Be Curious and Invest in Yourself

Jeff Henningsen Lockton Companies

Jeff Henningsen has always been curious, creative, and committed to his goals. These are some of the traits that have allowed him to succeed in so many different realms. Jeff’s entrepreneurial career started with mowing lawns to make some extra money while he was still in school; this turned into a business that he was able to sell at the age of 22. After that, he gained experience in the private equity world before becoming the President of Lockton Companies in Texas, where he has worked for the past 26 years. Alongside his day job, Jeff is also the host of the Private Equity Fast Pitch podcast, which is about to reach its 100th episode! In our conversation today, Jeff and I discuss the value of coaching, the importance of finding your “why,” the benefits of being an introvert, and why doing is better than dreaming!

Key Points From This Episode

  • The key factor which differentiates “idea men” from successful entrepreneurs.
  • Why Jeff is so passionate about the value of coaching.
  • Jeff explains what motivated him to start his podcast. And the unexpected things that have come out of Jeff’s podcast.
  • The importance of committing to your goals.
  • Why Jeff thinks of himself as a (figurative) orchestra conductor.


[00:00:01] ANNOUNCER: Welcome to Branch Out, a Connection Builders podcast. Helping middle market professionals connect, grow, and excel in their careers. Through a series of conversations with leading professionals, we share stories and insights to take your career to the next level. A successful career begins with meaningful connections.

[00:00:20] AD: Hey, everyone. Welcome to the Branch Out podcast. I’m your host, Alex Drost. Today, I’m joined by Jeff Henningsen, President of Lockton Companies in Texas, focused on M&A Insurance Services. He’s also known as the podfather of private equity, through his work hosting Private Equity Fast Pitch, a top-rated private equity focused podcast. Jeff and I discussed entrepreneurship, the value of a curious mindset, why everyone should consider having a coach and much more. I hope you all enjoy.

[00:00:53] ANNOUNCER: Connect and grow your network. We are on LinkedIn. Search for Connection Builders.


[00:01:00] AD: Jeff, welcome to the Branch Out Podcast. Excited to have you here today.

[00:01:04] JH: Alex, I’m looking forward to it.

[00:01:05] AD: Jeff, why don’t we start with just sharing a little bit of your background to help our audience get to know you a little bit better.

[00:01:12] JH: I guess I’ll go back a little bit just because it gives you a good feel for my DNA. Grew up in Omaha, Nebraska, born in northwest Missouri, but I won’t go back that far. But when I was seven, we moved to Omaha, Nebraska. Grew up my entire life all the way through high school with two teachers as parents. Mom was the teacher that you didn’t want. She was a calculus trigonometry teacher with a master’s in mathematics. My dad was a coach teacher who used to show films of me playing league football in his business classes and all the kids I’m sure really liked that. He coached three sports: football, basketball and track. My mom was a volleyball coach. So I grew up as a gym rat.

I went to University of Missouri and when I was going to University of Missouri, my mom went back and achieved her master’s in engineering and doctorate in engineering, was recruited by the Air Force and we may get into that later, but spent 29 years with the Air Force, finishing her career as a three-star equivalent. Dad retired at 50, which is really awesome and grew up with an education family. I actually graduated with a marketing education degree from University of Missouri, and I was supposed to be a teacher/coach, because my parents were teachers. Basically, had to help pay for a lot of things, including some school. I mowed grass, and cleaned buildings, and did all kinds of different odd jobs. Found some passion in that and built a lawn mowing business that I sold to Kim Lawn when I was 22, right after I got married and decided to move to Texas. Accumulated some real estate and rented that to college students and found that I had a little bit of an entrepreneurial side.

When I moved to Texas, my father-in-law knew a private equity gentleman from Dallas, called Randy Best from Best Associates. I spent four years with him doing what most mid-20-year-olds do, which is anything Randy told me to do. I worked with a couple of his portfolio companies, rolled out a retail concept for him in one of those companies. Then in late ’94, he wanted me to move cities and work on a startup. I had already had a couple of kids and one on the way, third one on the way. Really just decided that it was time to look for my next step in my career and landed on the concept of going into insurance and serving folks like Randy. That’s what I’ve done for the last 26 years, is grown with the private equity world, which is now a legit industry. Back then it was a bunch of different high net worth people making investments.

