I’ve been self-employed full time for the last three months now (minus a bit of time in Japan and I’m starting to appreciate the importance of asking the right questions in life and in business – but mainly in business.

“Asking the right questions” is a key theme in any business book. It’s a genre one should generally err on the side of caution and skepticism with, but there are some very good examples.

One mostly good example is The Lean Startup by Eric Ries. Ries basically spends the whole time startups need to be “asking the right questions”. Furthermore, Ries argues if only managers were better at asking the right questions, there would be more innovation and fewer missed opportunities.

I think Ries has a point: asking the right questions is a way of getting the feedback you needed but perhaps didn’t know you wanted.

So what are the right questions? These are the queries I’ve been using to frame my thinking, split into different categories.

Targets

What are my goals? This is simple to the point it risks being vacuous, but this is a legitimate question to be answering: what are you trying to do? You’ll often see “10x your goal”, but you can’t do that if you don’t know what your goal is in the first place.

We all know this, but if you had to write down goals for three months, six months, two years right now, could you do it? I’m willing to bet you couldn’t answer it straight away.

Goals need to be specific and measurable to be of any use. Again, probably know this but there’s a difference between knowing something’s a good idea and putting into practice.

So how do you put this into practice? I cribbed a great idea on this from Nat Eliason, I like to update a spreadsheet of “quantifiable goals” every Monday morning to see how I’m progressing vs where I need to be to meet goals. This keeps you laser focussed. Here’s Nat’s spreadsheet for doing this.

How do I go bigger on my goals? It’s so much more important to spend the time on what your goals are before you move on to thinking about how they can be bigger. Very clearly set your goals in the first place before you start doing this.

Sketching out “what would this look like if it was 10x bigger” is a useful exercise: you’re forced to adopt a different mindset and think of how what your doing would work on a much bigger scale. You’ll often think of tactics which will help you reach your original goal faster.

You’re unlikely to get to 10x, unless your original goal was wildly wrong in the first place, but this kind of thinking can help you make sure you do get to the original goal. Anything over that’s a bonus.

Work

How would this work if it took half the time? This is a great one! Radically reimagine your workflow and only get the important things done.

I’ve long subscribed to a thesis somewhere between Basecamp’s four day week, Tim Ferriss’ four hour week and John Maynard Keynes’ Economic Possibilities of Our Grandchildren (written in 1930, argued only 15 hours of work a week would be necessary). Basically, if you have less time you’ll:

Generally work faster. Spend less time on less important stuff (rather than the deep work).

Asking how your work could be done in half the time again forces the big thinking: you might not get to half the time, but 80% of the time would be a great result. Do that for everything and you can have an extra day a week off!

Reading other people’s advice

These absolutely applies to this post, just in case you’re wondering.

Is this post on Twitter/Reddit/Hacker News good, or just relatable? I have a new thesis that the content that gets the most shares is typically good and highly relatable, rather than excellent in its own right.

Good content is fine, but excellent content is better. I’ve found reading from high quality weekly newsletters is a much better option than checking Reddit or Twitter (I’d recommend Pocket Hits, Hacker Newsletter, The Modern Desk, Nat, Femke, Sean and… me).

Is this good advice? This is highly related the previous question. Bullshit advice, to quote an excellent piece by Henry Wismayer, is the stuff that:

“is utterly vapid, offering nothing beyond a few nauseating blandishments designed to appeal to the reader’s individualism and thirst for success”.

Great advice goes beyond throwing in a couple of statistics, a click baiting title and please enter your email to discover these AMAZING techniques. It also doesn’t fall foul of survivorship bias. Great advice is actually practical, explained in such a way you can properly understand it and is transparent about potential pitfalls.

Understand what the underlying lesson is and take out specific ideas, but recognise most advice doesn’t directly transfer.

Getting the right answers

A lot of this is relatively obvious, but sits in the hole between “things we vaguely know” and “things we actually apply to our work”.

Nothing here is especially groundbreaking, but I hope it’s though-provoking and you’ll start to put these into practice.

When I spend the time working out what I need to be working on, what needs to be done to get there and how I’m doing along the way, I’m a lot better at getting there. I very much doubt I’m alone in this.

The key takeaway here should be you’ll get huge benefit thinking about “the right questions”, and it’s well worth the time it takes to do this. Time to get the thinking hat on 🎓