The Step UP · 2026-06-03 · 28 min
Key moments - from our scoring
Substance score
48 / 100
Five dimensions, 20 points each
Frank Sherwood's career arc from Rosemount Aerospace engineer to CBRE's First Vice President offers a master class in how technical talent must evolve into people-centric leadership. Starting with a brutal feedback loop - being told his project management style left "a few less bodies along the way" - Sherwood invested two years in executive coaching ("finishing school") to soften his South Philadelphia edge. His hardest transition came 30 years ago when he left the corporate side (where he wielded budget authority over service providers) to join CBRE, the $40 billion Fortune 500 real estate firm. Suddenly executing work rather than assigning it, Sherwood had to apologize to service providers for unrealistic deadlines he'd imposed in ignorance. Throughout his career at Rosemount (mentored by founder Vern Heath) and under Roger Staubach's leadership at CBRE, Sherwood absorbed a core principle: treat everyone with dignity, fairness, and respect while prioritizing client needs above all. His coaching advice centers on listening (not speaking), hiring to your weak side, and understanding that what got you promoted won't sustain you at the next level - a lesson critical for newly promoted directors and VPs navigating cross-functional politics and high-net-worth client negotiations.
CBRE (Coldwell Banker Richard Ellis) is the world's largest real estate firm with 150,000 employees, 500 offices, and $40 billion in annual revenue. Sherwood moved from corporate real estate leadership to CBRE 30 years ago to transition from a grueling travel schedule (250,000 miles/year) that was threatening his marriage and family.
His first performance review at Rosemount revealed he was on-time, on-budget, but left bodies behind. An accounting mentor told him he needed to deliver hard messages more diplomatically. Rosemount sent him to a two-year executive coaching program with a private consultant to soften his rough East Coast style and develop people skills.
He realized he'd been giving arbitrary deadlines and fictitious requirements to service providers without understanding the actual difficulty of the work. He had to apologize and learn the financial models, demographics, and tools required to actually execute deals, not just approve them.
Don't make decisions; ask the right questions instead. New leaders often feel pressure to have all the answers, but the real skill is having foresight to ask questions that prompt your team to surface the right solutions.
Vern Heath taught him to review and treat everyone with dignity, fairness, and respect regardless of level. Roger Staubach instilled the principle that client needs always come first, and willingness to donate fees back if projects went wrong, rather than extracting maximum value.
Our reviewer’s read on each dimension, with quotes from the episode.
The episode contains scattered practical observations about leadership transitions, particularly around soft skills development and cross-functional collaboration, but relies heavily on anecdotes and platitudes that feel familiar to experienced operators. The core insights - hire to your weak side, listen more than speak, treat people with dignity - are sound but not novel. Much runtime is spent on biographical narrative rather than dense, actionable frameworks.
you need to be able to tell people to go to hell in such a way that they can hardly wait to make the trip
hire to your weak side. People tend to hire to their strength. And then you wind up getting fed data you already know
The thinking is conventional and largely recycled from mainstream leadership literature. The advice about finding your boss's needs, hiring to weak sides, and listening more mirrors standard executive coaching material. While Sherwood's personal anecdotes are authentic, they don't generate fresh frameworks or counterintuitive arguments. The episode reads as competent reinforcement of known wisdom rather than original thinking.
find out what your boss needs, anticipate what he needs, and get it for him before he asks you for it
it's important to have the right questions than have answers
Frank Sherwood is a legitimate senior operator - First VP at CBRE (Fortune 500, $40B revenue, 150k employees) with multi-decade career spanning engineering management, corporate real estate, and service delivery. He has real P&L responsibility and cross-functional leadership experience. However, he is not a household name in leadership circles and lacks the gravitas of Fortune 100 CEOs or widely-recognized transformational leaders. His caliber is solid but not exceptional.
first vice president at cbre
the largest real estate firm on the planet. They were headquartered in Los Angeles for 100 years
The episode is sparse on concrete metrics, timelines, and named examples beyond the guest's own companies (Rosemount, CBRE, Roger Staubach's firm). Financial figures are mentioned casually ($40B at CBRE, 250k miles/year travel) but not tied to specific outcomes or lessons. Most advice is delivered at abstraction level - no case studies, no before/after data, no quantified results from leadership interventions. Personal anecdotes substitute for rigorous evidence.
