Back in the early days of Rypple, we met a young, energetic Gen Y who worked in the HR department of a large Telco. She got really excited about Rypple and really wanted to introduce it to the whole company. So excited, in fact, that she managed to book us a meeting with the SVP of HR.

We got dressed up in our best suits and made the pilgrimage to their office. Arriving a little early, we were seated in a boardroom and told that our host would be right down. Twenty minutes later — fifteen minutes after we were supposed to start — she waltzed in, sat down at the far end of the table, and crossed her arms. Warning bells started going off in back of my mind.

Without waiting for our story, she spat out:

“I just want you to know that I think software doesn’t change culture.”

Silence for a moment as we absorbed that. I knew where she was coming from: the world of horribly designed Enterprise HR software that we documented in my previous blog post. Damn straight I thought.

“You’re right” I said. “Badly designed software doesn’t do it.”

Thing is — she was right. She’d been burned by other vendors who promised the moon and delivered a lump of Swiss cheese. She lives in a world where all enterprise software, including HR, is data entry. It’s software designed around the belief that if we can just get people to fill in these boxes, we’ll know what’s going on in the company. That kind of thinking shapes the behavior of everyone in the company and their expectations of what business software does.

So, I wish I could say the story ends with us convincing this sceptical cynic. It doesn’t. She listened politely and showed us the door. But, it was an incredibly helpful conversation. It helped us to realize the challenges we were up against, and in particular the challenge of a traditional sales model – top-down, to traditional buyers – for the next generation of business software. It was a classic customer discovery conversation.

At the time, we didn’t know what to respond with. We didn’t know what well designed software in the right context could do. Today, we know differently.

So, if I had this conversation as a do-over, here’s what I’d do. I’d take a different approach. Instead of attacking straight on, I’d ask:

“Do you think Facebook has changed our culture?”

Mark ZuckerbergIt’s hard to say no to that question. Two years ago, when we had this meeting, Facebook was just breaking 100 million users. Now 1 out of every 14 people worldwide has an account and the #1 movie in America is all about their creation myth. People spend over 700 billion minutes per month on the site. They share ideas, pictures, thoughts, ephemera, and even organize for change. Whether we like it or not, Facebook is changing our ideas of privacy, friendship, openness, transparency and community. It’s a culture force for change on an epic, worldwide scale.

And then I’d say: “Facebook is software. Incredibly well designed software. So well designed that it doesn’t require change management, training or pressure.”

I’d ask:

“Do you think the collapse in the newspaper industry is a change in our culture?”

The NewseumCraigslist had a lot to do with the collapse — and this is hardly new news. John Podhorertz wrote a great piece for Commentary back in May 2008 called The News Mauseoleum, all about the opening of The Newseum in Washington, the news industry’s $475 million paean to their own glory, squeaked out on Nero’s fiddle while Rome burns around them. Here’s what he had to say about Craigslist:

The rise of the Craigslist model has devastated classified advertising in newspapers, once the only place in a city to sell a used car or list a job opening. True, today’s newspapers have duplicated all their classified ads on their websites, and they have attempted to best Craigslist and its emulators by offering different features, new ways to search, and so forth. But the result is harder to use, and in any case why should you spend $100 putting something up for sale in the paper when you can post it on Craigslist for free? Why list a job for $200 when you can list it for $10?

(Craig’s a great guy by the way — check out the I Love Work interview we did with him on Make Work Meaningful).

Google? Craigslist? Blogs? All software. Software that is changing our culture.

Finally, how about:

“Do you think the massive changes in the music industry have changed our culture?”

It started with Napster (more software). And now, Apple — traditionally a computer hardware company — has blown past 10 billion song downloads from the iTunes Store. iTunes is now the number one music retailer in the world and features the world’s largest music catalog with over 12 million songs. A generation of kids, my own included, are growing up in a world where physical media is disappearing — CDs, records, books, newspapers — and being replaced by networked, portable, instant gratification-enabled purchasing devices. Having immediate access to the long tail of human knowledge from everywhere you are at every time of day will change our culture forever.

There’s no question software has changed the content industry and content is culture.

Here’s the thing: bad technology doesn’t change culture. You can take an offline, hierarchical, batch process like performance reviews and move it into an online form but it’s still the same old crap, now delivered in a synergy capturing ePile.

But, well designed, social software can change culture. Take the things that people already do — sharing photos, playing games, collaborating — and make them much, much more efficient. Build a platform upon which people can remix and they’ll rip, mix, and burn.

That’s what culture is: the way we communicate memes to each other. The way we pass knowledge down through generations. The way we encode the beliefs and values of our society into a shared set of behaviors and practices. Good software enables that. After all, five years ago, would you have considered putting your resume online for every to see? Now we all LinkedIn accounts.

The first wave of Enterprise 2.0 was built around idea that “these features worked in normal social software so let’s slap them on some Enterprise products and let them do their magic!” It was like wet fireworks: lots of buildup, ignition, lift off, fizzle, splat. The things that people do in ‘normal’ social software don’t work at work because the things people do when they’re socializing with their friends aren’t the same things they do when they’re getting work done.

The current wave, of which Rypple is proudly part, took longer to figure out which social behaviors drive need to be part of the workplace. Good software takes the things that people already do and makes it much more efficient. In the words of the Heath brothers in Switch, look for the bright spots. Here’s what they say about how to how to change things when change is hard:

When it’s time to change, we must look for bright spots — the first signs that things are working, the first precious As and Bs on our report card. We need to ask ourselves a question that sounds simple but is, in fact, deeply unnatural: What’s working and how can we do more of it?

And that’s what we’re trying to do with Rypple: finding the cultural bright spots from companies who get it, encoded in a easy-to-use software that people love, and amplifying the brights spots to change and build feedback cultures.

We believe that a new wave of enterprise and business software is being built today that will be pulled into companies and will change their cultures. Unlike the first wave of business software that was imposed on people, this next wave will be adopted and spread because it is built around people and what they really do, and not around processes we impose on them.

As Ben Horowitz wrote today about re-imagining enterprise software,

Rather than defining their business by their data model, customers [will] define their business by the real people and processes that they use. And the resulting applications [will] perform 1000X faster than their communist, excuse me, enterprise software counterparts.


Daniel Debow is a co-CEO of Rypple. Daniel was one of the founders and the VP of Corporate Development and Marketing for Workbrain, an enterprise software company. He holds a JD and an MBA from the University of Toronto and an LLM in Law, Science & Technology from Stanford University. He's a huge music fan, plays the bass (badly), and spends far too much time online. He lives in Toronto with his wife and son.