Advice From A Seasoned Mentor With David Roberson

Oct 19, 2022

David Roberson of RoseRyan shares insights about advantages of mentorship and the mindset you should have as a mentee to objectively take feedback and leverage your mentor's knowledge and experience.
HITC Dave Roberson | Mentorship




When I was a sprouting employee at IBM, I got assigned a mentor. The cool thing about her was that she wanted to be a mentor, which I have found over the years makes a big difference in the experience for the mentor and mentee. She was phenomenal. She changed the whole trajectory of my career in the direction in which I went and how I showed up at work.

As a matter of fact, I don’t even know if we would be here now if it hadn’t been for her. Our guest is not only a serial and seasoned corporate executive but also took over as the CEO of RoseRyan, a financial accounting advisory firm based in Silicon Valley. He is also a mentor to dozens of people. RoseRyan, his company, has grown a lot over the years.

As much as I want to spend our time talking about what they do because we can all benefit from having a little bit more financial acumen, I want to spend our time with Dave Roberson talking about how he has mentored people over the years. What he has seen and what are some of those pitfalls he’s seen with founders and entrepreneurs as they’ve started their businesses and how they’ve grown and become better.

Dave Roberson, welcome to the show. I want to start off by thanking you, on behalf of all the people you have helped over the years and as a fellow mentee and now mentor, for the time you have given to the people you’ve supported. It’s a huge gift you’ve given all of us. Thank you.

Thank you. It’s a pleasure to join you. People sometimes ask me, “What’s in it for you with mentoring?” I get as much or more as the mentees because I learned from each of them. One of the secrets to me of enjoying being a mentor is being open-minded to what you can learn coming in the other direction. I probably learned more than I’ve shared in some ways. This is a topic I have a lot of passion about. I’m looking forward to the conversation.

Thank you so much. Tell us a little bit about you and the trajectory of your career. What are you doing with RoseRyan?

I spent a long time at one company. I was with Hitachi Data Systems for more than twenty years, and I was fortunate there. I had three careers in one company. I started as a lawyer, shifted to finance, and then shifted to running the company. One of the reasons was that I was given a chance and guidance along the way to take on roles that I wasn’t all that qualified for. The first one I was, but I didn’t have any financial training when I became a finance exec for that company. I’d never been a general manager when I became the COO of that company. One of the things I’ve always realized is that I need to pay it forward because of all the chances I was given early in my career.

Measurement doesn't equal punishment. Click To Tweet

I left there, went to HP, and ran storage for them for about 4 or 5 years, and then I got tired of the corporate game. I’d been at it for a long time. I’d traveled heavily. I wanted a little different way of working, so I decided, “I’ll shift to doing advising.” I had already been serving on board. I continued with that pastime. I stepped up my mentoring then because I had time to do it. That’s where I built most of what I’ve done since. I enjoyed that for 6, 7, and 8 years and then felt a little bit of an itch come back like maybe I can do something in a work environment. I went to RoseRyan to be one of their consultants. Within twelve months, I ended up being the CEO. That was never my intention. Kathy, the owner and founder, and I thought that was the best use of my talent.

She stayed as the chair and we worked like two in a box, so we shared every decision. That’s been good because I’ve never shared authority like that before. Another big learning for me is I don’t have to have all the answers. In fact, she had many answers I didn’t even know the questions to. Again, I learned a lot. We sold our company to ZRG Partners to go on to the next chapter. We were looking for how to grow the business and wanted a bigger platform than just RoseRyan. We were going to build one and then ZRG came along and said, “Join our platform. We’ve already built one. You can grow with us.” That’s how we ended up there.

Congratulations. That’s great. 

Thank you. We’re still in the early stages of it, but I’m pleased with what happened there. A lot of it had to do with culture. We’d maybe come back to that later if you want to talk about that.

HITC Dave Roberson | Mentorship

Mentorship: Being a mentor is being open-minded to what you can learn coming in the other direction. You can learn more than what you’ve shared in some ways.


