Many people such as venture capitalists have met and judged me and my team over the years. I’ve always found this simultaneously amusing and frustrating, because in my experience, they’re more wrong than right. I became seriously allergic to this. But then I put on their shoes and walked a few steps, and the results surprised me.

This post isn’t really about my team or any VC or the like, and I won’t write anything that could be taken to refer to a specific individual. But I want to describe for you the experience of being judged by people who are trying to decide whether to invest in your company. Because they’re operating with extremely limited context, they try to figure out whether you know what you’re talking about.

I’ve had VCs sit with my team and then matter-of-factly tell me who’s strong and who I should fire—and they had it exactly backwards, as borne out by several years of subsequent events. I’ve had VCs play mind games with me, like scoffing at me just to see how I’ll react, or flattering me just a little, or trying to “pump me up” to see how much I might exaggerate to try to be persuasive. These and many other tricks are stock-in-trade for VCs. They use them solo with people like me or my team, and in group presentations.

My nature is to be who I am and not really respond to manipulation like this, so I usually keep a poker face and move on with the conversation. But I slowly started to form an opinion that I was dealing with a pack of fools. Not only do I not enjoy head games like these, but these people were so outrageously wrong in their opinions of me and my team.

Cut to a few years later, and I was trying to learn how to manage a Board of Directors. I asked a friend of mine1 to help me observe another entrepreneur’s board meeting, and he obliged by introducing me to a seasoned CEO who was growing her fourth business after three hugely successful exits. She agreed to let me sit and listen at her next board meeting.

Traffic was worse than I expected, so I arrived about three minutes late, after the board meeting was underway. This CEO was all business. She had a large team in the room, and a handful of investors and independent board members. I slipped in quietly and sat and watched.

Despite being too late to hear any team introductions, it took me about 90 seconds to figure out who was who. The marketing person was just so stereotypically a marketing person, with slightly stylish glasses and a colorful shirt, and looked very pleased with himself. The sales leader had leather wingtipped “I’m a sales leader” shoes and was typing a lot on his laptop, probably answering emails to close deals mid-meeting. The VP of Engineering had tried to dress up for the meeting, in the way a person who normally wears old dirty clothes dresses up, and didn’t make much eye contact. The inside counsel was leaning back in his chair with a bored expression and his head tipped slightly back to the ceiling. And so on.

But as the meeting progressed, I learned I was wrong! The sales leader was the bored one. The marketing leader had the scruffy clothes on, and the head of engineering was the dandy. The inside counsel was a random person I overlooked.

These were mistakes anyone could make, so that didn’t faze me. It was pretty clear to me, though, who was going to last in this company. There was an overseas engineering leader who was dialed in on the phone, and that person needed to be fired right away. His part of the board meeting was a disaster. He’d failed to deliver on nearly every commitment the board mentioned from the previous meeting, and he was back on his heels as the board asked him all kinds of embarrassing questions. The CEO was defending him.

When it was the sales leader’s turn, he made excuses about missing goals, and kept comparing metrics against benchmarks. There didn’t seem to be any strategy to the sales process; it was all thoughtless best practices. The board members were asking tough questions that I would have asked, and the sales leader was deflecting. The CEO mostly didn’t intervene, but occasionally came to the sales leader’s defense too.

Speaking of the board members, one of them was incredibly impressive. He asked questions that drove to the heart of the matter, pointed out things that people were missing (or needed to be said because someone was evading), and contributed ideas and possibilities that made a ton of sense. Every time he spoke, he added value. It seemed like he was the best thing the team had going for it.

It was a confusing board meeting: I felt like my judgment of the team members couldn’t be right, given how experienced this CEO was. I didn’t realize that I had been pattern-matching at a superficial level, the same way the VCs did when I was on the other side of the table.

A few weeks later I asked the CEO if we could schedule a followup call to discuss. I tried to probe and learn whether my impressions were correct, without implying that I had a dim view of any of the team members.2 She walked me through the reasons each person was strong in their areas, and how she made the most of their strengths and arranged the team and processes to neutralize their weaknesses. She also gave me a different perspective on the board member who’d seemed like such a powerhouse to me.

That was years ago. All of the team members are still there and the company is growing like a weed.

It’s almost incredible how wrong I was about that CEO’s team. I’ve learned a lot from this experience. I gained empathy with the way VCs treat me and my team, and through that, an ability to respond differently to it, and contribute more positively to conversations with VCs.

But by far the biggest takeaway is that I’m relatively ignorant and unskilled. I found that the CEO knows a lot of things I haven’t yet learned. Managing the board, for example; I have not yet developed the skills to handle a situation where board members and I feel differently about a team member’s performance. I may never be as skilled at that as the CEO of that company. There are many other things I won’t mention because there’s no way to anonymize them.

I’ve since found that I’m wrong about other things, too. A friend of mine seemed to be in a fundraising situation I’d faced, and when I shared my lessons learned, he didn’t think the circumstances were the same. He was right. That happened with another friend, too. I also shared some of my recruiting principles with a couple of founders who have gone on to do it very differently and appear to be building companies that will be household names.

Judging people, situations, and abilities is hard. Being wrong when I was sure I was right has helped me realize that “it depends” is probably the only universal truth. It’s also helped me have more empathy and respect for my counterparts.

All work in progress, of course.

  1. This story is a heavily fictionalized and anonymized composite of several experiences. If you think you know which events I’m writing about, you’re probably wrong. [return]
  2. I was probably unsuccessful in this. [return]

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