I stumbled on my last employer’s shutdown plans while rummaging around my old email archives. Those messages were from today’s date 3 years ago – not coincidentally the day Rich and I began to discuss me joining Securosis. At milestones like this I tend to get all philosophical and look back at the change, and what I like and dislike about the move. How do I feel about this change in my career? Where are we as a company, and is it anywhere near what we planned? I had no idea what an analyst really did – I just wanted to help people understand security technologies and be involved much more broadly than just database security. I kinda thought I was getting out of the startup game, but Securosis has the feel of a startup – the freedom to follow our vision, the pressure to focus on what’s most important, the agility in decision making and long hours. But it also feels like people appreciate our take on what analysts can be, which makes me think we have a shot at making this little shop a success.

Personally, leaving 20+ years of pure technology roles was a big leap. Actually I had no single role – any day it may include architecture, product strategy, development, design, evangelism, and team management. But being able to cover a dozen areas in security – and the independence to say whatever I think – gives me a lot of satisfaction. And I love doing research. Unfortunately the single biggest detriment of the job – and it’s a big one – is writing. It’s what I spend the majority of my day doing, and it’s quite possibly my worst skill. I find writing to be a slow and painful process. It’s common to go two days without writing anything substantive, followed by a single day where I get crank out 15 pages. That’s nerve-racking when you have deadlines – pretty much every day. I never had this problem coding – why the English language causes me problems that neither C nor Java ever did remains a mystery. Learning how to write better is one of the more painful processes I have been through. And for those of you who sent me hate mail early on – one of you called me ‘Hitler’ for atrocities against the English language – you are totally correct. A-holes, but still right.

From a business standpoint, if there is one singularly important difference you learn when moving from technology to an analyst role, it is perspective. A vendor’s view of what a customer needs is usually off the mark. Vendors do a lot of searching for the ‘secret sauce’, and constructing very logical arguments for why their particular product is needed – even a ‘must have’. But logical vendor arguments are usually wrong and don’t resonate with customers because they fails to account for the limitations faced by businesses. Customers each work within a set of existing constraints – some mixture of perfectly logical and perfectly absurd – which binds them to a specific perspective and approach to problem solving. I constantly hear vendors say, “Everyone should do X because it makes sense,” to which customers say nothing at all.

This is even harder for startups with innovative technologies. How do you know the difference between “Customers just don’t get it yet” and “This innovative product will never be adopted”? The evangelism to educate the market is tough, and it’s easy as a vendor to close your ears to negativity and bad press because they are just part of the evolutionary process. The ability to shine a light on these messaging and strategy issues, and realign companies with customer requirements, is a big part of the value we provide. Vendors are so busy spinning – and get so used hearing to ‘No’ for both good and bad reasons – that they lose perspective. I’ve been there. Several times, in fact. For whatever reason customers tell analysts stuff they would never tell a vendor. I get to see a lot of the inner workings of IT organizations, which has been very educational – and unexpected.

Three years later I find I have two great business partners, I get to interact with extraordinary people, and I work on cool projects. I do really love this job.

On to the Summary:

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Blog Comment of the Week

Remember, for every comment selected, Securosis makes a $25 donation to Hackers for Charity. This week’s best comment goes to Aaron Schaub, in response to Defining Failure.

Great post. Risk and failure have been topics I’ve been pondering a lot lately.

We INFOSEC guys sometimes forget that business is all about risk taking. That’s why there’s profit. It’s a little entertaining to watch the heads of INFOSEC professionals explode when they grasp some of the risks the business willingly takes and the potential failure implied.

As INFOSEC leaders, we need to get a handle on risk and failure. We need to understand the risk tolerance of the organizations we support and adjust our risk tolerance accordingly. We need to put this into perspective and create an environment for our teams that acknowledge and embrace that tolerance. It isn’t easy as we security types tend to be a risk-averse lot. But, I’ve noticed more cooperation from the business when my team’s risk and failure tolerance is inline with the business’s. I think that helps us fail gracefully too.