Dealing with Difficult Personalities, by Paul Kaye

Paul Kaye

by Paul Kaye

PSR Contributor

September 19, 2017




Dealing with Difficult Personalities


Great talent is the engine that propels our business forward. Talent who can see the opportunities the rest of us are blind to are essential for any company’s future growth. They help our brands establish a meaningful place in the minds and hearts of our consumers. They differentiate us. Through challenging the status quo, they drive us forward. But, the high performers who create the most engaging content or conceive the most innovative ideas aren’t always the easiest to work with. In fact, they can be the cause of many knuckle tightening moments and an unimaginable number of sleepless nights. Some managers would just prefer not to have them around. However, that is often the quickest way to build a mediocre team.

Managing high performers with difficult personalities is one of the hardest managerial challenges any leader faces. For some reason, I love it. I get energized when an opportunity presents itself for me to work with a ‘so-called difficult talent.’ I always feel that you are walking along the edge of greatness, just waiting for their next disruptive idea to be born. It’s scary and exhilarating. Personally I have always found it perplexing that so many managers have backed away from these difficult but high performers. I think it comes from the misguided belief that managers need to be able to control. Control everything. Difficult talent can’t be controlled. At best they can be tamed and focused in the most productive direction.

What do we mean by “being difficult?” There’s no simple answer. Behaviors show up differently between one high performer and another. They can be super competitive to the point where they trample over colleagues, leaving a trail of devastation and hurt behind them. They can turn everything into a drama; complete with adult temper tantrums and large doses of negativity. They can be so focused on their own achievements and contributions that they can’t hear suggestions or ideas from others; they belittle the input of others. They can also be incredibly explosive when things don’t go their way, shouting and storming around the building. ‘Being difficult’ can present itself in many ways, but in its basic formation it can easily be categorized as destructive behaviors or attitudes. 

It’s important to remember that there is a difference between ‘difficult talent’ and being surrounded by employees who are difficult. It is the word ‘talent’ that separates these two types of people. Talented people contribute something unique and of value to the organization. They are high performers despite the challenges they conjure up for managers. Difficult employees are just, well, difficult. They contribute nothing of value and their lack of positive engagement holds up progress and prevents momentum. Every organization needs to protect themselves from this type of difficulty. Be extra vigilant in the hiring process, and if one slips through remove them with haste. 

Difficult talent makes a difference. You need them. They are the spark that ignites your team. Raise your hand if you think Steve Jobs could have been classified as a ‘difficult talent.” Thought so! You can put your hand down now. Nolan Bushnell hired a young Steve Jobs at Atari and described him as “difficult but valuable.” Steve Wozniak, Apple’s co-founder, said Jobs would “directly confront people and almost call them idiots.” He was difficult, but he was talented. Most importantly, he was valuable.

When you have personalities on your team that are unique, things will never be harmonious. We should embrace that. Harmony feels like conformity and greatness is never incubated in that type of environment. When you have unique personalities on your team, don’t push them to conform… rather, encourage them to create. 

Working with difficult talent isn’t easy – far from it – and there is no simple one size fits all solution. But there are some techniques you should remember when you’re next working with a difficult talent:

