Build relationships to solve business problems

Interview Summary

Helping People Think

00:00 Andrew shares how he introduces his work: not with a title, but through a flexible, relational approach to problem-solving. This sets the tone for a human-centered philosophy of entrepreneurship.

From Blast Culture to Authentic Connection

01:19 Andrew reflects on the shift from the early days of social media and performative networking to a more values-aligned, slower, and honest mode of relationship-building.

Designing a Business Without a Blueprint

11:05 He discusses how letting go of traditional consulting frameworks allowed him to build a bespoke, relationship-driven model—even if it meant making it up as he went along.

Why Vulnerability is a Superpower

18:34 A compelling dive into how showing uncertainty, asking questions, and embracing the unknown are vital to growth, connection, and sustainable leadership.

Prototyping Leadership

22:38 Andrew introduces his design thinking-based leadership model, built for helpers like nurses and social workers, offering a fresh and participatory way to define influence and direction.

The Joy of Social Connection

26:39 In the closing reflection, Andrew returns to the importance of human connection—at work and beyond—and how joy can be found in everyday relationships, not just outcomes.

Transcript

Andrew Benedict-Nelson:

We actually want it to fail so we can learn more. And that's a different way of relating to people. I mean, it's also a design technique, but saying, you and I'll do this with clients and it's always a little scary for me, right? To say, okay, we're going to do a small scale version that we want to learn from, you know, that we're going to do in kind of a slapdash way to figure it out. But that goes against, you know, the grain of, okay, I'm, you know, magic consultant dude and I have all the answers to all your problems. And I think that it does require that context of trust and shared curiosity. You can't be curious with somebody unless you have a certain degree of safety. And it takes some time to establish that.

Barrak Alzaid:

You're listening to Joy of Business, a collection of audio essays, timely discussions, and stories featured on digitalentrepreneur.com.

That was a clip from Andrew Benedict-Nelson—strategist, writer, and design-leadership coach working with nurses, social workers, and other helpers.

In our conversation, Andrew traces his path from blast-era networking to human-centered work, showing how vulnerability, repair, and slower relationships build better teams.

Keep listening to hear how he prototypes leadership with design thinking, what “helping people think” looks like in practice, and how connection restores joy in life and business.

Barrak Alzaid (00:00)

Hi Andrew and welcome to the joy of business.

Andrew Benedict-Nelson (00:02)

Hello.

Barrak Alzaid (00:03)

I'm so happy to have you here. I know that you've worked on so many meaningful projects over the years. Nowadays, when you meet somebody new, how do you typically describe what you do?

Andrew Benedict-Nelson (00:12)

Hey, sure. Well, it usually starts with some variation on I help people think about and what comes on the other side of that usually depends on the other person. If it's just a random person on an airplane, I'll probably say something like, you know, really tough, entrenched issues in their organizations or on difficult social issues because that kind of helps me tell my whole story. If it's somebody in I help nurses and other helping professions really realize the impact that they want to have with their work. And then my new one is I help people think differently about what kind of leader they want to be, which is what I'm kind of building out now. But it is always some version of I help people think. I don't think I deliver any product that isn't that on some level.

Barrak Alzaid (01:01)

Yeah, and I understand that helping people or people in the helper professions are a big part of your own personal identity and the relationships that are built around you. Can you tell me a little bit more about how you connect the dots.

Andrew Benedict-Nelson (01:19)

I've always been a healthcare person. You know, I just have never quite known how to make sense of it. I come from a healthcare family. My dad was a transplant surgeon. My mom was a pediatric nurse. And for a while I was going to work on the history of medicine. So everybody was in the field in one way or another. And I have siblings who are nurses and therapists and all that type of stuff. So we've got that bug.

But my career ended up taking a direction that kind of had nothing to do with that. when I started working with insight labs, which was an organization where we would, we would get together a group of intelligent, creative people to help organizations that were facing, existential challenges or, really entrenched social issues that they were working on. And so we'd bring together all these folks from a bunch of different fields.

