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I'm an operator documenting what I've learned building revenue engines over the past decade.

CEO @ MSP Sales Partners. Managing Partner @ Repeatable Revenue. Former PE-backed CEO. Former Managing Director at the U.S. Chamber of Commerce. Spent six years building sales systems for Robin Robins (TMT, sold to PE). Built revenue engines for 100+ service businesses.

I write about what I've learned: how sales systems actually scale, the difference between activity and productivity, why hard choices matter more than hard hours, building a business without burning out.

This isn't guru content. It's lessons from the work... what I got wrong, what finally clicked, patterns I see across businesses, frameworks that actually held up under pressure.

I write for three types of people: Strategists thinking about exits and scale. business owners stuck at a plateau trying to break through. Thinkers who want to build intentional lives, not just businesses.

If you're one of those (or all 3), follow along.

Ray J. Green

"I do have to tell you, Ray, there is a small chance of sudden death."

My cardiologist. 

About a year-and-half-ago following a chance diagnosis of hypertrophic cardiomyopathy (HCM). 

I initially reacted the way you'd expect. 

"WTF am I supposed to do with that?!?!"

And, "Why in the hell is this happening to me?"

After all, I do 2 hours of cardio a day. 

In fact, my last echocardiogram shows I have 'athlete's heart.' My heart has literally grown because I've exercised it so much--in a good way. 

So how do I end up with a heart condition? 

But I had it wrong. This wasn't happening TO me. 
It was happening FOR me. 

That reframe changed how I look at this. Even with a couple ER visits in recent weeks. (Which ended up perfectly fine and just more awareness.) 

And it's reframed how I see every hardship in general. 

I break it all down in 10 min podcast here: https://lnkd.in/e3FKQD-m

CEO @ MSP Sales Partners | Man. Partner @ Repeatable Revenue | Ex-PE Backed CEO | Former U.S. Chamber Man. Director

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6 years ago I started posting on LinkedIn because I actually enjoyed creating content. 

I also had a decent amount experience turning around sales teams & businesses using some unorthodox practices. 

So, I wrote about it. 

And wrote about leaving the C-Suite, moving my family to Cabo, and figuring out how to generate income from a Mexican beach. 

My wife and a couple friends were the only people who liked my posts. Sometimes not even them. 

But I actually enjoyed the process. And I wrote just about every day. It was easy. It was light. It was enjoyable. 

With just 3 or 4 likes per post (I don't have many friends), I even managed to get a couple clients from content. They saw a post, looked at my half-assed "optimized" profile, and hired me to give them advice. 

Shortly after that, creating content became a task. Something I had to do every day to be seen and known. To generate some business. 

Sit down. 
Think of something to write. 
Hammer out a post. 
Make it look pretty with descending lines. 
Post. 
Every day at the same time. 

It started to consume every morning. 

Then I learned that commenting on everyone else's posts helped my posts get more reach. So I'd block time every day to "engage" with people's content. A couple hours a day... on a slow day. 

Then I decided to start "batching" content, sitting down and hammering out 6 or 7 posts in one setting and scheduling them all out in advance. 

Then I started recycling content, taking old stuff, refreshing it, and adding it to a second publishing slot for the day. 

Before long, I was cranking out 21 posts a week and racking up who knows how many hours of commenting. 

For all intents and purposes, I was a machine. 

And that's before AI got added to the mix. 

But along the way, I stopped enjoying the process. 

I managed to systematize the joy out of writing. 

Content was forced. Engagement was forced. 

I wasn't sharing a viewpoint I felt strongly about. I wasn't enjoying the process. I was just "building an audience" and generating leads. 

And to some extent, that's perfectly fine. It's LinkedIn. We're all here to do business in one way or another. Myself included. We all gotta eat. 

But today I made a decision: I'm going to start spending more time doing things I genuinely love doing. And one of those things is writing for the sake of writing. 

Not for leads. Not to check a box. Not at a specific time. Not on a schedule. Not in conjunction with 7 hours of commenting on other people's posts. 

But for the joy of it. 

And hoping it adds value in one way or another to someone else here. Even if it's back to 3 or 4 likes per post. 

This post is the first stab at that. And I'm already enjoying this process a hell of a lot more. 

If you want to follow along, comment "WRITING" to receive my.... kidding. 

You'll never see another handraiser post like that from me again. But that's a post for anther day. Maybe tomorrow. But then again, maybe not. 

See you around.

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OCAS 2.0

It took me 40 months to break $40k/month as an independent consultant. If I started again, I'd do it in a fraction of the time. I created this course - and share it for FREE - to help others do exactly that: https://www.rayjgreen.com/digital-course

RJG Newsletter

Join my email list for practical advice on sales, strategy, and self-mastery from an operator, not a guru: https://rayjgreen.beehiiv.com 

Chief Executive Officer

Managing Partner

Writer & Podcaster 

Expert In Residence: Sales & Sales Management

When people say, “just stay consistent” or “it’s about volume,” what I hear is: work hard, cross your fingers, and hope you get lucky. 

Just read a post from a popular ghostwriter on how to go viral. His hack? Just have to keep posting. 

