Microsoft’s November 2025 Licensing Shake-Up: When Your Discount Ladder Turns Into a Snake
When Microsoft licensing changes from being a ladder to being a snake.
The facts (quick recap)
Straight from Microsoft’s own neighborhood watch (and summarized neatly by Fusion Connect):
Effective November 1, 2025, Microsoft ends tiered volume discounts (Levels B–D) for Online Services at EA/MPSA/OSPA renewal. Everyone pays Level A (list) pricing—yes, even you, global megacorp.
Price impact: larger enterprises could see up to ~12% increases; many mid-market orgs ~6–9%.
EAs under ~2,400 seats won’t be renewed; Microsoft will nudge these customers to CSP models.
Exceptions: On-prem pricing unchanged; Government and Education (GCC/EES) not affected.
Microsoft’s rationale: “standardized pricing,” more “transparency,” and—my favorite—alignment with the likes of AWS and Google Cloud.
That’s the setup. Now the reaction.
Why big enterprises will be furious
Large corporates built procurement strategies, budgets, and career plans on the EA discount ladder. Removing tiering does more than hike costs; it breaks the logic of “buy more, pay less.” Expect:
Budget shocks at renewal: models built on C/D tiers suddenly don’t foot. Finance will search for a culprit; it will find your name and Microsoft’s invoice.
Less negotiating leverage: no tiers means fewer knobs to turn. Procurement’s “hero moment” becomes a cost-containment apology tour.
“Growth into discounts” disappears: variable headcount orgs lose a natural buffer. Seasonal hiring now just costs… more.
Board optics: CEOs don’t love paying list price like a casual tourist. To them, this looks like market power flexing, not transparency.
Will Microsoft say this is abuse of dominance? Of course not. Will many large enterprises feel like it is? Absolutely. I suspect Microsoft knows many of their clients will pay this, but those same customers will resent this.
With the tiered pricing Microsoft at least pretended that it was a partnership. Now it’s abundantly clear that Microsoft has decided to not bother buying you dinner before robbing you. Perhaps in the grand scheme of things the extra cost can simply be written off as a cost of doing business. But I believe many clients will feel a rubicon has been crossed and that they will need to at least have a plan B, even if they choose not to take it, yet.
Abuse of dominance—or just “transparency”?
I’ve spent the better part of three decades watching markets harden around a single vendor’s gravity well. When a near-ubiquitous provider turns price complexity into price uniformity—and the net effect is that you pay more—that’s not what CFOs mean by “simplification.” It’s what my book Who Put That Idiot in Charge? calls a narrative pivot: rebrand a margin expansion as customer love.
Let’s be fair: AWS and Google Cloud preach list-price clarity too. But Microsoft isn’t just a cloud provider; M365 + Teams sit at the core of daily work. The line between productivity standard and regulatory eyebrow-raiser gets thinner when the “standard” also gets pricier in one stroke.
The opening for Google (and friends)
For the first time in ages, Microsoft just handed competitors a credible wedge. If I’m Google, here’s my three-move combination:
Procurement Relief
Offer EA-style predictability without the “surprise, it’s Level A for everyone.” Price bands tied to commitment, adoption milestones, and measurable outcomes (security posture, automation gains). CFOs want forecastability more than they want another glossy deck.Switching-Cost Arbitrage
Subsidize migration, change management, and coexistence. Bake in dual-running periods and interoperability guarantees. Make the first 120 days operationally safe and politically defensible for CIOs.Outcomes > Features
Compete on business outcomes—faster onboarding, lower security incidents, reduced SaaS sprawl—not checkbox features. (Chapter 4 of Competitive Intelligence Playbook if you want the playbook; bring coffee.)
Others can pile on: Zoom (room experiences + telephony), Slack/Salesforce (workflow gravity), Cisco/Webex (regulated industries), even specialist CSPs who can package flexibility and white-glove support that Microsoft’s scale struggles to match.
The 12-Vector opportunity (how to actually win)
Applying Excession Events’ 12-Vector System, here’s where rivals can poke holes today:
Pricing Architecture: Replace “one list for all” with outcome-based tiers.
