It's Easier to Ask for Forgiveness

“I aim to misbehave.” Captain Malcolm Reynolds, as played by Nathan Fillion, Serenity

Sometimes being a leader means breaking the rules. I’m not suggesting that you just wholesale ignore the rules and consistently defy those above you… But as a leader there will likely be times when you’re going to have to be willing stand up and use your better judgement despite what you know your boss might want you to do.

Rear Admiral Grace Hopper put it perfectly when she said, “It’s easier to ask for forgiveness than permission.” And I couldn’t agree with her more. Your goal as a leader, at least in my humble opinion, is to give your team the autonomy to make their own decisions and not have to seek forgiveness if it goes haywire. It should be automatically granted, but hey, that’s a whole different lesson.

Today I want to focus not on your role as a leader but instead your role as a subordinate to someone else. In pretty much every position you have in your career, you are going to have a boss. Your relationship with that person or persons is going to be key to your success and going directly against their orders can potentially do great harm to that relationship. So that said, approach some of this with caution.

Sometimes you will find yourself in what we will call the gray area. This is exactly what the admiral explained to us above. Here’s an example: You’ve been presented with a decision and you know what your boss would likely tell you to do if you asked for their direction. Yet, you firmly believe in your expertise, history, and your gut, that the best option is likely the opposite. Living in this gray area, you make the call you think is best, presenting it to your boss only after the fact, with your reasoning for making the decision.

In this scenario, you likely aren’t telling your boss, “I know you would have told me to do the opposite.” Instead you find yourself explaining that with the information you were given, you made what you believed to be the absolute best choice.

Will that explanation work? It depends on the situation and on your boss. Obviously, it’s up to you to determine ahead of time what you believe the risks are in that situation and whether or not they are acceptable to you. In my career, I have had bosses where I felt very comfortable leveraging the gray area because I knew in the end they trusted my judgement and had my back. I have also had bosses where they expected me to run every idea and decision by them. My first choice is of course having a boss that trusts you — because it can make all the difference in the world for your happiness. But obviously, we don’t always get to choose our bosses.

So what do you do when stuck in a situation where you think there will be severe consequences for making a decision that you know your boss wouldn’t choose? I’m going to be honest and tell you that I’m not willing to give you concrete direction here and say you “should” do this our you “shouldn’t” do that. In situations like this, there are so many variables that I cannot accurately predict what is the right choice. Instead, let’s discuss four questions that might help you make the decision you believe to be correct.

What’s at stake? - What happens if you just bring the decision to your boss and let them tell you how to proceed? How concerned are you about not pursuing what you believe to be the correct course of action?

What are you risking? - What will likely be the scenario if you decide to move forward and defy what you believe to be your boss’ wishes? Will it be a non-issue, a slap on the wrist or something much worse?

Is this a deal breaker? - Outside of your answers to the first two questions, ask yourself if this is an issue where you feel you must take a stand? Is this an ethical decision where you believe not pursuing your course of action would go against your closely held beliefs?

What will these mean for others? - Will taking your course of action — even if aligns to closely held beliefs — hurt others?

After answering these questions, it will hopefully become more clear to you what you feel you need to do. From there, you just have to take action and see where it leads you.

Remember that even when you are working in that gray area, you should always be as respectful as possible in your actions. Not doing so can turn your boss’ attitude on the situation from merely annoyed to career limiting. And as I have mentioned before, when you’re in a leadership position, it is extremely important that we are respectful of others even when we disagree with them.

I hope this blog has been of some help to you regarding how to make the call you feel is right and then take action even when it’s difficult. Now get out there and try it out… it’s your turn now.

-Jason

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Jason Slingerland