To give them a new perspective to ask questions that maybe they weren't asking. And so that model and that kind of lifestyle, I mean, it was awesome. I got to meet people from all sorts of organizations all over the world and work on amazing problems, but it led to this way of being that was really kind of subject matter neutral. And what I talked about in my article is the sort of style of internet that existed at the time, the style of social media was also, I think of it as like very much about the blast, know, and putting out content that was guaranteed to get lots of likes and re-whatevers, depending on your reposts of various kinds. It was the happy days of social media, right? That we all still thought it was wonderful. And so I associate it with that time and with the network I built during that time. And so—

when my career started to change, when I was no longer with that organization or its successor organization and started working on my own, I still had this idea that I had to be, you know, kind of thinking out loud on the internet all the time. But it started to become really unsatisfying. And and at the same time, I think a lot of us started to really sour on social media. You know, I definitely quit Facebook over one of its various controversies and quit Twitter when Elon bought it. And so now I'm down to like LinkedIn and Mastodon.

Barrak Alzaid (03:28)

You talked about about Insight Labs being this kind of networking marvel. So obviously, you're setting the stage for us now and talking about at the time, what the social media landscape looked like as far as how you needed to build a presence. And you also had this direct personal experience being in these...live rooms or in these working experiences with InsideLabs. So what was it about InsideLabs that made it such a networking marvel?

Andrew Benedict-Nelson (03:55)

Sure. I cannot claim any credit for this design because I didn't come up with the model. My friend Jeff Leitner did. But I think that I helped make it real. And it was precisely because every time we delivered our product, we brought together new people. And some of them were people we knew, but a lot of times they were cold calls, cold invites, or people who we'd found through social media where we said, this person's interesting and they live in the city where we're going to do the next project, let's invite them. And so, that setting, it was kind of like the Olympics for creative thinking, I mean, people got to check out their colleagues at really the highest levels and do good with them. so bonds formed.

I mean, every which way in those rooms, but certainly everybody had a bond with us, the founders and facilitators of the group. And so, I don't want to be ungrateful for it because I think that it gave me the habit of networking. But I think that it also, because of the time, that we were in, I think everybody at the time was a little bit more transactional about their relationships I I think that we were all in that mode all the time. And so, I think that it was hard to disentangle a lot of the authentic connections that were happening from the kind of social media networking version. And I think that especially after I went out on my own, I felt confusion or disorientation over like, do I even know these people? Like, what should I be asking them for? What should I say I'm about? Without that original thing that created the network.

Barrak Alzaid (05:31)

So how are you able to find those authentic connections or build those more honest ways of relating to people? How did you avoid this sort of transactional approach?

Andrew Benedict-Nelson (05:44)

Yeah, well, I hope I am. I mean, I think it's something that we're all working on because we do, you know, I still have to sell, right? And so, you know, if you know me, you're going to hear about the stuff that I work on eventually, right? But but I think that I had a I had a need to seek out kind of deeper why behind those relationships and you know, but I can't, I can't claim that it was all a consciously designed process. you know, part of it was I was getting traction in, um, in healthcare already and social work and education. Those were very natural fields for me where I already had some subject matter expertise. but I was, what I think I needed to go through was a process internally of saying, it's okay for me to say these are my people.

It's okay to say this is who I'm looking for and these are the problems that I prefer in a sense. And I think that I was scared to do that before because I wanted to be all things to all people from a sales point of view, which isn't even wise, right? But it's where I thought I had to be and that I thought that I needed to be this external mysterious genius or something.

And I think that I'm much more comfortable now saying, no, nurses are my people, social workers are my people. You know, when I meet somebody, say, great, you know, I want to hear all about your nursing life or, you know, how your practice is going. so part of that was professional, but there's a personal side to it too, which was I was just going through a period where I was losing people left and right.

You know, my dad died, my father-in-law died, my stepfather died, my uncle died. I'm kind of all in succession there. And I think that it definitely prompts you to want to grow up a little bit and say, well, what am I all about? I think that I became, you know, it's funny with my dad because my dad was such a stereotypical surgeon. I never wanted to go into medicine.

I just never wanted to be that guy, the detached surgical type. But I think that it turned out I did want to be a healer of a kind and that that is a way of relating to people and of saying, okay, what are your problems and how can I help? And not necessarily needing to be the star, which, I think that I kind of left behind in the, the 2010s.

