When I think back to some of the toughest agile transformations I’ve worked on, one common challenge always rises to the surface: how to get senior management on board in a meaningful way. And no, I don’t mean the vague “Yeah, we support agile” lip service. I mean real traction. The kind that shows up in funding decisions, priority calls, and how leaders spend their time.
In one transformation I supportedat a large UK defence company, we had all the mechanics of agile in place. Product teams were using Sprints, Daily Scrums were happening, and there was even engagement in the Sprint Retrospectives. But the outcomes we identified weren’t - to quote Gunther Verheyen - "moving downfield". Teams were demoralised. Dependencies were stuck in governance queues and halfway down a Product Craplog. It may not surprise anyone who has been in a similar situation that all of our directorship thought the problem was with the teams not “doing agile properly.”
Sound familiar?
Agile in the Basement, Waterfall in the Boardroom
The big issue we faced was this: we were trying to install agile at the delivery level, while the operating system of the business remained rigidly traditional. This meant delivery teams were being asked to work in short feedback loops, yet leadership still expected quarterly delivery plans, phase-gated reviews, whilst also remaining 'responsive to market changes'. There's a phrase for this, and it's something about having a cake and eating it too...
But this is where I'd failed. I hadn’t changed the conversations at the top and therefore their sponsorship was minimal because their understanding was limited (or non-existent).
It became clear that until senior leaders were equipped to think and act differently, our change would stall. So I changed my strategy.
Shift the Conversation from Process to Outcomes
The first thing we did was stop talking about agile. Instead, we asked leadership what outcomes mattered most to them. We heard things like:
“Faster time to market.” “Better customer experience.” “More resilient teams.” You know, all the usual stuff.
Once those goals were explicit, we could draw a straight line between them and the agile principles that would support them. This shift created new space for dialogue. Leaders who’d dismissed agile as a “technical team thing” started to see it as a business enabler. The shift was to stop talking about agile and start talking about operating model outcomes.
The second shift came when we realised leaders weren’t resisting because they didn’t care. They were resisting because they didn’t feel involved. So we stopped trying to sell to them and started co-creating with them.
We ran short, facilitated sessions where leaders explored questions like:
What would it mean for you to lead with more agility?
How might our current governance structures be slowing us down?
Where are we incentivising predictability over learning?
Those sessions were uncomfortable but necessary because they built ownership.
Build Feedback Loops at the Executive Level Too
One thing I see a lot in transformations is the expectation that delivery teams will inspect and adapt, but executives are exempt from this loop.
Why?
In the case study I've discussed here I helped our executives to adopt lightweight review cadences where they could inspect product progress, hear from teams, and reflect on their own impact. We even had a Director say “I'm sorry, I know I am the impediment here. Let me fixit.” That kind of behaviour change doesn’t happen through training slides. It happens through visibility and shared reflection.
If your agile transformation is struggling to land at the top, ask yourself:
Are you inviting your leaders into the transformation, or just informing them of it?
Enterprise change is hard. But it becomes much easier when senior leaders become active participants and not just sponsors. When they model the mindset shift themselves, it sends a far stronger message than any framework ever could.
And if you're a Scrum Master or Agile Coach: don’t just coach the teams. Coach the system. That’s where the real change thrives.