How to Help Middle Management Transition to Servant Leaders


Perhaps the hardest transition in Agile adoption belongs to the Middle Managers. Essentially, everything they own and have earned striped away on day 1. Unfortunately for them, the power of self organizing teams trumps their role in agile environment.

I am one that believes that middle management can still add value in a agile environment. Their focus shifts from tactical to strategic and role changes from manager to servant leader.

The hardest challenge I have faced is getting them to accept their new role. Lately, I been experimenting with different approaches to help them embrace it. I am wondering what others have done in this area to help Middle Managers make this transition?

Discussing agile with Executives/CxOs
Communicating "The Agile" to Leadership and Middle Managers

I have a hypothesis that this phenomenon, “the challenge of ‘transitioning’ middle managers,” is caused by the failure to change structure before changing process.

In other words, organizations tend to use training and policy to change practices, without altering the existing structure (system) first. The common folly of the western business: reductionist thinking.

The result is a structure that calls for a set of legacy behaviors on top of these new “agile-like” practices (teams, sprints, and whatever else can be trained). If “getting them [managers]” to accept their new role is hard, stop! That’s a sign you’re influencing the wrong part of the system.

John Seddon observed that behavior is the product of the system. There are countless other examples of structure driving behavior - Larman, Deming, Ackoff, Senge…

…so perhaps “helping Middle Managers make this transition” is less important than creating the structure where a new management role is possible in the first place.


@zachbonaker , can you elaborate what that ideal structure would look like? Thanks


If there was a one-size-fits-all structure, with predictable cause-effect relationships, that worked for all people, we’d be using it.

I’m suggesting the use of systems thinking to inform the coach/agent in creating a new system of work. One that makes “role changes from manager to servant leader” both desirable and rewarding.

What is the “ideal structure?” It might look like anything. If you’re finding managers are pushing back, use your systems tools - is it a case of compensating feedback? Or are espoused principles in conflict with the principles in action (e.g., spouting about self-organizing teams while individual performance reviews are taking place).

Ask yourself: what holds this pattern in place? There’s your leverage. Change the system, change the behavior.


I hope more information comes from this article. I’m meeting soon about the roles of existing managers of scrum teams.

  • One of my thoughts is that the managers can be leaders of the overall product vision and help craft that while the PO’s develop the stories to make that vision a reality along side the team.


@Gemphilly I would ensure that your POs always maintain some ownership of the product and are not just steered by the Leaders. I have come across problems with this in the past where POs end up having little or no control over the product direction, which then results in the teams having very little input and a leader just dictating what has to be done.

In my experience the Leader and PO need to have (or build up) a healthy working relationship and be co / near located.


I will echo the comments from @paul.cutting. In fact, the company I’m currently working with suffers from exactly this “flaccid product owner” problem.

@Gemphilly, I caution you to think deeply about that structure you propose. What implicit message does it send the team? Consider the “reporting structure” also - would team members report to this manager?


@zachbonaker Yes the PO’s report to one AVP and the dev team reports to another AVP.
@paul.cutting Currently the POs are learning how to be POs and are expanding their ownership. I have to teach them to be POs. They have to become true POs at some point or the bottleneck will get huge.


@zachbonaker I find your hypothesis interesting. It is basically applying Conway’s law for computer system design to organizational theory. You have rented real estate in my mind for the next hour or two as I unpack this :face_with_head_bandage:


@ryan what was the outcome of your “unpacking?”


I think you are on to something @zachbonaker. But I genuinely believe an equal detractor to transforming middle managers has to be attributed to the larger org not creating a shared vision of where the transformation is heading. Not doing this causes confusion, frustration, and a loss of safety. The human condition, given this type of environment, is to resist and fall into comfort patterns.


Current org I am at is going through a full reboot on their agile transformation. The middle management and senior leaders keep coming back to reinvent the old world with basically a slight mod on the existing process and not focused on evolutionary change. The majority of them sit in the late adopters and laggard side of the Change adoption cure.

The global organization has is providing air support for the change. As the coaches wait on the empowerment.

What I have found to work lately is to find their kryptonite person that they regularly listen too when they need advice and influence them as a method to promote change.

When that fails I have been using Lawyer logic like waste analysis on their concepts to show we’re this puts us. Often resulting in an experiment.

So far so good and we have started seeing more folks slowly going hum we can make this better!

I still have not found a way to get past the people that are a leader/manager that are completely incompetent and have unwittingly risen to power somehow.


I believe you can help managers become better agile leaders through education, feedback, and reflection, but I’m not so sure you can turn them all into true servant leaders.

When organizations transition to agile, many first line level managers/supervisors get nervous because they are told to let the team self-organize and stop micro-managing. Some will discover they now have the time to manage up and out, rather than down, and focus on solving organizational challenges. Others will fully embrace servant leadership once they understand what it is and the value it can bring to the organization. Others will opt out and go find some people to control someplace else.

I think the focus is helping leaders understand the value of leadership agility. Leadership agility is the foundation of organizational agility which is the foundation for business performance. This message is usually well received with senior leaders.