Barrak Alzaid (08:01)

–You did a lot of internal work to get to where you're at, especially with your focus on people in the helping professions. why did you feel like there was an opportunity with this particular group of people. Why did you feel like they were underserved and what did you feel like you were coming in to bring them?

Andrew Benedict-Nelson (08:23)

Sure, well, know, I think that I'm going to go through kind of the lens of leadership because it's been what's on my mind lately.

And I'll use the example of nurses. you most nurses, you either go into nursing with an associate's degree or a bachelor's degree these days and you practice, right? And you don't, there are a very small number of nurses who go straight into their master's or straight into their doctorate and thus straight into management or academia. But almost everybody has a kind of period of practice and most people never imagine themselves becoming managers or leaders, you know, they want to focus on patients. but there is a great need for managing and leadership within the field of nursing and for nurses to do within the field of healthcare. And almost nothing about how people are trained as leaders fits the way that nurses work. They, you know, it's a, it's a profession. It's not a business.

And the problems that they need to deal with are not even really like healthcare business problems. Like there are people who go and get MBAs in healthcare management and there's nothing wrong with that. But for a problem like, you know, how do you make our institution more welcoming to the community? There's really not, even in like the public health field, there isn't quite the right fit. So I think about those things a lot.

And one of the big problems I've been working on with a few of my clients is establishing healthy work environments. And that is a problem of leadership, right? You can't do that from a, you can't just spontaneously create a healthy work environment as a frontline nurse, right? There's always going to be an element of leadership. But so I would say that, you know, it was, it's a process of coming to understand what my role is in that.

And it is very much a role of support of, you know, looking at the people who are going to be the leaders because they're the one who has RN after their name, who has registered nurse after their name. And they have expertise I'm never going to have, you know, I can't run an IV line, right? I can't calculate how many nurses are needed on a shift, but I can look at the way that they think and say, okay, well, it looks like there's something that you're overlooking over here. And there's something I've noticed over here that might be able to be helpful for you.

And we can go through some known processes to make you as a better leader or a more creative person over here. And so I've gotten pretty comfortable with that type of support role or, I don't know, I kind of think of it as like a collaborative role.

Barrak Alzaid (10:43)

Within that way of working, it sounded like you're also really refining the services and the approach. And I just would love to hear more about how you've learned to apply your particular skills, your particular knowledge, your particular interests in managing your own digital first business.

Andrew Benedict-Nelson (11:05)

Let me tell you what I'm really bad at first. I, there is a process, of developing a consistent consulting offering that is out there in the world that I have just never been very good at. And it's related to everything that we just talked about because, you know, I just don't have a model where I can say, oh yeah, I'm going to increase your KPIs. I'm going to increase your clicks or whatever it would be. It doesn't fit. So it is very much more about developing those relationships with the principles of the organization and their needs. It's funny because I just went through a process with a friend of applying for some grants and I just never worked through grants before, not grants, sorry, through RFPs from some national organizations and who knows, maybe we'll get it. But I said, you know, I don't normally work this way. And she was saying, well, how do you work? How do you get work at all if you're not working through RFPs? And I said, well, a lot of times it's just meeting the people in charge and asking what's really bothering them. so on the one hand, that has gotten me some great work that lasted for years.

And on the other hand, it is very kind of, I don't want to say it's haphazard. I think it's pretty methodical, but it's, everything's kind of a one-off. And, you know, normally I will kind of weave together a story of how what I think the organization ought to do relates to other things that I've done or other work that they may have experienced. And that's, that's the best I can manage with it.

Now, with individuals' experiences, I'm a little bit better. And this comes from being a coach and being a teacher of saying, OK, here's where you're at, and here's where you're going to end up. And that's going to happen through a series of interactions with me and with other people who we might involve in the project. I'm much better in that sort of experience design.

And what I'm doing in leadership currently fits that because it's literally taking them through a design thinking process, but focusing on them as a leader who we're going to redesign, who we're going to take their core traits as a leader and switch out some of them in a way that they may need to do that gives them a kind of map for their own personal change and development and gives them some projects that they can try. So yeah, I'm a lot more comfortable with that. I honestly wish that I

I did know more about how to sell consulting or how to sell projects. But I don't know. I've also found that when I'm stuck, I remember when I had just left graduate school.