Over the weekend watched a YouTube video from a popular business guru on how to find the right growth strategy. Solution? You just have to keep trying new things until it works. 

But if you take this advice literally, and completely, you’re essentially saying “Just keep doing shit until you get lucky.”

And if you’re wired anything like me, that’s not going to fly. Not is it going to be sustainable. 

Volume does matter. Consistency does matter. 

But just like driving to the office everyday doesn’t train you to be an F1 race car driver, volume and consistency aren’t enough. 

It’s intentional volume. Combined with focused reflection and aggressive iteration. 

A critical mass of effort done on purpose. Then regularly reflected on to discern what’s working and what isn’t. And adjusting accordingly. 

Volume without intentionality and iteration is wasted energy. Or lottery ticket-type betting. 

And a good way to burn out.

The thing you're most certain about in your business is probably the exact thing keeping you capped.

Just took my kids to a Museum of Illusions in Utah. Your brain swears things are true that aren't—by design.

Same thing happens in business. 

I've spent a lot of time this past year with founders of $200M businesses. And founders of $2M businesses. 

Biggest difference between them? 

A few simple beliefs. 

I break down what this looks like in a 10 min podcast. 

Tune in to listen here: https://lnkd.in/eCpt5-i7

My inner critic is a loud SOB.

Good workout? 
You could've gone harder. 

Eating okay? 
Could be cleaner. 

Time with your kids? 
Could be more present. 

Productive at work? 
Could've done more.

It never stops.

I used to fight it. Try to quiet it. Tell myself that I should be easier on myself, like everyone says you should.

And you know what happened?

It made things worse.

Because then I had the critic AND a voice criticizing the critic. 

Layering noise on top of noise.

So I stopped fighting.

I realized my inner critic is a feature. Not a bug.

That voice... the one constantly pushing me... is what I credit for jumping literal generations for my family.

Growing up with divorce. Absent father. Broken homes. In a foster home at one point. Not a lot of money. Or formal education. And layers of other challenges. 

Today? Happily married. Two healthy boys who know nothing of that instability. MBA from a top school. Living in Cabo. Traveling the world.

That tough critic that pushed me said "This is not for you. You can do better. You will do better."

And I did.

Here's the nuance though.

I've learned to allow the critic to push my actions. My habits. My standards.

Without allowing it to define my worth.

I can accept that my actions will never be "enough" while also knowing that I am enough as a person.

And that's a big effing difference.

One keeps you sharp. 

The other keeps you whole.

Dropped a podcast expanding on this a bit if you're interested: https://lnkd.in/eAm7GyPn

Most salespeople treat discovery like a podcast interview.

"Tell me about your business. How many users? What's your current setup? Walk me through your IT history."

Like you're only there to gather information and collect facts.

And I promise you it's costing you deals. 

Something that's helped the hundreds of consultative sellers I've coached: 

Discovery isn't information gathering.
It's the first step of a strategic close. 

Run a bad discovery and the rest of the process is going to pay the price. 

Example for IT companies:

Bad discovery: "How many servers do you have?"

Good discovery: "How is IT accelerating your growth or holding it back right now?"

One gets you data. The other gets you business impact—the ammunition you need when you're actually trying to close the deal 3 weeks later.

The same thing happens in assessments.

Example for IT companies: 

You find cracked passwords. You find too many O365 admins. You document the vulnerabilities.

Then you present them like a checklist: "You have X problems."

But the MSPs who close? They explain why that matters: "You have cracked passwords on essential systems. Let me tell you what happened to a company last month when a disgruntled employee knew they were leaving…"

Every step in your process—from first call to final proposal—has one job: move the deal forward.

Not educate. Not inform. Not "let them think about it."

Move. The deal. Forward.

I shared a podcast on this, and why despite the stigma attached to it, it really is Always Be Closing. 

I explain why and how here: https://lnkd.in/e7SVFiVx

I wish there were more 'right' and 'wrong' calls in business. But what I've learned from 20 years of leading teams, divisions, and businesses? 

It's a lot more "good bet vs bad bet' and a lot less 'right decision vs wrong decision.' 

Regardless of whether you're running $500K business or a $500M business, when you're making high level decisions about where the business should go, you're operating with uncertainty. 

You may be 55% sure on some days. 90% sure on a good day. But that's the job description. 

The problem is, I see this crush a lot of founders. 

They go this direction. Then that direction, Start this project. Change to that project. Pick this priority. Then that priority. 

It's exhausting just to watch. 

Even more exhausting to do. I know from experience. 

I recorded a 10 min podcast for any founder or business leader that's felt overwhelmed by uncertainty. And anyone that's let that uncertainty lead to perpetual pivots and indecision. 

You can tun in here: https://lnkd.in/eVNUZDuY

One of the biggest challenges with digital marketing is remembering that the people in your feed aren’t the people buying your stuff. 

(Unless you sell products and services to online creators.) 

I’m guilty of forgetting this myself. 

I scroll here and see a bunch of people using AI in really cool, new ways. 

That gets baked into my head when creating a podcast or YouTube video on AI. 