[00:03:40] AD: You definitely have some entrepreneurial roots in you. I hear you were 22 when you sold your lawn mowing business, right?

[00:03:46] JH: Yes. Yeah.

[00:03:47] AD: Clearly you have some entrepreneur in you. You had some transactional deal experience. Then now, you find yourself in risk management. How does it all tie together for you?

[00:03:56] JH: It’s doing more of the same. I’m very curious. When I got into the insurance space, what I looked to do was provide value to my clients as they were buying companies, which I found to be very interesting and still do. There’s just so many ways that people make money and entrepreneurs have grown businesses. I was with a portfolio company client last week in Tennessee, and the gentleman started with two warehouses that were a record storage type business. Now, they’re the number three largest company of that nature in the industry behind Iron Mountain. It’s just amazing to see entrepreneurs build incredible businesses like that. We get to just serve a small piece of what they need when they buy these companies, performing diligence on insurance and benefits.

[00:04:42] AD: You were curious. You and I, we’ve talked a number of times before this and I’ve definitely picked that up from you. You’re a curious individual. You’re someone that wants to learn, to know, to constantly learn. Share a little more of your thoughts on that.

[00:04:54] JH: I don’t know when or how it started, maybe it’s just in my DNA, but I’ve always been the type to look deeper into things and always believe that no is not the answer, it’s just I didn’t ask the question the right way, maybe. I find myself not being really attracted to watching news, and TV shows as much as I am looking for cool videos or articles on various things relating to business. It seems like it’s something that I’ve been attracted to my entire life. When I take personality profile tests, which I’m a huge fan of, and I’ve taken almost anyone that you can imagine, I often land on a personality style that at rest is highly creative.

I was lead trumpet from seventh grade to my junior year in high school, played 17 years as a quarterback, did art, photography. I really leaned heavily on the, kind of, athletic and artistic side. But then at stress, I become very focused on dotting I’s and crossing T’s, which is a little bit of an unusual mix of a personality, I think.

[00:05:55] AD: The creativity, and this is always something I find interesting, when you talk about entrepreneurs and entrepreneurship as a whole, I believe that most people that are entrepreneurs really are hyper creative people, right? There’s an element of entrepreneurship that’s really about consistently being creative in finding a solution to challenges that exist out there. Being curious, being interested, but always looking for kind of a new out of the box way of doing something, I think is really the core of entrepreneurship. Would you agree with that?

[00:06:25] JH: I think it is. I think that one thing you have to measure that with or be cautious with is being an idea man. If you saw Night Shift with Michael Keaton, he was an idea man, but the execution might not have been always that great. I think that where you find, in my opinion, the truly highly successful entrepreneurs, who’ve been creative, but then figured out how to rinse, wash, and repeat and really create a process with the thing that they created, that’s where you see the success. You and I have seen throughout our career, tons of people who have an idea every week. The idea is the fun part, the execution is the hard part.

[00:07:01] AD: That is the truth. I’ll speak for myself personally, I’m an idea guy that likes to focus on execution, right? At the end of the day, you’re right, the ideas are fun, it’s fun to dream big and to think about all the different things you could do. But at the end of the day, the really good idea isn’t the first one that comes to mind. It’s usually that 10th derivative or iteration of the original idea, as you’ve beat it up through an execution kind of lens. Like, “How do I actually take that and go do something with that idea?”

[00:07:29] JH: You’re spot on. I mentor a lot of young folks and the problem many of them have is they come up with these grand ideas, and they spend months planning to execute rather than starting and then learning as they’re failing. That’s how they get better. I’d probably err on the side of taking risks and chances on new concepts or new ideas and eliminate them really quickly, or tweak them really quickly to become whatever they are as opposed to spending a lot of time dreaming.

[00:07:57] AD: You said something, I think that’s really important there. If you’re someone who has an idea that you want to test, go test it, go start with it, realize that the first time you do it, it doesn’t have to be perfect. Also understand that even if you think it’s perfect the first time doing it, ten times later, you’re going to realize the first time wasn’t all that good. You’re also the host of the podcast, and I think you have 90 some episodes out right now. You’ve been doing it for a while now, with a lot of experience in your belt. Think back to your approach to the first one and the second one and where you’re at today, 90 episodes later, is that maybe an example of somewhere where you’ve seen yourself, try something, learn, grow and keep evolving?

