How To Identify Red Flags In Negotiation Scenarios

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.

4 red flags that saved me from licensing disasters in biotech: **🚩 Red Flag #1: The inventor won't engage** Had a university promote their technology, brought in the scientist for a meeting.  Great science, but he refused to take the next step. Wouldn't share data, wouldn't collaborate. He wasn't interested and you are looking for partners. Walk away immediately. Not worth it. **🚩 Red Flag #2: Zero flexibility on terms** When negotiation feels like talking to a brick wall, you're in trouble.  Everything in licensing is negotiable - timelines, milestones, payment structures.  If they won't budge on anything, they won't work with you when real problems arise. **🚩 Red Flag #3: No track record of successful deals** Do your homework on who you're licensing from. What happened to their previous partnerships? How did those relationships end? Past behavior predicts future cooperation. **🚩 Red Flag #4: You find yourself accepting terrible terms because "you need this asset"** When you're so focused on one specific technology that you'll agree to anything, you've lost your negotiating power.  The temptation is to cave because we "really want" this asset.  But desperation leads to deals that kill companies.  Always have alternatives identified, and be prepared to walk away if the terms don't work. BONUS: Build a good relationship with the other parties before going into a licensing deal. Hugely under-rated. Anything else to add?

Securing a term sheet in today's environment is challenging, but valuation isn't everything. Watch out for these red flags: 1) Excessive control provisions that limit your autonomy. I have seen veto rights, controls on hiring and firing, control on future funding rounds, or overburdensome board constructions. 2) Unreasonable deadlines for milestones. I have seen unsophisticated investors set key milestones in an attempt to “encourage” the founders to deliver, but in reality rush the team leading to mistakes and regrets. 3) Onerous liquidation preferences that can severely dilute founders. Liquidation preference determines how proceeds from an exit are distributed. I have seen 3x or worse on some term sheets. 4) Misaligned incentives prioritizing investor gains over company health. I have seen high interest rates, ratchet provisions that increase investor ownership, and even uncapped returns. 5) Burdensome reporting requirements that distract your team. I have seen groups ask for audited financials monthly and constant KPI updates. Don’t be afraid to negotiate or walk away from a term sheet. The terms you agree to now will impact your business for years to come. Any other red flags you've seen that would be helpful for founders to know? #venturecapital #startups #founders #termsheets #fundraising #earlystage

M&A Lessons from Private Equity: Reading people is one of the most important parts of an M&A transaction. Here are 5 red flags. I worked with some of the top PE practitioners as a BigLaw lawyer. They were sharp, strategic, and ruthless. The great ones develop a keen sense for reading people. They quickly bring serious people closer and identify red flags to distance from unserious people. Here are 5 red flags I have found to steer clear of people who will derail your transaction: First, it is critical to identify these people early. They engage in risky and counterproductive behavior and their proximity will cause collateral damage. While each one in itself is not a deal-breaker, it should set off alarm bells: 1. Dishonesty. Blatant dishonesty will usually not present immediatly. However, small dishonesties do. If a story seems like a stretch, unfounded assertions are made, or numbers are exaggerated - this is the number 1 correlation with disastrous results. Go back and read my Private Equity Story Time: Fraud and A Lynx Farm (posted: 11.9.24); there were signs of dishonesty, Buyer ignored them, and ended up buying a nightmare deal. 2. Dunning-Kruger Zone. There is a famous study showing that those who know almost nothing about a topic overestimated their intelligence and think they know everything, while those truly knowledgeable know what they do not know. I see this a lot and it is correlated with trouble. Serious people may be knowledgeable in some areas, but have the modesty to know what they do not know. People who think they know everything will blunder into bad deals and make bad decisions all the while thinking they are the smartest person in the room. On a prior deal, a Seller fired his M&A Advisor because he knew more than him. It cost him millions of dollars and I am not sure he even knows how much he lost. 3. Habitual Line Crossers. These people do not respect lines or boundaries in business or otherwise. Eventually, they step on a land mine and you do not want to be near them when they do. 4. Ultra-Self-Focused. We live in an individualistic society and I think it is good to focus on our interests. Skyscrapers are built, roads are paved, and people rise out of poverty due to capitalist individualism. It has brought the most good to the most people of any other system. However, in M&A, people have to care for other's needs as well as their own. If a person consistently puts themself first, it is a red flag. I represented a sponsor group (three partners) and one of them called me with a nefarious scheme to take equity from the others after closing. 5. Every Last Dollar Guy. Some people believe in zero-sum business. They will grab every last dollar, then reach into your pocket to grab yours. These people are tiresome and their incessant focus on the pennies deprives them of dollars. After closing hundreds of M&A deals (over $40 billion) and interacting with tons of people, these are the red flags I try to protect against.

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

After 25+ years in recruitment, I'm sharing the manipulation tactics some recruiters use to pressure candidates into hasty decisions - and how to protect yourself.   1. Artificial Urgency: "This offer expires tomorrow" - Ask for justification of the timeline and request reasonable consideration time. 2. False Exclusivity: "You're our top choice" - Inquire about the selection process and how many candidates are being considered. 3. Negotiation Shutdown: "The salary isn't negotiable" - Everything in business is negotiable. Explore total compensation package options. 4. Competitive Pressure: "Other candidates are willing to take less" - Focus on your value proposition rather than external comparisons. 5. Scarcity Manufacturing: "This is a unique opportunity" - Research similar roles in the market to verify claims. 6. Information Control: Withholding salary ranges - Ask upfront and research market rates independently. 7. Professional Pressure: "We need someone who can start immediately" - Maintain professional notice periods regardless of pressure. 8. Good Cop/Bad Cop: "The hiring manager liked you, but..." - Request direct feedback and clear communication channels. 9. Vague Advancement Promises: "This role typically leads to quick promotion" - Ask for specific timelines and advancement criteria. 10. Competition Anxiety: "We're interviewing other candidates this week" - Focus on role fit rather than artificial competition.   Quality recruiters partner with candidates and provide transparent communication. Manipulative tactics indicate recruiters prioritizing placement speed over candidate fit.   Trust your instincts and take time for informed decision-making regardless of external pressure.   What recruiter tactics have you encountered that raised red flags?   Sign up to my newsletter for more corporate insights and truths here: https://lnkd.in/ei_uQjju   #deepalivyas #eliterecruiter #recruiter #recruitment #jobsearch #corporate #professionaladvice #candidateprotection #careerstrategist

