to make money, but it doesn't light my heart out like that as an endpoint, it's in service sense.

So I can do more cool things and create more opportunities.

You know what I mean?

So I love that.

And then you have this mother.

Yes.

Holy cow.

So she got the money and then at some point you got involved with the business?

Yes, right after that.

Sadly, it really wasn't even that long.

I can't remember what the period of time was the tech bubble burst.

We hired a whole team of really bright developers and like implementation teams, technology implementation, and launched this product and literally, literally couldn't give it away to the customers.

They just were not ready for it.

The business was a group purchasing organization.

We negotiate contracts with suppliers with financial incentives or better terms.

In many cases it was tiered rebates because we were doing this on custom goods and components for manufacturers that aren't part of a list price catalog or something like that.

And you create this group of buyers who then takes advantage of those incentives.

And the more volume you drive from those buyers to the suppliers, the more the suppliers benefit, the more the buyers benefit.

And it's this great little cycle of.

Of creating this group through these transactions.

And the group purchasing organization gets paid a transaction fee, like a marketing fee or an administrative fee from the suppliers.

That's essentially for better customer acquisition, faster acquisition, and better retention.

So that's.

That's the concept, that's the model.

And so it's this really great platform, objectively, from the outside, when you look at it, the technology will make everybody operate more efficiently.

24 years later, customers are finally ready for it.

In theory, it was a great idea, but it was not the top of mind agenda for what our customers are trying to do with their business.

You know, they were competing with China, they were competing with overseas manufacturers who, who were either selling goods at a lower price or in some cases stealing their ip.

They were dealing with material price disruptions and everything they were dealing with strategically had nothing to do with technology and efficiency.

So how did you stay alive, first of all?

How did the business continue to function and how did you get to a successful exit?

So we had to that situation.

Yeah, we had to lay off this really big group of talented developers and implementers because it wasn't work for them.

I think we were fortunate in some way that the VCs we raised money from were very focused on technology firms developing new products.

We didn't need the technology to do the GPO business.

There have been gpos in healthcare and other spaces for decades and these businesses have run really well without the need for any kind of like technology piece.

So we didn't need it to make money.

We had a different revenue model and a different revenue proposition.

They said, you guys are one of the few that actually have the ability to make money.

You're losing money because you've got the staff, but once you cut the staff, you have the ability to make money and provide a return for us.

And we did.

We didn't give them the return they were expecting, but we eventually did give them a really strong return.

We raised money from a group of investors and the management team and it was profitable.

It was profitable at that point for many years.

We remained profitable through losing our biggest customer.

We remained profitable through the Great Recession.

You know, it wasn't great, but we remained profitable.

Part of the reason we remained profitable was that we retained a small group of developers from that original team who took the platform they were building.

Basically like document transactions and managing payments.

It was a payment management system.

They applied it to our own internal business operations and allowed us to remain really efficient and not have to add a lot of headcount.

As we were adding lots and lots of customers, we essentially just doubled down on our real base value proposition.

Just do that and don't worry about doing anything else for many, many years.

Let's do everything we could possibly do to make our buyers connect with our suppliers and get them to do business together.

Our whole entire focus was around anything that we could do to make that process happen without friction, to make it happen more frequently, to add the right buyers and sellers, which is one of the geniuses of a GPO model, is you can grow just in many different ways.

So we focus solely on that for a very, very long time and did nothing outside of the scope of our core business.

And that's how we ended up being an attractive target for a strategic buyer eventually.

See, that to me is such an illustration of what makes a great entrepreneur.

You keep figuring it out.

Yes.

And a lot of times things don't go the way you expect.

You think, okay, I got VC money.

The next thing is we're going to grow and then we're going to exit.

And that's not what happened.

In fact, you bought them back and there was probably a lot of, a lot of heartache and pain and struggle during that.

Right.

And that's the truth.

Eventually you get to your, your exit, your big exit.

I just feel like in my own experience that's the story people want to hear, is that you exited, but really the story is everything that you had to grow through.

Exactly.

To get there.

Exactly.

What kept you in all that time?

What kept you going in this business, in this challenging environment?

Why didn't you give up?

Leave?

What kept you?

It was a lot of different things.

We had a really great customer base.

They loved us.

