Growing Leaders with Matt Blumberg

Reading Time: 17 Minutes

In this episode with Matt Blumberg we discuss growing leaders and developing a strong company culture.

Takeaways We Learned from Matt…

Get to know people as people.

Building strong relationships and understanding what motivates individuals on a personal level allows for greater empathy and effective deployment of their skills. By knowing their interests, fears, and aspirations, leaders can create an environment where people thrive.

The health of the leadership team is crucial.

Organizational effectiveness heavily relies on the cohesion and trust within the leadership team. Regardless of individual talent, when leaders fail to come together, politics and a lack of trust can hinder progress. Prioritizing the health and functioning of the leadership team is essential for overall success.

Misalignment hampers growth.

Unhealthy relationships and environments caused by misalignment can impede business growth. It’s important for leaders to recognize that growing and succeeding in a healthy manner has compounding benefits. By fostering a supportive and aligned culture, businesses can achieve exponential growth.

Employee autonomy and creativity drive productivity.

Leaders should empower their employees with autonomy and the freedom to exercise their creativity. By giving individuals the opportunity to contribute beyond task completion and encouraging their personal growth, leaders can tap into their full potential and extract greater value from their teams.

Value people as the biggest assets.

Recognize the value of employees as the primary assets of the organization. Treating them with care, trust, and respect aligns with the company’s stated values and facilitates a positive work environment. By valuing employees, businesses can unlock their full potential and achieve both human and business success.

Reflecting on leadership experiences leads to growth.

The initial experiences as a leader may not always align with one’s ideal approach. Reflecting on past mistakes and learning from them is crucial for personal growth and development as a leader. Embracing new perspectives, such as delegation, trust, and individual recognition, can enhance leadership effectiveness.

Learn from early leadership mistakes.

Many leaders start by emulating the leadership styles they have observed, which may not always be effective. Recognizing the need for improvement and learning from initial management experiences allows leaders to evolve and develop better strategies for leading their teams.

Growing leaders is crucial for organizational success.

Investing in coaching, development, and feedback for leaders yields substantial benefits that outweigh the costs. Good leadership can significantly enhance organizational productivity.

Prioritize hiring for values when selecting leaders.

Leaders set the tone for the organization, so it is essential to ensure they align with the company’s values. Hiring leaders who possess both competence and values is ten times more important than with other roles.

Embrace a steady diet of feedback.

Instead of relying on annual performance reviews, create a culture of frequent and timely feedback. D-stigmatize feedback by making it a regular part of team interactions, both positive and negative, and encourage open communication.

Leverage the advantages of work from anywhere and fractional work.

With the rise of remote work and gig economy, organizations can benefit from employing people who can work from anywhere. Fractional work, even at the executive level, offers cost-effective solutions and flexibility for mid-career or late-career professionals.

Build an effective and strategic board.

View the board as a strategic asset by carefully selecting independent directors who bring diverse backgrounds, experiences, and perspectives. Cultivate a team mindset within the board, foster communication, trust, and social cohesion.

Optimize board meetings for effectiveness.

Produce clear and concise materials, distribute them well in advance, and ensure they focus on key topics for discussion, decisions, and approvals. Align the board’s operating rhythm with the company’s operating system to streamline reporting and decision-making processes.

About Matt Blumberg

Matt Blumberg is a technology entrepreneur, business builder, and CEO of Bolster.

Matt’s company, Bolster, is an on-demand executive talent marketplace that helps accelerate companies’ growth. Bolster connects companies with experienced, vetted executives for interim, fractional, advisory, project-based or board roles.

Matt has been recognized as one of New York’s 100 most influential technology leaders by Business Insider, by Crain’s as one of New York’s Top Entrepreneurs, and by Ernst & Young as an Entrepreneur of the Year finalist.

Before Bolster, Matt built businesses and worked in marketing, consulting, and venture capital. He is the author of Startup CEO, Startup CXO, and Startup Boards, set to be released in June 2022.

