The Messy Middle of Transformation: Hard Lessons That Make The Work Actually Work
Image: David Villasana
I’ve now spent 24 years working across brand, campaigns, and, more recently, transformation: sales and marketing alignment, integrations, new systems, shifting cultures. On stage, transformation sounds like reinvention and momentum. Inside a company, it’s a bit more complicated.
In one past role, for example, I stepped into a significant change programme filled with promises: autonomy, resources, a clear mandate. Early into the gig it became clear the reality was very different, budgets in flux, decision-making was unclear, and a multi-quarter project was being compressed into weeks with a super lean team.
We still delivered on time. But the way it happened, the speed, pressure, and the politics, taught me something more valuable than the launch itself: transformation succeeds or fails on people, pacing, and alignment.
Patterns I now look-out for (and try to design around):
Over-promising without alignment: Leaders sometimes rush to secure senior talent or kick off initiatives before budget or key decision are really in place. The result? The new person enters a role that doesn’t exist in practice and deliverables are marred with confusion.
Power struggles: Transformation shifts influence. New roles appear, old roles dissolve, reporting lines change. People who once had authority feel threatened, and those dynamics play out in subtle (and sometimes very visible) ways.
Compressed timelines: “Warp speed” delivery often comes at the expense of trust and process. Something might get launched, but the environment around it frays.
Cultural fault lines: Where there are already tensions, transformation can widen cracks into giant canyons of pain. Leaders who aren’t aligned add stress rather than stability.
These aren’t hypotheticals. I’ve lived them, more than once over the years. And while they were challenging at the time, they’ve given me a deep understanding of what really happens inside the messy middle of transformation.
As a leader, here’s how I now tackle them:
Scan early: I map where alignment, budget, and decision rights really stand before the work begins.
Anticipate power dynamics: I pay attention to who feels their influence shifting and design comms and roles to reduce threat.
Respect pacing: I push for timelines that balance urgency with adoption- fast enough to keep momentum, steady enough for people to come along on the journey.
Lead with empathy: I remember that every transformation hits someone’s sense of identity and security, and that trust is built or broken in those moments.
Looking back, the toughest periods in my career have also been the ones that taught me the most valuable lessons. Yes, transformation can be energising and full of possibility, but it also comes with pressure, politics, and instability.
Experiencing both sides has given me perspective I couldn’t have gained any other way. And if there’s one thing I’ve learned, it’s this: to lead transformation well, you have to embrace the opportunity while also anticipating the instability, because both are always present.
And the leaders who succeed are the ones who don’t get blindsided by the messy middle, but prepare for it, with clarity, alignment, and empathy at the centre.
Let’s Talk.
If you’re navigating change - a merger, transformation, or a moment where marketing needs to lead, I’d love to help.
👉 Email me directly: andrews_samantha@hotmail.com
👉 Or message me on LinkedIn: Samantha Andrews