[00:08:34] JH: It is. That’s a great example. I’m posting it on May 26. I’m excited about this. It’s my 100th episode. It is a montage of advice to college students and young professionals that want to get into private equity investment banking. That was actually in my very first podcast. But going through the concept of starting a podcast, and I’ve had a lot of folks that I know call me about starting a podcast, and they rent studios. One person even actually built the studio to start podcasting. I started with a microphone, and a computer, and Libsyn and some basic things. I think my total spend was $100. I still haven’t spent any money on doing my podcast. I upgraded my computer, but I needed to do that for business anyway.

I called a bunch of friends and I said, “Hey! I’m thinking about doing a podcast. Would you be my guinea pig guest?” and I did it. Then I did number two, and number three, and number four and just kept going, and as you said, getting a little bit better. Learned my filler words that drove me crazy that I got to hear. Actually, that was an interesting opportunity to start hearing myself and understanding how I speak, which nobody ever gets real feedback from that. But it’s definitely been very interesting. Then learning how to market through LinkedIn and other strategies of what works, what doesn’t work. And at 100 episodes, that’s when I really feel like we’re actually getting some traction in the marketplace. The statistics that I saw recently somebody was doing some research on this, I think the average podcast does their last episode in the 20s. That’s about the longest people go.

[00:10:08] AD: I took a little bit of a different approach. I probably spent more money and equipment than I needed to when I first started. I got a good mic and I got a setup that, frankly, it’s still the one I use today, it works really well and I’m satisfied with it. But if I look back at the whole thing, where I probably spent more time than I needed to in the beginning and more money, was worrying about finding the perfect audio quality and finding that perfect way of doing things. As hard as I tried to make it perfect, there’s also part of me that will cringe if I go back and listen to those early episodes. Not because they’re bad necessarily, and certainly not because the guests were bad, but because I just realized how much more confident I am today, how much more I’ve learned, how much farther along I’ve come.

I think, obviously, we’re talking about it in the context of a podcast. But I think you can apply that to pretty much anything you do in life. What is experience? Experiences doing something, learning from it, being able to look back on it. You reference, being able to find your own filler words and hear your own self communicate, which is a great skill set that you can develop and learn from. But I think that goes with anything we do is that if we want to improve, we have to go do it to begin with, which means if we strive for perfection, it gets in the way of being able to do. I can assure you that 10, 20, 30, 50 reps of something will make you better than any level of planning for perfection ahead of time.

[00:11:31] JH: That’s spot on. Whether you’re going to be an airplane pilot or a professional golfer or anything, you can only study so much. At the end of the day, you gotta swing a club or fly a plane to actually feel how it’s going to be.


[00:11:43] ANNOUNCER: This is Branch Out, a Connection Builders podcast.


[00:11:51] AD: That really goes along with this idea that many of us want to grow and improve in some area of our life and we want to do something. If you don’t go out and do it, if you hold yourself up and keep telling yourself that, “Well, until I’m ready, until this is perfect, until it’s polished,” you don’t get anywhere and I’m a believer in the mantra that you just have to get something that’s good enough to move on, and do it and move on. Go out and try it and know that you’ll learn from it.

I want to dig back into something you said. You’re a big fan of personality tests. You and I have talked about this in a number of our previous conversations, that you are a lifelong learner, you believe in investing in yourself and in your own growth and development. You’d mentioned that you invested in coaching. I’d love just to get some of your general thoughts about that. Why is lifelong learning important? Why is professional development important to you? Then maybe share a little of what you’ve done to invest in yourself on that?

[00:12:40] JH: I think that my passion for coaching comes from playing athletics. When you look at – I reference pro-golfers, I went to a pro tournament the other day and before and after the round, the professional golfers are standing on the range with sometimes two, three coaches who are coaching them. These are the top 150 players in the world, still getting coaching every day, all year round. They’re not just getting swing coaching. They’re getting mental coaching. They’re getting diet coaching. They’re getting lifting coaching. If that is just one example of people at the top of their game, who are still getting coached? Why wouldn’t you do that in your professional world?

