The Art of the Ask

“Ask and ye shall receive”…well, sometimes yes and sometimes no. It’s the HOW, WHO and WHAT you ask that will impact the outcome. One of the critical components of my Board of Your Life program is the participation of a willing and open Advisory Board. This fact can often be a non-starter for people considering the program but who cannot fathom asking people to “give up” three hours of their lives to help them suss out new possibilities and directions. Invariably, this often morphs into a discussion point for our coaching. Think about it. Do you have a hard time saying “no” to others, but find it hard to ask for “favours” yourself? You are in very good company.

I’ve become a bit of an aficionado on the topic. Have had to. When I started my business, I knew precious little about precious little businesses. I would have starved had I not heeded some good advice: “ask people for help”. Here’s what I’ve learned about asking:

How to ask

  • Nicely. Very very nicely.

  • Reciprocity – make sure that there is something in your request for the askee…or that you’d be willing to return the favour. Preparation is key…what might they value? Is it your expertise in a given area? Is it a nice meal out in return for some advice?

  • Clarity – Make the expectations crystal clear so your potential benefactor is aware what the commitment is (time or otherwise). No one wants to have to read between the lines.

Whom to ask

  • You should have some modicum of assurance that this person is amenable to you, your situation or your request. They may know you or know OF you. While I have written about the kindness of strangers, it's also true that most people are more inclined to help someone if the introduction is warmed up. (Case in point, I have agreed to mentor a young woman who I had never met because the request was made through someone I respect and admire.) Reason #213 for expanding your network and deepening your relationships.

What to ask

  • People are inherently good and want to help. It is a belief that I hold dear. So, please…don’t be a jerkbag and ruin that for the rest of us. Make sure the ask is reasonable – if it’s selfish or ridiculous, they will not forgive you and you’ve slammed that door shut. What is “reasonable” can be subject to interpretation. So I recommend you turn it on its heels…if you were asked the same (or parallel), how would the request make you feel? What would it elicit in you? Would it make you feel honoured or like a sucker. If you’d feel even kind of squeamish, I beg of you: DO NOT MAKE THE REQUEST!!!

  • While people are kind and generous, they are also very busy and their time is in demand at every turn. Make it easy for them to say yes, and they just might.

And once it’s all wrapped up and in the bag, please, please, PLEASE find a way to show your gratitude for their gift of time, expertise or even trust. For me it’s sending a thank you card. Old-fashioned AND appreciated. Am not a big birthday card sender, but I am a believer in a heartfelt, hand written thank you note…with stamp. Because, as Danielle likes to say, “e-cards suck and everybody knows it”.

And finally, IF your clear, reasonable, sincere, respectful, and sensible request was turned down, PLEASE don't take it to heart, or as a sign that you are not worthy. It may well tell you more about the person you’ve approached than about yourself (they may be stingy with their time OR dealing with a family crisis…you may never know). Regroup, retool and get back on that horse…your artful ask will soon find the right patron.


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Tanya