I’d love to talk about it now. I’m looking at your website, the longevity of employees, and how people talk about it. The founder created that culture.

She created it. I won’t take credit for the creation of it. They had a pivot several years ago. Kathy realized she needed a strong culture to take the company to the next level. She invested several years of time, a lot of people’s time, input, listening, and so on to build a strong culture. It’s funny, she and I were talking about it. Our culture, in essence, has created a lot of value for the company because we’re consultants. We can go from one client to the next. Clients can hire us or somebody else. What sets us apart, we think, is the way we work together, support each other, and are accountable to each other, which you don’t always find in professional services firms.

Some of our competition is that every consultant is out there on their own, making their own way. We don’t think that’s the best way. It’s better to have a collaborative team approach with accountability and still strive to delight the client every day. Kathy built the, “Let’s work as a team.” I probably shifted the culture a little bit more to, “How are we going to grow the business?” I come from growth is everything. You have to grow or you’re going backwards both personally and in the business. I look at both sides. I brought more of that, how do we grow and more of a metric-driven culture. Every week, I meet on every key metric in my business because I want to know how we’re doing.

We’re all accountants. We know the numbers, but it was a little different way of looking at where we were going and where we were. I communicate that broadly with the organization so every employee knows once a month how we are doing, how we did last month, how much revenue, how’s our pipeline, and what new clients did we sign up for. I’m a deep believer in transparency as part of that getting to that next level. Kathy built and established it, and then I put my tweak on it to add a growth element in a more metric-driven element, which sometimes people are like, “That’s not personal.” It’s not personal in one sense, but it’s personal in another sense because we all have an impact on what we’re looking at.

If you are in the fear zone, you're not being creative. Click To Tweet

Employees benefit a lot from both the transparency and knowing the health of the business because then they know the impact they can have. They’re more on the lookout for ways to reduce costs and increase profitability. They’re looking for ways to bring in more revenue. They’re looking for those efficiencies where if you don’t give them that transparency, how will they ever know that?

The second thing also is that people benefit from having a goal. This is something that’s overlooked by founders and entrepreneurs. I hear this a lot, and maybe you’ve heard this in your journey too, where they’ll say, “I don’t want to corporatize things.” Both you and I came from a corporate background so we know what that means. It isn’t pleasant. It’s politics and all kinds of crummy things. The good part about corporatizing things in setting goals is that then people have a clear idea of which direction we’re all headed. That’s where metrics can be wonderful and helpful, too.

We work with our clients on metrics all the time. One of the conversations I have a lot of pleasure about is, “What are your metrics? How do people know if they’re succeeding in your company?” If they don’t know, then they don’t know. How are you going to harness that energy to move a company together to a new place or to the place you want to go unless people understand what their piece in that pie is and what the expectations are? Measurement doesn’t equal punishment. A lot of people think, “You’re going to measure me and you’re going to punish me.” It’s the opposite. We’re going to measure you so you can do better. That’s a different mindset. People in the corporate environment can’t miss a number.

You can’t have a bad day or everybody’s all over you all like, “You’re a failure. You’re this or that.” We do this to learn, grow, and change. Kathy and I say we like failing. They’re like, “You guys are crazy.” “We like a failure because it means we’re trying new things and we’re learning.” The key is, what do you do with the failure? You fire the person and kick them out. That tells everybody, “Don’t try because if you fail, you’re out,” or do you say, “What can we learn from this?” Let’s not talk about who’s at fault because that’s where a lot of people go. It is who caused this problem.

HITC Dave Roberson | Mentorship

Mentorship: You won’t be able to move a company together to a new place or to the place you want to go unless people understand what their piece in that pie is and what the expectations are.


We probably know who caused it, but that’s not the issue. Are we going to learn, grow, and change or make the same mistake again? I look at failure as a real positive thing. Some failures are too big and the person has to go fraud, dishonesty, and those things. That’s not the kind of failure I’m talking about. Let’s say, “We take on a new business challenge. Everybody’s aligned. Let’s go do it.” We don’t reach the number. That’s a failure in some way, but why didn’t we reach the number? What did we learn? How are we going to do it differently now?

