The Hardest Part about Being the Boss: How to Give Regular, Honest Feedback to Your Employees and Contractors

My stomach was tied in knots. I had been fretting about it for a week. I wasn’t sleeping well, and I was eating too much junk food.

It wasn’t going to be an easy conversation.

When the clock hit 3:00 that afternoon, I knew it was time. No more preparing. No more trying to get around it. It was going to happen.

He came over to my desk. I suggested we get a room. We quietly walked down the hall, found an open room, and shut the door.

I was shaking inside. I’m sure he was uncomfortable, too. He had to know that something was up.

We need to talk about your work. There are things that need to happen that aren’t getting done. It’s beginning to have a significant impact on the project’s progress.

That was the beginning of my first “performance conversation,” as they call it in the corporate world.

As a new manager in a Fortune 500 company, I was trying to play by the rules, following the guidelines and expectations about employee feedback. This company had a “process” for everything. (Insert eye roll.)

I needed to let this guy know that things weren’t going like they needed to. I wanted him to do well–it was easier for both of us if he was successful. Failure (firing) was a lot harder on everyone.

However, in order for him to be successful, he needed to know the truth: Some things weren’t going well, and if they didn’t change soon, there would be more “processes” to follow.

The hardest part

It’s not easy to give feedback to someone who isn’t doing a good job. It’s uncomfortable. We’d rather pretend “they’ll get it right next time” or “they should know better.”

However, most employees don’t know they’re not doing something right until you tell them.

Deep down, most people want to do good work. Sure, there’s a slacker here and there who wants to get away without doing much work, but in general, people want to make a positive contribution. By giving feedback, you are giving them an opportunity to do a better job when you tell them where they are falling short.

If you have an employee or contractor that puts in significant hours for your business (3 or more each week), you need to make time to give them feedback–in person. Talk on the phone or over Skype if they work remotely. Do not solely rely on email. On small tasks or requests, that works, but for a conversation about their job performance, talk to them.

Be specific

Give your employee specific feedback about what they are doing and why it’s not exactly like you want it to be. Tell them how you’d rather it be done. When you give someone specific feedback, it’s easier for them to adjust their work.

Be as specific as you can be. If you want them to “be friendlier to customers in email,” there’s room for interpretation as to what that means. Instead, tell them, “Always start out with a friendly greeting like ‘I hope you are having a good day,’ and end with ‘Let me know if there is anything else I can to do help.'”

We are not mind readers. Each one of us needs to be told if you want something to change. Don’t assume employees know what you want, regardless of how long they’ve worked for you.

Even when they are amazing

If you have an employee or contractor who is doing a fabulous job, tell them! Tell them in person. Email notes are great, and phone or Skype conversations are even better.

As odd as it seems, even “You’re fabulous!” conversations can be awkward at first if you’re not used to giving feedback. Do it anyway. Be specific. Tell them exactly what makes you so happy. They’ll love you for it, and it feels good when it’s done. It is also a great way to increase employee retention.

Make it regular

In larger businesses it’s common for managers and employees to have regularly scheduled, one-on-one meetings. Depending on the individuals and the business, these meetings could be weekly or monthly. I recommend entrepreneurs adopt this practice.

Whether you meet weekly or monthly with your employees or contractors, regularly scheduled meetings are an easy way to address both tactical items and job performance feedback. When you establish a regularly scheduled meeting, both of you will get in the habit of bringing questions and ideas to the conversation. You are likely to discuss things that would otherwise get ignored if you didn’t meet.

It’s your job

You are the boss, an employee, and the human resources department. You do the hiring and the firing and everything else in between. It’s your job to give feedback to your employees and contractors.

In the long run, providing consistent feedback to employees builds trust and accountability. If you end up letting an employee or contractor go, you will have set yourself up for an easier conversation when the time comes. They will have heard you give them feedback on their work and may realize that they are not the best fit for your company. It’s far better than surprising them after months of you thinking they should know better.

When I started “regular performance conversations” with my employee several years ago, we established a foundation of trust and accountability. He knew that I would tell him where he stood and hold him to his commitments. He knew there would be no surprises. I made it so he was able to adjust how he did his work, meet the company’s expectations, and keep his job. That first difficult conversation made work easier for both of us down the line.

Make the time for regular feedback with those who work for you. It’s easier for everyone in the long run.

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