change management

The Art of Keeping Your Best: Employee Retention During Business Transitions

Let’s cut through the HR fluff and talk about what really keeps good people during tough transitions. Whether you’re scaling up, downsizing, or pivoting your business model, your success hinges on keeping your key players in the game.

First, let’s destroy a common myth: Money alone doesn’t keep great employees. I’ve watched companies throw cash at retention problems only to lose their best people to competitors offering less compensation but more stability and purpose.

Here’s what actually works, based on real battlefield experience:

Transparency Trumps Everything
Your smart employees can smell BS from a mile away. They know something’s changing before you announce it. The moment you start having closed-door meetings, the rumor mill starts churning. Beat it to the punch.

I recently watched a tech company lose half its senior developers because management thought they were “protecting” employees by withholding information about an upcoming merger. The competitors who hired them? They offered less money but clear communication about their future.

The Retention Formula That Actually Works:

Early Communication
Share the vision before the changes
Explain the why, not just the what
Be honest about challenges
Provide regular updates
Clear Individual Paths
Show each key player their future role
Define growth opportunities
Create transition-specific development plans
Offer skill expansion opportunities
Meaningful Involvement
Include key players in planning
Ask for and implement their input
Give them ownership of transition projects
Create transition task forces


Strategic Compensation
Front-load retention bonuses
Tie rewards to transition milestones
Create long-term incentive plans
Offer transition completion bonuses


But here’s what nobody tells you: You shouldn’t try to keep everyone. Use transitions as an opportunity to upgrade your team. Some people won’t fit the new direction, and that’s okay.

Signs Someone Should Stay:

Adaptable mindset
Solutions-focused attitude
History of growing through change
Strong cultural influence
Critical skills for future state
Leadership potential

Signs Someone Should Go:

Resistance to all change
Constant negativity
Skills that won’t fit future needs
Cultural toxicity
Unable to grow with organization


The secret sauce? Creating what I call “invested uncertainty.” People will stick with you through uncertainty if they feel invested in the outcome. Give them skin in the game.

Practical Steps for Creating Invested Uncertainty:

Share ownership in the transition
Create clear milestone rewards
Offer development opportunities
Provide decision-making authority
Build cross-functional responsibilities


Remember: The goal isn’t just to keep people – it’s to keep the right people and keep them engaged. Sometimes losing a few people who don’t fit your future is healthier than keeping everyone at all costs.