Carving out an entrepreneurial path is not for the faint of heart. Founders and CEOs need to demonstrate conviction to their teams and investors. But no founder or CEO has all the answers, and that’s where mentoring comes in.  
On September 21, MESA mentors and mentees came together to share their experiences in the “entrepreneurial trenches” to a capacity crowd. They offered their insights on the issues facing founders and CEOs as they look to grow, and best practices on how to get the most from a mentorship experience.
Angie Franks, ABOUT Healthcare CEO and MESA Mentor
Chad Halvorson, When I Work CEO, past MESA Mentee and current MESA Mentor
Jim Moar, MESA President, MESA Mentor and Panel Moderator
Melissa Kjolsing, Reema Health Chief Growth Office, past MESA Mentee (unable to attend but offered written responses)
Following introductions, Jim Moar facilitated the discussion. Highlights here are edited and condensed.
What caused you to seek mentoring?
Chad: When I Work was founded in 2010, and in 2011 I started to reach out to potential mentors and mentoring organizations, and it was for a couple of reasons. Back then, there wasn’t the community that exists today in the Twin Cities. It was like operating in a bubble: you don’t know what you don’t know, you don’t know how to navigate issues that come up, especially when you’re trying to figure things out for the first time. I knew there were important things that I needed to sort out. I was incubating the company inside of another organization and I had to figure out how to get When I Work out of that company in a way that was going to be satisfactory to venture capitalists when I was going to raise money, while staying amicable with my partners in the other business. I knew certain things needed to happen conceptually, but I had zero other individuals to work through these issues with me. When I found MESA, I felt that there was a place to not just have a sounding board, but also to discuss these issues with like-minded individuals who had been through these things before. It was both getting advice on how to deal with the issues I was facing, but also my curiosity for learning about business and growing a company.
Melissa (comments shared by Jim): Starting a company is challenging and lonely. I sought mentorship, specifically through MESA, because it provided structured and dedicated one-on-one support. Very few people understand what you’re experiencing on a day-to-day basis – from cash flow to employee issues to customer challenges and wins! Mentors who have experience starting and running a business have that shared experience and ‘get it.’
What caused you to be interested in mentoring?
Angie: I was excited when I learned about MESA and had the opportunity to meet the founders and learn more about what MESA is trying to do inside of the Twin Cities in Minnesota’s startup and early-stage economy. For me, the opportunity was to take some of the experiences that I had lived through to help others, and maybe help them see something through a different lens or experience. What got me interested was the ability and the opportunity to give back. At the same time, the opportunity for me to learn was equally relevant and equally part of the decision. From my perspective, I saw mentoring as very much a two-way street. While I have some things to offer, so did the person I was working with, and I think that multiple is in spades. It’s been a powerful experience for me professionally and I’ve loved every minute of it.
Jim: Both Chad and Angie have mentioned MESA, so let me tell you about the organization because I think this also just gets into a mentoring approach. MESA is an 11-year-old organization and I’m one of six co-founders. if you go back 11 years, the Twin Cities was not pulling its weight in the tech scene. If you go back go back 25 years, the Twin Cities was, but it was in a hardware world and not a software world. And as acquisitions and the transition to software happened and you looked at the size of our population relative to where we were on the tech scene, we just weren’t there.

So, six of us got together and said, ‘Okay, that’s reality, what are we what are we going to do about it?’ We kicked around a few ideas and came up with what we still do today – we offer pro bono mentoring. It’s free to the founder and CEOs of Minnesota based startup software companies and the mentoring is done by C-level software executives who have startup experience themselves. The entrepreneur has someone sitting across the table and talking to someone who has been in their shoes. MESA mentors meet with their entrepreneurs monthly and that’s because there’s so much going on in the startup that if you don’t, you get out of touch. We typically stay and work with an entrepreneur for two to three years, sometimes longer. Our mission is to grow the size and vibrancy of startup software community in Minnesota – so as long as we’re working with a company and think we’re bringing value, the mentor thinks we’re bringing value, and the company is growing – that’s fulfilling the mission. We just recently added our 37th mentor and just added three new mentees last Friday. We’re at 20 current mentees and we’ve worked with about 75 companies in Minnesota over the years.
