Navigating High-Stakes Negotiation Scenarios

To Salespeople Who Are Negotiating Q4 Deals: Here's 3 steps for the ultimate "win-win" (and stop deals from falling apart) ⬇️ BACKGROUND: 90% of salespeople play negotiation “whack a mole.” Your buyer asks for a concession. You give it, assuming it will close the deal. But all you did was “feed the dragon.” “That was easy,” your buyer thinks. They're now emboldened to ask for more. Here’s what the top 10% highest paid sellers do instead: 1. Uncover ALL “Asks” Before To One. Your buyer just asked for a discount? Great. Now put your head in a straight jacket. Don’t nod and say yes. Don’t shake your head and say no. Instead ask this: “Let’s say that issue was resolved and we found a win-win. What additional ‘asks’ would you or your team have before we move forward?” If they say "nothing," proceed. But chances are, there are other issues: - billing terms - free services - payment timelines Your job is to see the forest for the trees. Understand EVERYTHING they’re asking for. Not just one individual ask. Otherwise, you'll win the battle but lose the war. 2. Uncover the Underlying Need. Got all the “asks” out on the table? Perfect. Now figure out WHY they’re asking for them. What underlying need are they trying to meet? There might be a better way of addressing it. There was once two men “negotiating” over an orange. As one of them was about to cut it in half so they could share it, one guy asked: “Wait, why do you want the orange?” Turns out, one guy wanted to eat it. The other guy wanted the peel for his beer brewing. Both got 100% of what they wanted instead of only 50%. All because one guy asked the question. Do the same with your buyers. 3. Uncover the SERIES of Next Steps. Ok. You’ve got the “asks” on the table. You understand the WHY. One last step before it’s time to negotiate: Uncover the series of steps between agreeing on the issues, and signature. After summarizing their asks, say this: “Let’s say we found a way to agree on all of the above. What series of steps would you and anyone else on your team still need to take before we move forward together?” If their answer is “nothing,” proceed. But. Half the time… They answer with something like: “Well, we still need to get our CXO bought in on the business case.” That tells me one thing: You still have SELLING to do! Not NEGOTIATING! In that situation, you can negotiate until you’re blue in the face. But it still won’t close the deal. Rule of thumb: A successful negotiation should close the deal. If it doesn’t? If there are other steps to still take AFTERWARD? You’re negotiating too early. Get the selling steps out of the way first. Then come back to the “negotiation table.” Otherwise? You're signing up for TWO negotiation cycles. Ok. That’s all for today, Did you learn something? If so, let me know in the comments with a “yes!” And if you have a question? Let me know that too.

I Asked 87 CISOs: 'What's Your #1 Red Flag in Vendor Meetings?' The Answers Will Shock You I asked 87 Fortune 1000 CISOs one simple question: "What's your #1 red flag that makes you end a vendor meeting early?" I expected to hear about pushy sales tactics or technical incompetence. What they told me was far more surprising. The #1 Red Flag (mentioned by 73% of CISOs): "When they start with 'We're like Palo Alto but better.'" One CISO put it bluntly: "If you need another company to explain what you do, you don't understand your own value." The Top 7 Red Flags That Kill Deals: 1. The Lazy Comparison (73%) Using other companies as a crutch to explain your solution. Shows you haven't done the work to articulate unique value. 2. The Fake Urgency Play (68%) "This offer expires Friday" or "Only 2 spots left at this price." CISOs manage $50M+ budgets. They know manufactured scarcity when they see it. 3. The Name Drop Without Permission (61%) "We work with [Competitor X]" when you don't. The CISO community is small. We verify everything. 4. The Demo-First Ambush (59%) Jumping into a demo without understanding our environment. It's like prescribing medicine before diagnosis. 5. The Buzzword Bingo (54%) "Our AI-powered, blockchain-enabled, quantum-ready solution..." If you can't explain it simply, you don't understand it deeply. 6. The Interruption Pattern (49%) Cutting off the CISO mid-sentence to pitch. Shows you're not here to solve problems—just to talk. 7. The Ghost References (44%) "We have amazing case studies" but can't share any. No proof = no trust = no deal. The Surprising Pattern: Notice what's NOT on this list? • Cold calling (only 12% mentioned it) • Pricing discussions (8%) • Technical limitations (6%) CISOs aren't bothered by aggressive outreach or premium pricing. They're bothered by lazy thinking and lack of preparation. What Actually Works: The CISOs who shared red flags also shared what impresses them: → Starting with: "I noticed you're migrating to AWS. Here's how we helped [Similar Company] with that exact challenge..." → Admitting limitations: "We're great at X, but if you need Y, I'd recommend [Competitor]." → Asking smart questions: "What's your biggest frustration with your current solution?" → Showing up prepared: "I saw your recent hire for cloud security. How is that initiative progressing?" The Bottom Line: Every CISO I spoke with said the same thing: "I'll take an honest vendor who understands my problems over a polished pitch any day." The bar isn't that high. Yet 90% of vendors trip over it. Your move: Pick one red flag from this list. Fix it before your next CISO meeting. Which one will you tackle first? P.S. If you want to avoid these mistakes and get warm introductions to CISOs who actually want to hear from you, let's talk. At Execweb (Acquired by CyberRisk Alliance) (A CRA Resource), we ensure you're prepared before you ever get in the room.

