It was the middle of Covid. Our entire company was remote, everyone was Zoom-fatigued, and my boss asked me to plan a team event.
I stared at the assignment. A team event. Online. For people who had spent the last year trapped in video calls and were thoroughly, completely done with screens. I had no idea where to start.
Then my boss said five words that changed how I approach every project since: "Here's what success looks like."
He didn't give me a budget range. He didn't suggest a platform. He didn't hand me a list of past events that worked. He painted a picture in two words: People are delighted.
Not "people attend." Not "people say it was fine." Delighted.
That single word reframed the entire problem. A trivia night on Zoom? People would attend. They would not be delighted. A virtual happy hour? People would show up, make small talk, and quietly check their phones. Not delight. A guest speaker? Informative, maybe. Delightful? Unlikely.
So I kept searching. And eventually I found Anjl, a comedian turned painter who had reinvented herself during Covid as an online painting instructor. A kind of irreverent Bob Ross, guiding groups through mountain landscapes while cracking jokes the whole time.
We booked her for our company's three-year anniversary. Anjl shipped paint kits to everyone's houses. We shipped bottles of wine. And on the night of the event, our entire team (engineers, ops, leadership) sat in their kitchens painting a mountain at night, laughing at Anjl's running commentary, holding up their canvases to the camera.
Turns out, we were a company full of Bob Ross fans who never knew it. People weren't just delighted. They were surprised at how delighted they were. It was the best team event we'd ever had, on the platform everyone was sick of, during a year when nothing was supposed to be fun.
That happened because my boss didn't tell me what to build. He told me what success looked like. And the picture was specific enough that I could reject every option that didn't match it.
He didn't tell me what to build. He told me what success looked like. That's not the same thing.
The Question Nobody Asks
I've spent over twenty years building and running businesses, and I can tell you that the majority of wasted effort, wasted money, and wasted argument comes from one source: nobody defined success before the work began.
This is what usually happens instead. Someone says "we need to improve our customer onboarding." The team nods. People start working. One person redesigns the welcome email. Another builds a tutorial video. A third rewrites the FAQ page. Everyone is busy. Everyone is contributing. And three weeks later, someone asks the obvious question: wait, are we trying to reduce support tickets, or are we trying to make new customers feel confident?
Those are different goals. They lead to different work. But because nobody painted the picture, the team optimized for three different versions of success simultaneously, achieving none of them cleanly.
This happens in businesses of every size, every day. Not because people are careless, but because starting feels more productive than defining. The pull to begin is stronger than the discipline to aim first.
If you don't define the target, people will invent their own. And they won't all invent the same one.
What Doesn't Matter
My boss doesn't just define success. He names what doesn't matter. And that's the part most people skip entirely: the part where the real waste hides.
When you tell your team "success looks like X," you've pointed them at the target. But when you also say "and here's what we're not optimizing for," you've cleared the runway. You've given them permission to stop polishing things that don't move the needle.
I learned this the hard way at my own company. At Calico Spanish, I'd spend weeks perfecting a product launch (the graphic design, the email sequence, the landing page layout) when the actual success metric was whether teachers could open the materials and use them on Monday morning. The design didn't matter. The usability mattered. But I'd never said that out loud, so I optimized for the wrong thing.
I caught myself doing it again recently. I was laboring over the formatting of a planning document (the presentation, the layout) when the deliverable was the plan itself. The formatting didn't matter. The thinking mattered. I was spending effort on something nobody asked for, because I hadn't asked myself what success looked like for that specific task.
We all do this. The question is whether we catch it before or after the hours are spent.
The Framework: Define Success Before You Build
1. What does success look like?
Name it in concrete, observable terms. Not "improve customer experience." That's a category, not a picture. Try: "Customers complete onboarding without contacting support." Or simply: "People are delighted." Specific enough to measure. Simple enough to remember.
2. What does failure look like?
Name the version of the project that technically ships but doesn't solve the problem. Often the failure state is "we built something polished that nobody uses," or "people attended but nobody was delighted." Say it out loud so the team can recognize it if they're drifting.
3. What doesn't matter?
This is the question that eliminates the most waste. Say it explicitly: "The design doesn't matter at this stage." "Speed matters more than completeness." "We're not trying to impress; we're trying to learn." Give your team permission to stop perfecting things that don't move the needle.
Why This Is the First Question in Any AI Implementation
Most businesses that stall on AI adoption aren't failing at the technology. They're failing at this question. They invest in an AI chatbot without defining whether success means faster responses or happier customers. They automate email campaigns without deciding whether success is more volume or better conversion. They deploy reporting dashboards without clarifying whether anyone will actually read the reports.
The tool works. The implementation fails. Not because the technology was wrong, but because nobody painted the picture of success before the budget was spent.
At Build Tenacity, this is where we always start. Before we recommend a single tool, we ask: what does success look like for your business? What does failure look like? And, critically, what doesn't matter?
A chatbot that responds in two seconds but leaves customers frustrated is optimizing for the wrong picture. A reporting dashboard that's beautiful but unread is a failure state nobody named. An automation that saves ten hours a week but kills the personal touch your customers love is a trade-off nobody discussed.
Define the picture first. Then pick the tool.
That painting class was years ago. I still think about it, not because it was a great event (though it was). Because it taught me that the right answer was hiding behind a question I almost didn't ask.
If my boss had said "plan a virtual event," I would have booked a trivia night and called it done. Instead he said "people are delighted," and I had to keep searching until I found something that actually matched the picture. The constraint wasn't limiting. It was liberating. It told me when to stop looking.
Try it on your next project. Before anyone opens a laptop, say the five words out loud: here's what success looks like. Watch what happens to the clarity in the room.
"The most expensive work in any business is the work that didn't need to be done. Define success before you build, and give your team permission to ignore everything else."