Are You A Great Manager? Learn From 6 Best Management Experiences


This is a special episode focused on what makes a great manager. I am fortunate to have talked with six people who shared their stories with me. Can you relate? Please share your stories on the BreakTogether Facebook page. 

Thank you to the following rock stars I am lucky enough to share home base with, in Portland, Maine.  Their contact information is below along with our conversations:

Dan Sexton, Owner, Horizon Digital Marketing (

Lauren Reid, Co-Manager, Cloudport Maine, Portland (

Eli Dolloff, Owner, Maine Marketing (

Gretchen Johnson, Director of Marketing, Verrill Dana (

Laura Sprinkle, Creative Launch Strategist (

Adrian Espinoza, Engineer and SEO Agent, (

ERH:   Today is a special episode. I’m interviewing six people with completely different work experiences, who share stories about positive managers or work cultures in their careers that have shaped who they are today. Here’s our first guest.

I am here with Dan Sexton. He is the owner of Horizon Digital Marketing. Dan is going to share his story on either a great culture that he has worked in or a manager that he worked with and why. Dan, welcome and thank you for joining.

Dan Sexton:   Thanks, Liz. It’s great to be here this morning.

ERH:   What is your experience, Dan? I’m looking forward to hearing about it.

Dan Sexton:   I had the good fortune of working for the online division of a newspaper early in the transition from print to web when it was very new. One might say that we didn’t have any road map, but at that time, there wasn’t much of a road either. We had to create it from scratch.

It was a great experience because the company had made a real commitment that we’re going to do this web thing. They made a commitment with resources and money; and they made a great decision in hiring an excellent president who set the culture of the organization. The reason that it was so successful in being innovative, is that he truly respected people and encouraged us to try new things. I think what drove it is that he was also open to people trying new things and, frankly, failing. He even created a prize. We’d meet once a month and there was a prize for the biggest failure.

ERH:   That’s beautiful. I’m reading a lot about that right now actually.

Dan Sexton:   We would meet at breakfast over bagels, and people talked about their biggest flop. It created a culture that “Hey, no one’s really done this before; we’ll just give it a shot and do our best.” Half of them failed and half of them worked. It all came from the fact that he was open to people giving it a whirl.

ERH:   Was there anything else about what he taught or that you took from the experience, that you even use today?

Dan Sexton:   Good question. There is, and that is I’m looking back at these 17 years, and I had no idea how rapidly technology would continue to evolve. It’s like a freight train that’s moving even faster every week. For me personally, I really got used to the idea that it’s going to be different next week and that some of the things I’m going to try are going to fail, and that’s okay. Easier said than done when you’re the boss.

ERH:  Right…That is a beautiful lesson. Sometimes just being allowed to fail and being encouraged to do that has us trying things we would have never tried before. I appreciate that lesson.

Dan Sexton:   Yes, it’s a hard thing to overcome when we live in perfectionism, and not making mistakes is ingrained in our culture. Tough thing to get over, but well worth the effort.

ERH:   Thank you, Dan, for that lesson. Thank you for sharing it today.

Dan Sexton:   Thank you.

ERH:   My next guest is Lauren Reid. She is a space manager at Cloudport Maine, which is a co-working multi-space in Portland.  Welcome, Lauren.

Lauren Reid:   Thank you. Happy to be here.

ERH:   So glad to have you.  Please share with us, what is one of the best working management situations that you’ve experienced and why was that?

Lauren Reid:   Yeah. I’ve had to think of a few since I’ve had a few jobs, but I fall back on my experiences growing up and working at DiMillo’s on the Water, the floating restaurant that is so well known in Portland, Maine.  I work there in the summers. I started out as a busgirl at 16 years old (…I’m 33 now) and made my way through the ranks and really enjoyed bartending and waiting tables. My manager for the dining room was a man named Fern Cyr.  I have to admit that working at any other restaurant along my way through college and beyond, I always compared it to working for him. He had awesome techniques to keep us in line and keep us on our toes, keep us inspired, and feeling professional with some of the practices he put into our shifts there.

We were held accountable, so it really put a fire under your butt, if I can say that, in the best possible way. You were required to know the whole menu and to know what you are talking about. You are a professional server. He would have fun games for us in this meeting, whether it was a scratch ticket or a free lunch. He would ask trivia questions either about our menu items or the name of the boat in the picture frame down the passage way. It encouraged us to know every single detail about the business in every way possible and to pay attention. We were rewarded for that on top of having the opportunity to make money at a great business in Portland. It was more of a bonus and it just lit us up a little bit; you could see why he did it. It was really effective.

