How do you understand why things are happening slower than you’d like without saying, “What’s holding you up?”

Your team needs to be bringing problems to you, not waiting for you to ask. If you’re pondering this question a lot, it’s time to talk to your team about communication. As a small team, you should be exchanging information constantly: agility is one of your greatest assets, and you need to be aware of each new challenge quickly so you can adapt.

Make sure everyone knows that posting updates about how they’re doing and bottlenecks they run into isn’t wasteful interruption — it’s crucially valuable information that helps you rapidly learn and change course when necessary. At Slack, we created a simple habit around this: when people encounter issues, they post messages that describe what they’re running into, and they prefix their notes with ⚪️, 🔵, or 🔴 depending on the severity, or how badly blocked they are. This gives everyone a quick way to see how things are going as they glance through a channel, and makes it easy to make quick adjustments on the fly.

Rapid communication is a huge advantage over bigger competitors, where information takes time to flow up the chain, and changing course involves big decisions and lots of meetings. You need to play to this strength, and make sure your team understands and appreciates it as an asset.

If you’re thinking about this question a lot, it can also be a warning sign that your team doesn’t know what the priorities are, how they rank, or why they’re important. When someone gets stuck, they’re more likely to speak up if they know the thing they’re working on is a top priority. That needs to go beyond a simple decree — people work hardest when they can explain to themselves, and to their peers, family, and friends how the work they’re doing contributes to the company’s success. Ideally everyone on your team can list the top 3 to 5 things you’re working on, and why they’re in that order. If they know and understand that, they can understand the do-or-die nature of the project they’re working on and are much more likely to speak up when they’re slowed or stuck.

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