How to Know if You’re “Bad at Sales”

Have you read all the books, taken multiple trainings from gurus/experts and still find you’re converting less than 50% of your leads?

It’s because all the books and expert training were created by someone with a different personality, product/service and audience than you.

And because a lot of it was designed with extroverts in mind – not introverts.

Want to hear something that might sound astounding since it’s so different from sales advice today?

If you stick 100% to ONE sales strategy you will sell less than if you used a combination of many strategies/styles that feel good to you.

  • For example, I never read a book about sales until last year and I’ve consistently had 5 out of 10 people saying “yes” to working with me throughout my career.
  • Instead of books, podcasts, courses, or even roleplaying – I learned selling as a digital advertising rep going on calls with other print sales reps (they call it 4 legged sales calls).
  • It’s always strange when I hear in this online space there’s only one style of sales strategy that works…because the first half of my career was pretty much a buffet of sales styles.
  • It allowed me to see what worked for other people and adopt what I liked/felt like it fit my personality.
  • And, most importantly, NOT include things that didn’t feel like they fit me (without judgment. If they work for someone else they should keep doing that!)

It’s just not necessarily what jives with my personality. So, the delivery wouldn’t feel right.

For example, one of the people I went on calls with was very buzz word heavy – on purpose.

He used to say “I want it to be 20% greek, 80% layman’s terms. So, they know that I know more than them and as a result, they need me.”

The result? People would always call him a “genius” and say things like “this guy knows his stuff”, etc. and buy from him.

However, that does NOT fit my personality and as a result, would come off condescending and confusing when I implemented it.

So, I didn’t adopt this strategy.

  • Another guy I went out with all the time was a master at keeping it concise and result based.
  • His clients were car dealers – and if you’ve ever worked with car dealers it’s a LONG game.
  • They’re busy, everyone is trying to sell them something and they’ve got short patience for it.
  • So, everything this sales guy brought to them always had value in it for THEM.
  • It might not even have to do with something we were selling – it could be a game they had talked about, a book, a movie, etc.

The point was, it was rarely about us and it was always BRIEF and high impact.

The result? Eventually the car dealers would be asking HIM for what he was offering, how he could help them, etc. because he’d established he wasn’t just in it for him. He listened and cared and as a result, they felt like they could trust him.

I loved this approach and use it to this day, especially for effectively following up (a strategy I’ll lay out in another post).

A final example comes from my time managing sales teams.

  • There was a guy on the team who had a very authoritative tone that essentially communicated “you’re a dumbass if you don’t do this” type of approach.
  • It worked extremely well for him – his close rate was very high.
  • But this would NOT work for everyone.
  • And when others on the team tried it their close rates plummeted because it felt rude, fake or phony.

Because in my experience, the fastest way to winning sales is something that is custom fit to YOU.

Sure, you can try forcing something to work for you and with sheer will and repetition – it could start working for you too – eventually.

That’s what most sales experts say to do. Endure hundreds of rejections with an ill fitted strategy before you can be “good at sales.”

But that is the most uncomfortable and slowest way to become “good at sales” – and a lot of people end up quitting before they finally see results.

They quit convinced they’re “bad at sales” when they just had a bad sales strategy for them.

So, what’s the fastest way to create a custom sales strategy that converts (besides one-on-one custom coaching)?

It’s simple.

If something in your strategy feels weird when you deliver it – don’t do it. I promise if you feel weird, your prospect feels weird too.

Your measuring stick should be – if it feels good delivering it – do it.

Your confidence and comfort will naturally create a tone and delivery that establishes more trust and connection.

It’s like, have you ever heard a really funny joke/story? And so you try to tell it and no one laughs.

It’s because your delivery, personality and audience is different.

Not everyone can tell the same jokes and get the same laughs.

It doesn’t matter if your cousin, dad, best friend, guru or celebrity insists their sales strategy made them millions.

The only thing that matters at the end of the day is if what you’re doing gets RESULTS for YOU.

So, PLEASE don’t feel shame if you don’t get the same results with a sales strategy as someone else. I promise you don’t need to implement it (and lose sales) a few dozen more times.

(I can’t tell you how many people I talk to who had a strategy that was generating sales, were told it was wrong and to do something else and watched their revenue plummet as they completely lost their way).

If people hear your sales strategy and tell you how wrong it is but you’re making sales – politely tell them to STFU and keep doing your thing.

Results are QUEEN!

And a combination of different sales styles and elements that feel comfortable to you will always convert the most sales.


  • With your input on what feels good and my experience, we’ll create a custom sales strategy for you that will predictably 2x-10x the number of people saying “yes” to your offer (the bigger your lead source – the bigger your ROI).
  • The strategy we create won’t force you to do anything uncomfortable or better suited for “extroverted” personalities and will have nothing to do with pain or pitching.
  • We’ll re-position questions to focus on prospects being a fit and positioning you as an authority by pitch weaving (a subtle and elegant way to avoid the dreaded “pitch.”)
  • I’ll even tweak your pre-qualification process and marketing so you’re getting better prospects on your calls in the first place.
  • Everything will be adjusted over 4 months until you walk away with a perfected custom plan for your sales calls that fits your personality, audience and product like a glove and gets 3-8 people out of 10 saying “yes” to working with you. .

If interested in my mentorship, please book a call and we can discuss the details to make sure it’s a fit for you 🙂

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