Even More Guiding Questions

Where do I produce my best work?
Setting your own agenda is a wonderful feeling, especially if you’ve ever worked for a large corporation.
The tradeoff here is that you’re still responsible for producing a large quantity of work, and a fair amount of it needs to be of exceptional quality.
To achieve this, you’re going to need several effective workspaces, places where you’re not distracted by your phone and can rip through your task list.
I’m not talking about responding to emails here, this is where you’ll do your deep thinking and take creative risks.
Is it somewhere in your house?
A few cafes?
A co-working space?
Aeroplanes?

My suggestion is to have more than one option, and at least one option that you can control, in case the others are closed or unavailable.
What conditions help you get swept up in your work?
High ceilings?
Good internet?
No internet?
Caffeine on hand?
Somewhere safe to leave your stuff?
If you don’t have a good workspace, your job is to find or create one ASAP.

Where is my tortoise shell?
Creative and entrepreneurial work is draining, especially when you are the person responsible for every task and obligation.
When the pressure inevitably builds, do you have a retreat?
This might be a physical space, as well as a psychological space.
e.g. it could be your study, it could be your local pool, cinema, a long drive or time with your family.
Somewhere you don’t have a million notifications going off, somewhere you can process the events of the week, or can spend a day in a positive headspace.
Ideally this is a place you can access in a hurry, as opposed to a relaxing holiday in six months’ time.
It’s also helpful to think about what activities or processes help you recharge, like cooking, watching movies, time in the ocean, conversations with a therapist, or playing with your pets. 

How will I manage my battery?
Since we’re becoming more productive, battery management has become an essential skill.
Do you find your mental battery runs out at crucial times?
Does it take a long time to recharge once it’s flat?
Do you know which tasks drain your battery particularly fast?
What would you do if you had an additional 20% battery each day?
Remember, if you don’t give your body time off, it will take time off for you, most likely at a very inconvenient time.
Repeatedly running your battery down isn’t good for you, it’s not impressive and it makes you less productive in the long run.
We need you to keep building this thing for a decade, please don’t burn out in the first six months.

How will I stop things from falling through the cracks?
Whenever you have ten tasks pop up in a day, how many of them get done on time?
Are there trends in what gets missed?
Is it the important-but-not-urgent tasks?
Is it relationships that end up neglected?
Is it the big picture tasks, or the nitty-gritty details?
You’re going to need a system for getting things done, because as the project scales up these issues become magnified.
Do you need a technical solution, or a new set of habits?

What is sacred?
Your project is comprised of hundreds of elements, from the intent to the design to the choice of platforms and the way you treat your customers.
A lot of founders draft ideas for each of these elements in the “dreaming” stage, with many of the details changing by the time they reach a finished product.
But some of those details will remain intact.
It might be the colour scheme, who you partner with, how your products are displayed, how your services are delivered, how proceeds are divided, etc.
The reason these remain the same is usually because they feel sacred – integral to the identity and essence of the project.
To compromise on them would be like scrapping your initial vision altogether.
I’m not here to change your mind on what to hold as sacred, but it’s worth identifying which elements are not up for debate or compromise.
Naming them from the outset will help prevent others from stepping on your toes, or making suggestions that you’re guaranteed to reject.
At the same time, writing these out forces you to question exactly why each element is sacred, and why those details are so influential over the business as a whole.
It’s worth remembering that you are allowed to change your mind whenever better information and better options become available.
You can change your logo to a better one.
You can move to a more suitable location.
You can sell a completely different range of services to a completely different group of customers.
The things to keep sacred are your principles, your purpose, and how you make people feel.

How do I want people to describe our work?
I see a lot of style guides, brand templates and business plans that are 50-80 pages each.
They go into great detail around colours, fonts, fitouts, brand identities, values, visions and touchpoints.
The interesting thing is, customers won’t use anywhere near this much detail to describe what you’ve created.
They’ll probably use a few words or maybe a sentence to sum you up.
All of your detailed planning leads up to influencing these few words.
What words do you want them to use?

Here are some examples:
Fun
Elegant
Easygoing
Sophisticated
Visionary
Luxurious
Friendly
Professional
Lifesaver
Authentic
Decent
Rebellious
Bargain
Cool
Valuable

Here are some you might not like:
Disingenuous
Overpriced
Cold
Confusing
Mercenary
Pushy
Average
Cheap
Forgettable
Arrogant
Deceptive

Which words resonate?
Which words would you hate to hear from your audience?
Once you’ve picked your target words, can you collect some examples and images of other brands who also embody these words?

Who is it NOT for?
Whose opinion am I happy to ignore?
Who is never going to see the value in what we’re creating?
Who doesn’t want to like this?
Can I tune them out?
Can we still treat them with respect?
Your job is not to be universally liked.
Nothing is universally liked, and you’re unlikely to be the first.
I often find that dropping the need to impress the most difficult 10% of the market removes 90% of the headaches. 