73% of employers expect you to negotiate. 55% of professionals don’t. That’s a costly silence. Negotiation isn’t about being difficult. It’s about showing up prepared and knowing your value. Here's how to do it right: 1. Research what’s fair ↳ Know the going rate for your role and level. 2. Know your impact ↳ Have proof of what you’ve led, built, or improved. 3. Define your range ↳ Set your target and your bottom line. 4. Look beyond salary ↳ Include PTO, bonuses, equity, flexibility. 5. Practice out loud ↳ Once is better than never. Confidence shows. Common missteps to avoid: 🚫 Accepting an offer on the spot 🚫 Leading with your lowest number 🚫 Ignoring the full compensation picture Smarter ways to respond: 🗨 “Based on what I bring, let's revisit the package.” 🗨 “What flexibility is there in total compensation?” 🗨 “Thanks. Can I take some time to review this?” Coaching 100s of people into roles they actually love  has taught me: You don’t get what you deserve. You get what you negotiate. Your new boss is expecting it. You just have to be ready. 🔖 Save this for when the offer comes in. 📤 Send it to someone who’s due for a raise. Reshare ♻️ to help someone in your network. And give me a follow for more posts like this. P.S. Looking to grow your salary? Each month, I help a select number of people get 40-80% pay bumps and land fulfilling $200K-$500K roles. DM me "Salary" to learn how.

The Trust Factor in Intercultural Negotiations: Insights from a Systematic Review Trust is essential for financial success in negotiation. I have developed the Tru$tCurrency concept and want to share this interesting study. In today's globalized world, trust is a fundamental pillar in business and negotiation. But what happens when trust is tested across cultural boundaries? A recent systematic review by Mariusz Sikorski and Prof. Dr. Arnd Albrecht, MBA (2025) sheds light on the complexities of trust in intercultural negotiations and offers valuable insights for professionals navigating global deal-making.  Trust Varies Across Cultures One of the key takeaways from the research is that trust is not universal—it varies significantly between high-trust and low-trust cultures.  - High-trust cultures (e.g., the U.S., Northern Europe, East Asia) tend to assume trust until proven otherwise.  - Low-trust cultures (e.g., Latin America, the Middle East) require more time and relationship-building before trust is granted. This has direct implications for negotiators: what works in one cultural setting may backfire in another. As Sikorski & Albrecht state, “Individuals from different cultures not only assess trustworthiness differently but also tend to trust members of other cultures to a lower degree.” Trust Repair is Harder in Intercultural Contexts Breaking trust in a negotiation is one thing—repairing it is another challenge, especially in intercultural settings. The study finds that different cultures interpret trust violations and apologies in distinct ways.  - In Western cultures, apologies typically signal responsibility and regret.  - In Japan, apologies focus on acknowledging the counterpart’s burden, rather than admitting guilt. This underscores why trust cannot be restored with a one-size-fits-all approach. Effective trust repair requires cultural intelligence and a deep understanding of the counterpart’s perspective. Implications for Global Negotiators For professionals engaged in international business, partnerships, and diplomacy, this study offers clear takeaways:  ✔ Recognize cultural differences in trust-building—some counterparts require immediate openness, others need time.  ✔ Adapt strategically—find the balance between bridging cultural gaps and maintaining authenticity.  ✔ Communicate with awareness—misinterpretations can quickly erode trust, especially across high-context and low-context cultures.  ✔ Be intentional about trust repair—apologies and solutions must align with cultural expectations. As Sikorski & Albrecht conclude, “Trust is a crucial element in negotiations, and it is even more important in intercultural contexts.” Understanding how trust is formed, lost, and regained across cultures is no longer optional—it’s essential for success. Read the full paper here: https://lnkd.in/d9pctusR

