How to Prepare for (and Not Worry) When Your Best Employee Quits

Let's be honest.

If you’re running a business, division, or team, you’ve probably got a star employee that you're worried about losing, or you don't have very good employees.

When you're not feeling impressed by your star employees’ performance, this worry sits in the back of your mind supplying a steady source of business-related nightmares.

Every company I know has at least one such employee. Someone who has the exact skills, talent, and drives your business needs to succeed. They’re your pilot, your Ace, your Top Gun.

Do you have such an employee? Take a moment to picture them in your mind. 

Now imagine them waving goodbye. Maybe just for vacation. Or worse, leaving for good. Picture your business without them. Without their skills, their knowledge, their drive. What would you do? How would you operate?

Without them, you might just nose-dive. You imagine all work grinding to a halt as you frantically try to replace them with someone else. Someone less qualified. Someone less driven. Someone who will never carry the workload your star employee did.

You've procrastinated creating a backup plan for them, haven’t you?

Perhaps you are holding out hope that this scenario will never manifest. Maybe you were too busy today and planning on creating a redundancy plan tomorrow. Maybe you were worried that your star employee would feel like they were being replaced. Or maybe you just didn't know where to start. 

Who's the Top Gun in your company? Can you afford to lose them? 

Who's the Top Gun in your company? Can you afford to lose them? 

Whatever the reason, your business cannot hinge on the output of one, or even a handful of, employees.

But you already knew this... That's why you're worried, after all.

Today, right now, I'm going to show you a drop-dead simple way to begin creating redundancy in your organization. With minimal effort and disruption, this process will be a framework to cross-train your employees, developing their skills and transferring the expertise from your current group of A-players to the next generation. 

Let's start by looking at the benefits.

The Benefits of Cross-Training and Employee Development

Beyond the obvious benefits of retaining employee expertise when someone quits, having a cross-training process can be used to on-board new employees, mentor promising employees, and give your star players a way to practice leadership and prepare for additional responsibilities.

On-boarding New Employees

When it comes to bringing new employees on board, most companies have a process that could be described as ad-hoc, trial-by-fire, or drinking-from-the-firehose. I’ve spoken with some who took pride in such a process, smirking as they thought of how difficult it would be to bring someone aboard.

But you’ll notice each of these processes are described using firefighting analogies. They can, at best, be labeled as dangerous.

With a minimally invasive cross-training program, new employees can hit the ground running in weeks instead of months. Furthermore, existing employees will get some experience leading, an invaluable tool for building a more effective organization.

Preparing a New Generation of Leaders

If you want your organization to grow, you can’t keep your existing organizational structure forever. You need a new generation of employees who think less like individual contributors and more like leaders.

What better way to grow your organization than from within?

Your Ace Pilot will, one day, need to pass the controls to their wingmen. This starts with a cross-training process with an eye towards mentorship.

Mentoring Promising Employees

For every A-player you have on board, you may be able to think of one or two promising wingmen. They may not be as good as the best, but they show the aptitude and have the drive to eventually become so.

These employees must be nurtured. They have every bit of potential your best and brightest have, and with some mentoring could turn into new stars for your organization.

Setting up a cross-training program whereby your critical employees can mentor your promising employees will give your team more firepower on all fronts.

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Notice how all three of these benefits are highly related? This is not a coincidence. Best business practice means eliminating weak points (mediocre performers, single-points of failure) in your organization while simultaneously looking for ways to grow (onboarding, mentoring, and leading).

Now, with these benefits in mind, let’s look at an analogy to help us build a cross-training program for your organization.

Transitioning the Military Way | Left-Seat Right-Seat

Years ago, as our company moved from services oriented work to developing products, I made the move from engineering management to product management. Before leaving my post, we hired a new VP of Engineering and discussed a transition plan to migrate me out, and him in.

For weeks I had been jumbling around a list of things I did, things I knew, things I thought the new guy would need to know when he started. But I had no idea how I was going to transfer it all. It didn't make sense. I couldn't picture it.

