Scaling With People

Your Board Can Make or Break Your Company's Growth with Keith Dorsey

Gwenevere Crary

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Boards have the power to transform your company's trajectory, but founders often struggle to leverage them effectively. Dr. Keith Dorsey, author of "The Boardroom Journey" and boardroom expert with experience spanning military service, corporate leadership, and academic research, joins Gwyneth Beaver-Crary to decode what truly makes a high-functioning board.

Drawing from his experience serving on five different boards and his doctorate research on corporate governance, Dr. Dorsey dismantles the common founder mindset that views boards as obstacles rather than assets. He outlines the three critical functions boards should serve: management support, advisory service, and governance oversight. The most effective boards operate with a "noses in, fingers out" philosophy—asking thought-provoking questions without micromanaging operations.

Beyond structure and function, this conversation tackles the often-overlooked importance of board composition. Traditional approaches focused on filling seats with familiar faces and fellow CEOs create dangerous echo chambers. Instead, Dr. Dorsey advocates for cognitive diversity and strategic alignment, explaining how to assess both visible skills (the 10% above the iceberg) and underlying competencies (the 90% below). His practical advice on conducting board assessments and facilitating difficult transitions offers founders a roadmap for building boards that evolve alongside their companies.

Perhaps most valuable is Dr. Dorsey's guidance on vulnerability in board interactions. By sharing "the good, bad, and ugly" rather than carefully orchestrating presentations, founders can transform board meetings from obligatory check-ins to powerful strategic sessions that genuinely accelerate growth. Ready to stop dreading your board meetings and start leveraging them as true assets? This episode provides the blueprint you need.

Looking to strengthen your board or find your place in the boardroom? Connect with Dr. Dorsey at boardroomjourney.com or check out his book to continue your boardroom journey.

Speaker 1:

Welcome everyone to today's Scaling with People podcast. I'm Gwyneth Beaver-Crary, your host and founder and CEO to Guide to HR Founders. Here's the truth A board can be your rocket booster or it could be your biggest drag. So how do you build one that actually helps you scale? On this episode of Scaling with People, we're decoding what great looks like in the board room, from aligning on strategies without getting stuck in the weeds to turning board meetings into high-value decision engines. We're laying out the blueprint for a board that works for your growth, not against it. So if you're ready to stop dreading your board meetings and start leveraging them as a true asset, buckle up. This is your founder's guide to a high functioning board, and today I have Keith Dorsey with me to talk about this. So welcome, keith. Tell the audience a little bit about yourself.

Speaker 2:

Thank you, gwynnevere, it's great to be here. I guess I can say with me I am in my third chapter. I tell people often my first chapter was the US Air Force for a number of years, second chapter and thank you for serving. Thank you, thank you. And the second chapter has been corporate America, in which I primarily worked for two large companies over just shy of 30 year period, where I worked for a Fortune 1000 company for almost 17 years and a Fortune 500 company for almost 12 years, in which I ran very, very large sales teams and I was known as a turnaround specialist with those teams and built a career all in the human capital management area. Then I went into what I call semi-retirement in my third chapter.

Speaker 2:

I went into what I call semi-retirement in my third chapter and that's my portfolio career, doing a little bit of this and a little bit of that.

Speaker 2:

I do executive advisory work.

Speaker 2:

I actually serve on five boards myself two private company boards, one municipality, one university and one nonprofit profit.

Speaker 2:

And then I went to work for a global executive search firm for a period there as a managing partner and a practice leader of their CEO and board services, and all throughout this period I was going back to school and I got my doctorate in organizational and change and leadership from the University of Southern California and all my research was around corporate governance and corporate board diversity, corporate board refreshment and that's really the reason why the executive search firm was interested in me.

Speaker 2:

And in addition to those things, I of course wrote my dissertation to be able to get my doctorate, and all the research that I did around helping women get on corporate boards, I ended up writing a book that Wiley just published in May of this year called the Boardroom Journey Congratulations. I launched a business post that called Boardroom Journey where I help boards do the things they need to do differently to line their board members up with their strategy, and I help individuals, executives and government officials find their first corporate board or their next corporate board by doing the things they need to do differently to not only be seen but known and ready.

