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  • Kwok Cheng Leng

How to Deal with Difficult People

We’ve all had that one classmate or that committee member in a project, who, for various reasons, proved to be a challenging individual to work with. They might have gone MIA (missing in action), or left us wondering whether they were even behind the screen during Zoom meetings. And what about that one unforgettable group member who ended up submitting work completely irrelevant to what was discussed? (I’m definitely not speaking from experience.)

Dealing with such personalities is an inevitable aspect of life. Unless you’ve got plans to assemble a team with clones of yourself, besides simply ranting away in your personal group chats, learning how to better navigate challenging group dynamics might be a worthy skill to master for life.

Types of Difficult People

Before discovering new ways to collaborate with challenging individuals, it is key to understand what types of difficult people you might encounter.

Chris Croft, a leadership and management speaker, identifies three types of difficult people in his LinkedIn Learning course: those who are different from you, those who are incompetent, and those who are toxic.

People Different from You

These individuals might have different characteristics or working styles that clash with your own. For instance, they might prioritize speed in decision-making, but you may prefer to carefully lay out all the options before taking any action. People who are simply different from you won’t get too much in your way; once you recognize these differences, finding and negotiating a common ground might be easier with these sorts of people.

Incompetent Individuals

On the other hand, these people may lack the necessary skills or capabilities for their responsibilities, thus affecting the team’s performance. Compared to the aforementioned group, you might need to invest more effort into changing, training or working with incompetent people. Being patient and allowing them time for improvement may also be necessary.

Toxic Personalities

Last but not least, toxic individuals may be the hardest to handle. They refer to those who exhibit somewhat harmful behaviour, such as being controlling, deceptive, or having a victim mentality. Sometimes, it may just be too time-consuming and tiring to collaborate with them, especially if they also resist change.

Strategies for More Harmonious Teamwork

Well, now that we’re aware of who we may be dealing with, let’s dive into some methods of working with these diverse personalities.

1. Communicating, Understanding, then Seeking Solutions

Understanding the other person will allow you to determine ways to come to a compromise. Regardless of the opposing personality, only when you grasp their perspective can you initiate constructive action or conversation.

For example, consider a key team player that is often quiet during discussions. Often, we might assume that they are shy and need prompting to contribute. A straightforward way we might try to solve this might be to directly call out that teammate during discussions and ask them for input.

While this may yield results for some, it may also backfire and put that team member on the spot. To be frank, I'm guilty of this too, and I have to say that this method of action only makes me feel like a professor in a lecture trying to get students to participate.

What if we take a step back? Perhaps the team member is mostly silent because they find it too hasty to contribute immediately, and prefer taking time to thoroughly mull over the various opinions presented before sharing their own thoughts.

In this scenario, a more effective solution might have been to schedule two separate meetings. The first could be a short 10-minute discussion to throw ideas or share project updates, while the second, set later in the week, could be focused on revisiting these topics in depth. This approach might better encourage your team member’s engagement and allow you to be more inclusive.

As you can see, seeking and understanding the reasons behind a person’s behaviour or action is crucial to finding a root cause, and will promote more effective solutions that accommodate everyone’s needs.

2. Use More “I” Statements and Less Absolutes

Imagine stepping into a meeting, expecting the agenda to be about the upcoming report your group needs to submit. However, you’re caught off guard when your teammates turn to you with a glaring sentence: “You never meet deadlines!”

But wait, you think, that’s not true! Your brain immediately reminds you of the time you completed the literature review and submitted it on time. With that in mind, how would you respond to your peers?

More often than not, people tend to immediately rebut their teammate. When faced with accusatory statements, it's easy for us to jump into defense mode. Our hackles are raised, and we instinctively rush to present our perspective and clear our name. This might easily spiral into a non-constructive argument over who’s right and who’s wrong, and the individuals on the offensive can forget about finding an agreeable solution to address the issue of deadline adherence during that particular meeting.