Read the Transcript

Allison: Welcome back to the Deliberate Leaders podcast. I am your Host and Executive Business Coach Allison Dunn. Our topic today is growing leaders. And our guest is Matt Bloomberg. That is a technology entrepreneur, a business builder, and CEO of Bolster, which is an on demand executive talent marketplace. He is also the author of Startup CEO, Startup CXO. And Startup boards. Matt, thank you so much for joining us here today.

Matt: Good to be here. Allison.

Allison: I love to kick these off with a deliberate conversation. What would be your number one leadership tip for our listeners?

Matt: I think my number one leadership tip can I give you two?

Allison: Sure.

Matt: In no particular order.

Number one is get to know people as people. I have just always found that the more you don’t have to be friends with everybody. But you have to know everybody. And you have to understand what makes them tick.

You know, what’s their home life like? What gets them out of bed in the morning? What are their hobbies? What are they excited about? What are they afraid of? And all those things, I think just help you do a better job of having empathy toward them. And also figuring out how to best deploy them, you know how to make them successful, in ways that make your company successful. So get to know people as people is number one on my list.

The second one is I think the most important thing that I can point to around organizational effectiveness is the health of the leadership team, as a team.

And I, you know, I’ve seen companies where there are talented leaders, but when they don’t come together well as a leadership team. When there’s politics, when there’s a lack of trust, when there’s fear of conflict, then everything falls apart, it doesn’t matter how talented they are, it’s really difficult for the company to move forward. productively. So I always say the most important thing for me is the health and functioning of the leadership team.

Allison: I appreciate both of your tips. And I would say I often see that like the misalignment is what causes a lot of unhealthy relationships and environments inside of businesses. And I believe that often businesses say but we’re still growing and we’re still successful. But there is a toll to be paid when it’s not in a healthy way.

Matt: Sure, yeah. It doesn’t mean you couldn’t be growing more or being more successful.

Allison: Actually, I would say you could compound to that growth exponentially if you were doing it in a healthy way.

Matt: Right. Just think about how much more, by the way, like I’ve seen CEOs get fired for running healthy growing businesses, because the business could be doing better.

Allison: Good tips. Thanks. So my first question for you is regarding your own experience with leaders early in your career and what shaped how you think about leadership today?

Matt: Yeah, I had a few different jobs before I started my first company, and I worked for a variety of managers of them. Sometimes multiple managers, a management consulting firm, you sort of had a new leader on every project or new leader of the office, I worked in a venture capital firm, I worked for multiple partners there. I worked at a media technology interactive services company kind of at the very beginning of the commercial internet.

And the thing that I took away from all three of those experiences across multiple managers was that all of these companies were knowledge economy companies, which is a totally dated term now, right? But in the in the mid 90s, or early 90s was a real term. And they all had some form of like a value written on the wall somewhere. That’s said like our people are our biggest assets or our assets walk out the door at five o’clock, five o’clock every day or something like that.

And yet, they all treated their employees with the same level of, of care control and have lack of trust that you would have expected someone to treat a factory floor worker in the 1800s.

And so they had this very incongruous approach to their, to their values and to in fact, what were the biggest assets and the businesses.

And I learned a lot from those businesses, and I liked a lot of those managers as people. But I kept seeing this theme over and over again, that the, the average employee was not giving it, his or her all. Because they, they didn’t have to, they just had to do what they were managed to task for.

And I just kept feeling over and over again, like, wow, we could be getting so much more out of people here, if they had more autonomy, if they had more ability to be creative and to exercise their brains, as opposed to just doing what someone told them to do.

And it’s one of the reasons I decided to become an entrepreneur was that I wanted to create a corporate culture or environment or multiple ones over the years, that really did value people the way I thought people needed to be valued. And that it was good to, like good as a human, but also good business.

Allison: I feel that there’s been a major shift, just even in the last few years as to how leaders, lead people. And it’s been somewhat forced, you know, obviously, for a variety of obvious reasons. I’m curious now, you kind of opened up the opportunity to share your first experience as a manager or leader, and how that shapes the way that you lead today.

