Importance of Follow-Up Questions in Negotiation

Here's exactly how I structure my follow-ups to stop deals from slipping or ghosting at the last minute. Buyers ask themselves 5 crucial questions before they spend money. So we match our follow ups to each different question of the buying journey. The questions: 1/ "Do we Have a Problem or Goal that we Urgently need help with?" Follow up examples: Thought Leadership emphasizing the size / importance of the problem. Things like articles from Forbes, McKinsey, HBR or an industry specific publication. Screenshots, summations or info-graphics. NOT LINKS. No one reads them. 2/ "What's out there to Solve the Problem? How do Vendors differ?" Follow up examples: Sample RFP templates with pre-filled criteria. Easy to read buying guides. Especially if written by a 3rd party. 3/ "What Exactly do we need this Solution to do? Who do we feel good about?" Follow up examples: 3 bullets of criteria your Buyers commonly use during evaluations (especially differentiators.) Here's example wording I've used at UserGems 💎: "Thought you might find it helpful to see how other companies have evaluated tools to track their past champions. Their criteria are usually: *Data quality & ROI potential *Security (SOC2 type 2 and GDPR) *How easy or hard is it to take action: set up/training, automation, playbooks Cheers!" 4/ "Is the Juice worth the Squeeze - both $$$ & Time?" Follow up examples: Screenshots of emails, texts or DMs from customers talking about easy set up. Love using ones like the Slack pictured here. Feels more organic and authentic than a marketing case study. 5/ "What's next? How will this get done?" Follow up examples: Visual timelines Introductions to the CSM/onboard team Custom/short videos from CSM leadership When we tailor our follow ups to answer the questions our Buyers are asking themselves - Even (especially!) the subconscious ones Our sales cycles can be smoother, faster and easier to forecast. Buyer Experience > Sales Stages What's your best advice for how to follow up? ps - If you liked this breakdown, join 6,000+ other sellers getting value from my newsletter. Details on my website!

𝗪𝗵𝘆 𝘁𝗵𝗲 𝗯𝗲𝘀𝘁 𝗚𝗖𝘀 𝘀𝗲𝗻𝗱 𝗺𝗼𝗿𝗲 𝗳𝗼𝗹𝗹𝗼𝘄-𝘂𝗽 𝗲𝗺𝗮𝗶𝗹𝘀 𝘁𝗵𝗮𝗻 𝗮𝗻𝘆𝗼𝗻𝗲 𝗲𝗹𝘀𝗲 The best General Counsels I know share one deceptively simple habit: they make sure no important conversation ends without everyone clear on what was decided, why it matters, and what happens next. Sounds obvious, but it rarely happens in practice. In high-stakes settings (board calls, investment committee meetings, negotiations), the speed of discussion and the flood of detail leave plenty of room for different interpretations. Small gaps become big problems when the CFO thinks “we approved in principle” and the GC thinks “we signed off.” I've seen this at portfolio companies. In one deal review, the leadership team left with three different views of the next step. The GC didn’t wait for the confusion to surface. Before the day ended, she sent a concise note: here’s what we agreed, here’s the rationale, here’s what’s needed by Friday. That quick follow-up prevented weeks of misaligned work. 𝗪𝗵𝘆 𝘁𝗵𝗶𝘀 𝗮𝗽𝗽𝗿𝗼𝗮𝗰𝗵 𝘄𝗼𝗿𝗸𝘀: • 𝗧𝗶𝗺𝗶𝗻𝗴: Follow-up happens while discussion is fresh • 𝗦𝗽𝗲𝗰𝗶𝗳𝗶𝗰𝗶𝘁𝘆: No vague summaries or filler • 𝗖𝗹𝗮𝗿𝗶𝘁𝘆: Just decisions, rationale, and next steps The payoff is more than avoiding mistakes. Over time, people start counting on the GC to be the one who closes the loop. That reliability builds influence. You become part of how decisions get made, not just someone consulted. In PE environments where speed and precision matter, this discipline is even more valuable. Board members and operating partners notice GCs who work this way. It signals strategic thinking that reaches beyond legal analysis into business execution. For GCs, it’s a skill you can practice tomorrow. For decision-makers hiring a GC, ask: “Walk me through how you make sure alignment is clear after complex leadership discussions.” Listen for process, not just outcomes. It may not be flashy, yet small habits build real influence. 𝘚𝘰𝘮𝘦𝘵𝘩𝘪𝘯𝘨 𝘵𝘰 𝘬𝘦𝘦𝘱 𝘪𝘯 𝘮𝘪𝘯𝘥 𝘸𝘩𝘦𝘯 𝘺𝘰𝘶 𝘵𝘩𝘪𝘯𝘬 𝘢𝘣𝘰𝘶𝘵 𝘵𝘩𝘦 𝘲𝘶𝘢𝘭𝘪𝘵𝘪𝘦𝘴 𝘺𝘰𝘶 𝘷𝘢𝘭𝘶𝘦 𝘮𝘰𝘴𝘵 𝘪𝘯 𝘺𝘰𝘶𝘳 𝘭𝘦𝘨𝘢𝘭 𝘭𝘦𝘢𝘥𝘦𝘳.

