The Qs Founders Are Afraid To Ask
The questions I hear most often from founders usually start with: "This might be a stupid question, but..."
It's never a stupid question.
Here's what I hear all the time:
"Should I be profitable by now?"
"Is my business growing fast enough?"
"Do we have enough cash?"
"Is my gross margin healthy?"
And my answer to every single one is the same: it depends.
Why "It Depends" Isn't a Cop-Out
Finance people love saying "it depends" because it genuinely does. The problem is that most founders don't get help finishing that sentence. They're left with the vague sense that they should know something they don't, which makes them even less likely to ask again.
But here's the thing. The specificity of your situation is where the useful answers live.
Take profitability. Whether you should be profitable right now depends on a load of factors: Are you in investment phase? Have you just hired three people? Is your business capital intensive? Are you building something that requires upfront spend before revenue materialises? There's no universal timeline.
The same goes for growth. Is your business growing fast enough? Depends. What are you actually building? What do you want? Fast growth for the sake of it can break things. Sustainable growth that matches your capacity might be smarter, even if it looks slower on paper.
The Real Cost of Not Asking
According to 2025 UK business statistics, 90% of startups fail, with 29% running out of cash and 71.1% failing within the first 3 years. Only 39.4% of small businesses reach the 5-year mark. While there are many reasons businesses fail, financial misunderstanding is consistently near the top of the list.
In late 2025, more than 60% of small businesses reported being paid late by bigger companies, costing UK SMEs an average of £22,000 per year in delayed working capital. When you combine cash flow problems with unclear financial foundations, strategy becomes guesswork.
The questions you're afraid to ask are usually the ones worth asking. They're not stupid, they're specific to you. And specificity is where clarity lives.
The Questions That Matter
Here are the questions I hear most often, and what "it depends" actually means in practice:
Should I be profitable by now?
Depends on:
Investment phase (are you building foundations or scaling?)
Recent hiring (have you just brought people on?)
Capital intensity (do you need to buy stock, equipment, property?)
Business model (are you SaaS with deferred revenue, or retail with immediate margin?)
Growth strategy (are you prioritising market share or profit margin?)
If you're a year-old tech startup still building product, probably not. If you're a three-year-old consultancy with stable clients, quite possibly yes.
Is my business growing fast enough?
Depends on:
Your actual goals (what are you building towards?)
Your capacity (can your current team handle more?)
Your sector (what's normal for your industry?)
Your funding position (do you need to show hockey-stick growth to investors, or sustainable progress to a bank?)
UK GDP grew by 0.1% in Q3 2025, with real GDP estimated to be up 1.3% compared to the same quarter in 2024. Growth remains modest, so if you're outpacing that, you're already ahead of the economy. But "fast enough" isn't about comparison, it's about whether your growth rate supports your specific goals.
Do we have enough cash?
Depends on:
Runway (how many months can you operate at current burn rate?)
Upcoming invoices (what big payments are due, and when?)
Payment terms (are you paying suppliers faster than clients pay you?)
Seasonal patterns (do you have a quiet January but busy September?)
Growth plans (are you about to hire, or buy stock, or sign a lease?)
Cash flow is the thing that kills businesses, not lack of profitability. You can be profitable on paper and still run out of money if your timing's wrong.
Is my gross margin healthy?
Depends on:
Sector (retail might be 40%, SaaS might be 80%)
Stage (early businesses often have lower margins whilst building scale)
Business model (are you selling products or services?)
Pricing strategy (are you competing on price or value?)
There's no magic number. But if your margin is shrinking and you don't know why, that's a problem.
Why Founders Don't Ask
There's a particular kind of imposter syndrome that comes with running a business. You're the expert in your field, the person everyone looks to for answers. Admitting you don't understand your own numbers feels like admitting you shouldn't be doing this.
But here's what I've learned after 16 years in finance and working with hundreds of founders: the best founders are the ones who ask questions.
The ones who sit in a meeting and say "I don't actually understand what that means, can you explain it differently?" are the ones who end up making better decisions. Because they're operating on clarity, not assumptions.
According to the ONS Business Insights Survey in late December 2025, falling demand remains the most common concern for businesses at 18%, whilst 15% cite taxation as their main concern. In an environment where 95% of businesses are trading (84% fully, 11% partially) but uncertainty remains high, flying blind isn't an option.
What You Actually Need to Know
You don't need to become a finance expert. You don't need to love spreadsheets or understand accrual accounting. What you need is to be able to answer these questions:
Can I afford to hire this person? (Not just salary, the full cost)
Which parts of my business are actually profitable? (Not revenue, profit)
Is my pricing right? (Are you leaving money on the table, or pricing yourself out?)
Do I have enough cash? (For the next 3 months, 6 months, 12 months)
What happens if X goes wrong? (Lose a client, supplier price increase, delayed payment)
If you can answer those, you're in a better position than most.
How to Get Clarity
1. Ask the "stupid" questions
The only stupid question is the one you don't ask because you're embarrassed. Finance people (the good ones, anyway) want to help you understand. If someone makes you feel stupid for asking, they're not the right person to be working with.
2. Request explanations in plain English
"Can you explain that without the jargon?" is a completely reasonable thing to say. If someone can't explain a financial concept in normal language, they probably don't understand it well enough themselves.
3. Use specific examples
Instead of "How do I improve cash flow?", try "We're paying suppliers in 14 days but clients pay us in 60 days, what can we do about that?" Specific questions get useful answers.
4. Challenge the "it depends"
When someone says "it depends", ask them to finish the sentence. "It depends on what, specifically?" Push for the actual factors that apply to your situation.
5. Keep asking until it makes sense
If you're nodding along but still don't really get it, keep asking. "Can you give me an example?" or "What would that look like in practice?" are both completely valid follow-ups.
The Clarity Is Worth It
I worked with a founder last year who'd been operating for three years without really understanding their numbers. They knew revenue was growing, but couldn't tell me if that growth was profitable. Turns out, one of their product lines was actually losing money once you fully costed it (factored in the time it took to deliver).
We phased out that line, focused on the profitable categories, and within six months they'd increased profit by 40% whilst working less. The business hadn't fundamentally changed. They just finally had clarity on what was actually working.
That's what happens when you ask the questions.
Where Sure Thing Fits
This is precisely why we exist. Not to make you into a finance expert, but to help you finish the "it depends" sentence with clarity that's specific to your situation.
We work with businesses that need someone who can:
Translate numbers into decisions
Answer the questions you're afraid to ask
Give you clarity without making you feel like an idiot
Help you understand what's actually happening in your business
Because the questions you're sitting on, the ones you think might be stupid, are usually the most important ones to ask.
If you're sitting on questions you're afraid to ask about your numbers, ask them. The clarity is worth it.
