The Secrets To Landing Your Dream Board Seat With Debra Boggs
Tune in to this episode of the Intentional Leader Podcast as host Sean Olson welcomes Debra Boggs, founder of D&S Executive Career Management. From first-generation college student to boardroom expert, Debra shares her inspiring journey and insights into becoming "board ready." Discover the qualifications needed for senior leaders seeking board roles, explore the diverse motivations driving individuals towards these positions, and gain valuable advice on navigating CEO-board member relationships. This episode delves into the challenges and strategies of scaling businesses, offering practical takeaways for entrepreneurs looking to achieve growth and efficiency. Don't miss this captivating conversation as Sean and Debra unpack the secrets of successful leadership.
Important Links:
https://www.dscareermanagement.com/
https://www.linkedin.com/in/debraboggs/
debrab@dscareermanagement.com
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The Secrets To Landing Your Dream Board Seat With Debra Boggs
Welcome to Episode 29 of the show. This is the show where you read the real stories of normal people like you who have become extraordinary leaders. You'll learn some valuable lessons from their lives, lessons you can apply to become the best leader you were created to be. When you become an intentional leader, lives are changed. Thank you for joining us.
It is my privilege to announce our guest is Debra Boggs. Debra is the Founder and CEO of D&S Executive Career Management. She is an expert in executive job search and board candidate best practices. I'm excited to have her on because this board piece is a common question for us. Debra, welcome to the show.
Thank you so much for having me. I'm looking forward to it.
My pleasure. Thank you for your time. I know you're familiar with our show a little bit. You've read a few episodes. We begin every episode learning about your career path and how you've moved on through and to get to this point of being a founder and taking that big jump to be the entrepreneur and having your own business. Tell us about your journey and the leadership lessons along the way.
I’d be happy to. As a lot of people, maybe a lot of your readers, I didn't know what I wanted to do when I meandered through several things early. It took me a while to nail down where my passion was. I was a first-generation college student and first white-collar worker professional in my family. I didn't know what the opportunities were and what the options were. I finished college and meandered through a few jobs.
I worked at a marketing company, in higher ed, did fundraising and alumni relations. I liked a lot of things, but then I got what I thought was my dream job. I got what I thought was going to be the thing that was perfect for me and my skills. That was to lead career services for university. I loved it. I thought, “I am here. I have made it. This is the absolute top of where I could be.” I learned during that time that what I loved and what gave me a lot of energy was working with candidates because that university worked with a lot of returning alumni and not necessarily all just students.
I loved working with the returning alumni on their resumes, their job search strategy and getting them confident about the search. Giving them the confidence and the tools they needed to go for stretch rolls and get more than they thought they could. That gave me a lot of energy and I kept doing it on the side. When that role ended, I was vice president of business development for an online training company. That was a great job, but I was getting a lot of creative energy from working with job seekers and their resumes. I started as a freelance side gig, side hustle. There's a much longer story, but it snowballed and took over my life and here we are.
I understand that and that's happening a lot with people where the side hustle becomes the hustle. That's our story here. This is my side hustle for a few years with Renegades Professional Coaching. Now, it's been the hustle for many years. Talk a little bit about what you're doing with your company. I know it just was a side hustle, a gig, but what was that point in time where you're like, “It's time. I'm going to flip that switch and go from the side hustle to the hustle?”
I started this side hustle many years ago. I quickly got this book of business. I had referrals and things were coming in. I had young kids at the time. My husband's a stay-at-home dad, thank goodness I don't think I could have done the side hustle and the full-time job at the same time. I had a 1 and 4-year-old at the time when I first started this.
I was focused on doing quality work and delivering what I said I was going to do. I didn't realize, especially in the freelance world, that those were unique traits. I got a great book of business and it got to the point where I thought I wasn't making full-time income yet. A lot of people with a side hustle wait until it replaces their full-time income, but it can't. I thought, “What can this be if I could focus full-time on it?”
