The Scariest Meeting I Had as a Founder/CEO: The Board Meeting

There were very few moments in my life that were scarier than the very first time I went into a Board meeting as a CEO. That’s hard to admit, but it’s true.

I had been part of Board meetings before as a Founder, but never as the CEO. I was never the one on the hook for the meeting before. I was never the one who was scared shitless of looking like an idiot who didn’t know what the hell he was doing in front of his investors before. Imposter syndrome had never been so real for me before.

After many years of running and fearing Board meetings however, I started to learn a few key strategies that helped my navigate the fear and build a good CEO/Board dynamic.

Know your target audience:

Just like any good sales game, you need to put yourself in the shoes/chair of the other person, understanding their pain, goals and ambition, and then provide solutions without ‘selling.’ It’s the same with Board members. In most cases, they are investors, and they gave you money expecting to get significantly more back. If you forget that this is their primary goal and driver, then you are failing from the start. And while that’s their primary driver, there are many subtexts to the relationship that you, as the CEO, also need to serve.

Avoid the ‘Big Reveal:’

Feeling like they are out of the loop or lack information makes Board members nervous. I know my mentality as an early CEO was just to get through the Board meeting unscathed, and then worry about the Board the next time I needed to hold a Board meeting. Out of sight, out of mind. That was a huge mistake. Waiting until the Board meeting to get everyone updated and hoping to wow them with my brilliance as a CEO with flashy presentations and strategic solutions always lead to very difficult discussions during the meeting. And I didn’t always have the answers.

I grew up in the Agency world in NYC, and this mentality with clients is called the “Big Reveal.” Provide background and supporting info at the beginning of the meeting and then build to the moment when someone pulls the paper off of the brilliant new creative/strategic direction the agency is suggesting. That’s NOT the way to run a Board meeting. I also happen to think it’s a losing strategy for agencies as well — but that’s another blog post.

I realized the best way to get the Board on-board with what was going on with me and the company, especially if I was about to propose something big or different as far as direction, was to make sure I communicated often and got them bought in to the ideas way before the Board meeting. Starting the conversation early as informal discussions of what I was thinking and why, gave me a chance to get them up to speed and also uncover and real objections or things I missed way before the Board meeting. This allowed me to spend most of the Board meeting discussing ways to move the strategy forward together instead of wasting time defending it to individuals.

Have the meeting before the meeting:

One good supporting process I found for this is to create a Shared Google Doc/Folder for the Board meeting. In it, I would share all the key materials for the Board meeting at least a week before the meeting with instructions that the material should be reviewed prior to the meting and specific questions submitted using comments in the doc before hand. This gave me a chance to answer specific questions about things like financials ahead of time and when I had time to research the correct answers instead of being on the spot in the Board meeting.

In my intro, I would have at least several paragraphs that contained my thoughts — the good, the bad, things I’m worried about, etc.- in a narrative format. That gave the Board a look into both my thoughts and emotions in a way that they could connect with, and gave them real insight into the ‘feel’ of the business. Often times, numbers — especially good numbers — can mask real problems, so by providing a real narrative instead or just numbers and slides, they had a glimpse into the real business, not just the high level.

This process allowed me to hold the meeting virtually before the meeting actually happened. We were able to address the details of the business ahead of time and that freed up most of the meeting to focus on the future, our move forward strategies and how to create more value as a company for our investors.

They want to add value:

Investors have an inherent need to feel like they are adding value. If you don’t give them a good way to add value, they will find their own way, and that’s not always the best way for you.

Communicating often, and gaining buy-in as above, I could now find ways to get the Board members involved in helping to move the strategy forward. Whether that was introductions to key new people or Sr. execs from other companies that had gone trough similar things to help us navigate the effort, or data based on their research to help us establish key KPIs or metrics, or even getting them thinking about new or bridge funding. These were all key value adds that I was able to give them to help move the company forward — and as a result, bolster their chances of getting much more money back from their initial investment.

They key here for me was realizing that it was my job as the CEO to actually give them ways to add value. If I hadn’t put myself in that position because I was relying on a Big Reveal, or I had neglected ongoing communications, then they would find their own actions to feel like they were adding value. And often those actions became distracting and scary. They would spend time focusing on specific financial details, or question my strategy as opposed to other companies they knew. Or they would push me to spend more too fast, or less too slowly. They point was, they would always default to the things they knew and felt comfortable pushing on. That’s what humans do — especially when they have dollars on line. So my job was to give them ways to add value that were actually helpful. And I could only really do that if they were already on board with where I was leading the company.

If you’re not leading the Board, they’re leading you:

The other huge mistake I was making early was asking the Board, “What should I do?” I was often scared to suggest something that might be considered inexperienced or incorrect and, as a result, lose credibility with the Board. So instead, I would simply ask them what I should do. Now I’m a huge fan of transparency and being candid and real. However, again, by simply asking what to do, I was actually creating anxiety for my Board members and creating a vacuum of leadership that they then felt the need to fill. If I wasn’t leading the conversation, they would. And as a result, they would take on the leadership role I was supposed to be providing.

So, instead of asking, “What should I do?” I learned that changing that context slightly, actually gave me a much better outcome. When there was something I was unsure about, I would do some research first and frame the discussion by saying something like, “There’s something I’m concerned about. I’m a little unsure of how this plays out, but based on my research, here’s what I believe we should do. However I would love your input to make a final decision.

I was still providing the transparency I believe in, but instead of abdicating my leadership of the Board, I was providing vulnerable leadership as well as a context that reinforced my credibility as a leader and gave the Board members a way to add value and help move the company forward that didn’t usurp my perception as the leader.

Leading a Board meeting can be a very scary thing — I know it was for me. But Board members can be huge allies, help you through some really tough situations and be massive assets in building your business. Managing and leading the Board correctly, creating a dynamic of trust and credibility, is how you create a CEO/Board relationship that can get you through the tough times instead of making them worse. And there are always tough times.

I know there’s more here and I will probably go a lot deeper on each of these topics in the future, but I wanted to get some high level thoughts out because I’ve been discussing these specific topics a bunch lately with several CEOs I work with and hopefully this can help lots of other CEOs. If you have other specific topics related to this, please leave some thoughts in the comments.

Be a #BadAssCEO

This post is part of the “#BadAssCEO” series. I work with CEOs struggling with the immense and often overwhelming decisions inherent in running and growing a business. To hear more as they are published, or contact me about speaking, follow me here, on Twitter (@Dgmandell), or reach out directly at VentureVoodoo Partners.

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store