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How to Have That "Tough Conversation" with a Problematic Employee

Updated: Apr 16, 2019

If you're a manager who feels that they spend 80% of their time dealing with 20% of their team members then you’re not alone!

We’ve all been there.

A time in every leader, manager or supervisor’s life when all you thought you knew about leading and managing people goes out of the window...

You’re faced with the employee who, for all intents and purposes, appears to be unmanageable.

This is the individual who...

  • doesn’t want to do as they are asked, or who

  • agrees to do as they’re asked but fails to deliver, or who, more astonishingly,

  • presents an alternate version of what was agreed to and tries to pass it off as perfectly acceptable.

Those who think management is easy have evidently never had this employee assigned to them!

But before we go on let’s dispel a myth now...

None of these employee examples we’ve spoke about is truly unmanageable.

In my twenty-five years of managing teams and developing other managers I have met very few employees who are unrepentantly unmanageable.

In fact, thinking of these individuals in such a manner is unfairly demonizing them – and unfairly positioning yourself as a victim or martyr.

It’s unlikely (though not impossible) that you have an employee who is intentionally refusing to deliver, failing to deliver of changing the rules of the game for the sole purpose of making your life miserable.

If that is the case then what you actually have is not an “unmanageable” employee but a sociopathic one...

If you suspect that this is what you’re dealing with then I’ll refer you to The Sociopath Next Door, by clinical psychologist and former Harvard faculty member Martha Stout, PhD.

For the rest of us, a much more valuable perspective is to separate the behaviour of our “unmanageable employees” from them as individuals.

Viewing your employees as well-intentioned colleagues who are trapped in a cycle of exhibiting a behaviours or group of behaviours that need to be addressed sets you up for success because:

  1. it builds empathy: once you view them as colleagues who need assistance you can reframe yourself someone in a position to help

  2. you can build a list of actual problems to address to

  3. can enroll your employees as partners in instituting behavioral change

  4. you can cooperate in building an action plan that sets them up for success.

This simple paradigm shift is essential to move forward into a positive working relationship with this manager-employee relationship.

Let’s look at the situation from their perspective for a moment...

Consider if you or other managers have actually pointed out to the employee that their behavior is unacceptable. More often than not, when poor behaviour is tolerated for any period of time, it becomes the norm.

Indeed, it may be that the organizational culture that surrounds this employee encourages the problem behaviour and that, from the employee’s perspective, “everyone is doing it”.

Consider if you or another manager have explained the consequences of the poor behaviour. It’s possible that the employee knows that they are missing deadlines or producing sloppy work, but in their mind it may not be an issue...

They may feel that the work is still getting done, or no one is looking at it anyway, or it affects only themselves.

In the case of an employee who is perpetually late...

For example, they may not be aware that the earlier shift cannot leave until they arrive and as a result another employee is consistently late to pick up her child from daycare which has financial repercussions.

Consider if the employee has been managed properly in the past. They may have been allowed far more slack in their previous position because their previous manager had different standards, was ineffectual or simply was too frightened to have the difficult conversation that you now find yourself faced with.

What choices lie before you in terms of dealing with this Unmanageable employee?