I was applying for jobs that honestly just made very little sense, but they were entry level jobs. were, you I just wanted a job at the time and I wasn't getting anything. And I look back and I'm just like, I'm so lucky that I didn't get any of those jobs because if I had, wouldn't have ended up in this other way.

And I think that that's true of a lot of us who live this kind of life where we just say, you know what, actually I sucked at PowerPoint. So I learned to do magic, and that's kind of how I feel about myself. I'll go into the slides if I have to, but I would much rather, send everybody back to kindergarten and do some interactive exercises and that sort of thing.

Barrak Alzaid (14:08)

I love that. I think we all need a lot more play in our work and real lives. And I think...

Andrew Benedict-Nelson (14:14)

Yeah, well, know, it's funny, people used to kind of poke fun at me for it, but I say it's not because I want to be in kindergarten. mean, you know, not my favorite grade out of the ones I experienced. But I do think it is just the most effective approach most of the time to set up those types of interaction for learning and creativity.

Barrak Alzaid (14:32)

And I think that there are a lot of other entrepreneurs who, similar to yourself, don't have a particular framework or model. There's not a boilerplate or blueprint that really matches what they're doing or what they're trying to do. And a lot of them are trying to figure it out as they go. And it can be really challenging. So do you have any advice for people as far as how to find your own way.

Andrew Benedict-Nelson (14:55)

Yeah, I struggled with this problem for a decade or more. And I will tell you that having had actual methodologies and approaches that I developed with people or that I wrote down and methodically worked out doesn't necessarily help with the sales piece or even just the explaining what you do piece because that's its own problem. But I do think that the starting point for solving the problem and what has worked for me has always just been story, know, and narrative of explaining, okay, here is some work that I did, here's how I think about it and where I think it could go. And I think that, you know, the next chapter of that story could be you. I don't know that it's the most efficient way.

It's not a sales page, but I do think it fits the problem that you're describing, which is that actually methods and patentable approaches... I don't want to say they're not real. I teach this stuff. I do this stuff with people, but I think that they sit on top of, to me, what is the fundamental, which is the relationship and creating that trust with the client and creating that feeling of, know, we can go somewhere together. And, you know, just being able to talk about Six Sigma or whatever, that's, you know, that's just one tool in the toolbox. And, you know, what you really need is the mechanic.

Barrak Alzaid (16:22)

I really love that analogy. You know, speaking of retooling or reworking how we do things, you've also said that we're in a time when we all need to relearn slower and more traditional ways of relating to each other. So I feel like this idea of storytelling and how you tell your story and doing it in a non-scalable way is one major component.

But what else do you think we need to adjust in order to move slower and change the way that we relate to each other?

Andrew Benedict-Nelson (16:53)

Well, so this is not an answer I expected to give, but it's the first thing that occurred to me, and so I'll unpack it, which is repair. a lot of times clients will talk to me about problems in relationships or ruptures of, you just conflicts, right? They're not necessarily problems or conflicts between organizations or debate over issues. And I don't know what it is about me that I've always kind of leaned into that rather than lean away. But I think that it's not just because I like arguments or whatever. I think that honestly, if you're going to build relationships, you need to have problems in them and you need to know that you can work through problems with people. And so it's actually an opportunity.

When those problems occur. And I think that that's something I even sort of talk about in my current work with prototyping of, know, uh-oh, there was a misunderstanding with a client. Well, actually fixing that misunderstanding could be more important to the client relationship than the initial landing the client. It's not a completely negative thing that is happening. But I think that to get to the point where you're talking about repair, in relationships, you've got to already be a lot more vulnerable than we are most of the time. And you've got to be honest too. You can't hide that something went wrong. And unfortunately, it goes against the grain of a lot of where we are right now as a culture. You have to forgive, right? And I don't know that we're a forgiving culture. So I mean, I don't have any answers to the sort of civilizational problem, but it's the stuff that I try to practice.

Barrak Alzaid (18:25)

Can you say a little bit more about how we need to get vulnerable and how we need to express that vulnerability in order to be successful entrepreneurs?

Andrew Benedict-Nelson (18:34)

So I think that just as a basic way of relating to other people, asking questions and talking about what you don't know about, what you need to learn more about, I think it provides a kind of ready-made opportunity to do that. And I talk about that in my work a lot with prototyping, that you need to get out there and say, okay, this project is going to fail.

