Who's Deadheading
the Roses?

A few days before my daughter was born, I was nervous. Not nervous in a bad way. More like nervous excitement. The kind where you have way too much energy and absolutely nowhere useful to put it.

So naturally, I walked outside and decided the only course of action was an unreasonably large landscaping project.

Well, in reality, it started with me buying three roses. Her middle name was going to be Rose, and I thought it would be meaningful to plant three rose bushes before she was born. Three became six. Six became twelve. At some point, my wife probably should have taken away my credit card, because by the time my daughter arrived, I had planted around 40 roses.

The funny part is that we didn't even end up naming her Rose.

The roses, however, stayed, and apparently they told their friends, because today I have more than 100 of them around our property. Here's something nobody tells you when you're stress-buying roses days before the birth of your child:

100+
Roses to deadhead

Someone has to deadhead 100 roses.

Over and over, all throughout the growing season.

Every year, I hire someone to help maintain the property. And almost every year, some version of the same thing happens: someone comes out, walks the property with me, looks at the roses and understands exactly what I'm asking for. We talk about the work. They tell me how they'll take care of everything. We agree that maintaining the roses is part of it. Everyone is aligned.

Then the season starts.

The crew comes every week. They mow, they trim, they clean things up, but nobody deadheads the roses.

A month or two goes by and eventually I ask about it. The manager comes back out and they're usually genuinely surprised. “Wow. Yeah. This definitely should have been done.” The next day, someone comes out and deadheads them; “a special team.”

Problem solved.

Until two weeks later, when we're right back where we started. At this point, I'm not even complaining. I've mostly accepted that apparently owning 100 roses means I have accidentally taken on a second career in rose maintenance. But I've started thinking about why this keeps happening.

“The person who understood what I wanted wasn't the person doing the work.”

The salesperson wasn't lying to me. The manager isn't bad at their job. The crew isn't lazy. The problem is continuity. The person who understood what I wanted wasn't the person doing the work. The conversation we had at the beginning didn't become part of the system that governed delivery, and when something went wrong, the solution was another conversation rather than changing the system. That problem is much bigger than landscaping, and I've watched some version of it happen throughout my career:

  • Sales understands why the customer bought.
  • Delivery understands what they're supposed to build.
  • Executives understand the outcome they're expecting.
  • Technical teams understand the architecture.
  • Operations understands the process.

Everyone can be excellent at their individual job and the customer can still have a bad experience. Because the context gets lost between them.

And with AI, I think that problem becomes even more important.

We're asking organizations to build systems that increasingly cross departments, workflows, data and decision making. You can't have the sales team promising one thing, executives envisioning another, operators needing something different and developers building from an entirely separate understanding of the problem.

That's a big part of what we mean at Waifinder when we say Open by Design. It isn't just about transparency in how technology is built, it's about continuity.

The people defining the problem need to stay connected to the people building the solution. The people building it need access to the operators who actually live with the problem. Leadership needs visibility into what is being built, why decisions are being made and whether the original business outcome is actually being achieved.

Sales shouldn't throw something over the wall to delivery. Delivery shouldn't disappear into a black box. Technical teams shouldn't have to reverse engineer what the customer actually wanted.

And the customer shouldn't have to keep walking outside and asking:

Who's deadheading the roses?

Maybe we've accepted these gaps because they're so common that they feel inevitable, but I don't think they are. The next generation of services, especially AI services, shouldn't just deliver better technology. They should create better continuity between the people who understand the problem, the people who build the solution and the people who ultimately depend on the outcome.

Open by Design

That's Open by Design.

And yes, I still have more than 100 roses.

Apparently, I'm a gardener now.

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Waifinder helps organizations understand where AI can create real business value, and then builds the systems to make it happen.

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