Career Conversations with Benjamin Friedman

Janice Chaka [: 00:00:04

Hello, and welcome to another episode of the Traveling Introvert. This is Janice, and this is career conversation. I am here with Benjamin Friedman. Hi, Ben Benjamin.

Benjamin Friedman [: 00:00:15

Benjamin is great. Hi, Janice. How are you?

Janice Chaka [: 00:00:17

I'm good. Normally, I check that, and then I was like, do I wanna make the assumption? And no. I should not make the assumption. So thank you for joining me today. I really appreciate it. So the first question I ask everyone is, what does introversion mean to you?

Benjamin Friedman [: 00:00:35

So a great way to get us rolling here. For me, introversion means needing to be by myself In order to recharge and I think there are other variations to that, but I think that when I'm having a tough time, when I'm just feeling drained, when I'm feeling overwhelmed, I find that I typically need to be by myself maybe 15 minutes, maybe an hour, recollect my thoughts, and then I feel much better after that.

Janice Chaka [: 00:01:06

Alright. Thank you. And so what kind of tell us a little bit about the work that you do.

Benjamin Friedman [: 00:01:14

Sure. So I work with, start up founders. Typically, once they've attained product market fit or, service market fit, and they're on the path to scaling their business exponentially. That's their hope and mine. And so I help them to look holistically across the business To figure out where are the areas that need to be bolstered, either by people, by systems, by software. I talk with him about solutions that I've seen, risks that I've encountered in the past, and let's discuss some options and the best ways to move forward.

Janice Chaka [: 00:01:52

And so with that role and working with founders, at least you've got, like, a specific like, they have to reach here before I start working with them. Can you tell me about some misconceptions that people might have about your role and all your industry in general?

Benjamin Friedman [: 00:02:08

Sure. So I think one misconception is that I'm coming in with a toolkit that has exactly the right solutions they need. Instead, this is a discussion. My solution for the last company and for the prior 3 companies may be very different than what they need based on their Team, their stakeholders, their customers, their industry, and, certainly, the environment changes too. We've seen over the last 3 or 4 years several Complete shifts in in how we do work and how we engage business. So I have to come in and ask a lot of questions, Whereas I think sometimes their perception is I'm gonna come in with a bunch of solutions already in hand.

Janice Chaka [: 00:02:55

Yeah. Or the magic wand to fix everything with a short time period too.

Benjamin Friedman [: 00:02:59

Oh, of course. Yesterday at best.

Janice Chaka [: 00:03:03

And so mentioning that thinking about coming in and consulting. What are misconceptions what you mentioned that as a misconception the organization has, are there any misconceptions that individual people within the organization have about what you're coming in to do?

Benjamin Friedman [: 00:03:19

Sure. So I think I see that, at least 2 different ways. One is I often do not have industry expertise. I consider myself a consummate generalist, and I work across all industries. I'd like to think there are advantages to that. While I may not be a subject matter expert, I've seen how best practices work Across many different companies, I've seen how they've creatively solved problems, how they've effectively engaged their customers, again, across different industries. But I think people, when they first hear about me, they're like, oh, well, this person's coming in, but they don't really know us. They don't really know our space.

Benjamin Friedman [: 00:03:59

And then I think the second is, it's off it's sometimes difficult to understand my role, because I have a fractional role. It's not clear the hours I'm working, the responsibilities I'll have. Am I managing them? Are they managing me? And I think that's because a lot of people are born of a hierarchical structure and I understand. I get it. Especially if you've been in a large company, it's very clear, you know, everybody's Responsibilities, their tasks, what they're supposed to do, what they're not supposed to do, who they're supposed to go to for questions. And then I come in here with this holistic overview of okay. What's working well at this company? What needs to be better? I really wanna hear your opinions even if it's not exactly about the work you're doing today. But in general, you have a mind.

