Make It Easy

August 8, 2026

“Hard work is inevitable. Unnecessary work is optional.”

This week, I found myself thinking about friction.

Not the kind that makes hard things hard. Some things are supposed to require effort. Building a company is hard. Teaching children is hard. Leading people is hard. Selling something worth buying is hard. Those are the things that matter, and they’re supposed to require work.

What I’ve been thinking about is everything else. The unnecessary work we create around those things. The meetings that don’t need to happen. The forms that don’t need to exist. The delays, approvals, and processes that make it harder for customers to move forward. That’s the kind of friction I’m talking about.

I don’t think I really understood friction until I became responsible for marketing, strategy, sales enablement, and ultimately the growth of a large business. Up to that point, much of my career had been about building great teams, solving hard problems, and making good decisions. Then my job changed. Suddenly, I wasn’t just responsible for whether we had a great product. I was responsible for whether customers could actually get to “yes.”

That shift changed the questions I asked.

Instead of asking whether we had enough opportunities in the pipeline, I started asking how easy we were making it for customers to move through it. If they needed to integrate with their existing systems, how easy did we make that? If they needed a contract, how many obstacles did we put in front of them? If they wanted to understand our pricing, did we explain it clearly and help them figure it out? If they wanted to talk with another customer, could we connect with them quickly? If they had a data privacy question, did we already have the answer waiting for them?

Somewhere along the way I stopped thinking only about pipeline and started thinking about pipeline velocity.

There’s a subtle but important difference. A pipeline tells you what opportunities exist. Pipeline velocity tells you how efficiently customers are moving through those opportunities. When I started looking at the business through that lens, I became almost obsessed with finding the places where customers slowed down.

Where are deals getting stuck? What question keeps coming up? What objection haven’t we answered? What internal process is making customers wait? What information could we provide earlier so the objection never becomes an objection in the first place?

Once you start asking those questions, patterns begin to emerge.

Sometimes the blocker is surprisingly simple. I’ve worked in organizations where customers misunderstood our pricing or weren’t sure how our business model worked. We knew the answers, but we weren’t explaining them particularly well. Better messaging didn’t change the product. Better sales enablement didn’t change the product. They simply made it easier for customers to understand the value we were already delivering.

Other times the friction appears farther down the funnel. Maybe customers consistently have the same data privacy concern. Maybe they need the right purchasing cooperative or contract vehicle for their state. Maybe your contracting process takes three weeks when it should take three days. Maybe customers want to integrate with a system they already use, but your answer is, “That’s not how we do it.”

None of those things feels particularly significant by itself. But friction compounds. One extra meeting probably doesn’t kill a deal. Neither does an extra form, an unanswered email, a confusing proposal, or waiting several days for a response. Stack enough of those moments together, though, and eventually another company shows up that simply makes the decision easier.

I think that’s where organizations sometimes get it backward. We build processes around what’s easiest for us instead of what’s easiest for the customer.

I’ve seen companies standardize around a single integration because it’s operationally simpler. I understand why. I’ve run a P&L. Supporting fewer systems costs less. Engineering becomes simpler. Support becomes easier. Contracts become more standardized.

But customers don’t care about your organizational convenience.

Schools already have systems. They already have processes. They have limited staff, limited budgets, and even more limited time. If buying your product requires them to redesign their environment around the way you prefer to operate, you’ve created friction before they’ve received any value.

That doesn’t mean you say yes to every request. Good businesses have to understand margins, scalability, and where to draw the line. Some customers simply aren’t the right fit. But there’s a big difference between saying no because something isn’t good for the business and saying no because, “That’s the way we’ve always done it.”

I learned a lot about this during my time at Amazon.

Amazon spent decades removing steps between I want that and I have that. Prime is an obvious example. So is Amazon Go. The technology behind those experiences is incredibly sophisticated, but the customer experience feels almost effortless.

That’s an important distinction.

Simple for the customer rarely means simple behind the scenes. In fact, it usually means someone inside the organization worked incredibly hard to absorb that complexity before the customer ever experienced it.

I was reminded of that this week at the ranch.

I needed to install a new float bucket for one of the horses we board here. That meant I needed a bucket, a hose, and a handful of fittings. There’s a local farm store I genuinely enjoy visiting. They know us. They’re great people. Sully gets treats every time we walk through the door, and if I have the time, I’d much rather spend my money there.

But this week was busy, and I honestly didn’t know when I’d be able to make the trip.

A few clicks later everything I needed was on its way, and I could spend my afternoon installing the bucket instead of driving across town. It wasn’t a decision about loyalty. It was a decision about friction. The easier option won.

Customers make that same decision every single day.

That’s why I’ve come to believe friction is less of a technology problem than it is a leadership problem. The best leaders absorb complexity so customers don’t have to.

Sometimes that means asking engineering to build another integration. Sometimes it means asking legal to simplify contracting. Sometimes it means investing in better documentation, better messaging, or better training. Sometimes it simply means telling your own organization that what’s easiest for us isn’t what’s best for the customer.

I’ve been on the other side of that equation too. As a Chief Technology Officer, there were times we intentionally moved away from technologies my own team knew extremely well because another solution would ultimately create less friction for thousands of teachers and staff members. Those weren’t always comfortable conversations. People had invested years becoming experts in the existing environment.

Leadership meant helping my team through that transition because it was the right decision for the organization.

If I were sitting with a CEO today, I wouldn’t start by asking how big the pipeline is. I’d start by asking how fast it’s moving because pipeline flow matters just as much as pipeline size.

Then I’d walk the customer journey from the first conversation all the way to a signed contract and look for every place customers consistently slow down. Every unnecessary meeting. Every unanswered question. Every confusing process. Every avoidable delay.

Those aren’t isolated problems. They’re friction. And friction is cumulative.

Around the ranch, there’s already enough hard work to do. Fences have to be repaired. Hay has to be moved. Horses have to be fed. There’s no reason to create extra work that never needed to exist in the first place.

Business isn’t much different.

The goal isn’t to eliminate the hard work.

The goal is to eliminate everything that gets in the way of it.

Hard work is inevitable.

Unnecessary work is optional.

Make it easy.