Five Questions Executives Should Ask Before Their Most Experienced Employees Leave
What happens when your most experienced employee leaves and takes years of knowledge with them? Too often, organizations don't realize what they've lost until problems begin to surface. Here are five questions every executive should be asking before that happens. Experience Capital & Institutional Knowledge | Over 60 Dam, LLC.
By Roger Campbell, Sr. | Over 60 Dam, LLC
10/26/20263 min read


Most organizations know who their experienced employees are. They know how long they've been there, what positions they hold, and what responsibilities they manage. What they don't always know is how much the organization depends on what those employees have learned over the years.
I'm talking about the judgment they use when something goes wrong, the relationships they've developed, and the decisions they make without consulting a procedure manual.
After more than 40 years working in management and operations, I've seen how easily organizations overlook this knowledge. Everything seems to run smoothly until someone retires, changes positions, or unexpectedly becomes unavailable.
That's when the questions begin.
Who knows how this works? Why did we make that decision? Who handled this before? And why didn't we document it?
I believe executives should ask five questions long before those situations arise.
1. Who do we depend on when something happens that isn't covered by our procedures?
Most organizations have procedures for routine activities. The challenge comes when something happens outside the normal process. Often, an experienced employee knows what to do. That person understands history, recognizes the problem, and knows whom to call.
The issue isn't that this employee has valuable knowledge. The issue is whether anyone else has access to it. Executives should identify the people who routinely solve problems others cannot and start understanding how they make those decisions.
2. Which important business relationships depend on one person's experience?
Consider your suppliers, customers, business partners, and other relationships that keep the organization running. Some of those relationships may have been developed over 10, 15, or 20 years.
An experienced employee may understand the history behind an agreement, the personalities involved, or why certain arrangements were made.
A contact list won't replace that understanding.
The question is whether those relationships can continue effectively when the employee who developed them is no longer available.
3. What decisions are being made based on knowledge that has never been documented?
Every organization has employees who make decisions based on years of experience. They recognize patterns, remember previous mistakes, and understand why one approach works better than another.
Much of that thinking never makes it into a written procedure.
When those employees leave, the organization may retain the instructions but lose the reason behind them. Executives should be asking experienced employees to explain not only what they do, but why they do it that way.
4. Could someone else take over tomorrow without calling the person who left?
This is one of the simplest questions an executive can ask, and the answer can be uncomfortable. Organizations often believe they're prepared because they've assigned someone as a backup.
But being named a backup and being able to perform the responsibility independently are two different things.
A practical way to find out is to have the backup employee handle an important activity while the experienced employee observes. You'll quickly discover what the backup knows, what they don't know, and what information hasn't been transferred.
5. How do we decide which knowledge needs to be preserved first?
Not every piece of knowledge matters equally. Some information is easy to replace. Other knowledge may take years to develop and could be costly to lose. Executives should first focus on responsibilities, relationships, and decisions that would be hardest to replace.
Ask what would happen if a particular employee were unavailable for 30 days.
Would operations continue normally? Would customers or suppliers be affected? Would other employees know how to respond? Those answers help establish priorities.
Start Asking Before Someone Announces They're Leaving
One mistake some organizations make is waiting until an experienced employee announces retirement before beginning the knowledge-transfer process.
By then, time is limited. The employee may have years of experience that cannot realistically be transferred in a few weeks. I believe these conversations should be part of normal management practices, regardless of an employee's age or retirement plans.
The goal isn't to replace experienced employees or reduce their importance. It's to recognize the value of what they know and ensure that knowledge continues to benefit the organization.
The best time to identify that knowledge is while the people who hold it are still there to explain it.
Roger Campbell, Sr., founded Over 60 Dam, LLC, where he focuses on Experience Capital, institutional knowledge, and helping organizations recognize and preserve the experience that supports their operations.