I think even in your personal world. I often have said, I wish that people would stop calling psychologists, psychologists because a lot of people in this world, marriages and parents need coaching, they don’t need psychologists. It turns a negative word into a positive word. I’ve just always been a believer that I’m never as good as I could be, and having third party help, observe, and listen, and give guidance can be a huge benefit in a very competitive world.

[00:13:51] AD: I want to dig into your view on coaching a little bit more here. But you said that you believe that you’re never as good as you can be. You believe there’s always room for improvement. I just think that’s a really important element to highlight, because I think if any of us want to grow, want to have that opportunity to continue improving ourselves, you have to have. It doesn’t mean you can’t be confident in yourself in your abilities and your skill sets. But it does mean that you have to step back and acknowledge that there’s always room for some kind of improvement and have a desire to want to continue to push yourself to that next level and achieve that next tier of performance, that next level of improvement.

If you don’t embrace that thought to begin with, then no level of coaching and investing is going to do anything. If you truly think, “Oh! I already know all that, I already know how to do it,” then there isn’t necessarily an opportunity for improvement. But if you embrace that mindset, which I hope we all do, I think it’s core to lifelong learning and continual growth and development. But investing in a coach, and I like how you say that there’s a lot of times that a psychologist or a therapist might be called a coach. I understand there are times where true therapists and psychologists can be very helpful in certain situations. But I agree with you that oftentimes in life, there is a need just to have a third party, someone else that can watch you from the outside. What have you seen as, kind of, the benefits of a coach, and like maybe without talking about – not coaching, but what does it do for you? What does that individual do for you as a person?

[00:15:16] JH: I think that a coach, and it could be a mentor, Lockton Series is Texas, Louisiana and Alabama that I’m part of. We have 46 salespeople, and I lead our monthly sales training there. It can be coaching, it can be mentoring, but you learn scenarios, plays to run, going with a sports analogy. In certain scenarios, role playing, coach can shortcut your steps to get some place or keep you from going down a path that is wasting time. There’s so many different things that a coach or mentor can bring to you, in guiding you, and keeping you out of that ditch and maybe getting a little bit closer to success.

[00:15:58] AD: I get asked what’s the value of a coach quite often. It’s hard to see what you’re doing when you’re in the middle of it, no matter what that is. Take the sports analogy. If I’m a pro golfer, I can assure you that the individual, the golfer that’s actually swinging the club is better at doing it than their coach, because that’s how the rules work. Just because that coach may not be quite as proficient or perfect at doing the actual art of swinging the club, their ability to stand on the outside, and watch you, and see things and notice things that you, being in the heat of the moment, being in the actual process of doing whatever it might be, just simply aren’t able to see.

I think that’s a lot of having that outside perspective and having someone that can help you see things. I think that applies in every element of life and business, it’s a great example, right? We can get stuck in our own ways of thinking and our own kind of prisms of what’s going on. Just having that outside point of view to ask you some questions, to help you see things differently. But then also, as you said, help you maybe see some of the traps that you might not see ahead, help you guide through it in a more effective and efficient way, and ultimately get to the next level, kind of a more expedited, but also cleaner path there at times. Does that align with some of your experience around coaching?

[00:17:15] JH: No, it absolutely does. The one thing we haven’t talked about is accountability. Coaches hold you accountable. I was talking to somebody at lunch today about this today, but I’ve always been attracted to coaching because I grew up getting coached. I don’t take coaching as a negative. Some people get yelled at by their coach, and they shrink up, and get scared. The reality is, a coach is not guiding you and coaching you unless they think you have potential. That’s the mindset that you need to take to that. But accountability is a big part of having a coach, and it’s just like having somebody help you with strength training or losing weight. Most people don’t have the ability to hold themselves accountable just by themselves. They need a coach, or a workout buddy or somebody to drive them. That’s the other value of a coach.

