Category: Communication Skills

I once had a difficult boss. Let’s call him Bernie. Bernie was one of several people I was reporting to, but his requests took, by far, the most of my attention. Hi there! My name is Nik, and whether you have a tricky boss, annoying customers, or that one friend you keep bumping heads with, today, I’d like to show you 3 tangible ways on how to deal with difficult people.

Going back to Bernie, the main reason I had to work more for him than anyone else was that his to-dos always came at the last second. “Hey boy, I need you to drive this car down to the dealership!” …and there went my Tuesday morning. He’d also give me tasks without instructions, expect me to know processes I wasn’t yet familiar with, and could get impatient quickly. By the end of my internship, I basically managed his entire workload while he mostly goofed off and left early.

It’s not that Bernie was a bad guy. He was just unorganized and, let’s be honest, a bit lazy. Bernie had been in the company for almost 20 years, and with that, well, certain habits set in. But he was also very funny and taught me a lot about life — in a corporation and in general.

During my first few weeks at the company, I was shellshocked by some of Bernie’s behavior. Over time, however, I learned to deal with him more productively. I made sure I always had some white space on my calendar for his spontaneous errands. I also built rapport with him by a.) doing good work and b.) mirroring his jovial nature.

By the time my internship ended, Bernie and I were on really good terms. I had the courage to push back on what I felt was unreasonable. I asked for more time when I needed it, and we constantly traded jokes back and forth. Often, the humor would help me deliver my requests and make it easier for him to accept them.

Have you ever had a boss like Bernie? Regardless, I’m sure you too meet people in your life that are difficult to deal with. Today, I’d like to share 3 tips with you that’ll help smooth out the relationships in which you just don’t vibe as naturally as in others. Here they are:

1. Never say “never,” and always start with “I.”
2. Set boundaries that are neither too porous nor too rigid.
3. Remember “the 7 Cs” in difficult discussions.

By the way, I found these tips in a collection on Blinkist called Dealing With Difficult People.* Blinkist is a professional book summary service with over 5,500 titles in audio and text, shortcasts, a super polished app, and a lot more. You can read our full review of the app here.

Collections are one of Blinkist’s newer features. Rather than just condense the best ideas from one book, the Blinkist team hand-curates several of the best titles to help you with a specific issue. In this case, it’s dealing with difficult people. Even if you don’t use every tip from every summary, after browsing the collection, you’ll have several new approaches you can try with fussy coworkers and co.!

So, here goes the first tip.

1. Never Say “Never,” and Always Start With “I”

In Powerful Phrases for Dealing With Difficult People*, Renée Evenson shares over 325 ready-to-use lines and phrases which you can use to disarm, connect, and cooperate with others. Her two most basic rules? Never say never, and always start with “I.”

“You never clean your plate after you’re done eating!”

How does it feel to read this sentence? Not great, right? Even though you know it’s not directed at you! Imagine it were. How much would it make you want to clean your plate? Not at all, right? If anything, it’d make you want to fight back! Now, consider this:

“Hey, I did the dishes today, just wondering, was that your plate in the sink?”

Totally different, right? Now, instead of a big accusation, we have a small conversation. It’s a lot easier to say, “Oh yeah, that was mine, my bad, I’ll clean it next time!” after an opener like this, isn’t it?

So: When dealing with difficult people, avoid phrases like “never” and “always,” and lead with “I” instead of “you.” Rather than making something look like a permanent issue from the get-go and blaming it on the other person, consider it as a one-time event and start with your perspective.

If you want more powerful phrases like this, I suggest you browse the Dealing With Difficult People Collection on Blinkist.* If you sign up for a free account* and start a free trial, you can listen to the full summary of Renée’s book, and a lot more!

2. Set Boundaries That Are Neither Too Porous Nor Too Rigid

In Set Boundaries, Find Peace*, Nedra Glover Tawwab offers practical tips on making sure others know where your limits are. A key insight? Boundaries must be neither too flimsy nor too stiff in order to do their duty.

When our boundaries are too weak, we end up absorbing other people’s emotions and problems at the expense of our own. If you constantly adjust to others’ demands, you’ll quickly feel miserable and unappreciated. You’ll become a people-pleaser and end up in codependent relationships, where neither of you is happy (you because you’re just catering to someone else all the time, and they because they feel like they can’t solve their own problems).

When our boundaries are too strong, however, we might isolate ourselves and struggle with our emotions all on our own, which is equally dangerous. If you never share, you’ll never connect with people. Chances are, you’ll even feel threatened when they do and abandon them right before you really get close with one another. You’ll become a loner who avoids people, and you’ll resent yourself for it.

So, not too porous, not too rigid! The golden balance rests in the middle. Make sure people know they can’t poo-poo all over your needs and plans, but stay open to helping others when they really need you and being as vulnerable with them as they are with you.

Want more people-wisdom like this one? Check out the Dealing With Difficult People Collection on Blinkist.* Sign up for free and/or start a trial, and begin listening (or reading) right away.

3. Remember the 7 Cs in Difficult Discussions

In Can We Talk?* Roberta Chinsky Matuson shares 7 principles to help you navigate difficult conversations at work and in life.

What are they?

1. Confidence
2. Clarity
3. Compassion
4. Curiosity
5. Compromise
6. Credibility
7. Courage

In my relationship with Bernie, I first built credibility via executing his tasks as best as I could. That gave me the courage to push back and the confidence to ask for what I needed to help him without crossing my own boundaries. I had to make clear demands while also showing compassion for his needs. “I’ll drive the car to the lot, but is it okay if I do it by 3 PM instead of right now?” These 5 Cs allowed us to compromise productively, and they also made room for me to stay curious about Bernie as a person and learn from him where I could.

So, when you’re in a tough spot, remember the 7 Cs. Focusing on even just one of them can get you through a difficult conversation with a much better outcome than you had anticipated!

If you want to explore Can We Talk?* and more books that help you handle difficult folks, take a look at Dealing With Difficult People on Blinkist.* There are a lot more great titles to discover on this topic! Here’s a sneak peek:

How To Deal With Difficult People: 3 Tips in a Nutshell

No matter how friendly we are, there’ll always be people in life with whom we don’t hit it off as much as with others. That’s okay. We don’t have to be friends with everyone, but we can get along with almost anyone — at least insofar as we need to — especially if we follow a few simple practices to make our shallower relationships more efficient.

I hope you learned a thing or two from my story about Bernie, and if you’re dealing with a demanding someone, keep in mind today’s 3 takeaways:

1. Never say “never,” and always start with “I.”
2. Set boundaries that are neither too porous nor too rigid.
3. Remember “the 7 Cs” in difficult discussions.

For more lessons on navigating the maze that is human relationships, check out Dealing With Difficult People on Blinkist.* It’s a treasure trove full of tips for handling exhausting bosses, delicate coworkers, and “special” friends. I hope you’ll take a look.

May your boss go easy on you today, and I’ll see you soon! 👋🏻

PS: Blinkist also has plenty of other collections. Want to master your body language in 6 days? Align with your Enneagram Type? Upgrade your social skills? Collections has you covered. Browse some of the best ones here* »