If I could focus my passion in the space and my energy in the marketing to grow it. We decided to rip the band-aid off and go for it. A little bit before we were ready, but it was one of those things where we had solid work, but it didn't replace my full-time income at that point, but we did it. I say we, because my husband was helpful in the early days. I replaced him during COVID in the business but it was great. It was one of those leaps of faith and it delivered.
I now think about all the other times in my business I've had to take that leap of faith before I was ready. We were able to deliver on, which was the catalyst for getting to that next level. Fast forward seven years in the business, we have an international reputation in the board services space. We have partnerships with companies and organizations like the New York Stock Exchange.
I have a team nationwide. There are about twelve of us who all focus on working with senior leaders through their executive job search or their board search. What started as an online resume writing as a freelancer has morphed into working with VP and board-level candidates to help them prepare for and navigate their high-level searches. That's been so rewarding. It’s a group of people who love their work and love working with the candidates.
Become Board-Ready
It's making an impact on them. Thank you for sharing that. The big piece for us, we hear about boards all the time and board members. I love the phrase you had when we initially talked about helping people become board-ready. Dive into that a little bit. What does it mean to be board-ready?
It's something that comes up all the time where senior leaders will have a C-level role typically. A lot of CEOs or CFOs will think about, “Could I get a board role? What does that look like? What does that process look like?” Getting board ready is an important piece of that and it's a couple of things. It's having the table stakes, which is the senior level leadership.
Getting "board ready" is important before getting a board seat.
You've been at the table and you understand what that looks like. You usually have at least fifteen years of leadership experience. You've got to have some time in the game, too. An area of either deep functional expertise or deep industry expertise. You may have to go real deep in one industry or deep in a function. Either of those things are helpful. The other piece that you need then is an understanding of corporate governance.
That's a lot of the pieces that sometimes people are missing and they get into the room. They realize, “There's a lot of pieces around governance that would help with the interview process for board seats to help with understanding their role if they get a seat, what that looks like.” There are a lot of programs around preparing people for board seats around board governance.
There's a lot of different options. Private Director's Association is one that's low cost. NACD is the gold standard that some people do. It's not necessarily that you have to have a certification because I get that question a lot. It's around have you done some professional development to understand the vocabulary and purpose of board governance?
That's very important. I'm glad you mentioned some of those opportunities that are there to establish that corporate governance piece because I'm sure that's the one thing that most people are missing versus the deep technical knowledge or the experience at the corporate level or higher levels. It's interesting to me, what do you see as you're working with these individuals who want to be on boards? What do you see that's driving them to want to join a board?
There are a couple of things and it depends on the person. There are a couple of different ways that clients come to us and say, “I'm looking for board work.” It can be that they are preparing for retirement in the next 5 to 10 years and want to soft launch into retirement. They want to get a couple of board seats so they're not completely shutting off their career. People are at retirement now and thinking, “I don't want to lose my network. I want to use my brain. I want to still help companies do great work, but I want to also have a lot more flexibility.”
They'll look at board work as a way to stay relevant and active in their industry or their function without necessarily having to take on that full-time responsibility. Some people want it for income. Corporate board seats that are paid opportunities can be pretty lucrative. Some people do want that income, which is great. Honestly, some of it is hard.
I'm sure a lot of your readers may feel this way. I don't know about you, but the thought of retirement is scarier to me than the thought of working for the rest of my life. I think that is the case for a lot of our clients, too and a lot of senior leaders and executives. You've built this amazing career, a high achiever, and always going for the next thing. The thought of fading off onto the golf course is terrifying. I know it is for me. That’s a lot of the driver for people as well.
That makes sense. I'm noticing something you didn't say. Are you getting much of like those mid-career people who've got that 15 to 20 years? They may be 45 to 50 years old. They've got fifteen years of life left, they're not thinking of retirement yet but they've got some rich experience. They want to give through their service to a board as well as to learn in their service to a board. Are you finding much of that mid-career? If so, where are they coming from? If not, why not?
I'm so glad you brought it up because, yes, we are seeing that mid-career. Mid-led leadership careers still have to have that deep functional or industry expertise. I say to them that if you're not necessarily board-ready for getting a seat on a paid board opportunity, then in that mid-career space a great opportunity is advisory boards. Working with an earlier stage company or a smaller company that may not have a formal board but that needs some expertise in some area.
