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Why You Need to Have Hard Conversations Sooner Than Later


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A problem deferred is not a problem solved. Just take my recent experience with cold plunges every day. The anticipation of the chilling water doesn’t fade, but I have learned that hesitating is the least helpful thing to do because within a minute of getting in, my body starts adjusting to the temperature and I’m glad I took the plunge. I have experienced a similar hesitation many times when considering having an uncomfortable performance conversation with an employee. But the sooner I address the issue, the better the outcomes for the individual, myself and our company.

It’s easy to imagine other managers struggling with the same hesitation. Without proactive and clear communication, minor issues typically escalate, becoming more complex and challenging. From my experience, initiating tough conversations early gives people more time to address issues before emotions intensify. Much like my cold plunges, jumping in without delay becomes less daunting over time because seeing the positive results motivates us to confront problems early and head-on.

Related: 5 Strategies to Ace the Difficult Conversations in Your Business

The mistakes leaders can make

Friendly and team-oriented managers often feel uncomfortable discussing performance issues with employees, and I was no different. Having done it wrong enough times now, I recognize how I used to justify avoidance. I would tell myself: “Well, they may be missing some expectations, but they’re not that far away.” I would convince myself that people would feel micromanaged if I talked to them too soon. In reality, that was an excuse for not doing my job, which is to help people get better through positive, constructive feedback.

The approach I take today is akin to a football coach. I take personal responsibility for the people I hire, so I remind myself that, above all, I want this person to succeed. I use that feeling to force myself to step up and initiate tough conversations. I care about my employees, so giving them feedback early and often will help them get back on track faster and make them more successful.

Reframing these difficult conversations in this way has helped me tremendously, but I also had to learn how to have them in the most constructive manner so employees feel good or at least at ease about having them, too.

The art of diplomacy

Everybody has different thresholds for what they consider to be good or bad news. I have found that it’s more common for people to almost overreact to even minor critiques, but others will not fix things unless the feedback is explicitly clear that it will impact long-term employment. It is up to the manager to understand the person’s personality and think how best to deliver potentially difficult feedback — whether that means having a light touch or holding a very serious your-job-is-on-the-line conversation.

To avoid creating anxiety, it is best not to make tough conversations a big, formal event. Frame the conversation positively, so as not to dismiss what the employee is doing right. I might say, “Hey, you’ve been doing an awesome job. I noticed you’re just missing the mark in this one area. I want to bring it up now to make sure you’re informed. Let’s check in on it over the next few weeks so we can stay headed in the right direction.”

It is best to raise issues face-to-face since it’s easy for people to misinterpret the tone of emails. At times, I have successfully laid the groundwork for constructive conversations via email, but it worked because I then spent time building them back up face-to-face. No matter where managers choose to talk to employees, the X-factor always circles back to the relationships they have built because people need to have enough trust to believe what a leader is actually telling them.

Related: These Are the 10 Most Difficult Conversations to Have in the Workplace — And How to Handle Them

When employees won’t change

If somebody really wants to apply themselves, they can typically get back on track when they start early. Oftentimes, all it takes is giving them proper guidance and support. People must believe their leader wants them to succeed, and that largely comes down to the manager’s mental prep leading up to the conversation.

Over the last two years, I have probably had to talk to four or five people, and most of them are still with our company today. When I’m not sure about an employee’s commitment to improvement, I have adopted a strategy inspired by Zappos: I offer them an option to take six weeks’ severance and leave straight away if they are not up for the challenge. But here’s the catch — if they stay, fail to improve and then I have to let them go, they will receive only two weeks’ severance.

This approach has proven incredibly effective. Those who decide to stay after being presented with this choice really push their limits and improve their performance.

Taking the plunge early

When someone on the team isn’t pulling their weight, it affects everyone. That’s why leaders have to act fast. But here’s the catch: If you rush into firing them, it is a morale killer. Wait too long? Same deal. So, I have figured the best move is to heed the warning signs and heed the warning signs and tackle these issues early and head-on — like ripping off a band-aid or jumping into cold water.

To make all of this easier, I make sure my team knows I am all about their success. This way, they are more open to tough feedback and it builds their grit. The bottom line is dealing with performance issues early on makes us better leaders. It may not be easy starting those hard chats, but the sooner leaders do, the sooner it becomes second nature — no hesitation, just step right in.

Related: 3 Reasons You Should Have Difficult Conversations Now

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