Practical Steps for Leaders: How to Execute an Agile Transformation (and Foster Innovation)

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Peter Reynolds

Client Partner

Peter Reynolds

This is the first in our series on Agile for Executives. You can find the second post in this series here and the third post in the series here.

Being agile isn’t just the tools you use, the release cycle you follow, or calling things the right names. Agility describes a shift in prioritization, a new valuation of work, and a move toward more experimentation. It isn’t an excuse for chaos, but it is a loosening of your grip. It requires a holistic mindset and commitment from all levels of leadership to truly reap its benefits.

Agile organizations offer flexibility, faster time-to-market, and customer-centered outcomes via a culture of transparency, continuous improvement, and empowerment. With benefits far exceeding the cultural costs, an agile transformation takes time, understanding, and flexibility while offering targeted products, open communication, and clear structures.

This series discusses how to begin your agile transformation, how it impacts your company culture, some outlined steps on how to get started, and what it means to you, the executive, as you begin. To start, let’s align on some key terms.

What is an Agile Transformation?

An “agile transformation” describes the process of adopting an agile methodology across an entire organization. It involves a fundamental shift in the way that you plan, execute, and deliver work.

Ultimately, agile transformations aim to create a more flexible and responsive organization better able to meet the rapidly changing needs of customers and markets. Agility requires more than just using an agile framework, more than having a Jira instance, and more than calling windows of time “sprints.”

Outcomes, Not Output

Agile organizations focus their efforts on achieving outcomes more than hitting certain levels of output. Prior to embracing agile, most organizations focus on output as a metric to measure success. Emphasizing ticket quantity, throughput, and strict roadmap adherence, output centered shops tend to become “feature factories.” This often looks like a roadmap clogged with a laundry list of unrelated enhancements. While working down a long checklist of to-do’s can feel like significant progress, it does little to tell you if you are actually being successful in your market.

Conversely, agile shops focus on outcomes, which center around problems solved, customer engagement, and new possibilities. Estimated return on investment, user story, and strategic value drive priority on an outcome-centered team. Under an outcomes paradigm, executives pay attention to metrics and use cases instead of number of new features. By shifting the focus from engineering work output to customer outcomes, you can monitor a user’s ability to do the things they signed in to do instead of the specifics of which graph or number of buttons they can click.

Evaluate, Evaluate, Evaluate

Agile transformations mean a departure from traditional waterfall delivery. Instead, in an agile organization, product leadership consistently evaluates priorities and places the team’s focus under regular evaluation.

As the market and users adapt, an agile product team frequently and regularly reprioritizes the roadmap to keep pace. The team focuses on customer outcomes, reacting to feedback, and experimentation with new solutions. An agile organization holds the roadmap open-handedly. This, however, does not mean working in chaos.

Leadership and stakeholders review the product and the desired outcomes over a series of iterations. With every iteration (scrum calls them sprints), the team and their stakeholders evaluate the results of the past iteration and determine the next priority. These iterations do not look like big, six-month releases of waterfall; instead, smaller features and shorter user stories provide opportunities to change direction along the way.

Trust Your PO

Reevaluating priority this regularly becomes a burdensome task, especially when you have a variety of stakeholders. Everyone has a strong opinion on what should come next. Most agile frameworks respond to this dilemma with a role akin to the Product Owner (PO).

The efficacy of this PO role relies entirely on trust and empowerment. Stakeholders must trust that the PO hears all their requests, balances them with the requests from others, and ultimately refines them all down to a single priority order.

As an executive, empowering your PO to make priority calls and trusting them to focus on outcomes means you need to take a step back from the process. Try to view the application at an abstract level rather than being in the weeds of tickets and features. Provide feedback, vision, and direction, but don’t get caught up in specific layouts or priorities.

Trusting the PO to hear your feedback and allowing that to shuffle into other stakeholder’s priorities marks the first way you as an executive can lead your organization towards an agile culture.

What is Agile Culture?

To better understand agile culture, you need to understand the current state of your organization.

Traditional waterfall organizations communicate in a way where mandates flow down the hierarchy and reports flow up. Practically, this looks like deadlines and strict requirements coming from executives and requiring their final sign-off on all new features. But this “command and control” style of leadership often leads to a top-heavy and slow-to-change product.

Conversely, agile advocates a culture in which information and context flow down the ladder, and only blocks and questions bubble upwards. Decisions, implementation timelines, and functional requirements solidify within the team rather than at the top.

In this model, executives must lead with a lighter touch. They champion users and vision rather than specific features. Leaders enable their team to make decisions that solve the need, trusting them to make something useful in the timeliest way possible.

What’s Your Role?

Agile executive leaders shape the company atmosphere into one that values collaboration, learning, and experimentation in even the smallest interactions.

From the water cooler to the strategy meeting, discussions on user outcomes and engagement elevates the culture above busywork. Your role requires more than keeping everyone busy. Fostering an environment of innovation and growth requires true servant leadership.

As both boss and check-signer, you get a certain amount of leeway in interactions with your organization. This, unfortunately, also makes it more difficult to receive unbiased feedback. Company culture settles at the lowest tolerated behavior, and your insulation makes you more vulnerable than others to exhibiting this lowest tolerated behavior. Consequently, you set the standard culture.

Flexibility with delivery, blamelessly addressing problems, adapting on the fly, and encouraging collaboration require abandoning unilateral decisions and micromanagement. Embracing the role of a leading servant means fostering an ethos of empathy, listening, creativity, and service.

Dynamic collaboration, design discussions, and constant learning drive agile culture. Focusing less on everyone having something to work on and instead on attaining outcomes has benefits across your entire organization. It gives engineers, for example, space to reinforce application architecture, try out new technologies, and improve user experience. It also allows designers and content creators space to thrive in what they do best by letting the engineers build the best solution to their use cases. Leaving room for experimentation does not mean prioritization chaos, but instead means keeping priority an open conversation.

Cycling through trial, inspection, and adaptation, an agile organization consistently reviews experiments and adjusts the roadmap accordingly.

Shifting Focus

Your organization’s agile goals will completely change the way interactions and delegation look in every corner of your company. Centering conversations on the user and their outcomes elevates your goals above throughput and instead directs them toward customer success. Getting the right person as Product Owner to consolidate and track those outcomes presents challenges, but trusting them to do their work well enables you to cast a vision for the company as a whole.

Looking ahead, we will continue by taking some practical steps that you, as an executive, can take toward becoming a more agile organization.

When you’re ready to put the power of agile to work for your entire team, get in touch with DockYard and let us help you find success, faster.


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