Then I go to an event and talk to my actual customers and prospects and realize, they’re not using AI in their sales process in some of the simplest ways. 

But it’s not just with AI. It’s with all our messaging. 

We have what’s called “the curse of knowledge.” 

When we forget what it’s like to not know what we know so well. It’s a trap a lot of experts fall into. 

So, reminder (to myself as much as anyone) to spend a little more time creating for the people we want to listen. 

Not other creators.

Years ago I gave my wife terrible business advice.

Not because it didn't work.

But because it did.

She had a custom baby bedding business doing $25K/month on Etsy. Six-month waiting list. Countless 5-star reviews. People literally begging her to make "just one more."

She asked for my input.

I looked at all the indicators and told her what any business advisor would say: "It's time to scale."

She had some resistance. "Yeah, but I love sewing."

But she pushed on.

She hired people. Built systems. Went from spending her days doing what she loved—talking to customers, designing patterns, creating with her hands—to managing quality control and dealing with employee issues.

The advice worked. The business scaled.

And she fucking hated it.

Her initial resistance? That gut instinct she had?

Spot on.

She didn't want to build a business. She wanted to do the thing she loved and get paid well for it. Those are two completely different games.

My advice was biased by what I believed a business should be. Not what her business could be for her.

I see this happen quite a bit. And I'm more aware of it having gone through my wife's experience with her. 

I recorded a podcast breaking down: 

→ Why you should pick advisors carefully (even if you love them)
→ Why product-market pull doesn't mean you should scale
→ How to filter advice so you build the right thing (for you, not for them)

Listen in here: https://lnkd.in/eCtMPwpn

Our 4th graders were begging for cell phones. 

Parents made a pact: rewind the clock & meet 'em halfway. 

No smartphones... 

But they were genuinely thrilled to get these retro beauties instead. 📞✨

You know why so many salespeople waste 10 minutes talking about the weather?

Because they think being liked is the same as being trusted.

It's not.

Here's how I think about it:

If I needed brain surgery, I wouldn't pick the surgeon who makes great small talk.

I'd pick the one who asked questions that prove they've seen my exact condition 50 times before.

Likability gets you in the door. Credibility gets you the deal.

(If you are selling anything of high importance.) 

But there's the psychological trap a lot of reps fall into:

Small talk feels safer. It's comfortable. It doesn't require you to demonstrate expertise or challenge assumptions or risk saying something that might make the prospect uncomfortable.

So you hide behind it.

You talk about dogs and football teams instead of asking the question that might make them think: "Wait, maybe our current IT setup isn't as solid as we thought."

Real rapport is built on confidence, not comfort. 

Confidence that you know their industry. That you've done your homework. That you're not afraid to respectfully push back when they tell you something that's not accurate.

I recorded a podcast breaking down: 

→ Why people confuse likability with trust (and how to fix it)
→ The preparation work that builds real credibility
→ How to show up as an expert, not an order taker

Listen to the whole thing here: https://lnkd.in/eDs2mfSZ

There's a name for what happens in a business when leaders have no spine. 

You know what I'm talking about. When the people responsible for making the tough calls... just don't. 

They ignore underperformance. 
Avoid difficult conversations. 
Procrastinate making hard decisions. 
Or just never make them at all. 

From a business standpoint, it's called 'management debt.' 

'Management debt' compounds just like financial debt. 

It destroys cultures. And it can stunt growth just as much as irresponsible financial debt can. 

I recorded a quick podcast breaking down: 

→ What management debt is (vs. real leadership)

→ The compounding impact it has on companies 

→ How to keep it from accumulating in yours 

Tune in here: https://lnkd.in/eT3aBrt2

We all have beliefs that aren’t true. Every single one of us. 

The question is: How much are those beliefs holding us (or our business) back? 

Last week we took our beach kids on a ski trip to Utah for a few days. 

(“Dad, is that real SNOW?!?!) 

We had an unexpected delay in Salt Lake City and stopped by the Museum of Illusions—which is basically an hour and a half of mind bending experiences. 

It’s display after display of, “How in the hell is that happening?” 

And what it comes down to is your brain creates shortcuts with limited data. It stitches information together in a way that makes sense… but isn’t true. 

Like this picture. 

The tops of both of these boxes are the same size. Hard to see. But they even give you a block to hold over it to confirm. 

It’s harmless in this controlled environment. 

But what if the tops of these boxes represented a critical belief you held about something of importance that was holding you back. 

You know, the belief that: 

— “This business just doesn’t have the potential.”

— “That idea will never work.”

— “I’ve got to have [money, experience, connections, etc]  before I can do that.”

— “I’m too [young, old] to do this.” 

— “That channel doesn’t work anymore.” 

And what if it was just completely… wrong? 

An illusion that was holding you back from a monumental shift and achieving what you wanted. 

I've spent a lot of time this past year with entrepreneurs who've built $50M, $100M, $200M businesses.

I've also spent a lot of time with entrepreneurs who are struggling to get there. 

And the biggest difference I see is their belief systems. 

Founders who struggle to get to the next level typically have a belief that’s holding them back. Something they know to be true… that simply isn’t.  

A common one being that they are more essential to day-to-day operations than they really are. 

