How *NOT* to Ask for a Favor

Recently my old boss contacted me on LinkedIn.

We aren’t Facebook friends, though he is friends with my former colleagues who also reported to him. I never thought he really clicked with me. It made me feel a little left out, but not everyone is going to click with everyone. It's okay.

However, when I got a message from him on LinkedIn asking me how I was doing, I was pleasantly surprised!

I was like, “Oh my gosh! How nice! Former Boss wants to reach out and see how I am! Maybe he did like me more than I thought! Maybe my perception was wrong!”

I wrote him back a nice and friendly message thanking him for reaching out and genuinely asking him about how he was doing.

But you know what? My perception wasn't wrong. Of course it wasn't. 

I am very perceptive.

His response back?

A pitch.


No, he didn't care at all about how I am. He just wanted to contact me so he could pitch me so that I can use my connections at the Fortune 500 company where I work to help him get business for his new employer.  

He made me feel stupid for thinking that he was actually interested in how I was.

It was insulting.

It certainly didn't make me want to help him. And I love helping people!

Yeah, that's pretty much exactly how NOT to ask for a favor.

You don't ask for favors by being disingenuous, basing them on false pretenses, making people feel that you don't think they are smart enough to see right through what you are doing.

This is how you ask for a favor:

With people you already know, first, you put time and effort into relationship building. You check in with them, demonstrating that you are actually interested in them. This can be as simple as just liking their posts on Facebook or Instagram. It really doesn’t even have to be that time consuming.

Once you have done that, then you can approach someone and ask for a favor. Be straightforward about it and keep it simple, “Hi! I hope you are doing well! I was wondering if you could help me with xyz.”

People will be a lot more likely to help you if they remember how you have extended yourself to them.

Is it okay to reach out to someone you don't know and ask for a favor or a connection? Yes, of course it is. We have networks for a reason so asking for a favor or pitching someone in your network is fine. Just be straightforward about it.

That is it. It is as simple as that. Be genuine. Don’t make people feel like you think they are stupid. And don’t pretend to care about someone when you don’t. It is okay not to care! We don’t have time to care about everyone. 

So how did I respond to my former boss, whose opinion of me I don't have to worry about anymore?

Straightforwardly, of course: 

“Oh, and I thought you were actually interested in how I was doing.”

What do you think his response was? Did he take ownership for his bad tactic?


He told me “Don’t be silly.”

My response to that?


Do you have any advice on how to ask for favors? What would you have done in this situation? Tell me in the comments!

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