If you don't ask...
Unpacking the common mistakes we make when asking for what we need and want, and what to do about them
“Have you asked?”
When I hear a client grumbling about something that hasn’t happened, that someone hasn’t done for them, or where their needs and wants haven’t been considered, this is often the first question I ask them.
Sometimes the answer is no. Cue silence from me and a sheepish look from my client.
Sometimes the answer is yes, but when we unpack it a little further the ask has been weak, or unclear, or had other issues that makes it entirely unsurprising that they didn’t get what they wanted.
So let’s take at a few of the common mistakes we make, and some tips on how to ask more effectively.
Because if you don’t ask, the answer is already no.
What we get wrong and what to do about it
One. Not asking.
Yes, it’s obvious. And unless the other person’s psychic abilities are really on point, then if you don’t ask, you won’t get. Stop assuming the other person knows, or will guess, or figure out what you want. The chances are they won’t, as the reality is we think much more about ourselves than we do about others (that’s not a criticism, just a reality).
What to do…
Yup, it’s the blindingly obvious answer. Just ask. Be confident, be bold, take a deep breath, and make the ask. In the majority of cases the worst case scenario is a no or a non-response, in which case you’ve lost nothing. The best case scenario is that you get the thing that you want and need. So what are you waiting for?
Two. Being vague.
When our ask isn’t clear, we significantly reduce the chances we will get it. A vague ask requires the other person to do a lot of work to figure out what it really is that we want. Which, ironically, makes the ask itself that much bigger and more complex (even if what you want is small and/or simple). It also increases the chance they will misunderstand what you want, give you the wrong thing, or simply avoid it either from being unwilling to put the effort in to understand or from a fear of getting it wrong.
What to do…
First, get clear on what you’re actually asking for. Often this is the cause of the vagueness, as we haven’t put the time in to think it through.
Then, think about how to phrase that ask clearly. For most people, it’s best to err on the side of being brief and direct. Couching an ask inside a lot of other information and justification is mostly for our own benefit, to try and feel less uncomfortable, and doesn’t help the other person. As Brene Brown put it, “Clear Is Kind. Unclear Is Unkind.”.

Three. Only asking once.
Many of us stop after asking a single time. We assume that if we didn’t get a yes to that, it must be a no. When in fact it’s equally possible that the request was missed, got buried in someone’s inbox, or arrived at an inconvenient time and has simply been forgotten about. Or perhaps they just needed some time to think about it. Either way, assuming a non-reply is a no is an unhelpful assumption to make.
What to do…
Keep going. Don’t be afraid to follow up, perhaps multiple times. This isn’t about becoming a p.i.t.a. but about being persistent. Like it or not, your ask is probably not the other person’s top priority, thus being willing to follow up significantly increases the chances of your ask being fulfilled.
Four. Confusing requests and demands.
If something is truly a request, that means we are happy to receive a yes, a no, or a counter-offer in response. In contrast, a demand is something where we have a need and expectation that the answer is yes.
Often, in our efforts to be polite, and (particularly for women) in an attempt to not come across as aggressive or bossy, our demands sound like requests. Then, when we receive a no (or a non-answer) we feel frustrated and rejected by the other person, when in reality, that’s on us.
What to do…
Before you make the ask, get clear on whether your ask is a request or a demand. If the latter, think about how to phrase it in such a way that that is clear to the other person. So instead of “Would you be able to help me with this?” try “I need your help with this, when can we schedule a chat to run through what needs to be done?”. We can still be kind and polite while making demands, and it saves time and stress later on if we are clear upfront.
Five. Stop making assumptions.
You know when you make an ask, but you’ve already decided the other person will say no, so you almost talk yourself out of the ask after making it? That. It’s a normal fear of rejection that we’re seeking to protect ourselves from.
I used to do it with prospective coaching clients. I’d share my rates, but before they had a chance to respond I’d launch into a spiel about how if they were too expensive I’d offer a discount! Stop assuming how the other person will respond, it will get in the way of you making the ask in the first place, and will definitely stop it being a clear and powerful request.
What to do…
First, challenge your assumptions. Notice the response you’re expecting, and allow yourself to be with the possibility of a wide range of answers, including a resounding yes.
Then, allow the pause. Once you’ve made the ask, leave space for a response. That might mean a few moments of uncomfortable silence, or a few days awaiting a reply, but be patient. Don’t leap in to fill that space with a retraction, or an apology for asking, or a watering down of what you want. Allow space for a reply before you dive in.
So, what are your habits around asking? Do any of these mistakes resonate as something you’ve done? What are you willing to try to improve your asks? Leave a comment and start the conversation below.
If you’d like to dive into this in more detail, this is an excellent article on Medium on The Art of Asking.
And finally…
As a Brit, I think we almost take pride in our ability to say something without actually saying something. These are some lovely examples 🙂
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