I was doing 250,000 miles a year, most of the China, building manufacturing plants up and down the Pacific rail, from Beijing down to Singapore
the largest real estate firm on the planet. They were headquartered in Los Angeles for 100 years
The host asks reasonable open-ended questions and does attempt some follow-ups (e.g., clarifying what 'finishing school' meant, asking about peer relationships). However, the conversation lacks sharpness and depth. The host rarely pushes back, challenge assumptions, or dig into contradictions. Questions are often softball and the host seems more interested in letting the guest tell stories than in extracting specific operational lessons. There's minimal productive tension or Socratic probing.
What was that finishing school
what has your experience been or at least either both having to sort of reach across the aisle, so to speak, with these people that maybe have very different goals from you
Computed from the transcript - who did the talking, and the words that came up most.
What happens when your technical brilliance gets you promoted - and then becomes your biggest liability? Frank Sherwood spent his early career as a high-performing engineer who needed "finishing school" to survive leadership. In this conversation, Frank traces his career from aerospace engineering at Rosemount to managing a 500-site global real estate portfolio to joining CBRE - and what each transition demanded of him as a leader. Guest: Frank Sherwood is First Vice President at CBRE, with a 20+ year career in corporate real estate spanning leadership roles at JLL, Staubach, Cushman & Wakefield, and CRESA, including managing real estate portfolios across 75 countries.
Transcribed and scored by The B2B Podcast Index.
One of my mentors was on the accounting side. I was on the engineering side. And he would tell me that you need to be able to tell people to go to hell in such a way that they can hardly wait to make the trip. Yeah, you have to soften it a little bit.
And that was not my natural style growing up in South Philadelphia, east coast. A little bit of edge. I mean, that. That wasn't my first go to.
When someone hit you on one cheek, I was not inclined to turn the other cheek. So I learned early, thanks to a good mentor. Hi there and welcome to the Step up podcast. I'm your host, Kent Knievel.
Every week I talk to experts who focus on helping leaders step up their leadership game and leaders telling their stories of growing up through the ranks. If you're new to the show, do me a favor and subscribe so you never miss an episode. One last thing. As a leadership development consultant and executive coach, a focus area of mine is supporting newly promoted leaders.
One in three promotions fail because we never teach newly minted VPs how to stop being a director or a newly promoted director how to stop being a manager. If that's you, or if you support a leader who has been recently promoted, I encourage you to visit my website at Kent Coach Toolkit and download a free copy of the Promoted Leader Toolkit filled with practical advice and tools to help new leaders stick the landing and truly step up to their new leadership level. All right, I've dillied and dallied long enough.
On with the show. Welcome, everybody. Today I'm really excited to be talking to Frank Sherwood, first vice president at cbre. Today's episode's going to be much more of a sort of leader biographical interview, as opposed to talking to a consultant or an author about their thoughts on leadership.
So, Frank, I'm really excited to hear hear your thoughts on leadership as a leader. Welcome to the podcast today. Happy to be here. Thank you very much.
Well, before I start kind of digging into some of the specific questions I might have, I'd love for you to introduce yourself to the audience and then maybe give that brush strokes of your sort of career history. Well, background is the oldest of three children. I grew up in Philadelphia area, went to engineering school at Iowa State in Ames, Iowa. My first job was in Minneapolis and been up here ever since.
So it's home now. And it's wonderful here during summer, both weeks of it. So if you can get a chance to come during summer, you'll enjoy it. Yeah, I always say spring is really Nice for a few days.
The winter mud, a few days of spring and then immediately into summer. There you go. So you never left. We got our hooks in you and you decided.
Yes. Married a local girl. I have three grown children and I went to graduate school at University of St. Thomas for my MBA.
And it's home. It's home now. Well, in these interviews I like to sort of talk about leadership transitions. So specifically, you know, and I'll, I'll.