What was most valuable to you in the mentoring process?
Melissa (comments shared by Jim):  The conversations were dedicated to my specific needs and problems. When we met, we went deep on key issues and solved problems for my business. We solely focused on Recovree – from our sales process to marketing to employees. I felt validated, supported, and accountable with my mentors. It was the best use of my time because I was able to confide in people who understood what I was going through and brought incredible value to my business.
Chad: There were two to two and a half stages that brought a lot of value. In the earliest stage it was figuring out these problems that seemed very complicated, like spinning the company out of another company and getting it into a position where it’s fundable by VCs and stand on its own. That was the first major hurdle I was able to work through with my mentors and understand all the moving parts of what I needed to do. To hire a lawyer to help me navigate all the of steps along the way would have been very costly. Through the mentoring relationship I came to understand when I actually needed a lawyer. With non-tech founders or executives there would have been a lack of relate-ability or understanding of what needed to happen.
Then, you get to the point where you’re not in that early stage, and you realize everybody else has individualized interests, and suddenly, there is loneliness in the CEO chair. There are plenty of people who want your attention or need your time or energy or effort – but you can’t talk to them because many have an investment or an issue or agenda. As you scale, you get a circle of other people on your team and board members that bring expertise to the business problems. Mentoring then becomes more about CEO coaching and problems that you want to talk through with someone who is completely untied to the incentives of the investment, or their career growth, or as an executive on your team. In the mentorship relationship, there are no strings attached. The independence of a mentor is unique. They’re not being compensated, and they don’t have skin in the game. It changes your ability to let your hair down, and not have to be buttoned up or watch the words you’re choosing. You’re talking with someone who’s got no skin in the game but is fully aligned with your interests.
Jim: I think for all of you as you’re thinking about finding a mentor now or a mentor for the future, I think what Angie, Melissa and Chad are saying is – identify why is that person here. I agree with my colleagues that if you’re talking to someone that’s got another relationship, primarily a financial one, you will hold back on certain things you’ll talk about. Having mentored 15 teams and companies from 11 years with MESA – I can’t tell you how many times that we started with the entrepreneur saying, ‘I need to talk to you about something I’m not talking to anybody else about.’
Chad: A couple examples. In the early days, I could talk to my business partners because we had a vested interest in both the parent company, and in When I Work because we were funding it and contributing to it in some way, shape or form. I was able to talk with them to a certain degree about getting it spun out. But I certainly couldn’t talk to them as openly as I could with my mentors because mentors had no interest in how we ended up doing it.
And then as you scale, there are issues that include whether someone on the team is the right fit and you want to talk through how to approach managing that person to where they need to be or managing them out of the company – and it might be a senior level executive. You don’t want to talk to other senior executives about this because it might get back to that person and that’s not going to help you work through the problem. If you talk to a board member, they’re more likely to steer you towards firing the person vs. working through your own process. And it can go as far as having conversations with your mentors about, ‘Alright, do I still want to do this job long term? Do I want to be the CEO for the long term? Is that something that would get me out of bed?’ I certainly would not want to have and did not want to have that conversation with board members or investors until I knew exactly where my head was at because that would trigger the interests that they have. Those are just some good examples, and that’s what we mean when we say with the right mentor that has no strings attached, you don’t have to be measured. You can be more open and vulnerable with who you’re talking to because their only interest is helping you and helping the company.
From your mentoring experience, what have you learned that’s helped you?
Angie: It’s great when you’re running a business to mentor somebody else because you leave your own problems and just focus on them. What you end up learning is that all the problems that we deal with in the mentoring relationships are the exact same problems you’re dealing with and that accompany your brand. There might be more zeros from a financial perspective, or more zeros because you’ve got more employees, or more zeros because there are more customers – but the exact same fundamental issues are there. By talking through and helping someone with some of their issues, you in turn are working through and thinking about your own.