The question I’m asking myself today: What am I dead certain is true… that isn’t?

How about you?

I'm on Facebook the other day and see an ad: "Every sales expert is telling you the same lie—you need to build rapport before you sell."

The pitch? Buy my $37 course to learn how to sell without rapport.

If you read on, you'll see this supposed sales expert was making a common mistake: 

Confusing rapport with small talk. 

Rapport = trust & credibility. 

Small talk = likability. 

Talking about the weather. The local football team. The family pictures on the desk.

That might make you likable. But it doesn't make you credible.

And if you're selling anything of real importance to someone, likability only goes so far.

Think of it this way: If you need brain surgery, are you going with the doctor you like most, or the one you trust to get the job done? 

I recorded a podcast breaking down the common misconception. 

In it, I break down:

→ Why small talk doesn't equal rapport (and what does)

→ How to establish credibility in the first 5 minutes

→ The questions that prove you're an expert, not just likable

→ Why rapport is an ongoing process, not a one-time event

Listen now: https://lnkd.in/eDs2mfSZ

We glorify the benefits of entrepreneurship like independence, ownership, optionality. 

But those are the very things that crush entrepreneurs once they get going. 

Having an infinite number of options. 
Virtually no certainty while making huge decisions. 
But owning the outcome entirely. 

It's the freedom people think they want. 

But it drives a lot of entrepreneurs crazy once they get it. 

They can't make decisions. And when they do, the immediately doubt themselves and change directions. 

Which basically makes only one thing certain: they won't move forward.

I watched an entrepreneur change their mind on lead gen strategies 8 times recently. 

And I recorded a 10 min podcast breaking down why this happens (from experience). And how we can flip the script on uncertainty. 

Listen in here: https://lnkd.in/eujidhhV

The MSP owner on the phone with me sounded defeated.

His sales rep had just spent three weeks and 20+ hours on what looked like a perfect fit.

Discovery had uncovered real pain points. The assessment was thorough. The proposal meeting went well—good questions, engagement, positive energy.

Then... nothing.

Not a “no thanks.”
Not a “we’re going with someone else.”
Not even a “we need more time.”

Just complete radio silence after weeks of investment.

“This keeps happening,” he told me. “How do we stop bleeding time on deals that were never going to close?”

This was my response:

Open article: Stop Chasing Dead Deals: How to Read Your MSP Prospects Before They Ghost You by mspsuccess.com

Stop Chasing Dead Deals: How to Read Your MSP Prospects Before They Ghost You

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

Welcome to yr cyber flight simulator. 

I promise I won’t make u cry. 

The Cyber Range has been a faithful workhorse of Rogers Cybersecure Catalyst, Toronto Metropolitan University. 

Incident response professionals, IT teams, municipal leaders, law enforcement officers, veterans, and foreign partners have gone through their paces at the range. 

Has yr team seen what a cyber incident looks like?

Have they been in the hot seat, trying to make sense of what’s happening and needing to coordinate and prioritise actions?

Have they been given the rigor of training to sharpen their instinct, rehearsal their articulation, and coordinate competitions priorities?

This is your cyber flight simulator. 

Step in and see what happens when the rubber hits the road. 

Or are you going to take the risk and wait for a real incident to find out?

Good luck. 
Godspeed. 


P.S 
Please follow Rogers Cybersecure Catalyst, Toronto Metropolitan University. 

We have been delivering exciting programs to individuals and organizations for years and have shaped Canadian’s Cyber Ecosystem. 

It’s going to be an eventful year. 

Follow + try to keep up w the Catalyst.

I once received AAR feedback from an executive that changed how I view these "mundane" reports.

After-action reports are very important to the success of an exercise program. Without it, there is no chance of leadership buy-in, and soon the program will fizzle out.

These are typical uses/benefits of an AAR.

• capture lessons learned
• provide recap of proceedings
• serve as evidence for risk/auditors
• feeds into enterprise-wide action item register

On this occasion, I drafted the AAR for a fraud-related exercise. It involved many operational teams including executive involvement. The AAR was signed and sent.

One feedback from an executive stood out.

"It had alot of detail, but I don't know if it was a success".

That struck me. We just missed an opportunity.

An opportunity to highlight:
• the alignment with the overall security program
• the collaboration involved to run the exercise
• the advancement in teamwork 
• the reduction of risk

Include a clear story and highlight the win in your AAR.

Don't take these exercises and artefacts for granted.
Each event builds confidence, familiarity, and resilience.
Don't let it go unnoticed; give it its due credit.

P.S Have you seen AARs put to good use?

Most cyber CEOs think LinkedIn is about “posting more.”

It’s about posting with a positioning equation:
Authority + Trust + Leads

Don't start without a clear content strategy.

Here’s the simple way to build your content calendar.

𝗔𝘂𝘁𝗵𝗼𝗿𝗶𝘁𝘆
1. Build authority so you become the obvious expert.
Authority is when your audience says,
“This person knows the space.”

Teach one niche concept per post (one takeaway).

Share your lived experienced not conceptual ones.

Break down “why this fails” in real environments.

