How To Ask For A Favor From An Old Friend (Without Sounding Insincere)

An acquaintance from college recently asked me to help her with her job transition strategy. We were not close in college, and we’ve not connected in 11 years. Her LinkedIn message popped up to my surprise, and I obliged because she seemed sincere and I love to help.

As we spoke, I shared some advice with her which included how important it is to keep relationships going in the times when you don’t need something, so that in the times like this when you do, it feels more natural. This wasn’t to chastise her, but to help guide her in future interactions.

Since we can’t go back and change the past, I shared some tips for how to warm up cold relationships when one is in a time of need. I realized how frequently this comes up, so I’m sharing these with you:

Be Real and Call It Out

The fastest way to develop depth with someone is to be authentic and vulnerable. In the case of my college acquaintance, I suggested she call out the potential awkwardness of her reaching out seeking help. She could say, “I know it’s been years since we’ve connected, and I take responsibility for that. I hate that our first correspondence since then is my coming to ask for your help, but I hope you’ll allow me some leeway as I’m in a unique transition point and value your…