How to manage difficult employees

Serial entrepreneur Gary Ashworth reveals the tactics that work for him
Gary Ashworth

There are only three certain things in life: death, taxes, and encountering difficult people. However, we often don’t merely encounter difficult people; we have to find a way to manage them. 

We’re all difficult people, though, aren’t we? We all come packaged with our own odd characteristics. We all want to be validated, recognised, loved, included, promoted, praised; we all want to have a good moan sometimes. 

In this post-Brexit, not-quite-through-Covid world, the workforce is restless. If you don’t make your flock feel valued on a regular basis, the best sheep will be gone by the time you can say baa humbug. One thing is for certain, though: people change jobs more frequently in this new digital economy, and we can expect this process to be magnified in the current environment. In fact, according to figures compiled by the London School of Business and Finance, 47% of UK workers actively want to change careers. There is also significantly less loyalty to brands or individuals in this environment, so the more that we can retain our existing talent pool, the easier it will be to grow our businesses. 

There are staff shortages everywhere, and the war for talent is raging. Wage inflation is rife; in the businesses I’ve been involved with, salaries have risen by over 20% in many sectors. One US law firm, for example, is paying £140,000 starting salaries for juniors. Head-hunters are circling like vultures – I know this for certain, because I am one – and there’s no longer any stigma attached to regular job-hopping. 

However, because of this very candidate-led market, employers face a very demanding pool of talent, and this will undoubtedly mean working with and managing some difficult characters. So, how do you effectively manage those more troublesome individuals in the workplace?

Before we go any further, there are such things as hopeless cases. If you’re stuck with racist, sexist or violent people, get rid of them. There is nothing you can do for them. If you attempt to sand down their rough edges, you run the risk of falling foul of employment legislation. It takes too long to change their behaviour, and your time is too precious. The good people in the workplace can easily become infected, as unreasonable people often try and persuade people to share their views. 


Train your staff well and help them reach their full potential. People are most loyal to the managers who keep developing them. Think of yourself as their personal trainer at the gym, pushing them to be the best they can be, giving them permission to be great. Understandably, people become irksome when they are badly managed, and are more likely to leave, seeking greener grass. 


Most people have left a job at some time in their careers simply because they were managed badly. Considering the time and expense associated with hiring, onboarding and training a new person, you should always look to keep your good people in place. In 2015, Harvard Business Review reported that the organisational costs of employee turnover range between 100 and 300% of the replaced employee’s salary.


Workers become more difficult when they become bored in their roles. Their irritability can stem from being underworked. Don’t be afraid to work them hard and showcase that you, as an employer, trust them and want them to rise to necessary challenges while stretching themselves and their abilities. 


Don’t let staff problems fester. Disgruntled people look for others to moan to – and negativity is more infectious than the common cold, so it needs to be stamped out quickly. Prevention is better than cure, so ensure you have transparent communication channels and operate as much as possible with honesty and openness to nip issues in the bud before they grow into something bigger than they need to be.

"Disgruntled people look for others to moan to – and negativity is more infectious than the common cold, so it needs to be stamped out quickly" says Gary Ashworth


Home working can be the root cause of many employers’ unconscious biases. Those employees who attend the office more often (and are therefore more ‘visible’) are more likely to get praise, form stronger interpersonal relationships with their managers and colleagues and, perhaps not intentionally, be the more likely candidates for promotion. Additionally, home working is undoubtedly going to exacerbate gender inequality and negatively affect diversity and inclusion efforts. Those in care roles, traditionally women, may opt to work from home more often than their male counterparts in order to integrate domestic life more seamlessly with work life. They therefore risk becoming overlooked in the workplace due to a lack of visibility, and they will miss out on moving up the career ladder, widening the gender pay gap. Avoid either of these problems as much as possible and ensure you create a level playing field for the whole team, who can then grow and strengthen as one unit without leaving anyone behind. 


There’s no place for anger in business, even when faced with the most challenging of behaviours. It’s a sign of weakness. Remember that you don’t have to be ruthless to be rigorous; you can still set performance standards and measure them without bullying. Rather than throwing your weight around, make it clear that your people are required to meet the expectations and ethos of the business, and then act when they fail to deliver. This will be far more effective than ranting and raving. 


We talked about capturing and measuring data earlier in the book, but it’s not just about the bottom line. The pulse of any business is always its people and, in fact, the best stethoscope to measure this can often be the consideration of soft factors. This doesn’t mean becoming a practising psychologist or turning your business into a crèche! But it does mean paying heed to important human factors. Is there a sense of humour about the office? Is morale noticeably high or low? Do people have positive feelings about their working environment? Are they ultimately enjoying working for the company? These are all key questions that managers need to be asking and addressing, if they have any pretence of running a successful business. It doesn’t matter how profitable a company might be; if the staff are miserable, it will affect growth. Fostering a positive mood among your workforce is critical. This can be achieved by concentrating on some relatively simple strategies and techniques. Seek feedback from your people and provide regular feedback yourself to managers within the business. Identify the trickiest employees and ensure that they feel valued, while also acquiring regular feedback from them. This is another way to ensure that they buy into the ethos of the company. I’ve noticed that people who are apparently behaving outrageously often believe their conduct is completely reasonable. Not all bad behaviour is underpinned by malice. People frequently don’t realise how destructive they are being and often you need to understand the underlying factors that have led to their conduct. 