Add proof when possible:
Lessons, patterns, results, before/after.
Authority posts go deep in your niche.
More “results, insights, wisdom.” Less "frameworks"

𝗧𝗿𝘂𝘀𝘁
2. Build trust so people believe in what you stand for.
Trust is when your audience says,
“I’d take a meeting with them.”
It comes from clarity and consistency, not hype.

Show how you think, how you communicate risk, and how you make tradeoffs under constraints. Use stories, principles, and honest calls on what you will and won’t do. When people understand how you deal with situations, they start to trust your delivery.

𝗟𝗲𝗮𝗱𝘀
3. Generate leads without sounding salesy.

Direct: a clear CTA after you have earned it.

Indirect: a walkthrough of what it is like working w you.

Remove friction:
scope, timeline, roles involved, what success looks like.

Make it obvious you solve this specific problem for this specific buyer. Lead posts can be direct or indirect, and “walk-through” posts remove buying friction fast.

If you want a repeatable content calendar, stop brainstorming topics.

P.S Do you start writing without a plan?

Thanks Timothy Martens for prompt inspiration.

And Gerald Auger, Ph.D. + Mike Miller
for the reminder to include an image =)

How was your first full week at work?

This will happen if you don't intervene.

The Rule of the First 5 Days is a stock market indicator that states that if the market performs positively in the first 5 trading days of the year, there is a high probability that the markets will end the year positively.

Historical probabilities are between 69 - 84%.

Some of the reasons are:
Early Positioning
Investor Sentiment
Self-Fulfilling Prophecy


Bringing it back to how was your first week back at work?

Busy?
Stressed?
Juggling priorities?

Chances are if you don't make any changes, this will be how your year pans out.


If you had a great week, keep at it!

If not, time to review:
- the triggers
- the pain points
- the larger picture
- the longer term goals

Good luck for week 2!

P.S Dow has best 5-day start to year since 2006!

bootcamp

Sign up here:
https://catalystcorporatetraining.classe365.com/form/view/AutoBootCamp?_gl=1*9rfqtg*_ga*MTQ4NTczNDM0MC4xNjk4MjQxODM1*_ga_YYXBQS6S5Q*MTcwNzgzMzEyNi4xODEuMS4xNzA3ODMzMTYwLjI2LjAuMA

Time is flying by. Jan is almost over. 

This is 1 thing I miss from 10 years ago. 


My lucious hair that would give me a chance at K-pop auditions. 

Just kidding. I stand no chance. 



What do u miss from 10 years ago?




Thanks sir Chris Chia for taking this pic and sending it again to me recently!

Leader, Coach, Facilitator

If your cyber exercise doesn't make you sweat,

why do you call it an exercise?

Too many teams are taking a stroll during tabletop exercises. They don't prepare in advance, they talk in circles, and frankly take it too lightly.

I have seen teams prepare extensively for exercises.

They relook their process and hold internal preparation meetings to validate if it still makes sense. They ask tough questions internally and the leaders confirm if their assumptions about alternatives, recovery times, capabilities, and priorities are still accurate.

The best teams go in well-prepared and respond confidently. This is not just for show. This is an opportunity where leadership teams have recognized the importance of readiness and set aside protected time to be intentional about preparation. 

This only happens if the exercise program is well-socialized.
When the experience and outputs are understood.
And the leadership is serious about training.

Otherwise, what's the point?
Check a box? It's 2026, do better.

Your next Cyber TTX will be miles better with this small tweak. 

Don’t rush the start of the exercise. 

I know you have been planning it for months. Your adrenaline is pumping and you assume the participants are chomping at the bit to begin. 

But don’t neglect the pre ex brief. 

Here’s why it matters. 

1. Not everyone is familiar w exercises

Some have never participated in one. 
Others can’t remember what it’s like. 
1 or 2 even have weird assumptions. 

2. Remind everyone of the Why

The stakeholders are not equally invested in the exercise or outcome. Half are wondering why they are there. 

3. A good start is important

Some exercises that start poorly can result in minutes of waffling, rabbit holes or just straight up disengagement. 

4. Questions forces a buy-in

Facilitate a short quiz or discussion. 
This makes participants feel involved and helps them warm up as well. 

5. Simple introductions helps

You will be surprised how often teams don’t know each other or what role they play in an incident. 
Take time to do a roundtable intro. 

6. Sponsor emphasis 

Allow the exercise sponsor to speak. 
This reiterates the investment, focus, and important of the exercise. 

7. Calms your nerves

Address concerns before an exercise can help mitigate against difficult scenarios such as wrong expectations and challenging stakeholders. 
There will also be disruption but touching on some issues early helps. 

The next time you plan yr exercise. 
Spend abit more time on the start. 
It will be worth it. 

P.S any other exercise faux pax?

What most Cyber CEOs post on LinkedIn 
 
- repost their company's post 
- post about the latest hack 
- random AI blog 
 
What should Cyber CEOs post on LinkedIn 
 
- customer success stories 
- lessons learned about your business 
- strong opinion about industry issues 
 
You are the leader. 
 
Lead by example. 
 
Here are more post ideas. 