We'll see with following the conversation. We'll see the kind of time we have. But you know, we'll probably start at the beginning of the career of, you know, what was that? You know, tell me about how you got into your very first leadership role.
How intentional was it and would love to just kind of hear some of the learnings that you had of kind of going from not leading people to suddenly leading people. First job was as a young buck engineer. I couldn't even spell engineer, but I was one and it worked really well until a short layoff and went around the corner to a company called Rosemont Aerospace and joined them as a senior level engineer. Had a very good staff working on military aircraft.
So it was a very quick transition from entry level to engineering manager. And I think we had talked about what I first met you, right, that my, my grandmother learned English working for Rosemount in one of their space programs, I believe, or whatever they were. Yeah. So when you think about that very first management role, what do you wish that you would have learned faster?
Right. It's very different going from leading yourself and just worrying about your own work to suddenly, you know, you're accountable for the work of a team. What were some of the big lessons learned you had that maybe even you wish you would have learned quicker? Engineering schools, they're very technically trained, so we don't get a lot of humanities.
And most of us come out very thing oriented and not very people oriented. I recall my very first early performance review where they said if they looked up project manager in the dictionary, there'd be a picture of me always on time, always on schedule, always under budget. The problem is we want to see a few less bodies along the way. They said that you just can't use that east coast rough edge.
You need to soften it up. And they sent me to finishing school for two years to try and soften the rough edges. So having the people skills was paramount. After you get through the pure engineering roles, it's more about people skills.
What was that? Finishing school. You've said that before. What does that mean.
Well, I was two years with a gentleman who was a private consultant to Rosemont. They put me through his training and it did a lot of good. So good enough that you kind of kept growing in your career. So what was sort of, you know, when you think about getting to that next level, right, is your, you know, the very first level of leaders being, you know, you're managing individual contributors.
What about, you know, that next level you got to where you were now maybe managing other first time managers. The hard part for me was when I left the pure engineering role and moved over from the corporate side to being a service provider, which I am now a cbre. And I was rudely awakened by how difficult it was to actually do the work. It's one thing to manage the work.
It's a whole different level of skillset to do the work. So the first thing I did was called up my service provider and apologize to him for all the arbitrary deadlines and fictitious requirements that I gave him. I had no idea what it took to really do the work well. So for our audience, because I feel like maybe shame on me.
I should have had you do this at the beginning. What is C? Now I'm going to get it. All right.
Cbre. Cbre. And. And CBRE stands for four Dead Guys.
Coldwell banker Richard Ellis. We get tired of saying that, but it is the largest real estate firm on the planet. They were headquartered in Los Angeles for 100 years, but they finally gave up on Governor Newsom. And now we're headquartered in Dallas and they have 500 offices, 150,000 employees.
We're Fortune 500. Will do $40 billion this year. Wow. Nice.
And so when you say just for the audience, when you say, you know, you had to call your service provider and apologize. So just define for the audience, what does that mean? What is being a service provider in this? Well, when you're a head of real est estate in a corporation like I was, you tend to become a little bit confused about your worth.
You're reading your own press releases. I was having, you know, dinners in Paris, lunches in Beijing. I mean, I was really good. Just.
Just ask me. The situation was I wasn't good, but I could pull the purse string. So a lot of people called on me. I thought that I knew a lot of things.
But when you're in a role like that, it's a very small staff and you outsource most of the work to firms like CBRE who do the actual heavy lifting. And I was in a corporate Role. It was a very good job for a young single guy. The problem was I was married and I had three kids and I was doing 250,000 miles a year, most of the China, building manufacturing plants up and down the Pacific rail, from Beijing down to Singapore and as far west as Xi'.
An. So it was not going to end well for me. I could see how it was going. Cause my bosses were all divorced and I was headed that way.
So. So 30 years ago, I moved to the dark side of the forest and I'm still married today. So it was a good call. Amazing.
So what was that? So you, you know, you had said early on you had to call and apologize to your service provider. So you had kind of said that the work was, was much harder. So what was that, what was it that you know from doing the work versus leading those who do the work?
