Guiding Questions
At the start of any journey, the right question can massively improve your chances of getting what you want.
Questions help your brain determine what it wants most, how it will make tricky decisions and how it will know if the plan is working.
Once you’re clear on your preferences and dealbreakers, you can talk openly with your team, spotting opportunities for great partnerships while spotting trouble from a mile away.
Guiding questions help create clear principles, and clear principles help you navigate infinite choices.
Some of these will feel easy, some will feel confronting.
The aim is not to “pass the test”, but rather to be honest with yourself about your desires and motivations.
Let’s get started with some simple ones…
What do I want to build?
You should be able to write this answer on the back of a business card.
It shouldn’t be more complicated than that, but getting to simple can take time.
Is it a shop, a course, a platform, a safe haven, a label, a book, or maybe a sequence of things?
Are you drawn to a field, a craft or a community?
Who do I want to work with?
Very few people genuinely work alone – most of us use suppliers, partners, colleagues, employees, agents, not to mention our customers and our beneficiaries.
People do business with people, and they choose to do business with people they like.
Who would you like to work with?
Who would be helpful to work with?
What do you like about them?
Who do I want to serve?
Hopefully what you’re building serves someone beyond yourself.
This might be your customers, end users or beneficiaries – who is better off from your work?
What draws you to serving them?
How well do you know them?
What change do I want to make?
Now that you know who you’re serving, what do you want to do for them?
Where are they starting, what do you want to show or give them, and where will they be afterwards?
What does this look like at an individual level, and at scale?
How will I know I’ve “made it”?
What milestones will confirm your success?
Is it media coverage, a sum of money, how you’re treated, where you’re invited, the scope of your business, the amount of art you’ve produced, etc?
This is one you need to set in advance, once you get started your perspectives will change, especially as you get to know people who have been doing this for longer than you.
How will I know I’m on the way to “making it”?
Which milestones will show you that you’re on the right track?
Is it a growing audience, more stockists, more customers, or your first few team members?
When you’re exhausted and low on energy, what signs or indicators will help to reassure you?
Next, let’s look at some success criteria…
How important is status in this work?
This can be uncomfortable to talk about, but the desire for high status is a genuine motivator for a lot of people.
e.g. do you want to produce a book, or do you want to be a respected author?
Do you want to design clothes, or do you want to be celebrated as a designer?
Do you want to sing, or do you want to be famous?
The reason this is important to name is that it completely changes the success metrics for your work.
If status is the most important thing, you’ll need to get advice from others who have done the same thing before you.
Otherwise your mentors will help grow your margins or improve your craft, but you’ll feel unfulfilled by the whole experience.
How important is money in this work?
Money is an incredibly complex subject, full of psychological meaning and self worth, on top of what it can buy you.
How central is money to your motivations?
Do you have strong feelings about salaries, total earnings or selling what you create for a large amount?
Is money the main form of wealth and validation, or do other factors matter more?
How much money is enough for you?
How important is recognition in this work?
Some people love the spotlight, some love anonymity.
Maybe it’s a bit of both.
Fran Lebowitz said “The best fame is a writer’s fame. It’s enough to get a table at a good restaurant, but not enough to get you interrupted while you eat”.
Whose opinion do you seek out?
Do you want a small number of die-hard enthusiasts, or to be a household name?
What do you want to be known for?
How important is it to be liked by most/all people?
How important is freedom in this work?
Are you starting this project for autonomy, or do you thrive under tight conditions?
How much weight and responsibility do you want to carry on your shoulders?
Are you looking for freedom in how you approach your tasks?
Freedom in who you work with?
Freedom in where you work?
Freedom in what times in the day/week you like to work?
Freedom in your ability to take holidays and downtime throughout the year?
How important is the purity of my craft in this work?
A lot of creative people develop their craft over several years, then get to the point where they can monetize their skills.
The awkward part is that their customers may not share their appreciation for the sanctity and purity of the craft.
Think of chefs who cringe at customer requests, designers who get told to make the logo bigger, or the event planner who handles ridiculous and impractical client requests.
How much are you willing to compromise for money?
At what point is the customer right, and at what point do they stop being your customer?
How important is balance in this work?
Two tricky truths for you to consider:
1. Pretty much everyone agrees that work-life balance is essential.
2. Most of your favourite things were created by people without work-life balance.
Make of that what you will.
What does the concept of balance look like for you?
What sacrifices are worthwhile, and which are out of bounds?
Now let’s look at what you’re going to build first…
Who are my prototypical customers?
It’s very hard to visualise 100,000 customers – all of the cliche visual metaphors are things like stadiums or towns.