Your POC process is probably why you're not closing enterprise deals.   After analyzing POC outcomes across our portfolio, the data is clear: Companies with structured and priced POCs close 3x more deals than those running free pilots.   Why charge? Price signals seriousness. Even nominal fees filter serious buyers from tire-kickers. Frame your pilots as fixed-fee engagements: Say "we structure this as a 4-week, fixed-fee engagement to quantify value and build your business case."   Be sure to clarify pricing expectations in the process: If your pilot costs $5K but commercial deals are $100K-$300K based on the value unlocked, state this explicitly to avoid anchoring.   Here are 5 best POC best practices we see:   1. Define success criteria, not scope Align on specific KPIs, business outcomes, and who signs off before writing a line of code.   2. Time-box ruthlessly with weekly checkpoints POCs should run 30-90 days max. Set weekly or bi-weekly checkpoints to maintain urgency.   3. Pre-commit the path to commercial discussions Before starting any pilot, confirm that hitting the success metrics will trigger stakeholder presentations and commercial negotiations.   4. Demand access to the full buying center Technical users alone can't close deals. Ensure you meet decision-makers and budget holders during the POC, not after.   5. Document like a contract Formalize scope, terms, and deliverables in the agreement. Include specific responsibilities for both sides, data access requirements, success metrics, timelines, and post-POC commitments.   --   POCs are where your enterprise motion gets built. Treat them that way.   I wrote a guide to AI pricing with Madhavan Ramanujam and Joshua Bloom that discusses these ideas in more detail. If you're curious to dive deeper, I'll leave that link below. Also, Madhavan just released a new book called Scaling Innovation that also explores these topics. Highly recommend!

I’ve been in executive search long enough to see a pattern: - A company is struggling with high turnover. - They invest heavily in recruitment, employer branding, and hiring incentives. - They get excited about strong candidates-only to lose them at the final stage. Why? Because top candidates aren’t just evaluating the role-they’re evaluating the company. And the truth: If your culture is broken, your hiring process is just window dressing. Executives love to ask, “How do we attract A-players?” But they don’t always ask, “Why would an A-player choose to stay here?” - Great candidates don’t just look at salary-they look at reputation. And in the age of Glassdoor, Blind, and LinkedIn, company cultures are an open book. - They talk to past and current employees. If your people aren’t recommending your company, that’s a flashing red flag. - They assess leadership in interviews. A hiring process filled with vague answers, unclear expectations, or high-pressure urgency screams dysfunction. Your ability to recruit top talent is directly tied to your ability to build a culture that people actually want to work in. Too many leadership teams try to “sell” candidates on a dream instead of addressing the real issues driving people away. - Telling half-truths → “We have a strong culture!” (But turnover is high, and employee engagement scores are low.) - Hiding red flags → “Work-life balance is important to us.” (But leadership quietly expects 70-hour weeks.) - Ignoring internal data → Exit interviews consistently show the same culture problems, but leaders dismiss them as “one-off cases.” The best candidates don’t fall for PR spins. They see the gaps. And when they do? They walk. Leaders Need to Audit Themselves Before Hiring If you’re struggling to attract and retain top talent, ask yourself: ✅ Would I enthusiastically recommend this company to my own network? ✅ What are the top reasons employees leave-and are we actually addressing them? ✅ Are we coaching and developing leaders, or just cycling through people?  Culture isn’t what you write in your job descriptions-it’s what candidates hear in backchannel conversations. 📩 If you’re ready to build a culture that attracts—not repels—top talent, let’s connect. #ExecutiveCoaching #Leadership #TalentStrategy #CultureMatters #HighPerformanceTeams