What was that learning for you? At that time? The learning curve was very, very steep. I knew literally a week after I left the corporate world that it was a mistake, but I was too proud to go back.
So I was determined to make it work. And I did make it work. But it was a lot of pain and suffering learning the actual demographics, the financial models and the tools and the people skills needed to make this career a success. It's very important in this line of work to be able to inject humor into a situation and to have the people skills.
We would have many people applying for jobs and they would say, well, I have a BS, MS, PhD, and I'm borderline genius, but I can't get along with people. And we would say, well, really can't use you here because all we have is people. You have to be able to get your idea across to a common, ordinary person. If you can't do that, we have no use for you.
People skills was a very difficult thing to learn properly. Well, it sounds like you were. Yeah, you were saying, you know, both from your engineering background, that was an initial hill to climb. Right, Was.
And why you went to finishing school. So as you think about the time you spent, because I'd assume at some point you moved beyond managing individuals to managing the people who manage individuals. So I'd be very curious what your thoughts are on how that was uniquely different from your perspective than managing individuals. Well, we learned early that it was, in order to be successful, the best course would be to hire to your weak side.
People tend to hire to their strength. And then you wind up getting fed data you already know. It's important, especially for engineering talent, to Hire people who are trained in finance and the humanities and the softer skills so you can get a different line of reasoning. You know, in the manufacturing side, we often would poke fun at engineers, saying that at some point you have to actually shoot the engineer and then build the product.
You just can't keep designing it till it's perfect. It's never going to be perfect. Customers got a deadline, you've got to ship the thing. So being able to ship means you have to work with other departments who are not necessarily interested in your toy.
You know, you've got to be able to use your people skills to help them help you. I feel like that's, you know, at least in my experience, both assessing leaders, coaching leaders, teaching leadership workshops. A really critical skill. Right.
Is how are you actually connecting with your peers. Right. I feel like there's so much focus that people make on, especially when you're entering into an organization or you're promoted, is getting to know that team that reports to you. But I think one thing that is easy to overlook until sometimes it's too late is that peer set, especially that cross functional peer set, like you were saying, where, you know, you need these people to accept your ideas.
Or somewhere on the chain here they're either taking your inputs and needing to go do something with it, or you're getting their inputs to do something with. Would love to hear your thoughts on or even, you know, your experience with having to sort of build those coalitions, build those alliances with people who don't report to you. Right. And yet, you know, you, they are a huge part of your success.
You're a huge part of their success in the end as well. On the engineering side, I was at Rosemount and that was founded by a gentleman named Vern Heath. And when I was starting with him, I saw him in the hallway and I'm not very bashful. I wanted to meet the guy and I walked up to him and I said, I'm Frank.
And he stops me and he says, you're Frank Sherwood. You have an engineering degree from Iowa State. You joined us two weeks ago and you're in our aerospace group. And I said, yes, I am, sir.
And he taught me that, you know, at that level, you even review entry level people and you treat everyone with dignity, fairness and respect. So that was the training ground for me there. On the corporate side, the best years of my career were with Roger Staubach. You may Recall Roger as 12 years in the NFL, ex naval officer, married his high school sweetheart, a very gentleman gentleman.
He taught Us that you make sure that the client needs always come first and if something is somehow going wrong on a project, you want to donate the fee back to the client because Roger's going to do a review on every single project and he'll donate it anyway. So you may as well just do it. So it was just a matter of learning how to service not only your staff, treating them with dignity, fairness and respect, but treating the client as the king primary reason we exist. Well, and sometimes those, those cross functional peers, right.
Sometimes goals and objectives can seem or feel like they're in conflict with one another. Right. That, that with using your example of at some point you have to shoot the engineers and build the product. Right.
That sometimes the goals in engineering might be very different from. Right. The marketing goals from products goals. Right.
So would love to, you know, what has your experience been or at least either both having to sort of reach across the aisle, so to speak, with these people that maybe have very different goals from you or I would, I would also say your experience coaching others to figure that out. Too fortunate being at Rosemont to have very good mentors. And one of my mentors was on the accounting side, I was on the engineering side. And he would tell me that you need to be able to tell people to go to hell in such a way that they can hardly wait to make the trip.
