Dealing with brilliant jerks – how to have a difficult conversation

Confronting an employee is never easy, in this week’s episode of Platform Diaries. As the founder of a startup, the stress of this is only compounded. Your team likely consists of friends, or long-term collaborators who have been on the journey with you since day dot, you’re juggling other responsibilities and you may have never been in a managerial role before.

I personally know what it is like to want to leave conversations unsaid.

I once worked with a team member who was very well respected in the organisation I was working at. They were really clever and an expert at their job. Despite their success as an employee, they had the tendency to be quite abrasive. I thought that this was an opinion I held alone, and the rest of the team got along with this person well. This was until one morning; I got to work and found a brochure sitting on my desk that read ‘removing the cancer from your organisation’. I soon realised it was someone giving me a quiet hint that the person’s behaviour wasn't just being seen through my eyes, and it was impacting the broader team.

Despite Damien Gooden’s vast experience and expertise dealing with people, he can also empathise with the dread of initiating a conversation that will likely be awkward or uncomfortable. As the CEO of HR Central, Damien has made it his mission to get comfortable being uncomfortable.

“I was at a networking function that started early on a Melbourne winter’s day. I was one of the first ones there, and not long after I arrived a gentleman came in and got a cup of tea. I shook his hand and introduced myself and realised straight away that this guy had his jumper on inside out. I leant in pretty closely and said, ‘it looks like you have your jumper on inside out’, and he hit the jets,” Damien tells me.

What he remembers most about this anecdote is the person’s reaction. “I remember looking at them in that moment, seeing on their face that they are thinking ‘oh my gosh, I’ve just looked like a fool in front of a stranger’, wishing they could be one centimetre tall.”

While Damien didn’t enjoy this experience, he put himself in the shoes of the person with the inside-out jumper and concluded that he would definitely want to know if his shirt happened to be the wrong way around.

“The last thing I would want to do is get in my car two hours later, having met 50 people, and look at the rear-view mirror to see my jumper is inside out and feeling like a moron.”

It is the initial awkward moment that Damien believes you must get past in order to make an impactful difference. Once the Band-Aid is ripped off, and the initial shock of confrontation subsides, you are left with the space to have a meaningful conversation that can address the crux of the issues.

While many of us avoid confrontation, whether it be pulling up a team member on their bad behaviour or asking why an employee’s productivity has dipped, these conversations are often necessary to allow growth and success.

“There’s two points of view in HR that we see. One is that someone’s behaviour is not in line with the rest of the organisation, and the other is that a team or individual is not performing relative to their group. Both have that same level of toxicity,” Damien argues.

While underperforming can be slightly easier to quantify and call out, a “brilliant jerk” poses a unique conundrum. How does an employer intervene when one of their team members acts in a way that is pretty shitty, but works effectively?

“Preparation is number one,” Damien says. “You’ve got to have facts. Then, depersonalising the issue. Saying things like ‘it’s not you, it’s your behaviour when you do this’, or ‘when this happens, this is how you make people feel’. Then, I think it is beneficial to give an example of someone in that same circumstance behaving in a different manner.”

Another practical piece of advice that Damien offers is to break the news, then give the person 5 minutes to digest it.

“It may come as a surprise to some people, particularly in cases where you haven’t had the conversation and it’s been three months, or five years.”

As opposed to having the mentality that ‘well it has been five years, another won’t hurt’, Damien argues it is never too late to have the conversation.

“You can put yourself in a position of vulnerability and say that it is something you have just recognised, or that you should have done this a long time ago.”

Recognising this behaviour is step one. While this may seem easy, the increasing nature of remote work may hinder the ability for leaders to observe their teams.

“We could have a whole other podcast episode on virtual office environments, but from my point of view, it's still about having that airtime with as much of your team as possible,” Damien asserts.

Giving time to your team, asking them open-ended questions that are unrelated to work and building trust will create an environment where your team is more likely to approach you with queries and concerns.

There are also a growing set of tools, such as Readiness, which helps to monitor the wellbeing of your team.

“Another thing I would recommend businesses do is to let people have a buddy that's not even in the department. This gives them an outlet to talk with someone that they care about and trust,” Damien suggests for a cost-efficient alternative.

Damien also recommends Kim Scott’s book Radical Candour for practical tips, different approaches, and scenarios.

“The other thing is, don't be too hard on yourself if it doesn't go perfectly the first time. There’s a different human at the other side of that conversation and you don't know what's going on in their world. We’re all human, so don't be too hard on yourself if the first one doesn't go perfectly. Just reflect, take some notes.”

Is there someone in your team that you need to call out, but you just can’t bring yourself to do it? Or perhaps you want to create an environment where people are comfortable coming to you with their problems. Giving time to your team, and having the confidence to initiate these conversations are some of the methods Damien Gooden believes you can nip undesirable behaviour in the bud.