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Three difficult conversations: Why you need to address them now

Avoiding difficult conversations doesn’t solve your issue; it makes it worse.

If I were to break it down, I’d suggest that there are three common difficult conversations that management and leaders fail to have. Reasons behind avoiding these topics can be varied, but more often than not, it is due to unnecessary theorising about how uncomfortable initiating the conversation might feel. Putting your emotions aside is one of the many expectations of being a leader.

Offering honest communication will usually be better received than you have predicted – get out of your head!

It is time to address the three most critical difficult conversations to have, why it is essential to tackle them and five steps to make moving forward a positive experience for all those involved.

The First Difficult Conversation: Addressing Competency

If you’ve hired a team member whose performance is a six out of ten, the decision to let them go is pretty straightforward.

Okay, maybe not always, but if you have a performance management system in place, keeping someone performing at a six when you could have eights, nines and tens on the same salary just doesn’t make sense.

Sevens, however good their intentions are, will kill a business. They’re not your A players; these are your B players. Culturally, they might be a perfect fit, and you may have worked with them for a while. They’re not totally awful. They might even be good, but good isn’t enough when striving for excellence.

It feels like it will be a difficult conversation, but it doesn’t have to be.

Handling difficult conversations can feel daunting, but if you try to remind yourself of the other person’s point of view while sharing your own perspective, it makes for a more straightforward discussion. Now is your opportunity to find some common ground on what (in their opinion) is causing their underperformance and a chance to listen, learn and grow. Together or apart!

Remember that A players are proactive and don’t require hand-holding. The reality is that B players or your sevens are reactive. Often, they need ongoing guidance on what they’re doing. And even when you dedicate time and energy to micromanaging them, you might get adequate performance. Your A players don’t require micromanagement and give exceptional performance, so that is where the gap is. 

Suppose you can have a team of exceptional A players that can perform 5-10x more productively than your team of sevens. In that case, it’s time to reconsider things and have what you perceive as a challenging conversation, which you know you’ve been putting off.

Ask yourself, would I enthusiastically rehire them?

If the answer to that question starts with a pause, a sharp inhale or an “umm”, then you have answered that question as far as I’m concerned. That is as good as a no; the tough conversation with them about their competency to fulfil their role needs to happen now.

They’ll likely already have the self-awareness to know that their performance isn’t that of an 8, 9 or 10. If so, their agreement to this fact can open up the dialogue. Now, you can start brainstorming solutions on how things can improve within their position (in line with a performance review in 60 days; I’ll get onto this point) or begin the conversation surrounding their exit strategy.

The Second Difficult Conversation: When Their Job is on the Line

Usually, these things are a continuum, having failed to act on things earlier or having avoided the first conversation.

Their performance might have deteriorated, or if this has happened in a growing business, their role might have become more complicated. These organisational developments might mean they have gone from being a generalist to the requirements of their role to becoming specialists, and they don’t have the capability or competency to specialise in something.

Sink or swim; unfortunately, they’ve sunk like a lead balloon.

Their job is on the line, but you still haven’t had a conversation with them about their performance, which means you’ve deprived them of a chance to resolve the issues or mutually agree on the exit strategy which is possibly their desired outcome.

It’s important to remind yourself that no one wants to turn up every day and fail. Now is a good chance to understand this person better, leading me to the third difficult conversation.

The third difficult conversation: “You don’t want to be here”

It’s reasonable to feel nervous telling someone “you don’t want to be here” or “you don’t like it here”, particularly in workplace relationships. It’s improbable that there is a way forward if you find yourself having this conversation. This person has decided that the company, culture, role or management isn’t for them, and it’s unlikely you will be able to change their view of the world. And you shouldn’t have to; there are plenty of A players out there who will thrive in their place.

This scenario happens in acquisitions reasonably commonly. The change of pace or the performance culture has shifted, and they don’t like it. Too bad. They need to change with the times, or they need to go. Having a game plan when approaching these conversations is essential for transparency and can be broken down into five simple steps.

  1. 60 Day Success Plan: Now is an opportunity to set a plan into motion, a time for them to prove themselves if they want to keep their position in the company and become an A Player. Discover their idea of an A player, and see whether they’re willing to reach some KPI’s within one week, one month and 60 days from now. Now, there is a chance to coach them into being the A player you need them to be.
  1. Share what is at stake: Remind this person that improvement is necessary for their job to be secure. Sharing this is not a threat; this is business, and growing businesses require committed individuals who share the team’s goals, vision and collaborative success. Everyone in the team must be pushing forward, not dragging things backwards.
  1. Give examples of why this conversation has happened: It’s important to give real examples of what led to this conversation. Whether it has been failed KPI’s, lack of organisation, poor attitude or resistance to change, ensure your team member has the full picture and understands where things have gone wrong; otherwise, it might repeat itself, wasting more valuable time.
  1. Review the ongoing PIP and hold each other accountable: Allowing your employee to set their own goals and promises means they’re much more likely to be actioned. They have the power to turn things around and understand what the result will be if they fail to meet the agreed 60-day success structure.

Fundamentally, as the business grows, you will fine-tune your understanding of what an A player looks like and be able to predict B and C Player’s future failure much more quickly. Everything is an opportunity for learning and growth; have those conversations early and remove the unnecessary pain of watching someone fall behind.


Written by business growth coach Dominic Monkhouse. Find out more about his work here. Read his new book, ‘Mind Your F**king Business’ here.

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