Yeah, you have to soften it a little bit. And that was not my natural style growing up in South Philadelphia, east coast, a little bit of edge. I mean that wasn't my first go to when someone hit you on one cheek, I was not inclined to turn the other cheek. I was inclined to go to the juggler and remove that obstacle.
So I learned early thanks to a good mentor. So seeing as you've changed companies a time or two, what has either been your experience or what's your advice to people when you are suddenly either, let's take it that way. When you are suddenly joining a new company and you not only need to learn again, like especially if you're in management or middle or upper level management, right. You have so many people to meet and learn about.
Right. You've got your immediate team, you've got your immediate peers, right. That might sit on the exact same team as you and your boss, so to speak, let alone other personalities and cross functionals that might be, you know, one step removed. What's your advice for people who are stepping into that sort of brand new situation on how to make those connections, how to spend.
Well, it's, it's Important to a little bit easier on yourself. We all tend to be our own worst critic and self doubt creeps in. There's plenty of books on the imposter syndrome and every leader faces that they, they feel at some point that they're inadequate in some arena. But the reality is you don't have to have it perfect.
You just have to move the direction of the organization in the right way. And maybe it's a zigzag curve, but at least you're moving the organization. So it's important to surround yourself with people that are smarter than you and basically get out of the way. I always liked what Dale Carnegie said was that you know, you can get anything you want in life as long as you help enough people get what they want.
So I would try to figure out what is this guy I want, I will get it for him and someday we'll be able to work together and hopefully improve both situations. I'm curious, as you think about some of those times where you were new in role, was there a moment early in a new role when you realized right there's the. I think it's Jim. Jim Collins wrote the book.
What got you here won't get you there. Right. Can you think of an experience where as you think back to it, you kind of hit that lesson? The like realizing what got me to this role isn't actually what I need anymore to be successful.
Well, that is particularly true in technology fields. The half life of an engineer is four years. So four years out of school, half of what you learned is totally obsolete. So eight years out of school, you actually know nothing that's useful on technology.
You really need to be either managing people or continuing to go back for more education. So that's why so many of them move from the pure technology role to a management role. But it's important to realize that those skills are just not going to be useful going forward and spend as much time as you can reading other trade journals or encyclicals from arenas that are outside of your primary school of thought. So it helps me to read things from the financial community, the Harvard Business Reviews and those types of articles and magazines like the Economist.
So I understand what is really happening with the market rather than just my, my object view of my own situation. Of all the leadership roles and leadership levels, right, that you've been in, which one do you feel like? You know, what was the hardest leadership level that you were promoted into and what made it so difficult? Although the hardest part was really going from the corporate side Where I was in charge of the purse strings to the service provider side.
It just was a night and day change in how I functioned, how I thought about the world and how I thought about other people. It was going from a purely execution driven strategy to a collaborative strategy. Is it also maybe a difference between execution and arguably sales to some degree too? Yes.
I mean, we're all in sales at one level or another. And it's a testament to my skills as a salesman that my wife married me because she was 21, I was 27, she had no idea what she was doing. I sold her a line of goods that she's still paying for today. So we're all selling something.
It was just not very readily apparent in the engineering world that we're actually really selling ideas and selling concepts to people who aren't necessarily interested in our mission. Did you ever have, you know, sometimes we go from being, you know, being someone's peer to suddenly being their manager or even, you know, someone who was a mentor is now your peer. Right. I'd be curious, what have some of the stickier relationship evolutions been that you've had to navigate?
Those are difficult. And that had also happened to me where I was working in an environment where one of my subordinates became my boss. And it just a matter of recognizing the terrain, being willing to learn from that individual, and not placing judgment on the situation or overanalyzing their thought process. Because left to our own devices, you can start to feel like a victim sometimes.
You don't want to fall into that trap because it's a downward spiral that lead to very bad consequences. Looking back. And then I want to talk a little bit about, you know, you've had a lot of managers reporting into you too at this point. Right.
