What is the secret to work with people that you simply don’t connect with — those difficult people in your life?

I should learn to work with difficult people? Are you kidding?

I should learn to work with difficult people. Are you kidding?

Difficult people

Yes, difficult people are difficult. You can’t seem to connect. They are argumentative and contrary to what you say. They disrupt your plans and your progress.
You might even think they are out to get you. Their lives revolve around making you miserable. They plot at night how to disrupt your projects.

A quick story

When I was a young professional in a small high tech company one person in particular was labeled as the “difficult person” by his coworkers. Let’s call him Mark. Mark was the root of all mishaps with projects and plans. Mark did throw people “under the bus” in meetings at times. I started to fall prey to this line of thinking about Mark. The “evidence” was clear.

Then, I went on a business trip to visit customers and partners with Mark. Mark and I had the opportunity to talk on the trip. I was highly suspicious. It turns out Mark was very focused on his hopes and dreams of a beautiful home with gardens on Cape Cod in Massachusetts where he could take his seriously ill wife. He wanted to slow down his frantic pace and spend time with his wife, kids and extended family who lives there.

Mark had pinned his hopes on this startup we worked for to achieve those dreams quickly. Mark was frustrated with the slow growth of the company.  Mark let his frustration come through at work. His coworkers, including me, had not taken the time to understand where Mark was coming from.

After the trip I had a much different perspective of Mark and we became more friendly. I understood his perspective. I was able to work effectively with Mark after that trip. I spent less time stressing about things too!

It is more likely that people, even difficult people, will open up when you converse with them and have genuine curiosity about them and their situation.

My wife brings home the wisdom

My wife has a natural curiosity about people and gets them to open up quickly. She knows more about people within minutes than most people know about their coworkers after long periods of time working with them. 

She can tell you what their names are, how many kids they have, the kids ages, where they go to school, what they do for work, where they’ve lived, why they moved and host of other information. She is a natural conversationalist.

In the world of business, learning about other’s personal lives is crucial to understanding them, even difficult people. It is crucial to working with them especially if you find it difficult.

5 must knows to work with difficult people

Be curious about them.  First of all, ask questions and learn about what’s important to them. What the business world deems as important that drive our daily activities may not be aligned with the “difficult” person in your life. Find out what drives them.

Listen carefully. Listen with eyes and ears. Pay attention to body language and what they are saying without words. Are they upset, distracted?

Be open. You never know what distractions or difficulties the other person is going through. Everyone has a story with challenges, hopes, dreams and distractions. Learn what they are before you take on the group judgments.

You might say, “Who cares?” The difficult person should step up.

“Besides, I’m no good at listening and I’m not curious about them, especially Mark!” Okay, fine. Not everyone is curious and a good listener. Except that curiosity, listening, and being open are choices and skills to develop not inherent personality characteristics.

Consider this. If you took a little time to develop communication skills, understand those around you, you may spend less time stressing over situations. Less stress is good.

And, you just might make a ally who can help you during your career. It pays to connect with people in personal ways.


It is wise to remind yourself:    So, remember that people have differing perspectives of the world, different values, and different behavior patterns. Laid on top of those things, people have different situations, struggles, successes, failures, strengths, blind spots and maturity levels. You don’t have to know all their details, just appreciate the differences and get over yourself just a little, especially when it comes to difficult people. 


Understand and accept yourself.  Therefore, every time you get upset with someone else that “did” something “stupid,” your upset state may be pointing at a topic for you to work on personally, one of those nasty triggers. The more you understand and accept yourself the less the difficult people will affect you.

Surround yourself with people you aspire to be like.  And, remember to choose people to work with and socialize with who have characteristics you want.  Do you know what those characteristics are? Even if you can’t choose all the people around you, you can choose more than you think. Choose wisely.

What next?

These 5 must knows will go a long way to helping you work with difficult people.
If you want to talk about strategies of communication, let’s set up a time and talk.
Email me at Phil@PhilBride.com or call me at 503-753-9971.

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