How will I eat my vegetables?
Your daily task list is going to look like your dinner plate:
Some protein and carbohydrates for sustenance
Some vegetables for nutrients
Some delicious treats for joy.
Everyone agrees on the old cliché; you need to have balance.
What they don’t mention is that you’re likely to hate balance, instead opting for more of what you like and less of what you don’t.
Generally speaking, the hard part is keeping up the vegetables; not traditionally as tasty as steak or carbonara or chocolate mousse.

There are two tricks here:
1. Find the vegetables you naturally like, and minimise the ones you don’t.
There are so many to choose from, it’s unlikely you’ll hate all of them.
2. Learn how to make the vegetables tastier.
I had a revelation when I first tried a crispy baked Brussels Sprout, served with hummus, dukkah and a little bit of honey.
The stereotypical “worst vegetable” was massively improved by cooking it a different way – crunchy instead of soggy.
For your project, you’re going to have similar opportunities.
How might you find versions of your least favourite tasks that you don’t mind?
Can you complete them in a different way to make them more palatable?
If you hate social media, why not copy the content strategy of other creators you like?
If you hate bookkeeping, why not switch to an easier accounting program, or do your bookkeeping from your favourite café?
If you struggle with deadlines, why not get an accountability buddy who motivates you and celebrates your wins?

How might I support my gut feelings with evidence?
Gut feelings and intuitions are a blessing, but they aren’t sufficient for making expensive decisions and bets.
By all means, use them as a starting point, so long as you follow it up with evidence that proves/disproves your suspicions.
It takes genuine restraint and maturity to not skew the research process towards your desired outcome, but the payoff is extraordinary.

What steps can I take now that will remove my fear in the future?
I used to have a neighbour who was afraid of dogs.
He used to hate walking around the streets in case an angry or energetic dog took issue with him.
That is, until he discovered a neat solution; he started carrying a packet of Schmacko’s in his shirt pocket.
These dog treats worked their magic by turning any unfamiliar dog into an instant friend, taking the fear out of any situation.
The Schmacko’s are a genius move; they’re cheap, easy to carry, and they work even if you don’t encounter a dog on your walk.
They make you feel ready for anything.
For your work, what makes you nervous?
What can we prepare now that will take out the fear?
Is there an item you can buy?
A course you can take?
A trusted advisor who can cover your blind spots?
What would you do more if you didn’t have that fear?

Which skills do I need to learn, and which skills require a professional?
What skills will help to take your work to the next level?
Do they need a once-off burst, or do they need to feature in your daily work?
Do they need to be present in your team, or can they sit with a contractor?
Is it worth paying for a particularly good professional, or will a cheaper one suffice?
Do you know how to tell the difference between good and great work?

Am I dragging outdated assumptions and biases into this modern venture?
Veteran presence can be a mixed blessing; you carry a wealth of knowledge, but also a collection of old assumptions.
We notice the extreme examples like sexism, racism or old people who don’t trust technology, but we each see the world through our own subtle biases.
Are you bringing in preconceived parameters around money?
Hiring?
Growth?
Fairness?
Customer preferences?
Nobody likes admitting that they have a bias, but once you name it you can address it, and therefore make better decisions.
What would your younger competitors do differently?
What fresh worldviews might they bring to this work?

Is there a deep supply of customers?
A business can only succeed when there is an adequate pool of customers.
If you can’t tell me where the adequate pool of customers is located, then it might be worth formulating a new plan.
Where do your dream customers naturally congregate?
Where are they today?
Do they communicate with each other?
If you lose some customers, can you easily replace them?

Do I have to push uphill to find customers?
Starting a business is hard, but it shouldn’t be really hard.
It’s hard in that there’s a lot of things on the to-do list, but it shouldn’t be a massive strain to find someone who wants what you sell.
A good business is one that you can push downhill – where there’s natural momentum and customers refer you to more people like them.
Sadly I see a lot of new founders pushing the business uphill.
They tell themselves that it will get easier once they grow, but the truth is that will only magnify their problems.
If it’s really hard to get 100 customers, it will probably be much harder to get 1,000.
What can you start that can be pushed downhill?
What is the market asking you to build?

Do we want to be known as being better than the competition or cheaper than the competition?
Seth Godin describes the two main strategies in business as “we’re better than the competition” versus “we’re cheaper than the competition”.
It’s almost impossible to be both, and very hard if you’re neither.
Which best describes your strategy?
Better how?
Cheaper how?
In whose opinion?

How much better or how much cheaper do we need to be in order to overcome the switching costs?
I bet you won’t switch phone providers to save $1 a month.
I bet you won’t move house because another one has slightly better carpet.
There are natural barriers in our life that keep us in our comfort zone, since our brains like things that feel familiar.
If you want someone to overcome these barriers, how much of an incentive do you need to offer?
How much cheaper does it need to be?
How much better does it need to be?

