After coaching hundreds of founders through top fellowships and university programs, I've noticed that asking the right questions can completely change your path to success. Here are the five most powerful questions I've gathered from 15 years in tech and working with successful founders. They're deceptively simple, but they'll give you the clarity you need to move forward with confidence.
Grab a notebook (or download our free workbook below) and let's walk through this together.
We often think we understand the value we're delivering to our customers. We craft our product carefully, adding features we believe will solve their problems. But here's what's fascinating: sometimes the thing that makes customers desperate to pay isn't what we expected at all.
Think about that moment when someone sees your product and has that "shut up and take my money" reaction. What exactly triggers that response? Sometimes it's not even your main feature – it might be something you've created on the side, or an aspect of your solution you haven't fully explored yet.
If you're finding it difficult to answer this question quickly, it's worth pausing your other work and spending more time talking to customers. You need to understand their world completely - how they think about their problems, what really frustrates them in their daily work, what sort of budget they have available, and most importantly, what transformation they're looking for.
When you really understand your customers, you should know their biggest pain points so well you could explain them in your sleep. All those customer conversations you've had over the previous months should paint a clear picture. If they don't, that's your signal to go back to customer research and have more first-hand conversations.
This question helps turn vague dreams into concrete plans. Your goal might be finally paying yourself a proper salary, updating your product with new features, or bringing on more team members to help you grow. Whatever it is, we can break it down into real numbers.
Here's where a simple back-of-the-napkin calculation becomes incredibly powerful. Write down what you need in monetary terms, look at your product price, and work out how many sales you'll need. If you need to make £100,000 and your product costs £1,000, you need 100 sales. Suddenly, your target becomes tangible.
But let's get even more practical about these numbers. For an online shop, typically only about 3% of visitors end up buying something. If you're working with repeat customers, you'll need to think about lifetime value. Even with this most basic approach - annual goal divided by product cost - you'll get a number that helps focus your efforts.
If your target is 80 sales, you might think, "Right, I can find 80 people who need this." If you need thousands of sales because you're working with a lower price point, you might start thinking about partnerships and where to find groups of potential customers in larger numbers.
Most founders start with a clear picture of their target customer, someone they're genuinely passionate about helping. But when we dig deeper, there's often more to the story. Many founders are trying to prove a point, working towards financial independence, or creating a better future for their family. Understanding your true motivation matters because building a business is challenging, and you'll need this deeper purpose to keep you going.
Your customers should absolutely be part of this equation. Whether you're building a direct-to-consumer product or creating a B2B solution, think about the real impact you want to have. Perhaps your software helps businesses work more efficiently, which means their employees can spend more time with their families. Or maybe your product helps people feel more confident, more capable, or more in control of their lives.
Having this clarity makes your day-to-day decisions much easier. When you truly understand who you're doing this for - both your customers and your personal motivations - you can make choices that align with these goals. It becomes simpler to say yes to the right opportunities and no to the distractions.
This question typically triggers two very different responses. Some people immediately start listing every task on their to-do list, feeling overwhelmed by all the things they haven't done yet. Others have that instant "oh no" moment - they immediately recognise that one big thing they've been avoiding.
If you're in the first group, making lists of all your tasks, take a step back. Think bigger. What's that elephant in the room you've been pretending doesn't exist? What's that thing that makes you think "no, no, no, I'm not listening" whenever it comes to mind?
Usually, it's something significant, and it's secretly draining your energy without you realising it. When you're trying to build a business, you need all your mental resources focused on moving forward, not being slowly sapped by that looming, invisible worry in the back of your mind.
The good news? Simply identifying what you're avoiding is often the hardest part. Once you've named it, you can assess how important it really is. Sometimes you'll realise it wasn't as crucial as you feared. But more often, if it's causing such strong feelings, it's probably important to address.
Set aside a full day to tackle it - yes, a full day. When we're doing something new or difficult, everything takes longer than we expect. There will be lots of searching for answers, trying things out, and learning as you go. That's completely normal. Remember, it's okay to be rubbish at something new - everyone starts somewhere.
Building a startup is often compared to riding a rollercoaster, and with good reason. The highs are brilliant, and the lows can be crushing - and they come at you faster than you might expect. What makes startup life particularly challenging isn't just the ups and downs, but how quickly you cycle between them.
This is why having a strong support network is crucial. Your startup simply can't exist without you - if you're not pushing forward, nothing happens. Nothing will magically appear or grow on its own. Taking care of yourself isn't just nice to have - it's essential for your business.
Think about who you turn to when you've had that difficult day, when you've faced multiple rejections, when it all feels a bit too much. Maybe it's a group of fellow entrepreneurs who understand exactly what you're going through. Perhaps it's friends who can make you laugh and help you forget about work for a while. Or it might be family members who've always believed in you.
I've created a free workbook to help you work through these questions properly. It's not just about reading through them - it's about taking the time to reflect and really engage with each question. The workbook gives you space to think, reflect, and revisit these questions regularly as your business grows.
Download it now and set aside some proper time to work through it. These questions might seem straightforward, but they have the power to transform how you think about your business and give you the clarity you need to move forward with confidence.
Building a business is challenging, but having clarity in these five areas makes everything else easier. There are no right or wrong answers - what matters is being honest with yourself and using these insights to guide your journey.
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