We’re applying learnings to our business now from our failures before. We’re not going to get it right this time either, but we’ll be more right than we would have been having we not learned. We’re going to learn some new things. It’s a virtuous cycle of how I look at it. People are willing to try. The whole point is the willingness to try something new without fear of losing your role, being punished, or somehow losing favor. You almost have to celebrate the failures in a funny way.

If you get angry and flip out about it, that creates an accidental culture of fear. I don’t think that anyone thrives in an environment where they are fearful. That certainly doesn’t spark innovation. Fear does not usually result in innovation. If it does, it’s short-term.

I would suggest it never does. If you’re in the fear zone, you’re not creative. You’re worried about things. You’re not thinking about what could happen.

When a mentee is unwilling to listen, they think they know all the answers. Click To Tweet

With all the people you have mentored, do you hear patterns where you sit down with a founder or an entrepreneur early in their journey that’s in the startup phase, whether it’s in your role as a mentor or a consultant at RoseRyan? What are some of those things you hear in the early days where you know in your heart like, “That’s going to be a problem later?”

There are 2 or 3 things. One is an unwillingness to listen. I was amazed. Some people I’ve had to walk away from or they said, “I don’t want to talk to you.” I’m like, “Okay. We’re not meant for each other. That’s okay.” They think they know all the answers. What do I look for? Curiosity. Curiosity, to me, implies humility because someone that’s curious knows they don’t know everything. That combination is powerful, but somebody that’s either not curious or afraid of being wrong is dangerous for a CEO because then you’re limiting the company to that person’s knowledge and understanding. I used to talk about the DNA mix. I don’t know if that’s the right terminology anymore, but a mixture of people, thoughts, ideas, and background.

You, as the CEO, need to tap into all that DNA to make a better decision. When I see somebody not willing to do that, it’s a huge red flag for me because they will not succeed over time. Their team won’t be stronger over time because it’s limited to what’s in their head. That’s one red flag. A real positive one I see, and those are the flip side of that, is somebody that’s taking time to listen that takes on what they hear. It’s one thing to listen and do nothing. It’s another thing to listen and change. To me, that’s a powerful leader. Kathy is a great example of this. She and I can be totally honest with each other about what each of us is doing.

It’s okay because we’re both willing to listen. I gave her some feedback. I said, “Somebody said we were defensive. They were talking about the two of us.” We looked at each other like, “How could they think that?” It’s like, “No, they said it, so they think it. They could be wrong, but what are we going to learn by this?” That’s an example of being open to what’s out there. It may not make you happy all the time with what you hear, but having that ear to the ground, if people don’t listen, they’re never going to hear it. The other thing I look for is where they engage. I like engaging all levels of the company because if you’re only talking to your leadership team, you’re not getting all the truth.

HITC Dave Roberson | Mentorship

Mentorship: We are applying learnings from our failures. We’re not going to get it right this time either, but we’ll be more right than we would have been.


I’m not saying people are lying, but there’s a truth that comes 1 or 2 layers down into the organization. If you talk about empowering somebody, try talking to that first-line person as the CEO. The first thing is they go, “I’m in trouble.” I’m like, “No, you’re not in trouble. I want to know what you think.” I had a great example of this when I was leading a team for RoseRyan.

This was before I joined the company because I was working on a project with them, so I was one of the people on the team. We were in a meeting and trying to decide whether to hire somebody to join that team. Everyone on the team interviewed the person. I had them all sitting there. I said, “What do you think?” One by one, we went around the room, and I got their opinion. Somebody came up on the afternoon of the meeting and said, “Dave, in my entire career, nobody has ever asked my opinion.”

