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Advice for founders dealing with defensive or troubled employees

Two founders are grappling with very different worker issues, but both cases call for empathy.

Advice for founders dealing with defensive or troubled employees
[Source illustration: cienpies/iStock]

Editor’s Note: Each week, Fast Company presents an advice column by Maynard Webb, former CEO of LiveOps and the former COO of eBay. Webb offers candid, practical, and sometimes surprising advice to entrepreneurs and founders. To submit a question, write to Webb at dearfounder@fastcompany.com.

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Q. I have someone on my team who’s working hard and doing well, but she has room for improvement. Whenever I try to give her feedback, she becomes defensive. We wind up putting a pin in the conversation, and I don’t get to move ahead with my intended agenda. What am I doing wrong?

—Second-time founder building a health app

Dear Founder,

As a leader, it’s your responsibility and obligation to help people improve and achieve their potential. That means giving feedback is an important—and often difficult—part of your job. Thoughtful feedback may be a gift, but people often don’t see it that way. For this reason, you must deliver your notes on her performance in a way that the recipient will be open to receiving it. Some tips:

Praise in public, criticize in private. Always follow this rule. And remember, people are watching how you react. It’s not just what you say, but how you say it and how you hold yourself.

Understand where the person’s head is. Feedback is best given when people are receptive. How do you know? Ask them. Say: “Are you in receive mode?” Or: “Do you have some time for a one-on-one? I had some suggestions I was hoping to share with you. If you are not prepared for that now, we can discuss at another time.” Setting up the conversation in this manner is a way to clue them in to what is happening and to make them aware that you are here to help them.

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Build trust. Do the necessary work in advance. People receive feedback better when they trust the person delivering it. Ideally, the recipient should understand that you’re sharing thoughts in the interest of serving their needs. The more trust you can build, the easier it is to have more difficult discussions, because you come from a place of working together rather than a place of judgment.

Give feedback constructively. When I started my career, I received notes from Mad Men-style bosses who used feedback as a weapon to chastise. However, much like bullying, this approach has gone out of favor and is unlikely to yield great outcomes. Feedback should provide validation and inspiration.

Be thoughtful. Have everyone else’s best interests at heart. Deliver feedback with good intentions. Don’t hold these conversations when you’re angry, because it’s far more likely the recipient will feel hurt or judged—and thus defensive.

Don’t shy away from delivering feedback just because it’s hard. We can’t take the new nicer workplace to an extreme and let it remove our ability to offer constructive feedback. Tough love can go a long way on the path to improvement. 

Q. Something bad is going on with one of my employees, who is bringing these personal issues to work, but I don’t know what the problems are. In this day and age, I’m afraid to ask personal questions, for fear of stepping over the line. We are too small to have an HR department. What do I do?

 —Founder of a small company

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Dear Founder,

You’ve identified something that managers and founders routinely face: You don’t know what someone on your team is going through, but you know that something is wrong. You also understand that here’s a fine line between being helpful and supportive and overstepping. Here’s my advice:

  • If you see that something isn’t right, check in and ask. Do this early and often.
  • You can’t meddle, but you can show compassion and care. When you’re worried about stepping over a line, it’s always better to be human and caring than to be perfectly correct.
  • Try and get them the help they need. That could mean taking time off or helping them find and access the appropriate professional resources, which hopefully are covered in your company’s benefit plan.
  • Be aware that serious events can put a team through a collective depression. Determine what resources you can bring to bear to help the rest of the team.
  • Be committed. Make people feel safe to share what they are going through, and when necessary get professional advice from a therapist or counselor so you can be assured you are taking the right steps to help.

As far as whether or not this is any of your business, it is. In order to be productive, your employees must be healthy and happy. Yes, this may not be work-related, but it’s life-related, and it benefits everyone to try to help make everything work holistically. It’s always hard to see anyone go through tough times, but it’s your responsibility to help see them through to the light. There’s so much that’s out of our control, but this one part is in our hands. What we do in these sensitive moments is important.

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