Ask vs Guess: The hidden dynamic shaping how we communicate

Nat went treading after work on Monday. By ‘treading’, we mean a bunch of friends trying to stay afloat while catching up on each other’s lives at the local pool.

Sound odd? One nearby kid certainly thought so. This friendly young’un swam over to ask ‘What are you all doing??!’ One hilarious conversation later, and we had the perfect example for this week’s newsie: Kids ask. Openly, boldly and unflinchingly. They ask for what they need without fear of rejection or judgment. It’s truly delightful – unless, of course, what they need is for you to throw out the carefully cooked meal they’ve just labelled ‘disgusting’.

Somewhere along the line, our approach to asking evolves into two distinct styles: Ask or Guess. First popularised by Andrea Donderi on a web forum back in 2007, the concept explains a lot about why we adults often struggle to understand each other: 
 

Askers vs Guessers

Askers believe that ‘no’ is an acceptable answer

Askers assume it’s acceptable to ask for what they need. A request is not a demand, and ‘no’ is a reasonable response. They value clarity over inference and behave as such – asking to borrow your lawnmower, help with a project or to pop over to see your newly completed renovations.
 

Guessers only ask if they’re confident of a ‘yes’ 

Guessers rely heavily on context and cues; they only ask if they’re reasonably certain the answer will be a ‘yes’. Direct requests feel rude and pushy, so they test the waters by dropping hints. Instead of asking to borrow your lawnmower, they’ll comment on their overgrown lawn and hope you offer it up.
 

How this plays out at work

At Powrsuit, we’re fans of clear, direct communication, yet we’re both Guessers. It’s not a flaw – our approach to asking for what we need is shaped by family, culture, and past experiences. Problems only arise when these cultures clash, like in these common scenarios:

A Guesser expects their Asker manager to know they’re drowning. Their manager doesn’t offer support – assuming the Guesser will request help when they need it. 

Because a Guesser doesn’t ask for feedback, their Asker colleague assumes they don’t want it.

A Guesser doesn’t put their hand up for a promotion because they expect to be shoulder-tapped. The Askers in charge assume they don’t want it, or worse, lack ambition. 

An Asker is frustrated that their team don’t jump into the meeting with thoughts, while the Guessers in their team think interrupting is rude.

A Guesser doesn’t ask for time off, professional development budget, or flexibility because they’re not sure they’re allowed to. Their Asker manager is blissfully unaware there’s an issue until they lose a top performer.

In mixed Ask–Guess environments, assumptions can run rampant. We misread each other, assuming our colleagues are disinterested or pushy, underconfident or dominating, when they simply have a different communication style.

Why it matters

Our approach to asking is heavily influenced by social conditioning. Guessers have likely been raised in environments that reward people-pleasing, discourage direct requests, and penalise those who speak up at the ‘wrong’ time or in the ‘wrong’ way. Yes, there’s an obvious correlation to gender.

On the other hand, organisations tend to operate on unspoken Ask-culture assumptions: people who want opportunities will raise their hand, and people who need support will say so. 

You can connect the dots to long-term outcomes. A baked-in Ask culture creates bias about what ambition, confidence, and high performance look like. Great talent is overlooked and often lost, simply because they’re Guessers. 
 

How to bridge the communication divide

Like most communication challenges, the solutions are deceptively simple, but they do require intentional effort:
 

Start by understanding your styles

Share this article with your team and ask them to report back with the culture they most identify with: Ask or Guess. Knowing your different approaches immediately makes it easier for everyone to spot an innocent mismatch in expectations and assume neutral intent. 

Next up, we all need to tweak our behaviour to create a culture that meets in the middle:

It’s not you (or them), it’s dynamics

Even well-intentioned people often misread each other at work. Adapting isn’t about changing who you are, just recognising that we’re wired differently. 

So go find the communication styles of the people you’re surrounded by – you have our explicit permission to ask.