Welcome Entrepreneurs. I’m so glad you’re here.

If you didn’t catch last week’s post about the phenomenon called “Audience Capture,” and how it relates to the lean startup experience, check it out here.

Now then. We’re going to try something different today. 

I’d like to invite you to watch the video below and put yourself into the hypothetical situation I describe as fully as you can.

It’s a relatively common situation in the life of a VC backed, startup CEO, something I’ve experienced personally, and through which I’ve supported many founders.

During the video, observe what comes up for you, and when the video is over, ask yourself, “What would I do?” 

Importantly: Answer as quickly as you can without thinking too hard or trying to find the right answer. 

Answer right away. What would you do?

Now that you’ve answered, explore for a moment what showed up for you. What did you feel in your body? Did you feel uncomfortable? Attacked? How do you think that played into your reaction? 

Consider journaling on this if you feel called to.

This is an opportunity to see how you work in uncomfortable interpersonal situations. And in those situations, there are generally three options, each one with its own risks. 

1. You push back. 

2. You say ok, even if you don’t agree, and then resent the person who challenged you. 

3. You get curious.

When I was in this specific situation, at first I immediately did #2. This was a mistake. Then when that didn’t work and the investor continued to push, I did #1. Also a mistake. 

It took me years before I was ready to let go of winning or losing the battle, but I finally started to  get curious about how I could grow from this kind of seemingly impassible situation. Eventually, I learned to work more skillfully with uncomfortable interpersonal situations by letting go of resistance, opening up, and asking questions.

There are two ways this can play out. In the first way, you ask questions with the intention of trapping the other person. This is really just a passive aggressive version of #1. 

The second way is to hold fast to the unwavering belief that you will be successful, while simultaneously opening up to the opportunity that you might be missing something. Consider that maybe this uncomfortable, confrontational communication is just the thing to help you unlock the next level in your leadership (however you define that). 

We might wish that every investor had the EQ of a Brad Feld, but, in my experience, seagulls like the one in the hypothetical situation above are equally common (the average investor is probably somewhere in the middle). So the question isn’t if we’ll run into a guy like that. The question is when, and how we’ll work with that situation. 

Is the investor swooping in like this because he’s tone deaf? Because he doesn’t know what he doesn’t know? Because he’s stupid? Or is he applying pressure strategically because he believes that the CEO he’s talking to is talented enough to transmute that seemingly directionless pressure into exactly what’s needed to accelerate progress in whatever direction the company finds most useful? 

Does it matter? 

If you fight back, you are closed to new information. While you may win in the moment (or not), you will not grow from the experience, and if you stack enough of those together, eventually you will fail. 

If you simply say ok, you will lead your company down the chaotic path of executing against something you don’t fully understand/support, and you will surely fail. 

But if you ask questions, opening yourself to learn what this experience is here to teach you, without losing your grounding in your competence as a leader, every board meeting, and indeed every situation, is an opportunity to grow. 

The board meeting is not necessarily a friendly place. Nor, if you’re being honest, do you want it to be. Discomfort forces us to grow. In fact, all of startup life is one big confrontation with discomfort, and that’s a feature, not a bug. Startups are one big opportunity to see what you do when you’re outside your comfort zone. 

And how you react to being outside your comfort zone dictates the trajectory of your company and career. 

So how did you react to me playing the “angry seagull investor?” Are you willing to try on that even an unpleasant experience like that is here expressly for your individual and company growth? Are you willing to try on that our teachers come in infinite shapes and sizes, if we can only see them as such?

And if you are, what other angry seagulls are there in your life? What would it look like to get off the battleground, stop resisting or blindly accepting them, and instead get curious about how they might help you level up?

Want to dive deeper?

If you liked this, check out this list of my top posts, read and shared by thousands of entrepreneurs.

Here are a few of my favorites:

• The secret to leadership (why authentic leadership is simply more effective)

• How to fix your cofounder relationship in 3 difficult steps

• The five practices to transform from founder to CEO

• Finding purpose after exiting your company

• How to pitch a big vision to investors without setting yourself up to let people down

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