Next time, if you’re about to broach a potentially difficult topic, consider practising more “I” statements. Starting the conversation with something like “I have been feeling a little frustrated because …” may soften your stance, making you seem less of a sharp knife before confrontation. The person you’re addressing may in turn become more receptive to what you have to say.

Additionally, try to avoid using absolute terms like “never” or “always”. Using words like “sometimes” may dull the edges of your knife even more, reducing your statement’s potential impact on the listener. This might encourage a more nuanced conversation where you can get your point across and enhance the chances of reaching a solution that aligns with both parties' interests.

3. Introduce a Motivating Factor

Occasionally, despite having repetitive conversations with a challenging group member, we may find that little progress has been made. So, why not consider a change in approach? Finding a way to motivate them or make their behaviour affect themselves might just be the trick to encourage change.

A good example would be dealing with individuals who struggle with punctuality. Unfortunately, we can never run from working with people who are constantly late, and though a few minutes of delay is definitely okay, I would prefer not to wait more than half an hour for someone who overslept. After multiple reminders of the schedule have had little effect, maybe you could introduce a system of rewards.

For instance, if you’re the group leader, you could surprise your team with some welfare, like sweets, at the beginning of certain meetings, incentivizing members to be punctual lest they miss out. Alternatively, you could also identify consistent latecomers and set a goal for timely attendance over a designated duration. Then, you can reward them if they maintain a streak, such as treating them to a drink if they’re on time for 2 consecutive weeks.

Of course, this isn't a guaranteed method, but there could be many creative ways you could try to motivate the challenging individual you're dealing with. Special mention to this one example that demonstrates how lateness may affect an employee and thus effectively motivate them to come on time.

4. Change How You Act or Think

I get it, why should we be the ones changing, when they’re the ones at fault?

There are instances where attempting to change someone, particularly if they're long-term partners and 'repeat offenders', might not be worthwhile. Situations where the other party is aware their behaviour is problematic but unwilling to change, or where they might truly embody the saying 'a leopard never changes its spots', are part of various reasons why altering your own approach could be more effective in the long run.

It might also be more practical to adapt your own thinking than spend an excessive amount of time and energy on reforming the individual. However, it's important to assess each situation; do not simply live with the circumstances all the time.

For instance, if a committee member this semester consistently exhibits a victim mentality, they may shirk responsibility by blaming setbacks on everyone and everything but themselves. Changing their mindset might be akin to writing a 100-page essay within an hour, and you might be better off adjusting how you interact with them and holding on until the project ends.

Acknowledge their feelings, but gently nudge them to take responsibility by asking them how they would go about the situation. Have them agree clearly to doing something corrective. You may also lead them to brainstorm solutions within their capabilities, and knowing their character, remind yourself to detach from their negativity and not take anything personally.

Remember, changing your response does not mean you're waving a white flag or compromising your principles. It means finding a balance within your boundaries while maintaining as best a group dynamic as possible.

5. Fun Tip: Get Your Parents Involved

No, I don’t mean having your parents call the ‘culprit’ that’s tipping the scales of a harmonious group.

Especially if your parents have experience in a professional environment, they might have fought a war in office politics once. I can’t express how helpful my mother has been when it comes to giving advice on what to say and suggesting alternative actions during particularly frustrating times with my peers. (Thank you, mum.)

When you’ve exhausted every possible approach you can think of, external perspectives from someone not directly involved could be the enlightenment you need to handle challenging dynamics. Asking your parents or any adults around you may unlock new management strategies and give you a power-up when you next deal with your opposing player.


Human interactions are complicated, but what can we do about it? Beyond what has been discussed, there is an array of other strategies to consider, and there is never a one-size-fits-all solution. Practice makes perfect when collaborating with challenging individuals. Personally, I am still learning and refining the ways I communicate and manage diverse personalities. With time and experience, we can better navigate through the intricacies of human dynamics.

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