Piss people off (but only at the right time)

daniel debow
Helpful.com
Published in
6 min readAug 16, 2017

This is a story about how to iterate your company’s high-level positioning to inspire customers and prospects as your company grows. I also cover how to piss people off to your advantage. Read on.

Before diving into tactics, let’s have another short refresher on Geoff Moore’s masterful depiction of The Big Scary Chasm (from Crossing the Chasm). Geoff’s insight was that different groups of people have different attitudes toward adopting technology, so you should market to them differently. Innovators want something visionary. Early Adopters want a competitive advantage from tech. The Early Majority wants pragmatic business results validated by customers who look like them. If you position the same for all of them, you fail.

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Got it? Alright, let’s move on to the integrated lesson part of the post.

1. Revel in controversy.

If you don’t offend someone with your positioning, you’re doing it wrong.

Many marketers are afraid of offending people. They want every prospect to resonate with their message. This idea brims with childish optimism and it’s unfortunately dead wrong.

Your vision has got to offend someone. If it doesn’t, that’s a deadpan sign that you’re disrupting nothing and nobody. Fortunately, you can embolden your vision with iteration and create a disruptive vision as you learn about your market.

Peter Thiel believes that early-stage companies that win are those that dominate small niches in large markets (Zero to One). Finding a small niche can be difficult, but a signature characteristic of a high-value niche is if people are upset with the status quo. Inspire these folks with your vision. Almost by definition, by doing so you’ll invariably piss off people who are satisfied with the status quo.

Side point: recall the proverb any press is good press. Controversy sells. There’s no need to elaborate.

Here are some examples of the power of pissing people off in action.

Rypple

At Rypple, we blasted traditional annual performance reviews because we believed that frequent, casual, social feedback created more productive and healthier teams. Surprise, surprise, the words upset incumbent HR directors whose primary output at work was a performance review system. They pushed back with op-ed style articles. Visionaries on our side retorted. Then the frenzy started: our next-gen audience got excited about our vision.

This all happened before our product even worked. Once it did work, we turned up the volume. My co-founder, David Stein, stood up in front of 3,000 people at the HR Tech Conference and put up a slide that simply stated: Performance reviews suck.

To some in the audience, this was tantamount to saying that their life’s work was worthless — perhaps even net negative. But this was a moment of truth. While some people muttered their objections, something magical happened. A few HR people started laughing and clapping. We finally called out what the next generation of leaders was thinking — but nobody had spoken to them. Suddenly, they wanted to be part of our vision.

Slack

Slack disrupted the status quo by positioning itself as the email killer in a game-changing 2015 Time article (headline below).

Lawyers, consultants, BigCo’s, and tons of other shops basically depend on email to stay alive, so they weren’t too happy (needless to say, MS Outlook and GMail weren’t either). That’s the point. Slack appealed to the niche of people who hated using email to communicate internally, and promised to make work simpler, more pleasant, and more productive.

Salesforce

In the early days of Salesforce, if Marc Benioff had one chance to say something to a prospect, he’d say “no software”. Think about it: his message was only two words and had nothing to do with sales tools. This might even seem backwards to people today who think of Salesforce as a software company.

But in 1999, people still installed software using CD’s. IT departments considered system-wide software updates to be nothing short of a Herculean task. To sales people at the time, software meant “pain.” It meant not hitting quota because of system hiccups. Marc couldn’t have sung a sweeter song than he did by promising the demise of software.

Of course, his message caused IT people to sound the alarms. They saw themselves as knights protecting the realm from unauthorized programs from the internet. By design, Salesforce was so quick to set up that it went undetected by IT. Sales teams just started using it. It caught fire. And once they were using it, it was so valuable that IT lobbyists couldn’t kick it out.

Drift

David Cancel, CEO of Drift, is shaking up a generation of marketers by envisioning a future with “no forms”. Forms are the number one lead source for most companies, so killing them understandably causes some concern.

But David isn’t anti-leadgen. He believes that companies get more high-quality leads with messaging, not from forms. He’s getting attention with sparky positioning, and it’s working.

2. Okay, you can stop insulting people now.

Controversy works wonders when you’re talking to early adopters in the beginning stages of your product. But when you move along the adoption curve, you need to stop insulting people.

The Early Majority doesn’t react well to being told their systems suck. They only buy products when they have proof that it’s worked for others who look like they do (that’s what makes them the Early Majority). So tell them about that instead.

At this point, it’s time to go back to the positioning drawing board. Craft a story of your company being a bridge to the future. Acknowledge the value of prior tools (read: what your decision-makers made their life’s work), but help them understand that times have changed. Get on their team. Say: “You can take all the great work you did back then, and make it even better. You are not stupid, dumb, or a Luddite; you did the best you could in the past, but now new tools have emerged.”

David Stein taught me this lesson at Rypple. While I tended to be a more aggressive, confrontational communicator, David would say the same points as I would, but would approach it from a higher level and never make people feel bad about what they do.

Perceptive companies know how and when to make this shift. The signals are sometimes hard to pick out from the noise. Iterating on your story doesn’t magically come overnight. You have to talk to a lot of people to get it right. Every once in awhile, you’ll tell a story and someone’s eyes will light up. When that happens, write it down so you can remember what you said. Then start stitching the stories together. You’ll start overcoming objections before your customers can voice them. You’ll start forming in your mind a story, and a vision you know will resonate.

This is a follow-on to my post, Killing it with Vision.

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P.S. Helpful is a new company I’m working on. Check it out here to learn more.

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daniel debow
Helpful.com

Dad of 4, CEO of Helpful.com, ex-Salesforce SVP, founding team at Rypple & Workbrain, angel investor, bass player, adjunct prof @UofTLaw and curious person.