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The Adversarial Mindset: Embracing a Proactive Approach to Security – or Staying Left of Bang

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Reacting to threats when they happen is easy. Pre-empting a threat and defending against it before it even occurs, when it’s just one potential threat that may or may not occur – that’s hard. It’s also your best chance at staying secure, minimising damage from security incidents, and in some cases, preventing security incidents from occurring entirely.

The Adversarial Mindset: Embracing a Proactive Approach to Security – or Staying Left of Bang | Sekuro

Understanding the concept of staying “Left of Bang”, outlined in the highly-recommended book of the same name¹, is vital to good security. To understand this concept – imagine a timeline of events – and at some specific point on this timeline, an attack takes place. That is the point where the bang occurs, and everyone starts reacting to the attack. Everything prior to that point, to the attack occurring, is considered left of bang. That’s where we want to be, and that’s where we want to do our best work. Once something goes ‘bang’, damage occurs, sometimes irrevocably so. We’ll be caught off guard, trying desperately to react and prevent further harm. It is much better to identify our threats and stop them before they ever reach this point.

1: “Left of Bang” by Patrick Van Horne and Jason A. Riley is a great book that should be recommended reading for everyone in the security industry.

The Adversarial Mindset: Embracing a Proactive Approach to Security – or Staying Left of Bang | Sekuro

Understanding the concept of staying “Left of Bang”, outlined in the highly-recommended book of the same name, is vital to good security. To understand this concept – imagine a timeline of events – and at some specific point on this timeline, an attack takes place. That is the point where the bang occurs, and everyone starts reacting to the attack. Everything prior to that point, to the attack occurring, is considered left of bang. That’s where we want to be, and that’s where we want to do our best work. Once something goes ‘bang’, damage occurs, sometimes irrevocably so. We’ll be caught off guard, trying desperately to react and prevent further harm. It is much better to identify our threats and stop them before they ever reach this point.

This principle of proactive security applies across the board, whether you’re protecting your organisation from a cyber-attack, a terrorist attack, or simply from someone breaking and entering secure facilities.

Responding reactively to an attack, no matter how good a team is, will always have consequences. Whether it’s something catastrophic like lives lost, more palpable like operational downtime, data loss, reputational damage, or simply the time-cost of incident response – there is a cost. 

“Put yourself in the shoes of the attacker, and answer this – how would you compromise yourself?”

Rather than waiting to detect an attack as it occurs, work to proactively identify it, and address your potential threats before they happen, not after. Search for suspicious activity that might predate an attack. Even earlier, work to identify potential attack pathways that exist towards your organisation. Identify, if you yourself were an adversary, what services would you target? How would you do this? As we’ve discussed before, put yourself in the shoes of the attacker, and answer this – how would you compromise yourself?

So, what are some concrete steps we can proactively take to protect ourselves?

1. Start by considering the adversarial perspective

  • How would you attack yourself?
  • What weaknesses exist in your system?
  • What attack path would you choose to get around your security measures?

As part of this, regularly conduct adversarial activities – consider table-tops, red teams, and other similar simulations. Don’t limit yourself to a specific scope or set of rules – your adversary won’t, so you shouldn’t either.

2. Establish a baseline, and look for anything that deviates

Both short and long term deviations might indicate attempts to compromise your systems. Train your security personnel and staff to do this, and develop a good procedure for reporting and addressing these concerns.

  • Is the man waiting in your lobby staying much longer than most people?
  • Is the woman waiting for a tram outside your office showing signs of being nervous, and not actually getting on a tram?
  • Or have you suddenly seen an increase in phishing emails over the last month?

3. Know what potential intrusions into your system look like

  • Understand what behaviour is normal for your users and understand what behaviour is normal for a potential attacker. Finance users don’t poke around in IT shares (which they shouldn’t have access to anyway!) – but attackers definitely do.
  • Make sure your attackers can’t hide in what would be standard behaviour elsewhere, but is an anomaly for you. If nobody at your company ever uses a remote desktop, seeing it in the network should be a red flag, and bears investigation.

4. Understand your potential attack surface from the perspective of your adversary

Determine every avenue, no matter how creative, an attacker might use to compromise you – is it physical entry to your building through the loading dock? Social engineering of an accountant, resulting in the installation of malware? Or compromise of that exposed service missing a key security patch?

