More Guiding Questions

Following on from the last post, here are some more helpful questions to think about for your project or business.
Some of them might feel irrelevant, others will be on your mind for weeks…

What is my risk tolerance? What is my risk appetite?
Risk is such a hard thing for the brain to quantify.
To make risk assessment decisions, we need to estimate the likelihood of different events happening, as well as the consequences of those events.
We can then try to balance the upside of certain scenarios versus the downside of other scenarios, and choose whether or not to proceed.
e.g. the joy of riding a motorbike versus the risk of being in a road accident, then deciding whether or not to buy a bike.

These decisions are further influenced by two things:
1. Your risk appetite – how much you enjoy taking risks, with the hope that the good outweighs the bad.
2. Your risk tolerance – how easily you can handle potential downsides and still function at a high level.
e.g. Your risk appetite might affect how much you enjoy playing Roulette; some find it thrilling and some find it stressful.
Your risk tolerance might affect how much money you’re happy to wager on Roulette, playing with $20 will feel different to playing with $2,000.

What’s interesting is that we can sometimes mix these up.
I might consider myself a low-risk type of person, but can still have a high risk tolerance (like playing Roulette for the first time with $20).
Just because Roulette makes me nervous doesn’t mean that the game will be dangerous for me, if I’m just playing with a small amount.
So for conservative people, it’s important to separate your personality from your circumstances.
There are plenty of worthwhile risks worth taking, if you have a high risk tolerance:
·      Leaving a job you hate
·      Starting a business
·      Joining a startup
·      Running ads on Instagram
·      Entering a partnership agreement
·      Hiring your first employee

If you tell yourself that you can’t do these because you’re “not a risk taker”, you’ll miss out on a lot of upside.
Instead the key is timing it with the rest of your circumstances.
If any of the above would result in huge financial or personal troubles, it’s wise to hold off.
Not because of your risk appetite, but because of your risk tolerance.

What is it about to be the perfect time for?
In hindsight, 2009 was the perfect time to buy Bitcoin, 2011 was the perfect time to create a YouTube channel, and 2019 was the perfect time for that international holiday.
You can still do these things in the future, but they’re nowhere near as easy.
Rather than building a time machine, what will 2021 be the perfect time for in hindsight?
What platforms are emerging?
What content or assets will be valuable in a decade?
What technology or trend is starting to show signs of promise?

How can I preserve the joy in my work?
When people talk about scaling up a business or project, they measure success in revenue, exposure, headcount, customers served, profit made or increased valuation.
They never ask you if you’ll find joy in your work.
It seems like a stupid omission, since joy is both what got you started, and will be what keeps you going once the novelty of wealth wears off.
Very few people aim to be rich and miserable, and a lot of the richest people I know aren’t the happiest.
What would need to be in your typical work week to keep it a joyful way of spending time?
What could you outsource?
What won’t you outsource?
What policies will prevent your workspace from becoming dreary and soul-sucking?

If I can’t create the thing I dream of, can I at least create the thing I’m capable of making?
There is often an uncomfortable disconnect between what you can envisage in your mind, and what you can realistically create today.
You might be able to imagine masterpieces, but haven’t yet mastered your craft, and this misalignment leads a lot of people to quit.
Perfectionism is the mindset that says “If I can’t make a perfect one, I won’t make anything”, and while that might sound noble it essentially ends your project.
What I love about this question is that it gives you permission to create your best work, even if it’s not the best work.
Deciding to do the work improves your skills and builds a valuable habit, both of which enable you to create better work in the future.

Can I get thicker skin?
There’s often a difference between risks that will derail our progress, and risks that will make us feel uncomfortable.
e.g. the risk of running out of money vs the risk of looking goofy in the media.
More often than not, it’s the second category of risks that scare my clients the most.
They’re not afraid of failure, that’s a well-known part of entrepreneurship.
They’re afraid of looking like a failure, of the shame, of the awkward questions from their families at Christmas lunch.
When they post something online, they ignore the ten positive comments and dwell on the two negatives.
While most bottlenecks in business can be solved with a product or service (like buying more bandwidth or opening a second outlet), there aren’t any shops I know that sell thicker skin.
It’s something that you’re going to have to deliberately acquire for yourself.
It comes from realistic expectations, mentors, friends, a community of practice, good books by other creatives, downtime, and by looking at situations from a range of perspectives.
This might feel like a slow process, but the return on investment is phenomenal.

