66 Questions That Might Be Good For Us To Talk About

If we have a session coming up and you’re trying to remember what you wanted to talk about, then this is the cheat sheet for you.
These prompts are starting points; the list isn’t called “66 Mandatory Questions” nor is it called “66 Questions We Will Definitively Answer In One Go”.
Here are some thought-provoking options, take one or two or make a better question that genuinely excites or scares you.

Whatever is on your mind today

Some of my favourite coaches would argue that this is consistently the greatest use of our time together.
Their rationale is that if we DON’T address what’s on your mind, all the other work won’t really sink in since you’re preoccupied.
I partially agree – it’s a great starting point, and I also want to make sure that we cover what we agreed to cover at the outset of our sessions.

“I’ve been thinking about a new opportunity, and want to think it through in detail so that I’m not rushing or missing something in a blind spot…”

“I have an annoying situation that has come up…”

“I have a burning question, something struck me the other day…”

Whatever you’ve been thinking about but stalling

Perhaps there are topics that aren’t urgent or front of mind, but have been on the back of your mind for some time, and are becoming a source of frustration.
This might be a lingering issue, a curiosity, a new project, or something that you know you’re supposed to do but aren’t getting done.
Bring it to us.
You’ll instantly reduce the size of the issue by getting it out of your mind and onto the proverbial table, and as they say, a problem shared is a problem halved.

“I’ve been wanting to try this thing, but I keep talking myself out of it…”

“I’ve been wanting to try this thing, but can’t get proper information or a straight answer about it…”

“I’ve been wanting to try this thing, but I know it has to be perfect…”

What are our options for growth

There is rarely only one good option for growth.
But when you’ve heard about someone else’s tactic that worked for them, it’s tempting to see that as the one and only way forward.
By zooming out, lots of options will appear, and by looking at them objectively there’ll probably be a few intriguing options.
Some will be challenging, some will be quick wins, but good ideas survive competition, so let’s create a few competing options and you can choose.

“What are some new markets we could explore, even where we might have an advantage?”

“How might we make more revenue in our business?”

“How might we make more margin in our business?”

“What else could we expand into, like new products/services, or new industries?”

“I feel like we need to pivot, what are some big pivots or even small pivots we should be considering?”

“We’re interested in a partnership with XYZ, but want to go about it the right way…” 

Bottlenecks in the business that are restricting your growth

If there are bottlenecks in your business, and there probably are, then growth will make them worse.
e.g. if you’re the only one who can talk to new customers, a growth campaign will swamp your calendar and create problems.
The time to address these is before a situation becomes urgent.
Sometimes we need a new system, a new hire, new thinking or new habits.
Some of these can be bought, more often though the painful part is changing your behaviour and not reverting to unsustainable shortcuts.

“I want to reduce the amount of the business that is dependent on me…”

“I’m wary that we’re dependent on 1-2 key customers…”

“We only have a limited menu to offer people and I suspect it’s hurting us…”

“Are our margins wide enough for us to be able to grow?”

“Will we need to raise money for the next phase of growth, in what format and how much do we need?” 

Building and supporting your team

I don’t think we’re HR specialists as such, but people like talking about their growing team and their excitement/concerns so it comes up a lot.
Getting this right is extremely critical for your company’s growth, and getting it wrong is extremely expensive and time consuming – both for keeping the wrong people or having to re-advertise a role.
It’s good to talk to a trusted advisor about your thought process and your questions, your situation might not be as unique as you think.

“We’re about to hire someone, here’s what we’re thinking…”

“How do we set and keep a healthy team culture without us being in every meeting?”

“How do we keep everyone on the same page if we’re in different locations?”

“Can we save time and stress with better systems and habits in place?”

“How do I delegate properly so not every headache comes to me specifically?”

“How do we grow and retain our best people?”

Zero to one brainstorming

Lots of people are good at taking a big collection of 30+ ideas and either sorting them out or narrowing them down.
Fewer people like creating the big collection of 30+ ideas, especially if they’re busy.
Interestingly, those who grumble or hesitate to start brainstorming are often great at joining a brainstorm once it has picked up some pace.
Together, we can get a lot of ideas out in the open without squashing your enthusiasm.

“I’m looking to make a big list of all the different types of content that we’d be well positioned to create for our brand”

“Can we brainstorm who we might approach next, who would be open or even happy to hear from us?”

“What are some of the ways we can either save money or reduce our financial risk?”

“We have a lot of ideas, can we look at how to narrow down a top 3 so that we don’t go around in circles?” 

Turning interesting ideas into useful prototypes

Ideas are great, but they can become stuck or frustrating if you don’t have a way of making them feel real or like there’s some momentum.
Prototypes (and their younger cousins, Pretotypes) are excellent for advancing your ideas, making them real, highlighting strengths and weaknesses, and giving customers something that they can react to.
Prototyping does require some patience, a bit of budget and a thick skin; some of your ideas are going to flop and we’ll keep it moving without wallowing in self-pity.
But in return, prototyping makes for better ideas, it saves you money and it prevents you from investing in the wrong ideas.

“Can we mock up our ideas from last week?”

“What sort of prototype can we build that we could then take to customers or investors?”

“What can we build that’s under $500 and can be validated in under a month?”

“Can we make a new iteration based on customer feedback?” 

Running cheap and effective tests and experiments

Prototypes and pretotypes are both forms of tests, which are great for iteration and validation.
But there are other forms of test too – gaining insights around Desirability, Feasibility and Viability without needing to go all-in.
Tests are confronting but they are so good for you.
They draw out bad news and they draw out surprising good news too.
But tests take some discipline and creative thinking, so it helps to have a “sparring partner” to help you work out a fair and valid experiment.

