• The Cathedral and the Bazaar by Eric S. Raymond
• The Wisdom of Crowds by James Surowiecki
• We Are Smarter Than Me by Barry Libert, Jon Spector, Don Tapscott
• The World Is Flat by Thomas L. Friedman
• The Innovator's Dilemma by Clayton M. Christensen
• The Long Tail by Chris Anderson
• The Speed of Trust by Stephen M. R. Covey
• What Got You Here Won't Get You There by Marshall Goldsmith
• Outsourced (the movie)

Also remember that I mildly panned Digital Economy by Harbhajan Kehal and Varinder P. Singh; my assertion was that the next 10 years will bring about a social economy instead, one that includes the digital natives you’ll all be hiring and selling to now or very soon. They’re the ones who are building it, so you might as well adapt.

I’ve often read people who say that we (security, risk management) need to “think like the attacker”.  And when you read this sort of article, that usually alludes to trying to anticipate the tactics an attacker might use to mess with your C, I, or A.  Smart stuff, that, and very useful when architecting security solutions.  But as I was training some folks Monday, I was thinking in the back of my head about Threat Capability (TCap) in FAIR.  As you might know, we like to estimate the capability of a threat to apply some level of “force” against our assets.  This ability to apply force is a byproduct of the attacker’s skills and resources.  And thinking of how an attacker applies skills and resources, I came across another way we might “think” like an attacker.

Traditionally, I’ve thought of “skills” as being a byproduct of the toolset an attacker has.  This mindset probably stems from my time with Penetration Testing teams, where in the process of scoping the  PenTest I would ask our clients to select the level of effort that they wanted us to throw at them.  If a client chose “high” we’d throw every ‘spoit we had at them.  If they chose “low” we’d limit ourselves to a more commonly available toolset.

But while the resources part of TCap is time & materials (money) - the skills are really more than just the toolset.  Skills would include the ability of the attacker to be creative and innovative.    As an example of that innovation from those PenTesting days - when we got a “high” effort request, we would always try to couple that with some “social engineering”-type of attack, or some unique means of delivering an existing exploit.  Our creativity was not necessarily a byproduct of a unique exploit or tool we had, but the process by which we might deliver pre-existing or commonly available exploits.  I remember when we first got ahold of a handful of 32mb thumb drives (hey, 32mb was huge back then) and “dropped” a few in the lobby of a client’s retail space.  The keystroke loggers and phone-home script weren’t new, but using the thumb drive as delivery vehicle certainly was.

So I’ve started to really think about this concept of innovation, and how if “thinking like an attacker” means to be innovative, we ought to do the same.  I’ve been thinking of two main categories of innovation this morning.

INNOVATION

The first I’ll call Technology Innovation.  And by Technology Innovation, I mean some new, unique, “ahead of the curve” technology that an attacker can use against us.  The obvious example of which is a zero-day.  It’s that “high” tool set our PenTesters would use against the clients.  For security departments, this might be the latest security product designed to enhance our ability to P, D, and/or R.

Alternately, we can be creative in the way we deliver (manage) existing technology.  I think of this as Process Innovation.  It’s doing more with what we already have, just like the PenTest team would be creative in the delivery of an existing exploit.

Unfortunately for us - attackers have traditionally had quite a leg up on us in terms of Process Innovation.  It is much easier fro them to be creative, as they are free of political constraints and bureaucracy.  In contrast, when the security industry tries Process Innovation, the results are checklists and “standards”.  It’s committees and consensus.  An extreme example of which might be something like SABSA - a great work if you want to understand some very smart people’s comprehensive understanding of organizational security  - but the “adoption”of which will do very little to help you be innovative in P/D/R.

It’s worth noting that ultimately, this is one reason I don’t like regulatory compliance efforts - they simply serve to prove how mundane your security department is,  wasting valuable resources that could be spent on creating ways to be more effective.

PROCESS INNOVATION AS A SUBSTITUTE FOR TECHNOLOGY INNOVATION

As we come to the close of 2009, some surveys suggest that security spending isn’t horribly impacted yet by the economy (the latest from E&Y points to only 5% of their respondents getting budget cuts).  But if this is a protracted downturn, and because InfoSec is an operational expense, I would expect cash to become more and more difficult to keep.  And regardless if technology spends do slow, I believe it makes sense to think about Process Innovation because I see Process Innovation as a means to increase effectiveness without significant capital expenditures (effectiveness increases because our ability to manage risk has a direct correlation to the amount of risk we have).

The bad news is, of course, that great innovation is hard.  It is R & D.  Failure is usually a pre-requisite to success.

The good news is, our current state is so bad that many of us don’t need to come up with a whizbang new way of reducing software defects in the SDLC as innovation.  Simply inserting a risk analyst into the PMO’s processes might count as a big enough victory. Be cautioned, though,  that if we’re substituting the risk reductions provided by technology acquisition - Process Innovation might actually be even more “expensive” as it requires us to expend political capital.   But there are (forgive the term) innovative ways to spend this political capital.

For example, by taking a second now and figuring out the 3 things that the rest of the organization can do to make your life easier, when that “I need to reduce your budget” talk comes, you can be prepared to negotiate.  Get a political capital “loan” or “investment” from the C-Suite reducing your budget.  Something to the effect of: “I expected this, and am happy to give up my budget.  But if our tolerance for risk hasn’t changed, what I’d like to do is get you to personally back my office on three projects I’ve identified that can reduce our risk without requiring significant capital expenditure.”

[Q] I have been collecting accounts of your meeting with David Petraeus in Baghdad. And you had [inaudible] after he had made a really strong pitch [inaudible] for maximum flexibility. A lot of politicians at that moment would have said [inaudible] but from what I hear, you pushed back.

[BO] I did. I remember the conversation, pretty precisely. He made the case for maximum flexibility and I said you know what if I were in your shoes I would be making the exact same argument because your job right now is to succeed in Iraq on as favorable terms as we can get. My job as a potential commander in chief is to view your counsel and your interests through the prism of our overall national security which includes what is happening in Afghanistan, which includes the costs to our image in the middle east, to the continued occupation, which includes the financial costs of our occupation, which includes what it is doing to our military. So I said look, I described in my mind at list an analogous situation where I am sure he has to deal with situations where the commanding officer in [inaudible] says I need more troops here now because I really think I can make progress doing x y and z. That commanding officer is doing his job in Ramadi, but Petraeus's job is to step back and see how does it impact Iraq as a whole. My argument was I have got to do the same thing here. And based on my strong assessment particularly having just come from Afghanistan were going to have to make a different decision. But the point is that hopefully I communicated to the press my complete respect and gratitude to him and Proder who was in the meeting for their outstanding work. Our differences don't necessarily derive from differences in sort of, or my differences with him don't derive from tactical objections to his approach. But rather from a strategic framework that is trying to take into account the challenges to our national security and the fact that we've got finite resources.

I have made this general point again and again -- about airline security, about terrorism, about a lot of things -- that the person in charge of the security system can't be the person who decides what resources to devote to that security system. The analogy I like to use is a company: the VP of marketing wants all the money for marketing, the VP of engineering wants all the money for engineering, and so on; and the CEO has to balance all of those needs and do what's right for the company. So of course the TSA wants to spend all this money on new airplane security systems; that's their job. Someone above the TSA has to balance the risks to airlines with the other risks our country faces and allocate budget accordingly. Security is a trade-off, and that trade-off has to be made by someone with responsibility over all aspects of that trade-off.

I don't think I've ever heard a politician make this point so explicitly.