Board Seat: In that mid-career space, a great opportunity is advisory boards.
There's less process around how to get on an advisory board. There's less compensation. It's usually more of an equity situation if it's paid at all. At least, it starts giving you that experience. You're able to give back. You're able to use your expertise. You're growing your network, and getting some of those advisory seats is a great way to get board-ready to get the paid seats. Sometimes, if you don't necessarily hit all the perfect markers for a board candidate in the paid seat space, advisory board seats are much more low-hanging fruit for people in that mid-career space.
I like that. It's like the whole corporate ladder. You’ve got to serve your time a little bit, take the advisory positions that may or may not pay, but get the experience so you can get in something else that's much more lucrative and beneficial to a larger corp. I like that a lot. When we are coaching leaders, we coach a lot of officers and organizations. They have a board that they report to.
It's very common for us to have rich and honestly difficult conversations because oftentimes the relationship between the officers, the CEO and the board is not that great. I want you to put on the hat for a second. We're going to flip these hats but for now, let's put on the hat of the CEO. They're struggling with their board. What tips would you give them to navigate that relationship more effectively?
This can be so hard. I know it's an issue for a lot of CEOs wondering if they're reporting to the board, either. They're new in the role or maybe the board leadership has changed and they're not meshing. There are a couple of things that are important to think about, especially in a formal board setting. Not the advisory board setting.
The board has fiduciary responsibility for the company. They have a stake in the game. Remembering everyone's motivations are helpful and remembering that the board is there for the success and the long-term sustainability of the company. The CEO should be, too, but sometimes those competing priorities of now versus long-term can be combative.
Remembering the motivations of the board in general. I see a lot of CEOs either talk about the board as more adversarial or, “I'll have to take this to the board or I'll have to present to the board.” I think more thinking about your board as your partners and the success of the business and remembering that they're there to help build the business as well.
Calling on them more often and maybe not showing up in the quarterly board meetings. Calling your board chair, reaching out for advice, reaching out for, “This is going on. How would you handle it or I wanted to keep you apprised of such and such.” Across all the board members, help give those little touch points that instill trust in your work rather than the giant board presentation that you give quarterly. Those touch points of trust and relationship building are incredibly crucial to a strong board working relationship.
I like that. The phrase we use all the time is that there is no trust outside of relationship. We have to go after those, encourage those, and develop for our benefit. Let's flip hats for a moment. Let's say you're a board chair, for instance, who's working directly with the CEO. The relationship's not going well. What tips would you have for that board member to work more effectively with the CEO?
At the board member level, you have more resources at your disposal. You can suggest more options. I would say if there's an issue with the CEO and the board member and maybe it's the whole board or a couple of members on the board. Maybe there's some relationship or some personality conflicts, I do think it's important to bring in a third party and have a board come in or do a retreat or get another perspective in the room because sometimes, it can get personal, especially if there are personality conflicts. If you get a third party in the room to mediate that, set clear expectations, and set goals and have everybody on the same page. Sometimes, having somebody else come in helps relieve some of the tensions.
Board Seat: Sometimes, outside sources coming in help relieve some of the tensions.
What's interesting about that, sometimes the most brilliant things are like incredibly simple. If you think about the CEO and the board members used to be in leadership. They know what the corporate side of it is. When we are developing our leadership team, the officers, or the VPs, we will usually bring people in to lead us through leadership stuff, difficult conversations and productive conflict.
Outside Sources
It seems like one of the things we forget, with maybe as important a leadership team, is the board and the CEO. Now that plays out. I like that concept of basically treating the same way. Our office team, we're going to develop one another. We're going to have the relationships. We're going to bring in outside sources. The same thing with the board team working with those officers.
I'm a huge fan of outside sources. Even in a business our size, we're still a small business, but I spend a lot of time and money on professional development and coaching for our team and myself. That was one of the things that leveled my business up. It was seeking out an executive leadership coach for myself of saying, “My team isn't going to tell me what I suck at. What are my blind spots? Where can I get out of my own way? Where can I level up?”