I started mentoring her. She’s moved on and grown tremendously since that time. Not because of me, but because she suddenly felt like she had a voice. That was a powerful lesson for me. Other people working for me have voices they’ve never used before that they’re afraid to use or no one’s ever asked. One of the things I try to do in meetings is to make sure I get all the voices. Sometimes people are like, “Why are you doing that?” I was like, “I want to know what everyone has to say.”

One thing I need to do sometimes is shut up and listen because I have this tendency to, “Here’s where we’re going to go. Let’s go out.” Another example was one of my team said to me, “Dave, we want you to come to a meeting and not say a word for an hour. I want you to just listen to us for one hour because you never get to the end of what we want to tell you. You always have your answer before we get to the end.”

Curiosity implies humility because someone curious knows they don't know everything. Click To Tweet

I didn’t like that. I’m like, “This isn’t going to be a fun meeting. They’re just going to yell at me for an hour.” It turns out they didn’t want to yell at me for an hour. They had some powerful things they wanted to tell me and I thought, “I love this team.” They got the guts to say to me, “Shut up for an hour so we can talk to you.” I took that as a good thing. I didn’t like it and didn’t want to hear it. I went into that meeting, but I came out of the meeting empowered. If your mentee is not open-minded, forget about it. You’re wasting your time.

There needs to be a goal as well with the mentoring relationship. It’s got to be an outcome that you’re both striving toward on some level. I came from Corporate America as well. I worked for Hewlett Packard for the Colorado Memory Systems division, and then I went to IBM for twelve years. I was in Corporate America for a long time as well. How has the journey been for you going from being in these large organizations with a lot of strong balance sheets to now being on your own as an entrepreneur and CEO in this organization? What’s been the most acute difference you’ve noticed between those two settings?

I’m going to tell you a funny one. When I first became CEO of RoseRyan, it was the first time in my entire career I controlled my calendar. That is a funny thing to say, but I was always beholden to somebody else’s calendar. If they said jump, you would jump. You didn’t have a choice. “Come to this meeting.” “I had other plans.” “I don’t care, come to my meeting. I need you in this meeting.” I thought about that, like, “What am I going to do with this power? Am I going to do to everybody what was done to me, or am I going to behave a little bit differently?”

In my first year, I set up my entire calendar. It’s like, “Here’s when we’re going to meet, here are my expectations, and here’s what you’re going to have to deliver this week throughout the whole year.” That gave people freedom in a way because they knew, “This is what Dave expects. This is what I need to do.” It was good for me because then it’s a cadence that is right for the business.

HITC Dave Roberson | Mentorship

Mentorship: When a leader is unwilling to tap into people, thoughts, ideas, and background, they will not succeed over time. Their team won’t be stronger because it’s limited to what’s in their head.


Setting a cadence and then adjusting as you needed to was powerful for me because I had never had the power. I don’t like to think of it that way, but the ability to determine how the company was going to spend time. As a first-time entrepreneur or a first-time leader of of a business, that’s an important consideration. Inside these big companies and how you spend your time, you get lost in the machine. In a smaller company, how every person spends their time is important.

1 person’s contribution out of 100 is different than 1 out of 100,000. Trying to align where people were spending time and being deliberate about it rather than reactive to it was probably the biggest change I found possible at that time. The other thing that’s important to me is a flat organization. RoseRyan has three layers. Kathy and me is one layer. There are the people that report to me, and there are the people that report to them. That’s it.

What’s been the benefit of that? You have 120 some odd employees now. That’s a lot. For that kind of structure, how has that benefited RoseRyan?

It’s because we can move like that. Again, a great example I shared with you is there’s somebody between me and that team who said, “We want to talk directly to you.” “Let’s go.” They were comfortable with that. Back to the listening thing, if I don’t have that, I’ve cut off a big piece of the organization. Kathy and I were doing a round table with every employee in the company. We’ve been owned by ZRG, so we invited groups of 10 or so. They spend an hour with the two of us, and we’re like, “Tell us what’s on your mind. We don’t have an agenda. We want to know what’s on your mind.” We’ve had some fantastic conversations with folks telling us their concerns are with ZRG being the owner rather than Kathy being the owner.

