Ryan Singer

Get Unstuck

If you need your team to move faster from idea to execution — and you don’t have time for mistakes — I can help.

Sometimes CPOs reach out to me because they are under pressure to hit an objective. There’s urgency from leadership to hit a target in the next year, and this requires the team to move faster and ship more. The CPO looks at team's current way of working and thinks: “we’re not going to get there like this.” Way too much time is wasted creating artifacts, going back to the drawing board, and having ritual meetings that don't move the project forward.

You may believe that a Shape Up way of working is the solution. But how do you actually get there? When you're under pressure to deliver, there isn't time to run experiments that don't pan out. And you can't take responsibility to shape everything yourself to make sure it goes well. The team needs the clarity and experience to do it themselves, so you can stay focused on strategy.

A pilot team

When you're under time pressure, you might think the fastest way to change is to kick off multiple teams in parallel working the new way. In my experience, this doesn't work. When multiple teams start from scratch in parallel, they each invent their own way of doing Shape Up. This leads to varying degrees of success, different conflicting opinions, and no unified answer to "how we work" when you onboard new hires.

To avoid all of that, I recommend starting with a pilot team. Hand-pick the people who are likely to do well and choose a project that has a meaningful win attached to it. With a couple loops in this controlled setting, you can work through the trial-and-error and arrive at a version of Shape Up that works in your org. After the pilot ships successfully, you have a model you can showcase internally and replicate.

An important role

The missing piece is usually who we call the "technical shaper." It's important to bring an engineer into the product team for shaping. Their qualifications are 1) senior-level credibility and knowledge of the system, 2) interest in the business objectives, and 3) the ability to take part in conversations where the problem definition is still being questioned.

In some teams, it's easy to identify this person. In other cases, I've seen CPOs bring in someone from outside as their first order of business before making process changes.

Make the first time a win

How much detail is right when shaping? What does the link from shaping to kicking off the build team look like? Who's the right person to involve at which step? How do you set expectations along the way? What are the hidden gotchas that you aren't thinking about?

The shortcut to answering these questions, changing the way you work, and building momentum — while shipping what the business needs — is to bring in someone who's done it before. I can work with you behind the scenes at the leadership level to select the pilot team and first project, guide the pilot team through framing, shaping, and kickoff, and be a backstop to solve problems and ensure the team is on track through every step.

If you're interested, reach out to me at rjs@ryansinger.co with a little background about what's going on. I'll reply with a calendar link to book a call. We can talk through the challenges you're facing and I'll suggest some different options to move forward.

© 2025 Ryan Singer