How to deal with difficult people

Matthew Oldham
The Startup
Published in
5 min readMar 14, 2019

We all face them, eventually. Maybe it’s a boss, a coworker, a customer, or even a relative. They’re just difficult people. Thorny, short-tempered, moody, negative…pick your adjective.

I know I face them. In my capacity as a software engineer for a startup company, I get to interact with all sorts of personalities and meet people across the nation in a broad range of roles such as analysts, programmers, physicians, hospital administrators, and c-level executives. What a privilege it is to meet so many amazing people — even though mostly in a virtual capacity — and to get a tiny glimpse into such an incredible variety of environments. Most of these fine folks are very easy to work with, but there is certainly the occasional prickly pear.

I’ve found that most of the challenging individuals I meet are simply products of these respective environments, and have consequently adapted to their toxic cultures by building defense mechanisms to protect them in the face of challenge, criticism, or attack.

It should come as no surprise, then, that the real hurdle to get over with such people is trust. Their trust has been compromised in the past, and therefore it’s no longer freely dispensed to newcomers. It makes sense when you think about it.

How do we break through this barrier?

The avenue through which trust is usually formed is relationship. The challenge in a normal business setting is that there is sometimes very little time or opportunity to build relationship. Digging deeper, what is it about relationship that allows trust to develop? I believe it’s the simple repetition of one person observing how another person behaves and responds. When a person’s positive behavior becomes somewhat consistent and predictable, there is less of a perceived risk in extending trust to that person.

Said another way, we must show ourselves trustworthy. But how?

Honor the person.

In a prior article I wrote about this fundamental principle. Honor is one thing that you can and should show every single person with whom you come in contact. The simple reason for this is that every person has inherent value because they are human beings. Their value, therefore, lies in their personhood, not in their behavior. When facing a difficult personality, there are several ways to show honor.

The easiest among these is listening. Listen intently to the things they say and be prepared to respond thoughtfully. A thoughtful response will demonstrate that you’re not just tolerating them while you wait for your turn to speak.

When you do respond, do so respectfully. Showing respect to the individual is a form of honor whereby you consider that they have a unique perspective and contribute valuable history and experience to both the conversion and relationship. Their experience is unique and deserves due deference.

Lastly, exercise what I call the mercy/humility rule. Whey they are wrong about any particular matter, show them mercy. When you are wrong, show humility. The point is that you make room for both their mistakes and your mistakes. Enter every interaction with the keen awareness that both parties have a limited perspective.

Be real.

Fake is noisy, and fake is really obvious to people who have been burned in the past. When you’ve already chosen to honor a person, regardless who he or she may be, it becomes much easier to be yourself. Get rid of pretense and airs, and just be a real person. Genuineness is what people are looking for, after all, so there’s really nothing to be gained by manufacturing a persona.

Don’t expect reciprocation here, by the way. That protective mechanism in the other person will likely be in full effect, and one of the manifestations of it can be pretense. Don’t let it throw you off. Determine to be yourself, regardless.

Challenge them.

Really? Yes! Here’s what I mean. Often a difficult person will be armed with oppositional ammo when they enter a conversation. This can range from negativity and apathy to counter-arguments (valid or not) to all your points.

To challenge them is to ask them questions and make them backup their claims or produce evidence. Not in a disrespectful or provocative manner, but in a fair and respectful way. I learned this method by watching others achieve success in difficult conversations.

They would say things like:

  • I’d love to see what you’re describing. Would you be willing to share some examples?
  • I’d love to learn more about what caused that to happen. When can we schedule more time to discuss this?
  • Could you put me in touch with someone on your team who can perhaps share more details on what actually happened?
  • Would you be willing to document that in an email so I can research it further?
  • If that’s happening, we need to get it resolved. What steps would you like to see us take next?
  • I’d love to work through this with you and make things better.

Responses like these demonstrate that you’re taking them seriously. It doesn’t mean that you’re acknowledging all their claims and arguments are valid. Rather, it shows that you’re willing to listen and invest the time necessary to address their concerns. Sure, this may be committing you to more time with the difficult person, but this is how you break through. Small, consistent investments in the relationship that add up over time.

Do what you say.

My very first job in the IT industry was with a manufacturing company that had, as one it’s core values, the statement, “Say what we do, and do what we say.” The intent of this statement was the core principle of integrity. You live this principle out by following up, responding, and delivering on the things you committed to deliver in a timely manner. This shows them that you’re serious.

Building trust is about showing yourself reliable. Be proactive in reaching out to continue the conversation. It’s one thing to survive a single interaction with a difficult person, but it’s another thing altogether to take the first step in re-engaging with that person and being willing to face them as many times as necessary. Do the hard things.

Conclusion

There’s no avoiding difficult people in life. Remember that the road to building trust with someone can feel long, and you may never reach the destination. But, I believe that sticking to these practices is the shortest path to success where success is achievable. Practicing these things consistently will also help you level up your people skills, regardless of the personalities you face.

This story is published in The Startup, Medium’s largest entrepreneurship publication followed by +434,678 people.

Subscribe to receive our top stories here.

--

--

Matthew Oldham
The Startup

Passionate about data and technology and using both to solve problems in unique and innovative ways | Lover of good writing | VP Engineering at Graphium Health