
8 Tough Sales Lessons I Wish I’d Learned Sooner

Here are the 8 things I wish someone had told me when I first dove into this thrilling, sometimes brutal, sales arena.
1 NO ONE CARES ABOUT YOU OR YOUR PRODUCT
Here’s the cold, hard truth: no one cares about you or your product—at least not initially.
Customers care about themselves, their problems, their work.
So, skip the self-congratulatory monologue about your company’s greatness and focus on what matters to them.
How do you do that? Well the next lesson addresses that
2 ASK GOOD QUESTIONS
Stop selling and start asking.
The more you know about your customer’s pain points, desires, and deepest wishes, the better equipped you are to tailor your solution to hit home.
Think of yourself as a detective uncovering clues to unlock a deal.
Ask the right questions to understand the impacts and consequences of those challenges.
This will help you gauge whether someone’s motivated to solve the problem and invest in your product.
3 ALWAYS BOOK A NEXT STEP
If you’re not booking the next step, you might as well be chasing ghosts in the sales graveyard.
Every successful sales interaction should lead to a clear next move — a meeting, a demo, a proposal, a trial, a contract, etc…
Something that keeps the momentum going. Otherwise, you risk falling into the abyss of forgotten emails and missed opportunities.
If a prospect wont agree to a next step, that’s a sign something has been missed, which brings me onto my next lesson…
4 DISQUALIFY EARLY
Not every lead is worth your time.
It’s okay to walk away if a prospect isn’t the right fit or isn’t motivated enough.
It’s better to focus your energy on new or more promising leads than to waste precious hours chasing dead ends.
To identify good and bad deals, I focus on two areas
- The impact of a customer’s problem
- The root cause of the problem
Small impact of the problem? No motivation to change.
Root cause of the problem not addressed by your solution? You’re not a good fit solution.
Attempt to disqualify using phrases like
“It seems like you’d be alright without this”
or
“It sounds like this is being cause by {X} which isn’t an area our product solves, have you tried looking into {other category}?”
5 ASK ASK ASK!
If you don’t ask for the meeting/next step/sale/referral/renewal – then chances are you wont get one.
It sounds simple, but so many sales are lost because sellers are too timid to pop the big question.
It’s okay to hear “NO” better hear and have the chance to understand what you could do or could’ve done to change the outcome.
If you don’t then chances are you’ll be ghosted with no information as to what you could’ve done better.
Be confident, be direct, and see where it takes you.
6 NEVER GIVE SOMETHING AWAY FOR FREE WITHOUT GETTING SOMETHING OF VALUE IN RETURN
In sales, like in any relationship, it’s all about give and take.
Don’t give away the farm without getting something in return.
Whether it’s pricing information, a demo, or a discount, always ensure you’re getting valuable insights or commitments in exchange.
There’s an equilibrium to strike between giving and taking in every deal, but most sellers take too much or give too much.
7 HAVE A SALES PROCESS
A good sales process is like a GPS for your deals—it keeps you on track and heading in the right direction.
However, not every customer fits neatly into your predefined steps.
Be flexible enough to recognize when you need to deviate, speed up, slow down, or adapt to unique situations.
8 DON’T TRUST YOUR MANAGER TO TRAIN YOU
I’ve had managers who cared about my success and others who were completely checked out.
Don’t wait for your manager to hand you the keys to success.
Take charge of your own learning journey.
Seek out mentors, devour sales books, speed read everything on Revenue Magazine, and binge-watch YouTube tutorials.
Do whatever it takes to sharpen your skills and stay ahead of the game.
So there you have it—eight hard-earned truths that could make all the difference in your sales journey.
Peace, love, sell.