Matt: Yeah, so I feel so bad for the first woman I ever managed. Alyssa, I remember her quite well. And I was so excited to like, okay, I’ve just been promoted now as a manager, and I had one person reporting to me. And I think I just must have driven her crazy, like I was micromanager extraordinaire, ah, and I was sort of doing what I had learned late, I had doing what I had observed from all of these other managers to sort of like, beat me harder. And then what happened was really interesting. And I consider myself very fortunate that it happened this way, I sort of feel like, if I had gone from one person on my team to two, I would have kind of kept going the same to three, I could have kept going the same. But because of the way my own trajectory worked and getting promoted, I went from having one direct report to running like a 30 person department.

Okay. And, and that model that I had broke, like, there was no way that I could transfer that I could take that model of like command and control to a multi level 30 person organization.

And it forced me to rethink everything in one shot. And I certainly won’t claim that, you know, the people who reported to me next got the best of me if I look at my whole arc of my career as a leader, but they certainly got a lot better of me than the poor one person who I started with. So, you know, it just forced a level of delegation, it forced a level of trust, it forced a level of, of upping my own game in terms of how I communicate.

I think I was still probably a little bit of a Pace Setter. But I think I did much, much better at recognizing individuals for who they we and managing them to their strengths and managing them to outcomes as opposed to tasks and sort of all of those things. But it only happened because I had that big like step function in one shot.

Allison: And I think probably many of our listeners can resonate of being first LED in a way that you didn’t necessarily resonate with you and then you go well, I can do it better and or doing it exactly the way that you’ve been shown. I am very thankful For my experiences, and thank you for sharing yours, I think my first person that I managed or supervised, she stayed with me for a very, very long time.

Matt: We’re probably a lot better than I was.

Allison: No, I’m just I’m pretty sure I was pretty bad. But I did learn through that process. And so my Shelly, thank you for letting me learn through you. So we, I guess we all have someone to be thankful for, for being kind in our leadership development. So let’s talk how do we grow leaders today? How do we do it effectively, what should we be thinking about as an organization, so that we’re not putting our or our people who are being managed at risk?


I think growing leaders is one of the one of the best things you can do as a CEO, if you have any scale to your organization, in particular, if the organization is growing. And you know, the benefits you have. So outweigh the costs of investing in, you know, coaching and development and feedback and any of those things. You know, if good leadership makes your organization 5%, more productive, 10% more productive, 50% more productive. It’s just worth every nickel you put into it.

And, you know, I think we, the organizations I’ve led over the years, we have invested quite a bit in, in growing leaders. We, we invest a lot in mentorship and coaching. And sometimes that’s engaging outside coaches. But sometimes it’s just setting up good internal mentorship programs. We invest a lot in communication, and communication training.

We have an absolutely wonderful Consultant Program that we’ve used over the years, teaching us how to listen, and how to be present, and how to communicate and speak in such a way that that push puts the importance of what you’re saying on the audience as opposed to on you. And on and even on your content. That makes a makes a big, big difference. But I think they’re, you know, they’re kind of a couple of other things, I would point to that have meant a lot to us in our organizations over the years as we’ve grown leaders.

So one is you have to hire for values even more than you otherwise would. So I always encourage you, no matter who you’re hiring, to hire for competency as well as values. But it’s, it’s 10 times more important with leaders because leaders do set the tone for the organization.

And you can have a leader that’s super, super talented. But if they if they don’t fit with the values of your organization, they’re going to get rejected by the organization, they’re going to create a lot of thrash and noise along the way, and probably cost you not just productivity, but probably cost you some good people too. So think hiring for values is absolutely critical.

One of the other things that that I really come to appreciate over the years is not just the value of feedback.

I’ve always believed in the value of feedback, but in the value of a steady diet of feedback. And you know, part of that is because when you get a performance review once a year, like who the heck remembers what happened 11 months ago, right? What you’re really getting is like the last month or two where the feedback but you’re only getting a once a year. And there’s also this, I think sort of cultural stigma attached to the performance, the big performance review, right, or even the big 360. So what we’ve tried to do over the years is really D stigmatize feedback. And part of the way we do that is we make it so frequent, that it just can’t be, you know, shrouded in mystery. And we also almost always make it not anonymous.

