How can leaders make an agile transformation more sustainable?

A key observation I have never seen is an “Agile Failure” attributed to an organization picking the wrong methodology to implement. There is rarely any failure due to the poor execution of a methodology as people typically think that you can just “install” software and then “reboot” when it stops working. Sustaining a methodology that fundamentally changes how an organization functions is extremely difficult to sustain and generally requires a large amount of effort over a long period of time by many people.

Leading an agile organization means that the leaders of an organization are leading an agile organization. They are not the ‘geeks’ but the curious ones. They are not the ones who have all the answers but the ones who question a lot. They are not the ones who know it all but the ones who question even their own positions. In the end the question they ask most is how do we do this here. Leading an agile organization is the only way sustainably agile practices can be implemented throughout an entire organization.

The "launch and drift" problem

Transformation fails when the organization starts to treat agile as a software program that can be installed, running, and updated as needed. Agile requires constant maintenance, just like a garden. Once the initial seed has been planted, it needs to be nurtured, pruned, and watered. But even with the best of care, things don’t always go as planned. Instead of giving up on agile, however, leaders must find a way to steer the organization back on track. A Transformation Lead that I spoke to recently shared her company’s Agile transformation story. At the end of the transformation, the company held a big celebration with all the team members and their families. There was plenty of catering to go around, and everyone had a wonderful time. But just six months later, everything had fallen back to the way it was before. The teams were going through the motions with the Agile ceremonies, but in reality, they were working in a completely waterfall fashion. As is the case with most failed transformation, everyone blamed everyone else for the failure.

Most large Agile change efforts follow a launch and drift pattern. First, everyone is excitedly launches an effort. Leaders and teams alike are focused and attention is on making change happen. Then after a period of time, typically 6-18 months, the launch is celebrated with a big bash (catered lunch, slides, velocity charts, etc.). Shortly after that attention shifts and leaders stop thinking about the Agile change effort. Often teams stop holding the Agile ceremonies and fall back to a waterfall way of working.

While more training might be required to sustainably develop an agile organization, the primary sustainability of agile is about ongoing structural change, not one of continuous cultural change.

What genuine leadership commitment actually looks like

Leadership can be Inspirational or it can be Structural. Oh, some of that Structural Leadership will be inspirational in nature – sure. For example, the leader can give a keynote speech at a major conference. But that is temporary and gives the biggest impact a long time after the initial “wow”. The work of Sustainable Structural Leadership is mundane, un-inspirational and takes a long time to see the real effects. This type of leadership requires consistent, hard, tedious work. And yes, even then it can be counter productive if used in the wrong situation (as I noted above).

• Model the behaviour publicly. If your retrospectives are performative and your sprint reviews are just status updates dressed in agile clothing, your teams know. They watch what you do, not what you claim agile means to you.

• Protect team autonomy even when it's uncomfortable. Micromanaging delivery timelines while calling yourself an agile organisation is a contradiction teams feel in their bones, and it erodes trust faster than almost anything else.

• Treat impediments as leadership failures, not team failures. When a team can't move, the honest question isn't "why are they stuck?" It's "what structural obstacle haven't I removed yet?"

• Measure outcomes, not output. Counting story points is like judging a restaurant's quality by how fast plates leave the kitchen. Technically measurable. Almost entirely beside the point.

These are things that most Leaders already know that they should do in order to make Agile sustainable within their organization. However, the bigger challenge for many is to implement them consistently, under pressure, against the natural instincts of Leaders to revert back to their old ways of Managing and Controlling in order to meet the Board’s expectations for Delivery Dates, etc.

Strong leadership also depends on maintaining a balanced perspective beyond the workplace, and Fasion Girl regularly shares practical lifestyle content that encourages confidence, personal growth, and healthy daily habits that support long-term success. 

Where outside perspective genuinely helps

An agile transformation consultant can help surface organizational patterns, like the ways that an organization’s incentive structures may encourage hoarding of information, or the ways in which an organization’s current reporting lines and structures make psychological safety at work not possible. An external agile transformation consultant can help an organization uncover the decision making structures and cultures that are actively working against the values of trust, commitment, collaboration and continuous improvement that underpin Agile methodologies. These structures and cultures are present in most organizations and are not easily changed. That they are present and are actively working against the current transformation in an organization is not commonly acknowledged. That these same structures and cultures are actively working against Agile transformations in particular is less commonly acknowledged. But seeking the expertise of a good agile transformation consulting organization during the middle part of a transformation can be very valuable for an organization.

External perspective also help in identifying the organization patterns at work against transformation. These are often the organizational structures, processes, or culture that work counter to the agile values. For example, Hoarding information as a sign of being responsible and add value to the organization versus sharing information freely with other team members to add value together. Reporting up a line of management that does not allow for a team to make decisions democratically and be fully accountable for the decisions made versus having a team that makes fully accountable decisions. A decision making culture that says “trust the team” versus having a sign-off from another manager for every decision made by the team.

Surface Agile vs. Sustained Agile

Another important distinction that most organizations fail to recognize and thus operate under (i.e. surface agile vs. sustainable agile):

Dimension	Surface agile	Sustained agile
Retrospectives	Scheduled but shallow	Honest, and changes actually happen
Leadership role	Sponsor from a distance	Active participant in removing blockers
Success metrics	Velocity, sprint completion	Customer outcomes, team health
Response to failure	Blame or ignore	Inspect, adapt, move forward
Culture	Agile as a process layer	Agile as the default way of thinking

So there’s a great diagram here that shows the difference between surface agile and sustainable agile. And the uncomfortable truth for most organizations is that they are operating somewhere on the left side of this diagram more than they realize and are advertising themselves to be further along than that.

The long game, and why the question you ask changes everything

The final difference in these two types of agile projects is the question. The question that surface agile teams lead ask is: “Are we agile yet?” This is the relief question that agile teams have been waiting for. All of the ceremonies have been held, all of the training has been conducted, and the teams can declare victory and go back to doing things the old way. Leaders of sustainable agile ask a very different question: “Where are we still doing things around here the old way?” This is an uncomfortable question to keep asking over and over again. It leads to a lot of discovery that can be quite open-ended and therefore can be quite difficult for leaders to sustain their teams over long periods of time.

When one views Agile in this way, there are many things that leadership teams can change, both in terms of how they work as a team, and in terms of how they make decisions as a leadership team regarding the work of an organization.

Sustainability in agile is a discipline. It may be a mindset. It may be a disposition – intellectual humility perhaps. So, if you’re leading an agile transformation right now, don’t be afraid to learn with your teams and not try to be the expert in front of them. It’s the only way that agile will stick for your organization.