The Challenge: When Business and IT Stop Talking

This is the story of one of the earliest and most formative transformations I was involved in. It’s a powerful illustration of how deeply misalignment between business and technology can damage delivery, morale, and customer outcomes.

The organization had a product function and an IT function that were, quite frankly, at war.

They were based in different countries, but on the rare occasions they found themselves in the same place, people would literally cross the street to avoid each other. Online interactions were tense and transactional. Conversations quickly devolved into finger-pointing. Trust was nonexistent.

The impact was predictable:

• Delivery was slow and painful

• Releases were stressful and disruptive

• Neither side felt the other was doing a “good job”

And yet, on paper, everything looked fine.

The Root Cause: Perfectly Designed… to Fail

What made this situation particularly striking was what we discovered during annual review season.

Both the product organization and the IT organization consistently received their maximum bonuses.

How?

Because their objectives were perfectly optimized for silos.

The product function was measured on:

• Specification completeness

• Specification quality

• Hitting handoff deadlines to IT

The IT function was measured on:

• Delivering against timelines they themselves estimated

• Meeting commitments based on those specifications

From a performance management perspective, everyone was winning.

From a customer and delivery perspective, the system was broken.

Specifications were delivered “on time” but lacked clarity. IT padded estimates to protect themselves. What was delivered technically matched the documents, but not the evolving needs of the business or customers.

The organization had unintentionally engineered conflict, mistrust, and delay into its operating model.

The Intervention: Aligning Around the Value Stream

Rather than starting with process, we started with alignment.

We introduced a fundamentally different mindset:

• Shift from siloed goals to shared outcomes

• Align work around the value stream, not the org chart

• Bring product managers and delivery teams into the same planning and conversation space

Concretely, this meant:

• Aligning dedicated delivery teams with specific product managers

• Embedding product managers into technology planning and roadmap discussions

• Creating transparency around long-term objectives, technical direction, and delivery trade-offs

Most importantly, we aligned both groups on the same objectives:

Time to delivery and high quality changes successfully released to customers.

The Turning Point: When Incentives Changed, Behaviour Followed

Once product and technology teams were measured against shared outcomes, something remarkable happened.

They started talking.

As those conversations increased, relationships softened. Adversarial dynamics gave way to working relationships. Product managers gained empathy for delivery constraints. Delivery teams gained context on customer and market needs.

The system began to self-correct.

The Results: From Uncertain Quarterly Releases to Continuous Flow

The quantitative impact was dramatic.

Before:

• Releases every 3–4 months

• 6–8 hours of downtime per release

• Two weeks of live testing by the business due to lack of trust

• Slow feedback and growing customer dissatisfaction

Within 6 months:

• Delivery cycles reduced to two weeks

• Downtime reduced to less than one hour per release

• Business no longer needed to perform post-release testing

• Faster feedback loops and clearer communication

Smaller, more frequent releases didn’t just reduce risk - they rebuilt trust.

The Customer Impact: From Playing Catch-Up to Leading the Market

As delivery cycles shortened, customers began to notice.

Instead of receiving features months late and misaligned with their needs, they saw regular, meaningful improvements. The organization shifted from lagging behind competitors to delivering ahead of them.

User satisfaction and adoption improved - not because of a single “big transformation”, but because the organization learned how to continuously steer the product based on real feedback.

Why This Matters

This case study illustrates a critical truth we see repeatedly:

Most delivery dysfunction is not caused by people, but by systems that unintentionally reward the wrong behaviours.

By focusing on alignment, value streams, and feedback loops, this organization didn’t just improve delivery metrics. It restored trust, pride, and momentum across teams. It reconnected delivery to customer value.

That’s what sustainable transformation looks like.