[00:18:00] AD: It’s a really good point. The accountability element, and accountability and self-discipline are oftentimes one and the same. I think many of us want to be disciplined enough to hold ourselves accountable to do what we say we’re going to do, but it’s always easier said than done. Life always gets in the way. Having even just a second set of eyes or an outside party just looking and saying, “Jeff, the last time we talked, you said you were going to do this. Did you do it?” It’s amazing how much accountability that actually creates, right? You can find that in a coach, there’s absolutely value in having a coach or mentor. But even just getting into an accountability group, even the workout example. There’s two or three of you that workout together every morning, it’s a lot harder to skip that workout, knowing that they’re going to be there as well waiting for you. That accountability goes a long way in actually achieving the results that you’re trying to achieve. Again, putting a plan together and saying, “Here’s what I want to do,” is easy, but actually doing it, the execution element of it comes down to the consistency and that accountability can make a huge difference in that.

[00:19:01] JH: And the other thing, the more you’re coached, the more you start to recognize something that you’re doing. When you’re a golfer, you recognize that you had your hand wrong, or whatever it maybe, because you’ve been coached so much and somebody points out, this is what you’ve done, in business or in your everyday life, as you said, pulling yourself accountable, life gets in the way. What you start to do as you learn tricks that you’ve picked up from coaches, on how to keep yourself accountable, how to recognize when you’re letting life get in the way and be able to plan your business strategy accordingly. Without a coach, you just are meandering around the path trying to do the best you can. But hopefully, as I said in the beginning, the goal of having a coach is to get better and be better at what you do.

[00:19:47] AD: I completely agree with that. You bring an additional level of awareness, and there’s a lot of value in just having that outside party looking in. To anyone listening, I highly recommend you thinking about coaching just for that simple reason. There’s so many different elements of your life today too that can be can be broken into. Let’s shift the conversation from it. I want to go back to the podcast. This is something you and I had chatted about before. Why do you do a podcast? What’s the value of it? Someone sitting on the outside saying, “Well, Jeff, you put a lot of work and a lot of time, and you’ve done a lot of these episodes. I’m sure it’s not easy. Why? What’s the reason for you?”

[00:20:19] JH: That’s a great question. The one that I asked everybody who calls me to say, “How do you do a podcast?” I always say, “What is your why?” People would be very surprised on what my why originally was, still is. I sponsored a happy hour in Texas for 19 years and in about year 16, I kept trying to figure out a way to kill it, but didn’t have anything to really put in its place. The real value of the happy hour, it was a happy hour that was run in Texas. On a Wednesday it was in Houston, and on a Thursday, it was in Dallas. We ran it in September, and in May, kind of a get back to work and then right before summer time period. It was marketed across the country to private equity firms that were calling on Texas. Basically, the message was, if you call on Texas, this is your opportunity to swing through Houston on a Wednesday, do your local calls, go to the happy hour that night, do the same thing in Dallas. Next day, you go home.

Well, that email was going out to about 2500 unique email addresses that I’d accumulated over many years. I didn’t want to lose that ability to be part of the ecosystem without irritating them, talking about insurance. It was a very much of a value add to the ecosystem that I was part of. I was trying to find something that I could replace the happy hour with and stumbled across, in late 2017, the idea of a podcast. Really, that was the main reason, I saw it as an opportunity where I could distribute really valuable content that people wanted to hear to my 2500 email addresses. Whatever happened from there was just icing on the cake. If somebody actually listened to it, icing on the cake. If somebody shared it on LinkedIn, that was even better. If one of my guests ended up becoming a client or was already a client, that was great. There’s been so many amazing things that have happened from doing the podcast, but it was really originally just to become and continue to perpetuate this feeling that I was part of the private equity ecosystem.

[00:22:19] AD: A way to create value added content, something to send out summaries. And the word content, especially in today’s day and age, is thrown around quite a bit. But it was really your opportunity to create a value-added recording of a conversation, content, a podcast, that you had a reason then to reach out to your contacts, the people that you’ve known from doing your happy hours, and continue building that relationship with them without just being the annoying guy trying to step in their inbox with nothing valuable to say and no reason to really reach out, right?

[00:22:50] JH: Spot on.

[00:22:51] AD: What benefits or value ads have you found that you didn’t expect? Now, you’ve been doing this for a number of years and 100 episodes almost. What didn’t you expect?