Subject Matter Expertise
- insights
- pain-points
- transformation
- trends + opinion
- counter-trends
- mistakes you have seen others made

Trust
- client success stories
- decision-making dilemmas
- framework for decision-making 
- social proof
- results

Character
- guiding principles
- values
- client examples
- stories of resilience
- leadership

Authenticity
- challenges that excite you
- lessons learned
- challenges that you overcame
- best advice that you received

Majority of my bosses in Cybersecurity have been female.

Yet female only make up 21% of the cyber workforce.

I interviewed Sarah to get her insights on Women in Cyber.

Sarah is a certified coach, facilitator, and founder of the Human Skills Leadership Lab, a unique and customizable program that helps professionals develop the human skills (or ‘soft skills’) required for effective leadership in the modern workplace. 


𝗪𝗼𝗺𝗲𝗻 𝗶𝗻 𝗖𝘆𝗯𝗲𝗿 𝗟𝗲𝗮𝗱𝗲𝗿𝘀𝗵𝗶𝗽 𝗣𝗿𝗼𝗴𝗿𝗮𝗺

1. When you think about women leading in cybersecurity, what have you noticed most often in how they lead, communicate, or navigate their roles?

They’re brilliant and discerning. They carry a full plate - navigating complex decisions and significant risk - and still, they lead with calm authority, thoughtfulness and integrity. They think deeply about their teams, their organizations, their families, and the broader systems. They’re the kind of leaders the world needs more of.


2. As you look ahead to the Women in Cyber Leadership Program in Malaysia with the Catalyst, what aspects of the program are you most curious or energized about?
   
After 4 years collaborating with the Catalyst to support cyber leaders from across Canada, I’m incredibly excited to connect with cyber leaders from 7 countries across ASEAN. It will be thrilling to be part of the conversation as these women come together to learn from and with each other.

 

If you enjoyed this interview series, please follow Sarah Lang (MA, PCC, CPCC). She is a human skills expert, a Leadership in Communication Skills Coach, and has trained leaders from leading corporations and brands.

P.S. How are companies promoting diversity?

Soft Skills Expert • Certified Leadership & Public Speaking Coach & Facilitator • Program Design and Instruction @ U Toronto, KPMG, ESRI, Rogers • I help leaders transform confidence into connection and influence.

I trained Principle Warfare Officers. 

We assessed them on 3 attributes. 

The Principle Warfare Officer (PWO) was responsible for fighting the ship. 

This included the deployment of weapons, manoeuvres, and in many cases the control of multiple ships and aircraft to fulfil a mission. 

These are the 3 attributes. 

Knowledge 
- know the procedures 
- know the asset capabilities
- know the adversary’s capabilities 
- know the ever changing situation 

Command and control
- clarity of situation  
- clarity of instruction 
- clarity of orchestration

Creativity 
- demonstrates intuition 
- demonstrates flexibility 
- demonstrates adaptability 


In cybersecurity operations,

We assess
.
.
.
.
.

Hope you get my point. 

Happy training.

Most cyber CEOs aren’t afraid to post.
They’re afraid to be misunderstood.

And 19 other myths of writing on LinkedIn. 

 1. “I’ll get DMs from random people and waste time.”
 2. “If I post about a niche topic, it’ll limit my market.”
 3. “I should wait until my messaging is perfect.”
 4. “I’ll get fact-checked and embarrassed.”
 5. “I’ll be judged by peers in the industry.”
 6. “Clients will think I’m wasting time.”
 7. “I’m not a ‘social media' person.’”
 8. “I need a hot take every time.”
 9. “I’ll look like I’m bragging.”
10. “My team will cringe.”
11. “I need perfect writing.”
12. “People will think I’m selling.”
13. “I’ll attract trolls or get dragged.”
14. “I’ll upset a partner/vendor/client.”
15. “My competitors will copy my ideas.
16. “I’m not ‘big enough’ to have opinions.”
17. “If I post, I’m giving away the secret sauce.”
18. “Need to sound super technical to be credible.”
19. “If engagement is low, it means I’m bad at this.” 

P.S which is your fav? Mine is #8  🔥

AI tools are being used in yr org. 
Have your IR plans kept up?
Here are 4 changes to make. 

Implementing AI tools have left security team scrambling over the last couple of years to ensure it is securely deployed and monitored. 

Your incident response plans may have be neglected in the process. 

Consider these updates. 

1. Include AI related incidents 

- sensitive data exposure
- supply chain vulnerabilities 
- unauthorised model changes 

Don’t assume your plan is a catchall. 
AI asset owners don’t fully understand the security risks. 

2. Validate asset + contact list

- AI asset owners 
- data architects r crucial
- most of these folks r probably new

These AI gurus have been heads down focused on speed on implementation. They probably can’t spell cyber if u meet them for the first time on an incident call. 

3. AI specific containment

- understand the impacts 
- ask if traditional options will work

It’s going to get more complex as AI tools integrate across enterprise. It may soon become so entrenched that disabling it is a non option. 

4. Logs and investigation 

- review if current threshold is valid
- check on logs before/after go-live

You will learn to love “black boxes” and need to navigate round them. 


P.S what other areas to add?

