According to The Mack, I am truly gifted at asking the right questions.  The questions that other people don’t even think of.  He thinks it may be because I ask soooooo many goddamn questions that a few of them end up being on the money.  Still, he did say that he thought it was my greatest single weapon in my quest for world domination, ahem, starting a business.  And so I thought I’d better write that down for posterity.  And then prove it.

critical thinking

As a lawyer, you are (if you’re any good), pretty accomplished at taking a whole load of information – most of which has been babbled at you by a client whose method of expressing themselves most closely resembles a neural pinball game – and corralling that information into some semblance of order.

You then have to extract the relevant issues from the information you’ve assimilated, analyse those issues, apply the legal knowledge and expertise that you’re supposed to have to those issues, and come up with a solution for your client.

The way you do all of that?  Questions, questions and more questions.  And I’ve discovered it helps if you write the answers down.

The same rules apply when it comes to your business.  Learn to ask the right questions of the right people and the whole start up process will suddenly seem so much less daunting.

Q.  when should I ask questions and when should I pretend that I already know everything?

A.  I don’t really have a fear of asking questions (quizophobia??), nor of looking stupid (statistical probability).  I’m one of those superficially knowledgeable people.  You know, a bit like Henry’s Cat.  I know lots and lots about nothing, and not too much about that…  So I can come across as worldly and clued up, but actually I’m pretty darn ignorant.

Which means that, if I’m in a situation where I’m lucky enough to be talking to someone who actually has real, genuine, actual, honest-to-god knowledge about a topic, I will happily quiz them till I run out of questions (or they run out the door, whichever comes first).  My mantra – if you don’t ask, you don’t get.

My thinking is, most people like to share their knowledge.  It gives them the gentle glow of superiority.  Asking questions of someone demonstrates that you are interested in what they have to say.  And that is precious salve to the average human ego.  Don’t waste an opportunity to get your hands on some expertise, just because you’re worried what the “expert” will think of you.  Most times they won’t remember you anyway…

Q.  what questions should I be asking?

A.  Good question, you’re getting the hang of this!  It’s going to depend on the context.  The way I formulate questions is to break down my problem into logical segments based on what I know already, so that I can identify the gaps in my knowledge (‘cos that’s where the questions are hiding).

Let’s take the scenario where you have an idea for a product, but you need someone to help you with the design and development of that product.  You’ve found a few potential developers, but you’re unsure who to go with.  You’ve asked a few basic questions, like how much will it cost and what the initial steps would be.  But what else?

Here I adopt a Johari’s Window* style analysis (ooh, fancy).  Between you and the developer there are four possible combinations of shared knowledge:

1.  known knowns:  these are facts about the product/development process that are known to both you and the developer.  So these answers are already in the bag.  Right now, these might only be the basic description of your idea and the cost and initial steps of the development process.

2.  known unknowns:  (also called your “blind spot”) this is information that is known by the developer but which is not known by you.  This is where you should be formulating your questions.  Ask the developer what experience they have in working with people in your situation and with similar ideas to yours.  How does the development process work?  What input will they need from you and what form will this take (e.g. meetings, telephone calls, emails?).  How long will the process take?  What problems have they encountered on previous projects and what have they done to resolve them?  Do they envisage any problems here?  What do the quoted costs specifically include? Are there any hidden/extra costs?

3.  unknown knowns:  this is information that you have squirrelled away in your head, but that the developer might need in order to do the job or even accurately to quote for it.  Don’t hold back information (if you’re worried about confidentiality, get the developer to sign an NDA).  Try to give the developer as much info as you can think of.  Then ask the developer what other information they need from you now and ongoing on the project.

4.  unknown unknowns:  in this context, these will be things that neither you nor the developer have thought of.  Don’t worry about that.  I’ve never once come across a project that didn’t bring up some unknown unknowns (also called WTFs).  If you’ve asked the right questions in the earlier stages, then it shouldn’t be anything that you two can’t handle.  You’ll be fine.

Q.  who should I ask?

A.  Generally, someone with more knowledge than you on the subject.  Or Stephen Fry.  Probably.

But seriously, I’m a practical problem solver.  I don’t often go in for conceptual debates on hypothetical issues of the day.  I want straightforward, pragmatic, relevant advice.  Preferably from someone who’s been there, done that, got it right (or better, got it wrong and figured out how to get it right next time) and written the book.

That doesn’t mean that I expect other people to fix my problems and give me all the answers.  But it does mean that I seek out people with specific experience in dealing with my particular issue (and I’ll interrogate them mercilessly to pinpoint the relevance of that experience).

I’m also prepared to pay for that expertise.  Scrimping on real expertise is a massive false economy.  I’m not suggesting being overawed by their brilliance and telling them to name their price.  I am saying that if by paying for their advice it enables you to skip forward 3 steps on your business plan, then that’s money well spent.  And, in my world, it entitles you to tap them for some free follow-up advice should you need it in the future.

Q.  so I should just follow their advice to the letter, then?

A.  Err, no.  Have you been listening to a word I’ve said?  What is the topic of this post?  That’s right, questions… Keep up.

Check that the advice or proposal given actually solves your problem.  It’s a bit like exam essay writing at school.  You remember?  When the teachers drummed it into you to ANSWER THE QUESTION.  Yet it’s amazing how common it is for someone to think they’ve given you the perfect answer, but actually they’ve turned sharp left and embarked on an utterly irrelevant tangent.  On your time and money.

If you don’t feel that you’ve got your answer (and you’re paying for it), then go back and ask for clarification.  Don’t be scared that you’ll look foolish – there is nothing more foolish than paying for a service that you haven’t received.  It’s a bit trickier if you’re asking for free advice – you’ll probably be told to jog on – but you never know your luck!

A quick final word on that last point.  By all means, take full advantage of any expertise you can draw on for free amongst friends and family, but be aware that this comes at a price to them (their time and energy), so be considerate, very grateful and prepared to do something for them in return.

*Nerd note: Johari’s Window is usually used for self-awareness and character analysis.  But I think it works just fine for this purpose too.