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

This is going to be my final post for a while on the subject of software and product demos, but it's perhaps the most important one. And it’s about the debate I had for years with my own team about the very nature of a product demo.  Let’s say your salesperson has done the discovery. They understand the buyer’s situation. And your product has 30 (or maybe 300) features. The customer has explained that there are two or three features that really matter.  So how much do you sho

I've been writing about the value and process of demos. But before you even get to a demo, there’s the question of whether to have a discovery call first. Some believe discovery is mandatory in all cases. Others argue that it slows things down and adds an unnecessary barrier. There isn’t a universal right answer. There is only what makes sense for your product, your buyer, and the size of the decision you’re asking someone to make. For instance, if you’re selling a $49-per-mo

I can’t tell you how many times I’ve been on a software demo where the salesperson introduces the company, gives a bit of history, sets some high-level context, and then starts clicking through the product. Feature after feature, they explain it in a formulaic, rehearsed way. These demos don’t usually fail because the product is bad. They fail because nothing meaningful is learned, and no business problem is identified.  And yet—why does this happen?   The all too common beli

In Part 1, my argument was that effective sales depends on where expertise lives. When a salesperson demonstrates real understanding of a buyer’s business, the conversation shifts from transactional to advisory. What matters next is what that shift makes possible. Once a buyer recognizes that the person across the table understands their business context—not just the product being sold—the nature of the conversation changes. The salesperson is no longer heard as a vendor resp

One of the most misunderstood ideas in sales is where expertise is supposed to live. Some assume the prospect is the expert and the salesperson’s job is simply to explain a product clearly and answer questions. But that’s backwards.  In effective sales, especially in complex or early-stage markets, the salesperson should know as much as, or even more than, the buyer about the buyer’s business. The best salespeople have been selling into the same industry for years, and they

I look at a lot of early-stage startup websites. Some are better than others. But the ones that focus almost entirely on explaining what the product does tend to drive me a little crazy. The site lists features. It explains how the product works and why it’s different than the competition. As a result, the website often reads like an internal document that’s been made public. What it doesn’t explain is what the customer actually gets. There’s a big difference between describi

There’s a common way we think about sales and marketing that causes real problems,, especially in early-stage companies: We tend to treat them as separate functions. Marketing’s job is to come up with strategy and create materials: copy, visuals, stories meant to attract a prospect’s attention. Sales then picks up from there, talks to prospects, and eventually tries to close the deal. The mistake is putting an iron wall between the two. Sales and marketing aren’t separate a

From time to time, I fill out the “contact us” form on a website simply because I’m curious. I may want to understand what a product does, how it works, or just see what’s new out there. That doesn’t mean I have a problem I’m actively trying to solve. Often, I don’t. Those curiosity-driven inquiries can feel a lot like traction on the receiving end. People book demo calls. They ask thoughtful questions. They seem engaged. For an early-stage company, that activity can feel enc

Early traction feels very different depending on how sales is handled. If you’re a solo founder doing your own selling, you hear the friction directly. You’re listening carefully to feedback and trying to understand whether your product or service is actually solving a meaningful business problem. You can feel where conversations take off—and where they stall. The information is direct because you’re close to the source. But once sales is delegated—to a sales leader or a team

As a founder, I paid close attention to the idea that when an employee clearly isn’t working out, the kindest and most effective thing to do is to make a decision quickly—and act on it. Dragging things out with performance plans and repeated second chances rarely helps. It’s awkward, and it usually just prolongs uncertainty for both the organization and the person. I see founders do something very similar with early early stage company marketing. If a marketing approach isn’t

I want to return to the question of pricing, because it’s one of the hardest parts of marketing to get right. Pricing is often treated as a technical problem, but in practice it’s as much cultural and psychological as it is analytical. Economists will tell you that buyers behave rationally. In the real world, they don’t. Customers bring habits, expectations, industry norms, and internal politics into every pricing conversation. Add negotiation on top of that, and it becomes v

I had a call last week with a founder that centered on when to talk about price. He sells into a highly price-sensitive market, which means the question comes up early in many of his sales conversations. My view is that it’s almost always a mistake to talk about pricing upfront. Until you’ve taken the time to understand the prospect’s business and what’s actually not working, there isn’t much of a real price conversation to have. We’ve all heard this before: “They liked it, b

High-quality leads are (unfortunately) all too rare—and they’re almost never defined by a prospect’s title, company size, or how they found you. The best leads can articulate a real business problem in their own words. They don’t need to be convinced the problem matters. There’s already pressure inside their organization to do something about it. Ideally, they can also explain what happens if nothing changes. If a lead like this comes in (and your product can genuinely addres