ERH:   What do you take from that experience into the new professional roles that you have?

Lauren Reid:   Now, being in management in a couple of different spaces, here at Cloudport, I think of him all the time because it’s so important to find the balance of being respected as a professional while managing a staff underneath you. Have their respect, encourage them, but also say good job. When they go above and beyond their job duties, make sure you recognize that, not doing it too much but letting them feel like they’ve earned it and then giving them opportunities to earn even more.

I think that keeps the fire in the belly a little bit more than a place that doesn’t do that, and helps that person connect to their manager and respect them.   Develop a good relationship [with your staff] that goes further than just the Xs and Os of being managed.

ERH:  That is excellent. I love that story, Lauren. Thank you so much for sharing it.

Lauren Reid:  Thank you, of course.

ERH:    I am here now with Eli Dolloff. He is the owner of Maine Marketing and BitRoot. Eli is going to talk to us about one of his most memorable work cultures or managers and why. Why are they the most memorable to you?

Eli Dolloff:   Thank you.  Well, I worked for a marketing company, they do everything from small websites to apps, and marketing. It was a great place to work because they had the kind of ecosystem where if you wanted to build something on your own, the managers would look it over, approve it and say, “Hey, this is a viable thing to go out and build, we think you can make money off it.” They let you be really creative versus a company that’s not willing to change or [provide those freedoms]. That was a huge thing.

ERH:   What about that experience do you take into your work today as a business owner?

Eli Dolloff:   As you know, with software development and marketing, it gave me an open mind to go out and try new things, test the market and come back and see if they worked and if they did, pursue them.

ERH:  That’s a great example. Thank you so much, Eli.

Eli Dolloff:   You’re welcome.

ERH:   My next guest is Gretchen Johnson. She is the marketing director at Verrill Dana here in Portland, Maine and other locations. I’m very excited to have Gretchen here to talk about a manager or cultural work influence, that you still think about today and why.  I’m going to turn it over to you, Gretchen.

Gretchen Johnson:   Thanks for having me today, Elizabeth. This is really fun to have a chance to talk to you about this. As a manager, I think it’s really interesting to explore what memories and experiences stand out for other people in strong management. As I thought about this question, I went way back in my life to when I grew up on Cape Cod and I worked in a restaurant. The restaurant industry at Cape Cod is extremely busy in the summers, it’s thriving and very high pressure, as most restaurants are in the industry in general.

I was about 16 or 17 years old working at a restaurant at a golf course, and the boss there was a very intense person. He was volatile, he was difficult. He was the kind of person who throw plates and pans in the kitchen. Not the kind of person you wanted to cross and not necessarily … That’s not what made him a good boss.

The story I have for you today is that at 16 or 17, I was new to the workplace, new to this kind of environment, and I was working as a hostess. One day he came to me and said “You’re doing a great job as the hostess, but I really think there’s more you could be doing. I see potential for more responsibility. If you’re interested and up for it, I would like to put you in the position as a manager when you’re working,” which was a lot more responsibility.

It meant that at 16, 17 years old, I would be responsible for the staff on the floor at the time, scheduling out the staff. I was responsible for the drop at the end of the night, the money, balancing it all out, making sure that what we thought he had in the receipts is what we actually had in the drawer, locking up at the end of the night, last one there, closing up. I didn’t even have my driver’s license at the time, so after doing all of that, I would head home on my scooter.

ERH:  That’s a great story.

Gretchen Johnson:   I just remember feeling so encouraged by his recognizing in me those abilities that I didn’t even see in myself. I didn’t ask for it. I wasn’t trying to get that position. I was just doing my job the best I could, and he was able to pluck me up and give me opportunity that really elevated my game and made me more passionate about the work I was doing, and excited to do the best I could.

ERH:  That is a powerful story. See? It’s so important to give people opportunity and to recognize when someone might have potential. I think sometimes the easy thing to do is to just let that person work and be good at what they do, but it was brave on both parts to take that chance.

Gretchen Johnson:   Yeah. It’s a leap of faith. It was nice to know that my work was recognized without me having to say, “Look at me, look at me.”

ERH:  How do you see that impacting your life today?

Gretchen Johnson:   I think in my work, supervising my team, I try to find those moments where someone is doing something great and use it as an opportunity to advocate for them. I always say that I want to work with people who want my job, just not tomorrow.

