30 Lessons from 30 Years in Sales

I never liked selling when I started. It took me a long time to appreciate how important sales is and what amazing skills you can learn. After all, everybody works in sales.

Thirty years is a long time to get things wrong before you start getting them right. I've made most of the mistakes on this list myself, which is exactly why I remember them. Here's 30 lessons I've learned that will help you make more sales and get better results in the future. Read it start to finish, or jump to the section that speaks to whatever you're wrestling with this week.

Sales mindset lessons from 30 years in sales

Every sales problem I've ever seen traces back to mindset before it traces back to technique. Get this part right and the rest gets a lot easier.

1. Selling starts with the mind. Once you get that right, the other steps are easier.
2. Ignore trolls and haters. Don't let them take away your energy. You'll never please everyone, and trying to will cost you the energy you need for the people who actually matter.
3. Don't gossip, it will come back to haunt you. Sales is a small world. Whatever you say about a colleague or a client has a habit of finding its way back to them.
4. Kindness is one of the most underrated qualities. It costs nothing and it's the thing people remember about you long after they've forgotten your pitch.
5. So is vulnerability. It makes you more human and relatable. The salespeople I trust most are the ones who admit when they don't know something.
6. Mental health is a serious problem. Take care of what you feed your body and mind. Sales is a rejection-heavy job. If you're not looking after your mental health, the job will find the cracks.
7. Take 100% responsibility for everything you do. Not 90%. Not "yes, but the market was tough." All of it.
8. It's okay to make mistakes, it's not okay to make the same mistake twice. Mistakes are how you learn. Repeating them is how you stop learning.
9. Put your phone on silent 2-3 times a day. You will focus and achieve so much more. Try it for a week and notice how much deep work you actually get done.
10. Life is better when you serve others. This applies to your clients and it applies to everyone else in your life.

Business lessons for long-term sales success

Talent gets you started. It's not what keeps you in the room for 30 years.

11. Always be learning - the more you know and take action on, the more you grow.
12. While I still read sales books, I'm currently getting more value from books on business, stoicism and copywriting because these are also valuable for selling. A good sales book teaches you a technique. A good book on stoicism teaches you how to handle the rejection that comes before you get to use it.
13. Learning to speak in public is an amazing skill to have and it opens so many doors. It's also one of the most avoided skills in sales, which means the people who do it well stand out fast.
14. Standing out, consistency and resilience are more important than talent. I've watched plenty of talented salespeople burn out and plenty of average ones build brilliant careers because they simply kept showing up.
15. Don't work with terrible bosses or toxic clients.
16. At the same time, learn from terrible bosses and toxic clients on how not to behave. Some of my clearest lessons in leadership came from working out exactly what I didn't want to become.

Common sales frustrations and how to deal with them

This is the section I could write a whole book on. Two lessons, but they're the two that frustrate me most.

17. Most people aren't bad at selling, they're badly trained. I meet salespeople all the time who've been handed a script and a target and nothing else. Give people the right training and the right support, and most of them turn out to be far better at this than anyone gave them credit for.
18. Most business courses from universities are a waste of money because they don't teach LinkedIn, sales or mindset properly. Even worse, most business professors I've met have never run their own business. You can't teach what you haven't lived. I'd rather learn from someone who's closed the deal, lost the deal, and had to work out why.

Sales relationship lessons that actually build trust

Every deal is a relationship before it's a transaction. Treat it that way and the rest follows.

19. Don't think about the money. Focus on helping the client. The money follows the help. It rarely works the other way round.
20. Surround yourself with people smarter than you and learn from them. Your ego might not thank you for it. Your career will.
21. Celebrate the success of your colleagues. Sales can feel like a competitive sport, but the teams that win long term are the ones who genuinely want each other to do well.

Practical sales tips you can use this week

These are the tips I come back to most often when I'm coaching sales teams, because they're simple to say and genuinely hard to do consistently.

22. If you can't leverage LinkedIn, you're missing out on so much business. It's where most of your buyers already are, researching you before they've said a word.
23. Celebrate your own wins, no matter how big or small. Sales is hard enough without ignoring the good days.
24. Don't make a phone call or send an email when you're angry. You will regret it. Wait an hour. Read it back. Then decide if you still want to send it.
25. Prospect every day. Even if it's just for one hour a day. Consistency beats intensity in prospecting, every time.
26. Stop selling. Listen. Ask questions. Listen. Recap. Listen. If you're talking more than your prospect, you're doing it wrong.
27. Client testimonials are vital. Always overdeliver and ask for them afterward. A great testimonial does more selling for you than any pitch deck.
28. When you connect with someone on LinkedIn, don't sell straight away. You lose credibility and often don't get a second chance. Build the relationship first. The sale can wait a message or two.
29. You will learn ten times faster with a good one-to-one coach than you will using Google. Google gives you information. A coach gives you the context to actually use it.
30. My favourite quote that I use with every potential client: "If you don't invest in yourself, why would anybody invest in you?"

I've uploaded 12 videos to my YouTube channel, Everybody Works In Sales, over 120 videos in total, and I'll be adding plenty more content in the months ahead. To make sure you don't miss out on valuable sales and LinkedIn videos that won't always be seen on LinkedIn, please subscribe to the channel.

You might also find useful:

• If any of the mindset or frustration lessons above struck a nerve, my group sales training programme is built around exactly these problems, with live roleplay rather than slides.
• Lessons 22 and 28 are just the start of what LinkedIn can do for your pipeline. My LinkedIn training for sales teams goes much deeper.
• Ready to talk it through? Get in touch for a no-obligation conversation.