Procurement Friction: Pre-approved paper, ≤2-week security review, CFO-ready TCO models.
Switching Costs: Tooling for mail/cal migration, policy mapping, and identity federation out of the box.
Ecosystem: Deep ISV bundles (security, compliance, archive) that neutralize Microsoft’s bundling advantage.
Service & Success: Named CSMs with adoption SLAs tied to rebates.
Governance/Compliance: Native controls and attestations matching M365 baselines to de-risk audit questions.
User Experience: Zero-learning-curve migration aids; “meet users where they are” coexistence.
Data & Telemetry: Prove productivity and security outcomes with observable metrics the CFO can trust.
Do these well and you’re not just cheaper—you’re easier to buy, safer to own, and harder to fire.
What C-suites should do now (defensive and offensive)
Model the delta: Assume Level A at renewal; quantify 1-, 3-, and 5-year OPEX lifts.
Scenario plan: Pilot Google Workspace + Meet or a CSP-optimized M365 package. Use real data.
Exploit CSP agility: Monthly billing, flexible seat management, and license hygiene to offset hikes.
Negotiate outcomes: Tie any commitment to adoption, security, or automation improvements—not just seats.
Communicate up: No CFO likes “surprise spend.” Pre-brief now; control the narrative later.
Visuals you can steal for the board deck
Before/After Price Ladder: A→D tiers collapsing to Level A (impact by headcount).
Budget Shock Waterfall: Renewal variance with CSP optimization offsets.
12-Vector Heatmap: Where alternatives over-index vs Microsoft.
Migration Risk Radar: Governance, identity, data, change-management mitigations.
Simon Dudley is a technology strategist, bestselling author, and former senior executive at Logitech, Lifesize, and Polycom. He leads Excession Events, helping companies win beyond price and features.
#Microsoft #EnterpriseAgreement #M365 #Teams #SaaSPricing #CSP #GoogleWorkspace #AV #VideoCollaboration #Procurement #SwitchingCosts #CompetitiveIntelligence #Antitrust #CIO #CFO #DigitalTransformation #ExcessionEvents
How big is big in a data breach?
Data Breech.
I. Introduction: The Volume Illusion – Is 1TB Really Worse Than 10KB?
Data isn’t like money, losing more isn’t worse. Quality matters far more than quantity.
We've become accustomed to a certain scale of digital drama. Headlines scream about breaches involving millions of records, gigabytes upon gigabytes of pilfered data. We gasp, shake our heads, and perhaps change our passwords… eventually. But what about the smaller leaks, the drips and drabs that barely register on the Richter scale of cybercrime? Do we dismiss them, assuming their impact is negligible? That, my friends, is a dangerous game to play in the age of Artificial Intelligence.
The underlying misconception is simple: bigger equals worse. A terabyte breach must be catastrophic, a mere ten kilobytes, a mosquito bite. But this quantitative view is increasingly obsolete. The truth, unsettling as it may be, is that in the age of AI, it’s not how much data leaks, but what kind of data. A single, strategically chosen drop of the right information can trigger a cascade of consequences, a digital domino effect that can bring individuals and organizations to their knees.
In this exploration, we'll delve into the evolving definition of “sensitive” data, examine how AI amplifies the dangers of even seemingly insignificant leaks, and contemplate the regulatory and technological landscapes that are struggling to keep pace. Prepare to challenge your assumptions about data security, because the future, as always, is already here.
II. Beyond the Numbers: What "Sensitive" Really Means in Data Breaches
Let's cast our minds back – not too far, perhaps a decade or so. The primary concern in data breaches was volume. The more Social Security numbers, birthdates, and addresses a thief could amass, the more identities they could steal, the more fraudulent credit cards they could open. It was a numbers game, a brute-force assault on personal information.
But the landscape has shifted. Today, precision is key. It's no longer about quantity; it's about the specific data points that, when combined, unlock access, manipulate opinions, or trigger automated systems. What constitutes "sensitive" data has expanded far beyond the traditional categories.
