Working with a difficult person? Here's how to handle it

Hi {{first name | friend}}

I know you’ve got a difficult coworker. We’ve all got one.

You probably have a specific person in mind right now. (I know have!)

This week, I explain exactly why you clash with certain people at work, and what to do about it. It might surprise you because you play a bigger role in it than you think.

Here’s what we’ll cover:

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When we think of a difficult person at work, we picture someone who’s impatient, controlling, overly detailed, inflexible, full of worry, someone who rarely takes responsibility, someone who drains every drop of your energy.

It’s easy to assume that you’re not one of them, but it’s important to know that anyone can become a difficult person to work with. Even you. Even me, and I teach human skills.

If you’ve studied psychology, you’ll have heard of The Big Five personality model, which describes personality through five traits: openness, conscientiousness, extroversion, agreeableness, and neuroticism. It’s a useful model to understand the different personalities we come across in the workplace and how we can best collaborate with them.

Knowing where you sit on the spectrum of each trait helps you understand why you find some people and situations easy and others difficult.

When I came across this framework and started using it at work, my experience at work became so much easier and I found people to be less draining. And, of course, I want this for you too.

Think of each trait as an approach to work. Most people think difficult coworkers are just difficult people. But they're not. They're people whose approaches to work clash with yours. Once you can see those clashes clearly, you can stop them.

I’m going to walk you through each trait now.

As you read through them, I’d like you to think of two people:

Openness is how you approach ideas. Are you curious and innovative, or cautious and avoid change?  

People high in openness enjoy exploring new ideas and embracing the unknown. They can become difficult to work with when forced into routine or rigid processes.

People low in openness prefer predictability, structure, and familiar ways of doing things. They can struggle when faced with constant change or uncertainty.

You can see how someone high in openness and someone low in openness would struggle to work together, can’t you?

Think about you and your difficult person:  

If you’re high in openness, tell people about your love for new experiences and challenges. Position yourself to lead on the changing parts of your work. 

If you’re low in openness, tell people that you do your best work in familiar environments and prefer change that’s introduced gradually. Position yourself for tasks that need to be done in the same way every single time. 

Conscientiousness is how you approach planning. Are you methodical and organised, or flexible and spontaneous?  

People high in conscientiousness love structure, lists, and clear plans. They’re highly detail oriented. They can become difficult to work with when things feel chaotic or unplanned. Even sending someone a meeting invite that starts in the next 30 minutes could throw them off because they weren’t expecting to do that today. 

People low in conscientiousness prefer to stay flexible, focus on big ideas, and avoid getting bogged down in detail. They’re likely to be big-picture thinkers and they can become difficult when overloaded with structure and deadlines.

A few years ago, I had a manager I struggled to work with. She was high in conscientiousness. Structure, clear plans, GANNT charts, detailed instructions were important to her. I’m more mid-conscientiousness. I can follow a plan and do what’s asked of me, but if something goes wrong, I have the flexibility to adjust and move in a different direction. That’s why we clashed.

To give you some context… The longest email of instructions I received was 1,800 words for a 30-minute task. The longest meeting without a break was 4.5 hours. You get the idea.

I found her incredibly difficult to work with and she thought the same of me. We were constantly challenging each other’s approach to planning and detail. 

Think about you and your difficult person:  

If you’re high in conscientiousness, tell people you thrive with structure and practice patience when others take a looser approach.  

If you’re low in conscientiousness, tell people you work best with flexibility and be open to meeting others halfway when structure is needed.  

You can’t just tell people I need structure and detail and not expect to meet them halfway. This is all about how to communicate your needs to the other person and adapt to each other.

Extroversion is how you approach social settings. Are you outgoing and energised by others, or reserved and reflective?  

People high in extroversion love social interaction. Think teamwork, collaboration, spontaneous chats, open workspaces. They can become difficult when they feel disconnected from people.

People low in extroversion prefer quiet work, focussed time, one-on-one conversations, and if there’s social interaction it’s best they know about it in advance. They can become difficult when overstimulated by people. 

