That Bookkeeper

I have worked as an independent bookkeeper since 2004. That Bookkeeper offers excellent small business bookkeeping, consulting, and support.

Owner

Scott's Music

Bookkeeper from 2005-2009.
Purchasing Manager from 2008-2009.
General Manager 2009.

General Manager, Purchasing Manager, Bookkeeper

The Recycle Bin

Bookkeeper, Office Manager

Your New Bookkeeper | Saving 🇨🇦 & 🇺🇸 Owners Time & Stress | Fully remote bookkeeping for solopreneurs & small teams

If you’re reading my About section, you’re likely 1 of 3 people. 

1. A business owner
2. A bookkeeper

3. You’re just trying to figure out if I’m the Eric Matthews 
you remember from school, work, jail, etc. 
Short answer: I’m probably not. 

If you run a business, here are a few ways I can help. 

DIY, DWY, DFY

DIY (do it yourself): 

If you want to do your own bookkeeping, I get it. 

Every owner should know their numbers. 
Doing the work gives you a deep understanding on how your business runs. 
If/when you decide to outsource the work, you’ll know what to look for 
and you’ll be able to understand the monthly financial reports.

If that’s you, I recommend following me. 
I share content that will help you understand 
what to look for in your numbers, and tips on running a more efficient business. 

DWY (do it with you): 

If you’re not looking for a bookkeeper but just need some advice, 
I recommend connecting with me. 

Send me a message and let me know what you’re struggling with, like: 

- how to set up your software
- what to look for in your reports
- how to improve cash flow

I can answer most questions right in the messages. 
For bigger topics, we can set up a consulting call.

DFY (do it for you): 

If it’s time to outsource your bookkeeping, 
we can book a call and find out if I’d be a good fit. 
Not all bookkeepers are created equal, and only certain ones 
will be suited for your business and your needs. 
The important thing is finding one right for you. 

If you’re a bookkeeper, here’s how I can help. 

Please consider following me. 
I write content that most bookkeepers can relate to.
It’s not all about bookkeeping tips. There are plenty of places to find that. 

My goal is to give you tips on running a practice. 
How to deal with the pressure of running one by yourself, 
and some advice on doing it in an efficient way without burning out. 

If you’d like to get a deeper dive each week, you’d like my newsletter. 
It comes out every Monday morning, and it provides more advice 
than you can easily fit into a LinkedIn post. 

And, if you ever have questions that I haven’t covered, please connect with me. 
Send me a message. 
I’m always happy to help a fellow bookkeeper. 
In most cases, I can give you a quick answer in the messages. 
If your question needs a bit more time, we can book a consulting call. 
On a call, you’ll be able to explain your question in detail, and we can work together to find an answer. Or, if you just want to spend some time venting about a client, 
we can do that too.

Eric Matthews

Lester Chng

Cyber CEOs Brand Strategist. I build your brand as you build your business. | Senior Cybersecurity Advisor | Author | Naval Officer | CISSP | 🇨🇦🇸🇬 |

You head a leading cybersecurity firm.
But your online presence doesn't reflect it.

In fact, being invisible is damaging. 

You understand the power of thought leadership.
You know LinkedIn shapes deal flow and adds credibility in the industry.
You just don’t have the cycles (or the copy) to share your expertise and experience.

You have stories worth telling.

The insights from being in the trenches.
The deep conversations with your ace teams.
The hard discussions with your clients. 

Don’t let this wisdom go to waste.

That’s where I come in.

--------------------------------------------------------------------------------------------

How we work together.

Profile & Positioning
=> Rebuild your LinkedIn profile so visitors see industry authority, not “another vendor.”

Content engine
=> Ghostwritten posts that leverage your insights and expertise into engaging LinkedIn posts. 

Outreach campaign
=> Targeted DM campaigns and audience-building strategies that build your authority and land you on podcasts and conference stages.

--------------------------------------------------------------------------------------------

You focus on growing your firm and protecting your clients.
And we will ensure the industry, clients, prospects, and investors can’t ignore it.

Let’s build the personal brand that commands the cybersecurity conversation and drives business.