My boss at the time was a Lieutenant Colonel in the Army and drew from his experience, mentoring me along the way.

“Mike, you need to left-seat right-seat the new guy,” he said. “Take two weeks. Week one, you’re driving. Week two, he is.”

Of everyone in the world equipped to deal with transitions, I can’t imagine anyone being more efficient than the military. New recruits are constantly rotated into new situations; situations in which current command has immensely valuable experience.

To drop these recruits in cold, ad-hoc, or have them “drink from the firehose” would be both irresponsible and life threatening. A transition plan is not only mandatory but must be straightforward and effective.

And so they are taught to drive and teach (left seat) while the passenger observes. Once the passenger is comfortable with the duties, they move to the driver’s seat. Now the apprentice is at the wheel while the master sits shotgun and observes (right seat).

It's simple, effective, reinforces a culture of leadership, builds mentors, drives learning, and can be repeated as often as necessary with little impact to the mission.

So how do we implement this left-seat right-seat process to get similar results?

Ahem. Driving the Process

Let’s recap our objective here: We’re reducing our business risk of losing a critical employee while increasing the effectiveness of another employee.

With that in mind, let’s continue our analogy by putting your star player in the driver’s seat, and your new or promising employee in the passenger seat. Each person has a role, and each is equally important.

Your Star as the Driver

The driver (your star employee in this case) is in teaching mode while the passenger observes. The driver’s goal here is to continue to perform the work he or she performs on a daily basis while providing instruction to the passenger so they can eventually drive themselves.

Some key things your driver needs to do in this position:

1)      Create a list of projects they are working on, tools they use, and meetings they attend for their passenger.

2)      Invite the passenger to their meetings.

3)      Schedule new meetings where the driver can review the projects and tools on which they are working.

This process can take as long as you need it to, but I wouldn’t recommend letting it go on for more than a week. After all, the passenger will need a chance to drive.

Your Star as the Passenger

For the second part of this, your star employee moves to the passenger seat. Their role there is just as important as it was while driving. Instead of taking the lead, however, they observe and teach.

Now the driver, the apprentice, is looking to become the master. They are doing their best to take what they learned in the passenger seat and implement it themselves.

Of course, they aren’t going to get it right. So the star, the passenger, helps keep your apprentice on track by making adjustments and providing guidance along the way.

Implementing Your Backup Plan

Before you can make any headway with this process, you’re going to need buy-in.

Bring your star employee in for a one-on-one meeting, telling them your plan for transitioning some knowledge to others. Your star employee may have concerns about being replaced, and you should address this head-on. For example:

“You are our best and brightest employee, and it is not my intention to replace you. I need to keep work going when you take a vacation. I want you to get some experience leading. I need others to learn what you know so they can be more productive, and I want you to be able to delegate some of your tasks so you can accomplish even more through others.”

Once they are on board, have them draw up a spreadsheet and categorize all their responsibilities, meetings, projects, tasks, etc. This will be their guide for the next two weeks, and this will be the first thing you share with “the passenger.”

What is your role when this plan is in progress? Oversight. You’re watching from afar, ensuring the car is driving the right direction, ensuring your driver and your passenger are communicating, ensuring they switch seats half-way through. Check in with them every two days, look at their spreadsheet to gauge progress, and help them eliminate any obstacles along the way.

When all is said and done, hold a short retrospective meeting with them to hear how things went, what could be done differently next time, and what still needs to be learned.

And that’s it!

Run this exercise a few times and you will not only reduce the risk of your star employees quitting, but you will also see their productivity increase as more of your employees enhance their knowledge and level of participation in the organization.

Your best employees will be able to offload more complex work to their team, and you’ll have the beginnings of a new generation of leaders on hand for future growth.

What improvements would you make to this process? What kinds of cross-training or employee development programs have you implemented in your organization to reduce the risk of losing your star players? Let us know in the comments below.

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