What, I’m sure you’ve been wondering, does successful spycraft have to do with the projects your organization undertakes?

Wonder no more. I’ve tracked down the answer, courtesy of Good Hunting: An American Spymaster’s Story (2014), whose author, Jack Devine, ran some of the CIA’s biggest, most complex, and highest-profile covert operations (he was the Phillip Seymour Hoffman character’s successor in “Charlie Wilson’s war” – the U.S. support for the mujahedeen’s resistance to the Soviet invasion of Afghanistan.

If you decide to read it you either will or won’t be put off by the author’s occasionally self-congratulatory tone, and might or might not be convinced CIA covert operations are as good an idea as he thinks they are. KJR doesn’t discuss foreign policy matters unless they’re directly related to information technology, and even then …

Whether you think covert operations are a good idea has nothing to do with they take. Turns out, a lot of it is (or should be) Project Management 101. It also turns out that whatever else Jack Devine is, he’s KJR’s kind of project manager: His list isn’t about what’s needed for covert ops to succeed. It’s a list of the factors without which covert operations (and your projects) are bound to fail:

  • Viable partners in place: In the world of covert ops this means there has to be a significant faction within a host nation that shares our goals and objectives and is willing to fight for them. In your world this means someone who matters in the affected business areas has to want it deeply enough to stick his or her neck out from time to time to help the project succeed.
  • Real-time, accurate information: In the world of spycraft this means information from foreign agents, not just technologically gathered intelligence. In your world this means you need a personal network that lets you know what the buzz is about your project.
  • Adequate resources: You might recall that nearly every Y2K remediation project succeeded. You also might recall that companies opened their checkbooks to support them. You also might recall business leaders who drew exactly the wrong conclusion … too many idiotically decided their success meant there never had been any risk. The right conclusion: While “throwing money at a project” doesn’t generally help, starving a project is usually much worse.
  • Bipartisan political support: In business, bipartisanship isn’t good enough, because few businesses are limited to just two competing factions. So from your perspective let’s call it multi-partisanship. Not everyone has to support a project for it to succeed, but enough have to that the political clout is on the project manager’s side.
  • A direct threat to U.S security: In covert operations, this means the adversary against which the covert operation is targeted must present a clear and present danger — covert operations aren’t something to undertake lightly. Projects in your world ought to have some reasonably direct connection to threats and opportunities in the marketplace.
  • Proportionality: Even the cleanest covert operation can cause “collateral damage” (the intelligence community’s clinical euphemism for “innocent bystanders can get hurt or killed”). In your world the situation is less extreme but still real: The expected value of a project’s outcomes must outweigh, not only its direct costs but also the intangible costs associated with the disruption it causes.
  • A reasonable prospect for success: For a covert operation, policy makers must have clear objectives and a fact-based assessment demonstrating that the operation is feasible. For one of your projects it’s usually a good idea to either determine that someone else has done something similar and succeeded at it, or to complete a so-called but usually mis-named “proof of concept.”

Devine makes the point that making sure these factors are in place is the responsibility of policy makers, not the CIA. KJR makes the point that business policy makers have a parallel responsibility, not the CIO.

Except that this is where the parallel breaks down. When we’re talking about the CIA and covert operations, even success can have grave consequences, so strong top-down controls are essential.

Keep in mind that instituting controls means establishing a system in which the default answer to any suggestion is “No.” This is rarely desirable. At best, it’s less undesirable than the alternatives.

Most businesses want, or should want to encourage innovation and initiative, something controls stifle through the EHL effect (epiphany half life) — the time needed for the enthusiasm for a new idea to be cut in half.

So before you subject proposed projects to too much vetting, ask yourself whether the loss of innovation and initiative is worth it.

See proportionality, above.