Worked with global client portfolio 
- MSPs
- MSSPs
- Agentic AI SOC
- AI-powered GRC 
- Operational Resilience 

Senior Advisor, Financial Crimes Unit Exercises. BMO Fusion Centre

Execution of Financial Crimes Unit Exercise and Drill Program
• Design and execution of exercises and drills to operationalize the Financial Crimes Unit Fusion Centre
• Scenario creation and exercise execution for Information Security, Enterprise Fraud Management, Physical Security, and Global Crisis and Continuity Management teams 
• Providing effective challenge of incident response readiness through exercise observation
• Execution of enterprise-wide Purple Team Exercise


Cybersecurity Exercises: Purple Team, Ransomware, DDoS, Malware, Data Corruption, Data Breach, 3rd Party Incidents
Fraud Exercises: ATOs, Attack on Payment systems, Business Email Compromise, PII Breach
Physical Security Exercise: Active Assailant, Civil Unrest, Bomb Threats
Crisis Exercises: Disaster Recovery, Business Continuity, Operational Resilience, Fire Incidents, Natural Disasters, Utilities Disruption

We landed in Canada 8 years ago. 
Today I still get this question. 
Why did you move from Singapore?

I always answer with this as if one of the reason. 

“We were very comfortable and had stable jobs. In fact, I know almost exactly how many career will pan out”

And we wanted to try something diff. 

This is what it wld have looked like:
- stayed on in the Navy
- promotions to LTC or SLTC
- 300k salary (don’t quote me)
- waiting on a ~500k bonus in 2026
- complete command of 2-3 warships

This is the last 8 years instead:
- ~50% pay cut for first role
- took 3 role changes to gain parity 
- only to be laid off after a few years
- and living through a dead economy

If we take a snapshot view here, it is a disastrous decision. 

But of course it’s never that linear. 

Here are other things that I gained:
- explored 2 career paths. PM + cyber
- grew professional network from 0
- gained experience in enterprises
- sold digital products & services
- found mission driven role + team
- resilience and independence
 
The questions will always be asked. 

And the journey is still being written. 

P.S what questions do u always get when you tell your story?
How do u answer them?

No alternative text description for this image

You are all busy. I don't expect you to read my history, so here is a little about me.

𝗕𝗼𝗿𝗻 𝗮𝗻𝗱 𝗿𝗮𝗶𝘀𝗲𝗱 𝗶𝗻 𝗦𝗶𝗻𝗴𝗮𝗽𝗼𝗿𝗲.

Never the model student.
Made a career choice at 19.
To serve in the Navy and see the world.

𝗖𝗮𝗿𝗲𝗲𝗿 𝗶𝗻 𝘁𝗵𝗲 𝗡𝗮𝘃𝘆

Daily lessons of leadership, critical thinking.
Ran the wargaming and simulation centre.
Left in 2017 after rejecting a promotion and the opportunity to command a ship.

𝗢'𝗖𝗮𝗻𝗮𝗱𝗮

Moved to Canada w no corporate exp
Struggled for years to climb a ladder
Fortunate to move into cybersecurity

𝗖𝘆𝗯𝗲𝗿𝘀𝗲𝗰𝘂𝗿𝗶𝘁𝘆

Currently in my 3rd role in cyber.
1. Project Management
2. Senior advisor - security exercises
3. Senior advisor - security exercises

𝗖𝘂𝗿𝗿𝗲𝗻𝘁 𝗲𝗻𝗱𝗲𝗮𝘃𝗼𝗿𝘀

Full-time at Rogers Cybersecure Catalyst, Toronto Metropolitan University. 
Best place I have worked in Canada.

Need cybersecurity tabletop exercises, cyber range training, cyber advisory services?

Give me a shout.

𝗖𝗼𝗻𝗰𝘂𝗿𝗿𝗲𝗻𝘁 𝗮𝗰𝘁𝗶𝘃𝗶𝘁𝗶𝗲𝘀

Book author
The Essential Cybersecurity Ex Playbook.
I still refer to it when I design exercises. 
Get it if you are tasked to run exercises.

Ghostwriter for Cyber CEOs and Founders
Your LinkedIn Account is a goldmine.
Build your thought leadership and authority.
I write your LinkedIn posts for you.