And the reason I know they loved us is two things would happen.

They would come to us constantly with recommendations for people they wanted us to meet.

By far, our best way of growing was referrals from existing customers.

We would have, you know, someone we worked with leave and go to another firm and the first thing they would want to do is come back and join our group.

So we did really well in that respect.

We pleased the heck out of our customers.

It ties back to Louise's experience as a teacher.

I'll get to that in a second.

So we had great customers who really supported us and stood by us through a lot of tough times.

We deliberately incorporated them into our business through advisory committees.

They were member advisory committees and supplier advisory committees to help us.

They were fantastic because if we had ideas about what we thought we should do, this was our testing ground.

It would nip something in the bud really fast if they said, actually no, there's no interest for us.

And that.

Yeah, exactly.

But what it did for them, especially on the buyer side, was it was made up of purchasing managers and procurement managers at mid sized manufacturers who do not have a lot of opportunity, or at least at the time didn't have a lot of opportunity to network with their peers to get out and be in the Spotlight to be thanked for what they do.

It was not a glamorous role.

And what we did was give them a space to have their voices heard by someone outside their business, have their voices heard by their peers.

Through these committees.

We had two conferences at every year where we brought our buyers and sellers together and gave them opportunities to educate on something that they were working on in their business that they wanted to share with their peers.

We also gave them.

This is where it goes back to Louise's teaching experience.

We also gave them awards every year.

I tend to lead with my head, and I think Louise is way more intuitive than I am.

And intuitively, she just had a sense of why this works.

But I had to see it to understand why it worked.

We had a customer survey done, and I do want to make sure I tell the greatest story.

This is another reason why I stated it from that customer survey.

But before I tell that story, we did a customer survey, and the outside firm we worked with made distinctions between what people state motivates them and what we can understand motivates them through the different ways that they were asking the question.

So when they asked specifically about those awards, everyone stated that they don't matter.

But when we looked at what really does motivate them, that recognition did matter.

That's something that Louise, I think, knew from being a schoolteacher, is that that positive reinforcement and that recognition in public and all of those things encourage the behavior you really want to see in a group.

I think we had a really loyal set of customers based on that.

One of the other reasons was we also had a fabulous team hiring for a small business that is not in a sexy environment.

We didn't have great pay, but we weren't paying poor wages.

But we really tried to make it a place that we offered a ton of professional development opportunities.

We brought in a lot of professional development opportunities, but we also tried to have as much fun as possible.

We used to dress up in costume at the conferences.

We would have skits and games, and we did a lot of fun things just as a business.

But everybody we hired, I think you just naturally kind of screened for people who have a good sense of humor and laugh easily, so that when you're going through the tough times, somebody can crack some kind of gallows humor joke and everybody can laugh at it, because that's going to be the way you process and you deal.

We really had a team that worked like that.

Some of the greatest memories of that whole experience was during this customer value survey.

One of the questions was Meant to discern.

What did Prime Advantage mean to you?

I think we had this idealistic choice at the top that was, if they're a strategic partner that I don't want to, you know, make any decisions without, that was like a seven, right?

And then one was, I don't think of them as a partner at all.

So there was a spectrum in between.

We had one person who answered the survey somewhere in the middle.

We had provided a text box for further explanation for them to freeform their answer.

We had it up on the screen in the conference room as our guys who did the survey were reviewing the information with us.

The answer in the free text was crime.

Advantage is like a spare tire.

They're there when you need them, but most of the time, they're just along for the ride.

We all died laughing instantly.

It was humbling.

It was not what we wanted to hear.

It was outright hilarious that somebody put it that way.

And of course, the joke is like, well, there's our new tagline.

And I mean, you know, we just immediately went into the permutations of, like, where could we actually take advantage of this?

You know, those moments, like when just.

A spare tire for you, right?

You're going to add that to your mark and make that your tagline.

Our new logo was a spare tire.

Like, I mean, just like, how do we just riff on, like, how funny this was?

And it's still.

I still laugh when I think about that moment.

If we had been a different organization, if we had a different relationship with customers, if we had a different relationship with each other, if we had a different relationship with our investors at that point, I think it would have been a lot harder to come in and recover from things like that.

When we lost our biggest customer, I remember the moment they told us that they weren't renewing their contract.

