Leading an Agile Transformation in Your Enterprise – An Interview with Jon Terry

Leading an Agile Transformation in Your Enterprise – An Interview with Jon Terry

Most organizations are on the path to scaling Agile within software development or IT. Although organizations are beginning to see the advantages of an Agile transformation beyond IT, a successful transformation involves more executive participation in an active way. No longer do you need to convince executives they should support scaling Agile delivery, but instead, for it to be a successful transformation, you need to convince leadership to be actively engaged.

I sat down with Jon Terry, Chief Evangelist, Lean-Agile Strategy at Planview, to discuss successful patterns of how executives lead their organization through an Agile transformation, considering who needs to be engaged, challenges to expect, and mistakes to avoid. Let’s jump right in.

What’s in it for executives to become engaged in an Agile transformation?

At the highest level, success or failure of the transformation. Like any other significant organizational change movement—executives must be involved to support the organizational structure change, along with the culture change. If you really want an Agile transformation to be successful, executives must help drive the change through those obstacles that are inevitably going to happen. Executives who successfully engage in an Agile transformation see tangible results: faster time to market, better market share, and funding the right products at the right time. A successful Agile transformation can also improve morale across the organization, creating more engaged employees, which ultimately means better retention numbers.

What type of leadership is needed for a successful Agile transformation?

An executive’s biggest role in an Agile transformation is to encourage groups of people to work together and, in essence, force the conversation and change to happen. The goal isn’t to force the outcome of the conversation but instead provide guidance through servant leadership. Executives and leaders cannot just accept the situation when everyone is just smiling and saying, “Great, we’re going to do it.” It’s up to the executives to push until a difference of opinions arises, and then leaders sponsor the facilitation of conversations that actually get to the uncomfortable points of this kind of a change. Leaders should not accept the proposed path forward until those differences in opinions are discussed.

In my opinion, I think some of this is modeling the behavior. If an executive is asking people further down the chain to delegate more of their authority, while communicating the corporate mission, then they have to be okay with the solution being different from what you might think is the right idea but supporting the decision to try. Executives need to model that behavior for people further down the chain.

Additionally, executives must recognize an Agile transformation is a major change, and people are going to make mistakes. Modeling the behavior of allowing people to fail and not falling back to command and control when those mistakes inevitably arise, is also a behavior to model. Ultimately, you’re trying to encourage your subordinate leaders to do the same thing.

Seven Benefits to Scaling Agile

What is a common obstacle an executive or their management team might need to overcome for a successful Agile transformation?

I think that in most organizations, when we talk about creating a strategy and then developing programs and projects to execute on that strategy, the usual way that’s pushed downward is via a “this is how you’re going to do it” approach, as opposed to, “this is what I want to accomplish, you (teams) figure out how to get the result.” I think that happens at any level, because usually the people who get to executive positions get there because they’re good at their job and have a strong understanding of the level below, and that’s a natural tendency to follow.

Using myself as an example, I’m a product guy. I love products and can get deep in the weeds in products, and that’s very tempting, and I enjoy doing that. But if I spend too much time in the weeds and make decisions for people, people will just way, “Well Jon’s the boss, if that’s what he wants to do then okay.” By doing this, we missed out on other ideas from those closer to the work. Instead, leaders should lead through intent and provide guidance. When you receive an idea or a path forward that’s not quite the way you would have done it, ask yourself, “well, do I genuinely believe that’s disastrously bad, and we’ll really fail in a bad way if we do it that way? Or, is it just not the way I would have done it, and let’s take a shot at it.” If you go down the path of not supporting an idea, be fully transparent as to why so that the team can grow and understand beyond just getting shut down by the boss.

What is the biggest struggle organizations are having when trying to scale Agile? In lots of conversations we’re having, agility at the team level is reaching a tipping point. And that’s a good thing, because customers are saying, “Agile delivery is generating results. We like that; we want to do more of that.” However, more often agility at the team level has reached a point where, for all the good it’s doing, it’s breaking how organizations traditionally run their business. It’s up to the leadership to determine how to support Agile delivery so that they can continue to compete in the market and retain customers.

Probably the number one benefit of scaling agile is coordination across the enterprise.

Agile brings a new way to deliver work at the team level, but it breaks the way executives used to run their business, which was via business cases and projects. While there are people who would say, “just get rid of those processes,” that’s not most organizations. Maybe that makes sense if you have efforts that require one and only one team, and you have a technical architecture with no dependencies across teams, without any legacies to maintain. However, for most organizations, the things they build and sell require multiple teams to actually deliver real value. Organizations’ traditional ways of coordinating won’t work with Agile delivery, and these organizations need a new way of coordinating across and down the enterprise. This the starting point for companies scaling Agile. They likely have Agile teams, but they’re not working together across teams, nor do they have the empowerment to make decisions. This is where scaling methodologies come in.

What to learn more? Download the whitepaper, “The 7 Benefits of Scaling Agile”.

Emily Peterson

Emily Peterson is a Product Marketing Manager for Planview's Lean & Agile Delivery Solution, focusing on helping organizations achieve agility on their terms and timeline. She uses her professional experience in agile marketing to leverage new ways of working across the organization, connecting all parts of the business to the overall goals of the organization