P.S What did you not know abt me?

How to create a content calendar in 10 mins and never worry abt what to post. 
 
Follow this process and save time. 
 
I never worry about what to post about. 
Not because I have a constant stream of inspiration and the words flow naturally. 
 
Writing and posting on LinkedIn has become part of my professional portfolio and I constructed a simple system. 
 
1. Decide what your objectives are 
- to establish thought leadership 
- to build stronger professional relations 
- to bring awareness to brand and product 
 
=> The clearer this is, the easier it gets. 
 
2. Decide how frequent you post 
- minimum twice a week 
- thrice is good 
- seven if able 
 
=> Schedule your time to write. 
 
3. Decide what are your content pillars 
- keep it no more than 2-3 
- for me it is ghostwriting 
- and cyber exercises 
 
=> What you want to be known for? 
 
4. Decide the various themes 
- posts that builds awareness 
- posts that builds authority 
- posts that builds trust 
 
=> How do u get ppl to like, trust, know u? 
 
5. Decide the theme for the day 
- Mon = Awareness 
- Wed = Authority 
- Fri = Trust 
 
=> Saves your time thinking of the theme 
 
6. Mind-map and research abt topics 
- Content should be planned 
- Mind-map your experience 
- Answer yr client qns 
 
=> If it is not planned, u will struggle  
 
7. Keep it simple and you will follow 
- create a simple system 
- don't complicate it 
 
=> It takes some prep but well worth it 
 
I planned out my content calendar and stick to it for at least 6 months. 
 
Struggling with posting consistently? 
Chances are you are winging it. 
 
Do you also leave yr business to chance? 
Didn't think so. 
 
It's time to take action. 
Get in touch. Start being intentional.

Getting into Cyber feels like winning the lottery.

Here’s how to increase your odds.

I interviewed my friend Zinet Kemal, who is an immigrant, mother of four, author, TEDx speaker & Cybersecurity professional. She is passionate about educating and empowering children on online safety and cybersecurity careers.

Journey & Motivation

Q1: You started in law before moving into cybersecurity. What inspired that switch?

I wanted a career where I could make a tangible impact and continuously learn. Cybersecurity offered that blend of purpose, challenge, and growth that instantly drew me in.

Q2: Hands-on experiences like competitions helped launch your career — what advice would you give to others trying to break into cyber?

Don’t wait to feel “ready.” Jump in, join competitions, try extra curricular stuff and learn by doing. Real-world practice builds confidence faster than any certification alone.

Cloud Security Expertise

Q3: What’s one common mistake organizations make when moving to the cloud?

Rushing migration without embedding security from the start. Security shouldn’t be an afterthought. It should guide every design and decision.

Q4: How do you balance speed and security in fast-paced cloud environments?

By automating what you can and baking security into the pipeline. That way, teams can move fast and stay secure without friction.
_____________________________

If you enjoyed this interview series, please follow Zinet. She frequently shares about her cybersecurity journey and is a gem to the industry.


P.S Have you seen her award list!

Cyber CEOs are missing one of the biggest opportunities on LinkedIn.

Your founder story.

Not the pitch.
Not the product.
The reason you started.

Here is why it matters.

1. It builds trust faster than yr website.

People want to know the conviction behind your company. Your story answers the core question every buyer has: why should I trust you.

2. It humanizes your brand.

Cybersecurity is technical and crowded. Your story cuts through the noise and shows the person behind the mission.

3. It creates instant differentiation.

Competitors can copy language, pricing, and positioning. They cannot copy your journey.

4. It strengthens every future conversation.

When people understand your why, your product demonstrations, sales calls, and partnerships become warmer and easier.

Your founder story is not optional.
It is a strategic asset.

If you do not tell it, your audience will never hear it. And don’t wait for permission to share too. 

No one is gonna give you that.

“I’ll take a break from writing/posting”. 

That’s what I told myself as I returned from my vacation. 

“It will be easy to get back into it”. 

Just like my exercise routine, my writing and networking rhythm were severly derailed. 

Even though my systems and tools were in place, I need to reconvince myself of the intend of being active on this platform. 

And it really does fall back to the why. 

