How Can I Help?

I am not a technologist. This surprises many, including a CEO I was on the phone with recently. I explained that I had no pet software projects I was working on at home, and thus couldn’t demo her software. She paused for a second, like, “Uh, why are we on the phone, then?”

It’s true that I have worked on tech since graduating from college, and that I wrote Puppet essentially alone while I bootstrapped the company for years by myself. I enjoyed the work, but those were all a means to an end, not the goal. This became more and more clear to me as I hired large teams who really were technologists. I was able to do the work, but they loved it. I naturally fell into different, complementary areas.

So no, I can’t really help your company in sorting out its software stack. Or rather, I could, but you really shouldn’t want my help there. There are better people. Far better. People have found my advice really helpful in the past, but not in this area.

Strategy is where I’ve had the biggest effect as an advisor. You are already deeply committed to your goals - you don’t need my help figuring out what to do. You are just as committed to how you’re going to achieve them, but probably haven’t spent as much energy thinking about it and expressing it. This ‘how’ is your strategy, and key aspects are decided early on, whether you mean to or not.

Do you want a big field sales force, or a self-service model? Either way, why? How does that choice affect your product price point and service attach rate? There isn’t necessarily a right or wrong answer, but a choice will be made, and it has massive consequences on the life of your company. My great ability is pestering you with questions until you’re forced to put your opinions on the table and really examine them. As a leader, your job isn’t just to be opinionated - it’s to be able to usefully express that opinion to your team.

Product is the second major area I will push you. Again, this isn’t about the tech, or the code. I don’t care how it’s built. The first step is being clear about what problem you want users to hire you for. I bet you have a decent grasp of this, but you have to go down a layer into which users you’re going to start with, how you’re going to parlay them into a larger group, and how all of that relates to adoption within a single organization and across a market. The path of a product’s adoption is as critical to plan out as the features you build.

All of that ties into how you price. How does it drive user behavior? What do you want to incentivize through low or free pricing, and what must you charge for to make your business work? How does charging per seat vs consumption vs features change their behavior and affect your business?

All of this must come together into a coherent system that pushes you, your team, your customers, and the market to focus on the right problems at the right time. You should seek my help in seeing the whole system, and especially the gaps in it. I hate software, but oh boy, do I love systems. My brain is so optimized for managing, storing, and assessing systems that I lose nouns constantly. It’s worth it, for me and for you.

I can also help you.

You’re not a coincidence. You have to understand, it’s not an accident that you’re here. Even if the only thing that makes you special is that you were the first one to raise your hand… it’s been a few years now. Because of that one little action, you’re different than everyone else. It’s up to you to demonstrate whether that difference is good, or useful, but it’s definitely there.

I don’t mean to say that you’re better, or that only certain people can be entrepreneurs. History shows the exact opposite, and I’m a huge believer in empowering ever more. What I mean is, the mere act of taking the step permanently changed you. One of the hardest acts for most founders, especially those from underrepresented groups, is believing that they belong, that they deserve to be out front. I can help you see how just sitting in the seat has led you to be a different person than you were before, led you to special insight and special opportunity.

It’s up to you, now, to make the most of the opportunity, to believe in it and to deliver on it. You have to learn how to extract that difference, to bottle it, to share it. And when to dump it down the sink.

Founders are so full of dreams that they have a hard time letting go. “It’s true we can’t do this today, but I’m going to keep talking about it in hopes we can do it tomorrow.” Your business is on death’s door and the wrong success gets you all fired, but sure, go ahead and distract your team with something you know you can’t and shouldn’t build, and that your customers would never buy.

Everyone knows founders have to make hard decisions, but most don’t seem to realize the hardest ones are about their own dreams. To build something great, you have to give up on other dreams. You can’t build it all at once. You can still hold it, treasure it. But you don’t get to talk about it. You can’t distract people with it.

You haven’t earned it yet. When your company is a massive success, and throwing off more cash than you know what to do with, that’s when you pull out your other great ideas and turn your success into a platform for experimentation. Until then, you have to focus. Let go.

Beyond all that, I enjoy working through demos and user experiences, helping people see your work through new but educated eyes, asking a thousand questions that you might not have answers to. This teaches us both a lot about you, your product, and your company. The differences between the easy and hard answers teach you a lot, too.

What I don’t like to do is tell people what to do. At most, I will share frameworks I’ve used for decision-making in the past and recommend some of them for you, but preferably, I will focus on pulling from you what you really believe, and then make you really confront it. It’s not about me. I can’t live your life. I don’t know your customers. I can’t run your company.

But maybe, with the right prompting, I can help you look at it in a new light, help you make the right decisions faster, and help you avoid some of the worst parts of this insane decision you’ve made.