5 questions most of us nerds totally -F- up in the sales process   ->and what to ask instead<-   We show up with a proposal and slide straight into logic-mode: Here’s what’s wrong. Here’s what we recommend. Here’s the cost. Then we wonder why the deal stalls, gets ghosted, or dies in procurement hell. IMO we face strong economic headwinds this year. In tough economies, when budgets are tight and CFOs and business owners are trained to say no, we need more than a checklist and a smile. We need a conversation built on trust, pain, and tactical empathy. After 30+ years running MSPs, leading security programs, and guiding clients through compliance journeys, I’ve seen exactly where most of us blow it. Most of us are asking the wrong damn questions. “Do you have a budget for this?” Why it fails: It’s a trap. You get a fake number or get ghosted. Instead ask: “How have you handled these kinds of risks before when budget was tight?” This disarms, invites story, and reveals priorities. From my experience, this is one they can’t dodge without revealing intent. “Is this a priority for you right now?” Why it fails: Too easy to say “not really.” It gives them a clean exit. Instead ask: “What happens if nothing is done about this in the next 3 to 6 months?” Now they have to wrestle with the consequences. You’re helping them feel the pain & you're finally having a real conversation. “Do you want us to send over a proposal?” Why it fails: You’re asking for permission to do unpaid labor. It puts you in the vendor friend-zone. Admittedly, I still mess this one up. Instead ask: “Before I put anything on paper, what would have to be true for you to say yes to this?” You’re surfacing the unspoken. Their internal politics. The landmines and sacred cows. The truth. “Can we schedule a follow-up?” Why it fails: You’re chasing. They’re stalling. Instead ask: “What’s the best way to navigate next steps on your side so this doesn’t go dark?” This question does two things… earns respect and exposes process. If there’s no real urgency or champion, you’ll know and get to “no” quicker. “Would this solution work for you?” Why it fails: It's hypothetical. It invites a safe “maybe.” Instead ask: “It sounds like this solves the problem we talked about, so what would stop us from moving forward?” Now you’re into decision psychology. You're proactively surfacing resistance, before it blindsides you later. Stop selling. Start diagnosing.   Stop pitching. Start uncovering. Stop asking for permission. Start earning commitments. Compliance and security aren't technical problems, they're business risks wearing technical clothing. If you're not connecting your work to revenue protection, liability reduction, and sales velocity, you're making yourself optional. And optional gets cut in a recession. You want to win? Learn how to make your clients say:   ->“We can’t afford not to do this.” Hope this is helpful… #sales #ciso #security #compliance #msp

Your follow-up system decides whether you close deals or just “had good conversations.” The first message almost never closes the deal. It only starts the clock. What actually closes deals is what happens after the first message. Let’s break this down properly: 1. Follow-ups are not reminders. They are momentum. If someone didn’t reply, it usually means one of three things: - They were busy - The problem didn’t feel urgent yet * Your message didn’t connect to a live issue Silence is not rejection. It’s unfinished context. 2. A 3-step follow-up system beats random “just checking in” pings. A simple structure that works: Follow-up 1: Re-anchor the problem they care about Follow-up 2: Add proof or insight (data, pattern, example) Follow-up 3: Create a clear decision moment No chasing. No begging. Just clarity. 3. Value-based follow-ups win because they reduce thinking, not add pressure. Bad follow-ups ask for time. Good follow-ups save time. Instead of “Any update?” Use: “Teams like yours usually get stuck at X stage. Is this relevant right now?” That feels useful, not needy. 4. Consistency beats talent in sales follow-ups. The rep who follows up cleanly for 30 days will always beat the rep who sends one great message and disappears. Deals close when: Timing aligns Trust compounds The buyer feels guided, not chased That only happens with consistency. 5. Track replies, not ego metrics. Don’t track “sent messages.” Track: -Which follow-up gets replies -Which wording moves the deal forward -Which step creates objections That’s how systems improve. If your follow-ups are weak, your pipeline will lie to you. If your follow-ups are tight, sales starts compounding quietly in the background. Your follow-up system is not admin work. It’s your hidden sales team.

