How to Discipline Your Boss

I’m pretty lucky. I have a really awesome boss. We get along beautifully, and we’re building a company that’s pretty special. But here’s the thing: Lorraine’s only human. And it’s kinda lonely at the top–there’s no executive board or governing council to give her feedback on how she’s doing or offer room for improvement. Sometimes she needs help. So I try to.

Some people might think it’s weird to have a 24-year-old like me giving advice to (or lecture or badger) my ever-so-slightly older boss. They might think it’s even weirder that she listens to me sometimes. But it’s because we both passionately care about our web design and social media business and want to see it grow and change and evolve every day–and that means that we have to grow and change and evolve, too.

For those of you who have bosses cool enough to realize they aren’t perfect, who always want to get better, here are a few tips for disciplining your boss:

  • Keep emotions out of it. This can be interpreted a couple of different ways. Sometimes before offering criticism, you need to take a step back, take a few deep breaths and think logically. If I’m going to Lorraine with something I feel is very important, I take the time to gather my thoughts and jot a few notes so I can present an orderly case for what I think needs changed. Other times, we might get into an impromptu sparring match. Yelling might ensue. But no matter how heated the argument, we both still walk away friends. The argument wasn’t about us as people, but about how we can be better. Don’t let conversations devolve into personal attacks–keep the focus on what’s best for the business.
  • Pick your battles. Some of you may know that Lorraine is a little typo-prone. She’d be the first to admit it. And as a copywriter, it drives me nuts. I could choose to harangue her about each finger slip in a blog post or a tweet, but does that serve a bigger purpose? No. So I quietly fix the little stuff, so when I come to her with something bigger–like transitioning @roundpeg from a personal account to a dedicated business account–she listens. You won’t win every battle, so pick the ones that are important.
  • Be prepared to lose. Even when picking your battles, sometimes, your boss won’t listen to you. If you have a good boss, she’ll explain why she can’t take that suggestion. After all, there might be pieces of the puzzle that you can’t see from where you’re standing, but that fit into a greater design. But when you don’t get everything you want, don’t take it personally, and don’t give up.
  • Fight with love. Some days, it would be a lot easier for me to just keep my mouth shut than to gear up for another conversation with my boss. And some days it would be a lot easier for her to tell me to shut up and go back to work and let her run the business. But no matter how bad our day is going, both Lorraine and I love what we do and love Roundpeg and believe in its promise. And that’s why we don’t take the easy route. Whatever you say to your boss, make sure you’re motivated by what will further the goals of the organization, not what will make life easier for you personally. The two can coincide, but don’t always.
Sometimes, even good bosses need a smack in the head. If you deliver it in the right way, it can be a positive experience for you, them and the company as a whole. Do you discipline your boss?