Don’t Let Perfection Block Progress: Leadership Lessons in Driving Transformation

Have you ever seen a transformation fail before it even started? It often isn’t because the vision was unclear. More often, it’s because the fear of getting it wrong kept the team stuck in place.

In any transformation, having a clear vision of where you want to go and what success looks like is critical. A shared vision acts as the north star, aligning teams and providing clarity on the “why” behind the change. Often, we draw inspiration from leaders we respect, businesses that have achieved similar outcomes, or past successes.

But here’s the truth: the path to achieving that vision is rarely a straight line.

What I’ve seen over and over is that teams—and even leaders—get stuck waiting for the perfect way to begin. They want flawless frameworks, ideal definitions, or fully developed systems before they take the first step. This focus on perfection blocks progress.

Transformation doesn’t require perfection. It requires courage, curiosity, and action. A journey of a thousand miles begins with a single step—and in transformation, that first step doesn’t have to be perfect. It just has to happen.

Vision Without Action Is Just a Dream

At AWS, we used a concept called “one-way doors” and “two-way doors” to encourage action and prevent paralysis.

• One-way doors are high-stakes decisions that are difficult or impossible to reverse. These decisions require 70% confidence that you’re making the right call—enough to feel deliberate but not paralyzed by over analysis. For example, a fundamental product pivot or a strategic pricing overhaul is a one-way door. These decisions carry lasting consequences and require thoughtful deliberation and buy-in.
• Two-way doors, on the other hand, are reversible decisions. These only require 50% confidence to move forward. They allow for experimentation because if the approach doesn’t work, you can step back and try something else. For instance, piloting a new customer engagement method or testing an alternative team structure is a two-way door.

Even within this framework, the emphasis is not on achieving perfection but on fostering experimentation and curiosity. The key is to act based on what you know today, learn from the outcomes, and adapt as needed.

This approach is invaluable in transformation because it empowers teams to move forward without waiting for perfect certainty. Leaders who adopt this mindset create momentum and build cultures that value progress and learning over hesitation.

Leading Transformation: Tackling Customer Renewal Risk

One transformation I'm leading involves shifting a team’s mindset from focusing on in-quarter deals to building an out-quarter view of customer renewal risk. For a team that has historically been reactive and short-term focused, this is a significant change.

The challenge is clear:

1. We lack a perfect definition of what “risk” meant for our customers.
2. There is no dedicated place in our systems to track this information.
3. Teams aren't used to thinking beyond the current quarter.

It would have been easy to wait—waiting for the perfect framework, the ideal tools, or consensus on the definition of risk. But waiting would have meant no progress. Instead, we took an iterative approach:

1. Start Small: We began with a high-level definition of risk based on three factors: customer recurring spend, product or service usage, and customer sentiment.
2. Leverage Workarounds: Without formal tools, we used spreadsheets and manual processes to track and prioritize at-risk accounts.
3. Learn and Improve: Each quarter, we refine the process. We adjusted the risk criteria based on new patterns and regression analysis, test better tracking tools, and adapt the process based on feedback from sales and customer success teams.

By starting imperfectly, we created momentum and gradually built a scalable process. More importantly, we transformed the team’s mindset—from reactive to proactive, from focusing solely on short-term deals to developing a strategic view of long-term customer health.

Had we waited for perfection, we would have remained stuck.

Transformation Thrives on Imperfect Action

The key to driving transformation is not knowing all the answers upfront. It’s about creating momentum and learning as you go. The benefit of frameworks like one-way and two-way doors—or of starting with imperfect solutions—is that they keep us curious and open to what we still have to learn.

Here’s the paradox:

• Even a one-way door only requires 70% confidence, which means there’s still room for ambiguity.
• A two-way door only needs 50% confidence, which is an invitation to experiment and adapt.

This is where leadership comes in. As leaders, our role is to:

• Create a safe environment where teams feel empowered to experiment, fail, and improve.
• Model the courage to take the first step, even when the path ahead is uncertain.
• Balance clarity of vision with flexibility in execution.

The cost, of course, is learning to live with ambiguity and tension. But that’s also the gift. Innovation and growth thrive in the space between having a clear vision and being open to what we learn along the way.

Call to Action

If you’re leading a transformation, ask yourself:

• Are you or your team waiting for perfection to take the first step?
• Can you identify whether the decision ahead is a one-way or two-way door?
• What’s one imperfect action you can take today to build momentum?

Progress doesn’t require perfection. It requires leadership. Start now, adjust as you go, and inspire your team to do the same.