This is the final post in my series on leadership. Up to now, I’ve been writing about how you lead—how you make decisions, how you think about the role, how you operate day to day. But there’s another side to this that gets easily overlooked, especially by first-time founders. It’s not just about how you lead. It’s about how you’re seen. When you move from being part of a team to leading one, something changes quickly. You’re no longer just doing your job—you’re being watched

This is the second of two posts on the subject of leadership and managerial control. In the first post, I focused on micromanagement. Here, I’m focusing on delegation—and how founders can move themselves out of that phase. For many founders, delegation feels uncomfortable. Delegation is often thought of as giving something up. You’re handing off responsibility, stepping away from decisions, and allowing someone else to take over a part of the business that you were previously

This is the first of two posts on the subject of leadership and managerial control. In this post, I’m going to focus on micromanagement—why it happens and why it’s so common in early-stage companies. In the next post, I’ll look at delegation and how founders can think about moving out of this phase. Micromanagement is one of the most common traits you see in early-stage founders. I was certainly guilty of it when I started my first company. From the outside, micromanaging loo

Layoffs are, without question, one of the worst experiences a founder will go through. Layoffs directly impact people’s lives—often people who were doing their jobs well. The worst part is that they often loved the work, the company, and their co-workers. For our purposes here, let's define a layoff as something that has nothing to do with performance. It’s the result of decisions you or your board or investors made, a business sale, or risks you took that didn’t work out. An

Customer churn is one of those things that every founder dreads—and for good reason. A customer leaving is a direct signal that something didn’t work. But if you treat it only as a loss, you miss the most valuable function it serves: diagnosis. Customers leave for a wide range of reasons, and most of them are fairly predictable, if you’re willing to look closely. Here’s a short list of the reasons that come to mind quickly: The product was oversold—it didn’t actually do what

Communication and Options) An important and vexing leadership challenge during a cash shortfall is communication. Who do you tell? How much information do you share, and when do you share it? Many founders hesitate to talk openly about financial pressure. They worry that employees will panic, that investors will lose confidence, or that customers will sense weakness. So they delay difficult conversations. Unfortunately, the longer you wait, the deeper the hole you dig for you

One of the most stressful moments in any early-stage company is realizing that cash is running out faster than expected. For founders, this moment often feels sudden. One day the company seems to be operating normally, and the next day the financial runway suddenly looks dangerously short. In reality, cash shortfalls are rarely sudden. They usually develop slowly over time, through a combination of optimistic assumptions, delayed revenue, unexpected expenses, or simple lack

In the previous post, I talked about gathering input when the information surrounding a decision is incomplete or conflicting. But eventually there comes a moment when a leader simply has to decide. When I’m weighing a decision, I usually start by examining the downside. I ask myself what the worst realistic outcome would be if the decision goes badly. Is the damage reversible? Can the company absorb a mistake? If the downside is survivable, the decision often becomes easier.

One of the harder aspects of leadership is making decisions when the information is incomplete. And because in early-stage companies you’re often doing things for the very first time, you don’t have precedents to look back on. Incomplete information is therefore often the default situation. You may be dealing with messy data or conflicting signals, and sometimes the information you need simply isn’t available within the timeframe you have, because a decision still has to be m

I’m going to shift my focus from sales to leadership for the next series of blog posts. There is a moment in every early-stage company when the founder’s greatest strength becomes the company’s biggest constraint. In the beginning, working in the business is exactly what’s required. You are either building the product yourself or working closely with a developer and/or a team. You are the one who sells to the first customers. You answer support tickets. You rewrite the pitch