And I.

It was tough because we.

We didn't anticipate it.

We knew we were up for a tough negotiation for the renewal, but we didn't anticipate them straight up walking away and taking their cards off the table.

However, my instant feeling was, too bad for them.

We're going to keep going, get a competitor of theirs on board and take their customers.

And we did.

We didn't take all their customers, but my feeling was almost one of relief because they were a very large customer.

They were not a great customer.

And it taught us two or three things.

You know, one, that we had to diversify a bit more so that we didn't have as much in one basket.

It taught us that we could survive severe blows.

The lesson that I took out of it was at that point we already had long term trusted employees.

We needed to, specifically myself and Louise, spend more time on strategic work both around keeping our customers and finding other ways to make money.

For that diversification process, we needed to incorporate more formal strategic exercises and planning and vision than we had before.

And the whole reason for doing that was give everyone, you know, a guiding North Star objective.

Help them understand how their daily roles connect to the value that we bring to customers.

We had done this giant survey of our customers that we called our customer value survey so we could see how they get value and how we were delivering it.

They could say, all right, these five things I'm doing every day I see how they correlate to customer value.

We gave them the freedom to come to us and say, all right, I'm going to make these five things my North Star.

That's going to be what I spend my time on every day.

And when questions come up about how to make decisions with customers, with coworkers, with my daily work, I'm going to make those decisions without having to run to someone on the management team.

Because I now know within this framework and this parameter that this is where we're going.

And so it allowed us to give them more ability to drive revenue on their own without involving us in everything, which was a process.

I mean, it was not something that happened overnight.

Goal setting is an art and a science.

Some people embrace it immediately, other people need more help on it.

It was a several year process for us to get that going.

But the benefit of it was by the time that we were ending up selling, we really had a solid team rowing all in the same direction.

Yeah, I know in my experience, this is one of those indicators that separates the girls from the women when it comes to building businesses.

That belief that everybody just needs to do their job, whatever that is, they don't need to know everything.

But companies that get clear and reiterate what those big, big ideals are and then translated into measurable, specific goals and then KPIs, like, that is so simple and yet it really does create a business that can run and be sold.

Exactly.

You can't do that if you don't have that.

Your business has to have you.

Right, Exactly.

Louise was the very visible founder of our business early on her career.

A man who was a champion for her, who told her, get visible.

That was his advice to her.

And she, you know, like a very good soldier back then, took that and ran with it.

And she understood that visibility is very important.

But by the time she was running Prime Advantage as the CEO, she recognized that visibility could be a crutch.

And she had to spend this time very clearly empowering this really fantastic team that we had developed over the years to be able to be seen as the business decision makers as equally as her so that it could continue on past whatever she decided her future was going to be.

Yeah, give people the reins and let them make mistakes.

It doesn't happen overnight, as you were saying.

Yes, exactly.

So I want to pivot now because I could talk to you all day about your founder story, exit story, how you scaled, how you.

I'm dying to know how you bought the back from Venture.

There's, there's like, there's like so many different ways that we could unpack all of this.

But I really want to move to what you're doing now because here you are, this finance person, MBA person, trader, desk person who shifts from there and helps build a whole empire with your logistical empire, technology.

And you've said before that you're very analytical and I know that you are, and you have managed to move yourself into a place of communication.

So help us understand what you're doing now and why you've chosen to go into communication and comfort zones.

Tell us about this framework and what you're doing today and why.

Absolutely.

I learned this framework because I needed to learn this framework.

Yes.

I.

We teach what we need to learn, right?

Absolutely.

So I, you know, I think I'm a relatively decent communicator, but it was very clear to me that the way I was communicating with some people it worked all the time, and with other people it worked only part of the time.

And I knew it wasn't them.

Like, this was the thing that was bothering me about it.

Like, I knew it wasn't them because they weren't incompetent or unmotivated.

I will share a framework that I learned frameworks because I'm analytical.

Frameworks just really help me understand the world a lot better.

I'm pretty good about not being so black and white or literal about them.

I use them as a tool, not a weapon.

And I strongly like, enforce as I'm teaching these tools.

They are tools, not weapons.

And we don't put people in boxes and force them to stay there.

We hired consultants to help our team on consultative selling.

