The 3 most difficult conversations leaders fail to have

Nothing gets people squirming more in their chairs than mustering the courage to have difficult conversations.

The 3 most difficult conversations leaders fail to have

Nothing gets people squirming more in their chairs than mustering the courage to have difficult conversations. They hope that things will simply “right themselves”, or that the problem might disappear after a period of time. The truth is you’ll never reach your full potential until you step into the discomfort of having difficult conversations, sooner rather than later.

The art, and benefit of having difficult conversations was something really drilled into my time at McKinsey & Company. At McKinsey we operated as a team, not a family. Great sports teams are constantly on the lookout for the next best players and culling the bottom of the pile from their line-ups. They know this is the only way to have a shot at the championship in any given year, and to create an enduring program over several years.

Teams and families are very different. The players on a team will change often and the team is optimized to win at all times. Families, on the other hand, naturally strive to stick together no matter what.

Most leaders and managers would benefit themselves and their organization tremendously, if they decided to truly run a team, rather than a family.

In my experience, across my career and as a CEO coach, the 3 most difficult conversations that leaders fail to have, roughly fall in 3 buckets. These 3 categories also escalate in the severity of the conversation.

1) Good but not great performance. This is a funny one, but it’s almost like we’re afraid to say anything, if a member of the team does a fairly good job, because, well, they did a fairly good job. But we’re not playing for fairly good, are we? Fairly good doesn’t win championships, battles, or market share. Does it?

Sometimes just saying it how it is can work really well, such as I can see you did a fairly good job here, but I think we both know you have so much more potential than this, and could have done even better. Or with a more future orientation, such as Alright, so we did fairly well on that project, and we also learned a lot. On that note, how might you complete this project differently in the future”, or “How would the best version of you have done this a bit better?

2) Your job is on the line. Time and time again, when someone’s job is on the line they hear about it way too late. So late that they’ve often passed their chance to improve. In my experience that lag can be anywhere from 3 to 9 months. 3 to 9 months for everyone else on the team to see the exact same suboptimal performance that you see in the perso – and then also question your leadership as they wonder why you’re not doing anything about it.

The moment you realize someone might need to go, if they don’t improve, is the same moment you should be scheduling the meeting with them to tell them this.

There is a window of opportunity, whereby somebody could improve if they understood the consequences of not improving. Don’t do them the disservice by letting that window pass.

3) You’re fired. This one doesn’t need much explaining. Or does it?

One of the important roles of a coach is to boldly ask the questions nobody else dares to ask you. Often a client will come to me with what they think is a macro question, only to discover it’s actually a micro question, and that there’s a much bigger question and answer for them to step into. Some time ago a CEO complained to me about the performance of his business partner. He was desperate for advice on how to pull the nose up on his partner’s performance, and course-correct the plane. Instead I asked him, “If we were able to magically let go of your business partner today would you ‘rehire’ him? “No”, was his response. Sometimes instead of course-correcting the plane you just need to crash it, and hop a new one.

The bottomline? Most people postpone difficult conversations, whereas top performers see them as opportunities for growth, and accelerate into them. They’re magnetizing by them, because they know that just on the other side of that “fear door” lies a better future.

So, if the most courageous version of you was sitting with you right now, is there a difficult conversation they’d advise you to have? With whom? Write down their name – and now schedule the conversation.

Eric Partaker
Eric Partaker

Share via
Copy link