So the pattern of feedback in our organizations has evolved to the point where we do every team is doing some sort of peer feedback system every quarter. Okay, so every 90 days every night is and they’re all doing it in a room together. And they actually have to look at each other and give each other the feedback. And that has really broken down a lot of barriers to communication to hear of conflict. You know, obviously if there’s a critical performance problem, someone’s going to deal with it out of cycle but it’s here’s the ins and outs of regular feedback. I’ve just found that incredibly helpful. So, you know, some of these things are not just about growing leaders, but they’re probably more important when it comes to leaders.

Allison: I think feedback is just a consistent conversation that should be had. So formalizing it in a group setting where if I have feedback directly for you on something that you can improve with working with my team, or whatever it is, I’m just curious, how in depth does that go? Are you teeing up just a few questions, and everyone’s coming prepared to provide a critical piece of feedback? Or is it both positive?

Matt: It’s positive and negative. And I would say we vary the format quarter for quarter. And mostly because you get boring if you get to actually exactly the same thing every quarter. But it is always some positives and some negatives. Sometimes it’s inbound. So you know, there’s some pre work where everyone fills out some worksheet, and then in the room, you’re discussing it. Sometimes it’s outbound or solicited. So the person sits down and says, All right, here’s my own assessment of what’s working and what’s not working for me. And let me look around the room at my teammates and ask you, is this the right assessment? Are you getting what you need from me? Are you not getting what you need from me? And, you know, it’s very, it’s very disarming, when someone actually asks you for feedback, as opposed to someone from HR telling you that you have to write up a form. And, you know, it’s I think it’s just a lot more effective. It’s great.

Allison: In your crystal ball, if you have one, what would you say is the future of work and the competition for talents?

Matt: You know, there are clearly a couple of big trends going on no matter where, what sector you’re in, right? One is, work from anywhere. So that doesn’t work. If you run a farm, I get that it doesn’t work if you run a manufacturing plant, but work from anywhere is clearly a big theme in lots of pockets of the economy. And the other is fractional work is you know, is gig work. And you know, the people sort of downplay that sometimes Oh, that’s for Uber drivers, or that’s for, you know, graphic designers who put themselves out on Upwork, or for people on TaskRabbit.

Actually, gig work is becoming more and more common in white collar jobs, and even at executive jobs. And it’s one of the things that my company Bolster does is we actually place fractional executives at startups and scale ups.

And you would be amazed, like, you would sort of think like God, who would want a part time CTO, or who would want a part time Chief Revenue Officer, like it’s not possible, it’s possible. Not only is it possible, it’s incredibly cost effective for the company. And it’s very freeing for someone who’s mid career or late career and doesn’t want a full time job anymore. Maybe they just want to a few clients. So I think in the world of executives 20 years ago, you would probably say that kind of person Oh, they’re a consultant. You know, that’s because they couldn’t really get a full time job. Now it’s the other way around. It’s like, Oh, they’ve made it so now they’ve kind of earned the right to be a consultant.

Allison: It’s interesting way to put it what would be the most common fractional need a startup has the easiest one to point to is CFO.

Matt: Okay, right. I mean, startups need to have books they need the you know, but a founder can figure out QuickBooks or do something in Excel for a while, but you do need someone who’s actually an accounting professional or finance professional periodically to like look at things to make sure they’re going well so hat’s one of the first ones that companies hire, but honestly we’ve placed fractional executives in every single functional area. HR is probably another one that’s easy to do fractional legal like at the corporate ones tend to be a little easier, but plenty of Sales Marketing, product technology leaders as well.

Allison: I understand that you also do like a board level service as well as you kind of position how important that is and kind of what that helps an organization in start. or Scout mode accomplish.