What would you do if your nerves didn’t stop you?
Run more campaigns?
Build an audience?
Try new products and services?
Speak at events?
Pitch to new customers or partners?
Be more open with your team?
Delegate your tasks?

Can I make progress in secret?
One of the secrets to thicker skin in a new project is the balance of progress versus questions.
For example, if you tell your circle that you’ve taken up tap dancing, then after a few drinks they’re going to cheer for you to show them some moves.
If you’ve done two weeks of tap classes, this is a dreadful prospect.
A solution is the three month rule: don’t tell anyone about it for the first three months.
After three months of a new project, you’ve made a bit of progress, changed your approach or your goals a few times, and have a little something to show for your efforts.
In the spirit of eating my own cooking, this is exactly what I did with this site, I didn’t tell anyone about it for three months, at which point I had a better sense of what sort of content I liked publishing.
Three months is enough time to make some prototypes, interview customers, create a landing page and iron out the initial wrinkles in the work.
It’s still early days, but would it take out a lot of the pressure and expectation you feel?

How might I kick an early goal?
The tone of a new project can change drastically if you can kick an early goal.
This might be an in-principle agreement with stockists or suppliers, a glowing review in a publication, positive responses on an early prototype, a purchase agreement with a customer, a successful launch event, etc.
There’s an element of luck to each of these, but you can do things to increase your odds, like building several iterations of a concept, creating real-world prototypes, thoroughly understanding the needs of your market, spending money on good PR, etc.
An early goal doesn’t guarantee that you’ll win in the long run, but it sets the tone both internally and externally, both of which increase your chances of success.

Can I give myself a grace period while I work through “The Dip”?
One of my favourite books and concepts is The Dip by Seth Godin, which I’ve covered in a previous article.
It describes the process by which most projects start well, then get hard, and then maybe get really good again.
e.g. learning a new language, hobby, musical instrument, etc.
What can make The Dip (the crappy bit in the middle where the work stops being fun) is that we are our own harshest critic.
Our internal monologue persuades us to stop, sometimes with kindness, often with cruelty.
Are you happy to go easy on yourself once you can see that this is The Dip?
Can you give yourself a grace period, without expectations or criticism?

What is my mistakes policy?
Nominally speaking, most people accept that mistakes are an inevitable part of life.
Emotionally speaking, we tend to either personalise mistakes (this went wrong because I’m a failure) or we allow ourselves to fall back into bad habits (setting new team members up to fail in the same way as their predecessors).
What I love is Fiona Killackey’s “Fool Me Twice Checklist”.
Some mistakes can happen once, and that’s life.
But we’re going to take note of them, and pledge to never make the same mistake again.
We’re very forgiving of ourselves the first time, then take full responsibility for never letting them reoccur.
Making a list is helpful, because it lets you teach others how to avoid the traps that caught you out in the past, and perhaps their lists can save you a lot of time and stress as well.

Here are some of mine:
·      Do I have the right cables for my computer?
·      Do I have the right visa for this overseas trip?
·      Which item on the menu is least likely to upset my stomach before this long haul flight?
·      Have I forgotten anything on this invoice? Have I included the right taxes?
·      Where’s my powerbank?
·      Have I re-read the contract now that we’re half way through the project?

In terms of price, whose opinion matters most?
Here’s a great recipe for failure: try to please everybody.
When everyone has their own perspective, the things that you’re creating are bound to evoke a range of responses.
Some people might love it, some might like it, some might dislike it, some might hate it, some might misunderstand it, some might ignore it.
There are people who hate your favourite movie and your favourite food, and that’s ok.
Given all of this, whose opinion are you focused on when it comes to your prices?
How much do they expect to pay?
What’s their budget?
What do they see as being too expensive?
What do they see as being suspiciously cheap?

You won’t be everyone’s cup of tea.
Furthermore, you won’t change people’s minds by making yourself a cheaper cup of tea.
The magic phrase to think about when the wrong customers criticise your prices:
“It’s not for you”. 

Who will point out my blind spots?
When you’re in a position of leadership, you develop new perspectives that let you see what others don’t.
This comes with a catch – you’ll also lose some perspective.
For example, you’ll see the emerging options for the next 18 months’ worth of work, but lose sight of how your team view the future.
You might be excited, while they might be afraid, or vice versa.
Every leader needs people around them who can provide these additional perspectives, either through advice, constructive criticism or a reality check.
While they might bring what feels like bad news, these people nip problems in the bud, and save you a lot of time, money and reputational damage in the future.
If you don’t have people around you who can give honest feedback in a safe way, where might you find them?
Whose opinion would you trust?

