Ryan, we have a problem!
- Jamie Schneiderman
- Oct 1, 2024
- 5 min read
Updated: Mar 18

I’ve known Ryan for over 10 years, we worked together in the past and have stayed in touch, connecting periodically and sharing ideas. He and I are very different, and I appreciate that he looks at things in a completely different way than I do. Over the past year and half, he has built an AI business that is breaking new ground. When he was first starting out, I got to see the MVP of the product. Many of the capabilities were awesome and blew me away. It wasn’t hard for him to attract other highly technical folks to work with him – they wanted to be part of something special.
Beyond the occasional text, we hadn’t connected much since he started the business. He was focused on his business, and I was focused on mine. I assumed that everything was going well and so I didn’t think too much of it when he reached out. It didn’t take long before it was clear that he needed my help.
The challenge
Ryan described a whole host of issues. He’s usually pretty calm and factual but his tone was anything but. There were issues with growth, product, sales, marketing and people. He vented and I listened.
Ryan has an incredible ability to build complex solutions. His technical acumen is off the charts. He always questions everything to make sure that every alternative has been considered and the rationale around decisions and the approach is sound. So, I knew when he started describing his challenge that he would have already tried several ways to solve it and that he was frustrated with a lack of a solution.
Time for a 5-3-1
Rather than trying to tackle each of the individual issues he was facing, I suggested that we take a step back to determine the root of his problems. My approach for doing that is a 5-3-1. It’s a framework to quickly identify and fix strategic issues that are often the root of these cascading problems. We work together to answer 5 critical questions and create an aligned strategic plan in 3 days.
What's the problem you're solving?
What's the customer that you're solving it for?
What's your solution?
What's the right strategic positioning?
What's the plan and execution to get there?
The ‘Problem’ revealed
I never know exactly where a 5-3-1 will take me and my client. I trust the process and know it will land the company in a much better place. It’s just hard to forecast exactly what the issues are and how to fix them before starting the process. I’m not going in with the answer. I’m going in with the right tools and the right people in the room to rapidly find and fix issues. So, it’s especially exciting when the issue pops up so clearly in the first session.
The first question we always answer in a 5-3-1 is “What problem are you solving?” I asked and boy did the room erupt in debate. Many of the participants (from Ryan’s leadership team) kept referring to the product and the solutions it offers. They are a team of technical geniuses and that’s their natural place to go. In fact, most companies I work with love to talk about their solution. But from my perspective, the solution is only valuable if you’re clear on the problem you’re solving for customers and these guys were not.
I pushed back repeatedly. Spending nearly an hour challenging each speaker on their POV with the same question “What problem are you solving?” Like I said, they are geniuses, but it took a little bit for the message to sink in. Eventually they realized I wasn’t going to back down and move forward with the process until we could clearly articulate the problem that they are solving. Another hour of debate and finally we locked in on the problem.
When I do a 5-3-1, I typically take a team through the first 3 questions on the first day. Those 3 represent the building blocks for the positioning and ultimately the plan. In this case, the first question was the hardest and took up a ton of time. The group exhausted their collective energy and patience getting to the answer and so we decided to break for the day (in total about 3 hours) and regroup to tackle the remaining 4 questions beginning the next morning.
There’s nothing like a bit of space to help people wrap their minds around challenges they are deeply into every day. When we got together on day 2, it was like I was working with a different group. The problem was now their foundation and every question we worked through came together quickly and clearly. They were all on the same page and moving fast – really fast. Normally, question 4 (strategic positioning) takes significant time to work through so I usually allocate the second day to working on it. But the group was now so aligned that we were able to tackle questions 2, 3 and 4 and left day 2 with clarity on the problem, the customer, the product direction and the positioning. They were now super jazzed to regroup for day 3 and build the plan to move forward.

“Why didn’t I see this?”
That evening, Ryan and I went out for dinner. I was surprised that he was so quiet and wondered what was bugging him. I asked what was wrong and he told me that he was super excited about where they were at in the process and moving forward on the business but was disappointed in himself that he couldn’t get the team there on his own. I tried explaining that the hardest thing to do when you’re in it every day is to poke your head out and see the whole picture without any bias. That’s the benefit of having someone else help to get you back on track.
Eventually, after about a half hour (and a few drinks) Ryan got over it and was back to focusing on what was next and how to build his game changing business.
Back on track
The next day we finished the last step of the 5-3-1 with the plans. Ryan and his team are off and running and I’m back to watching from a distance as they continue to innovate at a breakneck pace. I look forward to seeing Ryan’s picture on TV or on the front of some famous magazine and at least I’ll know I contributed my little part in helping him get there.

