How I learned to sell better after failing my business 7x

December 27, 2023

Ever felt like your big idea was about to take off, only to hit a wall you didn’t see coming? That was me with my second startup, a B2B SaaS that helps tuition centres improve learning for students. The product was solid — or so I thought.

10 years into entrepreneurship and sales, I am here to share my journey and hopefully some learnings that can help you 1) identify a problem, 2) build and 3) sell a product that people are willing to pay for.

Here are 3 key shifts that have helped me become a better salesperson.

1. Mindset: From what is in it for me → what is in it for them?

The biggest mindset shift about sales was this: sales is not about pushing things onto others but identifying gaps to help prospects fulfill their needs.

As a business owner, I was convinced that my product would solve my prospect’s problem. This led me to focus on the features of the product, without not paying enough attention to what the customer truly needs.

This meant that as a novice salesperson, I found myself pushing for the sale too hard, transforming the process into more of an interrogation than a productive exchange.

Throughout the years, I’ve learnt that a more effective approach involves providing contextual reasons and framing the importance of each question. It’s not just about bombarding prospects with questions; it’s about guiding them to reflect on insights they might not have considered.

Asking deep, insightful questions prompts prospects to reflect on aspects they might not have consciously thought about.

The lightbulb moment happened when I started focusing on bridging the gap between the customer’s goals and what my product could deliver.

It dawned on me that sales isn’t about pushing—it’s about guiding people to make decisions that align with their needs. My job as a salesperson was not to sell, but to help others make a decision that helps them achieve their objectives.

With this mental shift, I transformed from a “pushy salesman” to someone who wanted to understand my prospects’ needs, delivering value in the form of genuine recommendations.

Book Recommendation: Gap Selling


2. Mood: From feeling fearful feeling excited

Ever felt butterflies in your stomach before a prospect meeting? As someone who has done sales for 10 years, I assure you that fearing rejection is normal.

What I’ve also learnt is that this fear happens because I don’t understand the prospect’s needs sufficiently to be confident that what I have can or cannot be of value.

Imagine this: if your role was to gift someone a brand new Ferrari or $10,000 in cash, would you be fearful? Probably not. This is because you already know that these are things of value to anyone.

The reason why you are afraid is because on some subconscious level, you don’t believe that you are adding enough value – either through 1) what you are selling or 2) your abilities.

If it is about what you are selling, your next step is to understand the product or service and its benefits better, and how it can serve your prospects’ needs better. This will help to boost your conviction and confidence in the product. Without conviction in what you are selling, it is near impossible to sell properly.

If it is about your ability, analyse how you are currently showing up for your meetings. Remember: your ability to sell well rests on your ability to deliver value.

If you currently view your client interactions as lens of a competitive sport, where you have to outmuscle your prospect, then of course you are nervous!

But if you view it from the lens of giving your prospect a great experience, giving them the best information and knowledge you have based on their needs, and serving them to the best of your abilities, then the anxiety will most likely would go away because you KNOW that you are giving value.

3. Role: From prospect’s slave valuable partnership:

Contrary to the common belief in sales, the customer is not always the king. Salespeople do not need to be subservient as well, or catering to every whim of the prospect.

I repeat: Being a great salesperson isn’t about becoming someone’s yes-person; in fact, it’s about knowing when to say no.

A valuable salesperson is far from a yes-man – they hold their ground. I learnt that in sales, collaboration is in the prospect’s interest, but you don’t have to oblige if the give-and-take isn’t mutual. Your time matters too.

Remember: The more you value yourself, the more customers will value you. Sure, there might be a power imbalance at the beginning, but the goal is for it to gradually shift towards equilibrium, evolving into a partnership where both sides support each other to achieve a common goal.

4. Surprise, surprise: Relationships don’t matter as much as you think

In sales, relationships aren’t the deciding factor they’re often made out to be. Likeability, while pleasant, can’t substitute for expertise and service. Expertise puts dollars in your pocket, not relationships.

Having a good rapport can open doors, but the ultimate clincher is still your expertise. If they fancy you but you fall short on value, they’ll kindly decline and maybe give you some nuggets of advice.

If there’s mutual liking and you bring value, you’ve got yourself a sale and maybe a celebratory drink.

Even if they’re not your biggest fan, but you provide value with your expertise, they’ll still buy from you. Credibility as an expert is the true sales driver—people want to buy from those who know their stuff.

So, instead of solely focusing on relationships, channel your energy into building credibility as well. After all, when your focus is on genuinely helping and delivering expertise, you’re pushing forward in the right direction.

Applying these techniques helped me close my first client

To recap, these are the exact steps I took to supercharge my sales:

  1. Shift my mindset from closing the deal, to delivering value for prospects
  2. Shifting my mood from fear to excitement because of the value I get to deliver
  3. Become a valuable partner for prospects
  4. Become a credible expert in what I sell

Another key lesson was the importance of setting expectations when diving into the question-and-answer phase. Rather than jumping right in, it’s more effective to start by outlining what you’re aiming to achieve. This ensures a smoother and more collaborative sales conversation.

The sales framework that I used now to double my results:

So, after learning all these, this is the new framework that I used:

First off, every meeting kicks off with a clear objective. I like to set the stage by laying out expectations—I’m here to understand their needs, and it’s going to be a two-way street where they’ll get their chance to grill me too.

This turns the session into a collaboration rather than a one-sided sales pitch.

I don’t beat around the bush—I make it clear from the get-go that the goal is help my prospect to decide today, no matter which way it swings.

Then, I dive into the questions. But here’s the twist: I always start with a bit of context. For instance, I might say, “It seems like you handle X, can you share a bit about Y?” It’s less intrusive and sets a conversational tone, steering clear of the interrogation vibe.

Once I’ve run through my trusty framework and sequence, it’s time to anticipate objections. But that’s a tale for another day.

This has been a game-changer for me, transforming me from a sales newbie to a confident salesperson who can sell without any guidance.

Nothing I’ve shared above is totally new, and I have mixed and matched different philosophies to create a sales process that works for me. I hope this sharing brings value to my fellow sales hustlers out there!

Godfrey – Exabloom Cofounder