Once that is reaffirmed, then the other pieces of the how kicks back in. 

Here’s back to sharing:
- how organizations should use cyber exercises to improve their readiness and resilience 
- how cyber CEOs should use LinkedIn to drive brand awareness 

P.S who thinks the LinkedIn feed is darn boring these days. Let’s start sharpening our storytelling skills.

It seems like privacy is a premium these days.

And it can be sidelined if we don’t preserve it.

AI models feed on data. And yet so many organizations have headed straight for the AI gravy train without due consideration for the impact on data management and privacy. 

I interviewed my friend Patrick Lo, the CEO of Privacy Horizon, who helps his clients make sense of the ever-changing landscape of privacy and the impact of AI.

The Future of Privacy Leadership

Q7: What qualities will define the next generation of privacy leaders in healthcare?

Future privacy leaders will combine a strong understanding of technology, turning intricate risks related to AI, data, and cybersecurity into transparent, human-focused governance approaches that build trust among stakeholders.

Q8: If you could change one thing about how organizations approach privacy today, what would it be and why?

I would change the perspective from viewing “privacy as compliance” to seeing “privacy as strategy.” Privacy doesn’t have to be a boat anchor. Privacy is about common sense. Privacy is nothing more than good information management and good customer service. When organizations integrate privacy with trust, innovation, and brand value, compliance occurs naturally and a culture of accountability becomes self-sustaining.

_____________________________

If you enjoyed this interview series, please follow Patrick. He is a healthcare privacy expert and has helped organizations build privacy and security programs.


P.S Is privacy a top concern when implementing AI?

Cybersecurity professionals struggle in OT organizations.

Especially if they don’t take the time to understand operations.

I interviewed my friend Osman Saleem, the Managing Director of Actimeta, who helps his clients secure their OT and IoT infrastructure.

What Makes OT/IoT Security Complex

Q3: What makes protecting operational environments fundamentally different from traditional IT cybersecurity?

OT environments have physical processes, so organizations prioritize safety, reliability, and availability of OT systems. Confidentiality of data takes a back seat. Additionally, OT systems have a much longer life cycle. As a result, these systems operate 24/7 on legacy equipment and networks making patching and rebooting a challenge. Security changes can directly impact physical processes, which means risk management must balance cyber controls with operational continuity.

Q4: Can you share an example of how operational and security priorities sometimes conflict — and how organizations can bridge that gap?

Security teams may recommend immediate patching or network changes, while operations teams push back due to downtime risks or safety concerns. Capital upgrades of legacy equipment are also cited as reasons for avoiding immediate patches. Bridging that gap comes from joint risk assessments, staged mitigation plans, or designing controls that reduce risk without disrupting critical operations
_____________________________

If you enjoyed this interview series, please follow Osman. He is a security infrastructure expert and has helped organizations build IoT and OT security programs.


P.S. What’s the biggest challenge in OT security?

Data is absolutely vital for effective healthcare.

But how do we manage the risk and liability?

Managing data and addressing privacy issues are major risk areas for many healthcare organizations. Add AI to that picture and it can be messy very quickly.

I interviewed my friend Patrick Lo, the CEO of Privacy Horizon, who helps his clients make sense of the ever-changing landscape of privacy and the impact of AI.

The Evolution of Privacy in the Health Sector

Q1: You’ve worked across both government and private healthcare environments. How has the concept of “privacy by design” evolved in the health sector over the past decade?

In the last ten years, privacy by design has evolved from a compliance trend to a core design principle integrated into digital health innovations and an operational imperative. It’s now focused on instilling trust and resilience in systems rather than merely fulfilling regulatory requirements.


Q2: What are some persistent privacy misconceptions you still encounter among healthcare organizations today?

A common misconception is that privacy is the same as security or that having a lawyer create an agreement and terms of use ensures protection and compliance. Effective privacy management requires ongoing governance that aligns people, processes, and technologies to foster accountability and manage data throughout its lifecycle.
_____________________________

If you enjoyed this interview series, please follow Patrick. He is a healthcare privacy expert and has helped organizations build privacy and security programs.


P.S. What other privacy mistakes do you see healthcare organizations make?

Privacy mgmt shouldn't be an afterthought.

