Action & Momentum, Creative Joy, Entrepreneurship

How to Ask for What You Want (without Feeling Awkward)

August 12, 2015

Practically every opportunity that has come about in my business has done so as a result of asking.

When I first started Becoming Who You Are in 2010, I thought that if I just hung around these things would magically fall into my lap. Heh 🙂

As totally misguided as that belief was, it was also a nice belief to have because asking feels uncomfortable. As a kid, I was taught that asking is rude and you should be grateful for what you already have, rather than asking for what you don’t.

A third of that lesson is somewhat true (gratitude never hurts) but it’s taken a long time and some mega-discomfort to re-learn how to ask. I believe in we’re doing here, and over at BWYA, and I want as many people as possible to be able to make use of these ideas and resources. And that means being willing to ask, which is super uncomfortable.

The biggest thing that’ s helped me is approach these asks with high involvement and low attachment.

You need to be involved, go the extra mile, make the effort, but ultimately recognise that whether the other person (or people) says yes is totally not up to you (this is obvious 101 but it’s easy to approach these interactions feeling like we “need” someone to respond with an affirmative—more on that below).

When I go into requests without being attached to a specific outcome, the interaction is a much more pleasant experience. I am often pleasantly surprised by the “yes,” I can be curious about unexpected “no”s (rather than get defensive or complain later about how unreasonable the person is) and ask for feedback or negotiate, if appropriate.

Am I great at asking 100% of the time? Hell no, especially when it comes to negotiation (luckily my husband is much better at recognising opportunities to negotiate and saying so). But asking from this place of high involvement and low attachment feels expansive and filled with possibilities, rather than pressured and needy. Here’s what I’ve learned so far:

Take the “zero pressure” approach

Zero pressure isn’t the same as not caring, it’s just about not being needy, desperate or creepy. I sometimes get emails from people wanting to guest post on BWYA or come on the podcast. When the email is “I have this e-course I want to promote (which is nothing to do with your website) and this is the best opportunity ever for you and something you need to be part of!” it is a super big turnoff. Because it feels desperate and icky. Which brings us to the next point…

Do your homework and be human

Also, show your homework.

While you don’t want to be slimy or insincere, take a minute to let the other person know what you admire or appreciate about them/their work. If you know they’ve been on holiday recently, ask them how it was or say you hope it was a good one. If they’ve been posting on Facebook about how their kid has been sick, wish them well. If they wrote a particular blog post that you love, tell them so. It doesn’t take a minute, but it gets the interaction off to a positive start.

Be enthusiastic

This one is simple but it makes a huge difference. I know that when I’ve been genuinely enthusiastic about making a request (and let that enthusiasm show), the other person has been more likely to say yes—especially when I can communicate why I’m enthusiastic.

Don’t take rejection personally

Having said all of the above, there have been times when I’ve made an ask and received a patronising, dismissive or just downright rude response. Although this stings, I also bear in mind that nine times out of ten, it’s probably not about me or my ask (not to mention the fact that it is super easy to misinterpret the written word without the context of body language or tone of voice).

We never know what’s going on for the person on the other end of the email, phone, or conversation. Maybe they just had an argument with their significant other, maybe they ate a dodgy curry the night before, maybe they just think it’s OK to talk to people like that (it’s not). Either way, there is nothing wrong with making a polite ask, however the other person chooses to respond.

If in doubt, get feedback from other people: was this ask OK? Was there anything I could have done differently? Then get back in the game. The more you ask, the more natural it will feel.

What tips or suggestions do you have for people who are about to make big or scary asks? Share them below!

Image: Breeana Dunbar

How to Ask for What you Want (without feeling awkward). Visit for more posts on reclaiming your creative joy and doing your most important and courageous work.

You Might Also Like

  • Julie Fiandt August 21, 2015 at 2:32 am

    Great post, Hannah! Yes, “high involvement and low attachment” is the perfect phrase for this. Some things that help me are working on my self-talk in advance, reminding myself that awkward feelings or anxiety aren’t signs that I shouldn’t try something, and committing to some small act of self-care or reward afterwards. Thanks for sharing this.

    • Hannah August 26, 2015 at 4:33 pm

      Thanks for sharing Julie! Self-talk in particular is so important. I also love your point that uncomfortable feelings aren’t necessarily a sign that we shouldn’t forge ahead and do something anyway. Truly valuable 🙂

  • Kyla Roma August 21, 2015 at 4:19 pm

    This is such a beautiful post. This is a hard line to walk, and it sounds like you’re doing a beautiful job of it 🙂

    • Hannah August 26, 2015 at 4:35 pm

      Thanks Kyla! I appreciate you taking the time to drop by and share your feedback 🙂