Speaker 1:

I love that. That's a lot to digest, but you seem like a very big board expert. So as a founder myself, I don't ever like to see that I'm going to grow my business where I would need a board. But for our founders that are listening, who might be getting a board, might already have a board or maybe are starting to think about okay, soon I'm going to likely get one what is the baseline, what's the purpose? I mean, like I'm going to kind of go down to like kindergarten reason for a board here. Let's just start really simple here. What is the purpose of a board and what does good look like as a founder or CEO starts to engage with one?

Speaker 2:

That's a tiny question there, right.

Speaker 1:

It's a tiny, simple question. No big deal, no big deal.

Speaker 2:

You know a corporate board is a fiduciary board to really help businesses grow and really help businesses, dr Eisencross, mitigate the risk and see around the corner as well. And basically I talk to people about what independent directors and board members are supposed to do. They're primarily responsible for three areas, and one I would say is management. That's really helping the CEO. Help find a CEO. If you're already a founder, help that CEO surround his or herself with the right C-suite and so the be that person, that group of people to help around the management side, help them craft their strategy or at least have a group of individuals that you can run your strategy by. So the management side is that Then there's the advisory side, or service side, where this group of board members you can reach out to and get advice about what's around the corner, because this isn't their first rodeo. They have been in your shoes before. They bring a tremendous amount of human capital and experience to the table that founders can benefit from, and they also bring a social capital to the table where they know people. They know people that can help you find more money. They know people and talent that they can help you accomplish your strategy that you're putting in place. They know people that can truly help a founder out, and it could be the difference between making it or not making it.

Speaker 2:

You know, when you think about the possibility of running out of money, you know B-series and so on and so forth, a good board can really help in that scenario. And then so that's the advisory side, and then you have the governance side, or oversight side, and that's really being your eyes and ears and helping you dot your, dot your I's and cross your T's. A saying when it comes to serving on boards is noses in, fingers out. You already have a management team in place to get the job done. As a board member, our job is not to do it and not to not to tell you what to do, but to ask thought provoking questions to help you see around the corners, mitigate risk, disrupt yourself, discover blue oceans, different things like that. So the three areas that I'm talking about in this one segment here is management, advisory and oversight. That's what or would do for an organization that is really trying to get off the ground I, I uh interpret that a little bit.

Speaker 1:

Uh, you know, without using the terms, it's your community, it's your community, it's your mentorship and it's a little bit of your parents pushing you out right, or like the bird analogy, like, yeah, you can fly go.

Speaker 2:

But providing a soft landing for you at times, as well, yeah, exactly, exactly, I love that.

Speaker 1:

So, as a founder might be thinking about the board or maybe they already have one in place. If they're struggling, let's say, let's go for an example. Maybe they're struggling to engage or interact with the board, what are some of the things that they could think about on how to show up differently and engage the board differently that could actually turn a drag a board that's kind of dragging a founder down or what they believe to be dragging them down to a board that is actually their rocket ship and fuel.

Speaker 2:

Yeah, you know that's a great question and there are many different ways I can answer the question. But I want to challenge the founders to get in the right headspace right from the very beginning, because some founders will say last thing I want is a board. Because the board becomes my boss. And the reason why I'm not an employee is because I'm not a good employee. I hate bosses. I set my own thing up so that I'm the an employee is because I'm not a good employee. I hate bosses. I set my own thing up so that I'm the hit honcho.

Speaker 1:

I promise I did not chew up teeth to say that, but I totally agree.

Speaker 2:

And there's no one above me. And now I have this board and I want to tell them what I think they want to hear, so that I can just check that box. Well, that's the wrong mindset, but it's an accurate mindset and what I just said does exist. But if you can think about a board as a catalyst to, if you're able to learn from other people's mistakes and you want to minimize the mistakes that you could possibly make and you want to get from point A to point B quicker, to get from point A to point B quicker and in a way that utilize some contacts that might help you get there in a smoother fashion and in a more profitable way, then if you go into that whole board mindset that way, then you can really begin to make great things happen.

Speaker 2:

You also want to make certain you surround yourselves with the right people. Boards have been around for hundreds of years and, unfortunately, the way that most board members have been found is by asking a question who do you know? And I want to surround myself with people that I like. Who do you know? And I want to?