Consider this:
Personal Goldmines: Yes, PII (Personally Identifiable Information) – names, addresses, driver's license numbers, passport details – remains valuable. Financial details like credit card numbers and bank account information are, of course, highly prized. And medical records (Protected Health Information or PHI), with their intricate details of our vulnerabilities, are perpetually at risk.
Digital Keys: Usernames and passwords, the gatekeepers of our online lives, remain prime targets. But access credentials to internal systems, cloud platforms, and critical infrastructure are even more so. These are the keys to the kingdom.
Business Secrets: Trade secrets, strategic plans, intellectual property – the lifeblood of any organization – are increasingly vulnerable to exfiltration. The loss of this information can cripple a company's competitive advantage for years to come.
The Deeply Personal: This is where things get truly nuanced. Biometric data (fingerprints, facial scans), genetic information, and even political or religious beliefs are now considered sensitive. Think about the implications for targeted disinformation campaigns or personalized blackmail. And let's not forget the ever-watchful eye of GDPR, demanding stringent protection for this most personal of data.
And here's the kicker: seemingly "harmless" data points, when linked together, can become explosive. A name, combined with a publicly available address and a stated political affiliation, can be used to target individuals with personalized propaganda. A seemingly innocuous purchase history, when analyzed using AI, can reveal intimate details about a person's health or lifestyle. The sum, as they say, is often far greater than the parts.
III. The Butterfly Effect: When Small Leaks Cause Big Waves
The consequences of even minor data breaches can ripple outwards, creating unforeseen and often devastating effects. Consider the potential fallout:
For You, The Individual: Identity theft remains a persistent threat, leading to fraudulent accounts, drained savings, and a financial quagmire that can take years to resolve. But beyond the financial impact, there's the emotional toll – the anxiety, the fear, the feeling of vulnerability that lingers long after the immediate crisis has passed. And because smaller breaches often go unnoticed for longer, victims remain exposed, unaware of the danger lurking in the digital shadows.
For Them, The Organizations: Reputation is everything. Losing customer trust is like losing a limb – incredibly difficult, if not impossible, to fully recover from. Then there are the financial penalties – massive fines, legal fees, compensation to victims. We're talking about sums that can reach into the millions, even for relatively small breaches. And let's not forget the operational chaos, the competitive disadvantage, and the demoralized employees that can result from a security incident.
Let's look at some real-world examples:
The Disgruntled Insider: A former employee, armed with access credentials, downloads sensitive data before leaving. This could be customer lists, proprietary code, or confidential financial information. Cases like Tesla or the South Georgia Medical Center demonstrate the vulnerability from within.
The Accidental Oops: A misconfigured cloud storage bucket exposes sensitive data to the public internet. This could be anything from medical records to financial statements. The Pegasus Airlines incident serves as a stark reminder of the potential for catastrophic errors.
The Small Guys, Big Impact: A leak at a small nonprofit organization serving vulnerable populations can have a disproportionately devastating impact on the individuals it serves. Imagine the consequences of exposing the identities and locations of victims of domestic violence or human trafficking.
IV. Enter AI: The Turbocharger for Cybercrime
Artificial intelligence is no longer a futuristic fantasy; it's a present-day reality, permeating every aspect of our lives. And while AI offers immense potential for good, it's also a powerful tool in the hands of malicious actors.
AI isn't just for chatbots anymore. It's being used to enhance and automate cyberattacks in ways we could only have imagined a few years ago.
Consider these examples:
Phishing on Steroids: AI-powered phishing attacks are hyper-personalized, ultra-convincing, and increasingly difficult to detect. Deepfakes, realistic video and audio forgeries, are used to impersonate trusted individuals, making it easier to trick victims into divulging sensitive information.
Malware That Learns: Adaptive, evasive malware uses AI to constantly change its code, making it harder to detect and neutralize. These viruses can learn from their environment, adapting to bypass security defenses in real time.
Automated Vulnerability Hunting: AI is being used to scan networks for vulnerabilities at speeds far exceeding human capabilities. Attackers can identify and exploit weaknesses in systems and applications before defenders even know they exist.