We actually want it to fail so we can learn more. And that's a different way of relating to people. I mean, it's also a design technique, but saying, you and I'll do this with clients and it's always a little scary for me, right? To say, okay, we're going to do a small scale version that we want to learn from, you know, that we're going to do in kind of a slapdash way to figure it out. But that goes against, you know, the grain of, okay, I'm, you know, magic consultant dude and I have all the answers to all your problems. And I think that it does require that context of trust and shared curiosity. You can't be curious with somebody unless you have a certain degree of safety. And it takes some time to establish that.

Barrak Alzaid (19:34)

And it's interesting to think about also what you were discussing regarding having a conflict with a client and repairing the problem, because that's an intense moment of vulnerability when as an entrepreneur, your immediate reaction might be to get on the defensive or to over explain or over correct. And so what would be a vulnerable, but, you know, successful way of doing that kind of repair.

Andrew Benedict-Nelson (19:59)

I would say, you know, my instinct as a whatever I am, provider consultant, person who sends bills is, is to be like sycophantic, right? Is to go way the opposite, not to be defensive and be like, okay, well I, you know, I can provide you 12 times as much as I was before, which is not the right thing to do, right? That you'll burn yourself out that way. and it's not what they want anyway.

I think it always starts with a kind of grounding conversation that is open, where you don't know what the end of the conversation is going to be. And maybe they do, right? I mean, if somebody is determined to reach a certain result, then, but most of the time when problems happen, I find people are just kind of confused. They may not have been paying attention. They may say, wait, is this how this was supposed to go?

I don't think that many people are sitting around waiting to trap other people or call them out.

And if they are, then the relationship is not worth having anyway. I was driving my son to school this morning we were talking about hitting and pushing at school, which is a thing that they go. He's in preschool. Right. So they're going through that phase right now. And he says, well, what if a bully shows up? and I say to him, well, everybody can be a bully.

I'm trying to explain that there isn't this group of bullies that is out to get him at school, right? It's just the other kids. It's just his other friends. And I think that that's true for almost all of our relationships where most people are not out to get you. Social media may be an exception where the trolls show up. But I think that, yeah, it doesn't make sense to go into defensive mode most of the time with clients, even if you do have a lot to defend. I totally empathize with it.

I totally empathize with, no, what if our contract is canceled? Or what if they hate me? What if they don't want to renew? But I think that people should know, especially if you're in your first big one, that creating that kind of authenticity and saying, let's talk about what happened is going to do you much better in the long run than trying to defend the terms of some contract or something technical like that.

Barrak Alzaid (22:04)

That makes a lot of sense. I think we, again, going back to childhood, whether it's playing kindergarten or lessons about bullying, think those instances are pretty universal.

One of the things that you've been referring to throughout our conversation is this shift into design leadership. And it seems to be a really big part of how you're thinking about your work and what you're doing right now. So I was wondering if we could just zoom in a little bit on this and if you could just kind of break down exactly, you know, how did you arrive at the shift that you're in right now and what are you, yeah, what are you exploring?

Andrew Benedict-Nelson (22:38)

Yeah, well I felt like this thing happened to me, you know, almost involuntarily because, um, cause you know, if, if you had asked me what I work with people on, you know, a year ago, five years ago, I never would have said leadership, right? I wouldn't have said management. would have said something like strategy or creativity, exploration, research, right? But that the stuff that you get an MBA for, I would be like, I'm going to stay a million miles away from that because there's so many people who are out there who are expert in it.

But what happened was, did have a long-term kind of dissatisfaction with what I would actually call leadership in some of the fields that I work in, not management, leadership of motivating people and finding direction for organizations. And I was in a meeting with a group of people one day thinking about how to work on this problem in healthcare. And it just kind of struck me all of the out of nowhere that the design thinking process that folks use to create products and create services or create, you know, even organizations and industries could be used as a personal leadership development process.

