103. Is it your job to tell your boss when you think they’re wrong?

In this scenario there are two types of people in the world:

1. Those who simply do whatever their boss says
2. Those who don’t

Of course there are some sub-categories in each of these but this is the first level classification.

If you simply do what your boss says then:

1. You can absolve yourself of any responsibility if things go wrong
2. You don’t upset your boss by challenging them
3. Life will be easier
4. You may receive the blame anyway
5. It can be a very frustrating existence

If you don’t simply do what your boss says then:

1. You may clash heads with you boss on occasions
2. Life will be a little bit more exciting
3. You will add value to your organisation and shine
4. You grow
5. You risk failure

I generally fall into the second category. One of my mentors once told me that:

If you always agree with me then only one of us is thinking

The important thing is to do it with respect and to pick your battles.

1. Don’t outright tell your boss that they’re wrong. Simply ask the right questions and offer alternative options. Have an adult discussion about it and don’t allow yourself to become emotional.
2. There is no point fighting every small thing. Learn to focus on the important things and to let the minor things go.

This can also work against terrible bosses. Those who a mini-dictators who take everything personally. It’s all about how you approach the challenge.