I’ll give one other example: you can get exposed to different types of businesses when you mentor. It’s fun not to stay in your lane and in your comfort zone. I did some mentoring with a construction software company and the opportunity to learn some of the financial and competitive dynamics in other industries helps you think about your own financial and competitive dynamics in your own industry. You come up with a broader perspective and point of view. All those things over time helps form more pattern recognition. And that for all of you, especially those of you that are younger and thinking about entrepreneurship – pattern recognition is a big part of what a mentor/mentee relationship can bring.
Jim: To add to that, learning for me also comes from being on a two-person mentoring team. A fellow mentor is talking about his experience in addressing a particular problem and I’m listening to him and going, ‘Wow, I can use that.’
More importantly, mentoring helped me refine a leadership style. Good mentors don’t tell. Good mentors listen. They tell stories, give options and when they walk into that next monthly session, recognize that the don’t know where that entrepreneur is head or heart is – and are willing to assess if they are at a high or at a low level. When you’re at the top in an organization, it’s easy to fall in the trap of telling, in part because it’s easy and you can get away with it. But you’re so much better off when you’re you are giving people space to go off and figure things out. I can say that mentoring had refined how I talk to people and how I address problems, and it’s a lot more enjoyable.

In addition to some of the points you’ve made, what do you consider mentoring best practices?
Chad: For the entrepreneur, I think a best practice is to let your guard down and take that approach with every issue, topic, problem, or goal that you’re trying to work toward. Be willing to lay it all out there: what’s working, what’s not working, and what’s occupying your headspace more than you think it should. The other point is to find that mentorship relationship where there are no strings attached. You will always get people that want to get equity by being an advisor or they want to get compensated in some way. Even if it’s a small string, it’s attached, and you’re going keep your guard up a little more. It’s transformative if you can completely let your guard down. 
For the mentor – I’d say ask good questions. From the entrepreneur’s perspective, that’s probably one of the best things that a mentor can do to help move the issues and the solutions forward. A good mentor will ask good questions that will mirror things up to your face in a way that you haven’t considered before.
Angie: For the mentor, you’ve also got to be prepared and organized. Have a plan to work with your mentee to understand their priorities, areas of focus and key issues. You could be working with somebody on growth or go-to-market strategies, or on financing and getting prepared to raise capital. It could be that you’re at the stage where we’re going show up to this meeting and talk about some founder and co- founder problems. So have a focus, but at the same time be flexible.
Take notes. It’s important to keep a notebook to go back to, especially when these relationships last for years and the company you’re with may go through multiple transitions. You want to be able to go back and say, ‘I feel like that we talked about this before and this was a good line of thought at the time. Do we need to pivot?’ Notes are important.
As a mentor you have to resist the urge to answer the question for the mentee. You’re not there to do that. You never see exactly what they’re seeing and experiencing boots on the ground running their business. You can ask, ‘Hey, have you thought about this?’ Frame it up in the form of questions so that the person you’re working with will go off and think it through and make it their own. At the end of the day, that CEO that you’re mentoring is going to be responsible and accountable for the decisions that they make. You don’t want to shift that relationship to where you suddenly start feeling like you’re not mentoring them, you’re dictating orders. I think that those are the important things: have a focus, but be flexible, take notes, and ask questions.
Melissa (comments shared by Jim):  From the mentee side, Melissa had a couple of comments that reinforce other comments today. She said, come prepared, have an agenda and specific questions and topics. This next one was interesting for me as a mentor, which was: Share your gratitude often – this is a relationship unlike any other and it’s important to nurture it. 
Jim: I would also add from the mentee side, that you’re getting these questions and getting stories from experienced mentors – internalize it and make it your own. We as mentors can give advice, but it’s your role. You can say that’s not really hitting me, or perhaps take two different thoughts and combine them to make it your own. At the next session when you come back together, you can see that the mentee has thought it through, built on it and knows how they will move forward.
For mentors, it’s about guiding, but sometimes it’s about pure education. At MESA we deal with software startups and the founder is most often more technical and has never sold in their life, so we might have to do a little primer on Sales 101. Founders are smart about their product and their business, but it might take them longer to figure out other things for the business on their own. A mentor can speed things up and do some teaching when teaching is appropriate.