When I first heard Kailey Alongi describe Adobe’s old coaching landscape as “the wild west,” I laughed, because I’ve been inside organizations where that exact phrase applied. Too many leaders requesting coaching without clarity. Too many vendors. Too many mismatched approaches. Too many well-intentioned programs without a strategy or a North Star.
Coaching can so easily become scattered, inconsistent, and invisible. And when that happens, organizations lose the very thing they’re trying to build: a leadership culture where people feel supported, developed, and seen.
That’s why this conversation with Eric Wong and Kailey Alongi, two of my partners at Adobe, felt so important. Adobe made a conscious decision to shift away from ad-hoc coaching to something more strategic, more human, and more measurable. Their journey represents exactly what’s possible when organizations stop treating coaching as a perk or a fix and start treating it as a lever for organizational transformation.
This blog is a deeper reflection on our conversation, an expansion of the ideas, tensions, and possibilities that surfaced. It’s also a call to action for any organization asking the same questions so many executives whisper to me behind closed doors:
How do we know when to bring in coaching? How do we measure it? How do we make it accessible? How do we keep it from becoming chaos?
Let’s explore what’s possible when coaching is done with intention.
The Shift From “Anyone Who Asks Gets a Coach” to a Real Strategy
Most companies start the same way: leaders request coaching because they’ve heard it’s useful, or because someone is struggling, or because it’s simply what high performers expect. Before long, HR is juggling dozens of engagements with no standard approach, no common goals, and no meaningful way to understand impact.
Adobe was no different, until Kailey and team decided it was time to get serious. They asked the questions every organization eventually must ask: Who is coaching really for? What are we trying to change or accelerate?What outcomes matter?
Instead of letting coaching requests come in from every direction, Adobe began designing a targeted ecosystem: specific audiences, clear criteria, measurable objectives, and manager involvement from the start. Coaching became something deployed thoughtfully, akin to the right prescription for the right diagnosis, not over-the-counter medicine for everything.
This shift was the foundation for everything that followed.
The ROI Question: Yes, It Can Be Measured (If You Know What Matters)
One of the most common questions I get from executives is, “How do we prove coaching is working?” They mean financial ROI, of course, but leadership growth is rarely that linear.
What Eric and Kailey emphasized is that ROI becomes measurable when you’re looking at the right markers. At Adobe, their analytics team tracks leader outcomes longitudinally, engagement, promotion rates, team health, mobility, and compares them across cohorts. They pay attention to behavior change, manager observations, confidence shifts, and team-level performance indicators. They evaluate coaching not as a short-term “fix” but as a contributor to long-term leadership trajectory.
That’s what so many organizations miss: coaching ROI is not a single metric.
It’s a pattern. A progression. A ripple.
And those ripples are most visible when the entire ecosystem around the leader is aligned.
Which leads to one of my favorite themes from the conversation…
Manager Involvement Isn’t Optional, It’s the Glue
I’ve seen exceptional coaching derailed simply because the manager wasn’t involved. I’ve also seen mediocre coaching become transformative because the manager was deeply engaged.
Eric put it perfectly: “If managers aren’t aligned, the coaching can drift in the wrong direction.”
When managers are present at intake, aligned on goals, reinforcing behaviors, and helping to contextualize progress, everything accelerates. When they’re not, coaching becomes a parallel universe, great reflections but limited application.
Manager involvement is the difference between insights that sit in a notebook and insights that reshape a career.
The Future of Coaching Is Hybrid, Human, and Democratized
One of the most exciting developments in Adobe’s journey is the expansion of coaching-like support beyond the traditional one-on-one model. Not everyone needs a coach. Not everyone is ready for a coach. And not everyone will get budget for a coach.
But everyone deserves to feel developed.
Kailey described a new approach inside Adobe that blends AI nudges, self-guided lessons, and short coaching sessions, creating access points for employees who historically would never have been eligible. It’s coaching principles delivered at scale, without diluting quality or intention.
In many ways, this democratization is reshaping the leadership development landscape. Coaching no longer has to be an exclusive experience for a select few. Small doses of reflection, awareness, and behavioral reinforcement can unlock change across the entire workforce.
This is what I mean when I say coaching is not a perk, it’s a culture where people feel invested in, where development is continuous, and where growth is not gatekept.
And most importantly: it’s a culture where leadership is not defined by level but by mindset.
Executive Presence, Authenticity, and the Invisible Wins
Another moment that stuck with me came from Kailey’s definition of executive presence. She said: “Executive presence isn’t loud. It’s not animated. It’s being comfortable in your own skin.”
This matters because leaders often assume presence is something they have to perform, a style they need to adopt, a persona they need to mimic. But coaching at its best strips away performance and strengthens authenticity.
Eric shared an example of a leader who finally owned his introversion, simplicity, and quiet clarity, and suddenly became more influential.
That’s the invisible work of coaching: the inner shift that produces outer impact.
Authenticity is not a soft skill. It’s a leadership accelerator.
And organizations that understand this create development programs that embrace the whole human, not just the competencies on a model.
What Organizations Need to Get Right When Scaling Coaching
To bring this all together, here are the key actionable steps organizations can take when designing or refining their coaching strategy, distilled from our conversation and from years of doing this work inside complex systems:
Actionable Steps for Organizations
- Define your coaching philosophy and North Star.
Get crystal clear on who coaching is for, why you invest, and what success looks like. - Pair coaching with manager alignment.
Make manager participation part of the process, not an optional extra. - Measure what matters, not what’s easy.
Look beyond satisfaction surveys to track behavior change, team impact, and progression over time. - Create tiered development pathways.
Offer bite-sized coaching, nudges, and community learning so development doesn’t become a privilege for the few. - Deploy coaching proactively, not reactively.
Use coaching to stretch your strongest leaders, not to triage performance issues. - Blend human wisdom with data and technology.
Leverage analytics and AI responsibly to enhance, not replace, the relational work of coaching.
Coaching Done Well Isn’t Random, It’s Transformative
The story Eric and Kailey shared isn’t just about Adobe.
It’s a model for what’s possible when coaching becomes strategic, intentional, and human-centered.
Coaching is at its most powerful when the organization has a point of view.
When the system around the leader is aligned.
When managers are engaged.
When data is used for insight rather than oversight.
When development is available at multiple levels, in multiple forms.
When authenticity, not imitation, is the goal.
And when coaching acts not as a Band-Aid but as a catalyst.
If there’s one message I hope leaders take from this conversation, it’s this: Coaching can be your organization’s most powerful engine for growth, but only if it’s designed with clarity and empathy.
When you invest in leaders intentionally, everything shifts: trust deepens, teams strengthen, and performance accelerates in ways no one-off workshop ever could.That’s the future of leadership development. That’s what’s possible.
And that’s the kind of work we are proud to do at SVChange.