[00:23:00] JH: I didn’t expect to find out a lot of things about people that I have known for 20 years, 15, 20 years. Really cool things. One of my guests is an Arabian horse trainer that’s nationally known as one of the top Arabian horse trainers. Didn’t know that about him. Military experience. Just really cool things that a podcast discussion, as you said, just a discussion, but we dove into things that I didn’t know. What was really rewarding is, and I tell this to my guests, I’m giving them a product that I hope has a long shelf life for them. We spend a lot of time editing and I edited the first 60 podcasts myself. Part of my creative side, I think. I really enjoy it. But I wanted to have a product, and still do, that somebody’s proud of that they were part of and that they could use on their website, and distribute to their network and use it as an opportunity to potentially build new platforms that they could purchase or acquire through an investment bank. That was all a little bit surprising.

The other thing that I think was surprising, but very rewarding is, I get a ton of college students and young professionals that reach out and say, “Hey, Jeff. I’ve been listening to your podcast and it really helped me prepare for an interview. It helped me get an internship, even helped me get a job.” I have a fairly large pool of 20 somethings that are following the podcast and sometimes pinging me with questions about – one gentleman asked me to review a write up that he did for a job that he was applying for, which I happily did. It was very interesting, but very rewarding. I think that goes back to my teaching background, and education. The business side has now paid its fruit, has developed and I’m to a point where I’m super happy with where I am at Lockton. Now, at Lockton, I’m actually able to teach, and coach and mentor our younger associates and sales folks, but I’m also able to do that with some of my podcast listeners.


[00:25:02] ANNOUNCER: This is Branch Out, bringing you candid conversations with leading middle market professionals.


[00:25:10] AD: I hear a common theme of everything you’re saying is around adding value to others, looking for ways to add value to others. What you’ve been able to do is find an enjoyable, yet scalable way to add value to others, which is – it’s really neat. For anyone listening that’s thinking about a podcast, they’re a lot of work, there’s no doubt behind it. They can also be very value added and they can also be very fun. But to your point, Jeff, you’ve made it – you got to understand why you’re doing it. If you start off saying, “Well, I’m going to do this because I get a ton of downloads, and a ton of listens, and everyone’s going to know me, and I’m going to get a lot of business out of it,” you’re probably going into it with the wrong mindset. You’re probably looking at it the wrong way and recognizing that you have to have the right reason of why you’re doing it. To your point, most shows will fade out after 20. I fully understand that, right? When you first get going, it’s easy to, “Oh, I’ll do this, and this will be fun.” But then when you get farther along and you realize that you have to have a real reason driving you to keep you motivated doing it. I think that goes with anything in life, right?

[00:26:07] JH: No, absolutely. In fact, I live by a quote that I found recently, Jesse Itzler for those that don’t know, you got to Google him. But he said this quote on a podcast I was listening to. He said, “I don’t negotiate my goals.” I just live by that every day. If my podcast is supposed to go out on a Thursday, it is going out on a Thursday. There is absolutely nothing that’s going to stop it. Once you start something, I’m a pretty big believer that there needs to be a good reason why I’m stopping.

[00:26:35] AD: I’ll use my own experience around this and some of the podcasting. I’ll tell you, if I didn’t have a strong reason why I was doing it, and I didn’t have the discipline, the motivation to stick to what I started, I certainly would have dropped off somewhere in the 20th or 30th episode range. Not because I wasn’t enjoying it, not because performance ebbs and flows. We have a pretty strong following at this point. But there’s times where you’re like, “Wow! Did anyone even know I did this?” To the point of, if you don’t have the right motivation, and the ability and the willingness to say, “Hey! I’m not committing to trying 5, 10,15 episodes, but I’m committing to start a continuous podcast that I’m going to stick with.” If you don’t make that commitment, again, we’re talking about podcasts, but I think you can apply this to most things in life, you’re not going to get anywhere. You’re going to start and stop, and this goes back to having a vision, having an idea for something is great. But the execution, the long-term continual execution is really where you become successful in something. That all comes down to sticking with and driving yourself forward on that.

[00:27:31] JH: That’s exactly right.