Troublesome staff can very much be compared to attention-seeking children. They start getting bored, become playful, and ultimately end up being disruptive if they don’t understand the boundaries of acceptable behaviour. Luckily, though, they also tend to respond favourably to praise. This means that it’s critical to celebrate the success of all people within your business. Ironically, this is something that many managers fail to do adequately. Yet patting people on the back for a job they’ve done well can make a massive difference to their productivity going forward and can even affect their mindset about the company and their role within it. Sometimes, encouraging words can achieve as much as a salary increase, and neglecting this on a regular basis can be considered careless management. Praise is free – and people love it! It could be argued that one of the consequences of our social media-driven culture is that people tend to crave recognition. This is a monster we have willingly created; it’s a monster, though, that also represents an opportunity, as appropriately lavishing praise on staff members can do a tremendous amount for morale. There is no one happier than the staff member who feels valued, who is beaming with pride inside, and this person will rapidly become a highly productive worker. 


Much of our work is based on self-reporting, and we know that marking one’s own homework can be unreliable. We’re rarely less accurate than when talking about ourselves! To thicken the broth even further, this can work both ways. Some people are prone to what I call ‘pro-noia’. It’s a made-up word that means the opposite of paranoia. Many people I’ve worked with, especially in sales roles, are under the illusion that people are saying good things about them behind their backs, amplifying their achievements while significantly playing down their failings. They aren’t. It’s a fantasy. You may have noticed someone in the White House recently who was often prone to this… Conversely, there are people with less confidence who mark themselves down. Perhaps they have a negative mindset and have a tendency to downplay their qualities and focus on what they perceive to be the weaker aspects of their personality or performance. What this means is that staff often fail to articulate their challenges. Consequently, we don’t address the real reasons that are holding them back. But with a little practice, we can teach ourselves to examine what’s happening and not to jump in and fix the wrong things. If one of our workers is failing, we need to think carefully about the reason why. We might assume it’s lack of product knowledge, when really they don’t believe in what they’re doing. In this case, more training won’t help. Their belief system needs boosting. Alternatively, it could be that their environment at home has become untenable, or they’re going through a break-up. In this case, challenging their behaviour won’t help. You need to get to the root cause of their particular issue. Everyone’s different. Don’t make the mistake of trying to fix the wrong thing. 


There isn’t a one-size-fits-all approach; you’re going to have to size people up. Sophisticated managers act as though they’re making bespoke clothes in a Savile Row outfitter. Different techniques work better with different people. Something that motivates one individual will have absolutely no impact on another – but that’s absolutely nothing to worry about. We’re all different. Some of us relish structure, some of us enjoy being creative, some of us favour sedentary tasks, and some of us can churn out number-crunching. There is no right or wrong, only different shades of humanity. Modern management is about having the flexibility to add an individual element to the way that we manage people, while retaining a clearly defined framework of ethics and values. But within this framework, it’s also important to acknowledge that human nature and instinct hasn’t changed and isn’t likely to change significantly in the future. Think of this approach as a more sophisticated version of the traditional carrot and stick. 


Another aspect of our individual nature is that we all have different strengths and weaknesses. A person who appears to be a genius when conducting certain aspects of their work will not necessarily be well rounded in all facets. In fact, they may even fail miserably at other elements of their work. For example, some talented salespeople may win new clients with relative ease but may leave a wake of administrative disaster behind them wherever they go. You might be addressing this kind of issue continually and still experience absolutely no improvement whatsoever. Society, and perhaps even human nature, encourages us to improve our weaknesses and view them as areas for development. I consider this to be backward thinking and ultimately counterproductive. After several decades of attempting to improve my own weaknesses, I don’t mind admitting that I’ve given up completely. Instead, I focus on doing more of what I’m good at. This is considerably more liberating, far more productive and a key secret of all successful people. If you experience a skills gap, don’t try to become all things to all people; hire someone else to prop you up. This is why you should build teams with diverse and complementary skills in the first place, in order to ensure that every base is covered. Assemble a collection of players with different assets – doers, dreamers, optimists, soothsayers and moderators. A racing team made up of brilliant drivers wouldn’t even get the car built, never mind win the race. 


Although in this book we’re focusing on successful management, it won’t come as an earth-shattering surprise to learn that many organisations tolerate dreadful layers of management. It won’t come as a shock to many readers because they will have been on the receiving end of lazy, uncaring or biased management. 

They know that complaining about it won’t help. Just the opposite: it’ll be career limiting. Some organisations are extremely fortunate and succeed despite (not because of) their management culture. We see high-profile examples of this being reported in the media on a regular basis. Many high-profile and well-known leaders engage in bullying or intentionally encourage a culture of fear and blame. It’s an unnecessary barrier, though, and the consequences of bad management don’t always become apparent for some time. Narcissism is still rife in business. I’m perpetually surprised and horrified by the almost hypnotised state and blind faith that otherwise intelligent people develop. They invest in following atrocious leaders – people who have long since stopped taking advice from their peers before proceeding to lead their companies or countries into chaos and madness. This is all so avoidable, so I hope that at every level we can begin to make more rational management choices going forward. 


Finally, it’s important to remember that most of us have been troublesome at some point or another (I know I have!). If we reflect on our working careers, it’s usually possible to identify a time when we were difficult to manage. There may be times when we’ve felt out of our depth and should have asked for help but didn’t.

There is a phrase used in the business community: ‘Communication is only as good as the response you get’. If you’re not receiving the desired response from someone you’re communicating with, you can reasonably conclude that it’s you who are at fault, not them. It’s advice worth heeding. 

Equally, it is important to remember that all companies need behavioural standards. All unacceptable conduct needs to have consequences. The best way to deal with people is to isolate any problems, work with them to correct the issue, and assiduously measure their progress. Ensure that they receive rewards if they’re doing well, but make sure there’s nowhere to hide if they are doing badly. 

Be patient and forgiving; lead your flock well but keep them in check. 

You may think you’re an important businessperson, but it’s more important nowadays to be a competent shepherd.

This is an adapted extract from Eat the Pudding First by Gary Ashworth, available from bookstores and Amazon

Written by
January 5, 2022