1. Start by considering the adversarial perspective

  • How would you attack yourself?
  • What weaknesses exist in your system?
  • What attack path would you choose to get around your security measures?

As part of this, regularly conduct adversarial activities – consider table-tops, red teams, and other similar simulations. Don’t limit yourself to a specific scope or set of rules – your adversary won’t, so you shouldn’t either.

2. Establish a baseline, and look for anything that deviates

Both short and long term deviations might indicate attempts to compromise your systems. Train your security personnel and staff to do this, and develop a good procedure for reporting and addressing these concerns.

  • Is the man waiting in your lobby staying much longer than most people?
  • Is the woman waiting for a tram outside your office showing signs of being nervous, and not actually getting on a tram?
  • Or have you suddenly seen an increase in phishing emails over the last month?

3. Know what potential intrusions into your system look like

  • Understand what behaviour is normal for your users and understand what behaviour is normal for a potential attacker. Finance users don’t poke around in IT shares (which they shouldn’t have access to anyway!) – but attackers definitely do.
  • Make sure your attackers can’t hide in what would be standard behaviour elsewhere, but is an anomaly for you. If nobody at your company ever uses a remote desktop, seeing it in the network should be a red flag, and bears investigation.

4. Understand your potential attack surface from the perspective of your adversary

Determine every avenue, no matter how creative, an attacker might use to compromise you – is it physical entry to your building through the loading dock? Social engineering of an accountant, resulting in the installation of malware? Or compromise of that exposed service missing a key security patch?

Once you’ve got all this information put together, incorporate this into your security strategy. If you identify some weaknesses you’re not protecting, prioritise addressing these. If you notice a suspicious person hanging out in your lobby, go have a chat with them. If you think your staff are vulnerable to social engineering, arrange some security training.

In this way, you’re getting ahead of the curve – you’re not waiting for someone to call security about a guy they found ‘lost’, walking around the building – instead you’re making sure the perpetually open side door is locked, and our attacker is forced to go through the reception area instead. 

"The most important aspect that underpins all these ideas – is engaging in the adversarial mindset, understanding how you might be targeted, and acting on that information to increase security before the attack – not after."

Taking the Next Step

The Adversarial Mindset: Embracing a Proactive Approach to Security – or Staying Left of Bang | Sekuro
Red team everything

If you’re looking to embrace a proactive approach to security, start by integrating adversarial simulation activities into your strategy.

  • Conduct your own adversarial review of your security posture, of any new solutions, new processes, and plans. Red team yourselves. Red team your plans. Red team everything. Consider red team exercises and tabletop simulations, to validate your system works, and identify potential weaknesses you’re yet to discover.
  • Embrace a culture of security awareness. Encourage everyone to think proactively about potential threats and continuously seek ways to improve your security measures.

In the world of security, staying ahead of potential threats is far more effective than reacting to them. Adopting a proactive approach to security is your best chance at staying secure.

The Adversarial Mindset: Embracing a Proactive Approach to Security – or Staying Left of Bang | Sekuro
Red team everything

If you’re looking to embrace a proactive approach to security, start by integrating adversarial simulation activities into your strategy.

  • Conduct your own adversarial review of your security posture, of any new solutions, new processes, and plans. Red team yourselves. Red team your plans. Red team everything. Consider red team exercises and tabletop simulations, to validate your system works, and identify potential weaknesses you’re yet to discover.
  • Embrace a culture of security awareness. Encourage everyone to think proactively about potential threats and continuously seek ways to improve your security measures.

In the world of security, staying ahead of potential threats is far more effective than reacting to them. Adopting a proactive approach to security is your best chance at staying secure.

The Adversarial Mindset: Embracing a Proactive Approach to Security – or Staying Left of Bang | Sekuro
Red team everything

If you’re looking to embrace a proactive approach to security, start by integrating adversarial simulation activities into your strategy.

  • Conduct your own adversarial review of your security posture, of any new solutions, new processes, and plans. Red team yourselves. Red team your plans. Red team everything. Consider red team exercises and tabletop simulations, to validate your system works, and identify potential weaknesses you’re yet to discover.
  • Embrace a culture of security awareness. Encourage everyone to think proactively about potential threats and continuously seek ways to improve your security measures.

In the world of security, staying ahead of potential threats is far more effective than reacting to them. Adopting a proactive approach to security is your best chance at staying secure.

