Why Leaders Hesitate to Let Go — and How to Offboard Well

Letting go of an underperforming employee is one of the hardest parts of leadership. Most owners and managers I work with know in their gut when it’s time, but they hesitate. Usually for two reasons:

1. Personal loyalties and guilt.
2. Fear of what will break in the process — and not wanting to deal with the mess.

Let’s break these down.

The Emotional Side: Why Leaders Drag Their Feet

If you’re not happy, they’re probably not happy either. Letting someone go frees them up to find a role where they can thrive.

Ask yourself: are you their friend, or their leader? Leaders make tough calls for the good of the whole. Keeping someone in the wrong role isn’t kindness — it’s holding both of you back.

And don’t fool yourself into thinking it’s “no big deal.” Underperforming employees drain your organization’s energy, morale, and productivity. Every day you delay, you’re prioritizing one employee’s feelings over your dreams, your family, your customers, and your team’s wellbeing.

The Practical Side: Yes, Offboarding Takes Work (But Less Than You Think)

Yes, offboarding is a process. Yes, it’s inconvenient. But in my experience, it’s never as bad as leaders fear. With the right checklist, you can move through it cleanly and protect the business.

Here’s what to do before you cut the final check:

1. Secure Access and Passwords

• Collect all login credentials (email, file systems, project management tools, CRM, laptop).

• Navigate two-factor authentication while the employee is still present.

• Confirm you can get into everything.

2. Restrict Digital Access

• List all apps, software, and systems the employee uses.

• Switch sensitive files to “view only” now.

• Remove access entirely on their last day.

• Restrict access to financial documents immediately.

• Delegate this process to a trusted admin for future offboarding.

3. Collect Company Assets

• Laptop

• Cell phone

• Credit card

• Equipment or tools

• Company vehicle

• Property keys

Make sure all assets are returned before releasing the final paycheck.

4. Manage Project Handoff

• Schedule twice-weekly check-ins for up to a month (depending on notice period).

• Provide a simple project status template. Each meeting, review:

  • Active projects and deadlines

  • Current status and blockers

  • Key contacts or handoff notes

  • Any “loose ends” or problem areas

Final Word

Offboarding is never fun, but it doesn’t have to be scary. With the right structure, you can protect your company, free up your energy, and open space for the right people to thrive in the role.

Letting go is an act of leadership. Do it cleanly, do it kindly — and then move your organization forward.

Looking for support offboarding an employee well? That’s what I do. Contact me to discuss.