Dealing With Difficult Questions

Communicate Like a Human: Lesson 6.

Nobody likes to look stupid

All of us have times when we don’t understand a difficult question.

We don't like to say "I don't know" too often.

We worry that saying "I don’t understand" will create the perception that we aren't the brightest of sparks in our particular fuse box.

To avoid looking ill-considered or like you’re, well, making stuff up, use the technique Google falls back on.

The chances are, you already do. You just rarely give it conscious thought.



I don’t know

Siri deals in the definite. She lives in the literal. If Siri knows the answer to your question, she will gladly furnish you with that knowledge. It is the most straightforward way to exchange information.

When you ask Siri a difficult question for which she doesn’t have the answer, she will have nothing to exchange. So, her answer will be that she doesn’t have the answer.

‘I don’t know’ is an absolute. It is a conversation closer. It stops the rally of ideas and ends further interrogation.


I don’t understand

Alexa tries harder to deal with the difficult question. She quotes Wikipedia so often that you can imagine her copy of it might be extremely tattered and well-thumbed. If Wikipedia were an offline publication. And if Alexa had thumbs.

When the question proves too difficult, Alexa is quick to defend her own “I’m sorry, I don’t know the answer to that one”. She gives assurances she is working hard to learn more. Though this servility may suit your master/servant preferences, it makes her sound less human. Unless the human is a small child, living in fear of punishment by an overbearing parent.

More usually, the response you hear from Alexa when her knowledge cupboard is bare is that she doesn’t understand.

(Of course, it may just be that Alexa has a particular problem understanding my voice. That was clearly a shortfall in my research. But let’s go with it for this illustration.)


Lack understanding, not status

Few of us like to say we don't understand.

This comes from feeling the statement is commenting solely on our own knowledge, and lack thereof.

We see it as a declaration of failure.

But we can change that if we position it outwardly.

Provided it isn’t accompanied by a defeatist sigh and shoulder shrug, ‘I don’t understand’ can be an implied question. It can be a plea for help without having the neediness of a plea.

Directing ‘I don’t understand’ to your audience turns it from being a statement dismissive of your own intelligence to a question, deferential to the intelligence of your audience.

Not understanding enables the conversation to continue.

Don’t use it too often.

The reasons should be obvious enough.


Making stuff up

It is rare to hear Google admit a lack of knowledge when dealing with a difficult question. Though he has a particularly exasperated tone when delivering ‘sorry I don’t understand’.

Sometimes Google takes an approach to difficult questions that is much more human.

When we are asked a question that doesn’t have a single, absolute answer – like what is your name, or how is the weather – we give our opinion. We offer considered thought.

When Google is given a similar question, he starts to hypothesise. He imagines. He suggests and supposes. Now and again, you get the impression that he is just making stuff up. For the bants.

A close up of wooden numbers

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Creative supposition

Google's approach centres around the conditional conjunction.


It allows for supposition. It shows you aren’t closed to information just because you lack expertise. It also provides the opportunity for you to show your aptitude for creative thinking.

Of course, you will use 'if' already. You probably don't give it much thought. The examples in the clip just put a spotlight on the technique.

Google introduces the theoretical with a liberal use of the word 'If'.


If only and only if

As a POS (part-of-speech), 'if' is a conjunction.

Conjunctions most commonly connect two objects or actions in a sentence. We use them every day and don’t even think about the most common ones; and, for, yet, or, but, nor, so.

‘If’ is slightly different. ‘If’ is a conditional conjunction. When you use ‘if’, you are introducing a dependant, or conditional, clause that can only be theoretical.

‘If’ demands you imagine a scenario that hasn’t yet happened. ‘If’ makes you hypothesise.

Oddly, there is no real single-word synonym for ‘if’. The alternative ways to communicate dependencies tend to be conjunction clauses such as ‘depending upon’ or ‘assuming that’.

(‘Should’ is sometimes used incorrectly as many people explain on Quora.)

‘If’ is a tiny little key that opens the door to imagination, free-thinking and feeling.

‘If’ exists because it allows us to be human.



  • ‘I don’t know’ should only be your final option to a difficult question.

  • 'I don't know' will close the conversation.

  • ‘I don’t understand’ can have a positive impact when delivered correctly.

  • 'I don't understand' can demonstrate eager curiosity.

  • There is an implied question behind ‘I don’t understand’.

  • The conjunction ‘If’ is your smallest best friend.

  • Use 'if' sparingly and it will show creativity in your answers.


On to Lesson 7: Are Common Contractions Too Common?


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