The more you do that, the more you still need it. Once you get into the board and CEO level, you're so bogged down in the day to day-to-day pressures and you forget some of those simple things of clear communication and all the things we've learned. They can get forgotten and I don't think that coaching is stuck in one level of your career. Bringing in someone benefits every level.
I am a coach. Obviously I believe in that, but at the same time, coaches need coaches because we're still developing things in different ways. Let's transition for a second to your company as you're talking about that. I know you said your side gig has now been your full-time gig. It was you and your husband years ago, initially. The same with my wife and I. It was just us at the beginning. You have twelve people around the country. You've expanded your services. You've used some coaches and other advisors to help you on the way.
Coaches need coaches because we're still developing things in different ways.
We have a lot of entrepreneurs and solopreneurs that read this. A lot of solopreneurs don't necessarily want to be a solopreneur. They don't know what to do to take the next steps to hire that first person and scale the business. Share with us for a minute that first time you're like, “We got to bring somebody else.” How did you know it was time? What did you want them to do? Talk to us about that.
I have a great story about this because same, I was a solopreneur. I didn't necessarily want to be a solopreneur. I didn't set up to start a business. When you start a business, I'm sure a lot of the solopreneurs reading, all of your readers are thinking, “You have to do all of the things.” I was a great resume writer. I love working with clients. I'm not a numbers person. I didn't like doing the accounting.
We built a business so quickly and didn't anticipate building a business. There's a lot of like backward of rework we had to do to clean things, get it organized, and to get systems. Fast forward about two years into the journey, work is going well, but I hit a wall. I couldn't grow any further without bringing on more people. I got to the point where I was like, “I could bring on more resume writers.” That would immediately add to revenue, but we needed structure and I needed operations.
I thought, “If I brought operations, I can get organized and then be able to scale more efficiently.” I went back and forth on this and we decided on operations. I would say to any business owner that the first hire being operations, was a game-changer for us. It was huge. I was able then to focus on the work that I do best and let go of a lot of the things that I am not great at right. In fact, a woman who leads our operations would probably give you a whole list of things I am not amazing at.
I got lucky because it was, I would say, probably early COVID. I got to this wall point where I thought, “ I'm doing okay, but what could we be if I could scale? How do I scale? I can't afford to bring someone on until I scale, but I can't scale until I bring someone on.” Chicken and an egg. I had a client who had a corporate leadership career, and then built and sold her business. It was a local grocery store like specialty grocer and sold that business.
I met her because she came to me because she was starting to look for her next thing. She was moving across the country. When she came to me as a client, she said, “I don't necessarily have to work, but I want to work. I want to stay involved. I want to work from home,” before work from home was everywhere. She's like, “I don't know what I want. I want to stay busy, but I don't necessarily need all of the all of the things I always had in my last.”
When I had this opportunity come up, I thought, I need an adult in the room to help guide me because I'm not naturally a business person. I reached out to her and will never forget because I emailed her. She had been a client months prior. It had been a while, but I remembered her and her skills. I sent her an email.
I said, “I don't know if you're still looking for work, but I need someone to help me build up my operations. I have a job. I don't know what the job is, what it pays, or how many hours it's going to be, but do you want to come do this thing?” Her response was, “HELL YES.” I thought, “That's the energy I need. I need that energy. We'll figure the rest out.” She's still with me and it's been great. We've grown together and scaled the business. It's been amazing.
Thanks for sharing that story. Do you know what I like towards the end of that? We've been down the same path. Many people hesitate to pull the trigger because they think they have to have it well articulated. Full job description, what it's going to be? How many hours it's going to be? That's not the reality of small business. The reality of small businesses, we get constantly agile and pivoting where it's going to come. When we hired our first full-time person, we had a lot of contractors and we still have a lot of contractors.
When we hired our first full-time employee, we talked to him the same thing as you, about the job description and what it could be. I was literally like, “I don't know.” When I hired my EA, we're like, "We're okay. We're looking to probably five hours a week and we'll start with this, but I don't know." It grows with them. I think it enhances the relationship because it allows them to see what they can do and say, say, "Can I?" It allows us to see more opportunities that are there to say, "Will you?" It forms a great relationship because this is all about communication.
