What are “the five whys” and why do you need them for selling?

We’re going to walk through a very systematic approach here called “The Five Whys,” which has been tweaked and redone in a few different contexts over the years. The basic idea is that there are five steps of a buyer journey that are triggers for your B2B outbound sales actions — we’re previously talked about a five-step “wild ride down the funnel” — and each one is driven by a specific “why.”

Yes, there are more steps in the buyer process, or less, when you see it from marketing perspective – but again, those 5 steps are major and they should trigger your appropriate outbound actions.

Take a look (we’ll get more detailed in a second):

five whys B2B sales 1
The five whys are obviously in the far left column. For each stage, you see where the prospect is beforehand — before that “why” question is addressed — and where they need to be afterwards.

The ultimate journey is from “I’m so crazy busy, I have absolutely no time to talk to you” (what salesperson likes hearing that?) to “I am committed to you, and to now.” That’s a massive jump, but if you can do it right, it’s the essence of sales.

Pro tip:

You might be able to leapfrog a single step, but definitely not two or three. This is the failure most sales people do: trying to lift-up the buyer from “why listen” directly to “why you” (e.g. by sending a commercial proposal right after a good first phone call – that does NOT work, dude!)

So how do the steps work and what can you do about it?

The big thing to understand first

Notice just how distinct the first two whys (Listen and Care) are from the last three (Change, You, and Now).

The final three whys (Change, You, and Now) are about gaining commitment — and closing a sale. These are typically the domain of account executives. But take another look at the first two whys (Listen and Care); these two are about opening doors and sparking interest. It’s about making the buyer a) aware of the relevance of his problem and b) willing to do something about it.

Regardless of what you’re shooting for—an introductory meeting, technology demo, or fully-qualified opportunity—your reps’ first hurdle is to arouse curiosity and get prospects to listen.

The essence of your sales development strategy is deciding how far down these “five whys” your reps can and should take prospects. If you’re an established company then you can certainly consider having SDRs handle the first two whys (if done correctly).

But, if you are a startup and/or your sales organization desperately needs at-bats, you may just want to focus on why listen. Where to draw the line is a decision that you’ll have to make and likely revisit as your team grows.

Mapping the five whys to stages you might be more familiar with:

five whys B2B sales 2

That’s the same chart as above, but the final column (far right) now maps it to how some people come up understanding the sales process/funnel.

Now let’s go one-by-one.


How Software And Services Companies Double The Number Of Mid-Market Customers In 180 Days.

Why listen?

The goal here is “I’m so slammed” to “OK, I’m curious.”

You accomplish that with:

  • Raise curiosity with a well-written cold email
  • Ask them questions about their pain points
  • Do some research on their numbers and what they seem to be investing in; come prepared with that
  • Get a former colleague or internal champion to start working their ear
  • Have a few one-sheets prepared with current customer results
  • Have a quick answer on the cost model

The core question of this stage is really:

  • Based on where you are maturity-wise, is this handled by a SDR/BDR or a more experienced principal?

Why care?

The goal here is “curious” to “interested.” To get someone to interested / discovery call, you will need:

  • Assets on the effectiveness of the solution
  • How similar companies have used it to solve pain points
  • Webinars
  • Customer feedback
  • Marketing collateral
  • The ability to bullshit with them about what they’re actually trying to do in their business

The same question remains at this level: SDR/BDR for bigger companies, usually, and established sales reps for smaller or growth-minded younger companies. You could also institute a training context in any size organization where the SDR works the relationship-building and receives guidance/pointers from a more experienced sales professional. That could kill two birds with one stone.

Why change?

To move from “interested” to “active” and create a pipeline opportunity, you need to destroy the status quo. That’s the whole deal. In reality, even though there might be some nuance here, at this stage the situation is mostly set up like this:

  • Situation A: The customer is interested but ultimately does nothing, so basically stays with their current option
  • Situation B: The customer moves in the direction of buying from you

You need to enable the change. You facilitate the change. You destroy the status quo. The prospect absolutely has to believe that Situation A (current deal) is hurting them, and Situation B (you) is essential. When you enable that change, you sell — and you sell a lot. Everyone has different approaches to enabling this change, but here’s the most important thing.

As was also discussed in The Challenger Customer, most sales guys try this route:

  • Discuss how great Situation B is
  • Extol the virtues of Situation B
  • Show the ROI of Situation B
  • Explain how Situation B is absolutely the greatest thing in human history

But because of those issues above, sometimes Situation B is looking amazing — often too amazing — and the prospect still does nothing. The change seems too radical. They stay with their current solution.

Research has consistently shown that the more effective approach is actually to destroy Situation A. A concept like fear of missing out (FOMO) is huge; it drives a lot of why social media is popular, for example. (And why social media depresses people.) The prospect has to believe that their current state (Situation A) just isn’t getting it done, and they’re totally 100 percent missing out by not using Situation B. You have to destroy any remnants of Situation A being appealing to them. That’s where you sell. You have to “lead to B” and not “lead with B.”

This is why you see SDR/BDR fade out more at this stage and more experienced professionals come in — this is where you move from “building out the relationship and the knowledge base of what they need” to “working the close.”

One of the bigger takeaways of this stage is “Stop selling how great your features are” and “Start selling how essential what you have is.”

Why you?

This is where the prospect moves from active discovery to “OK, you’re the guy/company/solution.” That’s a big step. Simply put, though, you hit it with:

  • Continuing to develop the relationship
  • Continuing to listen to them
  • Showing them what you’ve done for other customers
  • Demos
  • Demos with their data
  • Letting them talk to technical experts
  • Giving them access to the top
  • Showing them their levels of technical/account support if they come on board
  • Etc.

But now they’re just committed to you — they might be on another contract or have some other timing issue that’s going to push it all back. So now you need the final left-right hook combo.

Why now?

“Committed to you” becomes “committed to now.”

This stage is deceptively easier than people think — you’ve already got the commitment, and that’s the hardest part. So much of work is about urgency, especially because many companies do operate on a quarterly model or are in growth mode and need to see immediate returns. Because urgency is often crucial to work, sell the urgency. You can’t wait. You need to get out of that other deal and move to ours. It’s going to be huge for your next four quarters. You’re going to save this much. Whatever the specific angle is, the underlying approach is urgency or scarcity. Push the urgency and move the commitment from “Yes, we’re going with you” to “We’re going with you now.” It varies by who the prospect is/was in terms of specific approach, but all you’re doing here is putting the final urgency stamp on the deal proces.

Don’t go out of order!

This is the order:

five whys B2B sales 3

If you try to start with “Why Change?” — many salespeople lead with this — you haven’t established why the prospect should take time to listen to you or care about what you’re saying, and that sales approach is probably going to flop. As noted above, the first two steps are about relationship-building and setting up the value of your offer. The final three steps are about closing and delivering. You need to move through this in a logical progression; if you try to jump around or jump too far into the process looking for a quicker sale, it will blow up on you.

Learn more about converting leads into real customers, and try to understand the modern B2B sales essentials.

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