Benjamin Friedman [: 00:04:47

You have insights, and that's what I wanna hear, and I think that's, potentially, different. I was gonna say off putting. I don't know if that's the right word, but it's definitely different for a lot of people who are used to filling in their role Unless they come exactly from the start up space, and they're used to a ton of transition like myself.

Janice Chaka [: 00:05:08

While he was speaking, I was nodding. I was nodding a lot just because it's really common on how peep especially if and because fractional loads appear to be a new thing that people are starting to get used to, and they want set hours. Like, oh, no. I'm it's so many hours per week. Like, it kinda depends. I'm not gonna be I don't have office hours. Yeah. All all those things.

Janice Chaka [: 00:05:29

So have you always been in this sort of a role, or what led you to this kind of a role?

Benjamin Friedman [: 00:05:34

Sure. So I've been working with start ups around business operations and finance over 20 years. Up to 4 years ago, I was doing it as a full time employee. I'd be the head of finance, the head of operations, typically both, a start up wasn't ready to have separate positions, and I would come in, I would do a lot of work, lay foundation, Figure out what, needs to be done in those areas that I mentioned. And then after about 12 to 18 months, If I did a good job, you know, presumably things are calmer, we're ready to scale, and then there'd be an inflection point. That could be a fundraise. That could be some other event. Okay.

Benjamin Friedman [: 00:06:14

We'd have to pivot. We'd have to adjust, put in new systems. So there would be these, ups and downs in my journey, And about 3 years into most situations, they would go through an exit event of some kind, Acquisition, merger, management buyout. And they say, hey, Benjamin. Thanks for getting us here. Really appreciate it, and good luck in your next job. And I just assumed this was part of how life was in the start up world. So I was looking for yet another full time job about four and a half years ago, and I ran into a company that was looking for somebody on a part time basis.

Benjamin Friedman [: 00:06:51

And I said, I love what you're doing, but I'm looking for a full time role. And they're like, please, can you help? And I said, well, I can help as long as we're clear that if I find something full time, I'm probably gonna jump and do that. So I started working with them, and then somebody else reached out. And they were like, what are you doing? And I'm like, oh, I'm doing this part time gig. And they're like, well, we certainly can't hire you full time, but we'd love to have you come in and work with us. And that happened again and again. And and, Janice, before you know, I was working as a fractional COO. And it's just funny to me because I talk a lot with founders about really thinking about your plans and where do you wanna be in life, and yet, ironically, I ended up in my current situation through circumstance and good fortune.

Benjamin Friedman [: 00:07:34

So I am aware that there is luck involved, but also there should be planning.

Janice Chaka [: 00:07:41

That is so so Drew, that's a wonderful way of of getting into a role. And, yeah, especially for start ups, it's like, well, we we we know we need this, but we can't for this, how can we get this in a way that works for everybody? And so, honestly, fractional is the way to go. So with what you I'm gonna say that. With with what you've been doing, is there something that you've been doing consistently that has helped your business and career?

Benjamin Friedman [: 00:08:09

So one part of that is thinking strategically about where I want to be in life. I feel like for way too long in my career, I was very reactive, to my jobs, to my circumstances, to my family. And now I realized that I should spend 5% of my time on a weekly basis stepping back and thinking about where do I wanna be in the next few months, in the next few years? And this not only applies to business. And with business, I break it out, Sales, marketing, partnerships, infrastructure, but in my personal life as well. My family, my journeys, ways I wanna explore, ways I wanna have fun, really stepping back and thinking, how do I manage all this? And as an introvert, it means, leaving my family once a week. I I go to a restaurant with a bunch of notes, and I just lay them all out. And I'm like, okay. This is what I really wanted to do last week.

Benjamin Friedman [: 00:09:11

Am I making progress? So for the business, I have specific weekly milestones. For my personal life, it's a little bit, looser, but it's like, okay. I've talked about this trip for months now. This was the week that I'm actually gonna start making my 1st step in that direction. And so I essentially hold myself accountable, for business, it's more rigorous. For personal, it's more loose, but that's what I do. And then the 2nd part, I think, is being more forgiving as an introvert. I used to think, well, everybody's going to events in order to grow their business, so I have to go to events.

