The Problem Trees: How to Uncover Pain on Any Discovery Call

by Armand Farrokh

March 14, 2025
Discovery

Most sellers are obsessed with the perfect discovery questions. But here's the thing...

You'll never ask a good discovery question if you don't know what problem you're trying to get in the first place.

When you ask questions without knowing what problem you're trying to solve, your calls go in a million random directions and your prospect gets discovery fatigue because they have no idea where the hell you're going with your perfectly crafted questions.

But if you know you gotta turn an operational problem like "spending time in spreadsheets" into an executive problem like "compensation mistakes" -- all you have to do is think of the question that surfaces the next problem.

So today, we're teaching you the problem map that we call a Discovery Tree. You can use this to take prospects from surface level pain to deep business impact.

  • Situation
  • Problem
  • Executive Problem
  • Business Impact

Let's dive in, using an example from my time selling compensation SaaS at Pave.

(PS: This comes straight from our upcoming discovery course, check it out here)

Level 1: The Situation

The Situation is literally... how they do the thing today. At Pave, this sounded like "I'm planning compensation in spreadsheets."

Here's the thing: there's nothing wrong with planning compensation on spreadsheets if that's the easiest, cheapest way to plan a compensation cycle.

Most sellers spend way too much time mapping out every aspect of the situation. Get off of it as quickly as possible and figure out why that situation causes a problem.

Level 2: The Operational Problem

The Operational Problem sounds like something no one would want to do. This is usually the thing your champion complains about, like "I spend too much time in spreadsheets" or "I can't oversee the manager's compensation decisions without toggling to a million tabs to make sure they're being made fairly."

Now be careful: This is usually a problem to the champion, but not to the business. Who cares if the Manager of People Operations is spending 80 hours in compensation spreadsheets if they get paid $100k per year and your software costs $50k?

Operational problems are 5-figure problems, exec problems are 6-figure problems. Win the champion with the operation problem, but then help them understand how this creates a problem for an executive (which is the key to solving their problem).

Level 3: The Executive Problem

The Executive Problem sounds like bad news a VP would deliver to a CEO. This is usually something that impacts a department-level metric, priority, or risk that could be quantified in a business case (which will be the 4th level).

At Pave, spending too much time in spreadsheets usually led to compensation mistakes.

Most sellers are afraid to ask for the executive problems, but this is where the money's made. Push yourself to get at least one executive problem on your discovery calls before jumping into the demo -- otherwise you're stuck in 5-figure operational land.

Level 4: The Business Impact

The Business Impact is the C-Level metric, risk, or initiative that slips because of the executive problem. Compensation mistakes lead to retention issues and massive PR risk. Rep attainment issues lead to missed revenue targets. Overpaying on software spend leads to profitability slips.

To be clear: You do not have to quantify the entire impact on a discovery call, but if you can at least point to the c-level metric impacted... you're golden. If you can get them to realize that time wasted in spreadsheets --> leads to compensation mistakes --> leads to retention issues... then you can start to quantify all this stuff in the business case.

Three Tips for Building Your Own Trees

Now that you know the 4 levels of problems, here are a few things that'll help you build this on your own:

  1. Start with the Operational Problem: Think about what champions usually complain about, or just invert the feature-benefit on your website (ensure fair compensation decisions --> don't let managers make decisions on bias).
  2. Then ask in what Situation that problem exists: Poor visibility into comp decisions was really an issue if they were planning compensation on spreadsheets. But if they had a comp tool in place, this problem wouldn't be relevant.
  3. Then so-what down to Executive Problems and Business Impact: So what if you can't oversee manager comp decisions? Oh... they make biased comp decisions. So what!? Oh... people leave the company and we get sued. That's bad.

From here, build 2-3 trees total (usually one for each product or major competitor). At Pave, we had trees for running compensation reviews vs communicating total rewards. When we're selling Club Pass to sales teams, we have trees for prospecting problems, discovery problems, and deal management problems.

Go create your trees folks, because next week we're breaking down the questions you can use to navigate the trees from top to bottom.

Use this template right here to build your own discovery trees:

Toolkit: Build Your Own Discovery Trees

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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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