askers & guessers / learning to say 'no' more often

askers & guessers / learning to say 'no' more often

2019, Jul 15    

Prioritising & delegating are hard. I struggle with both. I feel awkward (& even guilty!) saying “no” when someone makes a request of me.

One of the things I’m trying to teach myself at the moment is around saying “no” more often. I work best when I’m focussed on making forward progress on two things, with a handful of operational activities for context-switching satisfaction. Eg if I have two goals for the week plus 4 hours of managing my direct reports, 2 hours of exec- and people-team meetings, 5 hours of interviewing and 2 hours of presentation prep, I’m good. That’s enough.

The more senior my roles have become, the more I’m finding myself with a team who can share the workload, and the more it’s become an ethical imperative to not overcommit either myself or my team.

This is why I take it so seriously when it comes to the endeavour of saying “no” more.

It’s also a piece of leadership advice given regularly. For me, it’s usually been delivered by men who:

  • don’t typically have “office housework” (like taking notes and making coffee and booking meeting rooms) thrust upon them
  • don’t work in “support” functions
  • don’t work in a business function that’s seen as the home of “soft skills”
  • don’t have the same social expectations on them to be endlessly agreeable (else have euphemisms for “bitch” show up in their appraisals)

So you’d think saying no would be more important, justifiable, and internally acceptable as a woman who receives a lot of office housework asks and is the go-to person for things that fall in the bucket of not-my-job for basically the whole org. And yet.

Why is it so hard to say “no” sometimes?

I have a mental model which holds that there are two types of people: Askers and Guessers.

Both types categorise requests received & requests issued symmetrically. Askers assume everyone is an Asker, Guessers assume everyone is a Guesser.

I grew up as a Guesser, which means saying “no” to requests is hard! And I’m trying to become an Asker (which is also hard for different reasons).

Ok cool but what is an Asker??

An Asker is someone who wonders if they can have something, then asks for it, then gets an answer.

1: I’m passing through town next week, can I crash at yours on Friday night?

2: sorry, no, we have my in-laws staying so no space.

1: no worries! Let me know if you’re free for lunch instead otherwise I’ll catch you next time.

Both are Askers, so, it’s simple!

What about Guessers?

As a Guesser, I would love to do the above. But first I must put myself in your place to determine whether my ask is reasonable. Will you think it’s rude? Would I be happy to offer you the same? Are you likely to say yes and actually mean it?

So there’s a heap more internal dialogue and worry and overthinking.

Here’s how the above conversation might play out:

1: hiii how are you?

2: yeah great! Work’s going really well, we’re just back from a vacation too. How about you?

1: yeah all good! I’m actually going to be in town next week if you happen to be around?

2: we’re around, it’d be great to see you. When are you free?

1: oh I can do lunch basically any day and I’m free on Wednesday night too

2: cool, where are you staying?

1: work is putting me up most nights but I’m not sure about Wednesday yet.

2: ah nice, your work are so cool, hope it’s a good hotel!

1: (worries. They haven’t invited me to stay. That probably means I can’t crash at theirs. Best not to ask, that’d be awkward.) yeah I think it is. Any recommendations for Wednesday night?

2: (sends links) we’d invite you to stay but my in-laws are over…

1: oh no of course, wouldn’t dream of putting you out, I’ll check out that link you sent. Thanks so much! (worries. They haven’t suggested a time to meet up, I guess they don’t want to see me.) let me know if you do want to get lunch another day, sounds like you’re really busy though. Bye!!!

Painful, right? Because 1 is a Guesser and 2 is an Asker.

They reach the same outcome but there’s extra stress and awkward and feelings and significantly more messages exchanged. And more cringe for you, reading the imaginary transcript.

If you’re already identifying hard with one of these two types you’ll know what’s coming…

It’s frustrating when we clash

As an Asker, Guessers feel super indirect and waffly. You know they want something, but they won’t just front up and tell you. They take forever to make their request, and take a “no” pretty hard.

Yet it’s even worse the other way around, because the social contract is skewed.

Askers evaluate each request and conclude either yes or no. Guessers take each request with the extra assumption that the person asking has already dismissed obvious objections and concluded that a “yes” is the reasonable outcome here (otherwise why would you ask??!), so it’s hard to say “no” to a request made in this context.

As a Guesser, Askers feel abrasive and make sometimes unreasonable requests - because they haven’t prescreened them (because why should you need to??!)

So now, as someone in a leadership role, you’re told to say “no” more if you want to succeed, and it’s especially hard as a Guesser because it takes some mental effort to overturn the impulse that tells you requests should be ratified or modified. You need to learn, then understand, then teach yourself that a rejection is a completely acceptable outcome.

Managing the clash

I’m afraid I don’t have answers here because I’m slowly training myself to approach life as an Asker. Especially when I know I’m interacting with another Asker.

The relationship, the asymmetry of the social contract around requests, is often much easier to manage when negotiating on behalf of a party that’s not yourself, with a non-human party (eg a contract on behalf of a business you work for, houseshare rental fees for you & your flatmates).

It takes some work, though, when you find yourself engaging with a Guesser while posing as an Asker.

On the receiving end, it’s important to be mindful of the likelihood that the request had been pre-screened. You may need to surface, or even invite, the request. And to soften the “no” so it’s received but the Guesser doesn’t feel rebuffed or refused.

On the requesting end, knowing that a “no” is less forthcoming means prenegotiating or caveating, because the Guesser feels compelled to say “yes” to your presumably reasonable request.

As a leader…

It’s your responsibility to build processes and structures and rhythms that work for both your Askers and your Guessers.

Every company I’ve ever worked for, I’ve pushed hard for a rhythm of proactive pay review so that nobody needs to ask, and nobody is rewarded or penalised for being one type or the other. Same for promotions, feedback, training & recognition. Clear boundaries and policies help Guessers to navigate their own personal internal approval process.

As a manager, I’m doing my best to be an Asker on behalf of my team and an advocate for my Guessers to the rest of the business. I’m also trying to coach both to understand and empathise with the other side.

The hardest thing about saying “no” more often is that it requires you to build a culture where Askers are safe to make requests without being judged as too demanding or arrogant, and Guessers feel safe enough to make their requests and receive a comfortable no.

It would, of course, be easier if we were all Askers, but a large part of being a person, working with people, in organisations made up of people, is examining and understanding tendencies & behaviours and doing our best to level the playing field wherever we can.

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