³ And I would argue that the web (and specifically, the web browser) is what really did Windows in, breaking a lock-in t

And that’s why I have and will continue to bet on this space. Slack’s amazing outcome aside, this world continues to evolve rapidly, and at some point that evolution is going to be at such a time where the Microsoft sales force (lowercase) effect is muted. Not by something obvious. Not by one big competitor, but by the world changing around them. Just as it did with Windows. Apple didn’t beat Windows with the Mac, they beat it because the world was primed and ready for the iPhone.³ The “Think Different” ads were correct, but the subject was wrong.

If Duolingo’s guilt appeals are, at best, a marginally effective way to keep people engaged or make them feel bad and aren’t even for a good cause, the company should look for more positive ways to get users to stay in the game. Guilt and shame over a sad, fake, multilingual owl who isn’t even a good teacher isn’t worth it.

This all reads as if Slack is over with this deal. Certainly it’s true that for many such deals, the acquired company and product is never the same. And while the acquiring company always says the right things at the offset (would they ever not?), the proof will be in the product. But every once in a while, the best such deals not only don’t kill a company, but act as a major accelerant. This Salesforce deal feels like that for Slack for all the reasons listed above. It equips Slack to better fight the battle on the field right now. In the sales field. And frees up immense resources to get back to the core focus: the product.

Some may read the news about Slack’s acquisition and think: Microsoft does it again! But I think a different cohort will read it differently. They’ll see Slack for what it is: the fastest growing enterprise software company in history thanks to a behavior change which created a literal groundswell within organizations. The proliferation of devices enabled the “consumerization of IT” and Slack more than any enterprise company before it, drove that. They drove it all the way to becoming a $20B public company. And to an eventual $28B sale. This has already kick-started a new generation of entrepreneurs to aspire to such heights in the same general fields. We see it every day with new product-focused enterprise software companies launching left and right. Slack is in their decks because Slack is the example, the guiding light that has led the way. This movement is as unstoppable as Microsoft appears right now. The next step is to break the sales advantage and the bundle. And the millions of pieces of paper are making their incisions…

However, some people do respond well to guilt. Becky Erbelding, a historian in Washington, D.C., says she’s on a 247-day German Duolingo streak — though she rarely opens the emails. The reminder to stay on task in their subject lines is enough for her. “Just ‘keep your ____ streak going’ is enough for me. As if there’s someone out there that would be disappointed if I didn’t do it,” she says. “But I also often try to test out of different levels and then immediately close the window if I know that I lost so that I don’t hear the disappointed music.”

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s with a minimum of an Intel Core i5 CPU, 8 GB of RAM, and integrated graphics can handle web sites, work, and productivity tasks (but not high-end gaming and pro-level work). Or look for an entry-level tablet (iPad, Samsung Galaxy Tab, a 10-inch Amazon Fire) with a keyboard accessory

The frequency of these emails and notifications can also be a turnoff. The 2014 review found that repeated attempts to induce guilt are likely to piss people off to the point where they become resistant to the message. Consumers can become angry with the product, form negative associations with it, rationalize their behavior, and in the end disregard the marketing message. This is partly what happened to me: Duolingo’s subtle escalation, culminating with the message that “these reminders don’t seem to be working,” frustrated and insulted me — and made me feel ashamed about my poor Spanish skills.

And that unlocked a world in which experience could matter. And so you’ll forgive me when I read the takes that Slack was some sort of failure —aside: we should all aspire to fail to the tune of $28B — because they read like the takes that Apple or the Mac was a failure back in the day. The foil here is even the same!

It is still largely true that the best user experience often dies in the hands of the enterprise buyer, but it’s less true than it used to be. And it will get less true still. This isn’t something that changes overnight, this is death by a million papercuts. It’s death by a million millennials.² It’s happening. It has been happening. It will continue to happen.

A 2014 review of the existing research on guilt appeal found that successful guilt appeals stress an element of threat present if someone doesn’t act in a specific way and frame the individual as responsible for someone else’s misery — but, again, the threat needs to feel credible and trustworthy to the consumer. So, for example, Duolingo insisting that I’m making the Duo owl sad is the company’s attempt to create a stress threat. By not engaging with the app, I’m hurting Duo’s feelings. But that turns me off, because the owl is not real and does not actually have hurt feelings as it goes on to learn Spanish without me.

“Shame implies both that there’s little hope for betterment and also that change would be externally motivated, to placate others,” says Linda Hagen, an assistant professor of marketing at the University of Southern California Marshall School of Business. “For that reason, shaming people is often associated with undesired behavioral outcomes, such as reacting defensively [or] withdrawing.”

Still, is it worth potentially making customers feel bad to compel them to open an email or make them slightly more likely to take a lesson? Considering Duolingo’s middling track record for actually helping anyone learn a new language—experts say it’s better as a supplement to existing language courses, rather like homework—it seems unfair, punitive, and absurd to make people feel bad about not keeping up with their language game. It’s not a college class or a charity — it’s a game.

¹ I led GV’s investment in Slack back in 2014 and was a board observer until the company went public via a direct listing 18 months ago. That said, I have had absolutely no inside knowledge about the company since that point. I have remained a shareholder and user, but that’s it, that’s the current bias.

Duolingo is not the only app that does this. Animal Crossing, for example, has its cute animal characters say rude, passive-aggressive things to people who haven’t engaged with it for a while.

You really need to zoom (lowercase) out to see a bigger picture of what is actually happening here. The timing may not have been right for Slack to go head-to-head with Microsoft, but this is the early part of a very long game. Which is why Salesforce’s bet is so savvy here — would be my bet.