🎖️𝐌𝐚𝐬𝐭𝐞𝐫𝐢𝐧𝐠 𝐉𝐨𝐛 𝐎𝐟𝐟𝐞𝐫 𝐍𝐞𝐠𝐨𝐭𝐢𝐚𝐭𝐢𝐨𝐧: 𝐂𝐫𝐞𝐚𝐭𝐞 𝐚 𝐖𝐢𝐧-𝐖𝐢𝐧 𝐒𝐢𝐭𝐮𝐚𝐭𝐢𝐨𝐧⁣⁣⁣🏆😎🚀 ⁣ As the founder of Raya Advisory, an executive and leadership recruiting firm, I’ve helped negotiate dozens of executive & leadership job offers! Over the past few weeks alone, we’ve placed multiple top executives and leaders into high-profile AI companies, including public ones. 🔥🔥 As an executive recruiting firm, we sit at the intersection of candidates and companies. I coach talents through offers and act as a trusted partner to our clients (AI, SaaS Enterprise, health tech companies), helping them structure offers that work for both sides. In my view, the most fundamental criterion for a successful negotiation is to “𝐂𝐫𝐞𝐚𝐭𝐞 𝐀 𝐖𝐢𝐧-𝐖𝐢𝐧 𝐒𝐢𝐭𝐮𝐚𝐭𝐢𝐨𝐧”! Here are 5 key factors to apply for a successful negotiation: 🔹 𝐏𝐮𝐭 𝐲𝐨𝐮𝐫𝐬𝐞𝐥𝐟 𝐢𝐧𝐭𝐨 𝐭𝐡𝐞 𝐩𝐚𝐫𝐭𝐲’𝐬 𝐬𝐡𝐨𝐞𝐬. See the world from the other party’s lens, understand their abilities & limitations, and know what to negotiate to close the deal. Creating a win-win situation is key in any negotiation so everyone walks away satisfied and excited about what’s ahead. 🔹 𝐓𝐡𝐢𝐧𝐤 𝐥𝐨𝐧𝐠 𝐭𝐞𝐫𝐦. Every negotiation is a chance to build trust and alignment; it’s an opportunity to make a long-lasting relationship and unlock future possibilities, not just extract value. This is particularly true about job offer negotiation. You want to start your new job on the right foot. 🔹 𝐄𝐯𝐚𝐥𝐮𝐚𝐭𝐞 𝐭𝐨𝐭𝐚𝐥 𝐜𝐨𝐦𝐩, 𝐧𝐨𝐭 𝐣𝐮𝐬𝐭 𝐭𝐡𝐞 𝐛𝐚𝐬𝐞. Stock, bonuses, benefits, and growth trajectory can significantly shift the equation. Understand the full picture before deciding. Also, think about upside potential with the company’s stock options or RSUs. Stock appreciation for public companies and IPO or M&A exist are what form the biggest part of the compensation of those who have a big earn-out. 🔹 𝐊𝐧𝐨𝐰 𝐲𝐨𝐮𝐫 𝐦𝐚𝐫𝐤𝐞𝐭 𝐯𝐚𝐥𝐮𝐞—𝐛𝐮𝐭 𝐚𝐥𝐬𝐨 𝐲𝐨𝐮𝐫 𝐮𝐧𝐢𝐪𝐮𝐞 𝐯𝐚𝐥𝐮𝐞. Benchmarking matters. But also consider what you specifically bring to this role—your track record, strategic edge, and timing. That’s what justifies a premium. 🔹 𝐁𝐞 𝐭𝐫𝐚𝐧𝐬𝐩𝐚𝐫𝐞𝐧𝐭 𝐚𝐛𝐨𝐮𝐭 𝐲𝐨𝐮𝐫 𝐠𝐨𝐚𝐥𝐬. If equity, scope, title, flexibility, or location matter more to you than base -- say it. Negotiate multiple factors if you are more open to different types of compensation packages. The best offers come from clear, honest priorities. To all the execs and rising leaders out there: if you’re navigating offers right now, I’m happy to share more insights or talk through scenarios. Let’s get you the right role, the right way.🍀 #ExecutiveSearch #NegotiationTips #AILeadership #HiringExecutives #JobSearchAdvice #LeadershipHiring #CompensationStrategy

There’s a big difference between handling objections and understanding them. Handling sounds like this: Prospect: “The other agent will sell my home for 2%, not 3% like you.” Agent: “I understand how you feel. Many people felt the same way. But what they found was that they ended up leaving money on the table because the lower-fee agents didn’t market the property as aggressively or negotiate as strongly.” When you’re convincing, you’re losing. Of course you’re going to say that. You’re biased. You have commission breath. Convincing comes across as dismissive. Understanding sounds like this: “You want to make sure you’re getting a fair deal and aren’t overpaying on commissions.” That hits differently, doesn’t it? It names what the person actually cares about. Not just the words, but the feeling behind them. When people feel understood, they relax. They stop bracing for the rebuttal. They open up because they feel like you’re with them, not against them. That’s why understanding is better. Because objections aren’t walls to climb. They’re windows into what someone values. Once people feel understood, then you can poke the bear. Ask a question that illuminates a potential knowledge gap. Examples: “With a reduced commission, the pool of agents eager to bring buyers through your door can shrink. How are you thinking about handling that trade-off?” “Part of the commission goes toward attracting buyer’s agents to your property. If that piece is reduced, it can impact exposure. How are you making sure your home still gets full visibility?” “Sometimes that 1% savings looks great on paper, but if it means your home doesn’t get as much attention or as many strong offers, it could end up costing you much more than you save. How are you weighing that trade-off?” No pushing. No pressing. No persuading. Just illuminating a knowledge gap without leading people to a desired answer. Because the goal isn’t to persuade. it’s to let people persuade themselves. Buyers have the answers. Sellers have the questions.

