Transforming an organization is messy and often unrewarding at the end. It takes time, leadership fortitude, and a unique blend of strategic skills, communication skills, the ability to build trust, and the ability to adapt on the fly.
And it’s unavoidable. Organizations have been evolving over the past decade to the current state where transformation is continuous. The most recent driver is AI and emerging technology, but this is just the latest reason. If you look back over the past decade, organizations have had to adapt to changing supply chains, increased product personalization to the buyer, remote and hybrid ways of working, changing regulations, partnerships, private equity, and the list goes on and on.
The unrewarding feeling comes from the length of time to get to results, the grind it takes on everyone involved, the fact that most transformations don’t result in the value expected, and the knowledge that another transformation is beginning before the last one ends.
Planning Is Part of the Problem
Despite all that, there is still a tendency to build the entire plan up front, so we can commit to leadership or boards when the impact will hit the bottom line or when we need resources. As executives, we want, and sometimes need, definitive answers and ways to measure the progress of others, the business, and our own success.
The truth is, you won’t be able to plan all the details, so stop wasting your time. Transformations by their nature take months or years to complete and involve multiple functions and often hundreds or thousands of people. That level of complexity makes the detailed planning we would all desire as executives nearly impossible.
And our innate need for a fully established plan can limit innovation and creativity at the very points in the transformation where new pathways may become clear. Transformations come with thousands of decisions, big and small, and each of those decisions carries learnings, clarity, and greater direction with them. The ability to adjust thoughts, plans, and approaches while keeping the vision in mind enables the team to move faster and not be beholden to a detailed, out-of-date plan.
A More Nimble Approach
Instead, consider the concept of “rolling planning.” It is applied in revenue forecasting, but not often to organizational transformations, and it should be. Planning from one major decision point or key achievement to the next allows teams to adjust to new information, risks that have become reality, and changes in personnel.
When a consumer goods company looked to shift to a direct-to-consumer model instead of just going through retail stores, they had to reimagine how their processes and systems would work for orders, manufacturing, and distribution. Each decision had a ripple effect on other decisions, approaches, and timing. Instead of spending unproductive time building a schedule that would only be refined over and over again, still without clarity on what the future would hold, the team used rolling planning to adapt to new information and new ideas. Ultimately it allowed them to spend more time advancing the project, ideating better solutions, and proactively addressing issues. Looking back, it also reduced the amount of rework that would have been needed if everyone had charged ahead with a plan built on a large number of assumptions.
Rolling planning essentially shows up in three steps. This is how we put it to work at the consumer products company.
1. Define the Vision
Paint the picture for the organization on what the future will be, why the transformation is critical, and the impact it will have for the greater good. This allows everyone to understand the direction, visualize the future, and begin to imagine how their ways of working will change. Focus on roles and behaviors, not on specific process changes. Those are details to define later in trainings, and they aren’t the emotional connection that is necessary up front. The transformation vision holds the rolling plan together as everything else moves around it.
2. Empower Middle Management to Make Decisions
For large transformations, there will be thousands and thousands of decisions to make. Some don’t have a right or wrong answer, some will be inconsequential, and only a few will truly impact the outcome. The swirl of decision-making is a silent killer that eats away at the progress of the program. Empowering leaders to make the decisions, in alignment with the vision, improves the speed.
Leaders need to know when a decision is critical and how to escalate it. Meet with the leaders involved in the transformation to ensure a clear understanding of the vision and discuss when things need escalation. That might mean time impact, impact on other functions, or a set dollar amount. As a transformation leader, spend more time coaching on the logic applied in the decision-making than on the decision itself. Understanding the thought process and perspectives to consider improves decision-making, so a single person or governance team doesn’t become a pinch point for progress.
3. Plan Small and Act Immediately
We are often asked for the day or week a transformation is going to “go live” when it is still years away. Instead of planning for the end, plan key achievements that show you are moving in the right direction. With each achievement, find value that can be gained and communicated. At the CPG company, it was showing that a portion of product, in a limited market, could be moved to a new distribution method. That allowed the team to uncover more challenges, refine the next steps, and keep moving forward. Stagnation of the project team will not only impact the project, it will destroy morale and belief in the transformation.
Stacking up the small wins, continually moving forward, even when you have to course correct, increases cycles of learning and improves overall outcomes.
The Charge for Leaders
None of this works without the executives at the top. For rolling planning to take hold, executives have to provide a clear vision for the future and accept a level of ambiguity. Let go of the script and trust the cadence of the next decision over the comfort of a complete plan.
Transformations are messy. Simplifying the plan down to the key decision points, empowering the people closest to the work, and stacking small wins along the way will allow organizations to adjust in real time and spend more time on critical work.
July 1, 2026
