I just finished Jason Gay’s excellent book of advice, “Little Victories”, and in the chapter about work, he touches on something I’ve been thinking about a lot:

“The best bosses share a common characteristic: they are encouragers. It’s easy to be an ass-kicker, to find holes in someone’s professional ability, but good bosses see a flicker of something and just let it barge out the front door.”

Two parts of that quote really spoke to me. The first was the “flicker of something.” In my career, I’ve had a few dozen of those ideas. I’ve had some big, crazy ideas, and I’ve written my fair share of memos trying to prove that my ideas could become a piece of great work. Many of my ideas were outlandish and were justifiably ignored. A handful were too good to ignore. But then there’s this strange middle ground of ideas: ideas that with the right team and a bit of work could become something great, but that could also be dismissed outright.

Which is where the type of boss comes in — because they’ll be the ones that decide which types of work get done. Like Gay wrote, some bosses are “encouragers.” To that, I’ll add the (obvious) second category: “discouragers.”

Encouragers tend to react with support to your ideas. When you’ve got a great idea, they’ll get the resources, talent, and money to make those ideas into great work. But when they hear a half-baked idea, they’ll give you the space and time to turn it into a really good idea. They’ll ask questions to try to draw out the idea. They’ll suggest that you talk with co-workers who might be able to help the idea along, or they’ll pass along a good article or book that might get the idea moving. They’ll give you the benefit of the doubt. Encouragers try to turn a decent idea into a great idea, and a great idea into great work. When you try something and fail, encouragers back you up, share the blame, and don’t let it affect future work.

Discouragers tend to react with skepticism to your ideas. They’ll generally get behind your great ideas, but when it comes to anything less, they’ll try to pick holes in your idea. They’re critics. They’ll ask questions that are intended to find the faults in your pitch. Whatever your idea, you’ll have to prove it and maybe even debate it. You will not get the benefit of the doubt. Every idea has to stand on its own. Discouragers hear a half-baked idea and work to keep it from becoming a fully-baked flop. When you try something and fail, you will take the blame.

I think every boss needs be a bit of an encourager and a discourager — the perfect mix is probably 80/20, with a heavy lean towards encouragement. There certainly are times when it’s important to set boundaries and to say “no.” And when an encourager says “no,” that comes with some credibility, because “no” isn’t their default setting.

In general, I prefer to work with encouragers. When you’ve got a “C+” idea, it’s nice to know that you have a boss and a team that’ll work to turn it into an “A” idea. Working with a discourager is harder. It can feel like you have to reestablish trust with your boss every single day. Sometimes, you shy away pitching anything but your absolute best because you’re afraid of the debate that might come.

With encouragers vs. discouragers, it’s not just about positivity vs. negativity. It’s about support vs. discouragement. It’s about knowing that you have a team behind you, and that you don’t need to prove and reprove yourself.

Jason Gay’s not wrong: The best bosses are encouragers.

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That photo of horses traveling together comes via Unsplash and photographer Susan Yin. There’s a metaphor there somewhere about teams traveling together, maybe? (OK, that’s a stretch. But you get the idea.)

If you’re interviewing for a job on my team, be ready to answer this question: What tools or apps do you use to work?

When I’m hiring, I’m looking for people who are going to be able to work well with my team. If a candidate has the right work habits already, I’m confident that we can teach them the skills and give them the confidence to do great work. So that’s where my question about tools comes in — because the tools you use to work secretly reveal a lot about your work personality.

I’ve learned that:

◦ People who use a to-do app (and there are a million good ones) are typically detail oriented.

◦ People who save lots of links with an app like Evernote, Pinterest, or Delicious usually have lots of big ideas.

◦ People who swear by a calendar app like Google Cal or Sunrise are often very punctual.

◦ People who love an inbox app (Boomerang, Sanebox, Rapportive, Mailbox, etc) are almost always super organized.

This question isn’t everything — I always follow up with more questions about why that person loves an app so much, and what they use it for. But it’s a great way to dig into the mind of a candidate and catch a glimpse of how they work, and that usually gives me a good idea of whether or not they’d be a good fit for my team.

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That photo at top comes via Unsplash and photographer Todd Quackenbush.