Even the best hairdressers do not cut their own hair, and the best dentists don’t fix their own teeth.
No matter how good your business is, there is always benefit in bringing in new perspectives and ideas, especially if it’s someone who knows how you can get more of what you really want.
These people are coaches – and they can be professional or amateur, so long as they past one simple test: Can this person make me better?

Good coaches are great at three things:
1. They are excellent listeners, who ask you what you truly want rather than telling you what you should want.
2. They ask great questions, which make you see your situation from new perspectives.
3. They are brilliant planners, who help you set inspiring goals and then break them down into manageable pieces.
Each of these skills are valuable, but combined together they are revolutionary.

When a coach is listening to you, they’re working out what sort of question will help clarify your situation, articulate your preferences and show you your options.
Coaches often collect good questions, so that they can recall them when deep in conversation in the future.
Here are eight helpful styles of question you can use in your own coaching work.
Each of them is valuable under the right circumstances, you can either borrow these specific questions or create your own based on what seems relevant.

Guiding Questions - drawing out your vision and the intent of your work
We want to understand how the entrepreneur will make decisions in the future.
To do this, we can ask questions about their origin story, their past decisions, the make-or-break sliding doors moments that shaped the business as it stands today.
We can also ask about their vision and hopes for the future, what they want to be known for, and how they’ll know when to walk away from an opportunity.

This mix of past and future is important – the past is relatively concrete, while the future is still up in the air.
Please note, this process can help people “rewrite” or “reframe” their past, which can be cathartic or a chance to misremember what actually happened.
Memories are not facts, and maybe that’s ok.

Examples:

· What are my signature strengths?

· What is my “Cathedral” – the project I may never see completed?

· Am I drawn to what a CEO is, or what a CEO does?

· Am I looking for what is working, or what is broken?

· What is my exit strategy?

· Where have I made choices that were difficult in the short term, but valuable in the long term?

Lucrative Questions - improving your financial situation, sometimes in unexpected ways
There is no ceiling on what a business can earn, and yet we act like our company can’t go much higher.
Lucrative questions are designed to reveal opportunities for financial growth, be it through new markets, new customers, new products and services, revamped prices, higher consumption, lower churn, lower costs, insourcing or outsourcing, etc.
There is no obligation on the entrepreneur, all we’re doing is uncovering options and projects, then letting them tell us which ones intrigue or inspire them.
Lucrative questions aren’t motivated by greed, but by sustainability and the desire to do more of the work that matters most.

Examples:

· Could we boost our market share?

· Could we create a higher value product or service?

· Could we completely drop some expenses?

· How might we make money while we sleep?

· Are we taking steps to retain our most valuable customers?

· Can we attract more revenue by moving our paywall?

Ugly Questions - realisations, blind spots and the decision to speak your truth
Ugly questions are my favourites, because they help us confront unpalatable truths about what we really want.
They’re not ugly for the sake of being ugly, but because we don’t like how the answers make us feel.
That’s exactly why we need to bring these questions out into the open.

There’s often an initial hurdle or resistance to overcome, but once that’s out of the way, people seem relieved to be having the conversation.

Examples:

· Should we drop two or three projects in order to focus on the real winner?

· Do we need to pivot or persevere?

· Do we actually want two small cakes?

· Gun to my head, can I compress the next 10 years into six months?

· Am I afraid of selling? Why?

· Who is not my customer? Whose approval has been difficult to earn?

· Am I hunting field mice or antelope?

Beautiful Questions - possibilities, removing limitations and the decision to own your strengths
If ugly questions are about our reality, then beautiful questions are about possibilities.
The future holds lots of potential paths for us to take, and we want to begin describing what these might look like.
We don’t want sickly sweet optimism, just a chance to evaluate our options without our old limiting beliefs.
That’s the secret of beautiful questions – they help us see the weird filters and expectations that keep us small.
We can address these mindsets and restrictions, then re-examine our options with fresh eyes.

Examples:

· Do I want to be done or do I want to improve?