It's one thing to listen and do nothing. It's another thing to listen and change. Click To Tweet

That’s a big change.

The week after, we did the same thing with all the folks. We said, “Let’s do it again. Let’s see where they are now. It’s 90 days later.” At the end of every meeting, what I say to them is, “We made ourselves available to you. I hope you understand anytime, meaning email, texts, or call. We’re here.”

Are people taking you up on it?

They already were, but we’re trying to reinforce that message. Probably one of the other biggest pleasures for me is I can know everybody that works for me. You can know 100 people. When I was at HP, depending on how you count, either 2,000 or 6,000 people worked for me, depending on what part of the organization you looked at. I didn’t know 10% of the people. I show up, talk to them, do all these meetings and stuff, but to know them, not so much. Knowing them is more than what they do. It’s who they are, what their strengths are, and how to take advantage of that.

One person's contribution out of a 100 is very different than one out of 100,000. Click To Tweet

What we’re finding, and we’ve been finding for years, is the number one thing we can do for our employees. No matter the size of the company, it is caring for people and helping them feel like they are connected to the organization on a deeper level and almost as a community. I’ve never thought of the business as a community until recently. When people say it’s like a family, I’m always like, “Kind of, but not really, but it is a community.”

It’s a little bit like a family, but the community is a better word.

What are some of the things you’re finding as you’re going through these discussions that people need to be happy in their jobs?

One of the things in any acquisition we’re finding is what’s coming. Where’s the other shoe? “You keep saying everything’s fine, but Dave, we’ve heard that from other people like you before, and it hasn’t been true.” I’ve had to explain what we did to make sure it was true and explain it, “We were with you.” This goes back to the culture thing. We wanted to make sure that ZRG would treat us in the way we treat you.” They have a motto, which is awesome, “Do no harm.” When they buy a company, do no harm. I told Larry, their CEO, “You need to add another piece to that. We’ll help where we can.”

It's important to help people find the answer without being told the answer. Click To Tweet

Do no harm is a negative to me. We won’t do anything bad, but you’ve done a lot of good things, too. I’d add two things to that. One thing is we’ll help when we can. The other thing we’ve found is there’s a lot of volatility in people’s employment these days. We don’t count on somebody working for us until they show up. We’ve had people accept offers and never come, which is scary. We’ve had people start and leave 3 or 4 weeks later.

With that kind of volatility, I don’t think we could impact it by our culture in that short period of time. I read a great article, but I can’t remember where it was from, saying 90 days is the magic number. If you can keep an employee there for 90 days, they’re probably committed for some longer time, but what you do in those 90 days is critical. I’m going to look at that for RoseRyan. Do we need to do some things differently during that first 90 days so people feel welcomed and heard? What they want is the chance to make a contribution.

Train properly for a lot of organizations, including big organizations. As a matter of fact, IBM was the worst for this, for me, we neglected the importance of an onboarding program. Not orientation. We mix orientation. I joined IBM. They heavily recruited me. I showed up on day one and they’d forgotten I was coming. For six weeks, I didn’t have a job. I swept labs. I rewired because I had a technical background. I was like, “Is this what you’re paying me?”

An official onboarding program makes a big difference. A lot of the work we do is helping put that together with organizations because it doesn’t need to be super complicated. It can be taking a great job description and checking off the things that are on that job description to make sure people know what they’re doing. The worst thing is when we don’t teach them that stuff, and then they feel like they’re not capable of doing the job or not interested in doing the job. That’s why people leave.

Listen and act on what you hear, and you'll be in a much better place as a result. Click To Tweet

We’re looking at using buddies to help with that, too. They’ve been with us for a while and know the ropes a little bit. In fact, I hired someone that will be a consultant and a manager for us. I’ve got a couple of people I’ve already said, “I want you checking in with him every week to make sure he’s coming up to speed.” I told him the same thing, “These folks are there to help you. Take advantage of them as you move forward.” That’s informal because we don’t have a formal program. We’re looking at doing something like that.

