Finding Value in Working With Difficult People


The Value of Difficult People

It's likely we all know someone we'd describe as "difficult" to work with. Maybe this someone is your co-worker, or your client, your friend, and so often, this person is your boss.

Today, I want you to get that person (or people) in mind, because we're going to talk about them. And I'm going to talk about the value that they give us - even if we never find a way to move past our differences.

I'm sharing my thoughts on this in a first-ever video story below.

Nothing super fancy - just me and an iPhone for this, but this is a tough subject - so I felt it was the perfect one to tell you directly my perspective and advice on it.


The Lowdown

Even if you're not able to watch the video just yet, here are some complementary thoughts on the subject.


Whether or not you find someone difficult to work with, they still have tremendous value to you - past, present, and future.

Here's a few examples of what kind of value someone like this can often bring you:

  • Give you a job (or hire you)

  • Provide opportunities and experience (even if it feels like going to hell and back to get it!)

  • Introduce you to new ideas and concepts

  • Teach you new ways of doing things

  • Connect you to new people, who could provide valuable advice, opportunities, and more

  • Share good or not-so-terrible times (even though they may be few and far between)

  • Push you to get outside your comfort zone

  • Shape how you treat others (reminding you to be more empathetic) and improving those relationships as a result

  • Help you to further define who you are (and who you aren't)


Remember whoever you're dealing with is a person of value, and you may be in their life or in their career at a difficult time.

The people we struggle with do still have value (and can provide it, as I shared above). Not only that, they can often be talented, kind at times, great at times, etc. The thing to remember is that each person is a whole person- not just their job or how they are being when it comes to hiring or working with you.

Sometimes you get started on the wrong foot. Sometimes you're dealing with someone who's facing massive insecurities or intense personal problems. Though that doesn't ease your feelings after an impossible day - it can help you to see that at the very least - it's not necessarily you.


Do you know your communication style, and do you know theirs?

Early on in my career, I definitely began to realize that my extrovert, expressive communication style wasn't an ideal match for everyone. I would come up against frustration and misunderstanding with managers, coworkers, and others because we literally weren't compatible from a communication perspective. I finally figured this out after doing a training on the subject at Disney.

In that class, I learned that there are essentially four overarching communication styles that people use. 

These are:

  • Analytical

  • Intuitive

  • Functional

  • Personal


I'm pretty predominantly a "Personal" style. So Mark Murphy for Forbes would tell me "as a Personal communicator, you value emotional language and connection, and use that as your mode of discovering what others are really thinking. You find value in assessing not just how people think, but how they feel."

Can you imagine how tough it was for me when I'd deal with an Analytical style person? No wonder I'd get blank stares and poor feedback when I leaned way into my own style. I needed to bend more to theirs for more effective communication on projects and even just daily interaction.

Want to figure out what style you are (and what your difficult person's might be?) Check out this free quiz and profile at Forbes.

Forbes Communication Styles + Assessment


Try an outside-the-box solution.

As I reference in the video, it took a creative solution (proposing a completely different position/workflow than I was assigned) to transform a difficult relationship into a powerfully positive one.

Knowing what it's like to be living these situations in daily corporate life, I'm sure you may feel as though you've tried everything. That's solely why I say - think outside-the-box. Is there a radical, creative idea you could give a shot? If you've had one-on-ones at the office that have gone nowhere, how about a change in venue? Like, what if you asked your boss to go bowling? Maybe being outside your comfort zones together could lead to a more productive way forward.

If you can't seem to see eye-to-eye on a project, maybe you can schedule a half hour to put it on hold and brainstorm solutions together.

If you've got a client that doesn't seem to understand your emails, how about hosting a Google hangout to chat through and answer any questions that are coming up?

You get the idea - just about when you're ready to hit your head at the wall - give it one last outside-the-box go.


It's not "don't give up," it's "leave the door open."

Look, as I share in the video, there will definitely people you encounter that you can't make it work with - no matter how much you bend your style, get creative, or reframe the situation.

However, keep in mind a couple of things -

When you leave the door open, life can surprise you. I found a friendship and a fierce advocate in someone who I thought I didn't believe in me. I kept trying and that story - the good, the bad, and all the inbetween, has given me tremendous hope for those I meet in the future. It also taught me that sometimes it's not about you or the other person - it can be about the situation you're in or the place in life you're finding yourselves in.

People you don't fit with now can have a way of coming back into your life. I became friends with one of my challenging bosses years after the fact. What clinched it? The person told me they thought I did a fantastic job. It took two years to find out they felt that way and it made a big difference in our relationship and friendship from that point forward. Of course, it also helped that we were friends and not working together anymore - but nonetheless - I found value I never expected to - it just took time.

Even if you never break through, you've gotten value from the relationship and it likely made you a better person. As I said at the beginning- this value might be that a negative working relationship (or negative relationship in general) shapes you into a more caring, flexible person. Pivoting who you are, learning from relationships, makes you better at future ones. You may not see it now and may truly be in the thick of it, but I can tell you looking back - even to recent challenges - I've learned something valuable to my personal and professional life from every single person that I found difficult to connect with.

I'll leave you on one last thing. If you're a fan of Daredevil (streaming on Netflix), there was a recent episode (Episode 4 "Penny and Dime") that features the funeral of a deceased mobster named Grotto.

The priest gives Grotto's eulogy and he says that though he was not a good man, and he did terrible things - each of us - all of us is a world unto ourselves. We are each a series of connections, memories, stories - if you'll let me go there.

So that just to say - no matter the people we encounter, we are each a world.

Today's post is about encouraging you to seek more ways to connect with someone else's world, and to realize yours is better for having been a part of it - no matter how difficult the path (or the person) may be.

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