The "Shadow AI" Problem: The proliferation of unsanctioned AI tools, particularly free tiers of services like ChatGPT, poses a significant risk. Employees, often without realizing the implications, are using these tools to process sensitive company data, creating a potential data leakage nightmare.
The Black Box Mystery: AI models are often incredibly complex, making it difficult to understand why they make the decisions they do. This lack of transparency makes it hard to determine whether an AI system is leaking data or being used for malicious purposes.
V. The Great Debate: Volume vs. Sensitivity – Why Sensitivity Wins (Hands Down)
For years, the standard metric for measuring the severity of a data breach was simple: the number of records exposed. It was easy to quantify, easy to understand, and easy to report. But this approach is increasingly inadequate in the age of AI.
Experts across the cybersecurity field are converging on a single conclusion: sensitivity is the true measure of pain. A few hundred credit card numbers are far more damaging than millions of non-sensitive marketing emails. A single compromised password can grant access to an entire corporate network.
But here's the challenge: sensitivity is contextual, subjective, and constantly evolving. What constitutes sensitive data in one industry may not be the same in another. And regulatory landscapes vary wildly from country to country, creating a complex web of compliance requirements.
VI. Playing Catch-Up: Regulations and the Future of Data Protection
Regulators around the world are struggling to keep pace with the rapidly evolving threat landscape. We're seeing a patchwork quilt of laws and regulations, from GDPR in Europe to state-specific laws in the US (California, Oklahoma, New York, Pennsylvania), each attempting to address the challenges of data security and privacy.
The EU AI Act is a pioneering step, categorizing AI systems by risk level and imposing strict regulations on "high-risk" systems, such as those used in medical devices or critical infrastructure. This is a landmark attempt to rein in the potential harms of AI.
A key focus is on AI governance. Companies desperately need clear policies and robust access controls for AI tools. The cost of failing to implement these safeguards is staggering, both in terms of financial penalties and reputational damage.
Regulators are increasingly demanding greater transparency, accountability, and the ability to explain how AI systems make decisions. This is a critical step towards ensuring that AI is used responsibly and ethically.
VII. The AI Cyber Arms Race: What's Next?
The future of cybersecurity will be defined by an ongoing arms race between attackers and defenders, each leveraging the power of AI to gain an advantage.
We can expect to see the emergence of more sophisticated adversarial attacks on AI models, including data poisoning attacks that corrupt training data and lead to biased or unpredictable behavior. The weaponization of AI for social manipulation will also become an increasing concern.
But there's good news too. AI can also be used for defense, enabling real-time threat detection, automated incident response, and enhanced security. AI-powered systems can analyze vast amounts of data to identify and respond to threats far faster than any human analyst.
Ultimately, the key to winning the AI cyber arms race will be responsible AI development, ethical oversight, international collaboration, and holding AI developers accountable for the potential harms of their creations.
VIII. What Can You Do About It? (For Individuals & Businesses)
The fight for data security is a shared responsibility. Here's what individuals and businesses can do to protect themselves:
Individuals: Be vigilant about the information you share online. Use unique and strong passwords for every account. Enable two-factor authentication (2FA) whenever possible. Stay informed about the latest threats and scams.
Businesses:Know Your Data: Classify your data by sensitivity. Understand what information is most valuable and most vulnerable.Secure Your Data: Implement strong access controls, encryption, and regular security audits.Train Your People: Human error remains a leading cause of data breaches. Educate employees about AI risks and data hygiene best practices.Embrace AI Responsibly: Invest in AI for defense, but implement strict governance for AI tool usage.Plan for the Worst: Have a comprehensive incident response plan in place, ready to be activated in the event of a breach.
IX. Conclusion: The New Era of Data Security
We've reached a turning point in the history of data security. It's no longer about the megabytes or gigabytes, but the intimate, personal nature of the data we entrust to the digital world.
AI has irrevocably changed the game, making even small, seemingly insignificant leaks disproportionately dangerous. A single drop of the right information can trigger a cascade of consequences that can devastate individuals and organizations alike.
Vigilance, smart data management, robust security, and proactive regulatory compliance are no longer optional; they're essential for survival in our AI-driven world.
Protect your data as if your life depends on it... because in the age of AI, it just might.