2.

Incident response plans only play a small part in cyber resilience. 

“Do you have an IR plan?”

Is probably one of the most common question that consultants and experts use to gauge a company’s resilience. 

Many teams are happy to tick yes. 

But having a plan is merely the start. 

Here’s why:
- high turnover of staff
- fast pace of tech change
- lots of assumptions remain  
- plans get outdated due to new tech 
- teams don’t use the playbooks/plans
- primary teams hardly get trained
- secondary teams ignored 
- random cyber exercises 
- no training plan

There is barely any focus on training. 

7 men squads in the military get more training time and resources than multi-million dollar cyber defence teams protecting our financial ecosystem. 

Will having a plan alone save you?

And how long are you going to assumed your team is ready?

P.S the world is still a vulnerable place

Human skills training will unlock your career potential.

These are your advantages against AI... for now.

I interviewed Sarah to get her insights on human skills.

Sarah is a certified coach, facilitator, and founder of the Human Skills Leadership Lab, a unique and customizable program that helps professionals develop the human skills (or ‘soft skills’) required for effective leadership in the modern workplace. 


𝗛𝘂𝗺𝗮𝗻 𝗦𝗸𝗶𝗹𝗹𝘀 𝗧𝗿𝗮𝗶𝗻𝗶𝗻𝗴

1. What are some of the key human skills that will unlock an individual’s potential in the workplace?
   
First: self-awareness, because awareness always precedes change. From there, the skills of emotional intelligence, listening and clear communication. These will help you improve your relationships and increase your influence and impact.


2. Were there pivotal moments from your own experience or from those that you coached that reaffirm that Human Skills Training is a vital part of career development?

I’m reminded of this everyday, given how easy it is to outsource one’s thinking, ideas, and voice to AI. We’re constantly pitched the benefits of efficiency, when really it’s our unique essence as a human that makes us compelling. Human skills will always be vital to professional and personal development.  


If you enjoyed this interview series, please follow Sarah Lang (MA, PCC, CPCC). She is a human skills expert, a Leadership in Communication Skills Coach, and has trained leaders from leading corporations and brands.

P.S. Are you worried about AI impacting yr career?

5 LinkedIn posts that should be part of your pre-RSAC marketing plan. 

If your Head of Marketing is not bugging you to start posting on LinkedIn before RSAC, ask them why?

Even better if they tell u what to post. 

Here’s 5 posts that I will write. 

“Heading to RSAC next week. Here’s the one question I’m asking every CISO I meet.”

“One year ago, [Client Type] was struggling with [Specific Problem]. Here’s what changed.”

“Everyone’s talking about [Trending Topic] at RSA. Here’s what they’re missing.”

“We’re bringing [Specific Thing] to RSA. Here’s why we built it.”

“I have 8 meeting slots open during RSA. Here’s who I wld love to talk to.”

_____________

Here’s 3 reasons why you shld post. 


REASON 1: 
Conferences are chaotic. 

This gives you a chance to cut through the noise.  

REASON 2: 
Post-Conference follow-up success is built upon pre-conference interaction.  

Unless you are a magician and can engage random folks on the floor. 

REASON 3: 
Yr competitors are already doing so. 

Silence = Falling Behind

You don’t want to waste all that $$$$

———————

No time to write?
Overwhelmed by the preparation?
Rather spend time on client demos?

Let’s work together and take that off your plate.

LinkedIn posts can be complicated.  

I simplify it by 3-2-1 method. 

3 types of posts 
- authority 
- leads 
- trust

Cycle this through the week. 

2 content pillars
- cybersecurity exercises
- LinkedIn copywriting 

Alternate pillars per day. 

1 target audience per post

Focus on 1 reader. 


What’s your 3-2-1?
⬇️

People judge within 7 seconds of opening yr mouth.

That's why I still get nervous before every presentation.

I interviewed Sarah Lang to get her insights on public speaking and establishing leadership presence.

Sarah is a certified coach, facilitator, and founder of the Human Skills Leadership Lab, a unique and customizable program that helps professionals develop the human skills (or ‘soft skills’) required for effective leadership in the modern workplace. 


𝗔𝗰𝘁𝗶𝗼𝗻𝗮𝗯𝗹𝗲 𝘁𝗶𝗽𝘀 𝗳𝗼𝗿 𝗹𝗲𝗮𝗱𝗲𝗿𝘀𝗵𝗶𝗽 𝗽𝗿𝗲𝘀𝗲𝗻𝗰𝗲

1. How would you explain what leadership presence is for those looking to grow in their career?
   
Leadership presence is your ability to stay grounded and intentional in all moments - including when you’re under pressure. In a society driven by distraction and dopamine hits, leaders who embody this type of presence, steadiness and self-trust stand out.  


2. What are some ways to practice being more grounded and present?

• Spend time on analogue hobbies that anchor you to the physical world - art, books, gardening, cooking, etc.
• Practice mono-tasking on purpose.
• Try slowing down your communication - listening, speaking, pausing, saying less.
• Regulate your nervous system with breathwork, yoga or grounding activities.
• Carve out daily moments to pause and transition between meetings and events


3. Presenting to an audience is a real fear for many professionals. Do you have a couple of tips that you usually teach?
   
First, get crystal-clear on what you’re trying to say and why it matters to your audience. Then, practice your vocal and non-verbal delivery to make sure you sound like you care about what you’re saying! I also teach simple ways to work with nerves rather than fight them so speakers can stay connected to themselves and their audience.
 

