Stop feeling like a kid every time you ask a day off

1 minute read

Most companies don’t have unlimited vacations. Most likely, if you are an employee, your days off need to be validated by your boss. If you are like me, this feels like pulling teeth … Every time I have to ask for a day off, I feel like a kid asking for an extra candy

That’s not the only issue with how we traditionally deal with vacations :

  • The boss has to make sure that there are always enough people at the office to handle emergencies
  • If the boss is himself away, getting a day off at the last moment becomes difficult

Our Delegation Board

Our team at work is already rather agile : we’re using a blend of XP and Scrumban, we follow solid engineering practices and we are always trying to improve to deliver more value to our users. After reading Management 3.0 and Management Workouts I was convinced that I needed to move the team towards even more self organization.

We started by doing delegation poker, we created a delegation board, and set out to move all cards we could to the right side of the board.

Our trello delegation board

We spotted the following topics that could be more self organized

  • vacations
  • hiring
  • business objectives and end of year evaluations
  • various recurring scrum related activities
  • self development objectives


We decided to tackle vacations first, because it seemed easy. We did a quick brainstorming, and here is what we came up with :

  • We cannot change the company policy, so I’ll still have to officially validate everyone’s vacations in the system but …
  • I’ll validate anything asked !
  • Our internal system allows to check the other team member’s vacations, so everyone in the team is responsible to check that there will always be at least 2 people at work before taking a day off

Screenshot of our vacation dashboard

It’s been 6 months, and it’s been working like a charm. I think it made everything simpler once we had a clear rule about when vacations were OK or not.

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