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Three High-Level Themes that Emerged from our CEO Roundtable

This guest post was written and published by Mark Somol, Core member, CEO at Zeal Technology following the CEO Roundtable at Underscore’s recent Core Summit.

“It’s lonely at the top.” How many times have you heard that phrase? For many leaders and CEOs, it feels very lonely holding the top leadership position in an organization. Thankfully, you are not alone. Paradox? No! What I heard at the CEO Roundtable is that the company we seek is that of our peers, those who hold similar levels of responsibility and accountability, with whom we can share our challenges and seek advice.

The three most salient elements of our roundtable discussion at the recent Core Summit are outlined below, with full credit to all the participants who freely shared their ideas and insights.

1. Don’t solve your investor problems at the expense of customer experience.

One participant made a comment that sometimes he makes decisions based on the needs of his investors. For example, some investors push entrepreneurs to build their leadership teams faster than the business can reasonably support.

Several other CEOs chimed in, echoing the same comment. In particular, entrepreneurs believe they should focus on the needs of their customers first. Take care of customers and sales, the thinking goes, and investors will be happy.

For example, a VC pushes you to bring in a VP of sales. Many times, that leads to the VP of Sales requiring additional resources to build a team. So, you hire managers and BDRs. Before you know it, you have a 10-person sales team and you don’t even have product-market fit yet!

Another participant made a particularly insightful comment: good sales people can do such a great job of influencing a customer to buy your product that they may be masking the fact that your customer ultimately doesn’t need your product. That customer eventually churns out. It’s not your sales person’s fault! Kudos to them for winning a new customer!

Unfortunately, this kind of situation can greatly diminish the feedback loop you need to have with your customers. This loop is absolutely essential to ensuring you build a product that solves a big enough pain point from which you can build a scalable business.

2. To get the most out of a mentorship relationship, you need to be vulnerable.

A hot topic during our discussion was the role of CEO advisors. Some of the most experienced CEOs in the room declared emphatically that everyone in the room should have an advisor.

Advisors can take many forms; mentors, CEO groups, executive coaches, and even your investors. We polled the room to see what kind of advisors the group currently has:

  • 80% of the group has at least one mentor/advisor
  • 33% of participants belong to a CEO group
  • 5% engage an executive coach

What should you look for in a mentor?

Most people in the room agreed that an ideal mentor is someone who has been an entrepreneur or CEO in the past. You want someone who has been through and even overcome the same struggles, questions and challenges that you are experiencing. A mentor who has worked with VCs and boards can be invaluable to a first (or even multi-) time CEO looking to improve his or her own ability to communicate with investors. Dig into your network, talk to prior colleagues and second-degree connections to find people you suspect might provide you great guidance.

The participants in the room who are part of a CEO group added that sometimes you get great advice from people who are in completely different businesses. For example, in the CEO group I joined, there are founders of a landscaping company, a large jewelry business and a consulting business. Each of their perspectives is fresh and often times they have advice I wouldn’t hear from a tech CEO.

Additionally, many very successful entrepreneurs had mentors who helped them along their pathway to success, so they are willing and motivated to give back to someone else. This culture of “paying it forward” is pervasive in many CEO groups as everyone understands the inherent communal benefit to supporting other entrepreneurs.

And, you may also find that a mentor who has functional experience in one of your weak areas can help you through many challenges. A sales or marketing mentor for a technical CEO is a great idea! And don’t stop at one mentor — many participants have multiple mentors who provide valuable insights on a variety of different challenges commonly encountered when building a business.

How do you get the most of out a mentor?

Most agreed that it is up to you to be assertive and ask for help. Be humble and know that it is your role to take the lead on how you want the relationship to work and what you want to discuss.

You need to keep an open line of communication with your advisor. Regular meetings can be helpful, but many times what you really want is to be able to pick up the phone and call your advisor to ask for help on a particularly time-sensitive problem.

Ideally, you have an advisor that holds you accountable for what you commit you will do. It’s the right pattern of behavior and it is a way to hold yourself accountable to taking action. If you haven’t done something like this before, then imagine that you have a personal goal that you are trying to achieve. Perhaps you want to run a marathon in a year. What is one of the best ways to hold yourself accountable to that goal? Tell everyone you know!

Perhaps the most insightful comment during this discussion was that you need to be prepared make yourself vulnerable to your mentors to get the most out of the relationship. You need to open up and be honest about yourself. Be honest about your strengths and weaknesses. Be honest about where you need help. Be honest about how things are going at home. You will get so much more out of the relationship if you do so.

3. Stay attuned to your “why”…your purpose…the meaning behind why you started the company in the first place and why you believe so strongly in what you are doing.

CEOs set the vision and inspire their teams to achieve that vision. Sounds simple on paper, but it is so much more complicated than creating a vision statement. Is a vision static, or does it change over time? What do I do after I print the vision on nice pieces of paper and put them up on the wall? The devil is in the details.

“A vision must be expansive enough to be compelling,” said one participant. “But you need to be able to paint a realistic picture on how you can achieve the vision.”

Vision must be paired with strategy. It’s not enough to know where you want to be in 5–10 (or 100) years. A great CEO determines the right pathway to achieve the vision, and inspires their team to hop on that path with them.

What is that pathway? Strategy. Vision + Strategy is how you get where you want to go.

For example, you believe your product or idea is applicable to every company in every industry in the world. We all do. But, it costs an incredible amount of time, money and resources to try to reach every company on the planet. So, you must start small and in a market that needs your product. Win in one market, and then move to the next. Keep winning.

There are a million places to read about strategy, so I won’t go into that here. Instead, I will relay one of the stories told in our session, with names removed:

“One of my companies had a huge financial services company as a key prospect. When I asked them, ‘if we build this product to your requirements, will you buy it.’ They said ‘yes.’ So, thinking we had a market in large financial services companies, we built the product.

When we went back to them with the working product, they didn’t buy it. Times change, strategies change — whatever the reason, they didn’t need the product anymore.

So, we had to pivot our go-to-market strategy. We switched and went after mid-market companies. We found success there… a lot of success and built a great company.

Eight years later, we made it back into the large financial services market!”

Clearly, there was nothing wrong with his vision. Nevertheless, he had to change his strategy to achieve his vision.

We ended the vision discussion with thoughts about how to keep your passion and energy up during to the tough times

If you need a pep talk, watch Simon Sinek’s Ted talk on “How great leaders inspire action”.

Or, if you want to see that other great leaders have faced many of the same challenges you are facing, read Ben Horowitz’s book “The Hard Thing about Hard Things.”

Roundtable participants, by the numbers

We are all data-driven these days, right? After reading this, you may wonder, who was in the audience? What kinds of people participated in the conversation? We did a couple of polls early on in the session, and here is the group’s composition:

At what scale is your company?

  • No product = 25%
  • <$1mm = 50%
  • $1–5mm = 20%
  • >$5mm = 5%

How many have raised outside capital? In any form, VC, Seed, debt, friends & family, etc.

  • Yes = 95%
  • No = 5%

In summary, I would say that the most impactful insight coming out of our table was unspoken: it was the willingness of each participant to share their experiences and to help each other. Every bit of content in this post came from the people in the room. Buoyed by this unspoken camaraderie, individuals opened up to a group of people whom they had never met before. People shared their experiences without any hesitation. Perhaps their next advisor is a person who was sitting in that room.