The PITA principle, or when should you be a pain in the ass?

Some people report that I am a sweet, nice, and supportive person. Others would say I am a pain in the ass who never backs down. Both are true. Here’s how that works.

I don’t take much on faith.

When my new doctor recently prescribed a medication, I had many, many questions. I was argumentative and difficult. I’ve done my homework and I’m smart enough not to take things at face value.

When I call technical support, I am difficult. I want to know what the reasoning is behind every recommendation. I don’t trust you not to make things worse.

If you’re trying to sell me a dishwasher or a mobile phone plan, I’m going to have the same research-based, implacable outlook. It’s not going to be easy for you.

But I don’t think my wife or my siblings would describe me the same way.

The difference is not just love. It’s trust.

When my wife and I have a disagreement, or one of us is unhappy, the conversations that follows is sensitive and caring and, yes, logical. It’s rare that one of us “gives in.” Instead, we figure out a solution that works, and usually each of us must give a little. I care about our future relationship, but there is more to it than that. I trust her. She is not going to ask for something that’s not in my best interest, or attempt to benefit herself at my expense.

The same has been true recently of my brother and sister. We have challenges that we need to manage together, and we are very different people with very different perspectives. But there is not that much skepticism as we work on our challenges together. The reason, once again, is trust. Once you trust someone, it’s a lot easier to go along with their recommendations without challenging everything.

When to be a pain in the ass at work

Do you trust your boss? Your suppliers? Your customers?

When I was working at companies, there were bosses that I trusted completely, and others about whom I was skeptical. In one instance my boss was the CMO and his stock compensation was listed in public documents. The amount caused me to question whether my own stock compensation was fair. I was difficult and annoying. He told me that stock was a gift and I had no right to question it.

But my stock compensation went up the next year.

Now that I am working freelance, I’ve noticed that I have a different approach to different clients.

I approach most of my clients from a position of trust. If they say they will pay me, I trust that they will. (On many projects I get paid half up front, which makes this level of trust easier.) If they tell me about challenges they have with their management, I believe them. We are generally operating from a position of shared intent — they want to improve, I want them to improve.

I certainly put contracts in place, because they make sense in any business relationship — they help to define the parameters that the trust is built around.

And I am rarely argumentative, difficult, or a pain in the ass.

On the other hand, I sometimes must deal with these clients’ procurement departments. I have no reason to trust these folks, and they frequently cause problems by paying late, asking for pointless extra work, and attempting to force absurd contract terms on me.

Recently, a large social network who wanted my help attempted to require me to accept a clause that said I would not hire or contract with any of their employees, contractors, suppliers, or customers, a group that would have included tens of millions of individuals. I asked them to delete this absurd clause, and I was not nice about it, either. Why not? Because such a request violates trust at the outset, and if you prove to me that I cannot trust you, I’m going to be a pain in the ass.

Call it the PITA Principle: only be a pain-in-the-ass to people you can’t trust.

As you go about your work, consider this distinction.

There are people who will always go along and get along. They will get taken advantage of frequently, and are unlikely to become leaders. Not only that, they’ll suffer work-related anxiety and frustration for their whole careers.

There are people who will be difficult at all times. They will become known as a pain-in-the-ass types. They won’t get far, either, because they’ll rapidly be perceived as “not a team player.”

And then there are people who will go to the mat for those who they can trust, and challenge those who they can’t. People like that can often create positive change or block stupidity. You don’t need to be mean. You don’t need to be angry. You just need to ask questions and not back down. (If you want to keep working there, it’s often better to do this privately, rather than in front of a group, because embarrassing people is not the goal — getting things right is.)

I have one last question for you.

In your dealings with the people you work with, the people you work for, and the people who work for you, do you behave like someone who is worthy of absolute trust?

If not, that may explain why the people around you are so often behaving like a pain in the ass.

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