I recently gave a talk to a room full of founder/CEOs about how to leverage your board of directors by shifting from a reporting board to a collaborative board.  It can be tricky, but for those who do it, the company and the founder can grow wings. Part of the shift involves trusting your board and bringing them into your confidence, being vulnerable with them, and asking for their help and input when things aren’t working.  This can be scary for most CEOs because the board usually has the power to remove him/her. However, if you have the right board members, and if you create the right dynamic at the board level, this usually won’t be the outcome.

One founder in the room raised his hand to challenge me. He said, and I’m paraphrasing here, “That’s a lot of ifs and usuallys. Why would I take that risk? If my board can fire me, why would I risk being fired and losing my company by admitting weakness and vulnerability?”

I love this founder for asking that question – it’s at the heart of why most CEO’s don’t go to their board with challenges.

Here’s the thing: There’s a difference between playing to win, and playing to not lose. 

Let me tell you a quick side story. I played volleyball in high school and club ball in college. I’m short, so was never going to be really good, but I loved it. My freshman-year dorm was across the street from a frat house with a sand court in the front yard, and I was dumb enough to ask to play with the guys who were much taller and more skilled than I was.  They were nice enough to let me participate, and for a whole year I spent every day after school and all my weekends there. Eventually, I got good enough to hold my own, and we competed in a few sand tournaments. I never won, but placed decently, and even taught the volleyball class at the University for a while.  

Fast forward 20 years, I started a couple of companies, had a couple of kids, moved a couple of times, and made 100+ investments, raised a couple of funds, traveled an inhumane amount, had a ludicrious number of direct reports, helped grow Techstars… basically, I had zero free time to do things I loved like play volleyball.

So recently, I decided to pick it up again. I found myself on a co-ed, indoor sand team. I was pretty nervous to start, but hey, I’m decent at this sport, so I figured once I got my legs under me again, I would be okay. Well let me tell you – I was bad, so embarrassingly bad. I shanked every pass. Put every attack in the net. Dove and missed every ball. Lost every overhand serve. It was so bad that one teammate asked me to serve underhand, a big hit to my already fragile ego.  It’s been a long time since I felt that humiliated. We lost every game that season and were relegated to the lower league, largely because of me.

Astonishingly I was invited to play the next season (I’m 100% sure it was because they couldn’t find anyone else), so I swallowed my pride, said yes, and started practicing, figuring my ego needed to practice sucking in public. Luckily I got better and better. I wasn’t anywhere near as good as I was 20 years ago, but at least I wasn’t an embarrassment anymore. Yet I continued to serve underhand – because I was so afraid of losing the serve. A killer overhand serve will earn you points, but a bad serve will earn the other team points. You can win whole games on a killer serve alone. When I practiced, my overhand serves were killer. They were strong and hard to return and my team kept asking me why I wasn’t serving overhand in the games, but the truth was I was afraid to choke. I didn’t trust myself anymore and I didn’t want to cost us the game. I was playing to not lose, I was not playing to win. Despite my conservatism, our team placed #1 in that division and got promoted back up to the higher league, but, I didn’t get invited back to the next season because I didn’t help win games. I just helped not lose them. And quite frankly, I don’t blame them; they wanted to win.

This founder’s question is like my underhand serve. It’s playing to not lose. And when you’re in the high-stakes game of entrepreneurship, especially if you’ve taken venture capital, there are only 2 outcomes, winning, and losing. So if you’re playing to not lose, you will likely, eventually, lose. 

Here are common behaviors I see founders take that show they are playing to not lose:

• Not being honest with the board
• Stacking the board with friends rather than skills/knowledge/wisdom/networks/courage/honesty
• Not asking for help
• Trying to be good at all things
• Not having a difficult conversation with a co-founder, leadership team member, investor, yourself
• Not asking for feedback
• Dismissing other people’s feedback
• Needing to win disagreements
• Not hiring people smarter/better than they are
• Hiring up, and scaling up before true product / market fit
• Trying to raise more capital because you hired/scaled faster than you should have before you have product market fit, and you’re now out of runway
• Trying to keep the business alive when there’s clearly no real business, and burning through all the investor capital without returning any of it
• Not making a major decision
• Micromanaging, not trusting your team
• Using policy as an excuse or crutch for not developing judgment

There are infinite ways that playing not to lose manifests but at its core is fear; fear of failure, fear of loss. The trouble with this behavior is that it almost always manifests that which you are exactly trying to avoid. For instance, not being honest with the board will eventually lead the board to not trust you, which will either cause them to not vote with you or they will try to remove you as the CEO. It just takes longer, but in the interim, you’ve burned all the bridges and not gotten the help, trust, and support you needed to turn the issue around.

Don’t mistake playing to win as ruthless, win-at-all-costs actions; that simply isn’t true either. You might win a battle, but you will eventually lose the war. Playing to win does mean taking risks, but it means taking calculated risks intentionally, collaboratively, and intelligently. In the land of startups, a win-win-win outcome is possible because together you can create more value than you othewise could apart.

Here are excellent playing-to-win behaviors:

• Recognizing your weaknesses and staffing for them
• Asking for help, asking for feedback
• Admitting a mistake, asking for forgiveness
• Build and manage a board of directors that can be as influential as your leadership team
• Make a hard decision, even if unpopular
• Hold people accountable, especially yourself
• Taking a big swing, that’s calculated, intentional, aligning, and collaborative, with tailwinds
• Having a scary conversation with someone
• Conserving every f’ing penny until you have product market fit
• Keeping your day job/not raising money until you have product/market fit
• Shutting the company down and returning capital to investors when you can’t see how you’re going to make it work
• Saying NO to distractions
• Being generous with equity with the *right* co-founders, employees, investors
• When people disagree with you, get curious, not defensive
• Investing in your own professional development
• Identifying the one thing your business can be best in the world at, and going hard at it. Don’t make marginally improved products/services.
• Recognizing when you aren’t best suited for your role in the company anymore

Of course, all of this is situationally specific, and the true answer to any question is “It depends” – but I ask you – are you playing to win? Or are you playing to not lose? Are you serving underhand? Or overhand? What can you do or stop doing to shift to a winning orientation? I encourage you to ask that question, not only of yourself, but together with your team and your board.  “What could WE do, or stop doing, to help us shift from playing to not lose, to playing to win”. What a powerful way to reorient and kick off a new year.