The Art of the Crisp Ask

I have worked for some amazing female bosses. And have had some amazing women mentors. I was reminded of that when I saw this post on Twitter last week:

I thought about one of the best pieces of advice one of my early mentors gave me. Although It took me a while to really grasp its power, it was great advice. I had been trying to decide if I wanted (or needed) to get an MBA (spoiler alert, No). So I went to her with a wishy-washy question about the future, and what she thought, and what if, and how about…and she finally replied, “If you want to do something, ask me a question requiring a Yes or No answer.”  I suddenly realized I had no idea what my question was, so how could she possibly give me an answer? It took me several years to really internalize this lesson, but now I use this concept of the “crisp ask” in many parts of my life and work. 

I’ve often said when I fundraise that many people would love to help—but they need to be told specifically what they can do. My job, therefore, is to lower the barriers between their wallet and my cause. If I can make a “crisp ask”—“Can you send $20 to this address?” or “Can you sponsor my 25-mile run?”—then people can reply Yes or No. And if the response is a clear No, you still have a world of other options. But the harder you make it for people to understand how they can help, the less help they can give you.

When I do business, I've learned that the worst thing you can do is tell people that you can help them do “anything.” Even if they love you madly, they aren’t going to hire you to hang around until something under the vague catchall of “anything” shows up. You have to know your own strengths, package your time and expertise, and tell them about it. And guess what? It turns out that if you can articulate what you do and tell someone how much your expertise will cost, THEY JUST MIGHT BUY IT FROM YOU. Crazy, I know.

And in development, or career planning, articulating a crisp ask, like “I want to manage a team; is there a project I could work on where I can gain experience?” goes a long, long way. People generally do want to help. But first we need to help them help us. Particularly women. I spent a lot of my career thinking, “I’m awesome. I’m sure people will notice I’m awesome and automatically promote me and pay me more money.” Which, as it turned out, hardly ever panned out as I would have liked. But by learning to articulate my value, or at least what I wanted from an interaction or experience, and formulating a clear crisp ask, I could give the people who did think I was awesome a way to help me—by hiring me, or promoting me, or giving me an opportunity.

No matter what part of your life you’re dealing with, never underestimate the art of the crisp ask.