Are you an asker or a guesser?
Have you heard about the "askers" vs. "guessers" framework? A friend recently shared an article about it, and I feel like so. much. made. sense. when I read it.
It was published 15 years ago, but I’d never heard of it before. If you're also new to the concept of “Askers” and “Guessers”, here’s the short version:
Askers grow up in environments where it’s normal to ask directly for what you want.
“Can I stay over?”
“Can I borrow your car?”
“Can you help me with this?”
A no might sting, but it’s not a rupture. Asking is neutral.
Guessers, on the other hand, learn to read the room first.
They scan for cues.
They only ask if they’re already pretty sure the answer will be yes.
Because asking — and being told no — feels risky, awkward, or relationally unsafe.
Neither is better.
But oh wow, does this difference show up in business.
Once I saw it, I couldn’t unsee it.
If you’re a Guesser (and many sensitive, intuitive, socially attuned people are), you might recognize yourself here:
– You hesitate to talk about your offer unless you’re sure someone wants it
– You soften your prices or over-explain so you don’t make anyone uncomfortable
– You wait for invitations instead of initiating conversations
– You feel vaguely anxious about “being salesy,” even when you know your work helps people
– You tell yourself you’re being considerate… but secretly wish people would just ask you how to work with you
This all boils down to relational safety.
If you learned that asking could disrupt connection, of course you learned to guess instead. Of course you learned to be subtle. Of course visibility feels charged.
But entrepreneurship — whether we like it or not — requires asking.
Asking people to consider your work.
Asking to be paid.
Asking to be seen.
Asking to take up space.
Which means that for Guessers, business isn’t just about strategy.
It’s about rewiring what feels safe.
This is why I don’t teach visibility or sales as a performative skill.
I teach it as a relational practice.
One where:
– Asking doesn’t mean attachment
– A no doesn’t mean rejection
– Being clear doesn’t mean being pushy
– And offering your work is an act of service, not imposition
Inside my work, I often say this:
“Your job isn’t to convince. Your job is to invite.”
Invitations are clean.
They respect autonomy.
They allow room for choice.
And when you build a business that way — slowly, honestly, with nervous-system awareness — you don’t have to become someone you’re not.
You just have to stop hiding.
If you’re noticing yourself in this, here are a few gentle questions to sit with:
– Where in your business are you guessing instead of asking?
– What do you assume people will think if you’re more direct?
– What would it feel like to let a “no” be neutral — not personal?
– What kind of support would help you practice asking in a way that feels safe?
This is the work beneath the work.
And it’s why so many talented, ethical, deeply capable entrepreneurs feel stuck — not because they lack skill, but because their system is protecting connection.
If you’re an Asker, this might help you understand why some clients hesitate.
If you’re a Guesser, I hope this helps you be gentler with yourself.
Nothing is wrong with you.
You’re just learning a new language.
And like any language, it gets easier with practice — especially when you’re not doing it alone.
P.s. If you’d like to expand your comfort with visibility in a way that feels safe and authentic to you, my 30-Day Visibility Accelerator is just the thing. Here’s your official invitation.
Look at me, asking. 😉
