How to lose an employee in 10 days

Poorly managed transformation can turn uncertainty into disengagement and send talented employees quietly looking for the exit.

There is a 2003 romantic comedy by a similar name. The premise is simple: a magazine writer sets out to drive a suitor away using every annoying, clingy, and irrational behavior she can manufacture. She follows an intentional playbook of self-sabotage. The guy, pursuing his own agenda, is left frustrated and confused by how her behavior affects him.

I think about that movie every time I watch an organization go through a major transformation. Because somewhere out there, in boardrooms and all-hands meetings and transformation rollout plans, leaders are following a strikingly similar playbook. Not intentionally, of course. No one sets out to chase employees away. But the result is often the same: a workforce that feels confused and undervalued, and begins quietly looking for the exit.

If, during your next transformation effort, you are determined to lose your employees, here are five ways to do it:

1. Start by keeping “the why” to yourself. Leadership teams spend weeks, sometimes months, analyzing the case for change. They study the data, debate the options, and eventually arrive at a decision that feels obvious to everyone in the room. Then they announce it to the organization and are genuinely puzzled when people seem unsettled.
   What they forget is that the people most affected by the change are hearing about it for the first time. They haven’t had weeks to process it. They haven’t seen the analysis. All they know is that something significant is about to happen to their daily work, their relationships, and possibly their role. Expecting them to immediately embrace a change that leadership has already fully digested is a bit like finishing a novel and then being annoyed that someone who just picked it up doesn’t know how it ends.
   In a merger, this plays out with a particular edge. Employees of the acquired firm often don’t know why the deal happened, what it means for them, or whether their jobs still exist. A press release is not a communication plan.
2. While you’re at it, don’t explain how leadership will change either. Few things create anxiety faster than organizational uncertainty. Who is in charge now? Who do I go to with problems? When the hierarchy shifts but nobody explains the new one, people fill the silence with speculation. And speculation is almost always worse than the truth.
   In a transformation or merger, leadership transitions deserve explicit, deliberate communication. Not just an org chart update buried in an intranet post, but real conversations about how decisions will be made, who has authority over what, and what continuity looks like for the people doing the actual work. Skipping this step doesn’t make the uncertainty go away. It just makes people feel like nobody thought about them.
3. Don’t honor the past. Transformations often come with an implicit message: what we were doing before wasn’t good enough. Sometimes that’s true. But the people who built what came before were doing their best with what they had. Dismissing the past – the culture, the processes, the relationships – without acknowledging what is worth keeping sends a painful signal to the people who lived it.
   Good change management doesn’t pretend the past didn’t happen. It says: here is what we’ve built, here is what we are proud of, and here is why we believe the next chapter requires something different. That sequence matters. It is the difference between a team that feels like it’s growing and one that feels like it’s being erased.
   This is especially delicate in mergers. When one firm absorbs another, the acquiring organization sometimes behaves as though the acquired firm’s history simply doesn’t count. Client relationships built over decades get transferred without a conversation. A senior project manager who has worked with a client for 20 years suddenly finds someone else making decisions about that account. Trust in the relationship was earned. Treating it as a transferable asset on a spreadsheet is a reliable way to lose both the employee and the client.
4. Be liberal with new tools and metrics. A classic transformation move is to hand people new software with minimal training and wish them well. Log-ins distributed. Implementation declared complete. What could go wrong?
   Quite a lot, it turns out. Systems change requires process change, and process change requires people change, and none of those things happen without time, support, and genuine investment. Rolling out a new project management platform to a team that was never asked how they currently work is a fast track to low adoption and quiet workarounds.
   The same logic applies to metrics. Holding a newly acquired firm immediately accountable to internal performance benchmarks they have never tracked before is a great way to communicate that you don’t particularly care whether they succeed. Give people time to learn the language before grading them on the exam.
5. Assume integration can be managed as a side project. Transformation initiatives have a way of being assigned to people who already have full-time jobs. Someone from HR will lead the change management effort – right after finishing their regular HR responsibilities. The operations team will document the new processes – while still running current operations. The integration committee will meet monthly.
   This approach treats one of the most complex and human-intensive challenges an organization can face as something that can be handled in the margins. It almost never works. The organizations that navigate transformation well tend to be the ones that treat it as real work, assign real resources to it, and give people actual permission to slow down their normal pace in order to do the transition right.

Here is what all of these missteps have in common: they prioritize the mechanics of change over the experience of the people living through it. The new system matters more than whether people understand why it’s being implemented. The org chart matters more than whether people feel seen in the new one. The timeline matters more than whether trust survives it.

Organizations that get transformation right don’t just manage the process. They tend to the people. They communicate early and often, even when the answers are incomplete. They acknowledge what is being left behind. They give space for questions, for adjustment, and for the inevitable messiness that comes with genuine change.

The movie, of course, ends well. Despite her best efforts at sabotage, the relationship turns out to be stronger than the playbook. Real organizations don’t always get that ending. The talent that walks out the door during a poorly managed transformation rarely come back. The client relationships damaged during a clumsy merger are hard to rebuild. The culture that quietly eroded while leadership was focused on the mechanics of the deal is very difficult to recover.

So, before your next transformation kicks off, it might be worth asking a simple question: are we managing a process, or are we leading people?

The answer to that question will determine a great deal about how the story ends.

Greg Sepeda is a former engineering manager and is currently rewired as a management consultant. Connect with him on LinkedIn.