Taking Care of Business

I remember back in early 1996 arriving home from work and telling the future ex Mrs Langford that was going to be very busy “for the next two to three months”. There was a project going on that I decided I was going to get involved in (outside of my normal IT Manager day job) and that it was going to be good for my career. In modern parlance, I had decided to “lean in”.

Those busy two to three months ended for me on the 10th September 2017. I had pushed myself professionally as hard as I could, burnt the candle at both ends, worked long hours, was only off work sick when I euphemistically “called in dead”, accrued millions of air miles, and was ostensibly successful in my career. Without wishing to dwell here on the events of that fateful night/morning in September 2017, I had reached the end of the line; all of that work and effort had ultimately netted my severe anxiety and stress, diabetes, alcoholism, and a desire to make it all stop very violently.

All of which brings us neatly to right now. I am currently off work sick. I’m very likely to head back tomorrow 9even though I am not 100%, but boredom is a keen medicine sometimes), but I have had the best part of five working days of, plus a weekend in between. I had been feeling under the weather for about a week or so beforehand, but at about midday on my first day off I decided to just switch off my computer and go to bed, and there I more or less stayed for the best part of a week. I had tested positive for COVID, but a few days later that was now negative and I still felt like a bag of rusty spanners had taken residence in my lungs, and my energy levels were depleting like a Death Star tractor beam. Looks like I worked through a second bout of COVID and then got taken down by another virus; but those are details for me and my GP and work HR I guess.

But “SO WHAT?!” I hear you cry? Well, throughout these last few days of being off I made a conscious effort to disconnect from work as much as possible and focus on my recovery. I learnt my lesson those few years back, and realised I needed to get myself back to fitness, despite the many pressing deadlines and meetings I was missing, and the importance of the work I was doing. I focussed on myself and my health as I knew I don’t want to go back too early and jeopardise not only my health but my work performance.

And you know what? Despite everything I had experience before and told myself, I still felt guilty about taking the time out.

This shouldn’t come as a surprise to anybody, anywhere though, not least the information security industry. A few weeks ago, my good friend and all round good chap Sarb Sembhi, who along with Peter Olivier and Paul Simms authored a paper on Mental Health in Cyber Security, and of which I was asked to peer review. I will leave you to read the paper yourself, but the figures in there are both unsurprising as well as making for uncomfortable reading regarding anxiety, depression, anger, alcoholism etc..

I was asked by a client over dinner recently “what keeps you up at night?”. Obviously they were fishing for gossip/insight into the state of our joint business, but I told them that basically nothing does because after my life changing experience back in 2017, I refuse to get stressed or anxious over work matters because it simply isn’t worth it, especially as I am not CISO for something that may save/take lives. And yet here I am feeling guilty about taking maybe another day off sick, and deciding to go back even though I am still not breathing right and feeling fatigued. Surely I should know better?!

To be clear, we are (normally) compensated well and a have privileged positions at work to get the job done properly; we have responsibilities to our colleagues and to the clients and markets we support to do the right job and put the effort in, and frankly most of us even enjoy our jobs. But I can absolutely guarantee you that none of that is worth anxiety, depression, anger, diabetes, alcoholism and suicidal tendencies if that pressure to perform is maintained indefinitely.

Taking care of business ultimately means taking care of yourself first.

I am going to be at InfoSecurity Europe in a few weeks time on stage with the Sarb and Peter, authors of the above mentioned Mental Health in Cyber Security paper.

Links to other interesting stuff on the web (affiliate links)

What Exactly is the Cyber Scheme?

Solving today’s Security Challenges With Device Centric SSE

Sneaky Tricks In Enterprise Pricing

Beer, PowerPoint and Politics

Gone are the days when being a CISO (or even just ‘the security guy/gal’) was about actual information security or IT security. Even the term IT Security is outdated now and emphasises a one-dimensional view of what security is really about. However, I digress…

The Information Security element of CISO is correct, but for various reasons, the CISO’s role is very different from what it was a decade ago. The role then required a strong technologist who understood the firewalls, their rules, the cryptographic controls and even how to code hotfixes on the fly. This isn’t surprising given the role almost wholly came from an IT background; after all, back in the day, mere lip service was paid to the human element, and the legal considerations were considered simply “someone else’s job”.