Speaker 1:

surround myself with people that I like, or maybe a correct way of saying that people who are like me like minded.

Speaker 2:

You are really dead on, and when you do that, you lack the cognitive diversity or diversity of thought, and you may end up with a lot of yes, men and women who will worship you and do exactly what you want.

Speaker 2:

But is that the reason to set up a board? Or would you like to have someone to challenge your thought processes, to question you to the point where you can really think about where you want to go, why you want to go there and obstacles that might get in your way, and eliminate those and come up with three solid strategies and scenarios that actually get to where you want to go, and that's what a good board can actually do. So, in doing so, instead of just surrounding yourself with people that you know that you trust, instead of just surrounding yourself with people that you know that you trust and that will do exactly what you want, you definitely want to find the right people, and most boards will go after executives, former and active executives, and in the history of boards, they typically were other former or active CEOs or other former, former, active CFOs. But even during the pandemic and other areas and just how dynamic the business world is right now, more and more boards are finding the need for different functions yeah. Chros, sales people, marketing Operations yeah.

Speaker 1:

General counsel for compliance purposes. Ohros Marketing.

Speaker 2:

Yeah, general counsel for compliance purposes home these issues that we're dealing with today you could begin to find people that can go deep in their functional expertise area as an executive but can also go a mile wide because of their business acumen. And when founders can surround themselves with people who can complement their executive team and not be like another member of their executive team, you begin to get that diversity of thought in the boardroom. You already have your executives, you already have your industry experts, but to bring in people that think a little differently, ask different questions, you move from that narrow-minded, single-minded thinking because that's the way you've always done it to this more lateral thinking and you can begin to disrupt and be that much more agile and actually end up finding blue oceans from time to time. That really separates you and differentiates you to the point where you become a brand. That happens with bringing the right sort of board members onto your board, but before that, having the right mindset as to what a board might be able to do for you.

Speaker 1:

Yeah, absolutely so. If a founder is backed by investors, they have a board, and now they're hearing this like I don't think I got the right mix of people. What would be like the first or maybe next step for them to take in regards to reassessing the board and finding the right board members to support their growth and scalability?

Speaker 2:

Another great question, and it comes down to bringing expertise, bringing in the right sort of consultant that can come into your board and really bring come with this inquisitive mindset to truly analyze what you have today and really begin to look at the functional expertise that you have on your board today and how much of that functional expertise is relevant For a while. There boards will be filled with people who were giants in the industry as a CEO, you know, 15, 20 years ago, but they can't spell cybersecurity or they can't spell AI. And they are geniuses. They understand strategy, but they may not be as up to date. And so to bring in an expert that can truly analyze the skill sets of every board member you have today and I consider the skill sets, if it was an iceberg, to be the 10% of the iceberg that you see above the surface and then look at the competencies of every single board member you have today, whether that's an executive director, someone who works for your company, or an investor who has a few board seats, or an independent director to be able to look at their competencies, their behavior of traits and the things that they innately bring to your board outside of their functional experience. That's what's the 90% that's underneath the surface of that iceberg. And so begin that person, that consultant, analyze that information. Then they really think about your strategy, so much so that they got an understanding of where you were, where you are and ultimately where you want to go, chart that path and to be there from a management, advisory and oversight standpoint for you and to support your management team, your C-suite, the best they possibly can Do.

Speaker 2:

You have a redundancy of skill sets and competencies when it comes to your strategy and where do you have gaps? And then to begin to look for board members that can fill those gaps, either by adding more board positions or replacing someone where they're really just redundant and not adding able to add value, based on where you're going. They may have been perfect for you at the very beginning, but where you're going do they have the right skill sets and competencies? And that's where they should start by bringing in experts that can do that. And then testing and analyzing your board members, having them do assessments of themselves, self-assessments, peer-to-peer assessments and board evaluations. How do they think the board is doing?

Speaker 1:

Interesting. I love that. And you said you know sometimes the board member is there at the right time. But now you know for you where you've gotten to but it's not necessarily the right board member for your future. I say that all the time to founders about their employees. Right, it's like it's such a hard thing to manage, to say to someone to manage them out when they've worked so hard for you and yet you know that you don't see that potential for them to be able to execute at the next level where you're going in your business, and I never thought about it from a board member perspective that it could be the same.

