I can think of all kinds of ways CIOs could use Evernote, from jotting down key points at board meetings to scanning business cards at tech conferences, but it’s a bit of insight from its executive chairman that’s particularly worth capturing.

Speaking in a recent episode of the Tim Ferris Show podcast (to which I have become completely addicted), Phil Libin talks about some of the best advice he’s gotten in taking his productivity software app to more than 150 million users (and likely an IPO before too long). Among these was a formula of sorts he credited to Hiroshi Mikitani, CEO of Japanese e-commerce firm Rakuten: every time you triple in size, you need to rethink how you do things.

“When you’re just one person, you figure it out,” said Libin, who recently stepped down from LinkedIn and replaced by former Google exec Chris O’Neill. “Then you go to three people, and making decisions is different . . . how you handle payroll, how you schedule meetings, what communication you use, how you do budgeting, how you make decisions. Every explicit and implicit part of the company changes when it triples.”

The Problem Of Scale — In IT As Well As Business Growth

Libin was talking about scaling a company, but I think the same principle is often at work in enterprise IT when CIOs and their teams are trying to scale technology to meet business needs. Moving one workload to the cloud in a pilot project may be straightforward enough, for example, but complexity increases when that project grows by an order or magnitude, be it a tripling or some other amount. The same with mobile apps. You can build or deploy a few to selected users and departments, but the reason we don’t see or hear about a lot of “mobile-first” companies is probably because organizations underestimate the domino effect wrought by technology to their everyday processes.

Scalability, of course, is not limited to a group of entrepreneurs that become mid-sized companies. Libin said it can be even worse for large organizations. If they’re 10,000 employees, for example, it may take a long time before they reach the next threshold (which may or may not be 30,000). Knowing when to really reinvent yourself can be maddeningly elusive.

“Big companies are constantly pushing these, like, (expletive) innovation initiatives because they feel like, ‘Well, we have to do something. We have to do something!’ But they’re not actually connected to any fundamental change in the company,” said Libin.  “They’re just floating around by themselves. So by having this mismatch between when things actually change and when you actually feel you should do something, small companies get in trouble, big companies get in trouble. Just being mindful about that is super eye-opening.”

The Tipping Point For Organizational Change

Change management is something that obsesses a leader like Libin, given that Evernote is basically designed to replace older forms of capturing and managing information. In fact, he offered another interesting theory as to why companies can’t seem to transition to new technologies or ways of working more quickly.

When you change jobs, Libin said, you tend to take stock of what worked and what didn’t in your previous job, and what you might do differently in your next role. As the average tenure of knowledge workers shrinks in places like Silicon Valley, people may be more predisposed to try out apps and other fresh approaches to getting things done.

“You can measure how long a fundamental corporate change will take just on the number of job cycles  that it requires,” he said. “So something as profound as getting rid of email could take three entire cycles of people changing their jobs.”

There’s not a lot CIOs in Canada can do about that, of course, other than encouraging staff (and themselves) to occasionally step back and adopt the mindset of someone making a career transition. That, or perhaps conducting their own experiment by seeing how many enterprise employees would be happier working with something like Evernote.

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