I was often asked what my job as a CISO entailed, and because I didn’t initially understand what I had actually got myself in for when I took on my first CISO job I used to jokingly say;

PowerPoint and politics

Me. Back Then.

The odd thing is that this response is not far from the truth. My role became significantly less about my understanding of specific niches of information security knowledge and more about putting across to the business what this information security lot was all about and how it helped the company stay competitive, out of trouble or even just in business. The more I was doing this, the more I was embroiled in the day-to-day machinations of how a business works and the inescapable conclusion I came to was this; even if information security is seen as essential to the business, it is still just one voice of many that are trying to influence, cajole and be heard.

Moreover, this is where the politics come in, unfortunately. It is human nature and the way of businesses around the world. Politics is everywhere, and any CISO who doesn’t see and at least understand what is going on is, at best, going to be ignored and, at worst, eaten alive.

Which brings me to my second quote from me (well, it makes attribution a whole lot easier, doesn’t it?);

The purpose of a CISO is not to make the company more secure per se, but rather to help it sell more beer/widgets, increase shareholder value (as appropriate), and let the business make risky decisions more easily… through the judicious use of security

Me, Just now. Again.

The CISO should not be concerned with the name on the front of the firewall or the specifics of the latest penetration test. Instead, they should focus on how best to align their security services to the business and ensure security isn’t just a cost centre but a capability that allows teams and the company to run faster, more efficiently, and with less risk.

That doesn’t take technical knowledge; that takes strategic and business knowledge.

Links to other interesting stuff on the web (affiliate links)

Shift Gears: How to Leverage Data-Centric Security Controls in AWS

Changes to the OWASP API Security Top Ten 2019 to 2023

Cybersecurity as an Operational Effort

CISO Basics, Part 2

In the last post, I looked at some of the less apparent activities upon becoming a new CISO, namely:

  1. Stop thinking that infosec is your business.
  2. Stop making technology purchases.
  3. Ask your vendors to explain what you have in your services inventory.

In this post, we will take this a step further and closer to actual business as usual and maintaining your security team as a functional part of the organisation.

Don’t say “NO!” to everything.

This is an obvious thing to do, but it is much harder to do in practice. The reality is that this requires a complete change in mindset from the traditional view of the everyday CISO. As a species, the CISO is a defensive creature who is often required to back up every decision and be the scapegoat of every mistake (see One CISO, Three Envelopes https://thomlangford.com/2014/12/01/three-envelopes-one-ciso/) and generally rubber-stamp choices that are out of their bailiwick and control.

The mindset shift requires a leap of faith wholly because of this perceived threat of blame and accountability when, in fact, it does just the reverse. 

It starts naturally enough with the language that is used by the CISO and the team, for instance, changing the Change Approval meeting to the Risk Review meeting and not communicating a yes/no or go/no-go response to changes but rather a level of risk associated with the request and alternative approaches as appropriate. There is a need to communicate this shift in the culture, of course, but people will see that they are accountable for decisions that affect the business, not the security team. Shifting the mindset away from being a gatekeeper to a security team that provides sensible and straightforward advice based upon clearly understood risk criteria is a fundamental step towards avoiding being known as the Business Prevention Unit. Politely correct other’s language when they mention an action that requires sign-off or approval from “Security” and help them understand their role in the business decision.

This approach does not require a snap of the fingers for 50% of the problems to go away. Still, carefully planning and educating your stakeholders alters the impact you can have on the business dramatically for the better. It also allows you to more easily draw a line between the activities of the security team and the company’s performance, all for the price of merely no longer saying “no”.

Stop Testing Your Perimeter

What? Are you serious?! 


As you enter a new environment, you will be taking many critical pieces of information on trust and from people with vested interests in their careers, livelihoods and reputations. Your arrival upsets the status quo and has the potential to disrupt the equilibrium; all reasons to not always be forthcoming with every piece of information you request. It isn’t about people being dishonest or deliberately misleading you, but merely being complex, multi-faceted human beings with multiple drivers and influences.

Your perimeter is one of the fundamental pieces of your information security puzzle. Despite cries of “the perimeter is dead”, it remains a prominent place for attacks to happen and where you should feel fully confident that you know every node in that environment to the best of your ability.