And they introduced two frameworks that hit me between the eyeballs like, oh, okay, now I get it.

The first was talking about when you have expectations of another Person, you know, work environment, perfect.

But you know, really in your personal life too, if you have expectations of another person and those expectations are not being met, you've got to analyze why they said you can break it down to four things.

It's either the expectation wasn't communicated or agreed upon, right?

So it's a communication issue, it's an organizational issue, meaning there's something in your organization that's preventing them from completing the task as you expected.

It's a skill issue.

So they don't have the skills to get it done, or it's a motivation issue, they don't want to do it.

A motivation issue is your biggest problem because that is really hard to change.

If you're a manager or a leader, that's your responsibility.

You've got to not only train them in the skills, but make sure they actually did it.

You have to stick around long enough.

In startups and in businesses that are growing, one of the faults we have is we're like, here, take it, go do it.

And instead of taking that extra time, go do it, and then show me what happened.

Do that three more times and then I'll be confident that you can do it on your own without me.

The organizational issue, that's also your job as a leader to figure out if there are organizational issues.

But the communication piece, that's where I was like, okay, this is a little thicker, right?

Because I thought I was communicating the expectations very clearly.

So why in the world is this still?

I could tell it wasn't skills, I could tell it wasn't motivation.

I could tell it wasn't organizational.

And so that's where they introduced to us this concept of Merrill Reed Personality Index.

And it was a framework two industrial psychologists developed years ago around how you assert yourself, whether you do it for tell assertive or ask assertive, and how you how comfortable you are displaying emotion.

Whether you're really comfortable and tend to display emotion, or you're less comfortable and you control emotion, it creates this matrix.

If you are on the ask assertive side, you tend to command people by a question.

So I am on the ask assertive side.

I would say things to my team like, can you guys get this by Friday?

And half the team would get by Friday, half the team wouldn't, and the team that wouldn't.

Lo and behold, they're on telecertive.

I didn't tell them what to do.

I gave them an option.

It was a question that's on me to know whether or not you're getting what I'M saying.

And so I, you know, just one really quick like tweak that we learn is use statements rather than questions when you're directing someone to do something because it's going to be more clear to that person.

So years of studying this, working through this, when I wanted to create this course on Maven, my whole goal was to fit, help people figure out where they sit, how they can just easily get a handful of tricks that you can quickly identify to change the way you're communicating in order to be more effective, especially when you're communicating with someone who is different from you.

So I started calling it communication comfort zones because that's what it is to me.

We get comfortable communicating in a very specific pattern.

And if we're not getting uncomfortable, we're actually missing 75% of the population.

One of the things I tell people is over time it gets easier and easier.

But initially when you're learning this, if you don't feel uncomfortable, you're probably not actually communicating the way you think you are.

Your intentions are potentially being misread.

So I developed this course to teach it and I do workshops at companies and some one on one coaching.

But the whole idea is helping people understand where they sit and how to over time you can develop an instinct for, you know, this person.

And I have a constant communication issue.

I'm going to tweak, I'm going to change things around trial and error and you might be able to get it.

But what this framework does for you is helps you really understand what's going on behind it so that you're not guessing when you're trying to make those adaptations so that you're actually doing something deliberate and intentional to get your point across.

Wow.

What I love about this, and it makes so much sense to me because as a founder and a leader, if you're trying to grow your company, you are trying to get people to do things differently.

It's like adjusting behavior over and over again.

Even if you change a system or improve a system now, they've got to get them to use the system.

So it's all these little micro changes happening.

If you aren't paying attention to this, you're not getting the most out of your team.

One of the most common pieces of advice I end up giving is for people who are on the side of the matrix where everything goes fast, decisions are fast, meetings are fast.

For those people, the most painful, uncomfortable thing to do is slow down, to speed up.

If they're not slowing down, they're going to end up, pulled back.

They think they're on step 10, they're going to get pulled back to step three.

If you just take a second to slow down and really make sure the team is on board with you and they're not just saying they're on board with you because they, they want you to leave the room.

You have to take the time and slow down to speed up.

You'll go much faster if you throttle it back a tiny bit, feel uncomfortable throttling it back, and then you can go back to your normal speed.

Yeah, I know.

That's such powerful advice for us all, including me.

