I’ve spent a good part of my career in sales, and if there’s one thing I can tell you, it’s that nobody starts out as a brilliant salesperson.
You learn by doing. You learn by listening, observing, making mistakes, losing deals and occasionally wondering how on earth a conversation went so badly.
You can read every sales book going, attend all the training sessions and memorise every technique in the manual. But there’s a level of understanding that only comes from being out there, speaking to real people and dealing with real situations.
I’ve always believed that sales is one of those professions where experience counts for an enormous amount. Not because you eventually learn how to get every deal over the line, but because you become better at understanding people.
And some of the most important lessons come from getting things wrong.
Here are seven that have stuck with me.
1. Talking more doesn’t mean selling more
When you’re new to sales, there’s a temptation to prove how much you know.
You want to explain the product, talk about the benefits, demonstrate your expertise and make sure the customer understands exactly why they should buy from you.
The problem is that you can end up doing all the talking.
I’ve learned that some of the best salespeople are actually brilliant listeners. They ask questions, pay attention to the answers and take the time to understand what’s really going on.
A customer might tell you they need a particular service, but what they’re actually looking for is reassurance, reliability or a solution to a much bigger problem.
You won’t discover that if you’re too busy delivering your pitch.
The lesson? Ask better questions and listen to the answers. You don’t need to fill every silence.
2. Not every potential customer is your customer
Early in your sales career, losing a deal can feel like a personal failure.
You start questioning what you said, what you could have done differently and whether you should have pushed harder.
But one of the biggest lessons I’ve learned is that not every opportunity is the right opportunity.
Some people aren’t ready to buy. Some don’t have the budget. Some aren’t a good fit for what you’re offering, and others simply want something you can’t deliver.
That’s business.
Trying to win every deal can be exhausting, and it can lead you to spend far too much time chasing people who were never going to become customers.
Good salespeople understand the value of qualification. They know when to invest more time and, just as importantly, when to walk away.
Your time is valuable. Spend it with people who genuinely see the value in what you’re offering.
3. Following up is important, but chasing isn’t
There’s a fine line between being persistent and becoming a nuisance.
I’ve seen plenty of salespeople lose confidence after one unanswered email or telephone call. Equally, I’ve seen people go too far in the other direction, contacting the same prospect repeatedly without adding anything useful to the conversation.
Neither approach is particularly effective.
Following up is part of the job. People are busy, priorities change and sometimes a perfectly good conversation gets buried beneath everything else going on.
But a good follow-up should have a purpose.
Perhaps you’ve got some additional information, an answer to a question or a useful suggestion that helps move the conversation forward.
Don’t just keep asking whether someone has made a decision. Give them a reason to continue talking to you.
And if the answer is no, accept it professionally. The way you handle a lost opportunity can influence whether that person ever considers you again.
4. Confidence comes from preparation, not pretending
There’s a difference between being confident and acting as though you know everything.
Customers can usually tell when someone is bluffing. You don’t need to have an answer to every question, and pretending that you do can quickly damage trust.
I’ve always preferred honesty.
If you don’t know something, say so. Tell the customer you’ll find out and come back to them. Then make sure you do exactly that.
Preparation also makes a huge difference. Understand who you’re speaking to, research their business, know your product and think about the questions they’re likely to ask.
Confidence isn’t about having the loudest voice in the room. It’s about being comfortable enough in your knowledge and experience to have a genuine conversation.
5. The sale doesn’t end when the customer says yes
This is a big one.
It’s easy to become focused on winning the deal. You’ve worked hard, built the relationship and finally secured the business. Brilliant.
But what happens next?
The customer now needs to receive the experience they were promised. If the service doesn’t match the expectations you’ve created, you’ve potentially damaged the relationship before it’s properly begun.
I’ve always believed that relationships are worth more than individual transactions.
A good salesperson doesn’t disappear once the paperwork is signed. They care about what happens afterwards, whether the customer is happy and whether the relationship has the potential to grow.
The best sales opportunities often come from existing relationships, repeat business and recommendations.
Winning the deal is important. Keeping the trust is even more important.
6. Rejection isn’t a reflection of your worth
Sales can be a tough profession because rejection is part of the everyday routine.
You can have a brilliant meeting, feel that everything went well and then receive an email telling you they’ve chosen someone else.
It happens.
The danger is allowing every rejection to affect your confidence. If you take every lost deal personally, sales can become an incredibly difficult environment to work in.
I’ve learned that you need to develop a certain level of resilience.
That doesn’t mean ignoring feedback or pretending every lost opportunity was someone else’s fault. Sometimes you genuinely could have done better, and that’s worth understanding.
But you also need to recognise that there are factors outside your control.
Learn what you can, take the feedback, make adjustments and move on to the next opportunity.
Your last rejection doesn’t determine how successful your next conversation will be.
7. People remember how you made them feel
You can have the best presentation, the most competitive price and an excellent product, but people still buy from people.
Trust matters. Rapport matters. How you treat someone matters.
I’ve always believed that the strongest sales relationships are built on genuine connections rather than clever techniques.
People want to feel understood. They want to know that you’re interested in helping them, not simply hitting your monthly target.
You don’t need to become someone’s best friend, and you certainly don’t need to agree with everything they say. You just need to treat them with respect, be interested in their situation and do what you say you’re going to do.
That might sound simple, but it’s amazing how much difference it makes.
Experience is the best sales training you’ll ever receive
Looking back, I wouldn’t change every mistake I’ve made throughout my career. Some of the most valuable lessons came from situations I’d rather not have repeated.
The lost deals, difficult conversations, awkward meetings and moments where I got things completely wrong all helped shape the way I approach sales today.
And that’s something I’d encourage anyone starting out in sales to remember.
Don’t expect to be brilliant immediately. Don’t be afraid of getting things wrong, and don’t confuse a difficult week with a failed career.
Learn from the people around you. Ask questions. Be curious. Take feedback seriously, and keep putting yourself in situations where you can improve.
Sales isn’t about finding a magic phrase that makes everyone say yes. It’s about understanding people, building trust and creating relationships that stand the test of time.
You won’t win every sale, but if you learn something from every conversation, you’ll become a much better salesperson along the way.