Who could be my sparring partner?
“Sparring” is a term from combat sports, describing a type of training where two people practice their techniques without trying to hurt each other.
The aim is to practice your skills in a low-to-medium stakes environment, preparing you for the real thing.
While most of us don’t need physical combat in our work, debating new ideas is a great way of testing their strength and validity, helping us make better decisions and spot problems before they become costly.
A great example of this is Richard Harris and Craig Challen, the two divers who made the Thai Cave Rescue possible in 2018.
They wrote an incredible book called Against All Odds, in which Richard Harris describes his negotiation process with the Australian Government who wanted his help:

“The man on the phone said that AUSMAT – the Australian Medical Assistance Team – would be taking part in an official mission authorised by DFAT.

‘The simplest way for us to do this is to send you as an AUSMAT representative, a team of one’ I was told. Personally, I didn’t care who authorised the trip – I’d be happy to represent the Australian darts team – just as long as the trip was approved. But before I agreed to go anywhere, I had to get something straight.

Team of one? How about a team of two?

‘This is important,’ I said to the man from Canberra. ‘I need this bloke called Craig Challen to come with me. He’s my dive buddy.’

That was greeted with silence on the line.

‘Um,’ the man said with a sigh. ‘That could be an issue.’

‘If I’m going to do this,’ I insisted, ‘I need a trusted ally in the water with me – and more importantly, on the surface, to help me argue through everything. He’s a highly experienced diver. I need Craig there.’

It was then patiently explained to me that, whatever Dr Challen’s particular talents, he was not a member of AUSMAT. There was no quick and easy way to approve his joining the mission. ‘I’m sorry,’ the man said.

‘I’m sorry,’ I said. ‘Let me put it another way: if he doesn’t go, I don’t go.’

I wasn’t bluffing. When there’s a complex diving problem, Craig and I can always tease things out together. He’ll challenge my assumptions. He’ll think of things I didn’t think of. Just explaining my thinking to Craig forces a certain rigour on me. And it’s mutual. I do the same for him. I couldn’t imagine a mission much more complex than this one. I needed my trusted arguer at my side. We had a lot to thrash out here. Young lives were at stake. We had to make sure we weren’t doing anything dumb.”

That’s such a beautiful description of a sparring partner – a trusted arguer at your side.
Do you have one?
Perhaps a few people who can cover a range of subjects?

What assets do I need to build quickly?
Some assets are required to serve just a single customer, like your supply of component/ingredients, your intellectual property, your workspace and your skeleton crew.
These are what allow you to create the appearance of professionalism, make promises and then deliver on them.
A helpful way to think about this is to imagine your basic Customer Journey, and create all of the “touchpoints” a customer needs to interact with.

What assets do I need to build eventually?
Some assets are important but not urgent, particularly things like backups, systems and training tools.
For example, what happens if a key team member leaves?
Do you have training materials that can bring someone else up to speed?
Or what about the systems and processes you used at the beginning; how will they hold up when you have 5x
more customers coming through each month?
There will never be a convenient time to build these assets, you’re going to have to deliberately create the right time and circumstances.

Can I take smaller bites?
A massive reason why important tasks stay on our To Do lists is that they’re too complex to do in a single session.
There’s rarely a spare weekend to throw at these challenges, either because you’re busy or because you feel overwhelmed at the prospect.
What helps is taking smaller bites – breaking the task down into 1-2 hour components, so that you can make progress throughout your normal week.
My rule is that if I can’t work out how to split the task into smaller bites, it’s because I don’t thoroughly understand what I’m doing, and need to find someone who can help me visualise the little milestones.

What are the 50 things I need to do next?
A helpful process is to make a list of the 50 small bites I have on my plate.
It might be 10 bites for each of 4 main projects, plus 10 miscellaneous tasks.
Depending on how my day is going, I might have a preference for certain tasks over others, e.g. something mindless and repetitive, something creative, something that requires 20 seconds of courage, something that I can take to my sparring partner, etc.
By building a list of 50, I can pick something valuable that matches my headspace, rather than straining to shift gears.
The act of making the list is therapeutic in itself-  it clears your head, highlights your priorities, sparks your thinking, and helps you realise which tasks don’t need to be done at all.