Dealing With Difficult People In Difficult Situations As A Leader

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Dealing With Difficult People In Difficult Situations As A Leader

4 Things Leaders Need To Know About Dealing With Difficult People

  1. Open your ears and listen.
  2. Try to understand where they’re coming from.
  3. Friction isn’t always a bad thing.
  4. Setting boundaries helps move toward a solution to a difficult situation.

I was recently speaking with my business partner about how leaders tend to use “safe guard” words when conversing with people, especially if they are annoying or difficult.

Because we don’t really want to hear what they have to say, we pretty much “nod our heads and agree” or “just smile and say yes,” even though we aren't truly paying attention.


We think that by doing this we’re saving time and/or stress, but that soon comes back to bite us in the butt when another, similar situation crops up.

Here are four things you need to know as a leader dealing with difficult people.

1. Open Your Ears When Dealing With Difficult People

The thing with difficult people in difficult situations is that sometimes they just want someone to hear them out, sincerely. When we choose to tune them out, it’s like fueling their fire.

As leaders, we need to learn to attentively listen to the core issues of difficult people in difficult situations.


Next time you’re in a difficult situation with a difficult person follow this advice:

  • Be still.

  • Listen.

  • Understand.

Which brings me to my next point: Understanding.

2. Good Leaders Try To Understand Difficult People

This goes hand in hand with listening, because you can’t understand without first actively listening.

Anytime I find myself in a tough conversation or a heated debate, I try to take a step back and truly hear the person talking.

I try to feel what they’re feeling and sense what they’re sensing.

I do this because everyone has a purpose for what they do – especially when they’re being “difficult.”

Something triggered them to act in a certain way – whether they realize it or not – so I try to understand that.

This allows me to be a part of the solution and not a contributor to the problem.

Disclaimer: Understanding is much different than kissing someone’s butt as a technique to get them to stop being difficult. It’s also much different than letting people walk all over you.

If you truly value integrity and character, you’ll take the time to put yourself in someone else’s shoes in an attempt to see their point of view.

3. Friction Is NOT A Bad Thing

There are times that it’s okay to agree to disagree.


Just because you choose to understand someone doesn’t mean you have to agree with them just to get them to go away.

Don't be silent. You need to be clear on your stance in whatever the situation is and voice it effectively, in an understanding way.

When we’re in difficult situations, we often think “Why waste my time saying anything to this person?”

If you stay silent, though, you can often give the impression that you agree, or don’t have a problem with what they are saying.

An easy way to understand someone without having to agree with them is to keep the situation factual.

When you’re dealing with difficult people, little things are often blown up or exaggerated into big focal points.

It’s very similar to a heated argument in a marriage when the spouses use words like, “Never…Always…Nothing…Everything…Worst…etc.”

They throw around generalizations like it’s their job, just because they want to prove a point.

This can destroy productivity and effective communication. If you are dealing with difficult people, whether it’s a client or a co-worker, remain in line with facts, not feelings.

4. Moving Towards A Solution With Boundaries

There may come a point in time at which you have to draw a line in the sand with difficult people.

We have a saying at Flight Media: “No client – or anybody, for that matter – is worth constant stress.”

This is where boundaries need to be put into place that will protect you from unwanted stress.

The boundaries you set may be that you don’t work together with certain coworkers on projects, or you find a different person to report issues to. If it’s a client, you may have to cut them off.

You need to make decisions that ultimately better yourself in your business, especially as a leader.

The boundaries you set are not to make yourself “better” than others or to have a false sense of pride.

They’re for the protection for your overall well-being, which in turn affects your business.


Boundaries allow you to move towards solutions much faster – which should be your overall goal.

Final Thoughts

Often, we’re so quick to get rid of difficult situations that we forget to solve them.

If you have the opportunity to solve a difficult situation or mend a relationship with a difficult person, do so. The majority of the time, a solution is better than cutting things off, or withdrawing yourself completely.

Remember that – in our roles as entrepreneurs and certainly as leaders – we solve customer pain points for a living and turn those solutions into business.

Why not do the same with difficult people and situations?

The next time you’re in a difficult situation, make a conscious decision to take steps to an overall solution.   

Take a moment and think of one situation in which you wish you would’ve put yourself in a difficult person’s shoes. How could the outcome have been different?


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Josh Coffy

Josh has an exhaustive understanding of technology and a creative marketing approach that drives client results. In his free time, Josh does CrossFit and travels with his wife.