Leading Difficult People: Practical Principles for Leaders

I hesitate to write under a title like this.  

It’s true that I have experienced leading difficult people. Apparently, some people have found it difficult to be led by me (crazy, right?). So, what do we mean by difficult people? How can we make this challenge simple, but bold and authentic? 

Here’s some practical principles for busy leaders everywhere. 

What we mean by “leading difficult people”

Difficult people are not a problem. Their behaviours are the problem.  

Before we square up to confront “difficult people” it’s important to step back and identify exactly what the behaviours are that may make them difficult for us (and it might only be us that finds them difficult) 

Ask yourself, when do you see those behaviours and what was the context? Was there anyone or anything else in the mix that was a compounding factor? Is it a one off or a series of issues? 

Sometimes, cooling off, stepping back, and starting with a clear problem statement can make the rest of the conversations a lot easier. It stops the discussions being coloured by too much emotion and will give you (and the listener) something tangible to get hold of and discuss. 

Labels shut down possibility

As soon as you describe a person as “difficult” you are globally writing them off, when in fact they may have much to offer you or your business. 

A UK politician Ken Clarke was caught on camera describing Theresa May, a prospective party leader as a “bloody difficult woman”. It sparked a wave of outrage and admiration. You can still buy T Shirts with the acronym BDW (in case you are interested!) 

The issue is this. Ken Clarke’s difficult woman ended up being the UK’s prime minister. Your difficult person might be someone else’s ideal leader or to quote Sheryl Sandberg “Next time you are about to call a little girl bossy say instead that she has executive leadership skills” 

Occasionally, once you have identified the behaviours, you may find your response seems out of proportion. Is it possible that you are part of the issue? 

Difficult people are like mirrors.

They often reflect things in ourselves which we need to work on. I remember one person in particular I worked with who was incredibly detail orientated – I would say almost obsessively (well I would, wouldn’t I?) – and they drove me to distraction. 

In fact, they were often right about the errors they saw in my work and at that stage in my leadership, I did not enjoy the constant critique. It took me some time to identify that, and come up with a good response which in the end made life a lot easier (by the way, part of that response was me improving my attention to detail) 

Sometimes, other people’s behaviours trigger something in us from past experiences (good and bad) that mean our responses are exaggerated or irrational. It’s worth noting those issues, and finding a good mentor, coach or counsellor to speak with about it. 

Build a support system around you

At FiveAndCo we think having a small group of trusted people around you is critical – a good coach, a trusted mentor, and sometimes a season of counselling – can all help you do well for the business and feel well too. It isn’t always easy leading people we find difficult, but if we do the work on leading ourselves, we can find it much easier to lead others. 

Difficult people are just like you and me but different. I have had the privilege of working with lots of different people, some of whom I find it difficult to appreciate but I do make the effort because I hope the people that find me difficult will also make an effort to appreciate me. 

Why is that important? Every team is stronger when we are trying to get along – to do well for business, and enjoy the energy, connection and meaning relationship brings. It’s the diversity of experience and perspective that helps teams thrive. 

Diversity of any kind – race, experience, gender, social class – is a gift to any team and every business. It stops us becoming isolated and fixed in our mindset. It brings colour, texture and perspective to our work. It also makes us human. 

Diversity is both an opportunity and a challenge. In order to fully understand others, you have to slow down, listen carefully and be truly present to a different perspective. You may have to surrender a favourite way of looking at the world. You may have to apologise, step back and start again. Your “difficult person” might actually be the difference, the competitive advantage, everyone was looking for. 

It is also possible that things won’t work out. Not every effort you make in leading difficult people will have a happy ending. We do our best to lead well not because we are looking for a happy ending but because it’s the right thing to do. 

In every respect, doing well and feeling well is an intentional act that is about you thriving, and creating an environment where everyone else can thrive too. 

That is difficult sometimes. The alternative is that you are surrounded by people who agree with you or look like you or sound like you or work like you. If you think difference is difficult, I can promise you constant unanimity is worse. You won’t do as well, go as far as you want, or win as often as you would like. 

Where’s the fun in that? 

FAQ’s

FAQ : What do we mean by “difficult people”?

Answer: “Difficult people are not a problem. Their behaviours are the problem.”

FAQ : What should I do before confronting ‘difficult people’?

Answer: “Before we square up to confront ‘difficult people’ it’s important to step back and identify exactly what the behaviours are that may make them difficult for us.”

FAQ : Who can support me when I’m dealing with difficult behaviour?

Answer: “If you are dealing with difficult people at work, it’s a very good idea to surround yourself with trusted people. It might be a coach. It might be a mentor. It might be your own counselling.”

Related Knowledge Hub Articles

Ending artificial harmony: https://fiveandco.com/from-polite-to-powerful-ending-artificial-harmony/

Protect decision quality under pressure: https://fiveandco.com/micro-rest-the-simple-habit-that-protects-leadership-under-pressure/

Trust and better decision-making: https://fiveandco.com/trust-the-hidden-driver-of-better-decision-making/