Using Agile to Manage Your Enterprise Agile Transformation

Over several years of working on Agile transformations, I’ve seen the whole spectrum of issues, ideas, and idiosyncrasies.

Some organizations want a pixel-perfect plan for their entire transformation before they buy one single sticky note.

Others demand agility of their employees practically overnight, providing little to no preparatory training.

As you might imagine, neither approach is ideal.

What we need is a Goldilocks approach to Agile transformation. Unsurprisingly, that means we need to take a truly agile approach to going Agile.

To help show where that middle ground lies, we’re first going to hear the stories of two extremes.

The Agile Transformation that Wasn’t

Facing increased competition in their sector, senior executives at an alcoholic beverage company were considering taking their marketing department Agile. Part of what they were considering was using marketing as the leading edge of a larger Agile transformation throughout the organization.

But as they learned more about what Agile really means and the difficult journey they’d need to make to achieve it, the ensuing discussion I led with them went in an odd direction.

The execs kept asking very specific questions about timing.

After a few probing questions, it became clear that what they really wanted was a precise, down-to-the-week schedule for the next five years of their proposed transformation.

Gantt charts, hyper-detailed project plans, and a rigid calendar were how they planned to effectively transform themselves to an Agile organization.

Knowing what I did about how these kinds of efforts go, I did my best to convey the uncertainty that comes with any such project. We could predict how the first six, and maybe even nine months would look. Beyond that we simply don’t know.

We would need to embrace the spirit of agility upfront and recognize that our plans, no matter how thorough, would likely not survive the first contact with reality.

The unenthusiastic response to this was palpable. That organization remains steadfastly waterfall in marketing and elsewhere.

Agile Transformation Without a Plan

Standing in stark contrast to these planning fanatics is a communications organization that was overzealous in their approach to Agile transformation.

Their advantage was that agility existed in pockets inside the organization, and they even had some full-time Agile coaches on payroll.

The problem here was that their existing Agile capabilities made them overconfident.

They leaped into their Agile transformation inside of marketing without a viable plan, ultimately endangering their efforts just as much as the group who never even started.

Multiple training sessions were delayed, which always risks undermining people’s belief that the change will ever actually happen.

During course content customization sessions there were several topics we couldn’t tailor because they hadn’t yet determined how they would approach them.

Should we cover estimation? Nobody was sure if there would be an expectation or capability to do so.

How would we address new paths to professional advancement post-Agile? Human resources was still figuring it out.

Was there an idea of which teams would be in the next wave of trainings? Nothing was mapped out beyond the first major wave.

The jury’s still out on how this particular transformation will play out, but the first steps have been wobbly at best.

Using Agile to Execute an Agile Transformation


I’m not sure why it’s so easy to forget Agile best practices as soon as the conversation turns to transformation. They should remain our guide here just as much as they are when we’re actually doing work.

For example, “responding to change over following a plan” should be the governing value when designing an Agile transformation roadmap. We should know the ultimate destination we want to reach — in this case marketing and/or organizational agility — but we should be ready to adapt our route based on incoming data.

We wouldn’t map out a minute-by-minute plan of a long road trip and then follow it relentlessly, no matter the changing conditions around us.

Neither should we create a day-by-day plan for an Agile rollout and march forward with it no matter what happens.

Instead, we need a transformation blueprint.

It should give us enough information to start intelligently, but it should also “welcome and plan for change.”

How to Phase Your Agile Transformation

At AgileSherpas, we break transformations into four phases as part of our Marketing Agility Ascension©:

  1. Gathering Supplies: determining why you’re going Agile in the first place, how you’ll measure the success of the effort, and what the general rollout plan should be. Teams should clearly understand who’s going first, why, and how the next waves will be determined.
  2. Initial Climb: Run several pilot teams (the right way) and begin instilling new Agile habits with leadership.
  3. Building Base Camp: create a reference model based on pilot learnings that will provide the baseline for new Agile teams. New teams begin to spin up based on this model, and all leaders complete their training and coaching.

Agile Ascension: any remaining teams transition to Agile ways of working. Success metrics, while monitored throughout the transformation, are formally presented and analyzed. Internal resources, i.e. coaches and trainers, are prepared to shepherd the organization through the rest of their journey.

The 4 stages of marketing agility ascention illustrated as label above a mountain

We never design more than two phases of this Ascension at a time. This is because we recognize that later phases will be significantly different based on what happens in early ones.

But we know generally what’s going to happen later on in the Agile transformation, and so does everyone involved in the effort. This is how we navigate the path between excessively detailed plans and diving in with no map whatsoever.

Create Ownership for Your Agile Transformation

In addition to planning the right way, you’ll have your best chance of a successful transformation if you identify a core group of leaders to own the effort.

This should be a fairly cross-functional group, meaning they have enough knowledge and clout within the organization to drive the transformation forward.

They’re the ones who make sure the transformation plan is clear and well communicated.

They own training schedules and make sure people show up at the right time.

They vet any external vendors who’ll be involved, and they select new tools if technology is needed to support the transformation.

Generally, their job becomes steering the ship towards agility.

Salesforce is a great example of this being done right. They had a committee responsible for their Agile transformation and consequently managed to transition hundreds of people in less than a year.

If agility isn’t someone’s core responsibility, it’s much more likely to fall to the wayside and be neglected after a few months, just when it needs attention the most.

Balancing Too Much Planning and No Planning at All

Agile transformation is a tricky undertaking. It can be tempting to over-engineer it or become so overwhelmed by planning it that you just start without a design.

Don’t make it harder by falling victim to either of these extremes.

As in all things, rely on Agile values to construct your transformation plan. And, of course, AgileSherpas is here to help if you need a hand.

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