Think about you and your difficult person:  

If you’re high in extroversion, carry on seeking out connection with others, but remember that not everyone likes social interaction as much as you do. If someone isn’t responding to your level of extroversion, it’s not personal. 

If you’re low in extroversion, keep protecting your energy, prioritise one-on-one conversations, but recognise that for some people social connection looks more full on than you’d like.

Agreeableness is how you approach teamwork. Are you cooperative and pleasing, or more analytical and direct?  

People high in agreeableness are team players. They’re helpful, and quick to say “yes”. Highly agreeable people become difficult when they take on too much and end up letting people down.

People low in agreeableness are logical thinkers, they question everything, they think independently (we love an independent thinker). They can become difficult when their need for thinking and questioning is dismissed.

I used to work in a team with people who were on opposite ends of agreeableness. One of them would challenge everything, and the other would say yes to everything. The person who constantly challenged anything that came their way was perceived as difficult to work with because she was seen to “pick holes” in everyone’s ideas. The person who constantly rolled over was perceived as difficult because they were overworked and overwhelmed from trying to please everyone. 

Think about you and your difficult person:  

If you’re high in agreeableness, know that people value you for your helpfulness, but don’t forget that boundaries exist.

If you’re low in agreeableness, remind yourself to be aware of how you’re questioning things so that you don’t come across as nitpicking or being a Debbie downer. It’s helpful to tell people why you’re questioning something.

Neuroticism is how you approach worry. Are you sensitive and cautious, or steady and emotionally resilient?  

People high in neuroticism are often deep thinkers and highly aware of risk. They can become difficult when they’re afraid because they’re thinking, “What will go wrong?”  

People low in neuroticism are calm and tend to take things as they come. They can become difficult when they don’t understand why someone is worried. 

I have a story about this one…

My mum and I went to Copenhagen for a weekend. On our last day, we took the metro to the beach. I was getting our tickets at the machine, putting my pin in as the train was pulling into the station.  

Mum said, “Hayley, it’s about to charge you £70.” She went to pull my card out of the machine. 

I looked at her, “Mum, the ticket price is in Danish Kroner.” 

I selected the tickets again, and just as the machine spat them out, the train left. We spent 15 minutes stood on the platform waiting for the next one.

My mum is highly neurotic. She worries about what could go wrong, she’s always on the lookout for the next catastrophe to try to prevent it from happening. (Mum’s, I guess!)

Meanwhile, I don’t understand the need for worry because nothing’s happened yet.

My mum unintentionally causes worry, and I unintentionally overlook her need for reassurance.

Think about you and your difficult person:  

If you’re high in neuroticism, know what calms you and don’t be afraid to ask people for clarity or reassurance when you need it.

If you’re low in neuroticism, stay grounded (you make a great leader in a crisis moment), but remember that other people may need more space to prepare for uncertainty than you do.

Go through the five traits and rate yourself and your difficult person as high or low.

Identify where you clash with your difficult person and think of what you need to communicate to them or where you can adapt to make things easier for you both at work.

You’ll know by now that I’ve got one strong belief: The smartest career move you can make is learning to work with people.

We spend years learning what we need to do in our jobs, but not how to work well with people and every interaction becomes something we have to figure out.

Meetings become draining. Building relationships feels like a performance. Sharing your ideas becomes daunting. And while we’re busy second-guessing ourselves, we miss out on the exact career opportunities we’re working towards.

Being good at your job isn’t enough anymore.

That’s why I built Human Skill School. It’s a 7-week programme (taught live by me) that teaches the human skills needed to work well with people and open up career opportunities.

You’ll go from feeling overlooked despite your ability and struggling to work with the people around you, to navigating workplace interactions with confidence, building stronger working relationships, and getting recognised for your work.

Our next cohort runs from Monday 1 June – Friday 17 July.

Join the waitlist and I’ll send you everything you need to know.