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How to Nail B2B Inbound Selling: Embrace Asking Tough Questions

May 31, '18 / by Beth Carter

How to Nail B2B Inbound Selling: Embrace Asking Tough Questions

If “inbound marketing” was the buzzword of the last decade, “inbound selling” will surely be the winner for the next. It’s the next logical step in the journey to revenue. Whereas inbound marketing focuses on filling the sales pipeline with qualified leads who are ready to buy, inbound selling focuses on the final mile – encouraging leads to convert into paying customers, using the same inbound philosophy of providing exceptional value for the lead, rather than making self-centered sales pitches.

The concept here is easy: Find the right solution that solves a real problem for your lead and helps your lead achieve a real goal.

But how do you know what the right solution is? Or what your lead’s challenges and goals really are? You’ll never know unless you ask the right questions.

This often means asking tough questions. And for many people, asking tough questions can be uncomfortable. But that’s okay. Get comfortable asking them anyway. After all, life begins at the edge of your comfort zone, right?

Understand the Real Need

Clearly, any solution will have to address a business need for the lead’s company. But the right solution will also meet a personal need for the lead directly. What’s at stake personally for your lead?

Few people will give you this information readily. They may not be comfortable sharing what feels like sensitive, private information, or it may be they themselves haven’t thought that far down the road.

However, understanding these REAL goals and motivations is critical if you’re going to develop a comprehensive solution that does everything both the lead and the company need it to do.

It’s not enough to understand what the lead wants (or thinks he wants). You need to know why the lead wants this.

Sometimes, your lead will want the wrong thing. In fact, this happens more often than one might think. But how will you know this if you don’t understand your lead’s real “why”?

3 Levels of Meaning

It turns out there are three levels of meaning behind your lead’s real need:

3 levels of meaning

You need to get to Level 3. The problem is, your lead probably won’t volunteer Level 3 meaning without some careful prompting from you.

The Secret to Asking Tough Questions

Fortunately, I have a secret weapon I can share with you. It’s a technique I learned from an inbound selling bootcamp taught by David Weinhaus, head of partner sales enablement at HubSpot. To get to Level 3 meaning, ask your lead “why” five times.

It’s not easy … but it’s insanely effective.

Honestly, if you can only push yourself to ask “why” one additional time, you’ll still be amazed at the additional depth of insight you gain.

And in inbound selling, the more insight you have, the better solution you can develop – and the more likely you will be to close the deal.


Related Post: The Best Way to Find Customer Pain Points – So You can Solve Them


So, for example, if I were asking a lead five “whys”, the conversation might go like this:

5 whys of asking questions

Do you see what happened there?

  • Level 1 = Generating more leads from their website
  • Level 2 = Growing 10%
  • Level 3 = Expanding into a more profitable market

By continuing to ask “why,” I got to the insight we needed. Whereas I started out having a conversation about improving the lead’s website, I soon learned that what we really needed to talk about was entering a new market. Which is a different thing entirely.

If I hadn’t pushed beyond that first “why”, I’d only ever be equipped to present a half-solution to this lead … and my “half solution” would ultimately fall far short of what our lead truly needs.

In fact, I could take this conversation even further by throwing in a few “what” questions as well:

  • “What does it mean if you hit it big in this new market?”
  • “What happens if your sales continue to stay flat?”

Asking questions like this helps you clarify your own insights, yes. But it also helps your lead understand what the negative consequences will be from not making a change.

This might be a little unpleasant for your lead. But helping your lead understand these negative consequences helps establish urgency. And be forewarned: A lead who has a need but doesn’t feel any urgency won’t be motivated to close your deal quickly.

No Pre-Determined Conclusions

Absolutely, asking hard questions can be uncomfortable. You may feel like you’re being manipulative, or that you’re simply getting too personal – as if you don’t have the right to dig so deep.

The key when asking these questions is to NOT have a pre-determined conclusion in mind. When you go in with a pre-determined conclusion, you’re going into the meeting already believing your services are exactly what your lead needs.

But how can you know this for sure until you know exactly what the lead really needs? And why would you try to shoehorn a lead into a solution that doesn’t provide exactly what he needs?

The answer is you can’t, and you shouldn’t.

Instead, keep an open mind. Look for reasons you shouldn’t pursue this deal. Ask yourself, “Is it possible I need to recommend a different solution?”

Now take it a step further and ask the unthinkable: “Is it possible my company isn’t a good fit for the lead?”

When viewed from this perspective, asking “why” five times isn’t about being nosy. It’s simply showing that you’re curious about your lead’s business and goals and that you truly have your lead’s best interests at heart.

At the end of the day, inbound selling is about finding the right solution for every lead. If you’re not willing to ask the right questions, you’ll never get there. So go ahead – ask the tough questions. Your lead will be glad you did.

Interested in learning more about inbound selling? Contact me!

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Topics: Strategy

Beth Carter
Written by Beth Carter

I love to write and I'm a total grammar freak. I also passionately believe that conversational, approachable and insightful content can help people solve real problems and can make a real difference in the world.