Three ‘Why’ questions you need to answer fast and well

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Doug Kessler

04. 05. 2021 | 5 min read

Three ‘Why’ questions you need to answer fast and well

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In the Holy Trinity of Tech Marketing, we talk about three core questions every B2B company needs to be able to answer well (Who the hell are you? Why should I care? and Why should I believe you?).

Well there are three other questions—three Whys—that are just as important to answer even earlier, as soon as you have the attention of an ideal prospect.

We call them questions but, if you do this marketing thing really well, you can actually preempt the prospect’s need to ask in the first place. So in that sense, they’re three messages you need to be sending out all the time.

Here goes:

Why now?

Marketing asks people to make a change in their lives.

But people hate change.

We even have a word for people who ask us to change our lives: they’re annoying. (A fundamental reason most people hate most marketing. A lot of it tries to make us think about something we’d rather not think about).

Of course, people will change. But they’ll only do it when the cost of not doing it exceeds the cost of doing it. (‘Cost’ meaning things like money, time, disruption, missed opportunities…).

In other words, we’ll change when the world has changed enough to force us to. (We drill down into this in the terribly-titled-but-kinda-clever Irresistible Content For Immovable Prospects).

That means, “Why Now?” is probably the single most important question every B2B marketing team has to have a fantastic answer for. (Which is why it’s the first of the five messages that make up The Galvanizing Story that your B2B brand really, really needs).

Before we can sell our widgets, we need to sell the change in the world that makes our widgets necessary.

This change in the world needs to be real, compelling, and recognised by our prospects.

Ideally, it’s a fresh spin on a set of trends that no one would dispute.

Your “Why now” is your alarm bell for the market. Your “Hey, look! There’s a new dynamic in play. You need to respond to this.”

A great “Why now” is a powerful thing that can open up markets.

A bad one (or none at all) creates a headwind that makes all your marketing have to work much harder.

Why you?

This is where an imperative starts to turn into a relationship.

You’ve sold someone on the change in the world. What they do next is pretty important.

Do they go off to learn more about this new dynamic from someone else, or do they stay here with you and drill down for more?

This isn’t yet the ultimate question, “Why buy from you?”. This one comes before that.

This is, “Why listen to you?”, “Why read your stuff or watch your videos?”, ‘Why take your company seriously as a source of information?”

If you already have a relationship with this prospect and have earned their trust, you’ve got this covered.

If not, you need to send some strong signals that make people think:

  • “These guys are smart”
  • “They get my market and my world”
  • “They seem to be focused on this challenge – they’re experts”
  • “They’re good at explaining things”
  • “They seem honest”
  • “They seem to enjoy what they do.” (See Mojo).

The first Why was all about the world. This one is all about you.

You need to give people the feeling that you’re a good source of information and insight on the opportunity that the change in the world creates.

The feeling.

You don’t yet have to convince them of things. You don’t need to spray your “Value Prop” in their faces.

You just need to send out the Pheromones of Trust. To earn their attention and engagement instead of assuming you’ve already got it.

While this might seem like a high bar (it kind of is) it’s nowhere near as high as the “Buy from me now” bar.

But most B2B marketers treat the Trust moment as if it were the same as the Buy Now moment. Which, of course, pretty severely undermines the Trust moment.

The key to answering “Why you?” at this stage is to walk more than you talk.

Don’t say, “We’re customer-centric!”… just help them now.

Don’t say you’re an expert, share your expertise. (As you demonstrate your expertise, you’ll reveal all, for better or worse: if you’re really not an expert, you’re toast).

Actually be smart and helpful and good at explaining things and, above all, honest. Insanely Honest.

Why not?

This one’s counter-intuitive.

It asks you to become acutely aware of all the reasons an ideal prospect might not buy from you.

Some will be bad reasons. Fears. Misconceptions.
These need addressing in your marketing.

Some will be good reasons. Things they value that you don’t offer.
These that need fixing in your product or explaining in your marketing.

The tendency of most marketing teams is to go all soft-focus on these things. They’re uncomfortable to talk about. Even bringing them up in internal Zoom calls makes you feel like a cynic.

But the best marketers go forensic on their reasons not to buy—they become the world’s leading experts on their own real or apparent downsides.

The goal is to become even better than your nastiest competitors at picking at your own worst attributes (or stubborn myths).

It might seem masochistic, but a lot of marketing teams fail for exactly this reason: they don’t adequately overcome their prospects’ most significant objections, because they didn’t invest in understanding those objections.

To give you a head start, this post, Understand Why People Should Not Buy Your Products, lists twenty possible reasons to diss you. All good fun.

There you go: three questions you need to be able to slam-dunk.

And here’s a fourth and fifth for free:

Can you answer all three right now?

Can everyone in your marketing team?

[Pause for your soul to pause and choose a path at this existential fork in the road].

[Cue existential soul music. I’m thinking Us and Them from Pink Floyd’s Dark Side of the Moon but you’ll no doubt have your own.]

Published in:

  • B2B messaging

  • B2B storytelling

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  1. Doug Kessler


    May 28th, 2021

    What do you mean “No Comments”? That’s good stuff you bastards! (Isn’t it?)

    1. Doug Kessler

      May 28th, 2021

      Dude, you can’t just shame them into engaging. You gotta earn it.

    2. Doug Kessler

      May 28th, 2021

      Oh shut up.

    3. Doug Kessler

      May 28th, 2021

      No YOU shut up.

  2. Guus Pijnenburg

    P 2 Teksten/Taalbeest

    June 16th, 2021

    You are too funny for serious businessfolks like us. Sorry the deal is off. Way of you nutter. Responding personnally to non existing comments. Belittling big causes and VERY important content. Just after you presented them with a drumroll! I get it, it releases the energy and joy one needs to persist and promote. Be that as it may, many a cliënt has’nt got the stomach for it. Which of course is a blessing in the end.

    P.S. I love these nutty comments, plus the stories they comment on

    1. Doug Kessler

      June 23rd, 2021

      Thank you, Guus! Human engagement!

      (We do use marketing as a filter as much as a magnet — alienating folks who would just end up hating us is good business!).

  3. Johnathan Weberg

    Weberg Enterprises, LLC

    August 31st, 2021

    Hey Doug, I’ll engage with you haha! 🙂

    1. Doug Kessler

      September 1st, 2021

      THANK YOU, Jonathan.
      See people? Was that hard?

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