These treat people like a series of dots, and that’s not very helpful.
What we need instead is a detailed, empathetic portrait of 4-10 different people, each of whom represents a portion of our audience.
I personally have about 10 people who I personally know and work with, who I think of as my prototypical customers, and they change over time.
Website analytics might be accurate, but they don’t show you what to create next.
Analytics give clues, but people give you entire concepts.
What is most important or valuable to these people?
Once you can picture your audience, ask yourself: what do they need right now?
What do they want right now?
What would delight them?
What will they need in the near future?
Tools like the Value Proposition Canvas or the Jobs To Be Done framework are helpful in articulating what’s important and valuable, especially when paired with good quality interview questions.
What else would they love?
We tend to think of the field we know best, but it’s worth looking more broadly with our prototypical audience.
What other parts of their life are unfulfilled or could be further enhanced?
What pain points do they have?
What’s on their Christmas lists?
If they found a genie in a magic lamp, what would they wish for?
Think of Dyson, moving from vacuum cleaners to hand dryers, hair dryers, hair straighteners, air purifiers and heaters.
What else could you create for these people you know so well?
What sort of prototype could I bring to them?
A good idea is a starting point, but the magic happens when a customer interacts with a prototype.
This might be a landing page, a mock-up, an interactive experience or even an empty box.
What questions do they ask?
What are their dealbreakers?
What do they love?
What do they hate?
What don’t they notice?
How will I know they genuinely love it?
Verbal feedback is cheap and inaccurate.
What we really want is buy-in, like a pre-order or agreeing to a second conversation.
If someone loves what you’re making, they won’t hesitate to give you their payment details, email address or some other form of commitment.
If they’re evasive, chances are they don’t know how to tell you that they don’t love the prototype.
That non-verbal feedback is useful, if we properly acknowledge it and use it to either improve the product or find different customers.
Am I willing to remove my ego from this process?
Testing prototypes with your market requires humility and a thick skin, but the payoff is tremendous.
Are you happy to hear customers feedback, even if you disagree with their taste and opinions?
Are you happy to separate your identity and value from your work?
Now we’ll look at how you want to work…
In what way am I willing to be “Unreasonable”?
Unreasonable might sound like an insult, but a lot of innovation comes from people who decided to be unreasonable.
It might be an unreasonable focus on quality, speed, cost, authenticity or atmosphere.
The moment where you say “I don’t care that it’s less convenient to do it this way, we’re going to…”.
Great examples include Steve Jobs, Elon Musk or Sheryl Sandberg, each of whom reflect the good and the bad of unreasonability.
You’ll struggle to be unreasonable about everything, so it’s worth choosing “the hill you’re willing to die on” wisely.
What sort of team do I want to work in?
You’ve probably worked in a range of teams, and have experienced good and bad work cultures.
What sort of culture will help you achieve your goals?
Who needs to be in the mix for this culture to thrive?
Who has to be cut out for this culture to thrive?
Do you envisage a small team of 3-4 specialists, a boutique of 15, or three entire floors of staff in a skyscraper?
What might a typical day look like in 5 years’ time?
What time would you wake up?
What would be your morning routine?
What’s the split of creating vs managing?
Where would you work?
What would make it a great day?
Do I aspire to be a Technician, a Manager or an Entrepreneur?
Michael Gerber has a great book called “The E-Myth Revisited”, in which he outlines three roles in every business:
The Technician, who creates the products and services.
The Manager, who makes each day run smoothly.
The Entrepreneur, who runs the business and oversees it’s growth and evolution.
Chances are, you gravitate to one of these three roles.
What role do you like playing?
What do you like the least?
How do you feel about being The Entrepreneur?
If you’re not The Entrepreneur in your project, who is?
Do I want to be a CEO?
This is not an automatic “Yes”, since being a CEO is a notoriously hard responsibility.
Just because you like creating things doesn’t mean you’ll find the work of a CEO rewarding, you might instead opt for a structure in which you partner with a CEO who has complementary skills to your own.
There are very few part time CEOs, it tends to consume a lot of your week and your life.
Am I drawn to being what a CEO is, or doing what a CEO does?
This is the basis of Patrick Lencioni’s book “The Motive”: are you drawn to the prestige of the role, or do you actually enjoy what a CEO has to do every day?
Wanting it isn’t enough, if you don’t enjoy the tasks, you’ll avoid them and the business will suffer in the long run.
It might be that you want to be a part of an executive team, but with someone else doing the parts of the job you dislike, freeing you up for your speciality.
What sort of company culture would I like to emulate?
Where would you fit in well?
Which other businesses have built the type of working environment that you’d like to replicate?
Patagonia?