Benjamin Friedman [: 00:09:49

And when people go to events, I see they're talking with dozens of people. So I have to talk with dozens of people, and I have to jump into groups, Then I have to pretend like I'm really enjoying myself. And then finally, I realized, Janice, that, okay. This is not who I am genuinely. I do need to go to events. That's part of doing business. But it doesn't mean I have to talk to everybody. Once I talk to 1 or 2 people, I'm set.

Benjamin Friedman [: 00:10:15

I'm good. If I'm still feeling okay, I can stay longer. But if I feel like I've done enough, then that's okay as well. I come with a a set of open ended questions, things like, what are you excited about in the near future? What's been the best thing that's happened to you in the last few months? Questions that go beyond, you know, what do you think the weather will be like tomorrow, and and, you know, what brought you here in the 1st place? I mean, those are fine questions too, but I like to now just sorta dig right into something interesting. And if people respond, that's usually gonna be an exciting conversation. And if people, you know, answer, well, the weather tomorrow is supposed to be rainy when I ask, what are you most I'm excited about the rest of the year. Then I know that's probably not gonna be a good conversation, and I have to go excuse myself and get a drink pretty quickly. So I've tried to sort of be more aware of who I am coming into these engagements, and and that's events is one example.

Benjamin Friedman [: 00:11:12

But stepping back, it's being more mindful of who I am. How do I do what I have to do, but in a way that I'm more comfortable in doing?

Janice Chaka [: 00:11:22

Yeah, again, I was nodding my head. And so with the you mentioned with your family that you, you know, you take an afternoon or a day or a couple of hours and go to a a cafe, how did you negotiate if it was a negotiation, how did you go about introducing that practice into your life and have your family understand that it's not them.

Benjamin Friedman [: 00:11:44

So it's funny. I think it's a mix. I'd love to sit here and say, Janice, that I I had this conversation where I sat them down. I explained that I'm an introvert, And they all nodded their heads vigorously and said, yes. Of course. Do what you need to do to support yourself. But my family's with 1 of my daughters is more introverted. The other is a little more extroverted, and my wife is definitely an extrovert.

Benjamin Friedman [: 00:12:08

So I knew that even if I chose the write words very carefully as we introverts do. They're still not gonna necessarily understand in their heart. And so I would introduce it, and then I would follow it up, And I would come back again. When I would go out to dinner, I'd be sure to then come back and have conversations with the family or individually with everyone to catch up. So they don't think that it has anything to do with them. I'm here for them, but, also, I need to be here for myself. Occasionally, I do this, possibly radical thing, which is I take trips on my own. I go places for a week to explore.

Benjamin Friedman [: 00:12:46

It's absolutely lovely as an introvert. I have a great time. But, again, I know they don't fully understand, so I always try to come back with gifts, and I always try to, you really spend a lot of time with them when I get back. You know, what's been happening? What's going on? Of course, I take phone calls and all too while I'm away, But I really try to swing the pendulum even further and be a little more, social when I'm back to compensate for the time I was away. But at the end of the day, you know, this is what I need. And I I know the words can fall flat, but I I think they know from my Emotions before I travel and after before I go to dinner and after, I think they can sense that I am just more energized And more vibrant. And by the way, better to be around as well.

Janice Chaka [: 00:13:35

Yeah. It works out for everyone, people. So Yes. Is this something that you say no to?

Benjamin Friedman [: 00:13:43

So I think, where I say no, so I would put that in business and personal. So in business, I found that initially, as I'm starting my business, and you might have heard this a lot too, I was saying yes to everybody. Right? Oh, you need my help? Sure. No problem. Tell me tell me what you need later. I'm just happy to help you. And then I would dig more into the type of work they need, the deliverables they were expecting. And now I've gotten better at, Okay.

