29 Lessons From 29 Years In Sales
If you want to get good at anything, you take a course, get a degree or find a coach.
Sales is the exception. Most people are handed a target, a laptop and a list, then left to work it out on their own. Making it up as you go along is a terrible strategy, and it is the reason so many capable people quit sales in their first two years convinced they were never cut out for it.
I am approaching my 29th year in sales. Twenty-three of those years were spent in corporate London before I left to build my own training business. I have had wonderful years. I have also had years where I sat looking at an empty diary wondering whether I had made a very expensive mistake. I have been ghosted, undercut, ignored and told no more times than I can count.
Here are 29 lessons from those years. Some of them took me a decade to properly understand.
Why most salespeople are badly trained, not bad at sales
Before the practical lessons, here are two things I believe strongly and say often, usually to people who do not want to hear them.
- Most people aren't bad at selling, they're badly trained. I have walked into rooms full of people their own company had written off as underperformers. Nine times out of ten, nobody had ever shown them how to ask a proper question, how to handle a no, or what to do when a prospect goes quiet. Show them, and they change within weeks.
- Most business courses from universities are a waste of money because they do not teach LinkedIn or selling. Even worse, most business professors I have met have never run their own business. You cannot teach somebody how to win work if you have never had to win any yourself.
Sales lessons about mindset and dealing with knockbacks
Sales is a rejection business. What happens in your head between the no and the next call will do more for your numbers than any technique.
- Feel sorry for trolls and haters. Do not let them take your energy. Anyone with the time to tear down a stranger online has a problem that has nothing to do with you.
- Kindness is one of the most underrated qualities in business.
- So is vulnerability. It makes you more human and more relatable. I wrote a book about what my divorce taught me about business and I was nervous about publishing it. It turned out to be the thing people most wanted to talk to me about.
- Take 100% responsibility for everything you do. The market, the leads, the pricing, the competition. None of it is going to shift because you complained about it in the kitchen.
- It is okay to make mistakes. It is not okay to make the same mistake twice.
- Mental health is a serious problem in sales and far too few companies talk about it. Take care of what you feed your body and what you feed your mind.
- Celebrate your own wins, however small. Most salespeople hit target and think about next month before they have finished the sentence. The target resets on the first. Your confidence does not have to.
Sales lessons about learning and getting better at the job
The people who are still standing after twenty years are the ones who kept getting better long after anybody was telling them to.
- Learning to speak in public is an amazing skill and it opens doors you did not know were there. Some of my best clients came from stages where I was speaking for free.
- Standing out and being consistent will beat talent. I have watched naturally gifted salespeople get overtaken by people who simply turned up every day and did the work.
- Surround yourself with people smarter than you and learn from them. If you are the most experienced person in every room you walk into, find better rooms.
- Always be learning. The more you know and act on, the more you grow. I still read constantly, and these days I get as much from books on business, stoicism and copywriting as I do from sales books.
- You will learn ten times faster with a good coach than you will using Google. Google gives you a thousand conflicting opinions and no accountability. A coach tells you what you are getting wrong and then makes you fix it. If that is where you are, have a look at my coaching programmes.
- My favourite quote, and one I use with every potential client: if you do not invest in yourself, why would anybody invest in you?
Sales lessons about how to actually sell
People expect this part to be complicated. It is not. It is just harder to do consistently than it looks on paper.
- Do not think about the money. Focus on helping the client. The money follows, and the client can always tell which one you were thinking about.
- Stop selling. Listen. Ask questions. Listen. Recap. Listen.
- People do not care how much you know until they know how much you care.
- Prospect every day, even if it is only for an hour. The reason people have a terrible Q4 is almost always what they did or did not do back in Q2. Prospecting counts for very little if you drop the ball afterwards, which is why I have written separately about how to follow up effectively in business.
- Never make a phone call or send an email when you are angry. Write the email if it helps. Save it as a draft. Read it again in the morning and you will delete it.
- Virtual selling is here for the long term, so treat a video call with the same preparation you would give a face-to-face meeting. Research the person. Turn your camera on. Do not read from a script.
Sales lessons about LinkedIn
LinkedIn brings me most of my business and has done for years. It also gets used badly by more people than any other tool I can think of.
- If you cannot make LinkedIn work for you, you are missing out on business that is currently going to somebody else. It took me until 2018, after 23 years in corporate sales, to start posting properly. I wish I had started a decade earlier.
- When you connect with somebody on LinkedIn, do not sell straight away. You lose credibility instantly and you rarely get a second chance. I get pitched within thirty seconds of accepting a connection several times a week and I have never once bought anything as a result. There is a better way to do it, and I have set it out in my post on selling on LinkedIn without being spammy.
- Client testimonials are vital. Overdeliver first, then ask for them while the work is still fresh in the client's mind. Most people find the asking part uncomfortable, so I have written a guide on why recommendations matter and how to ask for them.
Sales lessons about the people you work with
Your colleagues, your manager and the culture around you will shape your career as much as your own effort will.
- Do not gossip. It will come back to haunt you, usually at the worst possible moment.
- Do not work with terrible bosses long term. Life is short and there are better places to be.
- At the same time, learn from terrible bosses how not to behave. Some of the most useful lessons of my corporate years came from watching people I was determined never to become.
- Celebrate the success of your colleagues. Sales floors where people quietly hope others fail are miserable places and they never hit their numbers.
- Put your phone on silent two or three times a day. You will get more done in those blocks than in the rest of the day put together.
What I would say to anyone starting out in sales
Do not try to apply all of this at once. Pick one lesson, work on it for a month, then pick another.
If I could go back and hand my 25-year-old self a single piece of advice, it would be lesson 14. I spent years trying to work it out alone because I thought asking for help meant admitting I was not good enough. It cost me money and it cost me time. Getting properly trained is the fastest thing you can do for your career, and it is the thing most people put off the longest.
Twenty-nine years in and I am still learning. That is the part nobody warns you about, and it is also the best part of the job.