About the Author
Simon Dudley is a chump. A man who believes in paying taxes, waiting his turn, the rule of law, being a decent human being. He writes a lot about strategy, technology, society, education, business, Excession Events and science.
#AI #AIsecurity #ExcessionEvents #Pexip #VQ #VideoConferencing #AVusergroup #Webex #Teams #Zoom #Cisco
Survivorship Bias in Win-Loss Analysis: Why You’re Probably Learning the Wrong Lessons
Survivorship bias
One of the great rituals of business is the win-loss analysis. Executives love it. We gather the sales team, dissect the quarter, and attempt to reverse-engineer some grand unified theory of victory.
But here’s the problem: most win-loss reviews are little more than self-congratulatory fiction. They’re not telling you why you win or lose. They’re telling you what you’d like to believe.
The culprit? Survivorship bias.
What Survivorship Bias Really Is
The classic example comes from World War II. Engineers studied returning bombers riddled with bullet holes and decided to reinforce the areas most often hit. Sensible, right? Except statistician Abraham Wald pointed out that these planes had survived those hits. The ones that didn’t come home—the real data—were silent.
In sales, we make the same mistake. We obsess over the “planes that came home”: the deals we won. We polish them into case studies, tell ourselves it was our genius strategy or our dazzling product. But the truth lies in the planes that didn’t come back—the prospects who quietly walked away, chose a competitor, or decided to do nothing at all.
How Survivorship Bias Warps Win-Loss
Most win-loss conversations sound like this:
“We won because they loved our features.”
“We won because of our relationship.”
“We won because we discounted just right.”
Lovely stories. But they only explain why a tiny subset of customers said “yes.” They say absolutely nothing about the much larger group who said “no.”
A few examples:
Your buyers say, “The demo was great.” So you assume demos are working. But those who ghosted after the demo? They found it confusing, too technical, or irrelevant.
You think, “Price isn’t an issue.” Because the ones who bought didn’t object. Meanwhile, a dozen others quietly left because the price was the issue.
You conclude, “Our sales process is frictionless.” Sure—for people who made it through. For the ones who bailed in procurement purgatory, your process was a nightmare.
This is the danger: you start optimizing your strategy around the people who already liked you. That creates a vicious cycle:
You get better at closing the same type of customer.
You ignore entire market segments who could have bought from you—if only you’d bothered to ask why they didn’t.
It’s a little like deciding your car is reliable because it made it back from one road trip. Meanwhile, the one broken down on the highway isn’t there to give you feedback.
How to Avoid It
Escaping survivorship bias isn’t complicated—but it does require discipline (and a little humility):
Interview the losses. Not just the big competitive ones, but the deals that never returned your calls. Silence is also data.
Segment your “no’s.” A loss to a competitor means one thing; a loss to “do nothing” means something else entirely. Both matter.
Treat salespeople’s explanations with suspicion. They’ll tell you losses were about “price” and wins were about “our brilliance.” Neither is the whole story.
Look for the missing planes. Where in your funnel do opportunities die? Which accounts never even considered you? That absence is a flashing neon sign you’re ignoring.
The Payoff
When you finally look at both sides—wins and losses—you get the real story:
The hidden objections that kill deals before they start.
The segments you’re unintentionally excluding.
The gap between what customers say and what they actually buy.
And perhaps most importantly: you stop mistaking survivorship bias for strategy.
Final Thought
In The Competitive Intelligence Playbook, I argue that most corporate “intelligence” is little more than cheerleading on your own scoreboard. Survivorship bias is exactly that. Studying only the wins isn’t analysis—it’s therapy.
So yes, when your team closes a big deal, raise a glass. Celebrate the win. But when it comes time to learn, spend at least as much energy on the ones that got away.
Because the real strategy—the kind that wins markets, not just deals—lives with the planes that never came home.
Simon Dudley is a technology strategist, bestselling author (The Competitive Intelligence Playbook, The End of Certainty, Who Put That Idiot in Charge), and former senior executive at Logitech, Lifesize, and Polycom. He is the Founder & CEO of Excession Events, a consultancy that helps companies compete more effectively in a world where products look increasingly similar.