Whatever your testing cycle is, suspend it for some time and conduct as complete an investigation as possible into precisely what your perimeter comprises. It can be done automatically with discovery tools, manually through interviews with those responsible, visually in data centres (where you have old school “tin” still being used, and any combination of the above. You will likely find devices that you, and probably existing team members, weren’t aware of, especially with the proliferation of the Internet of Things devices being used throughout the enterprise now. Did facilities install a new access control system or room booking system? Did they consult IT, or more to the point, you?

It sounds like the stuff of legend or the script to the Ocean’s 11 movies, but do you remember when a Las Vegas casino was broken into… through their fish tank? Knowing what devices are where on your network and perimeter is vital and must be considered table stakes in any decent security programme. An alternative is simply a form of security theatre that gives the impression of security and does nothing but create a false sense of security. A cycle of no testing is worth discovering what you don’t know because you can do something about it.

Building your plan

Now you have a grip on your environment in a relatively straightforward, simple, effective and quick way. Through this process, you will ascertain your stakeholders, advocates and even a few potential adversaries. Then, armed with this information, you can provide an accurate picture of the business to the business in a way that makes sense and displays a grasp of the fundamentals.

Building your plan will always start with your initial assessment and what needs to be done to become operational or steady-state. The trick, however, is to ensure that this baseline achievement is perceived as the end state of security but rather merely the first stepping stone to ever more impressive services, capabilities and ultimately, profit and growth for the company.

The plan itself, however? That is yours and yours alone. Although other posts in this Blog will help as you plot your course into the future, nothing will replace your understanding of the local culture, organisation and, ultimately, what you need to achieve to meet the expectations of the business leadership. Know what the rules of your organisation are, when to adhere to them, when to bend them, and most importantly, when to break them (but only when experience tells you it is the right thing to do):

“The young man knows the rules, but the old man knows the exceptions.” 

Oliver Wendell Holmes

Be the Old Man, be the CISO.

Links to other interesting stuff on the web (affiliate links)

5 Ways Penetration Testing Reduces Overall Security Costs

Avoiding Security Theater: When is a “Critical” Really a Critical?

Game of Life Security and Compliance Edition

CISO Basics, Part 1

So you want to be a CISO? Perhaps you want to be a better CISO? In many cases, you could pick up a book, attend a conference or even talk to some peers and colleagues. Of course, there will be some good advice in these approaches too, but you don’t want to be just any CISO; you want to be THE CISO.

Across two blog posts, I will look at some of the more unexpected but necessary activities you can do from the moment you start in a new role or start with a new approach to being a CISO. Some may be counterintuitive; some may be a little odd, and you may even disagree with a few. But, whatever you feel about them, they should start you thinking about different ways to approach your role and how you see the contributions you make.

In summary, in this particular post, you will learn to:

  1. Stop thinking that infosec is your business.
  2. Stop making technology purchases.
  3. Ask your vendors to explain what you have in your services inventory.

Stop Thinking InfoSec is Your Business

As a CISO, your primary purpose is not to secure the business; as odd as that may sound, it simply isn’t. Instead, the objective of a company is to sell more stuff, increase profit and maximise shareholder value (there are exceptions such as charities, government and the like, but they still have goals that include maximising value nonetheless).

If that is the case, your purpose is to help it achieve that goal through your activities. However, if you put your (security) activities ahead of those of the business, you are, ergo, hindering its ability to achieve its goals. So flip the situation around and ensure that when you come into the picture, you are fully cognizant of what your organisation does, its goals, ambitions and vision. Then, look at how your security team can make that a reality. Simply slapping security measures onto the business without regard for its purpose and intent will, at best, cause friction and disgruntlement and, at worst, diminish its business operations.

Read the company report, talk to the CFO, talk to people on the shop floor, the road warriors, delivery leadership, and, wherever possible executive leadership. Understand where the business came from, its roots, its beginnings, the founding values and vision, and even how it has evolved (if at all) over the years. By doing this, you will understand how you and your security team can help. Then, and only then, can you start to build your services and security posture.

Stop Your Technology Purchases

Unless the ink is drying on the cheques, you should pause purchasing until you have a better idea of the business. This makes completing the first step all the more critical, as some of the purchases may be vital. However, purchasing something that aligns differently with your new way of thinking about the business makes no sense, and significant amounts of money can be wasted and misdirected.

You may find much pushback from various stakeholders in the business, mainly as their pet projects and mini-kingdoms rely on those purchases. As a result, you are stymying their efforts and potentially making them look bad. Your long-term security strategy, though, depends on solid business cases supporting sensible purchasing decisions that will actively help the company and its long-term goals. Anything else is a distraction and can drain the company’s resources.