I happen to be one of those fast moving.

How I've adjusted to that is having certain things that I know are most important in the business that I just repeat over and over again.

We're going to come back to this again this week and we're going to come back to it again next week and we're going to come back to it again.

You know, just.

Just to make sure that I have not moved too fast and not because I oftentimes with my team have found.

Well, I already told them that that's always a right.

I told them I've already trained them.

They're not doing it right 100%.

And like, I can.

I will tell you, in a lot of cases, there's a way of reacting to discomfort that happens on that.

You know, what I'll call, like, less fast side of the matrix.

And it's acquiescing.

It's.

I'm going to say yes to you, but I don't really mean it.

I'm just really uncomfortable right now and I want to stop.

And so what we do by becoming uncomfortable is make someone else more comfortable.

When they're more comfortable, they'll actually be honest and upfront and engage in, like, you know, feel like, okay, if I say what I really think, it's not going to be a conflict.

Like, they can finally tell you that this thing that you're asking them to do they think is so stupid.

Right, Exactly.

Yeah.

And there's a good reason why they think it's stupid.

And, you know, like, there might be an awful moment in this.

Right?

Yeah, exactly.

Or it's going to inconvenience somebody who they don't want to inconvenience.

Like, it's not going to be good for a customer or one of their team members and they're afraid to say something about it.

Just want to yes you and hope it all goes away.

Yeah.

And as entrepreneurs, we're used to being in control.

We're used to doing it our way, and we can be pretty pushy.

Yeah.

And we're used to hearing yes and thinking it means yes, which is not an unreasonable assumption, but it's not always true.

All right, so we are going to shift again, pivot.

We're going to do a quick, fast fire round.

I'm going to ask you five questions.

If you answered five words or less, and we'll just have a little fun.

How's that?

Five words for each or a five words?

Five.

Five.

So a couple of words for each answer.

Got it.

Perfect.

So the first question, your favorite question, to build instant connection.

I'm gonna come back to that because I know I have one.

Okay, we'll come back, but it is not coming.

All right, so dream dinner guest, living or dead?

Wow.

Okay.

Dream driven together.

You know, probably Alfred Hitchcock.

I'm gonna go with that.

What's harder?

Winning trust or keeping it?

Keeping it.

What's your go to?

Karaoke song?

Skin by Hole.

All right, back to the other question.

Your favorite question.

To build instant connection.

I typically do it in the middle of conversation, and it's something along the lines of, tell me more about how you decided to go there.

I like to hear people's decision processes.

And so it's a variation always on, tell me what led you to that decision or tell me what made you want to do that.

Beautiful.

Getting to that.

Why the motivation.

Right.

What was going on?

Last question.

Best piece of advice you've ever received in five words or less.

People's strengths, other weaknesses.

Oh, isn't that the truth?

Whatever got you here won't get you there.

Holy moly.

So how can people find you, Sheila?

How can our listeners find you and learn about your communication program as well as you work with clients?

So tell us how to get in touch.

You can find me.

My website is Sauce Creates.

It's SOS Creates.

And it has information about me, how to get in touch with me.

It also has information about my course that I teach.

But if you want to go to Maven, Maven's a phenomenal platform, by the way.

It's tends to focus a lot on education, on technology.

So it's got some fabulous technology leaders teaching technology courses.

If you go to maven.com and search my name, Sheila O', Sullivan, or under communications, my course will come up there as well.

Wonderful.

And we'll be sure to put the link right to your Maven site and to SOS Creates as well, right into the show notes.

So that Everybody can find you.

And you do your maven course every so often, right?

I do.

I generally do it six to eight times a year.

Wow, that's awesome.

What is your last bit of wisdom you'd like to share with our listeners today?

This is advice that I was asking people to tell me and I'm going to tell everybody else because I always need to tell it to myself.

It's not too late to do the thing that you think you want to do.

If anyone takes anything away, remember that like the company that, you know we sold, a very successful business that we sold was founded by someone who was in her early 50s.

Well, thank you so much, Sheila for being here.

Thank you for being here.

Thank you for being here.

Thanks for illuminating your wisdom to all of us and to our world.

Listeners, be sure to follow like and share the wisdom of women.

Show on your favorite platform and make sure to infuse more of your wisdom into your business.

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