That's so true. That's how it's gone through. She hopped in and she was not from our industry. She had never done a remote role. She's on the other side of the country and we built it together. It was fine, but you have to be agile, okay with change and constantly iterating. I think about the business where it was then and where we are now. We joke that we're at D&S 3.0. We've gone through major iterations of the business over the years.
Odd question for you because you were in a career search resume writing. You understand all that. Was it more difficult to hire people because you're like, “I know how this thing works?”
No, because I don't do a ton of like, “Here's a job, description and come apply,” and we go through the whole process. I am more about always thinking about recruiting and who's next on our team. I'm active in our industry or professional development organizations. I'm active in going to conferences and meeting the resume writers and the coaches in our industry who are doing the best work. That way, when we have a spot open, I already have an idea of who I want to reach out to. If that makes sense, I do more of an active recruiting model than a job opening model.
It does, and that's the way a small business. We're in the same boat. I’m always looking ahead and by the way, for readers, part of the reason she was able to look ahead, think ahead, and go to those conferences is because she brought in the ops person. Only she could do right and we've done the same thing. In 2024, we knew that in Q1 we were going to bring in 4 or 5 new contract coaches. I knew where I was going before I started developing relationships and talking to people. Even talking to coaches that had other contract coaches and who do you have that's looking for more work and things like that, even developing your own people. All of our employees started out as contractors.
Most of ours did, too. In our industry, that's common. When you think of it you have a full-time role open who works well with you, who's behind your mission, who does great and work for the clients. It's easy to know who's coming next.
It's an important piece because there are a lot of people who want to make a change. They're afraid to become a contractor or a subcontractor for 3 or 4 companies at once to make ends meet. They don't want to do that. They want “the security” of a full-time job. There are a ton of small businesses that use the contractor route to fill their employees. It's an avenue.
The contractor route was a big deal for me when I took the leap into doing this full-time. I did have a couple of contract relationships where I was a subcontractor for other companies like ours because it gave me enough regular income to know that I could build the company and not eat cat food. Although, I don't have a cat. I've been told cat food is more expensive.
It gave me a little bit more reliability in my income. Sometimes, people don't want to do that because they want to do their own thing or if you're going to if you're going to jump into entrepreneurship. You have to build the whole plane by yourself. I feel like you can partner and that's where we've been successful is partnering with other organizations even if they seem like competitors on paper. You don't have to do everything alone.
Leading More Effectively
I use the phrase strategic alliances. Strategic alliances in the sense that there's a benefit to them. There's a benefit to us and those benefits aren't the same thing. It's mutually beneficial, so it's worth having that strategic alliance and developing things because we never get anywhere by ourselves. That's awesome. Debra, it's been great talking to you. We finish every episode with the same question, so I want to ask you that question. What is something our readers can do intentionally now to lead more effectively?
When we talk about leading more effectively in my space, I would say this of working with people that are building their careers even at the highest levels. We work with CEOs of large companies who, if they leave their job for whatever reason, they'll come to us and say they don't know what they want next. Having a clear picture of where you're headed helps you make all those other decisions.
Whether it's in your company, starting a job search, or thinking about moving into board service, you want to lead through board service. It's being clear about where you do your best work, who you're uniquely equipped to serve and what you want your career or company to look like. If you're clear about those things, then all of the decisions that come after that are easy. If you're not intentionally managing your career or your business or the direction of your board search or all of these things, then it's just haphazard and it’s happening to you instead of you driving intentionally into the direction you want to go.
That's the definition of intention. Taking it on as we go. Thank you for being a guest, Debra. For our readers, you'll find links and how you can reach out to her and her company, D&S Executive Career Management. If you have any of those issues you want to tap into, I'd encourage you to reach out to her. Thank you very much. I pray that your business keeps on growing and having an impact.
Thank you so much.
Important Links
Debra Boggs - LinkedIn
