I've spent most of my career in conversations with people. Hospitality, where you learn quickly that every interaction is a transaction (and opportunity) of some kind — trust, goodwill, experience. High-volume real estate, where lead generation is a numbers game and the feedback is immediate and potentially brutal. High-ticket EdTech, where you're asking someone to invest serious money in something intangible, and the sale lives or dies on whether they see the value that will follow the progress.
Across all of it, I've learnt that sales is not the dark art people make it out to be. It's not a personality type, and it doesn't require you to become Jordan Belfort — celebrating a close like you've just conned someone. Modern customers are too educated for that. With the internet and LLMs, anyone can get across a topic in minutes. The old tricks don't land the way they used to.
I built the Selling Before You're Ready workshop off the back of conversations with founders — smart, capable people who had built something genuinely useful but couldn't see themselves selling it. Not because they lacked the ability, but because they were missing structure, systems, and the right mentality. The trepidation was the obstacle, not the skill gap. Usually, you just need to start and keep going.
Here are a few key lessons I've learnt to make sales seem less daunting:
The best salespeople don't sell. They coach.
The most effective sales conversations are almost entirely problem-focused. Your job in the first meeting isn't to explain what your product does — it's to make the prospect feel genuinely understood. To demonstrate that you're listening and you've seen their situation before, you know the shape of the problem, and that you understand what it costs them to leave it unsolved.
A great coach wouldn't force a solution on you before understanding what you're looking for. Quality coaching starts with discovering, why you're here, what's being felt, what you've tried so far. A complete picture. Then comes the diagnosis in the form of a tailored solution + demo.
One of the highest performing sales consultants I ever worked with started out coaching a local footy team. He told me:
I still think about this. The best coaches don't impose a game plan on their players — they ask questions until a solution emerges. Your relationship with a prospect should work exactly the same way. Less pitch, more dialogue. Less presentation, more understanding.
Email to Set Up Calls, Calls to Set Up Emails
Early in the sales process, overuse of email can be a trap. It feels safer: you can craft your words carefully, you don't have to handle a live reaction, you can write something once and send it to many. That safety, however, comes at a cost. Email is a one-way mirror. Silence doesn't tell you whether someone is interested, busy, sceptical, or has already moved on. A call tells you all of that rather quickly.
Emails to give your calls a reason, calls give your emails weight.
The same concept applies to your prospects, especially with how easy it now is to paste a sales email into an LLM and generate a low-signal, low-effort response that gives you nothing to work with.
Calls also let you practice the essential skill of holding a sustained conversation about the problem — the closest thing to an in-person meeting short of being in the room. They double as market research, keeping you in touch with what's actually happening on the ground. Pair that with the unmatched feedback loop of a live conversation, and it firmly cements customer calls as one of the highest-leverage activities available to an early founder. At the exact stage when customer feedback is most valuable, defaulting to mass email means choosing comfort over learning.
The practical rule: calls for discovery and relationship-building, email for light touches and solidifying on things already discussed. A visual, customised summary sent after a strong first call — one that reflects back what you heard and maps your solution to their specific situation, with an actionable next step — is one of the most effective sales tools available. Meeting note AI makes this easier than ever. Tools like Granola and Notion AI can transcribe and structure your calls in real time, so the hard work of capture is already done before you sit down to write the follow-up.
The best sales processes use both. Strong written and verbal touchpoints, working together.
Follow-up is where deals actually live
This concept doesn't just apply to sales — it applies to all outreach. Those who win are almost always the ones who follow up consistently and track their pipeline meticulously, as much as Hollywood would like us to believe there's a magic closing technique. The fortune really is in the follow-up. It's the least glamorous part of sales and the most important.
And I get it: where does consistent follow-up end and being the person who just doesn't take the hint begin? The answer is in the foundation you lay earlier. Stay curious, don't always have the deal in mind, and vary your touchpoints — LinkedIn, email, calls. A "not right now" or "not interested" is actually useful signal. It might just mean they're not your customer yet, or not at all. Either way, it's far better than a pipeline full of maybes — that purgatory will cost you more time and energy than a clean no ever will. A solid batch of nos tells you something. A hundred maybes tells you nothing.
Every meeting should end with an explicit next step — and contrary to popular belief, this can be low-touch. "I'll be in touch" is fine, as long as you actually follow through. Think of it like catching up with an old friend: without a concrete date in the calendar, things drift. A conversation without a next step is just a conversation.
When a prospect goes quiet, you haven't lost them yet. Use what you know — the pain points they shared, the objections they raised — to re-engage in a way that shows you were listening. If a direct ask goes unanswered, pivot to asking for feedback instead. It's a lower-commitment request and it often reopens the conversation.
A "no" should almost always become a "not right now" with a specific future date attached. People's circumstances change. Budget cycles turn over. Priorities shift. If you've genuinely helped someone understand their problem better, you've built goodwill that survives a missed close — and that door stays open. The foundation will always be there.
Rejection isn't the end of the data
Sales involves rejection. That's not an insight. But how founders process rejection often determines whether their sales function lives or dies. Sometimes, your instinct is to treat a "no" as a verdict — on the product, on the idea, sometimes on yourself. The more useful frame is to treat every "no" as an unanswered question.
And most of the time, it isn't a no — it's a no right now. Circumstances change. The important thing about getting a no is understanding why. Was it timing? Budget? Is this genuinely a low-priority problem for them, or is it a high-priority problem they don't yet believe you can solve? Each of those answers points somewhere different. A "no" you understand is a piece of market intelligence. A "no" you accept without curiosity is just a closed door.
Think of rejection like weather. You can't stop it and you can't take it personally, but you can dress for it. A process gives you that — something to revisit when a conversation goes cold, so that one bad day doesn't knock you off course for a week. Social literacy plays a part too. Know when to push and know when to move on gracefully. Some doors are worth knocking on twice.
Sales isn't a dark art. It's a series of conversations, each one building on the last — with structure underneath and curiosity driving it forward. Most founders who struggle with sales aren't missing talent. They're missing a system and the willingness to start. The willingness to start is on you. The system is learnable.
The best time to build it was before your first customer. The second best time is now.
Here's my sales workshop with the Q&A cut out.
If this resonated, we run community workshops that go deeper on all of it — and well beyond sales. If you're an early-stage founder looking for a space that takes this stuff seriously, come find us.
Or drop me a line at [email protected] — always happy to chop it up about your current process and where you're at.
