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Dealing with Difficult Personalities: 5 keys to re-engaging

Updated: Jul 5, 2023

By far the most common question I'm asked when talking about the work I do as a Leadership Expert and Communication Specialist, is 'So how do you deal with 'difficult personalities?' This is really code for I'm having a hard time leading, engaging and influencing someone in my team (and it's definitely them, and 100% not me)

Dealing with ‘difficult’ people in the workplace is unavoidable. However, it begins with recognising there are no difficult people, there are only “people”. Rather than difficult personalities, we are different personalities.

What we need to distinguish, and continue to remember is that difficult behaviour does not mean a person is a difficult person. It’s important to be able to identify and separate the behaviour from the person. While we can’t change other people, especially those we work with, what we can do is learn to work with the behaviour to be able to work with the person. And we do this by recognising and understanding the intents behind the behaviour and responding accordingly. Perceived difficult people are often misunderstood, which only causes angst for them and us.

In this article, I outline the five ways we can re-engage with the ‘difficult’ personalities in our teams and improve our leadership self-awareness.

The five key ways to re-engage are:

  1. Adopt an attitude of Generous Assumption - what’s behind the behaviours?

  2. Discover Intrinsic Motivation - what do people actually value?

  3. Communicate in the right language - how does your audience want information?

  4. Communicating expectations - don’t assume!

  5. Agreed accountability - you’re in this together.

Generous Assumptions

One of the guiding principles at Made for More is around having, holding and giving generous assumptions. What that really means is that most people want to do well at the work that they do. No one's really coming to work to do a mediocre job. Very rarely do I come across people that intentionally go to work to have a terrible time; to make enemies, to start fights, or to feel rubbish in the workplace. So, when there is something that's not either up to standard, or there are behavioural issues, there will usually be a few factors behind it.

Start by reflecting on the story you are telling yourself. If you’re already thinking of them as ‘difficult’, what is it that you're telling yourself about them? And then think about if they were coming to work to get along with everyone and do the absolute best job they can, what would the capability or capacity gaps be? Where would they struggle? Or what is it that they're missing to be able to feel good in the workplace?

Intrinsic Motivation

There are two main types of motivational drivers in the workplace: intrinsic and extrinsic.

Extrinsic motivations are things like: I come to work to get paid, I come to work for the perks, I come to work for any kind of externally motivating factors. My office looks nice… there are free snacks.

The flip side of that is our intrinsic motivators: people come to work because they are connected to the vision and the mission of the organisation. They might be deeply committed to offering great service or they might be deeply committed to the industry that they're in and really believe in what it is striving for.

It’s not a case of either one being wrong or right, it’s about tapping into which one works for the individual team member. To give you some context, years ago when I worked in banking and finance, with a big sales focus, we used to have sales stars every month. There would be a small prize of a store gift voucher for the winning sales star. After a while, we started tapping into what people actually wanted. Maybe they didn’t live near a Myer and didn’t want to shop there. Some people wanted a restaurant voucher. Some people wanted to finish work an hour earlier. Identifying at an individual level what people actually valued made this reward a lot more motivating. I think we don't spend enough time as leaders recognising what those individual drivers are. The easiest way to do it is just by asking, ‘Hey, what do you want?’.

Communicating in the right language

One of the biggest pieces of work that we do at Made For More is around Courageous Conversations, and helping leaders to navigate how best to communicate with their teams, colleagues and stakeholders.

We've got an entire Masterclass on Communication Styles and a Masterclass on having tough conversations designed to help teams to understand each other, and we look at it in different personality styles, different ways of communicating, barriers to communication, overcoming fears plus so many other practical tools to be able to elevate communication. During the Masterclasses we also identify your own communication style and then we also have a look at how the different kinds of people communicate with each other both from a sending and receiving communication perspective.

It’s really important as a leader to understand how the individuals in your team like to communicate and to refine your messaging accordingly. One of the biggest and easiest leavers a leader can pull is the communication leaver.

Communicating expectations

Often, when we’re setting expectations we do a lot of assuming (and you know what they say about ass-u-me-ing). We assume the other person understands the expectation in the same way we do. Rarely do we circle back and check that we have a shared understanding.

This has happened to me on a basic level with my beautiful husband. Once, pre-kids when we had the time and energy, we renovated a house. I’d read all the magazines and picked my colour scheme so I sent him off to Bunnings to go and get some grey paint for one of the feature walls. I'd shown him a picture of the grey I wanted - a beautiful, slightly off-white, pale grey. It was perfect... You may know where this is heading... He came back and started mixing the paint can, I could see it getting darker and darker. I asked him which grey he had bought. He said just the one that looked good to him. A deep grey. My understanding of grey was completely different and much lighter! His understanding of grey was dark grey. And I think the same thing happens all the time in the workplace as well.

We're assuming people know or understand things in the same way we do. So being really clear and being able to communicate the expectations, particularly around things like timelines and deadlines. Even around the definition of ‘done’ - pay attention to that as it means different things to different people!

Agreed accountability

The last key is around agreed accountability and it ties in directly with setting expectations. Often I see accountability pieces start off well - we get accountability during the meeting or the moment, but then things start stretching out, a week becomes two. This is when we need to say: this is the accountability we agreed on, if things aren’t happening when they should be, we need to find out why.

Stay calm, stay self-aware and work through these five areas to re-engage your team member, no matter how different (difficult) they are!

Until next time Eat the Frog, Get the Worm, Be the Bird, and start re-engaging.



Ally Nitschke is a Leadership Expert, Courageous Conversation Specialist and Speaker. She has been working with leaders and as a Leader for over 15 years. She is on a mission to change the way we communicate at work, to lean into those uncomfortable conversations and lead with courage. Ally delivers Courageous Conversations Programs, Courageous Leadership programs, Coaching, Mentoring and Keynotes. To inquire about her working with you or your organisation please contact us here.


If you are interested in having Ally speak at an upcoming event or would like more information about Ally's Programs please book a call.

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