It's design thinking, there's lots of models for it, but the most common model you go through empathy with your users, then problem definition, ideation, and then prototyping and testing. And so in this case, the users are the people to be led by the leader, which I would consider anyone who they need to do something who they wouldn't just do automatically on their own. So, you know, someone who requires some type of intervention to move into action. And so we define those groups and we look at their emotional needs, their motivations, and then we use those to develop, okay, here is the type of leader who is needed for this situation. And so it's totally throwing out the playbook on traditional leadership in my mind, which I think has, is focused on a small number of kind of inborn characteristics of, you know, confidence and that type of thing. You know, I mean, having a loud voice, literally, you know, was a quality of leadership in ancient times.

And instead looks at a much more flexible approach of, these people need, know, one that I hear a lot is people are looking for opportunities for advancement or opportunities to further develop themselves. I think that's a major shift with millennial and Gen Z employment, that they're looking for that from their leaders. And I think a lot of people have no idea how to provide that or think that that's something that the other side should be responsible for.

And so integrating that into projects and how you lead and how you design projects is a thing that you can do, right? But instead of doing it as kind of management advice, I work with folks on, okay, if this is a design principle that everybody's going to learn from your next project, how might we go about creating it? And how could that be a way that you exercise leadership? So that's just one example, but what I'm currently building out is the business model.

around that, which I think is just going to continue to be one-on-one coaching. But I'm building out who needs this and when and why. I think it's mostly folks who are in some new situation or have a new team, a new project and want a way to stop and say, who do need to be in this situation? Because who I've been before isn't going to work. And I think that's going to be more and more people as our work lives get more flexible and people have roles that are not necessarily the same over time. So I'm excited about it and honestly a little scared because I feel like I've found this power cell for the gigantic problem of leadership and I'm not quite sure what to do with it. But for now my plan is help my nurses and help my social workers and help folks who I already have those bonds with on a problem I think everybody has.

Barrak Alzaid (26:15)

It's really fantastic and I really applaud you for continuing to push yourself and push the kind of impact that you want to have, that you want to make with this really important group of people. I've got one last question for you. At digital entrepreneur, we're really big on reconnecting entrepreneurs with the joy of business. So when things get hard, what helps you get back to feeling joy in life and in business?

Andrew Benedict-Nelson (26:39)

Well, I would say for me it is people. it really goes back to all the things that we've been talking about. Because I know that when I get, when my thoughts get tangled or when I feel like I'm really stuck, I need to go and re-experience people outside of the context of what I'm doing. It's funny, I read this book, of course I can't remember the title, but it was by the former surgeon general under Obama and Biden, who's just a fantastic guy, and it was a book about social connection and it literally came out like a couple of weeks before the pandemic started. So it was a very interesting time to have a book about that out.

But he was talking about that the sociologists say we've got kind of three kinds of connections. We've got our most intimate connections, our friends and family. And then we have this sort of general social connection with like all human beings, right? The feeling that you get when you're walking down the street and see people who you don't know. And then you've got your sort of, you're like crew, right? You're people who you see at work and people who you see at school and.

who might not be your best friends, right? But they're part of your kind of cast of characters. we need all three. That's what's so interesting about it is we don't just need our best friends, right? We need for our psychological wellbeing, we need all those types of interactions. And I know that I tend to get way too caught up in one at a time, right? I'll be like, okay, I need to, and it can just be cabin fever from being a parent sometimes, right? Where I'm just like, I'm staring at my wife and my kids all day and I need to go out to a coffee shop and just hear people talk about nothing. But I think that it also applies in a professional context where I have work folks where we'll schedule Zoom time to talk about severance or talk about Dungeons and Dragons. And it's part of maintaining those relationships, but it's also healthy for you in your in your socialization and your sense of self. And we used to do this stuff, right? This is not a strange thing to do. It's just adapting it to life, you know, from your laptop at your desk. And so I think that we all, we all need stuff like that. And I, and I need it too, right? I'm, I feel like very much an amateur in that type of socialization. And I'm always looking for new things where I can say, okay, that's a good way to connect to people and, and learn something and you know, not be logging hours for work necessarily.

Barrak Alzaid (29:15)

Well, thank you, Andrew. It's really a great reminder again to continue to find that balance between work and life. And sometimes you don't have to separate it so much as, you know, find the joy in the work, that joy in the everyday encounter. So thank you so much, Andrew. It was such a pleasure chatting with you and learning from you today.

Andrew Benedict-Nelson (29:37)

All right, and thanks to you and for all the folks who make this community. It's a really great place to hang out.