Given the hard time we have defining success in the security field, you’d think we must have at least a firm handle on failure. But that isn’t entirely the case. As both an entrepreneur and a security guy, I may have a different perspective on failure, which influences how I look at pretty much all our business activities. I read a lot of VC and entrepreneur blogs, not because I want to raise money – in fact I’d rather hook my soft targets to a car battery than take outside investment. But I need to learn about how folks are screwing things up and try not to do that.

Don Dodge’s short post, Failure is just experience on the way to success resonated with me. He talks about failing fast and the idiocy of the failure is not an option mantra. Of course, if lives hang in the balance, I’m good with doing whatever is humanly possible to avoid failure. But for a business? Give me a break. It creates a culture of risk avoidance, always a recipe for failure over the long term. Look at pretty much all big companies – they have this in spades. Their size and inertia may offset their lack of innovation for years, but ultimately these companies hit the wall because they get too big to remain nimble.

So what? How does this help you do security better? Well, there is one crystal-clear failure in security: the breach. That means something failed and data was compromised – simple. You try hard to respond effectively and move on. But let’s talk about another type of failure.

That’s the failure of a tactic, control, or product. You do all sorts of things that aren’t working – in many cases you know it’s not working. Let’s just pick on SIEM for a few minutes. Some organizations get tremendous value from SIEM, but I’ve met with countless other companies which do not. Not many stand up, own the project failure, and move on to something else that might work better.

Failure needs to be an option

These folks believe failure is not an option. They see tremendous political capital locked up in the tactic they decided on, and won’t risk looking bad by admitting failure. They’d rather keep throwing good money after bad, and wasting major resources that could be better used elsewhere to save face in the political meat grinder.

Most of the time they also fail agonizingly slowly. Many of these science projects require a significant amount of integration and professional services, further driving up the price and pushing out the timeline. I get that sometimes an initiative can have a happy ending even if things look pretty bleak during part of the process. But realistically, more often than not, it doesn’t get better. At least until you find your next gig.

But this isn’t the real driver for this dysfunction. There is very little incentive for small cogs in big wheels to stick their necks out and declare failure before they are forced to. Best case, you draw down your credibility. Worst case, you cost yourself a job before you needed to. Do you really wonder why most folks just sit on failure until the rotten fish stench becomes un-ignorable? Or why it usually takes a regime change to address all the hidden turds that were studiously being ignored, at significant cost to the organization?

Failing Gracefully

What can you do about it? If you work in an organization where failure is frowned upon, keep making deposits in the credibility bank and hope you have enough credit, then make a careful decision exactly when to admit the failure. Hoping the project will recover is not a strategy for success. These ongoing train wrecks represent sunk costs, so focus on cleaning these messes up as quickly as possible while keeping your job. Looking forward, you can change things, and that’s what you need to focus on.

You need to manage your projects a bit differently. See how you can break larger initiatives down into smaller ones, with defined exit points. Reduce financial and resource risk, and allow yourself some leeway to determine whether you are on the right path. Have a Plan B, if your best-laid plans end up being wrong.

If you are interviewing for a new gig, understand how the organization handles failure. Ask for anecdotes and stories about projects that went south. Did anyone live to tell the tale? Or are they all urban legends because all the bodies are buried throughout the organization? Ask how success is defined, and whether a similar amount of effort is spent on defining failure. Go in with your eyes open, and don’t have what sales folks call happy ears when you don’t get answers you like.

I do believe failure is your friend. Maybe that’s my own confirmation bias talking, because I have failed more than most. But regardless of your job role, you can embrace failure and do your job better for it. Really.