Easy way to screw up leadership in your team

Let’s start with a hypothetical situation. You are one day working as always and one of your direct reports needs to talk. Let’s assume you drop everything and can jump into a call. Your teammate needs some help: he applied to a conference and needs some day off to attend. This should be an easy one, conferences are fun and people always learn in conferences (this blogpost can also apply to a medical procedure or something similar). There is a trick, your project and your client (could be internal/external) might be impacted by this decision. Maybe there is not a lot of runway to make the decision.

What do you do now? The easy way is: “Sorry, we can’t do it this time. There is an important deadline/deliverable and we need you to reach it”. This is the easiest way out, you don’t need to talk with the client and there is always a conference next year. Maybe next year planets will align?

There is another way. You say: “I got your back. This conference is important, is a great opportunity and I will fight whoever I need to fight for you to take the days”. How confident you sound and how much you can promise will depend on your position in the organization and how much influence do you have. Sometimes you might need to say: give me some time and I’ll try my best. But what you need to do after that is fight with all that you have for him. Think about creative ways to reach the goal, maybe some overtime before the conference or maybe the whole team can help. 

The result is important but it is not everything. What matters is how you communicate and that your teammate feels that you are on his side. This can make or break a relationship. In tech job markets are always hot, you will not be able to always compete in salary but these little details can make the difference. 

Also there is something way worse you can do. Please never do this. You can blame the teammate. It’s sad but I’ve seen it in the past. Sometimes managers say: “Why did you do this? If I bring this up it can bring a lot of trouble. This is a big headache“. Please don’t do it. At least try to get the days for your teammate. 

How would you handle this situation? Have you had different experiences?