ERH:   That’s good.

Gretchen Johnson:   Mentoring the team and making sure that they have opportunities where they can shine, where I can just step back and let them do their job the best way that they can so that they can demonstrate their value to the people around us.

ERH:   Excellent lesson, Gretchen. Thank you for joining me.

Gretchen Johnson:   Thank you, Elizabeth.

ERH:   My next guest is Laura Sprinkle. She is the owner of Soul Fire Revolution. Welcome, Laura.

Laura Sprinkle:   Thank you!

ERH:   I am excited to hear about a management or a work culture experience that you have that you consider very positive and why. So take it away.

Laura Sprinkle:   Sure, well, I ended up working at Whole Foods for not very long, but I attended two days of orientation and then I had a couple of shifts before I got a little too busy. I loved it because they really take care of their employees. You would think like, “Oh, I’m just bagging groceries, but, no.” They really care from the bottom person to the top.” They call everyone team members, which I just love, and they have a culture where they ask, “What role is going to make you happy, how can we support you in your learning journey, in your life journey.” It’s very different. The fact that we had two days of training and then I was just going to be a cashier was incredible. A lot of training, I really appreciated. A lot of support. You could just tell that they care about their employees.

ERH: That’s great. Now that you’re a business owner, which is what I’m guessing had you too busy to stay; how does that impact what you’re doing today?

Laura Sprinkle:   Yes. It makes me think about the hiring process. I’m hiring people on my team I think about what I’m going to do with them. I actually had a 2- hour orientation with new team members because it really helps to show them the values of my company, review expectations, and the projects we’re working on, how much do they cost. Even if they’re not involved in that specific aspect of the project, for them to have an overview and know the information is so valuable.

ERH:  That is an excellent takeaway.

Laura Sprinkle:  Yeah.

ERH:  Thank you so much for sharing, Laura.

Laura Sprinkle:   Thank you.

ERH:  The last interview today is with Adrian Espinoza. He is a chef apprentice and has a wonderful story to share with us about a manager or a situation that was influential. I’ll turn it over to you, Adrian.

Adrian Espinoza:   Thank you. In my first job, in Bolivia, just finishing college, I started working in an oil company, like food oil. At that time, I had a manager, Albert Enrico, I remember his name. The first day he told me, “This is going to be like this.” He’s going to be strict, He’s going to be like military or something like that. I was just finishing college. This guy comes and tell me [this is what is expected]. In the first months, it was 12 hours working.

ERH: Wow, per day?

Adrian Espinoza:   Yes. I couldn’t sleep because I had to be in and on the computer, each morning and get things done, even though I didn’t know what to do. There was a lot of learning. I like learning because when you’re young, you are like a and you want to learn the best as I can. Even though I admired him a lot because he knew everything, I think at the time I wanted to be a big manager of this big company, one of the biggest in my country, and travel city to city. At the same time I was thinking… I don’t want to spend 12 hours of my life every day to get there. I was sitting at the computer and thinking, “I have to change it to something.”

I’m a chef apprentice now because I wanted change in my life. I think that was positive for me. You know what I mean?

ERH:  Right. Sometimes the greatest lessons are just seeing … Experiencing something and then seeing that it might not fit, right?

Adrian Espinoza:  Yeah. It was more like, hey, I could be him but I choose not to… He was strong and I liked that because nobody is perfect, right? I liked that from him, but I wanted to take another path. I think that was positive for me. He was really positive for me because he helped me learn more about life.

ERH:   That’s fantastic.

Adrian Espinoza:   Yes.

ERH:  Now, do you use any of those lessons as you are working on becoming a chef apprentice?

Adrian Espinoza:    Yes, of course, I mean, because he taught me to be more disciplined and be more, I could say, straight with myself in order to learn. That helped me a lot. It pushed me to get stuff done. That’s what I think matters… You can try every time, but to get things done, it’s more important. That’s something he taught me.

ERH:   Thank you so much for sharing that, Adrian.

Adrian Espinoza:    Thank you, Elizabeth.

ERH:  Those stories remind me that the smallest example in management can influence someone for a lifetime and most certainly encourage someone to stay with an organization today. You can learn more about Dan, Lauren, Eli, Gretchen, Laura, and Adrian above.

Thank you for spending time with The Art of The Break. I hope you learned even one thing to make your day better or something to inspire you to help your team or employees. If you are interested in being part of better work environments, please sign up for our email at I promise not to fill your inbox.