Speaker 2:

It really is, and I think about it from a C-suite standpoint, with the executive team as well as the board and the saying there you said it, what got you here may not get you there.

Speaker 1:

Yeah, yeah, and I think it's just again. It's one of those things where, as a founder, hopefully they're sitting in the mind space of openness and understanding. No one knows everything, no one is perfect, and that we can always think about things differently and grow and learn from each other's past experiences and failures and successes. Right, and to be to go into that board meeting with a bit more of an open mindness, if they're not already doing that, to hear that from their board, yes, yes.

Speaker 2:

I have worked with some boards that spend so much time the C-suite of that company will spend so much time talking about the upcoming board meeting and what they are allowed to say to the board and what they're not allowed to say to the board, and I equate that as a board member to garbage in, garbage out.

Speaker 2:

We're not here to punish you, we're not here to show you how smart we are, we're here to help and if you're giving us garbage information, you want to get garbage out and it was just a waste of time.

Speaker 2:

You come with that open mindset and open kimono sort of mindset and I'm going to share the good, bad and the ugly and I'm going to use the human and social capital that my board brings to the table to make certain that we dot our I's and cross our T's and that we minimize our risk and that we truly field test in the boardroom or strategy with these unique minds that aren't monolithic and hopefully challenge our thought processes to the point where we walk out of that board meeting feeling more confident about the things we're doing right and feeling a little bit stressed about some of the things we're doing wrong.

Speaker 2:

Feeling a little bit stressed about some of the things we're doing wrong, but we're going to go back to the laboratory and tweak some things to get it right, without investing too much time and money into something that wasn't going to work right Because we were vulnerable and we utilized the beautiful minds hopefully, if you did it right that are in the room. This can be a catalyst for success if you're vulnerable enough to deliver the good, bad and the ugly.

Speaker 1:

Yeah, yeah, for sure. Well, I feel like we could probably talk about boards all day long. But wrapping up here, is there any last thought or tip or trick or mindset you'd like to share with our audience today?

Speaker 2:

I would say, when it comes to thinking about your board, to really just slow down enough to say, okay, who's here? Why are they here? Do they want to be here and are they adding value, want to be here and are they adding value? And sometimes, because most people bring on their friends as a board member, it's hard to have those tough conversations, it's hard to get rid of a friend and by bringing in an expert that can, a third party that can have conversations with every board member and go through assessments with the board members and be able to collect data and, based on the data, help you make decisions as to where you need to go. Next, it's the third party that's telling your friend that, thank you, we wouldn't be where we are now if it wasn't for you. Here's where we're hitting and, based on where we're hitting, how do you believe you will add value?

Speaker 2:

And when that third party begins to have those sort of conversations with your friends who happen to be on your boards, oftentimes they will disengage themselves. This has been a pleasure and I'm so happy to help you get to here, but you really do need someone that brings X, y and Z to the table, and that's not me, and now you're not the bad person in this scenario. So that would be my advice, and because many boards hold on to the wrong board members too long, because they're afraid of upsetting something that's much more dear to them and that's their lifelong friend information and I feel like, if you want to dive into it a bit more, you can grab Keith's book, get a hold of him.

Speaker 1:

We'll put links into our description here of our podcast, but any other ways to get a hold of you, keith, or that you want to share with the audience.

Speaker 2:

Well, you can definitely find me on my website, boardroomjourneycom.

Speaker 1:

Well, that's easy.

Speaker 2:

On LinkedIn. You have. You have. You could find me under Dr Keith D Dorsey and you can read a lot of my articles in LinkedIn in the feature section and in my post. And you can also find my book from the website Boardroom Journey. You can click on the tab called Get the Book and you'll find many different ways you can read the boardroom. Buy and read the boardroom journey.

Speaker 1:

Great, awesome. Thanks so much for being on this podcast with us today, keith. I really appreciate it For the audience. I hope you got some tidbits on how to grow, manage, work with, improve, enhance your board as you continue to grow and scale your business. So thanks for joining us today and we'll see you on our next podcast. Have a great one.

Speaker 2:

Thank you, Guinevere.

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