Uncomfortable Discovery

tough questions get the best answers

Let’s play a quick game of “Why?”

Most of your deals are lost in the first discovery call.

Why?

We’re not willing to ask tough, uncomfortable questions.

Why?

Because we don’t want tough, uncomfortable answers.

Why?

We’ve been trained to close deals by any means necessary and ignore red flags along the way. Our incentives align to getting deals across the line as fast as possible, so that’s what we try to force.

Why?

Because leadership incentives align to pushing reps to get any/all deals across the line “before end of quarter.”

And the result?

66% of sales reps missed their quota in 2022.

Game Over for everyone.

Here’s the good news: we’re moving into a world of ultra-productivity with the rise of AI tools and the conversation around healthier sales incentives is beginning to circulate. Why?

Because executives (especially in SaaS) are starting to look at longevity and profitability opposed to high-dollar valuations.

This means for the first time ever, salespeople can focus on quality over quantity and spend time working the right deals.

That’s right, you can finally breathe a bit.

Here’s the better (but daunting) news: in a world where salespeople are given the space to focus on high-quality deals with a high CLV, you assume more responsibility in skilled discovery.

Your ability to get past symptoms and uncover true cause, personal motivation, and business value will make or break your deal (and your career).

Don’t finish your first discovery call without asking these questions:

  1. What’s telling you that you have a problem? - this question works because it’s not necessarily self-serving. They might not have a problem worth spending on, you helping them realize this builds credibility for a lifetime.

  2. How have you tried to solve this in the past and why didn’t it work? - the answer to this question tells more about their pain and what not to deliver.

  3. Who would feel left out if we moved forward without involving them? - this is a more emotional way to ask “who are the stakeholders/buyers that need to be in on this?”

  4. How does solving this problem rank against other priorities for you? - if it isn’t number 1 or 2 on their list, they’re probably not buying this fiscal year. Understand this quick to determine your level of effort.

  5. What costs will the business take on if you don’t solve this? - the ROI conversation is watered down and old. Buyers don’t believe in ROI valuations because the models are usually bulls**t. Instead, focus on COI (cost of inaction)Reminder: as AI tools begin to help with repetitive tasks, true sales skills (like discovery) will be what sets you apart. You have to be able to have real business conversations.

Heads up: over the next few weeks, I’m switching the brand of the newsletter from “The Daily Sales Rep” to “Why It Works”

Content will remain focused on sales and begin expanding into marketing tactics as well. We’re going to see a complete blend of the sales and marketing functions, so it’s important salespeople begin adopting a marketing mindset.

That’s all for today, we’ll see you next Tuesday!