Most major software transformations don't fail because of the technology. They fail because of leadership. The budget gets approved, the vendor gets selected, the go-live date gets circled on the calendar — and then executives step back, assuming their job is done. It isn't.
Leila Rookstool knows this firsthand. As a senior industry advisor at ServiceTitan with years of experience in commercial contracting — including leading enterprise-wide software adoption across Comfort Systems USA — she's seen what separates transformations that stick from those that quietly unravel. Her insight: adoption isn’t a technology problem. It's a leadership one.
Here are five steps executives can take to lead a major software change from decision through lasting adoption.
Step 1: Anchor the Change to Business Strategy, Not Technology
When Rookstool was tasked with rolling out a new selling system across Comfort Systems USA's operating companies, she made a deliberate choice: she never led with the software. She led with the problems it solved.
"I never put my selling cap on," she says. "I really just tried to position myself as their advocate — understand the real pain points it's solving for, and how it's going to address this gap and that gap."
The lesson: Your organization will adopt why long before they adopt what. Frame the change in the language of business outcomes — growth, efficiency, risk — not features and functionality.
Step 2: Build Alignment from the Bottom Up, Not the Top Down
One of the things Rookstool credits most for her success at Comfort Systems was the organization's deliberate, bottom-up approach to driving adoption — a principle she says was ingrained in her from the start and one she tried to embody throughout the process.
"You have a lot of visionary at the top, but part of what supports the success of a major enterprise like Comfort Systems is that corporate leadership is intentionally and continuously proofing these concepts with the local operating companies,” she explains. “That piece has to be aligned, especially within a more decentralized organization, for adoption to be successful."
The lesson: Leadership alignment isn't about cascading a message downward — it's about building genuine buy-in at every level before a rollout begins. In decentralized organizations especially, adoption follows trust, and trust is built through inclusion.
Step 3: Invest Early in Adoption, Not Just Implementation
One of Rookstool's clearest lessons learned: don't confuse a successful launch with successful adoption. The go-live date is not the finish line.
At Comfort Systems, onboarding would run smoothly — and then the ongoing work would get left behind. New salespeople joined. Internal expertise walked out the door. Nobody was maintaining momentum.
"Don't forget the after part," she says. "They continuously have new people coming on board and don't have an internal subject matter expert to train them. That was a gap."
The lesson: Executives should budget accordingly — not just for implementation, but for continuous enablement, training reinforcement, and someone dedicated to keeping adoption alive after launch day.
Step 4: Normalize Discomfort and Communicate Through It
When Rookstool noticed blank stares during a presentation, she didn't push harder. She got curious.
"If I received blank stares or limited feedback, I always took that as a personal note — I'm not fully explaining this vision in a way that resonates," she says. "So that would result in more questions."
She'd go back to trusted leaders, run small focus groups, and rebuild her message from the ground up based on what she heard. Her rule during moments of friction: transparency over polish.
"I have found that most leaders, particularly within this industry, really just prefer the most direct, transparent answer when walking through those situations."
The lesson: Executives who communicate clearly — even when the answers aren't perfect — build the kind of trust that keeps organizations moving through the discomfort of change.
Step 5: Measure, Reinforce, and Recommit
For Rookstool, an executive who thinks their job ends at launch is an executive who has misunderstood their job entirely.
"If you leave it unattended, that's just part of what might erode things for a business as a leader," she says. "Continuously staying attentive to the success of that rollout is just as pivotal as seeing a successful rollout."
The lesson: Establish benchmarks before you begin, and measure against them consistently — both quantitatively and qualitatively. Then tell that story of progress across the organization.
"People want to see real tangibles in terms of how these things are going to benefit their business. You have to know where you started and where you are today."
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What We Know Now
Rookstool's experience at Comfort Systems — where she achieved 90% adoption across a large, decentralized enterprise — wasn't the result of pressure or mandates. It was the result of trust, transparency, and treating adoption as an ongoing leadership responsibility, not a one-time project milestone.
Change is inevitable. Adoption is a choice — and it starts at the top.