Ask your vendors to explain what you have in your services inventory

Why would you ask your vendors what they have sold you? Surely you know that already. Probably not, actually, and it is down to human nature as to why.

Purchases and contracts entered into may have supported failed initiatives or even not been appropriately implemented at all. This so-called “shelfware” is an issue in many companies, supported by 451 Research in 2014 (https://www.rsaconference.com/writable/presentations/file_upload/mash-t07a-security-shelfware-which-products-gathering-dust-and-why.pdf), with an evident rise in the problem when it comes to larger organisations. Asking your vendors for a catalogue of services will reap more accurate results as they have a vested interest in maintaining correct records as they charge you for their services (even if you use them or not). Any vendor worth dealing with will happily sit down with you and discuss what they have sold you and what value it brings. If they don’t, alarm bells should be ringing!

Armed with this information, you can start to build a picture of technology services in the company and ascertain what is shelfware, what is used effectively, and what isn’t. At this point, and no earlier, should the old purchasing go live again, minus the services that provide little to no value to the company.

These basics will be challenging because you will be pushing against the weight of expectations from other people in the company or because it takes time and effort. That doesn’t mean that they shouldn’t be done, and in doing so, they will help set you up for the following three sets of basics that we will cover in the next blog. If you can’t wait until then, here is a little teaser:

  1. Don’t say no to everything
  2. Stop testing your perimeter
  3. Building your plan

Are you sufficiently intrigued?

Links to other interesting stuff on the web (affiliate links)
How the Dark web is Embracing ChatGPT and Generative AI
How To Upskill Your Cybersecurity Team
A Trip to the Dark Side of ChatGPT

Too Much of a Good Thing

The one thing the current lockdown has taught me is that you really can eat too much chocolate… who knew?

Left to my own devices and without the distraction of a routine, regular work and people observing my unhealthy eating habits, my faulty brain tells me that more chocolate can only be a good thing and that I should continue to eat it until physical discomfort forces me to stop (in spite of my brain’s protestations.). It is an obsessive and compulsive behaviour that I recognise in myself, and do my best to contain, but it is a constant struggle arguing with myself that chocolate is not the most important thing in my life.

The same could be said to be true of many security professionals and their desire to roll out security practises to their organisations, implementing new procedures, standards, policies and ways of working that are designed to make the organisation very secure. They do this despite the protestations of the organisation itself telling them they have had enough, the new ways of working are too restrictive, difficult to follow and ultimately leave them with a security stomach ache.

This weeks Lost CISO episode talks about when too much security, like chocolate, is a bad thing.

This compulsion to think that security is the most important part of a business’ life is one that leads to users having security headaches all day and the business itself feeling slovenly, bloated and sluggish. (OK, that’s enough of the analogies.)

It is ultimately self-defeating, as users will do their best to work around draconian working practices, and the perception of a security organisation will be one of business prevention than vital service. I, and many others, have spoken about not being the department of “no”, but it goes well beyond just saying “yes”.

Agreeing to everything without thought of the consequences is potentially even more dangerous than saying no, especially in the short term. The vital distinction that needs to be made is that of a two way conversation between security and the end users and business. Finding out what is trying to be achieved is far more valuable than just focusing on what is being asked. Requests can be addressed in many different ways, not just by punching a whole in the firewall or switching off 2FA on the VPN, for instance.

In fact, this very conversation helps create even stronger relationships as it highlights two things:

  1. How seriously you take their request.
  2. How much you care about the organisation you both work for.

A great example of this in the above video is that of companies relaxing their security stance during the remote working ramp up of the lockdown. If the response was simply “no”, or even a straight “yes” with no consequences there would have been issues sooner or later. Working with the business, relaxing the standards for the initial growth and then methodically scaling and tightening the security once the initial growth is over is absolutely the right way to go.

So next time you feel yourself reaching for the chocolate wanting to say “no”, think beyond the the immediate consequences and how you can use security for the long term betterment of your organisation rather than your simple security stats.

And one bar of chocolate/security is always enough for everyone, right?

Do you need two re-align your security team to your business and don’t know where to start? (TL)2 Security has a proven track record helping security leaders and teams creat strtaegies and business plans that make real, competitive, differences to organisations. Contact (TL)2 to find out more.