Suggested Visuals/Slides
WWII bomber graphic with “bullet holes = customer feedback” and “missing planes = lost deals.”
Slide: Win-Loss Through the Lens of Survivorship Bias (Wins = noisy survivors, Losses = silent truth).
A pipeline diagram showing where “ghost deals” fall out unnoticed.
SEO/Hashtags
#CompetitiveIntelligence #WinLossAnalysis #SalesStrategy #CustomerOutcomes #VideoCollaboration #AVIndustry #Leadership #ExcessionEvents
Mike Tyson v Simon Dudley. Who wins?
Iron Mike Tyson v Simon Dudley
For a while now I’ve been thinking of how to give a real world illustration of the work we do at Excession Events. So I've decided to fight Mike Tyson.
Here’s an example. Me v Mike Tyson.
As you can see from the stats above, I have him on height and weight, and I have absolutely zero sports injuries, from a long career of sitting quietly (well not actually quietly, but you get the idea).
Now who wins?
Before you get all, oh don’t be stupid, he’d punch you to death in 5 seconds flat, I need to revel one other rather pertinent fact.
I get to choose the rules, because I’ve spent my time defining what success looks like to the market. After all I'm a good salesperson, and I know that helping the client understand the problem and helping them understand what success looks like is far far more important than knowing a bunch of specs that you need a degree in the topic to understand.
As a result we’re not going to be boxing (see above for why). We’re going to be playing chess.
Mike Tyson is actually better than it would first seem likely, having taken up the game while in prison (gulp). But I think I can take him, and certainly my chances are rather higher than if we got in the ring.
So the moral of the story? Fight on ground you can win on. Don’t play the other guy's game. Because you can never win any game where someone else is setting the rules.
Here’s a couple of examples in the real world:
You’re the big company having a small competitor running rings around you in execution?
Flip the script. Help clients understand that both solutions are more than good enough, but that you have the financial resources and history to ensure the purchasing department doesn’t have a conniption.
You’re a small player, competing against the big guy?
Talk about personal service, how the client is more than just another customer. After all you don’t have customers, you have partners.
Product getting a little long in the tooth?
Emphasis, stability, longevity, safety. Sure you don't have all the latest features, but do users even want those things? A product, that just works day in day out is the right answer.
Know thyself
Now to be clear NONE of this works if you don’t have a clear eyed understanding of your competitor and your own business.
At Excession Events we help companies understand their competitors, themselves, and then help them create the narrative that can set the rules of success.
Because there are plenty of things I can beat Iron Mike at, it's just not boxing.
About the Author
Simon Dudley is a chump. A man who believes in paying taxes, waiting his turn, the rule of law, being a decent human being. He writes a lot about strategy, technology, society, education, business, Excession Events and science.
#CompetitiveIntelligence #BusinessStrategy #MarketPositioning #SalesEnablement #LeadershipInsights #ExcessionEvents #GoToMarket #StrategicThinking #DisruptionStrategy #GrowthMindset #Logitech #HP #Owllabs #Barco #GoogleBeam #VQ #Cisco #Pexip #ChessNotBoxing
I’ve got a car to sell you
The ultimate car for a very specific type of driver
Let’s take a look at the specs:
0–60mph: 30 seconds
Top Speed: 55mph
Seats: 4
MPG: A glorious 20
Not impressed yet? Fair enough. Let’s continue.
This car is complete with a custom body kit. By “body kit,” I mean a collection of old tires tied to ropes and hung around the car, tugboat-style.
Still not rushing to sign the check?
Alright, let’s pop inside.
Radio? None.
Sat nav? Forget it.
Electronics? Only one: a local cell-phone jammer ensuring no calls or texts can be made inside.
Windows? Permanently closed.
Ok, I'll be straight with you. I have a 1995 Ford Crown Victoria to sell you.
Sounds dreadful, right? Who on earth would want this?
Well, that depends on the buyer persona.
The Right Buyer
No self-respecting adult would want to drive this beast. But if you’re the parent of a freshly licensed 16-year-old, suddenly this monstrosity looks pretty appealing. To be clear, not to your 16 year old, but to you, the concerned parent.
