Packing for the Yellow Agile Brick Road: 5 Tips for A Successful Transition to Agile

By: Lorena Connolly | Nov 11, 2019 |  Agile Coaching,  Agile Transformation,  Article

Happy days. Your organization has made the commitment to experiment with Agile or to go whole hog and do a “rip-the-band-aid-off” transformation. Now, you’re learning about stand-ups, backlogs, and self-organizing teams. During this transition to Agile, you may be wondering, “What are we really in for?”

Indeed, you may feel like Dorothy in the Wizard of Oz. You’ve been spun around in a tornado of terminology and change. Now, you’ve landed in an unfamiliar place that bears little resemblance to the place you’ve been working at over the past few years. You really aren’t in Kansas anymore.

It is important that you learn the principles, values, and practices of an Agile way of working. Even after you complete your first training class, keep doing that. That is your Yellow Brick Road. 

This article is about the more elusive, yet essential things, you’ll need to take with you on your Agile journey. The help you need to battle the Wicked Witch of The Way We’ve Always Done Things and the Flying Monkeys of unplanned work, stories that carry over, and big batch work. 

Let’s get back home (though it may look different) and to a place where you feel comfortable and confident again. Here are 5 tips for a successful transition to Agile:

1. The Lion: Courage

The first thing you will need is courage. I just finished an engagement with a client, and as I said my good-byes, I wanted to leave them with a final shot in the arm to sustain them in the days ahead. We sent them medal stickers with the words “Change Takes Courage” emblazoned on them. A reminder that courage is foundational to work in an Agile way. 

You need courage to:

  • Ask the questions that break you away from the way we’ve always done things
  • Not succumb to the “fire of the day”
  • Say “No, that’s not going in the backlog”
  • Tell your boss to take his or her request for work to the Product Owner
  • Have healthy conflict and end with a better solution
  • Speak up and give your opinion, no matter who is in the room
  • Give and receive needed feedback
  • Be self-reflective
  • Let go of long-held management, process, and project control beliefs and work differently
  • Change and transition to Agile

Courage is at the very core of all Agile transformations. I see so many organizations where courage has been all but snuffed out by intentions both well-meaning and not-so-well-meaning. 

Whoa! If I only had some courage! The good news is that you do. It’s there within you. It may only be a little spark, but fan it with small acts of courage and, in no time, you’ll be marching into the Wicked Witch of The Way We’ve Always Done Things castle to vanquish her. 

Agile transformation will require courage from leaders, stakeholders, and teams. Be courageous and celebrate courage when you see it. When you see someone holding back you can use a permission-giving phrase to encourage that person to take the leap. Perhaps by saying “Put ‘em up! Put ‘em up!,” in your best Cowardly Lion’s voice!

2. The Scarecrow: Mindset

In Agile circles, we talk a lot about how Agile is not a process, methodology, or lifecycle. We don’t get the benefits Agile has to offer if we “do Agile.” We get the benefits when we ARE agile. That means shifting the way we think about how to work, how to interact with one another, and how to lead. 

More than memorizing the Agile Manifesto, principles, and values we need to think and act in concert with them. Only then can we transform and realize the business outcomes that Agile helps us achieve.

In practice, this mindset shift looks like this:

  • Turning away from the tyranny of the urgent and moving toward sustainability and predictability
  • Resisting going back to familiar (comfortable) processes and methods to forge new or repair relationships to have productive interactions
  • Moving from managing through status and reports to encouraging and supporting teams to meet their commitments, allowing working software to be the most important measure of progress
  • Enabling our teams by reaching out to our peers to solve long-standing systemic issues that have been a source of slowness all along
  • As a leader, resisting the urge to solve a problem you know how to solve and allowing the team to wrestle with it for a bit and solve it on their own
  • Instead of business and technology working separate from one another, because the other “just doesn’t get it,” both teams are being transparent with themselves and each other
  • Delivering value instead of delivering “deliverables”

Whoa! If I only had an Agile brain! The good news is that you do. It’s in you, it just may need a little rewiring. 

Be intentional in your thinking and decision-making. Ask yourself and others, “Does what we are doing align with Agile principles and values?” Truly explore the worst case scenario of not doing something, rather than responding to the urgent and often inaccurate, “we just have to do it.” 

As a leader, before responding, ask yourself, “Will my response empower my team and encourage ownership?”

3. The Tin Man: Compassion

The transition to Agile is challenging from a tactical perspective. 

It’s even more challenging from an interpersonal perspective. In my opinion, we don’t talk about or equip people sufficiently to deal with what we each experience during an Agile transformation. We teach how to write a user story–relatively easy. But teaching someone how to remain confident when their job, who they work with, and how they interact is significantly changing?  That’s much more difficult. 

As leaders and teammates, we need to have heart and give grace when people and teams:

  • Mess up
  • React emotionally
  • Try and fail
  • Need support in their new roles/jobs
  • Need to adjust

Whoa! If I only had a heart! You know you do. You just need to have the courage to let it show. 

Be willing to have conversations about “humanness” during your Agile transformation. By showing and accepting a little vulnerability, you will be amazed at the trust you can build even in this time of change.

4. Toto: The Friend

Toto was Dorothy’s stalwart companion. He would not abandon her and jumped off a moving bicycle to get back to her. Likewise, Dorothy would not abandon Toto and ran away from home to protect him. 

On this journey, you’ll be tested. You will doubt yourself. Expect it. You are trying new things! Find yourself a Toto to be your sounding board, your cheerleader, your sympathetic ear, and your voice of reason. 

Return the favor for your friend–and don’t let your friend get carried off by a flying monkey!

5. The Wizard: A Coach

The Wizard was ultimately able to help the Lion, the Scarecrow, the Tin Man, and Dorothy realize they already had what they needed within them. They had the power to change their circumstances, they just needed some coaching. The Wizard could see what was inside them, even when they were not yet able to. He didn’t fix their predicaments, he showed them how to fix them on their own. 

As you trek down your Agile Yellow Brick Road, you will need a Wizard. Someone to see what you can not yet see. Someone who has traveled this road many times and will help you solve your predicaments and challenges on your own. Someone to guide you away from the poppy fields and flying monkeys to keep you on course.

The Wicked Witch of the Way We’ve Always Done Things is extremely powerful and hard to resist. You need someone who has battled her before and won.


I hope these 5 tips help your Agile transformation go a little smoother, and I wish you a successful journey. 

If you are looking for a Wizard, give Agile Velocity a call. Or you can learn more about our approach to building lasting business agility on our Transformation Services page.

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