I do think buddies are a phenomenal way to do that. It’s different than a mentor. They’re doing that job and teaching people how to do the job, hopefully, and looking over their shoulder, which is different from mentoring. It is much more about coaching. As a final thought, what are some of the things that you would recommend in addition to being a great listener, open-minded, and transparent? Was there anything else that you feel founders and leaders need to do to get their businesses moving faster in regards to their people? 

One thing I maybe leave with this thought. It’s important to help people find the answer without being told the answer. I don’t know if that makes sense to you. In a lot of meetings, I know where we’re going and I know the answer. I need the people I’m working with to get there with me so they own the answer. It’s funny Kathy has seen me do this a few times. She’s like, “Why do you spend so much time doing that?” I said, “Kathy, I spend the time so when the decision is made, everybody is aligned. They’ve all been heard.” We’ve made a better decision because we took the time to listen. I could just go right there, but almost every time I go and listen to what other people think, I come to a better place.

It’s rare that I don’t get insight and then build it into a better decision. That’s trusting your team, expecting them to care and be able to help. That’s a good thing because then you’re respecting the person. You’re saying, “You’re here. I trust you. I believe in you, so help me make this decision.” It’s empowering for that individual. What would you want? A group of people that are empowered, curious, learning, questioning how to get there better, faster, or whatever it is you need to do. That unleashes the power of the organization in a way that you can’t if you’re just sitting in your ivory tower or dictating what needs to be done because no one knows it all. I don’t care how smart you are. Nobody knows everything.

Unleashing the power of your team is the most powerful thing a CEO can do. Sometimes CEOs think, “I have to make all the decisions. I have to do this and that.” No, you don’t. Get your organization to help you make those decisions. Number one, your life gets easier because everything is not on your shoulders. That’s how you keep people around. If I talk to my mentees, this is a great lesson I get from them.

When they want to leave somewhere and I do a lot of coaching with transitioning one company to the next, it’s because they’re not appreciated and people aren’t listening to them. It’s never the pay. There are lots of studies that say that. You can strengthen the organization, get loyalty and the things you want in this simple way. If I could sum it up in two simple sentences or a few words, listen and act on what you hear. You’ll be in a much better place as a result.

Dave Roberson, thank you so much for taking the time to join us. I appreciate all that you do for all these individuals. I wish you the best of luck in your continued tenure there at RoseRyan.

Thanks so much. It’s a real pleasure. You can tell I have a lot of passion for these things. It’s a topic I love talking about. Thanks for giving me a platform to have the conversation.

Thank you. Everyone, thanks for joining us. Tune in for our next interview.

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About David Roberson

HITC Dave Roberson | MentorshipAs president of RoseRyan, David Roberson leads the day to day business and builds upon the firm’s established reputation for taking companies further, faster. He joined RoseRyan in late 2018 as a member of the executive team and managed key areas of the firm. In 2018, David led the large team engagement that provided transitional services for the Symantec-DigiCert divestiture. RoseRyan Founder and Chair Kathy Ryan named David to the CEO post in January 2020 to champion RoseRyan into the next era of growth.

Prior to joining RoseRyan, David spent six years as an advisor to tech companies, leading major projects in the areas of finance, strategy, due diligence, capital structure, corporate governance, sales and human resources. David also served as a senior vice president for Hewlett-Packard Co. Before HP, he was president and CEO at Hitachi Data Systems, where he previously held the titles of COO, CFO, CIO and general counsel. He has served as a director of 12 companies including Brocade, Quantum, IGT, Spansion and IDT. He is currently chairman of the board of Push Technology, a global API management company.

David received a BA from the University of California at Irvine and a JD from Golden Gate University School of Law. He studied financial management at Harvard Business School. In his spare time, David mentors a diverse group of people in various disciplines, from recent college graduates to CEOs.