Too many sellers inadvertently lower their status in their attempts to "build rapport" with prospects.  Here's how you gain your prospect's RESPECT in the first 90 seconds of a call: First, let's look at how 90% of sellers try to build rapport: "𝘚𝘰 𝘸𝘩𝘦𝘳𝘦 𝘺𝘢 𝘤𝘢𝘭𝘭𝘪𝘯𝘨 𝘪𝘯 𝘧𝘳𝘰𝘮?" "𝘛𝘰𝘰 𝘣𝘢𝘥 𝘢𝘣𝘰𝘶𝘵 𝘵𝘩𝘦 𝘉𝘪𝘭𝘭𝘴, 𝘩𝘶𝘩? 𝘕𝘦𝘹𝘵 𝘴𝘦𝘢𝘴𝘰𝘯 𝘸𝘪𝘭𝘭 𝘣𝘦 𝘵𝘩𝘦𝘪𝘳 𝘺𝘦𝘢𝘳!" "𝘏𝘰𝘸'𝘴 𝘵𝘩𝘦 𝘸𝘦𝘢𝘵𝘩𝘦𝘳 𝘪𝘯 𝘓𝘈 𝘵𝘰𝘥𝘢𝘺?" ^Sports/Weather/Location based rapport isn't really rapport. It's schmoozing, and your prospect can see through that BS. 𝗧𝗵𝗲𝘆 𝗸𝗻𝗼𝘄 𝘆𝗼𝘂'𝗿𝗲 𝗷𝘂𝘀𝘁 𝘁𝗿𝘆𝗶𝗻𝗴 𝘁𝗼 𝗯𝘂𝘁𝘁𝗲𝗿 '𝗲𝗺 𝘂𝗽 𝗳𝗼𝗿 𝘁𝗵𝗲 𝘀𝗮𝗹𝗲, just like every other seller who talks about the exact same stuff! If you're OK being treated like a run of the mill salesperson, by all means continue to schmooze. For those of us who'd like different results, read on. --- The easiest way to build rapport is to show you respect your prospect's time + know something about their business. You can do this by following the 90 second rule: 𝗦𝗮𝘆𝗶𝗻𝗴/𝗗𝗼𝗶𝗻𝗴 𝘀𝗼𝗺𝗲𝘁𝗵𝗶𝗻𝗴 𝗶𝗻 𝘁𝗵𝗲 𝗳𝗶𝗿𝘀𝘁 𝟭.𝟱 𝗺𝗶𝗻𝘂𝘁𝗲𝘀 𝘁𝗵𝗮𝘁 𝘀𝗵𝗼𝘄𝘀 𝘆𝗼𝘂 𝗽𝗿𝗲𝗽𝗽𝗲𝗱 𝗳𝗼𝗿 𝘁𝗵𝗲 𝗰𝗮𝗹𝗹 𝗮𝗻𝗱 𝗸𝗻𝗼𝘄 𝘀𝗼𝗺𝗲𝘁𝗵𝗶𝗻𝗴 𝗮𝗯𝗼𝘂𝘁 𝘁𝗵𝗲𝗶𝗿 𝗯𝘂𝘀𝗶𝗻𝗲𝘀𝘀. Examples: 1. For health insurance, we might comment on a new location opening: "𝘐 𝘸𝘢𝘴 𝘱𝘳𝘦𝘱𝘱𝘪𝘯𝘨 𝘧𝘰𝘳 𝘵𝘩𝘪𝘴 𝘢𝘯𝘥 𝘴𝘢𝘸 𝘵𝘩𝘦 𝘯𝘦𝘸𝘴 𝘢𝘣𝘰𝘶𝘵 𝘵𝘩𝘦 𝘯𝘦𝘸 𝘣𝘳𝘢𝘯𝘤𝘩 𝘰𝘱𝘦𝘯𝘪𝘯𝘨 𝘪𝘯 𝘚𝘤𝘳𝘢𝘯𝘵𝘰𝘯. 𝘐𝘴 𝘵𝘩𝘢𝘵 𝘺𝘰𝘶𝘳 3𝘳𝘥 𝘯𝘦𝘸 𝘰𝘱𝘦𝘯𝘪𝘯𝘨 𝘵𝘩𝘪𝘴 𝘲𝘶𝘢𝘳𝘵𝘦𝘳?" ^New office = more employees who are going to need insurance. -- 2. For our Club Pass sales training program, we'll might comment on something we read on a job posting for an AE: "𝘋𝘢𝘯, 𝘐 𝘸𝘢𝘴 𝘳𝘦𝘢𝘥𝘪𝘯𝘨 𝘵𝘩𝘦 𝘰𝘱𝘦𝘯 𝘑𝘋 𝘺𝘰𝘶 𝘢𝘭𝘭 𝘩𝘢𝘷𝘦 𝘧𝘰𝘳 𝘵𝘩𝘦 𝘌𝘕𝘛 𝘈𝘌 𝘱𝘰𝘴𝘪𝘵𝘪𝘰𝘯. 𝘗𝘳𝘦𝘵𝘵𝘺 𝘤𝘰𝘰𝘭 𝘵𝘰 𝘴𝘦𝘦 𝘺𝘰𝘶'𝘳𝘦 𝘭𝘰𝘰𝘬𝘪𝘯𝘨 𝘵𝘰 𝘦𝘹𝘱𝘢𝘯𝘥 𝘪𝘯𝘵𝘰 𝘥𝘪𝘧𝘧𝘦𝘳𝘦𝘯𝘵 𝘷𝘦𝘳𝘵𝘪𝘤𝘢𝘭𝘴 𝘣𝘦𝘺𝘰𝘯𝘥 𝘫𝘶𝘴𝘵 𝘴𝘦𝘯𝘪𝘰𝘳 𝘭𝘪𝘷𝘪𝘯𝘨 𝘤𝘰𝘮𝘮𝘶𝘯𝘪𝘵𝘪𝘦𝘴. 𝘏𝘰𝘸'𝘴 𝘵𝘩𝘢𝘵 𝘨𝘰𝘪𝘯𝘨?" ___ To be clear, there's nothing wrong with bonding over a shared love of the Buffalo Bills, but let that be the cherry on top to your demonstration of prep + respect for their time, not the only way you build rapport. 

