Five Things that Make Asking Easier


Lately, there are so many areas of my life where, if I want to move forward, I need to ask others to join me. It doesn’t seem like asking should be that hard. Just a quick conversation or a few sentences in an email.

But my mind comes up with a million reasons why I shouldn’t ask…

I’ll be annoying them.

I’ll be obligating them into something they don’t want to do.

They’ll think I think too much of myself.

Or too little.

They’re just going to say “no” anyway so why waste their time.

They’ll say “yes” and then I won’t have an excuse for not following through on the thing I want to try…

All these doubts and reasons aren’t necessarily true and they certainly don’t mean I shouldn’t ask. Just because a part of me is terrified of taking any risks, doesn’t mean the risks aren’t worth taking.

Over the past few months I’ve been working with my coach on asking, whether it’s asking someone for feedback, asking people to work with me as their coach, or asking other bloggers to join me in a writing group. Through these experiences I’ve been learning things that help make asking a little easier.

If I’m experiencing something, I’m probably not the only one.

It’s so easy for us to feel alone in our discomfort. We look around and imagine everyone else has it all together and has all the friends they’ll ever need. But it’s often the very struggles I think I have to face alone that can be my greatest point of connection with someone else.

If I’m wishing for something, chances are good that others are hoping for the same thing. Maybe we’re all waiting for someone to be brave enough to ask. It’s easier for me to do the asking when I believe others are waiting too.

Minimize the time between deciding and asking.

I don’t know about you, but I tend to avoid doing things that make me uncomfortable. Even after planning to start a writing group and deciding who I’d ask first, I still put off asking for weeks. I’d say I needed just a little more time to figure out what I wanted to say and make sure I was doing the right thing, always promising myself I’d do it tomorrow for sure.

But longer I delayed asking, the more space the situation took up in my thoughts. Instead of making things easier, waiting actually took up a lot more energy and made asking feel even scarier. When I finally followed through, I felt such a huge sense of a relief and then wondered why I didn’t do it sooner. I could have avoided all the anxiety and energy drain that came with procrastinating.

The only way it becomes easier to ask is to ask a lot and ask often.

When we ask something only rarely, each question and each response carries a lot of weight. If I only ask two people, a single “no” already guarantees a 50 percent refusal rate. On the other hand, if I often ask people to try things out with me, each response feels like less of a big deal.

My coach introduced me to The No Game. The idea is to try to collect as many “no"s as possible. Making “no” a goal instead of a thing to avoid takes some of the sting out of getting turned down. Additionally, in order to collect a lot of “no"s I need to ask a lot…which increases my chances of hearing a “yes.”

I am not responsible for anyone else’s decision.

It might feel like I’m being helpful when I don’t ask because I don’t want want to make someone have to tell me “no” or pressure them into agreeing to something they don’t want. Actually, in assuming I know how they will respond, what I’m really doing is denying them the opportunity to make their own decision.

In reality, I don’t know for sure what they want. It’s true that some people might give me a “yes” when they really mean “no,” but that isn’t something I can control. What I am responsible for is asking in a way that is a request not a demand.

Someone saying “no” isn’t necessarily personal.

It might just mean that what I’m asking isn’t a good fit for them right now. In fact, someone saying “no” can actually be a good thing. It makes space for someone else who really wants what I’m offering.

One of the people I asked about joining our writing group declined the invitation because she already has all the close writing community she needs right now. That “no” wasn’t about me. Instead, it was about her knowing what she needs and how much time and energy she has to devote to connecting with other writers. Rather than adding another commitment to her already busy schedule, she’s leaving space in our group for someone who is hungry for more connection.

How about you? What would you love to ask someone to join you in trying? What are the fears and excuses getting in your way? Have you learned anything that makes it easier to ask?