Learning Sales Fundamental as a Jr. Account Executive: The 3 Sales Whys

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In 2023, I learned about managing deals and closing new business.

It included learning about the methodology fundamental to a sales process (e.g., Buyer-Led Exit Criteria and MEDDICC).

As a Jr. Account Executive, I handled many inbound discovery calls with buyers at early-stage companies who fit our lowest-tiered monthly plan.

Typically, we wanted these companies to self-serve, but I initially hosted calls to help improve my discovery skills. Now and then, a growth or enterprise deal slipped through the cracks, too. I’d qualify and pass these opportunities to Senior AEs.

A few conversations I had eventually matured into piped opportunities months later.

In 2023, I held nearly 70 disco calls.

It sometimes felt like I was drinking out of a fire hose trying to apply my sales training in real time. Too many acronyms to keep track of!

In a weekly training sync, my VP of Sales simplified it:

“The Three Sales Why’s help you focus on the things that matter when engaging prospective customers.”

The three sales whys are:

1. Why should you have to buy this type of solution?
2. Why should you buy from our company?
3. Why should you buy now?

At the beginning of my VP’s tenure, she even kicked off every pipeline review by having reps answer the 3 Sales Whys for each deal!

Today, I’ll review the 3 Sales Whys, reflect on their importance, and explain how to ask buyers the questions tactfully.

P.S. I’ll sprinkle “💡 Pro Tips” throughout the newsletter. They’ll be specific tactics or concepts I’ve observed in watching my Sr. Strategic Account Executive’s closed / won deal call recordings.

Here is an example to kick us off:

💡 Pro Tip: My Account Executive always emphasizes to buyers at the beginning of every discovery call that the meeting is meant to be as helpful for them as possible, going as far as to say it 2–3x!

“Why do they have to buy this type of solution?”

Your goal with this question, regardless of whether it’s a cold or a warm inbound lead, is to:

Identify a pain and anchor it to a quantifiable metric.

Author and Sales Leader John McMahon calls it finding the “pain above the noise.”

Chris Orlob, CEO at pclub.io, explains why we do this:

1. It helps you build a business case
2. It helps buyers appreciate the magnitude of the issue

For identifying pain, you can do this during your discovery call when assessing the relevant challenges in a buyer’s current state.

Of course, it’s simpler to quantify pain with inbound buyers who book a meeting on your website. Generally speaking, they’re aware of the pain and did their research before reaching out.

With cold leads, on the other hand, as sellers, we must help buyers realize the pain they may not have considered and connect the dots.

I’m learning that cold leads require more proactiveness in understanding a buyer’s current state, identifying gaps, and educating them on the pains your solution solves through storytelling.

For example, you can begin a discovery call by letting buyers know about the problems you commonly solve, see if anything resonates, and explore their current state. You can also ask how the buyer’s organization is currently doing things and how it’s going, then transition into what pains your solution solves.

In the end, you can now quantify pain by asking these simple questions I borrowed from Chris Orlob.

What metric is suffering the most because of this challenge? OR What metric would improve the most by solving this challenge?

💡 Pro Tip: My AE is great at finding pain because he is an incredible listener. You can demonstrate active listening by recapping what you’ve heard.

“Why should they buy from us?”

Regarding the order of operations, once you establish a quantifiable pain, it makes sense to figure out the answer to the above.

You’re trying to understand why your solution is uniquely positioned and the best fit to help their company solve its pain. It can include a hybrid of buyer introspection and seller expertise.

For sellers, you can ask questions to get buyers to articulate their needs. Then, you can present your solution’s differentiation compared to what they’ve already considered or haven’t yet considered.

Here’s a list of questions you can ask a buyer:

• Why can’t you just do ____ without us?
• Why not just do things the same way? Why do anything? What has happened in the past?
• How critical is it to achieve ____?
• What happens if ____ goes so-so or badly? What does it mean for the business if it goes well? Who is concerned about that?

You’re actively challenging the status quo and getting them to articulate and justify a purchase.

Here’s a framework by Outreach’s CEO, Manny Medina, to help you present your differentiation:

1. Start with your Why (company’s mission)
2. Give specific examples of how your Why is evident in your solution (investments in functionality, features, etc.)
3. Talk about the types of customers who choose your solution
4. Close with your difference (common reasons why your solution is NOT a fit and explain the company’s stance)

The above can help connect the dots for your buyer and explain why your solution perfectly aligns with their desired quantifiable outcomes.

P.S. Manny wrote an awesome post explaining it in more detail here. I highly recommend giving it a read!

💡 Pro Tip: From what I’ve observed, my AE approaches this differently. He doesn’t sugarcoat our differences. He confidently explains the shortcomings of other providers based on what he’s heard from customers but avoids saying things like “We’re better” or “Here’s why we’re better.”

“Why do they have to buy anything now?”

With this why, you are trying to uncover a timeline and build urgency.

In our buying process, I’ve seen our AEs anchor a timeline to a feature / product launch, seasonality (where a buyer needs our product for peak seasonal usage), etc.

A few questions you can ask:

• When do you want to implement __? How did it become a priority to make it happen in time for this launch? Who else is involved in the decision to start looking at solutions for platforms?

It’s worth noting that understanding a company’s process for buying software is arguably more important than your sales process. I’m saying that because many sellers try to force a square peg into a round hole.

Buyers will operate on the timeline required to execute the steps in their buying process.

The steps in your sales process should be treated as bumpers rather than hard and fast rules. Having this attitude makes for a truly buyer-centric experience. But if the buyer doesn’t have an extensive history of purchasing software, you become more prescriptive in explaining how the sales process typically works and recommend next steps.

💡Pro Tip: My selling process is to help you get through your buying process.

Conclusion

Memorizing 101 frameworks and 10-lettered acronyms can be difficult.

In my experience, the “3 Sales Whys” helped simplify things.

To recap:

“Why do they have to buy?” Identify a pain and anchor it to a quantifiable metric.

“Why do they have to buy from us?” Challenge the buyer in getting them to articulate and justify their evaluation; explain your product’s unique positioning.

“Why do they have to buy anything now?” Anchor the evaluation to a timeline based on internal urgency.

Until next time 🥋