“What should we test next?”

“How would we even test something like this?”

“How do we run a test like this if we hardly know any customers in this field?”

“How many tests do we need to run to have a valid conclusion, and what counts as success or failure?” 

Designing and improving customer journeys

If you’re looking for a quick win, the “Five E’s of Customer Journeys” are a great place to start.
Each “E” describes a different stage of what customers go through when they research, purchase and remain loyal to your brand.
They are Entice, Enter, Engage, Exit and Extend.
For each, there are so many case studies to borrow from, taking tactics to improve your own customers’ experiences. 

“What are the Five E’s in detail?”

“Can we review which ones we’re already doing well and which ones need more attention?”

“How do other brands in our field attract, serve and retain their best customers?”

“What about brands in other markets or other industries, who else can we learn from?”

“How do we improve these steps, and how will we know the changes are working?” 

Financial choices and their consequences

You are a finance person, whether you realise it or not, since you’re making decisions that affect your company’s money.
You are already making choices with consequences, and by understanding those choices in more detail, you’ll feel better and clearer about what you can live with and what you’d like to change.
e.g. changes to your pricing or costs, changes to the number of customers you want to serve, changes to when you commit and spend money, changes to your team, changes to your supplier arrangements, etc.
The first step would be to understand how each of these works, what the terminology means and what this looks like in your specific niche.
The second would be to map out how money flows into, out of or remains in your business.
The third step is to model prospective changes, to see how much of a difference a change would make to your overall profitability.

“Can we look at our pricing?”

“I want to understand our costs to see if there are ways we can save money and offer a better experience”

“Should we be outsourcing more or doing more ourselves?”

“When will we break even and how far away is that from now?”

“What’s the smallest change that would ruin our profitability?” 

Sales philosophies and methodologies

Similar to finance, you are a salesperson, whether you realise it or not, since you’re making decisions that affect your customers.
You are making trade-offs and changing how customers perceive and interact with your brand, and so you want to be comfortable with your chosen trade-offs.
e.g. product and service design, marketing, follow-ups, setting prices, designing your menu of offers, etc.
Some entrepreneurs are deeply uncomfortable with the idea of sales, associating it with sleazy car salesmen and high-pressure tactics.
That’s a fair association since that’s who a lot of sales books seem to be written for, but it isn’t true for startups.
We can work together on a sales philosophy and methodology that you genuinely like, and which gets better results for your customers. 

“I hate the thought of ‘selling’, how can I get my head around it?”

“What do other successful startups do in their sales processes?”

“How do we find more customers and make better offers?”

“How do we follow up with people without feeling too pushy?”

Options and trade-offs around investment

You might not need to raise money, but it’s worth thinking about the pros, cons and range of options available for your specific situation.
The right investment at the right time can help you grow faster, grow sustainably and set yourself up with the right team.
The wrong investment at any time can cause tension, resentment, financial instability or even lead to closing the business.
No investment is perfect, but in several scenarios the good massively outweighs the bad, so long as you’re aware of how the mechanisms work.

“Should we raise money or bootstrap this year?”

“What do investors look for and how do we impress them?”

“What would raising money allow us to do? What does that cost us?”

“How do investments work in our field? Who invests and what do they expect in return?”

“If we don’t raise money, what might we do instead? What does that give us in the long run?”

Discomfort and narratives around your own success

For a lot of people, whenever they have to do something that they know is important, they feel an inner “resistance” that starts finding reasons not to do the work.
It’s a voice of concern that says “don’t run the ad” or “don’t call that person” or “don’t hire anyone yet, what if sales slow down?”.
Ultimately, this feeling of resistance is trying to keep you safe by keeping you small and invisible, to avoid pain, shame and sad narratives.
That’s why we have to push past it, because staying small is also frustrating you.
Resistance kills new businesses, but noticing the resistance is a sign that you’re probably working on something worthwhile.
Talking about it massively diminishes its power and credibility, and lets you see your situation with fresh eyes. 

“I am hesitant about the new phase of growth because…”

“I feel like I want to wait until… then I’ll be ready to…”

“The problem is I am not a real … so I can’t … without…, right?”

“If this succeeds, how will I handle the expectations of my family?”

“I’m concerned that if this works, it will force me to…” 

Pitching to different audiences

For some people, any form of public speaking is incredibly daunting, let alone pitching your business to investors, partners or customers.
But you’re going to be pitching all the time – to friends, clients, suppliers or funders – and you naturally adjust your conversations to suit each scenario.
The same goes for your pitch; we can form different length presentations with different emphases, depending on the audience and intent of the meeting. 

“How do I put together a pitch for a competition?”

“I’m talking to some VCs, what do I need to include in my presentation?”

“Can I practice my elevator pitch?”

“We’re applying for a loan, what questions should we prepare for?” 

Action planning and goal setting

Once you know what you want to do, we need to make sure that you have systems and incentives to make consistent progress.
This is called action planning – identifying what needs to happen, by whom, in what timeframe, and then what happens after that.
Good goals help incentivise, motivate and track your performance, adding accountability and a sense of progress. 

“What can we do now that will make everything else feel easier?”

“What do we need to do straight away?”

“How will we know it’s working?”

“What should each of us take ownership of, and accountability for?”

“If we hit… can we then buy…?”

By all means, make up your own question, put it in your own words, as direct or convoluted as you like.
The aim of our work is to properly understand you and what you want, so that we can be as valuable as possible.
We will always tell you when we’re out of our depth or recommend another specific expert for important questions, and can also highlight where we are the exact right people for certain types of conversation.
Remember what Joseph Joubert said:
“It is better to debate a question without settling it, than to settle a question without debating it”.