Here's my cheat sheet for a first-pass quantitative risk assessment. Use this as your “day-one” playbook when leadership says: “Just give us a first pass. How bad could this get?” 1. Frame the business decision - Write one sentence that links the decision to money or mission. Example: “Should we spend $X to prevent a ransomware-driven hospital shutdown?” 2. Break the decision into a risk statement - Identify the chain: Threat → Asset → Effect → Consequence. Capture each link in a short phrase. Example: “Cyber criminal group → business email → data locked → widespread outage” 3. Harvest outside evidence for frequency and magnitude - Where has this, or something close, already happened? Examples: Industry base rates, previous incidents and near misses from your incident response team, analogous incidents in other sectors 4. Fill the gaps with calibrated experts - Run a quick elicitation for frequency and magnitude (5th, 50th, and 95th percentiles). - Weight experts by calibration scores if you have them; use a simple average if you don’t. 5. Assemble priors and simulate - Feed frequencies and losses into a Monte Carlo simulation. Use Excel, Python, R, whatever’s handy. 6. Stress-test the story - Host a 30-minute premortem: “It’s a year from now. The worst happened. What did we miss?” - Adjust inputs or add/modify scenarios, then re-run the analysis. 7. Deliver the first-cut answer - Provide leadership with executive-ready extracts. Examples: Range: “10% chance annual losses exceed $50M.” Sensitivity drivers: Highlight the inputs that most affect tail loss Value of information: Which dataset would shrink uncertainty fastest. Done. You now have a defensible, numbers-based initial assessment. Good enough for a go/no-go decision and a clear roadmap for deeper analysis. This fits on a sticky note. #riskassessment #RiskManagement #cyberrisk