[00:27:33] AD: You’d made a comment to me that you typically identify as an introvert, but yet you have done a phenomenal job at navigating in developing kind of a professional network across your industry, but also across the private equity across the country. That’s something that many folks who might be more introverted might find a challenge with. I would just love some of your thoughts and reactions to that.

[00:27:56] JH: It’s interesting, because I’ve always known I’m an introvert. My father was a really big talker. We would go to parties in the neighborhood or whatever and for the longest time, I actually thought I was a talker until I started really understanding that people would ask me questions and he would answer. What I learned to do as a young person in my teens was become a really, really proficient asker of good questions. I read somewhere and I don’t remember where, if you become really good at asking questions, you don’t have to talk much. It is absolutely true, and it is just so fun to go to parties, unless you’re talking to another introvert because then it becomes very painful, but if you’re talking to an extrovert, you don’t have to say much to wind them up and you can get really great information. Not for the purposes of getting great information, but just – they share so much.

I am a heavy introvert, but what I found is that, and I came up with this analogy recently, I really think of myself more as the orchestra conductor. The conductor typically has their back to the audience and they are highlighting the stars of the show, whether it’s the trumpet, or the drum, or the singer, or whatever it is, and calling for more noise, or less noise and creating a symphony that audiences enjoy. I really feel like as I’ve evaluated my life, that’s been what I’ve really enjoyed doing.

People talk about compensation. Compensation doesn’t have to be money. One of the greatest compensations I have is seeing people become successful. I had a salesperson on our team call me a couple of weeks ago on a Monday, and he had the most spectacular day you can have as a salesperson. Who can you call? Who can you brag to? I want them to brag to me and call me because it’s a safe place to do that. That just lit me up.

I mean, it just made me so happy. That type of thing, getting a Vanderbilt student who reached out and said that they’d reached out to seven of my podcast guests and talked to them, this is before they even talked to me, got an internship with one of them, and then he reached out to tell me about all this. I’m going to lean really hard into a kid like that, who’s showing that type of motivation. Now, he’s working at a large investment bank in Atlanta all on his own. He’s going to be very successful and I have tons of stories like that.

[00:30:19] AD: That’s so cool. Your point of asking questions, I think it’s something that oftentimes, especially folks that are newer to networking or business development might forget about the importance of that, or might not highlight that. You go into the conversation thinking about, “What am I going to say?” or “How am I going to talk to him? I don’t know what to say,” or thoughts like that, versus going in saying, “I want to be curious. I wonder what I can learn. I wonder what Jeff could tell me that I don’t already know.” Embracing that mindset of curiosity and that willingness to ask questions, I think, can make conversations easier for anyone. Regardless if you’re more extrovert in nature, it can still make the conversation feel more of a flow, kind of more of an engaging dialogue of asking questions.

But on the opposite end, if you’re more introverted, it does make it easier where you don’t necessarily have to be thinking of the exact thing to say or what to say next. You can ask a question and learn. The one key that I will say to anyone listening, if you’re asking questions, be genuine in what you’re doing. Don’t just ask the question, tune out and not listen to what they’re saying. If you want to ask, ask, listen, engage, continue to ask and you can learn a tremendous amount and build really good relationships that way.

[00:31:27] JH: That’s right. We refer to it as listening with intention to learn. I see so many extroverts, mostly extroverts who, their mind thinks very quickly, and they like to entertain and talk. You can see oftentimes in meetings, their lips are starting to say things while they’re waiting on somebody to finish whatever they’re saying. That means they’re not really listening to what that person is saying, letting silence – I say this all the time, let silence work for you. Nothing’s happening as fast as you think it is. Sometimes, a really nice pause actually allows the person to finish their thought and add some more. I find that being an introvert can be a secret weapon in a good way that you can really understand people and let them be who they are, rather than focusing on them hearing you.

[00:32:16] AD: I would echo everything you’re saying. I definitely identify more as an extrovert. I’ve gotten much better as I’ve matured in life, but I still find myself struggling at times to slow down enough to think, to not just want to jump out to kind of the next part of that conversation. But to anyone who does feel more introverted and identifies as more of an introvert, I believe that when it comes to business development, and really uncovering opportunities, especially in a B2B space, where it’s highly relationship dependent, I believe that oftentimes, introverts can actually be meaningfully better at it, because of their ability to thoughtfully listen and communicate, especially in smaller, more intimate type settings. I encourage anyone who may believe that that’s a challenge, to actually recognize that, oftentimes, that’s a pretty big asset when it comes to true relationship development.

