What Does Leadership Do During an Agile Transformation?

The entire org chart has a vital and critical role to play in an agile organization. That doesn’t mean getting there will be easy. In fact, if it isn’t…you’re probably doing it right.  


In our line of work, we hear this a lot: “We started our Agile transition, but then we got stuck.” What we normally like to point out is that getting unstuck is part of the process for everyone. Getting unstuck can also be prescriptive, because diagnosing and moving through those stumbling blocks reinforces the core components of Agile itself.  

Leadership and management figures can sit at odds as they lead different teams through a process that is, frankly, hard to measure. Let’s put this gently: The least adaptable people in your organization are always uncomfortable with something new, let alone something as misunderstood as an agile mindset. The good news? There’s quite a lot that you can do to reassure them, work with them, and put the control back into the hands and minds of the teams where it belongs. 

When the Transition Starts at the Very Top  

C-level leaders usually are drawn to Agile because they believe, rightly or wrongly, that it promises greater efficiency and a tighter bottom line. They’ve been told, and they’ve read, that an Agile transformation will put them on pace with the competition (if not ahead of it) and transform customer relationships and products.   

Your CEOs, CTOs, CFOs likely understand and embrace the need for innovation and creativity. But (once again, tell you something you don’t know, right?) while they hold the keys to your company strategy, they may be unaware of how those strategic changes are processed downstream. Leaders are also tasked with balancing the rigors of compliance (especially in tech environments that deal with highly regulated industries like healthcare, finance, and education) along with creativity and innovation.   

They may also be a bit unclear as to what the process itself should look like. Being a proponent of change is hard if you aren’t clear in how to navigate the process. That disorientation breeds its own form of misinformation and fear.  

Solution: Collaborative Agile Organizational Team  

Agile isn’t a one-and-done change. It’s a process of constant adaptation. Work with your C-level leaders to create an organizational structure that is more in line with agile mindsets. Putting them in charge of that process, and becoming their ally in it, brings you both into the process together collaboratively.   

Organizational restructure doesn’t mean sweeping layoffs and spending massive amounts of capital on hiring brand new agile leadership teams. It does mean nominating the right leaders within the company to take part in a collaborative agile leadership team or an Agile center of excellence. That team becomes the holder of the Agile keys, so to speak, a sort of brain trust for the transformation. Ideally, that team should consist of the company’s senior leadership including:  

  • CEO  
  • HR 
  • Finance 
  • Marketing 
  • Technology 
  • Product 
  • Operations

If you put this team in charge of diagnosing and then prescribing the solution for each different problem as it arises, you are all able to address your cultural goals at the same time. As much as it will be tempting to dedicate meeting time to operational issues, use this time to map out strategic solutions.  

Clarifying the Role of VPs and Senior Directors 

VPs and senior directors often feel like the organization’s “middle children” during a transformation. They are under significant pressure from the C-suite to “make this Agile thing work” and have the additional burden of pushing middle management to, well, make this Agile thing work.   

While it’s not an enviable position, it’s a very powerful one. Those very leaders are in the ideal position to lead by example.  

Solution: Delegation and Training  

The moment that one of your software developers or VPs notices a broken link in the chain, they are in the best position to delegate operational and day-to-day tasks to their direct reports. They are some of the most critical executioners of company strategy, they are also the best positioned to reiterate the goals of an Agile transformation. When their teams become overly attached to conceptual ideas (“We have to do things faster!”), the whole process gets mired. Team leaders and project managers then often lose sight of the whole picture, become more controlling, and lead to bottlenecks.   

First step, get everyone the Agile training they need. Second, revamp job descriptions and responsibilities that are inline directly with the transformation. When you remove gray areas, you also remove confusion and restore confidence in just what and how this role will look moving forward.   

Lastly, leaders need daily stand-ups with each other, in addition to regular facetime, as a group, with the Agile collaboration team. If there’s a theme developing here it looks a bit like this:  

Collaboration + Delegation + Communication = Frictionless Agile Transformation  

Helping Mid Management Succeed During a Transition  

Management often doesn’t quite understand what a post-Agile role looks like for them. If your managers are more concerned about losing their jobs after an Agile transformation, they are likely to turn that fear into control.   

That very control will stifle your transition. Management isn’t obsolete in every Agile transformation, but strict oversight by that management is the direct opposite of Agile. Until they understand what their new role is and how to reinforce it, that fear isn’t going anywhere. Consider that all successful bands have a manager. Does the manager play an instrument or write songs? No, but the manager schedules and often books gigs, oversees the royalty payments, takes care of finances, etc. How far does a good band go with bad management?  

Your managers may be okay once they get some coaching in just how to adopt an agile mindset and lead with it as well. How can they lead if they don’t speak the right language? In Agile, management’s primary function is to enable capacity and flow. The team needs this manager’s experience and strategic mind to get unstuck.  

Fast Solution: Team-Based Performance Reviews 

Most agile organizations move away from individual reviews and replace them with team-based reviews. Agile organizations embrace transparency. Managers are the enablers of that transparency, and performance is something that should be revisited regularly. So, cancel the annual one-on-one review in favor of cooperative, team-based collaborative discussions about process.  

Leadership Problem: Interdepartmental Conflict  

We reassure organizations all the time that an Agile transformation often highlights areas of the company that weren’t already healthy. Where there was already interdepartmental friction, those fissures become even more apparent and obvious.  

Solution: Revamp the All-Hands 

Oh, the all-hands. So important, so misunderstood, so misused. How can you structure the all-hands to be interactive and holistic rather than a roll call or an “okay, your turn” show-and-tell from each department head? When an employee’s precious time is misused or misspent in an unproductive meeting, they are likely to resent both the misuse of their time and the colleagues who are misusing it.  

Interactive retrospectives aren’t just mandatory for your Agile transformation, but make for a healthier and more supportive culture. When your meetings feel long-winded, repetitive, or aimless, someone needs to be brave enough to suggest that an experienced Agile coach is just the right ingredient to bring in to revamp this entire process.   

Nothing of real value is ever particularly easy. We don’t become or stay healthy with just one visit to the gym, and musicians need hours and hours of practice to master an instrument. Just as Agile isn’t a linear experience, transformation isn’t ever really finished.   

Getting stuck is also part of the process, but there’s no need to stay stuck. If you could use some help, we’re here to provide the coaching and training that you and your peers need to become a vital, supportive, and productive company. Reach out anytime. 

James Nippert

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