Your oldest employees may be the ones getting ready to leave.

ISSUE #38 • WEDNESDAY, OCTOBER 21, 2026 • 5 MIN READ

Good morning. Thanks for opening Still Monday. Keep sending it to the person at work who remembers why the spreadsheet has that mysterious extra tab nobody is allowed to delete.

Today is about retention, but not the group companies usually panic about. New data suggest some of the employees most likely to be reconsidering their future are also the ones organizations often assume are settled.

That assumption can get expensive.

Eagle Hill Consulting's Q3 Employee Retention Index fell 2.1 points to 102.1, its lowest level since 2024. The more interesting movement is underneath the headline: retention sentiment dropped sharply among Baby Boomers and Gen X while Gen Z moved in the opposite direction. Eagle Hill Consulting

Baby Boomers fell to 90.5, down 6.3 points in the quarter. Gen X dropped to 93.8, down 5.3. Millennials slipped slightly to 106.8. Gen Z rose to 112.8, creating a 22.3-point gap between the youngest and oldest groups, the widest in the index.

There is an easy way to turn this into a generational story. That would miss the useful part.

A lot of companies quietly treat long-tenured employees as low-risk. They know the system. They have established relationships. They have survived enough reorganizations to stop reacting visibly to the next one. That can look like loyalty. Sometimes it is simply patience running out.

The operational risk is different from losing a newer employee. Experienced people often carry undocumented context: why a customer exception exists, which supplier needs extra follow-up, what failed the last time the company tried a certain change, who can solve a problem without escalating it, and which process in the SOP is technically correct but practically useless.

When that person leaves, the vacancy is only part of the loss. The company also loses shortcuts, relationships and memory that were never written down because everybody assumed the person would still be there.

Eagle Hill also found culture sentiment deteriorated across nearly every workforce segment. Its release specifically warns that the sharpest declines were among workers who often hold institutional knowledge and help prepare future leaders. Eagle Hill

The management response should not be a special generational retention initiative. It should be a better question: where are we relying on tenure as a substitute for engagement? The employee who never threatens to quit may deserve more attention than the employee who talks about career development every month. Silence can mean satisfaction. It can also mean somebody has stopped negotiating with you.

Gen Z's retention index rose to 112.8 while Baby Boomers fell to 90.5. That 22.3-point spread is the largest generational divide Eagle Hill has recorded.

Compared with a year earlier, retention sentiment is weaker for Baby Boomers by nearly 10 points, Millennials by 7.4 and Gen X by 3.4. Gen Z has strengthened by nearly 7 points.

The index's culture measure deteriorated broadly. Experienced employees also have more history against which to compare the present. They know what the organization used to feel like, not only what the latest values slide says it is.

Pick the five people whose departure would create the most confusion. For each, list the customers, decisions, systems and unwritten knowledge that depend on them. Then assign a second person to learn one piece of that context this month.

This is useful even if nobody leaves. Knowledge shared across two people is easier to improve than knowledge trapped inside one calendar.

The salary of a long-tenured employee may be easy to see. The cost of replacing their judgment usually is not. Recruiting, onboarding and ramp time are obvious. Customer history, error prevention and informal coaching are harder to price until they disappear.

Retention spending should reflect the value at risk, not just the probability that someone will resign.

CEO: Who knows how this process works?

TEAM: Dave.

CEO: Who is Dave's backup?

TEAM: Dave's notebook.

CEO: Where is it?

TEAM: Dave knows.

If a process only works because one experienced person remembers how to rescue it, that person is part of your infrastructure.

Vote below and tell us whether your company is good at transferring knowledge before people leave, or mostly excellent at discovering what they knew afterward.

Technically Wednesday. Emotionally asking Dave where the file is.

— The Still Monday Desk