As a boss, it’s inevitable that you’ll have to have hard conversations. When you’re in charge, your time is money. How you allocate your time will affect your bottom line, which means you don’t have time to stew over difficult conversations. You need to have a plan in place for when situations like these come up so you can deal with them effectively and efficiently.
We’ve all been in a situation where you have an employee who is underperforming, and in turn, negatively affecting the entire team. Maybe you have a client who is upset and is treating your employees unfairly because of it. Perhaps one of your competitors is overstepping boundaries by copying your business model, marketing approach, or website copy. You could even have two employees who aren’t getting along and are creating a culture of gossiping within the workplace.
None of these situations are ideal, but they will most likely arise at some point if you’re holding a leadership position. If you’re scaling your company and adding more employees and clients, there will almost always be some sort of conflict that comes up.
I’ve had all of these scenarios happen at different points throughout my career, and it’s taught me that the more I avoid having difficult conversations, the more problematic and difficult they are to solve. These problems are like wildfires: if they aren’t contained immediately, they’ll continue to grow, and you’ll definitely get burned.
Here are five ways to have difficult conversations at work so you can have the best possible outcomes.
1: Practice empathy.
I had to fire a beloved employee once and it absolutely broke my heart. D2 is a small company, so we know everything about each other — what everyone’s kids are doing, where they go on vacation, and more. That’s one of the best things about having a small business, but it can also make things very difficult when you have to make a change in the team. She wasn’t the right fit for our company, and we tried to move her into several different positions, but it wasn’t working out. I took responsibility for hiring the wrong person for the job, but in my conversation with her, I had to step back and look at the situation from her point of view. She had a family, bills to pay and other responsibilities, so I gave her ample time to transition and even found her a job with one of my clients that she was better suited for. When you’re having a difficult conversation at work, try to put yourself in the other person’s shoes and have empathy for what they might be going through, instead of only focusing on yourself and your business.
2: Be honest.
In business, I’ve learned that the more you sugarcoat a situation, the more unclear your message will be, which will only lead to confusion and hurt feelings. In the past, I’ve tried to have vague conversations with team members when they were not meeting our standards. I wasn’t being direct, so the team member went back to doing exactly what they were doing before. Instead of beating around the bush, spell it out clearly (and slowly) and offer a solution. Maybe they need additional training or mentorship to succeed in their role. Honesty is always the best policy at work and your team members will respect you for it. Tell them directly what you need from them so they know how to step up.
3: Choose people over money.
I once had a client who treated our team poorly. They talked down to team members and were disrespectful, but I tolerated it for months because they were our largest-paying client. I almost had a team member quit over it and realized that the money wasn’t worth the suffering. I had to have a difficult (and months overdue) conversation with the client. To my surprise, the client didn’t realize they were coming across this way and their attitude improved drastically. Prioritize your team members and stick up for them. It’s better to focus on maintaining a strong and loyal team around you than to be overly focused on money.
4: Communicate your policies up front.
I once had a client who was two months late on their billing and owed me over $5,000, which was coming directly out of my pocket. This client was someone who I considered a friend. I knew they were waiting on a big payment in their business to be able to pay me, but I let it go on much longer than I should have. I had to have a difficult conversation with them where I let them know that were were cutting off all of their marketing and not working on their website until we were paid. These conversations are not fun, but they are necessary. I now have a policy in place that if a client’s credit card doesn’t go through, then we contact them. If we don’t get a response within 24 hours, we immediately stop our work until it can be rectified. If you have a policy that’s communicated up front, there will be no surprise if you have to take that action down the road.
5: Reflect on how you did.
After a difficult conversation, it’s worthwhile to reflect and consider what went well and what didn’t. Think about why you had certain reactions and what you should have said differently. It’s also always good to follow up with an email documenting the conversation to avoid any confusion.
Avoiding difficult conversations is never a good way to solve problems. Have the hard discussions early and move on so you can get your head back into the game.
