3 ways your agile transformation is failing

A self-sabotaging pattern in agile transformations can damage business relationships and set your product people up for failure. Here's what you can do right now to course correct
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My boss (the CEO) walked into my IT leadership team meeting, looked each leader in the eye and said, “You’re the bottleneck. You’re the reason we can’t get more work done around here.”


The elephant in the room stomped its foot and we all took notice. He was right. We all knew it, and at the same time, this was the call we wanted (needed) to hear.

To his credit, our CEO followed his words with action. We received funding, started hiring, and started our transformation. After “exploring agile” for months, this was our moment.

So we did what everybody does: We found a great consulting firm, set up two-week sprints, refined our backlog, and retro’d like nobody’s business. It was incredibly fun to watch the team come to life and take new ground. I am still very proud of the team we built.

Read also: Agile vs. DevOps: What’s the difference? ]

But we made three mistakes that impacted the team for the next couple of years. In particular, we failed the product management folks and held back progress in the foundation we built from day one.

My hope is other IT leaders will avoid these mistakes when embarking on an agile transformation . Here are three things we did wrong in our successful transformation and what you can do right now to course-correct.

Mistake 1: We trained them in process, but not in product

We sent our product management to a two-day course, they got their certifications, then started their work with a team. Like most agile transformations, we thought this is what it meant to be a product owner. They learned things like prioritizing a backlog, refining user stories, and how to run a sprint review.

But this is only half of the role. You may have heard the phrase “CEO of the product.” Product managers in particular function with a CEO mindset over the product. In other words, they see all aspects of the product and ensure the product gets everything it needs to succeed. How would you feel if your CEO spent all their time in activities like prioritizing backlogs, refining stories, and running sprint reviews? I fear your business wouldn’t last long.

To fix this, try these things:

  • Hire a coach that focuses on product management. Often called discovery coaches. They understand product and agile and can help your product folks become CEOs of product.
  • Send your product folks to a product management training course.
  • Buy and share key books on the topic: Start with the classic, “Inspired” by Marty Cagan.

Mistake 2: We allowed the business to give us part-time practitioners instead of full-time strategists

With our misunderstanding of product management, we easily fell into the trap of getting practitioners from the business instead of the more strategic business leaders. The people were wonderful to work with, and the work was made clear, but few of them saw themselves as CEO of the product, and none of them were dedicated to the work. The resulting problems were subtle and catastrophic all at once.

The resulting problems were subtle and catastrophic all at once.

In reality, it looked good at first. One might argue that it still looked good years later, but there was something considerable missing. Product folks, who remain on the front lines, lack the time to see the product’s big picture. Unfortunately, some also lack the mindset.

You know this is happening if your team only focuses on the short term, immediate needs of the business. Instead of plotting a course to world domination, you see them fighting to keep their head above water.

Importantly, some of these folks can unleash pent-up leadership potential, put on their strategic hat, and start casting vision for their product. With better training in our transformation, I believe we may have unleashed more.

To course correct, try these things:

  • Read the book described above (“Inspired” by Marty Cagan).
  • After you’ve read the book, cast a renewed vision of product management to your business partners.
  • Swap out people who will not be able to make the change. This is difficult, but every time I do this, people eventually thank me.
  • Invest heavily in the people who remain in their roles. They need coaching about the team and the technology. Building better business relationships starts here.

Mistake 3: We leveraged agile as a capacity-builder, not a partnership-builder

Looking back at our first sprint reviews, we missed the early opportunity to change the narrative about IT. Unfortunately, I led us here. The existing narrative of IT as a cost-center and enabler should have become IT as strategic partner. We did not make the leap, because we still saw ourselves as an enabling cost-center.

It’s akin to when someone is freed after 30 years in prison. They don’t quite know how to engage in the free world, and in some sense, the prison was a safer place. Returning to the prison seems better than their newfound freedom. We didn’t know how to leave.

Ironically, resolving this requires that we become better product managers ourselves. After all, our services are products. One key product management skill is to see the world through your customer’s eyes. Understand their problems and recognize that they spend all their time obsessing over their problems. Being a partner means you reduce your obsession on your own problems and increase your obsession with their problems.

Here’s how to do that:

  • Ask your teams to stop talking to product management about vanity metrics like velocity. These metrics help steer the team, not the product.
  • Each week, send one developer per team into customer interviews with product management.
  • Go through Donald Miller’s StoryBrand. This is one of the best ways to understand the world through their eyes.

In the end, I’m incredibly proud of the team we built and the things we accomplished. However, we missed significant opportunities to change the game. If you avoid these mistakes, you'll create even better product management and business relationships.

[ Culture change is the hardest part of digital transformation. Get the digital transformation eBook:  Teaching an elephant to dance. ]

Rich Theil
Rich helps IT Leaders fix Agile teams burdened by inadequate Product Management and broken business partner relationships. Prior to starting The Noble Foundry, Rich spent 12 years as CIO for a large, scrappy, and aggressive non-profit in Cincinnati. Additionally, Rich spent seven years at P&G in Information Technology.