The 7 Deadly Sins of Software Selection

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Q: How many doomsday prophets does it take to change a light bulb?
A: None. The light is still on.

“Knock knock.”
“Who’s there?”
“The Raptured. SURPRISE!”

Thank you, thank you, don’t forget to tip the archangels, I’ll be here all week (according to best estimates).

You may have heard recently about Harold Camping, the radio host who predicted that The Rapture would take place May 21.

Fun fact: Did you know that Harold Camping’s tribulations mirror those of a software selection project gone terribly awry?

Answer: Yes! That’s because he committed the 7 deadly sins of software selection. Here’s how you, too, can send your software selection project straight to hell:

Deadly Software Selection Sin #1: Setting unrealistic deadlines

The Harold Camping sin: The Rapture, originally scheduled for May 21, has since been revised to October 21. Now, in the context of a 2000-year project path, a slippage of 5 months is truly not bad.

However, in the context of a deadline that holds careers and life savings in the balance, close isn’t quite good enough (see also: 40 Ways to Crash a Product Launch, from Harvard Business Review).
Why this sin will consign your software selection project to the flames of hell: Unrealistic deadlines are a sure-fire project killer—nothing says “bad decisions” quite like stress, haste, and ad hoc shortcuts.

This goes for each step of the software selection process, from requirements gathering to go-live and post-implementation. But in particular, if an over-aggressive timeline has landed you behind the eight-ball, you’re going to get hammered when it comes to, e.g., vendor negotiations.

Because you know how vendors resolve tight timelines? That’s right, they throw consultants at you. Veeeerrry veeeerrry expensive consultants. And that’s just the immediate cost. The long-term cost? Just ask Hershey [PDF download]. 

Deadly Software Selection Sin #2: Failing to get user buy-in.

The Harold Camping sin: As anyone who watches television knows, “enough belief in something will actually cause things to happen” (source: Clap Your Hands If You Believe). Sadly for Camping, however, his brand of theology failed to garner the support of a number of believers, including the Protestant and Catholic churches, thus undermining Camping’s inevitable fall-back position.

You know the position I mean: that Rapture Thing, it was just spiritual. Which is why you couldn’t see it, duh. (Every good manager should adopt this position. Hey dude, here’s your spiritual pay raise, man, chill.)

Why this sin will consign your software selection project to the flames of hell: Change management is notorious for being one of the most crucial and frustrating parts of an enterprise software selection project. It can kill your selection project deader than American LaFrance.

And that’s if your users have bought into the project.

A large-scale enterprise software implementation will lead to changes in the way your business processes work, changes in responsibility for different employees, and changes in expectations from management. With failure to get user buy-in, these changes can severely cripple the effectiveness of your software solution through misuse or non-use.

Be sure to get user buy-in early (at the requirements-gathering stage) and often. The best way to get buy-in from a group is to offer them a voice (and proof that you’re listening).

Deadly Software Selection Sin #3: Succumbing to undue influence

The Harold Camping sin: You know that little voice inside your head? The one that starts sentences with words like “I wonder why no one’s ever tried this before,” and then cackles evilly, and then uses words like “oops”? Yeah, you need to downgrade that voice to “not a major influencer.” To stop you from doing crazy stuff such as, you know, announcing the end of the world.

Why this sin will consign your software selection project to the flames of hell: Does your CEO play golf? Does your CEO play golf with other CEOs, some of whom are CEOs of major software vendors? Is one of these vendors suddenly on your very very short list? There’s no nice way to say this, so I’ll just come out and say it: Cover. Your. Assessments. Your software selection methodology must provide for full documentation and accountability through each step of the selection process. See TEC’s recommendations for a best-practice selection methodology.

Deadly Software Selection Sin #4: Over-expressing your requirements
The Harold Camping sin: Camping had to go and ruin his very basic going-to-heaven requirement with a bunch of other, weirdly specific requirements. Such as “it starts at 6PM sharp.” And New Zealand gets it first.

Why this sin will consign your software selection project to the flames of hell: Sometimes you get bogged down in the way you do things. And sometimes you get bogged down in costly (and often unnecessary) customization, in order to get new software to match your business processes. Don’t forget: many software vendors spend years—and tens of thousands of labor-hours—in determining best-practice processes for your industry. Take advantage of that.

Related badbanana quote: “Dr. Frankenstein could have saved himself a lot of time and anguish by simply not sewing on the arms and legs.”

Deadly Software Selection Sin #5: Watching TV
The Harold Camping sin (as featured in New York Magazine’s conversation with Camping):
Q: What will you be doing on that day? Are you just waiting for the earthquake, are you having some kind of ceremony?
A: There'll be no—it’ll just be simply waiting, and the likelihood is that I'll be doing what everybody else will be doing, which is listening to the radio or watching TV…

I, for one, look forward to Fox News coverage of The Rapture. Especially the typos.



Why this sin will consign your software selection project to the flames of hell: There’s real danger in watching the metaphorical TV, i.e., in passively letting the project details take care of themselves. Because they won’t. See Finagle’s Law (O’Toole’s Corollary in particular). See also The Devil’s in the Details (Based on a True Story).

Deadly Software Selection Sin #6: Overlooking the fatal flaws
The Harold Camping sin: In the spirit of fatal flaws, I would like to highlight Camping’s dubious reliance on biblical numerology. As reported by the San Francisco Chronicle:
"5 times 10 times 17 is telling you a story," Camping said. "It's the story from the time Christ made payment for your sins until you're completely saved. I tell ya, I just about fell off my chair when I realized that."

In other chair-falling news, Camping’s full name, Harold Egbert Camping, anagrams to “God Regret Banal Chimp,” some subject-verb confusion possibly arising over uncertainty as to the nature of God’s hypothetical corporeal form(s). It also anagrams to “God Embracing Rat Help,” but pointing that out is just sort of mean-spirited and maybe theologically unsound.

Why this sin will consign your software selection project to the flames of hell: Here’s a great example of what can happen if you and your vendor are not on the same page with respect to fatal flaws (from the TEC article Fatal Flaws and Technology Choices):
One meat processor (which will remain nameless) recently embarked on an application software project. Of course, catchweight was a must-have for its business. The company asked the software salesman if the software had catchweight, and after having to explain the concept at great length to the salesman (a bad sign), the salesman said “no problem.”

It later transpired that the salesman thought that catchweight was only a simple pricing issue. The meat processor did not probe into the details, was satisfied that catchweight was “available,” and signed a contract. The result: the project overran the budget and missed the schedule significantly… The meat processor had to write a significant amount of custom code just to get pricing working correctly.

If you and your software vendor are not speaking the same language, you risk similar delays, if not outright lawsuits. Make sure you’re all on the same page. [Related resource: TEC’s collection of detailed, customizable enterprise software feature lists.]

Deadly Software Selection Sin #7: Failing to get executive buy-in.
The Harold Camping sin: Ha ha ha ha!

Why this sin will consign your software selection project to the flames of hell: Securing strong management support is critical to successful cultural change in any organization. Executive buy-in provides the infrastructure for driving accountability, transparency and, above all, credibility throughout the organization.

Executive sponsorship provides the necessary leadership to successfully drive the project, weed out any cultural resistance, and sell its benefits to the organization as a whole.

It’s your turn now. What other software selection sins would you include in this list? Let me know in the comments below!

See you soon.
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