As leaders we spend enormous amounts of time and energy preparing for transformation—defining the vision, building the roadmap, selecting technology, redesigning processes, defining new roles, and establishing governance.
The next step too often is that we turn to middle management and, explicitly or implicitly, say, “Now go make it happen.”
That’s where many transformations begin to struggle and fail to move beyond the planning stage. Not because managers don’t believe in the change. Not because they aren’t capable, and not necessarily because they are resistant.
We need to accept the truth that we haven’t prepared them, the transformation, or the organization to be successful.
Transformation Happens in the Middle
We tend to think of transformation as something driven from the top. Direction certainly is, execution is not.
Transformation happens through hundreds of decisions made every day by managers leading teams. They determine what gets prioritized. They answer questions when employees are uncertain. They decide how aggressively to adopt a new process. They determine which old behaviors are tolerated and which new behaviors are reinforced.
Those seemingly small decisions ultimately determine whether the future state becomes reality or the organization gradually drifts back toward what it knows. Without the proper support and leadership, the pull to old ways of working typically wins.
We’re Asking Managers to Run Two Businesses at Once
The problem is that transformation doesn’t simply give managers something new to communicate or enforce. It effectively gives them two jobs to do and two types of business to support.
Managers, supervisors, and directors are the core of running a business. They are key to meeting customer needs, hitting revenue targets, completing projects, addressing problems, and coaching and training employees.
None of that stops when a transformation begins. We ask those same leaders to build tomorrow’s business through designing and implementing new processes and technology while answering employee questions and driving a change in behaviors to meet the transformation goals. We are essentially asking them to lead two businesses at once: the business we have today and the business we are trying to create.
Yet we rarely create the capacity or build the capabilities necessary to do both.
In a conversation with a client that is going through a transformation due to rapid growth, we began discussing how the work to scale outdated processes, increase manufacturing capacity, and move to a new ERP system was going to take place, while also keeping up with current customer demands, ongoing strategic projects, and the day-to-day activities of the business. The scary answer that came back was, “We will just have to ask people to work harder.”
When transformation activities inevitably compete with immediate customer or operational needs, today’s business usually wins. This causes the transformation to stall, the benefits to be delayed, and the confidence in senior leadership to erode.
Build Leadership Readiness Before Organizational Readiness
If organizations are serious about transformation, they should treat leadership readiness as a transformation workstream of its own. Deliberately invest in preparing the people who will ultimately translate strategy into everyday behavior.
That means preparing managers to lead through ambiguity. Giving them frameworks for making decisions when information is incomplete. Helping them recognize and respond to resistance. Equipping them to communicate uncertainty without creating fear.
Perhaps most importantly, organizations need to give managers something transformation programs rarely provide: permission and time to learn before they’re expected to lead.
There is a big difference between telling managers what’s changing and allowing them to work through what that change means for themselves and their teams. If transformation truly matters, leaders need to create capacity for middle management to engage with, challenge, adjust to, and adopt the changes that are to come.
With the company above, once everyone realized that they couldn’t just assume middle management would figure it out, we developed a solution to manage day-to-day business while preparing for the transformation. Growth was going to require hiring additional people. We added capacity to the front lines and created team leader positions to develop rising stars in the organization, which ultimately created capacity for current middle managers to focus time on the transformation. This drove excitement for the change because it was already creating new opportunities for people. It also allowed middle managers to coach and mentor new team leaders on the desired new ways of working.
Prepare Those Who Make Change Stick
Every day, managers decide where attention goes, what gets prioritized, which problems matter, and which behaviors are reinforced. Collectively, those decisions determine whether a transformation becomes how the organization actually operates or remains just a program managed by a project team.
If you want better transformation outcomes, stop assuming middle management will figure it out. Prepare them. Develop them. Create capacity for them. Empower them to lead.
October 14, 2026