Yet many choose to only address it later.

That is a risk startups should address early in their journey, especially if they handle sensitive information. Add AI to that picture and it can be messy very quickly.

I interviewed my friend Patrick Lo, the CEO of Privacy Horizon, who helps his clients make sense of the ever-changing landscape of privacy and the impact of AI.

Operationalizing Privacy — From Compliance to Trust


Q3: Many healthcare startups treat privacy as a barrier to speed. How do you help founders operationalize privacy without slowing innovation?

I encourage them to view privacy as an enabler rather than an impediment. We help clients establish strong privacy foundations and clear growth plans. We offer Virtual Privacy Officer service to help them navigate privacy-related challenges and implement best practices, allowing them to concentrate on their core business. Embracing privacy can not only benefit their bottom line but also set them apart from the competition. Effective privacy management builds customer trust and differentiates them from competitors.


Q4: What frameworks or approaches have proven most effective in embedding privacy into day-to-day clinical or product operations?

The NIST Privacy Framework, ISO 27701, and the CSA Model Code for the Protection of Personal Information provide a solid foundation, but achieving success often requires creating and executing a well-organized privacy management program. This program should encompass an accountability framework, functional tools such as privacy impact assessments (PIAs) and risk registers, and training that ensures everyone is responsible for privacy, not just the compliance team.
_____________________________

If you enjoyed this interview series, please follow Patrick. He is a healthcare privacy expert and has helped organizations build privacy and security programs.


P.S What other privacy frameworks would you recommend?

Have you tried asking ChatGPT abt yourself?

Try it. I hope you don’t find sensitive information.

AI models feed on data. And yet so many organizations have headed straight for the AI gravy train without due consideration for the impact on data management and privacy. 

I interviewed my friend Patrick Lo, the CEO of Privacy Horizon, who helps his clients make sense of the ever-changing landscape of privacy and the impact of AI.

The Intersection of Privacy and AI

Q5: As AI becomes more embedded in diagnostics and digital health tools, where do you see the biggest privacy blind spots emerging?

Many organizations that adopt AI often overlook the importance of a solid AI Governance Framework. This oversight can lead to unsupervised AI being used within the organization, allowing users to leverage AI solutions without proper guidance. Such a lack of direction often leads to unintended disclosures of sensitive information. Additionally, a significant blind spot exists where many organizations are unaware of what personal or health data their AI models are accessing, retaining, or inferring. 


Q6: How is Privacy Horizon adapting its services — for instance, with AI-PIAs or automated privacy assessments — to address these new challenges?

We’ve expanded our service model to include AI Privacy Impact Assessments, AI Governance Frameworks, AI Training, and readiness tools aligned with the EU AI Act and ISO 42001. These help healthcare organizations assess AI systems’ risks, ensure transparency, and demonstrate trustworthy AI adoption.
_____________________________

If you enjoyed this interview series, please follow Patrick. He is a healthcare privacy expert and has helped organizations build privacy and security programs.


P.S What worries you about AI and privacy?

Take a second to count your personal connected devices.

Now, estimate that number for an enterprise set-up.

Enterprises struggle to keep up with the inventory, tracking, management, and governance of their IT systems. Industries and companies that rely heavily on physical systems, such as monitoring devices, automated systems, and highly integrated systems, add layers of complexity and associated risks to maintaining operational efficiency and security.

I interviewed my friend Osman Saleem, the Managing Director of Actimeta, who helps his clients secure their OT and IoT infrastructure.

The OT/IoT Security Landscape 

Q1: How has the growing interconnection between physical systems and digital networks changed the way organizations think about cybersecurity?

Organizations that run physical systems and OT are more aware now of the risks that come with connecting them to digital networks. Asset owners are increasingly focused on securing these environments—marketing hype can amplify the fear, but the concern is justified. More connectivity expands the attack surface and links cyber incidents to real-world impacts on safety, reliability, and finances. As a result, there is a shift to treat cybersecurity as an operational responsibility, not just an IT issue.

Q2: From your experience, what are the biggest misconceptions business leaders still have about securing operational or connected environments?

