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


When I first started Becoming Who You Are, I thought that if I just hung around, things like interviews, guest posts, speaking gigs, and opportunities like The Entrepreneur’s Inner World 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 what I'm doing here, 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 same thing applies to relationships. I need help, support, and to make requests sometimes and learning to ask for this has been necessary to maintaining my physical and emotional wellbeing. Being able to ask for and receive help, advice, support, love, etc. makes me a better partner, mother, and overall person.

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

We 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 us (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? Definitely not, 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 acknowledging the other person has their own values, priorities, commitments and perspective that might not match ours. Like I mentioned above, whether or not the other person says "yes" to our request isn't under our control. I don't know about you, but times when I've been on the receiving end of a pressured ask where it feels like I just.have. to. say. yes. are not feel-good times.

However urgent it might feel in the moment, we don't usually need the other person to agree to our request for everything to be OK. In negotiation theory, there is something called a "Best Alternative to Negotiated Agreement" (BATNA), which is a fancy way of saying "other options we can try." In most situations, there will be a Plan B, C, D, etc. we can fall back on if the person says no. Having your BATNA in mind before you make any ask will not only take the pressure off you, but also the other person too.

Connect and Be Human

While we don’t want to be slimy or insincere, taking a brief moment to connect with the other person first before launching into a request can make all the difference.

In a professional context, this might look like letting the other person know what you admire or appreciate about them/their work. If they wrote a particular blog post or worked on a specific project that you love, tell them so. On a personal level, if you know someone has 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, check in with how things are going and wish them well. It doesn’t take a minute, but it gets the interaction off to a positive start.

Show Your Enthusiasm

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.

When we feel nervous about asking for what we want, sometimes this come through as indifference, pressure (see above), or a blunt approach that verges on rudeness. But if we can explain why something matters to us and—if relevant—the benefits to the other person too, the energy of the ask changes.

Reframe Rejection

There have been times when I’ve asked for something I want and received a response that seems patronising, dismissive or downright rude. Although this stings, nine times out of ten, it’s probably not about me or my request (not to mention the fact that when this happens via email 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're experiencing the after-effects of a dodgy curry they ate the night before, maybe they just think it’s OK to talk to people like that. 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! 

Photo by Camylla Battani on Unsplash