The False Choice Between Enterprise IT and Startup IT

There is much to like in the new book Rework, from the founders of 37signals. The book, geared toward small businesses, startups and entrepreneurs, is a collection of common-sense and (self-described) contrarian views on everything from the work hours necessary to be successful when starting a business…

“Send people home at 5…You don’t need more hours, you need better hours.”

to the need to focus on building your company rather than on external financing or the minuscule odds of making a big payoff someday…

“You need a commitment strategy, not an exit strategy. You should be thinking about how to make your project grow and succeed, not how you’re going to jump ship. If your whole strategy is based on leaving, chances are you won’t get far in the first place.”

Much of the commentary on the book has centered around whether the success of 37signals as an independent, profitable software operation is applicable to the majority of small and internet-focused businesses.

For me, the book is one more data point confirming a theory I have held for sometime; that we are moving toward an environment in which there really are two “camps” of IT professionals (and IT shops). On one extreme are enterprise IT and those within it, and on the other startups and small businesses. As in most tribalism, each extreme is easily painted with incorrect stereotypes, and a false choice is presented between them – you can belong to one camp or the other, but not both. Its easy to look across the chasm at the other side and make little effort to understand their real challenges or what might be learned from them. If an individual moves between camps, it is very likely by leaving the enterprise world for the small-business world, never to look back.

Let me take a stab at the negative generalizations:

Enterprise IT Professionals:

Work for large organizations; like job security more than risk and potential reward; may be more concerned about process/planning than outcomes; are comfortable in command and control environments, are OK spending time in endless meetings; may not agree with the inefficiency they observe in their organizations but don’t have the drive or influence to change the situation.

Startup IT Professionals:

May have never worked for a large organization and have little desire to; work best independently rather than as part of a large team (and may not have the skills to navigate a large team environment); are willing to take substantial risk; expect to choose their own tools for the job and have complete control of processes; very comfortable with ambiguity and a lack of detailed plans or requirements, often with negative consequences; have little patience for inefficient methods, teams or organizational management.

As I said, incorrect stereotypes, but does this ring a bell?  Right off the bat, many of the examples in Rework may not directly apply to large enterprises with complex products, shareholders and a Board of Directors to report to…

“Planning is guessing…Why don’t we just call plans what they really are: guesses. Start referring to your business plans as business guesses, your financial plans as financial guesses, and your strategic plans as strategic guesses. Now you can stop worrying about them as much.  They just aren’t worth the stress.”

or real, established competitors in the marketplace that they need to respond to and win against…

“Build half a product, not a half-assed product… You have limited time, resources, ability, and focus. Trying to do ten things well at the same time? Forget about it. So sacrifice some of your darlings for the greater good. Cut your ambition in half.”

If you are in the enterprise space, you may have rolled your eyes a few times back there. But lets face it:  The IT planning process for many large organizations is broken, as seen by the need to add large contingency factors to every IT estimate made. Many enterprise projects do suffer from feature bloat, with each new “toxic meeting” (the book’s label) adding yet more unneeded items (and risk) to an already risky endeavor.

For me, the interesting part of the discussion of enterprise versus startup worlds isn’t so much around which camp is best, but rather how the best parts of the startup culture described in Rework (speed of progress and in changing direction, comfort with ambiguity, etc) can be leveraged to move the enterprise world forward.

Some Examples:

• Each of us would prefer to pick our own tools for the job, and the majority of startup-types I have met do just that, from the brand of laptop/OS they prefer to their development frameworks. If they want a tool, they install it. Does this personal flexibility scale to an organization that needs to efficiently manage 10,000 users and laptops around the globe? No, but having accepted the fact that some centralized control and standards are necessary, would there be value in letting the enterprise IT staff have significant input into the tools they are using on their locked-down laptops, rather than that decision being made by a disconnected management team just returning from an expensive dinner with a software vendor?
• If a large organization’s IT developers have secretly started using Amazon’s AWS to spin up testing servers rather than wait 4 weeks to get an internal procurement accomplished, is that a signal that they aren’t team players, or just their attempt to manage in a world that is moving much faster than your internal processes/infrastructure are built for, and perhaps some changes need to be made?

For these and dozens of other examples, it would be easy to give up on the often ponderous world of the enterprise and look for greener pastures in the startup space, where (supposedly) everything moves exponentially faster and individuals have ultimate flexibility. But isn’t there an interesting challenge in this problem itself?  Isn’t there huge potential value-add in attempting to bring the large IT organization along the path to greater agility and speed-to-market, while also trimming costs?  Rather than ending the discussion at picking sides, how do we make a positive change in the enterprise space?

A generation of IT graduates are leaving their dorm rooms (where they likely know someone working on a startup) to enter the workforce.  What attraction do they see in the enterprise IT world?  Do they see it in terms of the negative stereotypes presented here?  How many will make the decision to join that world?

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Tagged as: Corporate Culture, Management & Governance