Many business leaders place more emphasis on tooling and technology. Their main focus should be prioritized towards embedding cybersecurity practices and controls in their business workflows, organizational processes and ensuring their governance is not just documented, but functional. 
_____________________________

If you enjoyed this interview series, please follow Osman. He is a security infrastructure expert and has helped organizations build IoT and OT security programs.


P.S. What are some IoT/OT security assumptions that many have?

If growing your LinkedIn presence as a cyber CEO is not part of your 2026 plan, it is a huge marketing miss. 

The others parts are shaping up:
- website copy
- marketing swag
- cold email blasts
- conference booth
- CISO wine and dine 😃

All that is important and probably takes up the bulk of your budget. 

And then when your prospects land on your LinkedIn page, it blands (yes bland) in with the rest of the corporate copy. 

“We are on brand.”
“Our product speaks for itself.”

What could have been a differentiator from your competitors and a vibrant platform to build a community and awareness for your company. 

Instead, it just fades to the background. Like many of the other passive accounts. 

Is your LinkedIn account working your you, your company, and your vision?

Or will 2026 be another missed opportunity? 

Your platform. 
Your choice.

Cyber CEOs have endless stories. 

Here are some ideas if u r stuck.

1. The moment you realized the cybersecurity problem you’re solving was real (A client incident, a failure you witnessed, or a blind spot in the market.)

2. Why you decided to start the company instead of joining another one (Your conviction, frustration, or spark.)

3. The first obstacle you faced as a founder and what it taught you
 (Funding, product clarity, hiring, credibility.)

4. The early version of your solution and how different it was from today
 (Show evolution and persistence.)

5. A hard lesson you learned that shaped how you lead now
 (Trust, communication, resilience, decision speed.)

6. The turning point when you knew the company would work
 (First client, first renewal, first big validation.)

7. A belief you hold about cybersecurity that most people overlook
 (Your “why” behind your mission.)

8. How your background shaped the way you approach security problems
 (Past industries, roles, failures, or personal experiences.)

9. The sacrifice most people don’t see
 (Time, stability, opportunity cost, personal growth.)

10. Your vision for the industry and why you’re committed to it
(Where things are going and why you care.)

P.S Expand on each point in a few different angles and your content is set for months. 

Any other story ideas?

I consult with many Cyber CEOs. 

These 4 questions come up in every strategy call I run with founders.

⸻

1/ What should I post without oversharing or sounding salesy

They worry about balancing:
- Oversharing insights 
- Being authoritative vs promotional

But the real issue?

This isn’t a writing problem.
It’s a positioning + content strategy problem.

Once you define your POV and boundaries, posting becomes easy.

⸻

2/ Will this really generate business, or is it just vanity?

They’re skeptical because:
- Impressions ≠ pipeline
- “Likes” don’t close deals
- Decision-makers feel invisible on LI

Behind this question is a deeper fear:

“Will my effort pay off?”

LinkedIn is a trust engine, not a slot machine. It compounds if you show up consistently.

⸻

3/ How do I stand out when every cyber CEO sounds the same?

Their feed is full of:
- News reposts
- Corporate announcements 
- Zero Trust / AI buzzwords

Their real question is:

“What is MY unique point of view?”

The answer is always the same. 
Stand out by being specific, not louder.

Your niche, your observations, your client stories, your lessons.

Those are the differentiators.

⸻

4/ How much time does this take each week?

They assume LinkedIn is:
- Daily posting
- Daily commenting
- Constant DMing
- Full time social media diva

But what they actually want is simple:
A strategy that is intentional. 
A plan that drives results. 

You don’t need to post daily.
You need clarity, consistency, and relevance.

⸻

If you’ve have all these questions too, the good news is they’re all solvable.

Cyber CEOs don’t need more content.
They need a clearer strategy, stronger positioning, and a repeatable system.

P.S what other qns do u have?

10 planning considerations for a live red team exercise.

A live Red Team exercise can transform your organization’s cyber readiness.

Or it can blow up in your face.

Most companies underestimate the planning required. 
Live exercises introduce operational risk, reputational exposure, and real technical consequences if poorly scoped.

Here are 10 planning considerations. 