Benjamin Friedman [: 00:14:12

Tell me how you work with other people in the team. So sorry. Let me step back. So some of my values include optimism, Collaboration, learning. So I really wanna work with people who have Strong beliefs and their own passion, but they're also open to new ideas, and they're open to collaborating with others. I don't know if it's because of, I'm an introvert or just who in my DNA, I just get thrilled by a great collaboration Where I talk with somebody. I have an idea, probably not the best idea in the world, but they say, oh, let me take a piece of that idea and build on it. And I say, oh, that's great.

Benjamin Friedman [: 00:14:55

Here's what I've seen another company do. What if we did this instead? And we're building. So I wanna find that in people I work with. So I start to tease it out from the opening questions. I throw out things like, give me an example of somebody on the team came to you with a great idea, and you were willing to implement that. Give me an example of when you delegated responsibility to someone on the team and how did that go. Right? Because that's hopefully gonna give me a sense. And then once I'm in the door, I try to do some low level tests.

Benjamin Friedman [: 00:15:27

Like, for example, couple weeks in, I might say, hey. I wanna try out this new program. It's pretty low risk, but I just wanna see if it's gonna have a positive impact on the team. And if they're like, oh, of course, try it. Let me know how it works. That's a very different reaction than, well, let's talk about it some more. Well, let's bring in 5 people. You know, I have a committee discussion, and I'm like, oh my gosh.

Benjamin Friedman [: 00:15:50

Oh my gosh. And then the other part of saying no, I think, is, you know, with family, it's hard because I wanna please them. I wanna make sure everybody's happy. But I have realized that if I say yes all the time, then I become, grouchier and less pleasant, and I become resentful, quite frankly. And even if I don't use the words, it probably comes out in how I relate to them. So I try to get better at saying no, but can I do it later? Or no, but can you ask your mom for help? Or no, but, You know, is it something you can work on? And if you're still stuck, let's talk about it in a couple hours. So I I try not to make it a Complete rejection, but I do try to set boundaries a lot.

Janice Chaka [: 00:16:35

Yeah. Awesome. Thank you so very much. This has been so interesting. I have 1 final question for you. And it is, in your opinion, is a hot dog a sandwich?

Benjamin Friedman [: 00:16:52

Oh my gosh. Wow. You're this is, what is it called? The assault journalism now, like, you're I I feel like all the other questions are leading up to this controversy. Frankly, That's a good pun, actually. Frankly, I have no opinion. I a hot dog, it is something you eat if really there are no other options on the table, unless you're in Iceland, in which case, you have to try the hot dogs because somehow they're so much better In a country that has very few resources, they've made magic with a hot dog. That's my answer. I'm sticking with it.

Janice Chaka [: 00:17:32

I love that. Now I mean, I'm like, I would have thought Iceland for for, hot dogs because I was like, fish, but no. Okay. Go for the hot dogs. Thank you so very much. That is a great answer. Can you let everyone know, all the listeners, where they could find out a little bit more about you and the work that you do?

Benjamin Friedman [: 00:17:49

Sure. I'm happy to do that. The website is webuildscalegrow.com. Feel free to go there. I update my blog weekly. I also post on LinkedIn at Benjamin Friedman, and I had a book come out, late last year called Scale Reach Your Peak, And that book is available on Amazon in both paperback and Kindle format.

Janice Chaka [: 00:18:12

Thank you. Thank you so very much. Go get that book if you if you are at that stage where you are looking to scale, don't get it for for fun or, you know, even before you want to scale because it gives you ideas of probably of foundations or what you need to know that you're at that point. I know there's probably a lot of organizations like, well, we got a bunch of money, so let's scan this. Like, oh, but, oh, and stuff and things. Yeah. So thank you so much, Benjamin. I really appreciate it.

Janice Chaka [: 00:18:37

This is Janice at The Career Introvert helping you build your brand and get hired. Have a great rest of your week.