Leading Challenging Employees

Greg Sweeney
2 min readApr 28, 2021

The challenge with leading challenging employees

We’ve all had challenging employees where the relationship was not as smooth as we would like.

And while these situations are challenging in normal circumstances, with a virtual workforce, the difficulty increases.

A challenging employee is someone who acts in a disruptive, unprofessional or irresponsible manner.

They challenge authority, create a negative or disruptive work environment, and struggle to meet performance expectations.

With challenging employee you have a choice

Working with challenging employees is challenging.

But as leaders we have choice. We can decide to invest in the employee; or cut our losses.

When deciding, it’s important to understand that sometimes, challenging employees are not being difficult on purpose.

It could be that they are simply dealing poorly with difficulties in their personal lives.

Here are three suggested responses.

Presume challenging employees are competent.

Always presume your employees have the knowledge, skills, and abilities to succeed.

If they don’t, then presume they have the desire to acquire them.

Challenging employees require EQ

Challenging employees require leaders exercise emotional intelligence. EI helps us discern what the employee is thinking and feeling.

But in a virtual environment, we are “sensory handicapped”. We lack the other senses and are dependent mostly on our ability to listen.

So it’s important to be mindful and present.

Tap into your emotional intelligence to pick up on the verbal cues (choice of words, tonality, pace, etc.). Be inquisitive about their needs and practice empathy.

Persistently reinforce desired behavior

Stay alert during engagements.

Look for opportunities where you can positively reinforce desired behavior.

If you are persistent then chances are you will be pleasantly surprised by the results.

When you presume competence, engage your emotional intelligence, and are persistent with positive reinforcement, you can improve any working relationship and fundamentally alter the course of your employee’s career.

Leading challenging employees requires empathy and patience and is a true test of leadership skill.

Are you up for the challenge?

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Greg Sweeney

After 20 years in the industry, I'm fascinated by the technology, talent, and cultural transformations taking place impacting cyber leaders and the workforce.