#22: Blossom in the shadows. 3 questions to create momentum for org change
I am going to share two stories about driving organizational change, one success and one failure, along with 3 key questions to help you pick the right internal partners and build momentum for your change initiative.
The success? How we infused design thinking into Capital One.
The failure? What went wrong during a $1 billion digital transformation.
The lesson? Don’t chase splashy, high-profile initiatives. Instead, focus on blossoming in the shadows - inside overlooked areas of your organization where experimentation thrives, learning happens, and momentum builds.
Let me show you how.
why changing how we work is so hard
Changing the way people work in large organizations is hard.
Whether it’s introducing a new mindset, a groundbreaking tool, or an entirely different way of working, you’ll face uncertainty. You might worry that your idea will fail before it even gets off the ground.
The truth is, starting change successfully requires finding the right environment to experiment—one that gives you room to learn and adapt without the pressure of immediate, large-scale results.
unfortunately, most people approach change in the wrong way.
They aim too high, targeting big, visible projects with too much at stake. They think more resources and attention will lead to better outcomes.
But in reality, this often creates the opposite effect - fear of failure, layers of bureaucracy and endless stakeholder management.
the #1 mistake: starting too big
Instead of prioritizing experimentation, many people chase projects that are:
High-profile and high-risk - where failure isn’t an option.
Packed with stakeholders who resist new approaches.
Tied to rigid timelines, making flexibility impossible.
Lacking leaders who genuinely believe in the change.
But here’s the good news: change doesn’t need to start big to create big results.
You can take steps right now to build momentum, test new methods, and set yourself up for lasting success.
instead, ask these 3 questions
Is the initiative low-stakes?
Is the leader an advocate who’s open to experimenting?
Is the working team willing to try something new?
3-QUESTION CHECKLIST TO IDENTIFY WHERE TO PLACE BETS
#1. Is the initiative low-stakes?
Why it matters: Low-profile, unsexy projects give you breathing room to learn, iterate, and deliver results without the fear of high-stakes failure.
Example: At Capital One, we faced a pivotal decision - choosing between two projects:
Option A: A high-profile, fully-resourced project on bank rewards—visible, important, and packed with expectations.
Option B: A low-profile project with a senior executive who was willing to take a gamble.
We picked Option B because it gave us the freedom to test ideas, fail fast, and learn without the pressure of immediate success.
Actions you can take:
Look for stagnant business units where any improvement is a win.
Identify pet projects from senior leaders who want to experiment.
Target underserved teams that are open to trying something new.
#2. Is the leader an advocate who’s open to experimenting?
Why it matters: Advocates create safety. They allow you to take risks, experiment, and learn from failure without fear of judgment.
Example: The Capital One project worked because our senior executive sponsor was willing to take a gamble and experiment with us. That support gave us the space to learn and eventually prove the impact of design thinking.
Contrast that with the $1 billion digital transformation I worked on, where the initiative was top-down, too big to fail, and required approvals from 8 VPs. Each one had competing priorities and conflicting approaches, leaving us stuck in endless debates.
In the end, we spent more time managing expectations than actually testing and learning.
Actions you can take:
Build relationships with leaders who:
Believe in your vision.
Are open to experimentation.
Have influence to protect and promote your work.
#3. Is the working team willing to try something new?
Why it matters: A change effort is only as strong as the team behind it.
Example: In the $1 billion transformation, my team had a ton of ideas—but we hadn’t tested them yet. And we were surrounded by stakeholders who resisted experimentation and wanted clear, proven solutions from the start.
Compare that to the Capital One project, where we hand-picked curious, adaptable team members who leaned into trying new approaches—even when we didn’t have all the answers.
Actions you can take:
Look for teams that:
Lean into learning. Are they open to testing ideas and learning from mistakes?
Collaborate well. Do they say, “Let’s try it” instead of “We’ve never done it that way”?
Bring energy. Are they excited to experiment and co-create solutions?
Pro Tip: If the team’s mindset feels stuck, shift it with workshops or even smaller, low-risk experiments before diving into bigger changes.
summary
The secret to lasting organizational change isn’t starting big—it’s starting small.
At Capital One, we started with low-stakes bets and open-minded advocates—and it worked.
In the $1 billion transformation, we started too big, with too many stakeholders—and it didn’t.
The lesson?
Find your advocates. Pick the unsexy project. Blossom in the shadows.