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    Aidan Tudehope

    Co-Founder of Macquarie Technology

    Aidan Tudehope, Co-Founder of Macquarie Technology

    Aidan is co-founder of Macquarie Telecom and has been a director since 1992. He is the Managing Director of Macquarie Government & Hosting Group with a focus on business growth, cyber security and customer satisfaction. 

    Aidan has been responsible for the strategy and execution of the investment in Intellicentre 4 & 5 Bunkers, Macquarie Government’s own purpose-built Canberra data centre campus. This facility is leveraged to deliver Secure Cloud Services and Secure Internet Gateway.

    With a unique pan-government view on the cyber security landscape, we are invested in leading the contribution from the Australian industry on all matters Cyber policy related.

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    CISO, Insignia Financial

    James Ng, CISO, Insignia Financial

    James is a leader with a range of experience across various cyber security, technology risk and audit domains, bringing a global lens across a diverse background in financial services, telecommunications, entertainment, consulting and FMCG (Fast Moving Consumer Goods). He is currently the General Manager – Cyber Security at Insignia Financial and most recently was at AARNet (Australia’s Academic and Research Network) where he oversaw a managed Security Operations Centre (SOC) capability for Australian universities. Prior to this James was the acting Chief Information Security Officer for Belong and led the cyber governance and risk team at Telstra.

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    CEO, Sekuro

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    Her work extends to “Cyber Mayday and the Day After,” a roadmap for navigating crises by mining the wisdom of C-level executives from around the globe. It’s filled with interviews with managers and leaders who’ve braved the crucible and lived to tell the tale. Her most recent book, “Building a Cyber Resilience: A Cyber Handbook for Executives and Boards,” was featured on Forbes Australia’s top list of books for CEOs. 

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    David Gee, CIO, CISO, NED, Board Advisor & Author

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    He is a seasoned technology executive with significant experience and has over 25 years’ experience in CIO and CISO roles across different industries and countries. At Macquarie Group David served as Global Head Technology, Cyber and Data Risk. Previously was CISO for HSBC Asia Pacific. His career as a CIO spans across multiple industries and geographies including – Metlife, Eli Lilly and Credit Union Australia. He was winner CIO of the Year 2014, at CUA where he successfully completed a significant Transformation of Core Banking, Online and Mobile Banking systems.

    David is past Chairman for the FS-ISAC Strategy Committee and awarded Global Leaders Award in 2023 for his contributions to the cyber security industry. A regular conference keynote speaker and 150+ published articles for CIO Australia, Computerworld, iTnews and CSO (Cyber Security), David now writes for Foundry CIO.com and AICD.

    His most recent book – the Aspiring CIO & CISO was published in June 2024 and David is writing his second – A Day in the Life of a CISO with a number of CISOs from around the world for 2025.

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    Naomi Simson, Co-founder, Big Red Group

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    Naomi had a corporate career with Apple, KPMG, IBM and Ansett Australia prior to becoming an entrepreneur. She is a prolific blogger, podcaster and business commentator, and appeared as the #RedShark in four seasons of Shark Tank Australia and she appears regularly on ABC The Drum. She is a non-executive director at Big Red Group, Australian Payments Plus, Colonial First State and Weebit Nano, as well as the Cerebral Palsy Research Foundation and the University of Melbourne Business and Economics Faculty.

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    For 25 years Naomi has been bringing people together whether it’s with her business experience, her speaking or writing. She is a strong advocate of business owners.

    Known as an entrepreneur and business leader; following the growth of RedBalloon which she founded in 2001, Naomi co-founded the Big Red Group (BRG) in 2017.

    Naomi had a corporate career with Apple, KPMG, IBM and Ansett Australia prior to becoming an entrepreneur. She is a prolific blogger, podcaster and business commentator, and appeared as the #RedShark in four seasons of Shark Tank Australia. She is a non-executive director at Big Red Group, Australian Payments Plus, Colonial First State and Weebit Nano. As well as the Cerebral Palsy Research Foundation and the University of Melbourne Business and Economics Faculty.

    A true business leader and influencer, with more than 2.7 million LinkedIn followers, Naomi is Australia’s most followed person on the business networking platform. She has authored two best-selling books Live What You Love, and Ready to Soar, and is an engaging, humorous and insightful speaker. She has four seasons of her Podcast – Handpicked.

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