How to Support Middle Management Through an Agile Transformation

Middle Management gets the Squeeze in an Agile Transformation – Give Them Room to Transform!  

The Frozen Center isn’t frozen – it’s SQUEEZED into paralysis.   

Dave West, CEO at, authored an article with mitigations for the belief that “middle managers will continue to be a roadblock to real agile change.” Dave West discusses techniques to specifically address blocking behaviors and usher in different outcomes. As an Agile Coach, I certainly nodded my head throughout the article. The article started the conversation, and it made me want to dig a little deeper. 

Step 1: Remember a middle manager in my Agile career, then put on my empathy shoes…  

  • Our VP was Molly. She was not central to the transformation.  
  • Our Director was Victor. He agreed vocally to Agile principles, but then did the opposite.   
  • Our Senior Lead was Jason. He vocally opposed the transformation.  
  • Our Team Lead was Denise. She loved the Agile transformation.  

Let’s discuss Victor and Jason – they were smack dab in the middle of the hierarchy.  

Step 2: I’m wearing my empathy shoes. Remember the story from their point of view…  

From Victor’s point of view: Thinking down the hierarchy, his team leads and team members loved the Agile transformation. His direct reports, for whom he completed performance reviews, loved to chat in one-on-ones about their team Agility. The new ways of working allowed his teams to feel more empowered.   

His Senior Lead, Jason, had frequent one-on-ones too, but Jason complained that he didn’t like the transformation. (We will visit Jason’s point of view shortly).  

Moving up the hierarchy, Victor seldom heard anything about the transformation from his supervisor, the VP. Victor had one-on-ones with Molly, the VP, and he shared his thoughts about the misalignment between the Senior Lead and the teams. However, Molly offered lip service that everyone must learn the new ways of working, and change is hard. Furthermore, Molly still wanted her status reports and her methods of reporting to her Executive Leaders in the same way she had always done them. From Victor’s perspective, Molly hadn’t changed her ways of working at all and expected that the transformation was a “team thing.”  

From Jason’s point of view: Thinking down the hierarchy, Jason no longer felt connected to how teams do the work, and yet he felt very much “on the hook” for their delivery. The teams planned their work, but he was the one who reported status up the chain and felt that his neck was on the line when things were lagging. The scrum master, team lead, and product owner felt like extra layers, and he had to jump more hoops to understand how the teams were doing the work. The team members weren’t “direct reports,” and he wasn’t responsible for their performance reviews. Everyone told him the organization was getting “flatter.” He was a senior leader to mentor and collaborate with his teams, but Jason felt a lot of pressure to have teams deliver without any methods for managing them.  

Up the hierarchy, Jason reported to Victor and had one-on-ones with him. Victor very much wanted the status and was frustrated when the status was not clear or lagging.   

Step 3: Still wearing my empathy shoes – Imagine what they would have wanted to do or experience differently…  

Both middle managers, Victor and Jason, felt the need to report status up the chain. They were providing status reports the same way they always have, but the teams changed how they deliver.  

Victor and Jason were facing two fronts: team level and executive. They were interacting on two completely different paradigms.  

Many of us have been in these shoes, and others can imagine a daily life where you interface between two completely disparate methods of work.  

Furthermore, you wish to please both sides; you want to provide clarity and status to leadership, and you want to let teams grow and develop. All leadership coaches tell you to allow teams to develop, but you also want to be a good follower. For Victor and Jason, leading teams and following executives was a complete daily schism.  

To avoid their daily schism, Victor and Jason want alignment on how to deliver and communicate the valuable work both up and down the chain.  

Step 4: How do we learn from their story and help others in their situation?  

We need that multi-directional alignment that Victor and Jason were missing and craving. As Agile Coaches, we coach alignment through the strata of an organization, so that the commitment to Agility connects from the teams to the executives. With this connection from teams to executives, middle managers are braced rather than squeezed.   

Supported middle managers are powerful advocates for Agile transformation.  

Starting with the Leading SAFe class, executives educate themselves, then continue their commitment through involvement in Lean-Agile Center of Excellence activities and a Go-See mindset.  

Safe for Teams classes allow education for team and technical agility, which continues in actions of relentless improvement.  

Without Coaches, all these learned skills deteriorate – coaching keeps us sharp! Even top-tier musicians and surgeons have coaches, and those practicing Agility continue coaching to keep an edge and avoid bad habits. Anyone who has learned a bad golf swing can attest that it would be better to learn a habit correctly rather than break an existing ill-formed habit. brings years of coaching and consulting experience with SAFe. We have cleared and certified SAFe Program Consultants (SPCs) embedded in multiple government programs, assisting them on their Lean-Agile journey and producing significant results in a short amount of time. can help whether you are just starting or have been Agile for a while, but not seeing the expected results.  


About the Author

Stephanie McCormick is a Senior Instructor for Agile Training Services at She started her Agile career in a custom dev shop after years of struggling with waterfall projects. Since starting her Agile journey, she has enthusiastically embraced roles as a product owner and scrum master and is now a SAFe Program Consultant and Certified Scrum Professional. She looks forward to a bright future of predictable, sustainable delivery of delightful products.