About three years ago, as my time at Resigility was coming to an end, my partner, Matt, and I started asking ourselves a simple question:
If we were going to build something new, what would we build it on?
Between us, we had more than 25 years of experience working with CIOs and executive teams.
We had seen strong leaders succeed.
We had seen capable organizations stall.
And we had seen how often the difference wasn’t talent or effort — it was the system around them.
Some organizations had strong enterprise platforms.
Others were still fragmented and evolving.
In both cases, we saw the same pattern.
Priorities drifted.
Accountability blurred.
Execution stalled.
Software can move information and automate processes.
It can’t, by itself, align strategy, funding, incentives, and delivery.
Too much important work lived in the gaps.
Strategy in one place.
Governance in another.
Delivery somewhere else.
Performance management off to the side.
We started WYS on the belief that those “in between” spaces are where most execution problems actually live — and where many firms, by design, don’t spend much time.
Many firms specialize in parts of the system.
Fewer stay with leaders in the spaces between them.
We also built WYS intentionally as a small firm.
Not to be small for its own sake — but so we could stay close to the work, integrate across disciplines, and bring serious systems thinking without layers of bureaucracy.
Over time, what has mattered most to us isn’t volume or visibility.
It’s whether clients keep trusting us with their hardest problems.
Many of them have — for years, and sometimes over a decade — even as their roles and organizations changed.
That tells us we’re helping solve real problems.
Going forward, my partners and I are going to share more of what we’re learning from that work — about strategy, execution, governance, and performance — and why so many organizations struggle with the connective tissue between them.
Not as “thought leadership.”
Just as practical reflections from the field.
If it’s useful, great.
If not, feel free to scroll on.