But before we get there, looking back, what do you wish someone had told you on day one of your most challenging promotion? Well, it goes back to that self doubt issue. I mean, we're really smarter than we give ourselves credit for and it's important to give ourselves a break and not wind up being our own worst critic. So it helped me to move forward by using the skills of my team and helping them to be the best version of themselves.
So let's talk a little bit about that. Right. Because one of the key roles, the higher you sort of go in leadership, is to create other leaders. So what are some of the, what are some of the things that you have found that you have needed to sort of time and again coach new leaders around?
What are some of those key thematic Areas that you find yourself sort of regularly giving leaders feedback on or, you know, helping build their leadership skills around. It's primarily communications styles and the deals that we work on in the commercial real estate side are very intense. You're dealing with very intelligent, high net worth individuals, have their own agendas. And what we try to do is listen more than we speak because the listening side is where all the knowledge is gained.
Reminds me of one of my trips in China when I was going to a Buddhist temple and I speak Mandarin. As I was going up the levels, the monks were saying, welcome, wise man and go to the next level. He says, welcome, wise man. And I said to my guide, why is he saying welcome, wise man?
And he said, well, you have big ears. And I felt like saying, yes, well, you look at Buddha. Buddha has big ears. The more bigger your ears, the more you listen.
The more you listen, the smarter you are. So they view you as a wise man from a foreign country. So we tried real hard, you know, to listen more than we speak. And that's very natural in the US we all tend to be very independent.
I'm very stoic, very John Wayne, and that tends to kill a lot of deals if you're not willing to listen to the other side and empathize with where their pain points are and where their pressure points are and how you can help them achieve their goals. So it's very difficult to make that happen. That is what we try to do here, is make a deal happen where none really exists. Well, as I, as we are kind of winding down a bit, I want to jump into.
So. Right. One of the, and obviously, you know, some of the, what's behind some of the questions I'm asking you today. Right.
Is around leadership transitions. Right. So first looking at those leaders who are still at a point in their career where they are looking to get to that next level and their career. Right.
So we're talking about people who are looking for a promotion. What's one practical piece of advice you have for those leaders out there who are still sort of climbing the ladder? My advice would be, you know, find out what your boss needs, anticipate what he needs, and get it for him before he asks you for it. That takes a little bit of clairvoyance sometime to figure out where he's going.
But if you do the research and you can use tools like AI to help you find that, but it's important to be a student of that boss and understand what he needs, get it for him before he asks you for it that will show him that you have the adaptability and that you're material that should be promoted, you have the skill set and you are ready for your next promotion. What about those leaders who were just promoted? Right. So they were maybe just a manager, now they're a director or they were just a director, now they're a VP somewhere.
It's week one or month one at the new level. What's one piece of advice you have for them to help kind of shed the old level and step up their game into this new level of leadership? That first week, I would certainly not be making any decisions. I would just go around and ask the right questions.
I think it's more important to have the right questions than have answers. A lot of people think that because they're the new VP in this role, they should have all the answers, but they really don't. They're there to have the foresight to ask the right questions. And you keep asking the right questions.
The right solution will appear from your team and then you, you will all be successful. Any other sort of words of wisdom out there for folks who are trying to step up their leadership game? Words of wisdom from Frank Sherwood I. Just think it's primarily important to like the topic that Vern Heath taught me at Rosemont Aerospace, which was you treat everyone with dignity, fairness and respect and you just make sure that they genuinely understand that you have their best interests at heart.
If you can convey that in a meaningful way, everyone will be successful. Frank. Frank, thank you so much for being on the show today. I really appreciate your time and love the laughs.
I appreciate the humor you bring. My pleasure. Thank you for inviting me and I'm sure we'll see you again. That brings us to the end of our episode.
Thank you for listening. I'd encourage you to head on over to my website, Kent Coach and start a conversation with me there. Or check out my promoted leader Toolkit at Kent Coach Toolkit. Before you go on with your day, please take a moment to leave a rating and a review.
Wherever you listen to podcasts, click the five stars. That helps put this podcast in front of more ears. Till next time, take it easy, Sam.
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