Askers vs Guessers in Finance: Askers are Annoying, Rich

Any follower of @Real_Interloper is aware of my fixation on the issue of Extroverted versus Introverted personality types and the possibility that Introverts will be devalued in a service-based, technology-heavy economy. * There is a subset of this discussion which relates closely to relative success in the financial industry – Askers versus Guessers – which is helpful in understanding the frequent annoyances experienced by clients and prospective clients of investment banks.

The popularization of the Asker/Guesser Paradigm began with a blog post by Andrea Donderi quoted by the Guardian HERE:

We are raised, the theory runs, in one of two cultures. In Ask culture, people grow up believing they can ask for anything – a favour, a pay rise– fully realising the answer may be no. In Guess culture, by contrast, you avoid “putting a request into words unless you’re pretty sure the answer will be yes… A key skill is putting out delicate feelers. If you do this with enough subtlety, you won’t have to make the request directly; you’ll get an offer.

The most obvious general manifestation of Asker/Guesser are the dudes that internalize the dating scene as a numbers game, and will spend an entire night at a bar getting shot down until some definition of success is achieved. The necessary psychological equipment for this practice is incredibly thick skin, an ability to soldier through mass rejection that would emotionally cripple a Guesser.

The stereotypical retail broker is virtually the Platonic ideal of the Asker. Successful brokers are often immune to rejection, criticism or introspection.  To provide a specific example, I was once involved with a merger where the retail wing of one company combined with the capital markets department of another. About a month in, a broker sent an email to all capital markets staff informing them that they would be required to switch all of their investment accounts into the new retail division, and since this was the case, they might as well sign up with him.  No such policy was ever discussed or established. When confronted, the broker just said, “Oh, sorry, I must have made a mistake” and went on with his daily routine.  Didn’t work, on to the next.

Not everyone employed in finance is an Asker and self-doubting Guessers are particularly prominent among strategists and economists.  Askers however, particularly in their most subtle form of investment bankers, tend to make the bulk of the money. This makes sense in that the asking is generally for money, and Askers rightly demand their cut.

The Asker/Guesser dichotomy operates on a continuum – very few people are 100% oriented either way. However, the differences are so fundamental that communication between the two groups is often fraught with danger. The Guardian article describes this well:

An Asker won’t think it’s rude to request two weeks in your spare room, but a Guess culture person will hear it as presumptuous and resent the agony involved in saying no. Your boss, asking for a project to be finished early, may be an overdemanding boor – or just an Asker, who’s assuming you might decline. If you’re a Guesser, you’ll hear it as an expectation.

I suspect that Asker/Guesser issues form a significant part of anti-finance sentiment.  Finance asks to maintain its current privileged status and an audience guesses that this represents a sense of entitlement.  Guessers, including politicians and regulators, could potentially be surprised at the extent to which rank and file financial employees would accept a puppy-like smack on the nose or, in more common trading floor parlance, told to go fuck themselves.



*Two aspects of Introvert/Extrovert interest me most. One, that the rise of extroverts corresponds to Professor Cowen’s Great Stagnation thesis. Two the possibility that the necessary skill set for success has made an almost exact 180 degree change from the 19th and early  20th.

6 thoughts on “Askers vs Guessers in Finance: Askers are Annoying, Rich

  1. Carson says:

    I don’t think ask/guess correlates that strongly to the introvert/extrovert continuum. There are plenty of socially functional introverts and socially dysfunctional extroverts. Fear of rejection and difficulty saying “no” is not in my experience a characteristic of introverts (like myself).

    Paradoxically, askers when saying “no” often feel an obligation to justify the response. Most guessers I know, while feeling a bit stressed about saying “no” are able to do it without feeling compelled to justify or explain.

    “Can I use your spare room for a two weeks?”
    “Why not?”
    “None of your business” – this is unfair in the askers world. Askers feel compelled to give a “valid” reason. Even if it’s BS. In the guessers world, no one else gets to judge the reasons behind the response.

  2. Sean says:

    I don’t see the great change in power between extrovert/introvert. I see a lot of introvert personalities succeeding. Wouldn’t Zuckerberg/Bill Gates be consider primarily introverts who developed some extrovert skills for their public CEO roles. Also a lot of the best traders I know seem to be more introverted and are more comfortable with private contemplation. I would think the trading business as a whole has moved to the introverted side as the anonymity of the screens is more comfortable to them than the noisiness of the loudest voice in the trading pits.

  3. […] Questions, Asked I like the questions this guy considers. Askers vs. Guessers or Introvert vs. Extrovert. Looks like his thinking got kicked off […]

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