It’s Inevitable: How To Have Tough Conversations With Your Employees

April 21, 2015

While popular media likes to portray entrepreneurs as fearless conquerors willing to storm the beach single-handedly, the reality is that entrepreneurs are quite a diverse population. Sure, it takes courage to be an entrepreneur, and there are many who don’t back away from a challenge, but there are just as many who would rather avoid certain aspects of the job — and that often includes having tough conversations with their employees.


There are a variety of reasons for this. Sometimes they hope that the problem will just fix itself, but that’s rarely the case. Others simply have a fear of conflict or of not being liked.


Our culture often labels people who are willing to have tough conversations as mean or worse. But I completely disagree. In fact, a willingness to have these conversations shows that you care enough about your team to put yourself through something uncomfortable in order to rectify the situation.


Sorting It Out Could Save Your Business

The fact of the matter is that hard conversations are necessary in any organization, but they can be especially prevalent in startups.


After all, in a business’s formative stages, there’s a lot of room for misalignment. And if this misalignment goes unchecked, it will only snowball into resentment, which diverts attention from what’s important and can even devolve into active or passive sabotage. What’s more, in a startup, things move quickly — very quickly. Startups are in a constant state of organizational change, and every few months, your company may look and feel completely different. As you add more individuals to your team, each with their own values and opinions, you’re bound to run into conflict.


There are five areas that nearly every entrepreneur ends up having a hard conversation about at some point:



  • Personality conflicts: People approach life from different perspectives, and unfortunately, some can’t stomach the idea of getting along with people who don’t view the world through the same lens.


  • Inappropriate or unprofessional behavior: This one might seem like a no-brainer, but some people simply don’t know how to behave in the workplace.


  • Underwhelming performance: Again, this is a no-brainer, but when performance begins to slide, you have to correct it before it has a negative impact on the company.


  • Organizational growth: As your startup scales up, a person who was a perfect fit in the early days might not be right for the second stage. In some cases, that person might even be you.


  • Organizational cuts: If your company fails to meet its goals, you’ll likely have to make some tough choices about whom you can afford to keep.

In this last case, it can be an especially difficult conversation to have. Even if your teammates are working their tails off, you may still reach the point where you have to let someone go when the numbers aren’t where they need to be.


Never Wing a Tough Conversation

When you’re faced with uncomfortable conversations like these, a direct approach is often the most effective. I’ve found that honesty, transparency, and timeliness are key to reducing the negative impact. In fact, there are four key things you can do to make a hard conversation easier, regardless of the situation at hand.


1. Don’t avoid the conversation. Trust me: Problems don’t age well.A lot of people make the mistake of keeping quiet and hoping things improve, but oftentimes, the problem only snowballs, so be proactive.


2. Have a plan. Whatever you do, don’t just wing a hard conversation. Take the time to think through the issue, brainstorm some tangible examples to illustrate the impact that the person is having on the company, and decide what you’ll accept as a resolution.


3. Be mindful of your language. People sometimes say and do things that lead to increased anxiety and defensiveness in hard moments. But when you don’t keep your emotions in check, you tend to derail the conversation. Be careful to present yourself in a way that doesn’t come off as accusatory.


Above all, be open to the fact that your perception of the situation may not be the only one. One-way communication is never fruitful. Of course, there are times to adopt an unequivocal approach, but difficult conversations are rarely one of those times. For this and other reasons, it’s essential that you engage in active listening.


4. Don’t conclude too quickly. Never go into a conversation with a specific outcome already decided. By the same token, however, you must always leave the meeting with a clear plan in place that leaves no room for interpretation. If you end the conversation without developing a plan for moving forward, then nothing has been accomplished.


I’m not sure that anyone really enjoys these types of conversations, but for the good of everyone involved, sometimes they’re necessary. In the end, your goal should be to communicate that the conversation is difficult for you, too, but that you’re committed to having it because you care about the employee and about the company.


This article originally appeared on Forbes

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