"I walked away from a $20M Series A the day before signing. Best decision I ever made." A founder got cold feet about a VC deal and backed out at the last minute. It was a blessing. Six months later, he discovered that same VC had destroyed two other portfolio companies. Here's why trusting your gut can save your company. Everything looked perfect. Top-tier VC, $20M Series A, term sheet signed, lawyers working on docs. Then he had dinner with another founder from their portfolio. "How's working with [VC firm]?" "Dude, they're destroying us. Forced us to fire our engineering team. Revenue dropped 60%. They're pushing us toward an acqui-hire." He called his lawyer that night: "Kill the deal." Red flags the founder ignored early on: - VC repeatedly raised questions about potential CEO replacement during negotiations. Kept asking about scenarios in which the founder will step down. - Wanted "operating partners" installed day one - Kept talking about potentially merging with "similar portfolio companies" - Focused more on financials and operations than product-market fit The gut check: Do they want YOUR vision or their vision? Are they backing you or replacing you? Would you want to work FOR these people? How it ended - He raised $5M from angels, grew to $15M revenue, sold for >$200M. The VC firm? two more portfolio companies failed the next year. Sometimes the best deal is the one you walk away from. Your gut knows when something feels wrong. A smaller check from the right investor massively beats a big check from the wrong one. #Founders #VentureCapital #RedFlags

One-sided contracts are the ultimate negotiation trap—throwing out an anchor so extreme, it drags every term into a sea of redlines. Here's how to tell if your contract setting off a chain reaction of redlines. I just reviewed a contract that all but guaranteed I’d have to push back. Some agreements try to be fair—this one didn’t even pretend. 🚩 One-sided termination for cause. 🚩 Actually, one-sided all boilerplate. 🚩 Insurance 500x the deal value. 🚩 No liability caps or meaningful limitations. 🚩 Indemnification for everything that could possibly happen. I tried to skim through it at first. But the moment I caught something unreasonable, I had to flag it. And once I started, I couldn’t stop. If they didn’t negotiate fairly on liability, what else was buried in here? I kept reading—and kept marking things up. The "anchoring effect" is a powerful force in contract negotiations—when you throw out extreme terms, your counterparty often responds with similarly extreme demands, setting off a cycle of redlines. At Pincites, we track how often contract language gets pushback, and we see this all the time. One redline leads to another, then another. And when that happens? 🔹 The deal drags out 🔹 Trust erodes 🔹 Some deals don’t close at all Contracts should be drafted to minimize redlines—not expect them. A contract that’s adversarial by design wastes time, legal resources, and goodwill. If you want to avoid unnecessary redlines, don’t give your counterparty a reason to pick up the red pen in the first place. If you’re losing 90% of the time on key terms, it’s time for a change. And at Pincites, we can tell you exactly where to start.

If a VC has been "reviewing" your deck for three weeks, you're not imagining it. They're probably stringing you along. There’s a few reasons VCs do this… For one, FOMO is real. VCs are terrified of passing on the next unicorn, so they’ll keep you warm "just in case," even when they're not excited. Second, they want to see who else is interested before committing. If other VCs are circling, suddenly you become attractive. And lastly, even if one partner loves you, they probably need to convince others who've never met you. The result is fundraising purgatory while they think about it. Here’s how to tell if you’re being strung along: ✅ Green flags: They ask specific follow-up questions, want to meet your team, mention timelines, respond within 1-3 days. 🚩 Red flags: Generic responses, weeks of silence followed by "still reviewing," avoiding direct questions, asking for more info without moving forward. If you're seeing red flags, it's time to push for clarity. Don't ask "What's your timeline?" Instead, share yours: "We're aiming to close our round in the next two weeks. Would that work with your process?" This creates urgency without being demanding. My favorite approach: "We'd love to know if you see a path forward so we can plan accordingly." Direct but not confrontational. One founder we know was getting strung along for six weeks by a "very interested" VC. Finally, they sent this: "Hi [Partner], I really appreciate the time you've spent on our deal. We're planning to close next week with our current investors. If there's still interest on your end, it would be great to know by Thursday so we can include you. If not, no worries at all." The VC responded within hours with a clear "no" and referred them to another fund that ended up leading the round. Sometimes the best outcome is just getting clarity.

I spoke with an investor (who’s acquired $100,000,000+ worth of real estate) about seller red flags. Here’s what he told me: 1. The seller inflates the true income of the property. 2. The seller is slow to provide adequate financials. 3. The seller doesn’t share necessary capex items. 4. The seller hides expenses in vague P&L lines. 5. The seller provides materially important info. ↳ Only AFTER you are under contract.  6. The seller states there are improvements. ↳ But has no record of said improvements. 7. The seller hasn’t prepared an OM. BONUS: 8. While you’re walking the property, tenants come up to you to complain about the landlord. If you’re acquiring real estate, understand the red flags that could blow up a deal.