20 Years in Sales: What I Would Tell Someone Starting Out Today
Twenty years in sales teaches you one thing above everything else: sales is a skill set, not a personality trait. Full stop.
You are not a born salesperson. Nobody is.
B2B sales, sales leadership and business development can be coached, developed and improved through structure, process, practice and honest feedback.
Not talent. Not charisma and certainly not the "hustle harder" clichés that ignore skill, structure and support.
I have built sales pipelines from nothing. I've missed quota and figured out why. I've coached sales reps who genuinely believed they were not "salespeople" into becoming some of the best performers on their teams.
Twenty years on the frontline has taught me a lot about sales performance, prospecting, pipeline management, qualification, discovery, negotiation and sales coaching.
Here is what two decades in B2B sales has taught me.
Build Your Sales Pipeline Before You Need It
An empty pipeline is one of the biggest causes of missed quota. Prospect every day, even when things are going well. Especially when things are going well.
A healthy sales pipeline gives you options. An empty one creates pressure, and pressure changes how you sell.
Know Your ICP Before You Build a Call List
Know your Ideal Customer Profile (ICP) before you start prospecting.
Vague targeting is just being a busy fool.
If you don't know who you're trying to reach, why they should care, what problem you solve and why they would buy from you, you're going to waste a lot of time talking to people who were never going to become customers.
Cold Calling Still Works
Cold calling still works.
The sales reps who learn how to do it properly can build pipeline faster than those who avoid it. Stop avoiding it. Get calling. It is a skill. Learn it, practise it and get better at it.
Personalisation Beats Volume
One personalised message to twenty relevant prospects beats a generic blast to two hundred. Every time. Good sales prospecting isn't about sending the most messages. It is about getting the right message in front of the right person at the right time.
Speed Wins on Inbound Leads
When an inbound enquiry comes in, respond quickly. Within an hour where possible. Most competitors won't.
Some won't even respond on the same day. Speed is a competitive advantage in sales, and it costs very little to execute.
Qualify Hard or Pay for It Later
Unqualified opportunities are not opportunities. They are distractions. Adding endless follow-ups to poor-quality opportunities kills focus, time and sales productivity.
If you're struggling to close deals, don't automatically look at your closing technique.
Fix your qualification and discovery first.
Discovery Is the Most Underinvested Part of the Sales Process
Too many salespeople spend their time preparing what they're going to say rather than thinking about what they need to learn. Less pitching. Better questions and better questions throughout the entire sales conversation.
After you ask a good question, stop talking.
Silence is where the real insight lives.
Let your prospect think. Let them explain the problem in their own words. The better your discovery, the better your qualification, proposal and eventual close are likely to be.
Manage Objections Like a Professional
An objection is not a rejection. A prospect who pushes back is engaged. The ones nodding along to everything are not necessarily buying.
An objection usually means the prospect hasn't seen enough value yet, doesn't have enough information, or has another concern that hasn't been uncovered.
Your job isn't to argue.
Your job is to understand what is behind the objection and deal with it professionally.
Never Discount Without Getting Something in Return
If you're going to discount, get something in return. A faster close. A longer contract. A larger commitment.
Something.
Discounting simply because a prospect asks is not negotiation. It's giving margin away.
Remove Dead Deals
A stalled deal taking up mental bandwidth costs more than removing it. Be honest with yourself.
If an opportunity has no genuine next step, no compelling reason to buy and no commitment from the prospect, stop pretending it's going to close.
Remove dead deals.
Get your time and focus back.
Get Better on Purpose Every Week
Sales improvement doesn't happen by accident.
You need to work on it.
Use Your Manager Properly
Your manager is one of the most underused resources available to you.
Don't ask:
"How am I doing?"
Ask for specific feedback.
Ask:
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Where am I losing opportunities?
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What could I have done differently in that meeting?
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Where am I weak in discovery?
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How could I improve my qualification?
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What would you change about that call?
Specific questions produce useful answers.
Feedback Is Fuel
The salespeople who actively chase honest feedback improve faster than the people who avoid it.
Feedback isn't criticism. It is information.
Use it.
Track Leading Sales Indicators
Quota tells you what already happened.
Your sales metrics and leading indicators tell you what is likely to happen next.
Track things such as:
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Prospecting activity
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Response rates
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Reply rates
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Meetings booked
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Meeting conversion
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Qualified opportunities
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Pipeline creation
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Conversion rates
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Win rates
Get to know the metrics that help you hit and overachieve quota.
Run a GROW Review Every Friday
Fifteen minutes.
That's it.
Goal. Reality. Options. Will.
Use the GROW model every Friday to review the week.
What was the goal?
What actually happened?
What options do you have?
What are you going to do next?
Do it before the week is over.
Then do it again next week.
And the week after that.
Do this consistently and you'll start to notice the improvement.
Consistency Beats Short-Term Motivation
Show up consistently and let it build over time. This applies to prospecting. It applies to follow-up.
It applies to learning And it applies to building your personal brand.
Use LinkedIn as a Long-Term Sales Channel
LinkedIn can be one of your most powerful long-term channels for B2B sales and business development.
Post consistently. Engage genuinely. Share what you're learning. Share what you're seeing in the market. Share useful sales and leadership insights and never pitch someone simply because they accepted your connection request.
Build the relationship first.
Process Over Personality
This is one of the statements I will live and die by:
Process over personality.
The sellers who last aren't necessarily the funniest people in the room. They're not always the most charismatic.
They're the most structured.
They know what they need to do. They know their numbers. They follow their process. They ask better questions.
They review their performance. They take feedback and they keep improving.
Sales excellence is not something you're born with.
It is a skill set that can be coached, practised and developed.
Small Improvements Compound Fast
Small improvements can make a huge difference.
A 5% improvement in qualification, outreach and win rate simultaneously doesn't simply add up.
It multiplies.
Read that again.
That's the whole game, really. There isn't one silver bullet.
There is a skill set made up of small, sometimes boring, repeatable habits that compound faster than any shortcut ever will.
Better prospecting. Better qualification. Better discovery. Better follow-up. Better pipeline management. Better feedback. Better planning. Better execution.
Do those things consistently and the results follow.
Twenty Years in Sales and I Believe This More Than Ever
Strong leadership, clear processes and empowered people drive sustainable growth.
I believed that when I started. Twenty years in, I believe it more than ever. The best sales organisations don't rely on a handful of "lone-wolf superstars".
They build people. They create clear processes. They coach their teams. They measure what matters and they create an environment where good people can become better.
That's what sales coaching and sales leadership should be about.
Not generic motivation. Not "hustle harder". Not another script.
Real skills. Clear structure. Honest feedback. Consistent execution.
If you're serious about improving sales performance, developing your sales team or becoming a better sales leader, that's the work that matters.
If any of this resonates, follow me for more sales leadership, B2B sales and coaching insights across every platform:
To the next 20 years.
Thanks for reading.
Darren