If you enjoyed this interview series, please follow Sarah Lang (MA, PCC, CPCC). She is a human skills expert, a Leadership in Communication Skills Coach, and has trained leaders from leading corporations and brands.

P.S. What's the best advice u received on public speaking?

Most Cyber CEOs post randomly and wonder why LinkedIn isn't working.
They write when inspiration strikes.
They share whatever feels right in the moment.
They post about the latest breach one day, their product the next, then go silent for weeks.

The result? Confusion. Zero traction. Wasted effort.

Here's what you should be doing instead:
Plan your content around 3 post types.

1. Authority posts
This is where you demonstrate expertise.
Share insights from client engagements. Dive deep into problems you're solving. Break down complex security concepts.

Examples:
"5 issues all enterprises face with AI governance"
"How we helped Company X reduce risk by 40%"
"The biggest misconception about Zero Trust"

These posts establish you as the expert in your niche.

2. Trust posts
This is where you build relationships.
Share your founder journey. Talk about team culture. Reveal the challenges you've overcome.

Examples:
"Why we started this company in 2019"
"The toughest decision I made as CEO"
"What our clients don't see behind the scenes"

These posts show the human behind the solution.

3. Lead posts
This is where you attract prospects.
Address pain points directly. Show transformation. Make your solution crystal clear.

Examples:
"Overwhelmed with compliance requirements?"
"How we saved a client 2000 hours per year"
"Is your board asking about AI risks?"

These posts turn readers into conversations.

Now here's the system:

Mon: Authority post
Wed: Trust post
Fri: Lead post

Repeat this for 6 months minimum.
Map out topics under each category. 
Populate your calendar. 

Never start from a blank page again.

Most cyber CEOs will read this and do nothing.

They'll keep posting randomly.
They'll keep getting zero results.
Don't be most CEOs.

Plan your content. Execute consistently. 
P.S. What type of post do you struggle with most?

Worried about the removal of your role?
Don't be a deer in headlights.
Do this immediately.

2025/2026 is the new 2020.

The trigger is different.
Lockdown vs AI.
The outcome is becoming the same.

And we shouldn't really be surprised...
If you are, stop living under a rock.

What did you think would happen?

Just look around the wider workforce, companies, tasks, processes, meetings, discussions, emails.....

Bots will be much better at most of that.

Thanks Sherlock, so is that the end for the human worker?

Maybe.... but not yet.

So, until we start serving robotic overloads, let's prepare and control what we can.

These are 5 things I'll immediately do to mitigate job risk.

1. Get better at your work

Thanks, Captain Obvious.
You are welcome, but I made Major.

The people who are most worried are probably the ones with the most areas to improve...so if there was a time to buck up, its now.

Say yes more than no.
Spend that extra hour.
Put in that additional effort.
Put yr hand up for that project.
Capture your achievements.
Socialize the wins w teams.
Help other teams win.


2. Restart your network

Your Rolodex is creaky, I know, but it is time to revisit.

It will be awkward at the start, but keep at it.
Better now than when you "need" a job.

Pro Tip: Be genuinely interested in them

Your older connections are easier to rekindle than establishing new ones. 


3. Build your profile

Refresh and improve your LinkedIn profile + professional portfolio.

It's 2026, we go to your profile and website if we want to get a good sense of who you are.

How are you showing up?
• old dated profile pic
• high school quality about section
• boring as f experience description

Or are you invisible?
Makes sense if you are James Bond.


4. Grow your network

Do some research. 

Who are your peers?
Who is in your dream role?
Which are the interesting companies?

Some of the folks who reported to you may now be execs.

Don't wait till your need a network to build one.

The earlier you start the better.

What are you waiting for? The HR Call?



5. Think like an owner

This is the future of the worker.
Gone are the days of 40 year old career.
My mom celebrates 45 years at 1 company soon!

If you think like an owner, you stop waiting for permission.

You start taking action, owning the risks, and keep going.

What is one thing you think will change when there is this mindset shift from employee to "owner worker"?

Canada's finance sector = ~8% of GDP.
No surprise that it is highly regulated.
And extremely difficult to get a foothold.

In fact, most companies will baulk at the requirements, due diligence, scrutiny, and death by a thousand cuts before they even see a dollar return.

It is a tricky environment. 
And that's the beauty of this program.

The RBC FinSec Incubator, bridges the gap between the needs of the financial sector and emerging fintech and cybersecurity startups. It helps early-stage companies transform the financial ecosystem by enhancing product security and resilience to achieve product-market fit.

Designed for early-stage Canadian fintech startups:
- specialized workshops
- no equity, no cost
- 1 to 1 mentorship

Apply here today: https://lnkd.in/gpmeAftH

Registrations close on 𝗝𝗮𝗻 𝟭𝟲

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