Netflix?
The Government?
If you can’t think of anywhere, it’s time to do more research, or else you risk building a culture that is unlikely to accommodate great work.
What sort of governance and support would help me in this work?
Successful projects have a number of people who help them stay strong.
A CEO is one of those people, but that CEO needs support of their own.
What roles would be restorative, practical and valuable for you?
Which people do you know who would be great examples?
Do you need a board or advisory group?
Do you need a reference group, or trusted advisors?
Who might be a good sounding board?
How do I feel about “Brilliant Jerks”?
A Brilliant Jerk is someone on a team who gets incredible results, whilst also being abrasive, difficult, stubborn or unlikeable.
If you’ve seen The Last Dance, you know exactly what I mean.
Some organisations tolerate Brilliant Jerks, some don’t.
What’s your tolerance like?
Are you the Brilliant Jerk in the project?
What will be the canary in the coalmine?
What will be the early signals that something in the organisation is poisonous?
What will sound an alarm?
Departures of key staff?
Drops in quality or missed deadlines?
Rumours in the hallways?
How can you spot and address these before they have time to compound?
Next we’ll look at how you imagine the work concluding…
What is the right way for senior team members to exit the project?
Very few people design good exit processes at the start of a project, as if they can’t imagine someone leaving.
The reality is, people will leave, possibly even you.
How do you want these departures handled?
Who owns what?
How will the money work?
What terms and conditions are fair to everyone?
Who will own each of the assets we create?
When assets are purchased or created by a team, it can be unclear as to who owns them or decides where they end up.
Who owns the rights to your art?
Who owns your stuff?
Who gets a vote on who else uses these assets in the future?
How will I know when to walk away?
What will be the early warning signs that this project is no longer the right place for you and what you want to build next?
When do you want to cash in, or cut your losses?
What signals or milestones can you choose now that will serve you well in the future?
How do I want to leave the business/project?
Steven Covey always talked about the principle of “beginning with the end in mind”.
Do you want to sell the business?
Do you want to hand control of the project to another person or team?
Do you want to be acquired, even if the work gets shut down by the buyer?
Do you have a set timeframe or valuation in mind?
Finally, let’s look at some tradeoffs and choices…
If I sold the business right now for $10 million, what would I do next?
Let’s say the business was a compulsory acquisition, $10m in the bank, no way of buying it back.
What would you do?
What would you buy or invest in?
How would you spend your time?
Would you work again?
What on?
Something completely different, or something similar?
If I had to get a job somewhere else instead of running this, where would I work and what would I want my role to be?
Let’s say you can’t immediately be a CEO, but you can choose an interesting job.
What companies would you meet with?
What roles and responsibilities intrigue you?
What would you be good at?
What would you like to learn?
What would be in a typical good day?
Am I trying to have my cake and eat it too? Do I actually want two small cakes?
Is this actually one project, or is it two parallel opportunities?
Do they need to be the same project, or are they just both connected to the same person?
Do they support each other or restrict each other?
If you couldn’t have one of them, would you still want to do the other?
Would separating them out give each of them more breathing room?
Do I have fair expectations of myself? Would I expect someone else to handle all the tasks and responsibilities I am assuming?
I know a lot of founders who load so much onto their own plate, an amount they wouldn’t expect anyone else to handle.
Yes, you will care more about the work than anyone else.
Yes, you’ll probably end up with some of the hardest tasks.
The question is, would you advise another founder to take on this much responsibility?
Why or why not?
What would another founder have to score out of 100 to be a “pass mark”?
Can you adopt the same standards for yourself?
Is this a recipe for burnout?
Pretty much every creative and entrepreneurial person you’ll meet will have experienced burnout.
Sometimes it’s by circumstance, sometimes by accident, sometimes by design.
Burnout is exhausting, and it may well happen to you, but it doesn’t have to be inevitable.
I see a lot of people create themselves a recipe for burnout, as if they were finding ways of draining their battery, setting up impossible targets and impossible deadlines.
Could someone else take your proposed recipe and stay healthy?
Am I thinking too small?
While some precautions encourage us to think realistically, that doesn’t mean we have to think small.
What if the scope was bigger?
What if it could grow quickly?
What if some partnerships helped expose your movement to a larger audience?
By all means, don’t fly too close to the sun, but don’t limit yourself to what you can do today.
That’s a lot of questions.
Some of them might be easy to answer, a few might be confronting.
Sometimes a question feels confronting because we hadn’t considered it before.
Other times it might feel confronting because you’re not proud of your immediate response.
You don’t need to justify yourself and your desires, what I’m looking for is the phrase
“…I think I know what I want…”