When things get stressful, what bad habits do you revert to?
Mike Tyson said “Everyone has a plan until they get punched in the mouth”, and this is particularly true for startup strategies.
What they forget is stress – just because they can make time available for a task, doesn’t mean they’re going to do it well under pressure.
What happens when you’re anxious?
What happens when you’re overburdened?
What happens when there’s time pressure?
What happens when customers or partners change their minds?
What can we put in place to minimize or remedy this in advance?

How can we cap the downside risk?
What if the priority wasn’t avoiding all risk, but rather reducing the severity of the worst case scenario?
Richard Branson famously did this when starting Virgin Airlines – buying a used plane from Boeing and pre-negotiating to sell it back to them for a certain price if things went bad.
This gave him a backstop, some certainty that the worst outcome wasn’t a total disaster.
How might you do this for your work?
If you capped the downside, what would that free you up to do?

Who are our dream customers?
If a genie offered you any five people in the world to be your customers, who would you request?
Why them?
Is it because they’re famous, or because they’ll love what you can do for them?
Who are the best customers in your field?
Who are the big fish?
Who are they shopping with today?
What would be so good that they’d consider switching over to you?
If nobody comes to mind, could this be a sign that you don’t know your market, or aren’t thinking big enough?

Am I looking for customers for my products, or products for my customers?
There’s a temptation to go with the former, but the latter tends to produce the best results.
It’s easier to change your products for wonderful customers, rather than try to magically conceive the perfect customer for your products.
If you went looking for products for your customers, what might you create?
What would they love?

How can I outsource or offset my weaknesses?
Chances are that you have weaknesses – we all do.
Rather than trying to be a Jack of All Trades, how might you cover your weaknesses through a partner or new solution?
Can you outsource the things you’re weakest at?
Can you make those weak areas irrelevant or obsolete in your project?
How many extra sales would this facilitate?

How can I double down on my strengths?
Rather than fixing weaknesses, what if that same energy was used to double down on your strengths?
What would that enable you to do?
What would that mean for your audience?
What would that mean for your enjoyment in your work?
What would you do to grow your strengths even further?

Instead of waiting to get picked, how might I pick myself?
A lot of new creators want to get “picked” by their industry.
They want to wait for someone else to see them, deem them worthy and declare them as being worth the attention of their audience.
You see it in reality TV competitions, university applications, design school, anything with a tough gatekeeper.
There is an alternative – you pick yourself, and start doing the work.
This is when you create your own music and promote it online, or play at small venues while you practice your craft.
This is when you start your own channel, your own website, and find people who naturally appreciate what you do.
This path feels harder at first, but it gives a much greater sense of control over the process and outcome.
You don’t need to apply to start your own online store, you get to choose yourself and do the work.
It’s still hard work, but at least you control your own future.

How do I want my customers to feel?
When we map out customer journeys, it’s tempting to focus on what your customer does, but not how they feel while they’re doing it.
Are they excited?
Confused?
Anxious?
Overwhelmed?
Bored?
Delighted?
How do they feel in the system as it stands today?
How would you like them to feel in the future?

What are our core values? What are our aspirational values?
By understanding your values, you can begin to see why your audience likes your work, and can recruit team members who will be compatable with your systems.
There are a few different types of values too:
Core values are traits and behaviours that you tend to take too far.
Honesty isn’t a core value, unless you’re so honest that you sometimes talk a customer into spending less money.
These are sometimes in our blind spot, since we don’t know how much they influence our actions, and when they do it feels obvious or invisible.
Aspirational values, on the other hand, are the traits and behaviours you’d like to have, but aren’t quite living out today.
Values identification exercises can be really valuable, but only when you’re 100% honest with yourself and your team.
If you sugar-coat the truth, the whole thing becomes tokenistic.

Are good team members found or made?
Can you find perfect candidates on job search sites, or are you looking for something far less generic?
If good team members are found, where do you find them?
If they’re made, how do you make them?
Either way, you’ll want to think about your strategy now, since making great team members often needs a long lead time.

Where do I find a running mate?
There are good team members, then there are running mates.
A running mate is someone you can trust with your biggest challenges, whose opinion you seek out, and who helps you manage the project as a whole.
They might be a deputy CEO, a fellow creative, a co-founder, anyone who can walk beside you along the journey.
Firstly, do you believe it’s even possible to find such a person?
Who do other people in your field turn to for counsel?
Are these people found or made?
Do you have people in your life today who might become a running mate in the future?

Which roles are worth paying overs for?
Across all aspects of life, people form their own worldview about three things:
1. Times when the bare bones version is good enough.
2. Times when the mid-price version does a great job.
3. Times when you get a significantly better result from paying the highest price.
e.g. how they decide on a phone, car, pet food, greeting card, dentist, charity or shoes.

The same goes for your team; which roles can be covered by a lower cost team member, and where do you see a vastly better result from the top performers in the market?
Is it the person who runs your sales strategy?
The person who helps set your culture?
Your top project managers?