[00:33:06] JH: I think it can be an asset, but to the whole topic of this conversation, you can get coached on how to be your opposite. There are many occasions where I need to act like an extrovert, and I do it and it wears me out. That’s where I think some people get fooled a little bit, that they think I’m an extrovert because I can stand up in front of 1000 people and talk on a stage, or entertain a group over a weekend, a bunch of clients. But the real definition of extroverts and introverts is what wears you out, and where do you get your energy? Most introverts get worn out in that type of scenario and need some downtime to recharge, where extroverts get more energy by being around people.

[00:33:46] AD: That comes back to knowing yourself, being aware of yourself and the coaching element of that, having someone that can help you see that, help you understand that. Ultimately, allows you to become greater aware of who you are as a person and how you function best, right? Which I think is a key element of truly being successful no matter who you are. No different from myself, as being more extroverted, is understanding that, understanding where I get my energy, understanding how I generally tend to interact with others. And as you learn that more, you are able to personally manage some of that thought process, and how you behave and how you react better in any social situation.

[00:34:24] JH: That’s right.

[00:34:25] AD: Jeff, I appreciate you coming on here. I want to ask one last question as we wind down. This is kind of your point of what I love about podcasting, you get to learn personal things about people. You mentioned your mother’s career in the Air Force.

[00:34:37] JH: That’s right.

[00:34:37] AD: I’d love to learn a little bit more about that.

[00:34:39] JH: I know at some point you’re going to give me an opportunity to share how to find me. For those that want to look at my LinkedIn, which is the easiest way to find me. You can find me at Jeff Henningsen and I’m with Lockton. I posted on International Women’s Day a post on my mother and comments on her career. What was just fascinating was the number of Air Force folks that found that post and commented about her, things that I didn’t know.

When she graduated from the University of Nebraska with her doctorate in engineering, SAC Air Force Base came calling on her. We made a family decision after several meetings that going to work for the Air Force was a good thing for somebody like her. If somebody was going to work for the Air Force and have the tasks and jobs that she was about to face, we wanted somebody like my mom working for the Air Force. She went into that in full force, and she ended up running all of the Air Force analytics group. There are awards named after her. Dr. Jacqueline Henningsen Analytics Award, that hangs on the Pentagon wall. They award that to the analyst of the year every year. Her retirement ceremony, and this is kind of funny, but my father being the extroverted talker, he brags on my mom a lot. He bragged on me a lot, too. He just is very proud of both of us. But he bragged so much that sometimes you discount what he says.

We are at my mother’s ceremony for her retirement, and there’s about 600 people under the Air Force Memorial in Washington, DC, just for her retirement. As the general starts talking about her and talks on and on for 45 minutes without a note, saying things that I’ve never even heard about her, my son who was 21 at the time leans over to me, he goes, “I think grandma is really kind of a big deal.” Anyway, if you want to see more of this story on her, go to my LinkedIn and look back on International Women’s Day, and you’ll see a story on her, and read it. It’s really cool what she was able to do.

[00:36:45] AD: Well, that’s awesome. Well, I appreciate you sharing that and I appreciate you coming on here. As you already mentioned, for our listeners, they can find you on LinkedIn. Where can they find your podcast?

[00:36:54] JH: The podcast, if you Google Private Equity Fast Pitch, you’ll be able to find it on pretty much any platform that you can imagine. It’s on your iPhone, it’s on Google, it’s also on, which is where that podcast is housed. You should be able to find it in any of those places.

[00:37:12] AD: Awesome. We’ll make sure that’s linked in the show notes below as well. I appreciate coming on here. I appreciate you sharing your thoughts and I look forward to talking to you again soon.

[00:37:20] JH: Alex, good luck to you. Really appreciate it. It’s been so fun watching your career thrive and I know you’re doing some great things with the folks you’re working with as well.

[00:37:28] AD: Thank you. I appreciate it.


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