How To Have an Unpleasant Conversation

Photo by Zdeněk Macháček on Unsplash

Confession time: I do not have a green thumb.

Recently my neighbor politely pointed out that my tallest, most healthy “shrub” in my front yard was actually one giant, monster weed. Once weeds get to that point (over 3 feet tall), they take on a mind of their own. They start to grow deep, stubborn roots and long, pointy prickers so even if you do have a change of heart and decide to get rid of it, that weed is not going down without a serious fight. And it takes lots of digging and pulling at the roots to make sure that it doesn’t just come back. Keeping your plants healthy is so much easier if you just stay on top of pulling weeds out when they’re small.

Every day problems arise in our jobs and in our teams that are little weeds. They start out small and innocent. Sometimes we don’t even know yet if they’re a weed or a flower. But be it because we are too “busy” or because we are avoiding an unpleasant interaction, one day we walk into work to find that something that we thought was a decorative cactus has grown into a man-eating Audrey II.

Ignoring issues at work has consequences. Don’t be that guy.

I have spent my entire career growing and pruning high performing teams. And the one tipping point that helped me to change my perspective on having difficult conversations is this:

A tough conversation is not about tearing someone down. Instead, it’s about building them up.

Pulling the weed isn’t killing the person — it’s getting rid of the issue that’s preventing them from being promoted.

It is human nature to not prioritize something until it becomes a problem. So it’s natural to think that ignoring a growing weed is going to be OK for the work environment. But once it grows into a big problem, taking care of the issue is much more challenging.

We ignore issues and wait until they grow into big problems all the time. And when it comes to having to “pull the weed” by having a tough conversation, more often than not people don’t address these concerns for one of two reasons: 1) they dislike having difficult conversations or 2) they can’t recognize a weed.

In both cases, a few facts can help to establish a baseline for healthy, thriving teams:

1) Every person has obstacles that will prevent them from flourishing. Everyone has their own weeds. The weed could be a habit of procrastination, poor communication, or a whole host of other reasons why you know they would never be considered for a promotion.

2) A leader’s job is to support people on their journey of becoming the best version of themselves in their role. You are the best person to start the conversation about pulling out the weeds.

3) A difficult conversation is easier to have early, rather than waiting for an issue to become a full-blown problem — a gigantic weed. This is because a colossal weed starts to suck the life out of everything around it. Weeds derail project deadlines. They lead to sloppy work. Once a weed is out of control, it hurts the rest of the team, affects everyone’s work, and is a poor reflection on everyone around it.

A mark of a successful leader is that they have a green thumb — not with plants, but with people. They create the optimal environment for people to grow and flourish. They support the people around them in becoming the best version of themselves in their role. They get rid of the weeds to help people grow.

In this sense, the way to have a difficult conversation is simple. Find the weed early and pull it out early. The weed is not the person, it’s the obstacle that is keeping the person from achieving success. When leaders understand their role as gardeners, there are no difficult conversations to be had. They are simply conversations.

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Shannon Shallcross

Shannon Shallcross

Executive Leader | Founder | InsurTech | DataTech