What Must a Manager Do for a Successful Agile Transformation?

Your organization is “going agile.” They’ve selected their framework, sent people to be trained, brought in coaches, and told leaders they need to become more “servant-like” — hey, it’s a mindset, folks! Metrics of success have been hinted at but remain unclear. In this situation, what must management do for a successful agile transformation?

The top of the organization has done its part — they’ve set the north star (albeit an ambiguous one) and laid out a high-level roadmap to guide the transformation. The bottom of the organization has also stepped up — smilingly joined teams, embraced practices like scrum, and eagerly started playing their roles.

Now comes the middle of the organization — and here lies the challenge. The middle is often struck with fear, anxiety, ambiguity, and risks tied to power, authority, accountability, and even job security. For middle management, the shift to agile can feel like stepping into unknown territory, a place where the metrics of success are constantly shifting and the familiar structures no longer apply.

The traditional role of a heroic leader, who does whatever it takes to achieve the goal, is suddenly less relevant. Leadership is no longer confined to a position or title — it’s now expected to exist at every level of the organization.

So where does that leave middle management? They find themselves beginning to morph into something unfamiliar yet surprisingly familiar, adapting to a new dynamic where coaching, enabling, and facilitating take precedence over command and control.

As the organization leans into frameworks like scrum and refines its roadmap to transformation, middle management must navigate these changes with a focus on balancing agility, measuring progress through meaningful metrics, and fostering a culture of empowerment.

Success in agile transformation isn’t just about adopting new practices; it’s about redefining roles and mindsets at every level. For the middle of the organization, this is both the greatest challenge and the greatest opportunity.

Management’s Difficulty in Agile Transformation

What is a middle manager to do in the middle of an agile transformation? You find yourself literally stuck in the middle, juggling the conflicting demands of agile teams focused on continuous improvement and senior leaders expecting results aligned with strategic initiatives and a long-term roadmap.

You make a decision one day, only to be told you need to empower your teams and let them take ownership. You delegate authority and allow your teams to self-organize, only to find yourself called into the boss’s office as they vent their frustrations about a failure that just occurred. It can feel like a no-win situation, straddling the line between fostering team autonomy and meeting leadership’s expectations for success.

If your organization has opted for a scaling framework, it may seem like a solution has been put in place. Often this involves shifting higher-level individuals into “agile” roles at the program or portfolio level while maintaining a hierarchical structure that feels familiar.

While this can provide a temporary sense of clarity by stabilizing roles and responsibilities, it’s often just a short-lived gain. Beneath the surface, the structure may still be concealing long-term opportunities for growth, experimentation, and continuous improvement.

However, this temporary pause in the chaos can work to your advantage. Use it as an opportunity to assess your role and how it fits into the bigger picture. If your organization is less precise in defining your new role during the transformation, the invitation to pause and reflect still exists. Take this time to align your efforts with the broader roadmap and identify initiatives where you can support both agility and organizational goals.

By focusing on fostering continuous improvement within your teams while balancing strategic alignment, you can navigate this challenging middle ground more effectively and help drive the transformation forward.

A Strategic Pause

Taking a pause is more than just a break; it’s a powerful and generative opportunity to reflect, reset, and realign your goals. For agile coaches, it provides the space to explore key questions about your direction, priorities, and aspirations within the context of agile methodologies, enabling you to gain clarity and insight.

During this time, you can engage in meaningful practices that support not only your transition into a new role but also your continued growth, self-awareness, and agency as an agile practitioner. By intentionally stepping back, you create room for creativity, fresh perspectives, and strategies aligned with agile principles, empowering you to move forward with purpose and confidence.

Create a Learning Group With Your Peers

Starting with building the foundation, find or create a learning group with your peers. Others around you are likely struggling with this same uncertainty.

You have the choice to engage in water-cooler gossip or take control by forming a learning group that is energized by the urgency and excited for the opportunity to leverage group intelligence to co-create possibility.

In this group, you can discuss new information, look at it from different perspectives, evaluate it for your own purposes, and practice some of the teaming skills that your organization’s teams are likely struggling with as well.

Share Your Journey In Implementing Agile Foundations

Share your journey with your organization and ask for their help. This doesn’t mean offloading all your stress onto others or seeking sympathy. As the saying goes, good leaders throw up, not down — meaning they process challenges in a way that uplifts their team rather than burdening them.

By opening up and sharing your experience, you create an opportunity to practice confident humility, showing strength in being vulnerable while remaining solution-oriented. This approach allows you to acknowledge the shared challenges and experiences within the organization, fostering a sense of connection and mutual understanding. It also encourages collaboration, inviting others to actively participate in co-creating meaningful change that reaches beyond the team, positively impacting the larger organization.

Listen attentively

Middles have often been well-trained to listen to respond or listen to critique — focusing on formulating their next point before the person speaking has even finished. This habit can lead to miscommunication and missed opportunities for deeper understanding.

Instead, listen for understanding — pay attention not only to what is being said but also to what is not being said. What emotions, concerns, or ideas might be lingering beneath the surface?

Listen actively and take the time to check in on your understanding with those around you. Ask clarifying questions, paraphrase what you’ve heard, and engage in discussions that co-discover possibilities, rather than simply debating or reacting.

A simple practice you can adopt immediately is to notice when you are listening to respond. Catch yourself in the moment, take a breath, let go of your rehearsed response, and refocus on the present conversation. It may feel challenging at first, but with mindfulness and practice, this shift will become more natural. Over time, you’ll find that truly listening transforms not only conversations but also your relationships and collaborative potential.

Make Strategic Agile Decisions

Make decisions ONLY when necessary. Too often, in service of team empowerment, leaders unskillfully announce it and just assume those in their organization are willing to just jump in and assume the risk associated with newly-delegated decision making.

A great model to check out is David Marquet’s Intent-Based Leadership, which leverages the pillars of competence and clarity as team members engage in the decision-making process.

To those around the middle managers, their leaders, and reports — this is not an invitation to weaponize this against management (they should be doing…).

Turn the pointer from someone else to ourselves. We honor the achievements of the industrial era and the contributions of managers and have now arrived at this place and time, standing on the threshold of what is next.

A well-respected coach once said, “Once you let Jack out of the box, you won’t be able to put him back in.” People long for the shift from machine to human in the workplace. So what MUST managers DO in an agile transformation? Make THE decision; are you IN?