  • Stretch them!  When we are faced with managing difficult talent we try to control them. We think that “If we can keep them on a tight leash there isn’t a lot of damage they can do.”But the opposite happens. They feel threatened and castrated. They become frustrated and feel misunderstood. This leads to them actually becoming more difficult. Talented people need somewhere to channel their energy. Provide them with challenging and substantive projects. Empower them to find new answers and create opportunities. Make sure they are constantly utilizing their skills. Never let them get bored.
  • Make feedback a priority.  Staying close to all of the talent on your team is good advice, but it seems even more important to be close to those perceived as difficult. Fostering a relationship based on honesty and frequent communication can help you focus their energies and efforts in the right direction. Often talent doesn’t realize they are being difficult. Because they are motivated by the desire to create, they don’t notice the effect that their behaviors and actions have on others or themselves. Provide regular feedback to them, both positive and constructive. The positive feedback reinforces the actions and behaviors you want repeated and helps drive them to use their talent in the most appropriate ways. The constructive advice is only useful if it helps them see the bigger picture; how taking these corrective steps can help them find success quicker. There is a fine line between feedback and micromanagement – the key is to establish yourself as a partner in their success; working with them to create a better future.
  • Encourage them to vent.  To prevent large explosions you need to help release the pressure….often! You should give them permission to vent. But only to you. Let them feel comfortable coming to you and venting about whatever is frustrating them. Let them share their pains. Encouraging them to vent to you demonstrates that you care about how they feel. Sit back and let them go. Don’t judge. Don’t interrupt. Wait for them to calm down. Give them a safe environment to be heard. It’s important that you don’t commit to solving their problems, but rather let them know that you heard them and will act on anything you think warrants your involvement. Its better they vent to you than to others. 
  • Don’t dance around problems. It’s always easier to manage and offer feedback to talent when there is no risk of confrontation. Difficult talent tend to present a challenge for most managers. We know they will have something to say and confrontation is likely. Therefore it’s easier to not address the problem in the hope that by ignoring it things won’t get worse. This approach never works. Instead you need to tackle problems head on. You need to articulate the issues as specifically as possible. If they aren’t playing nicely with others, tell them. If they are failing to meet deadlines, tell them. Once you have stated the problem you need to work with them to set clear and mutually agreed upon goals for improvement.
  • Keep your emotions in check.  Difficult talent will push you. They will test your boundaries. They will poke and prod at you. Conflict will arise. The worst thing you can do is allow yourself to respond emotionally. You must fight your internal desire to pull rank or to lose your temper. Be prepared for difficult conversations by asking yourself, “What emotion would I like to convey? After all, the emotions you put out are often the emotions you get back. Difficult talent will often leave you frustrated, and during these moments you need to remind yourself of what makes them unique. When they are producing at their highest level, what is it they bring to your team that no one else does or can? You tolerate – within reason – their difficulty because of the uniqueness they contribute. Never lose sight of their value.
  • Hold your ground. Never allow yourself to be intimidated. Sometimes these high performers can have more experience than you, or they are fulfilling an essential role in the delivery of an important project, and they use these situations to leverage your position. No matter the circumstance, never change your position out of intimidation. If you allow them to get their own way, then you display support for their disruptive behaviors and set a precedent for the future. You must remain firm with difficult talent no matter how much easier it would be to give them what they want.

It is your job as a leader to find the talent that is capable of changing your future. You are tasked with finding talent that can create rather than reinvent; talent that can create magic that would otherwise go unrealized. When you find that talent, it then becomes your job to manage and coach them to success. Shying away from potentially difficult talent is never the answer. You’ve already failed if you turn away talent capable of painting a new way forward. You need these people. You just have to be ready to manage and partner with them. You have to invest your success in them and walk side by side with them as they navigate the inevitable success and failures that will present themselves. Often you will find yourself reflecting on the classic saying, “We can’t live with these people but we can’t live without them.”  Difficult talent delivers a value to your business. Don’t shy away from them. Instead, embrace the challenge and become one of the leaders who work effectively with ‘difficult talent.’ It will be worth it!


Paul Kaye is VP, Product and Talent Development for Rogers in Canada.  Paul spends his days working with stations and talent across all of the company’s formats with a sole focus on helping improve performance and grow the business.  Prior to being at Rogers Paul held the role of National Talent Development Director for Newcap Radio and also a Group Programming role in England.  Paul is a certified coach and is passionate about helping individuals, teams and organizations find their greatest potential, which is the fuel behind his other project The Talent Lab. Paul lives in Toronto with his wife, 2 dogs and a cat – life is never quiet!  Reach Paul at **@th**********.co 


Paul Kaye





  1. This explains in part why there are so many boring personalities on stations struggling for ratings. Managers want to play it safe, and that means no risk no reward.

  2. I think that is fair in some cases Jimbo. But I am not sure it’s reflective of all managers. There are many who want to take risks in the talent they hire/work with, but often they haven’t had the chance to learnt the nuances needed to navigate talent management (and to be fair thats a ‘never finished’ project for us all). Managers can also be nervous to make a mistake and therefore opt for the easier option, which is understandable human nature; we all want to survive. The hope is that the industry allows managers the space to experiment and fail, and for managers to feel empowered to find interesting, challenging talent that will make a difference to their output.


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