My tools for this historically have been executive overviews and coaching. I’m now using the Leadership Agility 360 Feedback process and just starting to provide Certified Agile Leadership workshops.

10+ years ago our focus was on on helping the team. The next bottleneck was the business, so we increase out efforts on helping them understand Product Ownership. Then it was scaling and we now have lots of scaling patterns to choose from. Our next challenge is leadership.


Me too. As an external phone coach, I am able to help without politics, without bringing in assumptions f4om the system.

I believe all people are brilliant. Some middle managers need help remembering their brilliance. For these, I am hoping that my Bigger Game Journal may provide a way for an agile coach (without the time or perhaps skill or mandate) to help a self-aware leader remember and re-calibrate.

For some people, however, their brilliance would be better contributed in a different way, or even in a different place. Again, as an external coach I can help this surface, with less politics, and improve both their lives and the lives of the teams they leave: win-win.

I’ve added 3 different ways for leaders to play Fearless Journey as a solitaire. It is a way to explore new ways of influencing and helping an organization. This is new, I’d like to hear stories f4om people who use it: is it helpful?

It can be awkward being a coach or change agent to managers who fear you are there to eradicate them. My hope is that listening, appreciating them, engaging their strengths, encouraging them and giving them space to re-design themselves … this stance offers them respect and support. Powerful questions can be a key tool here.

But I believe you cannot hold space for this intuitive work while running at 110% because you are helping several teams. Michael Spayd used to recommend thst team-level coaching and org-level coaching be done by different people, mainly to free them from real or perceived conflict-of-interest, iirc. (I’m out of touch with his current work. He may still say this). But I maintain that this separation is also important to avoid burnout and allow space for intuition, which tends to get lost when we have too many balls in the air, i.m.e. Humans are not good at holding multiple viewpoints at once, we tend to favour one and neglect others. (For ex. I believe this is one good reason to separate PO, SM and dev roles… the conversations are much more generative when tbey are not all happening in one person’s head :slight_smile:

Note: while middle managers explore and re-incarnate they may also benefit from our championing and shelter. We must be compassionate and believe that their brilliance will show up, even while they seem dull or even ornery :slight_smile:


This really hits the nail on the head for me. They will either turn inwards towards the team, outwards towards the org, or quickly find that they don’t have a place here anymore.


Yep, I agree. I think also you’ll sometimes come across a middle manager who’s truly trying to embrace servant leadership and who’s started drifting into more of a professional/leadership development coaching role with their direct reports but who’s getting pressure from “above” to revert back to command-and-control tactics. When the partners/founders/board/C-Suite are pushing certain expectations, decisions, and performance metrics on middle management that strongly discourage letting direct reports experiment, fail, and learn, it puts the middle manager in this awkward squeezed out space between wanting to empower their teams and holding them to strict boundaries mandated from above.

@dpreuss - I’m starting to reach the same conclusion - organizations need various levels of coaching, from the middle layers up to the top, to tackle this middle management challenge. I also believe they should review their performance management practices, since so often those practices (and the mindset behind them) seem to be a key factor creating this tension - but that’s a topic for another post. :slight_smile: I can’t help reflecting on Laloux’s “Reinventing Organizations” when I see organizations struggling with this - because I think what we’re really talking about is recognizing the need for helping an organization evolve into a higher level of being. Which sounds really new agey, but I’m not sure how else to describe it. I think leaders sometimes don’t know what they don’t know, which is where coaches can help most.


What do you all think of these articles?

I like the roles 6 core activities of the Agile manager, from the article:

  1. (Still) Manage the portfolio of projects and coordinate with other managers
    Define projects strategy at the organization level
    Set priorities
    Define budget and resources
    Do the staffing
    Work with peers as a team

  2. (Still) Manage recruitment
    Hire people
    But also fire and solve potential conflicts

  3. Support Projects and Agile self-organized Teams
    -Promote autonomy and self-organization
    -Remove impediments that the team or ScrumMaster are not able to manage
    -Manage logistics
    -Buy the supplies
    -Challenge teams and help them to improve their knowledge about products, tools, technologies, methods…

  4. Create a relationship of trust, develop (career) and motivate people
    -Make yourself available
    -Get to know each person and his work
    -Facilitate the acquisition of new skills
    -Give feedback
    -Give work recognition
    -Delegate tasks

  5. (Still) Create an environment for success and energize change
    -Communicate the vision
    -Give a direction
    -Adopt the appropriate management style
    -Simplify usage
    -Seek performance through appropriate tools and processes based on continuous improvement and waste elimination

  6. Initiate, support and animate communities of practices
    -Give time and resources to agile communities, ScrumMaster, Product Owner, Agile Manager, Architects, UX Groups …,
    -Promote communities of practices in the organization

from an article (
focus on ensuring that his team members:

  • had the right skills,
  • understood the agile principles, and
  • were given the education they needed to become a fully cross-functional team.

And then there is this article from 2008 by Lyssa Adkins and Michael Spayd “The Manager’s Role in Agile”

There are also some good points in this article.