Change management is the difference between a game-changing tech rollout and an expensive piece of shelfware collecting dust.
I’ve bought a LOT of technology over the years—some wildly successful, others total flops. And every single time, one thing determined the outcome: how well I managed change.
As the executive buyer, I wasn’t just signing the check—I was responsible for ensuring configuration, deployment, and long-term success. Sometimes, that meant leading the charge myself. Other times, I had a CSM or a third-party partner run point. But either way, I had to own the outcome.
The $100K Bet
A few companies ago, I made a big bet. I pitched our CEO and CFO on a tool that would fundamentally change how our team managed customers and workflows. Price tag? Over $100K.
No pressure, right?
Not only did I need a rock-solid business case to justify the spend, but I also had to prove we could implement it successfully and drive adoption.
I had used this product before. I knew it inside and out. But familiarity wasn’t enough. Success hinged on my ability to drive real change in the business.
Here’s the playbook that made it happen:
1️⃣ Communicate Intentions Early & Often
Surprises are for birthday parties, not software rollouts. Before I even signed the contract, I started laying the groundwork.
Brought the idea to team meetings—multiple times
Shared insights from the evaluation process
Involved key ICs in early discussions to map workflows and features
2️⃣ Build an Inclusive Implementation Team
People want change to happen with them, not to them.
Asked for volunteers to help with configuration
Ensured the solution solved both frontline and executive needs
Delegated ownership—team members led specific parts of the rollout
3️⃣ Keep the Team in the Loop
Silence breeds skepticism. I made sure everyone knew what was happening, when, and why.
Dedicated 15 minutes in every team meeting to updates and questions
Made the project plan accessible to the entire team
Hosted an early demo before finalizing the setup
4️⃣ Train, Enable, and Support
A tool is only as good as the people using it. Adoption doesn’t happen by osmosis—it requires structured enablement.
Tailored training based on individual use cases
Established weekly Q&A sessions for ongoing support
Created feedback channels for reporting issues or concerns
5️⃣ Incentivize the Right Behavior
If you want adoption, tie it to what people already care about.
Linked OKRs and MBOs to adoption goals
Created team competitions & spiffs to reward early adopters
Used the software in live team meetings—leading by example
The Results? A Win for Everyone
The deployment wasn’t flawless (they never are), but it worked. The team adopted the tool, workflows improved, and we avoided the dreaded shelfware graveyard.
Lesson? Change Management Doesn’t Stop at Onboarding.
Whether you’re rolling out new tech inside your company or helping customers drive adoption of your product, the real work happens after onboarding.
Change is inevitable. Leading change? That’s where the magic happens.
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