Glacial acceleration = No racing off into trouble.
Surrounded by tires = Parking-lot mishaps and low-speed bumps handled with ease.
No radio, no cell service = Zero distractions.
Big, heavy, and safe = Built-in crash resistance, limited top speed.
No working windows = No teenage “hey baby” antics at stoplights.
Unstressed mechanicals = Reliability for days.
All this for $3,000 + tires.
Suddenly, this looks like the perfect first car.
Thanks, I Hate It
When my older kids started driving, we did something similar. Not quite a Crown Vic, but definitely not a shiny new Jeep either—no massive car payments, no rollover risk, no constant repairs.
And that’s the point: sometimes you don’t have the best product to sell. Sometimes you’ve got the equivalent of a Crown Victoria with a busted radio.
So what do you do?
The Bigger Lesson
You find the right audience. Stop clinging to the idea that you need the “best” product to succeed. Best is subjective.
A BMW M5 is the best car… for one type of buyer.
A thirty-year-old Crown Vic wrapped in tires is the best… for another.
Same goes for your business.
If you want help figuring out who your “Crown Vic or BMW M5 audience” is, we should talk. simon@excessionevents.com
And I’d love to hear from you: what product in your career was your version of the Crown Vic?
For me, it was the Polycom ShowStation—a product so bizarre that during one demo, a friend was electrocuted by one, and fell to the floor unconscious during a demo. and most people thought that was a lucky escape. Seriously that is a true story.
About the Author
Simon Dudley is a chump. A man who believes in paying taxes, waiting his turn, the rule of law, being a decent human being. He writes a lot about strategy, technology, society, education, business, Excession Events and science.
#sellingthewrongproduct #salesaudiencetargeting #findingtherightbuyer #productmarketfit #salesstrategytips #businessstorytelling #competitiveintelligence #salesenablement #buyerpersona #businesshumor #productpositioning #saleslessons
The Unexamined Life Is Worthless (Especially in Sales)
The unexamined life is worthless
Because doing the same thing badly, over and over, is not experience — it’s stagnation.
Let’s take a quick walk down philosophy lane.
Socrates famously said, “The unexamined life is not worth living.”
He wasn’t in sales.
But if he were, he’d say: The unexamined pitch is not worth repeating.
After every win — or more importantly, every loss — you need to pause and ask: What happened? What worked? What didn’t?
Not to beat yourself up. Not to rewrite history. But to get better.
Sales is a performance sport. The top players review the tape.
Here’s what to do:
Postmortem the big ones. Why did you win that six-figure deal? Or lose it at legal? Write it down.
Look for patterns. Are you consistently losing with one persona? Fumbling the pricing slide? Missing a key stakeholder?
Adjust intentionally. Tweak. Iterate. Improve. The best sellers aren’t perfect — they’re evolving.
Growth doesn’t come from experience.
It comes from reflection.
So if your close rate’s flat but your calendar’s full?
You don’t need more calls.
You need more insight.
Sell Video, Use Video
Selling over video
Because telling clients you’re innovative via text is like faxing someone about your digital transformation strategy.
If you’re in the business of selling video solutions — or claiming to be “modern,” “cutting-edge,” or (shudder) “disruptive” — and you’re still sending walls of text instead of video?
You’re doing it wrong.
Video isn’t a novelty. It’s the new handshake. It’s the face, tone, nuance, and charisma your email will never deliver — no matter how many emojis or bullet points you use.
Want to stand out in a crowded inbox?
Send a 60-second video. Personalized. Relevant. Human.
Here’s what it does:
Builds trust. Clients see your face. Hear your tone. You go from “another vendor” to “real person with a point.”
Cuts through noise. While everyone else is “just checking in,” you’re delivering a Netflix-worthy, client-specific broadcast.
Accelerates decisions. People respond faster to people they feel connected to. Video creates that connection.
If you sell video — and don’t use it? That’s like a dentist with bad teeth.
So don’t just sell the value. Show it.
Your camera is your closing tool.
Use it.