Deep Dive Questions

Diving deep in discovery to uncover real pain for real impact

Photo by Nacho Bilbao on Unsplash

Hey Hey 👋

This week’s topic resonates deeply. It’s all too pertinent for me.

I’ve managed 4 separate sales teams as a sales leader, and unsurprisingly this is something I’ve seen and experienced first-hand with each one.

What’s that you ask? (good question)

Asking better, more compelling questions that cut through the “fluff” and dive deep into what’s really important, to uncover real impact.

Deals are won in discovery. And if we gloss over that important step - regardless of which stage the deal is in, means we are fighting an uphill battle.

In this week’s edition of Stretch Weekly -

• Will Barron gives us 5 Questions to Uncover the Buyer’s Real Pain

Plus - don’t miss this week’s snippets as we dive deep to uncover more thoughtful questions to uncover real pain and real impact.

THANKS for reading!!

-Grant

And lastly - as always, if you find this newsletter valuable- subscribe or share it with someone who might as well 👊.

---

---

STRETCH SHARES

5 Questions to Uncover the Buyer’s Real Pain

Its been a while since I’ve shared a Selling Made Simple podcast and this one is just too good not to share.

Will Barron says alignment is key in selling, but most of the time prospects only tell you about their “surface-level” pains. But to close a deal successfully, you need to be able to solve the problem that’s causing those pains. Treat the disease, not the symptoms.

His summary is better than anything I could do so here it is in its entirety:

👇

Surface Level Pains

During the first few talks with potential buyers, you’ll only scratch the surface of their pain points. Your prospects don’t have the expertise to really get to the bottom of the issues. And so you’re left with the superficial problems, not the ones that are the real cause of their pains.

Now that’s actually good news for salespeople like us. Because if buyers did have that knowledge, products, or expertise needed to dive deeper into their pains, they could solve them without your help.

So this leaves a gap between a buyer knowing they have a problem and not knowing how to fix it.

And that’s where we come in. We close that gap. But to do that, we need to move past the superficial pain points and get to the heart of a buyer’s problem. And we can do that using five questions in particular.

Now before we get into those questions, there are four main categories that surface-level buyer pains fall into. Let’s look at some examples of what your potential buyers might say for each category.

#1. Financial Pains

Financial pains. You can spot these with statements like…

• “Revenue is up, but profits are down”

• “I don’t have enough visibility of the numbers to make sound financial decisions”

• “We’re only profitable enough to keep the doors open”

#2. People Pains

People pains, shown by statements like…

• “Our team’s morale is low”

• “Our managers don’t drive innovation”

• “Our best employees keep leaving to our competitors”

#3. Productivity Pains

Productivity pains…

• “We keep missing our client deadlines”

• “We have quality issues that are leading to higher refunds”

• “We spend too much time in meetings”

#4. Process Pains

And process pains, which show up with statements like…

• “Our hiring process is a mess“

• “We have no system in place to monitor our sales pipeline”

• “The customer service department is inundated and can’t keep up”

Alright, so now you know the four categories of pain points. And you’ve heard some examples of how they might share them. So let’s now look at some questions we can ask to dig deeper into the buyer’s pain.

We want to dig deeper into the buyer’s pain so that we can align our service to their deepest, most impactful pain points. Because when we align our service to really deep pain, it becomes a “must have” rather than “something to consider next quarter”.

1. “What’s holding you back?”

The first question that we can ask to dig deeper into the pain of our buyers is this:

“What’s the main thing holding your company (or division) back from growing right now?”

This question is great at eliciting a very specific response. One that lands your prospect’s pains into one of the four categories we covered before.

• Financial Pain

• People Pain

• Productivity Pain

• Processing Pain

This question is the starting point to go a level deeper than the more general categories of pain that we’ve already discussed.

And once you’ve done that, you can move on to the next question…

2. “How do you plan to solve this?”

“How do you plan to solve this pain point?”

An uneducated buyer will tell you that they are unsure how to solve their pain point. This is an incredible opportunity for you to educate the buyer on how your service can solve the problem and relieve their pain.

A more educated buyer who is further through the sales process might have a few ideas on how they can solve the pain. But clearly, there’s still something holding them back from taking action.

So the next step is to uncover what that thing is that’s keeping them from solving the problem themselves.

Now on to question number three…

3. “What’s your deadline?”

We uncover lots of information when we ask the buyer the next question:

“What is your deadline to solve this problem?”

If the buyer tells us that there is no deadline, then the problem is not very painful for the buyer. And that means they’re not going to be very motivated to solve it, meaning you’ll have to work harder to earn their business. The takeaway here? Avoid doing business with these individuals. They’re not worth the effort.

Alternatively, if the buyer does have a set deadline to solve this pain point, you now have a very qualified buyer that is worth engaging with further.

Now we need to keep probing and see if there is the budget and authority to solve the pain.

4. “What does your boss think?”

Now question number four is where we uncover the true level of pain the buyer is in. After you’ve gone through the previous steps and questions, it’s time to ask:

“What does your boss think about all this?”

One of the most common obstacles to a smooth selling process is your buyer lacking the budget or the authority needed to make the purchase. Maybe they have to go to their manager to request funding. Or maybe they need to get permission from their boss before pulling the trigger on the deal.

In either case, closing is going to be a pain. You’ll need to spend extra time convincing stakeholders that your product is worth the value. And you’ll risk your messaging being diluted since your contact then has to then convince their higher-up that it’s worth the price.

All bad things.

So if you ask this question and your buyer says “My boss has been on my back about this for weeks now, I really need to get this sorted” you have uncovered that the buyer likely has both the budget and the authority to solve the issue.

And for you, that means an easier sale.

Now that leaves us with one final question to ask the buyer to go beyond the surface-level pain they’ve been describing to you so far.

5. “What’s stopping you?”

The final question we now need to ask the potential buyer is:

“What is stopping you from solving this problem today?”

This is the most important question in this sequence of questions.

So far we’ve been living in the future with questions like, “What is your deadline?” and “What does your boss think?”

Now we need to pull the buyer back to the real world. What’s stopping them from fixing the problem now, TODAY. This will intensify the buyer’s pain, drive urgency, and make it far more likely that they’ll take action on any suggestions you give them to solve it.

Now you’ve got a quality, qualified lead on your hands that’s ready to buy and easy to close.

Full PODCAST here

---

---

STRETCH SNIPPETS

• 😱 Chris Orlob gives us 5 'unsexy' questions most of you are too afraid to ask. The tough ones to help understand the buying process. Also - check out his “Discovery Prompter” which has closed $100M ARR. Awesome asset to arm your sales team with.

• ❓Jake Dunlap instructs us to start asking the right questions. All buyers want to know the answer to these 3 simple questions

  • 1. Why me?

  • 2. Why now?

  • 3. Why you?

• ⏱️ Throwing it back to one of my favorite podcast episodes from Kevin Dorsey and Nick + Armand to get prospects to admit to their problems without asking unnatural, off-putting questions. Killer questioning tactics that still sound human.

---

---

🧠 Mindset

---

Thanks for reading!

My hope is if you find this valuable, consider sharing it with friends (or signing up if you haven’t already).

— Grant 👋

---

About stretch vp: confessions, learnings, and insights from sales leaders in SaaS

Compiled and aggregated from a network of sales leaders in SaaS, Stretch VP showcases learnings, insights, and experiences as well as best practices to overcome common hurdles, obstacles, and setbacks in your quest for excellence as a sales leader in SaaS.

Are you a VP, Director, thought leader, or content producer in the SaaS space? We’d love to have you contribute. Just reply to this email and I’ll be in touch.

Also… check out the blog or follow on Twitter