⸻

1. Define crystal-clear objectives before touching the scenario.

A Red Team exercise easily derails without a defined purpose.
•	Are you testing detection?
•	Decision-making?
•	Business response?

Knowing the objective helps guide the red team and enables alignment.  

⸻

2. Assess organizational maturity honestly before selecting tactics.

Live exercises should match capability.
Teams still struggling with escalation protocols shouldn’t jump straight to advanced APT emulation.
Ensure your IRP, SOC workflows, and communication playbooks are mature enough to withstand live pressure.

⸻

3. Secure executive sponsorship and socialization early.

Leadership must know what they’re approving. This includes scope, risks, expected disruptions, and reporting cadence.

⸻

4. Establish strict scope, boundaries, and rules of engagement.

A Red Team must know exactly what is allowed.
Examples:
•	No production data exfiltration.
•	No destructive actions.
•	Limited hours for intrusion.
•	Clear ‘stop game’ conditions.

Defined ROE protects your systems, your people, and your reputation.

⸻

5. Map out all critical systems, dependencies, and crown jewels.

You can’t test everything.
Choose what matters most:
•	Mission-critical applications
•	Identity systems
•	Cloud environments
•	OT/ICS (very rare)

Have a clear reason why this is the target. 

⸻

6. Involve key third-party vendors before game day.

Many Red Team exercises collapse due to vendor bottlenecks.

Notify them early. 

Their tools, logging, and escalation capabilities determine how realistic and valuable the exercise becomes.

⸻

7. Prepare the SOC and security teams without revealing the scenario.

Let them know the exercise window and who to clarify with if there are doubts. 

A Red Team exercise shouldn’t overly hamper operations. Yes there will be increased load for short periods of time. 

⸻

8. Decide the battle rhythm for decision-making and communication.

Synchronisation avoids chaos and ensures realism in response flow.

Also include exercise control meetings to keep teams updated. 

⸻

9. Create a safety plan.

Live operations = live risk.

A safety plan ensures the Red Team can push boundaries without endangering the business.

⸻

10. Design a mature debrief, learning review, and AAR process.

The biggest ROI comes after the exercise.

A rigorous debrief is where transformation happens.

⸻

Conclusion

A live Red Team exercise is a meticulously planned, high-stakes enterprise learning event.

Plan it properly, and you elevate your team’s resilience.
Rush it, and you erode trust in security

Here’s one signal to know yr cyber exercise is highly effective. 
And most TTXs never trigger this. 

We recently executed a cyber range simulation exercise that put an IT team through a stressful scenario. 

The team was actively analyzing the IOCs and raise many relevant points for decision making. The leadership team weighed the risks and make a decision for containment. 

This decision was communicated to the technical teams and it spark a behavior which I didn’t expect but was glad it happened. 

The IT team responded to seek clarification on the decision. The instructions from the leadership team was clear on intent but the IT teams wanted to ensure that the leadership team understood the risks and nuances of the decision. 

And the discussion got pretty heated. 

This is termed as “Challenge and Response” and is something that we used while we manage the navigation team to ensure the safety of the ship. 

Team members would challenge the instructions (not the authority) if they were unclear or they had information that may impact the decision. The officer of the watch will have to respond to confirm or clarify the order. 

The purpose of this mechanism was to ensure that there was an avenue for clarification of an order without the risk of insubordination. 


So to my surprise, I saw this playing out as we ran our exercise. 

This is a healthy sign that the team had the right culture and understood the intent of the team’s actions. 

How did the heated discussion end?

I had to intervene, acknowledge the perspectives of both parties, and park the issue aside to continue w the exercise. 

This learning point would not occur in a benign tabletop exercise. It took a realistic high pressure scenario to tease out the practical considerations of incident response. 

P.S can u guess what the discussion was about? 
I’ll give a prize if anyone guessed it!

taplio

The Battle

Eric Matthews

Lester Chng

Followers

Posts

Engagements

Likes

Performance ScoreLester Chng's LinkedIn Performance

Ready to grow your LinkedIn presence?

taplio

The Battle

Eric Matthews

Lester Chng

Followers

Posts

Engagements

Likes

Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Lester Chng's LinkedIn Performance

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Performance ScoreLester Chng's LinkedIn Performance