Your company has outgrown your best employees. Now what?


If your business has outgrown an employee – it’s never easy. Sadly, unless we are very intentional about growth, the business will outgrow some of the best, long-standing employees.

Outgrown Employee - what to do?

If we’re not intentional, a company will grow faster than an individual.

For some reason, we “hope” that everyone will grow at the same rate. That simply doesn’t happen. Many times the company outgrows an employee or the company grows faster than the employee. It’s tough to let go a long-time employee.

Outgrown Employee? Here’s how to have the difficult conversation.

Conversations about growth with a long-time employee is tough. We call this employee the Team Player. The Team Player has a great attitude, but has lacked in performance recently.

What do to when you've outgrown a long-time employee.

You can see this long-time employee can have a great attitude, but their performance has been lacking.

The Team Player has an infectious attitude. They love the company. They always have the biggest smile at work. They bleed the company colors. They have a can-do attitude and are always ready to help. Through it all, they never wavered in their support. They might even be in charge of the company volleyball team – and have the t-shirt to prove it.

There’s one problem with the team player. The company has outgrown the employee. The company has outgrown their ability to perform in their current role. At one point in the past, you might have called them a Rock Stars Employee.

(Download the free Dando Right Idea, Wrong Person Matrix right now.)

Most of the time, these Team Players simply need a second chance at a new role. You don’t want to fire a long-time employee without a second chance.

You might have an internal struggle. It’s tough when you outgrow your employees. You’ve thought, “There has to be a better person for this role. I can’t get rid of them – look at what they’ve done! They’ve been here forever! I love them!”

The Team Player shows up every day to do the same job. No one tells them anything different (not to their face anyways). In other words, they have done everything you asked of them.

The good news is, with a little clarity and a second chance, these Team Players can get off the bench and become Rock Stars again.


  • Write a job description for this position. Not the person that currently holds this position.
    • Ask yourself, “If this position was wildly successful in 90 days (and one year) from now, what would be accomplished?”
    • What are the Musts Vs. Wants for this position?
    • What about the Skills? Drive? Experience? (Remember here that it is NOT about the person, it’s about the position needed to accelerate growth).
    • Read more about how to write a clear job description.

Once you’ve written the description of the position, it’s time to evaluate if this person can do this role and if they want it. They need both the will and the skill.

If you believe it is possible, it’s time to have the first of many direct conversations. Having this conversation is tough. The key is to provide the employee with all the information they need to be successful and make a decision. They don’t like to be outgrown from their job, either. However, they may excel in this new role, too.

As you prepare for this conversation, remember:

  • Have you given this person every opportunity to gain the needed skills? What classes could they take? Is there anyone who would mentor them?
  • Make the conversation as direct and straight-forward as possible. Instill a sense of urgency.
  • It is important to time-box when you need this position to perform at the level you have defined. If you are in a hyper-growth organization, time and training are likely in short supply.
  • If it becomes clear there is no saving this person in his or her role, take action promptly. It isn’t easy, but delaying the inevitable always makes the situation worse.
  • Is there another role in the organization where they can perform at a Rock Star Level? Investigate this possibility if their current compensation make sense.

Read more to see if you have the wrong person in a key position. Read more about Brilliant Jerks, too.


Do not assume that people and companies grow at the same pace. (Download the free Dando Right Idea, Wrong Person Matrix now).



You may feel a moral dilemma when you realize that the company has outgrown a loyal employee’s ability to perform at a Rock Star level. The employee was more dedicated to growing the business than they were to growing themselves.



Step up as a leader and help your Team Player identify where their talents and experiences can be maximized. This may require a new role or perhaps even helping them find a different company where they can grow. Do not get paralyzed by the reality that growth and success brings.



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