Matt: You know, we do a lot of boards, Director searches. And we spend a lot of time kind of coaching our clients or we’re all CEOs and, and how to build an effective board and how to lead an effective board. And one of the things that’s fairly common when I sit down and talk to a to a CEO or founder is when the subject of the board comes up to kind of roll their eyes. And they’re like, the board, right, I have to do all this work for them. And they sort have this view that their board is attacks.

And what I always tell them when I start working with them, is that our objective is to have them reframe that the board is not a tax, but the board is actually a strategic asset.

But you only get to that place of the board being a strategic asset, if you do a really good job building it and running it, otherwise it is attacks. So you know, taking the right approach to building your board, which first and foremost means having really good independent directors on it. And an independent director means they’re not on the management team. They’re not a founder, and they’re not a VC, they’re not an investor. So independent directors make for great boards.

Diversity of everything, diversity of thought, diversity of background diversity of experience, diversity of demographics, makes for a better board.

And just giving a lot of thought to like, alright, well what kind of board do I want to build and who do I want on it and what voice needs to be around the table that’s not otherwise in my ear as a senior executive.

So building the board is the first step to having a great board. I think the second thing is being really intentional and taking a lot of care, to thinking about your board as a team.

And it’s really easy for CEOs thing, oh, I got a team, it’s my management team. And the board is this thing, and it’s a amorphous thing out there somewhere. But if you think of your board as a team, and you pay attention to things like communication, trust, the social aspects of the team, you start finding that your board gels as a team and is therefore much more effective and impactful as a team.

And, you know, I would say the next thing is, is having great board meetings. So the boards frequently, you know, their only interaction as a group is meeting and some companies, that’s four times a year, so it’s not all that much. So it actually is worth taking the time to make sure that you’re doing a great job of producing materials for your board, that they’re easy to read, they’re in a single PDF, instead of 18 attachments that they go, they come out enough days ahead of time that people have time to read them and be thoughtful that you’re staring them not just through walls of numbers. But you know, here are the things to pay attention to, these are the topics I want to dig into. You know, if a board is your strategic asset, then you have to direct it to say this meeting, here are the three things I want to get out of it. I want to have a brainstorm session about this topic, I want to make a decision about that topic, I need an approval on this thing. And then set that stuff up in the materials so that you get you get what you need. Out of the board. It’s not about what they need.

And the last point, which is kind of related to that is, I’ve always found that when I kind of mesh together, my board operating rhythm and board operating system with my company and leadership team operating system, everything is much easier. So you know, if you put yourself in a position where you only have to do quarterly reporting once, and whatever you produce is good for your management team and good for your board. And it’s timely for both. That makes everything a lot easier. If you have your board meeting and your management off site synchronize whether you do them, you know, one two weeks before the other or the other way around. At least you kind of know your inputs and outputs like it’s kind of a consistent cycle where a lot of companies like they have their quarterly rhythm for running the business and their board meetings are on some other schedule. And they feel like they’re constantly redoing, reporting and thinking about what the issues are. So that’s just a way of making it easier on yourself. You just have to think whatever the board needs is what you need to run the business.

Allison: I’m just curious, is it the cart or the horse that goes in front? So does the leadership or management executive meeting go before the board meeting? Or is the board meeting before the executive management meeting?

Matt: I always I do leadership team first. Although I have done it the other way too. But I like the leadership team to be in sync on what we’re concerned with. out what we’re happy about what’s working, what’s not working, where could we use advice, and then have a board meeting. And I always have a leadership team debrief right after the board meeting.

Allison: So that it funnels Okay. With the lane changes or thoughts? Yeah. Okay, cool. That is some really helpful insights into. I know that many founders and businesses that have the at least the opportunity to have a board to a new way to think about it and to run it more effectively. So I appreciate that. That’s not what is the best way for listeners to find and or follow you.

Matt: I am pretty easy to find. My blog is My email address is I’m on LinkedIn. I’m on Twitter at Matt Blumberg. But blog and email are probably the easiest two things.

Allison: Okay, fantastic. I so appreciate the opportunity to speak with you today. Thank you so much for your time.

Matt: Good talking to you Allison. Thanks.

I'm Allison Dunn,

Your Business Executive Coach

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