How to Teach The Hardest Skill In Sales: Discovery

by Armand Farrokh

April 4, 2025
Discovery

Discovery is the hardest skill in sales to master… and it’s also the hardest skill to teach.

Give too much structure and your reps ask canned discovery questions out of context, but give too loose of a structure and the calls wander all over the place.

You have to balance both the art and the science when teaching discovery – so today I’m sharing the 3 steps I took when teaching it as a VP of Sales:

  1. Build Your Minimum Viable Discovery Framework
  2. Teach Problems First, Questions Second
  3. Spend 20% Teaching, 80% Coaching

Let’s hit it.

Build Your Minimum Viable Discovery Framework

Teams obsess about asking the perfect discovery question, but the perfectly phrased discovery question doesn’t matter if you don’t know what problem you’re trying to surface.

So I like to teach my reps 4 levels of problemsBEFORE teaching them any questions:

  1. Situation: Literally, how they do the thing today
  2. Operational Problem: What the champion usually complains about
  3. Executive-Level Problem: Bad news a VP delivers to the C-suite
  4. Business Impact: A board-level priority, metric, or risk

Now that they know what problem they’re trying to get, they’re far less likely to ask an awkward canned discovery question out of context.

Teach Problems First, Questions Second

So now you can teach them one question that will help them uncover each problem:

  1. Situation: Ask why they took the call: I’m sure you don’t take every cold call that comes your way, what prompted you to take this one?
  2. Operational Problem: Use Multiple Choice Questions: Typically when someone’s planning compensation on spreadsheets, they’re either frustrated because it takes so much time, or they can’t oversee manager decisions. Which is it for you?
  3. Executive-Level Problem: Use Magic Moment Questions: My guess is you didn’t wake up yesterday and think ‘I can’t oversee those damn managers!!!' When’d you realize this was a problem?
  4. Business Impact: Use Push/Pull Questions: I know, it drove me crazy when I saw managers trying to give someone an increase when they didn’t actually deserve it too. Hey, I wanna make sure this is solving the right problem – you mentioned improving comp-related attrition was a key priority for Q2, is solving manager comp IQ something that’d really move the needle on it, or is there something else we should prioritize?

And lastly, once they have the questions down, give them two listening triggers to give as they take so discovery feels like a conversation, not an interrogation:

  1. Playback / recap whenever the prospect surfaces two or more points
  2. Tell a story whenever you get to the bottom of a tree or a problem

Now you’ve got the basic problems, questions, and listening triggers. Let’s train the team.

Spend 20% Teaching, 80% Coaching

Spend 20% of your time training the team on the BASICS. If you try to stuff it all in their brain upfront, they’re not gonna remember a thing:

That usually looks like 2-3 sessions in sales onboarding:

  1. Overview of the call structure and the bookends (agenda/next steps)
  2. Deep dive on the meat of the call (problem trees, questions, give & take)
  3. Live tape review to reinforce both of the above (I run this weekly with my team anyway, so they’d just join that)

The key is you need to spend 80% of your time reinforcing the framework to actually get this to stick – so do that in these 3 places:

  1. Run a weekly discovery tape review on Fridays over lunch (when people aren’t under the pressure of a Monday)
  2. Run practice roleplays and 1:1s to hone in on one area of a call based on a rep’s needs
  3. Test for problem depth in pipeline reviews – ie: did they only get to operational problems, or bigger exec problems and business impact?

I repeat…

IF THE ONLY TIME THEY SEE THOSE DAMN TREES IS DURING ONBOARDING THEY ARE NOT GONNA USE THE DAMN THING.

Rant over. Go teach your team the hardest skill in sales, folks.

If this helped and you’re trying to teach your team discovery, you might consider:

  1. Having them watch our discovery course during onboarding or to start the month
  2. Running 4 weeks of tape reviews to reinforce it

It launches next week right here 👊

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Armand Farrokh
I’m the Founder of 30 Minutes to President’s Club, a media company behind #1 podcast in sales and the international bestselling book, Cold Calling Sucks (And That’s Why It Works). By background, I was a VP of Sales who grew revenue from $0 to $13M+ ARR in two years at Pave (a $1.6B FinTech unicorn backed by blue chip investors including Y Combinator, Andreessen Horowitz, and Index Ventures.)
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Want more tactics like this? Keep reading:

6 Discovery Tactics That Make or Break Your Deal

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The Secret to Make Your Prospect Sell Themself

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How to Ask Discovery Questions That Won't Make Your Prospect Puke

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