· If I can’t create the thing I dream of, can I at least create the thing I’m capable of making?

· Am I courageous enough to abandon the past?

· How can we become the company that would put us out of business?

· What if this isn’t a “yes or no” decision?

· What if this was easy?

Systems Questions - structures and assets that free up your time and headspace
Building a business means building something that can work without you.
An entrepreneur needs to design systems that can ultimately replace them, and it is unlikely to happen by accident.
We want to start this thought process early, nudging them to create systems, define roles, train new staff and eventually make themselves redundant.

Examples:

· Am I building a business or a job?

· What assets can I start building today that will become valuable in 10 years’ time?

· What are the bottlenecks in the business? Am I idolizing these bottlenecks?

· Do I want to be a soloist or a conductor?

· Can I capture the magic of the business in a series of high quality checklists?

· Do we have a way of smoothing out our demand cycles?

Self-Care Questions - taking care of people and the soul of the business
While they might say all the right things, a lot of entrepreneurs don’t actually practice proper self-care.
They work themselves into the ground, practice negative self-talk, put themselves last, and create key person risk for the business.

These questions help reframe the entrepreneur as an asset that the business needs to maintain, a claim that’s hard to refute, and helps them diagnose areas in which they could better protect themselves from burnout.

Examples:

· Do I need a running mate?

· Am I being let down by my “battery”?

· Do I want to be right or do I want peace?

· Do I genuinely trust the team I have today?

· Where have I been at my best? What drove me or inspired me in those times?

· Given all the changes yesterday, what is my job today?

Outcomes Questions - doing good, but better than before
It’s one thing to set a grand vision, but another thing to track your progress in a meaningful, measurable way.
Business owners might generate financial performance reports every quarter, but how do they track their other goals?
It’s helpful to have a sounding board to discuss social outcomes, targets and non-financial metrics.

Examples

· How will I measure success?

· How will I know if we’re making a difference?

· Am I passionate about a particular tool/mechanism, or am I passionate about helping a particular group of people?

· Could I make something great for the sake of it being great?

· For my desired behaviour change to occur, who has to do what differently?

· If we disappeared tomorrow, who would miss us?

Action Planning Questions - grounded, practical decisions about the next step
Coaching conversations can spark big ideas, grand visions and sweeping changes.
If these remain theoretical, we’re unlikely to see any true change or improvement.
If the journey of a thousand miles begins with a single step, then the reinvention of a business begins with a single decision and action.
Our job is to be great at planning those first actions.

Examples:

· What if I allow myself to begin anywhere?

· Is it time to be a hummingbird or a jackhammer?

· What are my Obama O’s?

· Can I put a bounty on my dreaded tasks?

· Can I lower the difficulty on this?

· Do I need a technical solution or 20 seconds of great courage?

· Can I take smaller bites?

How You Can Incorporate These Questions
My suggestion is to keep these themes but re-create your own specific questions – you know your audience better than I do.
Choose questions that are natural, relevant and which fit within your typical conversation.
Reading out pre-prepared questions makes for a contrived moment and lets the other person put their guard up – unless you make a game of it.
This allows you to throw someone else under the bus, you can blame their questions for awkward moments if they fall flat, and makes the pointed questions feel less personalised.

I think questions are like Lego bricks – little colourful pieces that you can combine to make interesting things.
There are two ways to make better Lego creations:

1. Take unique Lego pieces from different kits – like pirates or police cars or Jedi or Harry Potter wizards.
This is like reading diverse books, listening to interesting people in other fields, and actively broadening the ideas you consume.

2. Practice building weird and wonderful things out of Lego.
This is the “free play” or “design constraints” that let you experiment with different structures and purposes for each brick.
You can use your imagination, and learn from what has worked for you in the past.
This is like learning from your past coaching sessions, deliberately changing your approach and measuring which combinations of questions get good results.

While you create your own lists, feel free to borrow any of mine, and keep track of any questions or ideas that lead to turning points in your conversations – they’re likely to come in handy again in the future.