When You Should Go Behind Your Boss’s Back

At HotelTonight, I’m a big fan of the maxim “ask for forgiveness not permission.” I believe it means the team is moving quickly and confidently, taking chances and not being afraid to break things. However, there’s obviously a time and a place to ask before taking action, and I’d never advocate doing anything that would be disrespectful or violate your manager’s trust or cause irreparable harm. Those caveats aside, here’s when I think it makes sense to make a call without running it up to your manager first.

When the wheels are about to come off

When a problem arises, sometimes you need to take immediate action to right the ship. Stopping to ask your manager’s permission could lose you valuable time. Case in point: we’ve been launching a bunch of new HotelTonight features recently, and on an especially busy weekend, one of our Product Managers noticed that volume was so high it was slamming our Customer Experience team with inbound questions (admittedly, too many bookings is a high class problem!). So she turned off the feature in a few cities, sent a note to her manager (who was in a car on the way to Tahoe) and made the weekend way more bearable for our hard-working CX team. And we learned what we needed to do differently the next weekend. (Nice work, Graciela!)

When the risk is self contained

I encourage my team to take risks, especially when they’re self-contained – meaning that if they fail, there won’t be major fallout. For example, our Head of User Acquisition, Brian, recently spotted a great opportunity with a new marketing partner. By coming to me before testing the channel, it would have slowed down the process. But he knew the risk was small and contained compared to the potential reward. So he made the call and forged forward, and was able to get the channel launched quickly. It turned out to be a major win that yielded stellar results. (High-five, Brian!)

When your boss empowers you to

I don’t need – or want – to be involved in every decision my team makes. Few things make me happier than hearing about a huge win for the first time after it has been implemented. I encourage other managers at HotelTonight to manage their teams in the same way. We hire smart people who are self-starters and empower them to take chances and make independent decisions – even if those aren’t the exact decisions their managers would make. Sometimes this leads to big wins, and sometimes those chances don’t pay off, but everyone learns from the experience. (And there’s always our infamous Vest of Shame for spectacular failures.)

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If you’re hung up on always asking for permission, it bars you from moving quickly. As long as you’re respectful and weigh the risk vs. reward, take those chances! A smart manager will respect your initiative.