The Follow-up Dance Everyone wants the contract. Few master the follow-up. Here's what most do: Send the proposal. Wait three days. Send "Just checking in..." Repeat until ghosted. It's the dance of desperation, and your prospect can hear the music. But what if we've got it backwards? McDonald's follows up with "want fries with that?" Amazon follows up with "others also bought..." But you? You're following up with "did you see my proposal?" See the difference? One adds value. The other adds pressure. Your proposal isn't sitting unopened because they forgot about it. It's sitting unopened because you haven't given them a reason to open it. The real follow-up isn't about the contract at all. It's about continuing to be useful. To be interesting. To be worth paying attention to. Share an insight about their industry. Point out a competitor's misstep. Send an article that makes them think. Because the best follow-up isn't a follow-up at all. It's leadership. Formula for Contract Follow-Up: 1. Acknowledge the pain of change: Empathize with the challenges or effort involved. 2. Contextualize the cost of inaction (COI): Connect the delay to tangible consequences, framed in the present. 3. Reframe the obstacle: Make the “enemy” external (e.g., a roadblock, not them). 4. Invite honesty: Create a safe space to hear the real status, including bad news. 3 Messaging Formats 1. Concise & Direct Subject: Are we hitting a roadblock? Hi [Name], You’ve been instrumental in getting this proposal to the finish line, and I truly appreciate the effort. I know [specific COI, e.g., “every week of delay keeps X revenue off the table”]. Has something unexpected come up that’s holding back the final signature? I’d rather know where we stand so we can adapt as needed. Let me know. [Your Name] 2. Empathetic & Collaborative Subject: Checking in on the proposal Hi [Name], I know this process isn’t easy—you’ve been a champion working through the details, and I appreciate it. That said, we’re seeing [specific COI, e.g., “the impact of [X issue] creeping into next quarter”]. Is there an unexpected roadblock we need to address together to move things forward? Or has something else shifted? Happy to adjust if needed—just let me know where we stand. Best, [Your Name] 3. Narrative & Storytelling Subject: Getting ahead of status quo losses Hi [Name], I can imagine how grueling contract reviews can be—it's one of the least glamorous but most critical steps. It got me thinking about [specific COI, e.g., “how $2M slipped through the cracks last year due to the status quo”]. Have we run into an unexpected roadblock that might risk a similar outcome this time around? It’s okay if we’re stuck—I just want to make sure we can keep the momentum toward solving [specific pain point or goal]. [Your Name] ___________ When was the last time your follow-up made someone smarter?

I just reviewed a follow up email that made me want to delete my LinkedIn account. After an incredible discovery call where the rep: → Uncovered $500K in annual losses → Identified specific pain points → Built genuine rapport with the prospect He sent this follow up: "Hi John, following up on our conversation. Any thoughts on next steps?" I'm not joking. That was the entire email. This rep went from trusted advisor to desperate vendor in one sentence. Here's what he should have sent instead: "John, Based on our conversation about the $500K you're losing annually due to deployment delays, I've put together a brief overview of how we've helped similar companies reduce this impact by 80%. Given the scope of this challenge, when can we get your CFO involved to discuss the business case? Best regards, [Rep name]" The difference is night and day: ❌ Weak follow up: "Any thoughts on next steps?" ✅ Strong follow up: References specific problem + demonstrates value + advances the sale Your follow up emails should sell, not beg. Every touchpoint is an opportunity to: → Reinforce the problems you uncovered → Show how you solve them → Move the deal forward Stop wasting these golden opportunities with generic, desperate sounding messages. Use what you learned in discovery to craft follow-ups that advance the sale. Your prospects are drowning in "just checking in" emails. Be the one who stands out by referencing real business impact. — Reps! Here’s 5 simple follow up strategies to close seals faster and to minimize ghosting: https://lnkd.in/gJRJwzsN

We’d love a decision by tomorrow.” That’s what the Meta recruiter said after sharing the offer. But here’s the thing: → You don’t owe an answer on the spot. → And trying to negotiate too soon — without leverage or prep — can backfire. Here’s how to handle moments like this instead: 1/ Hold the pause → When the recruiter shared numbers and then asked, “Any reaction?” The candidate waited. That small silence? It prompted the recruiter to keep talking — and reveal more about how comp moves at Meta (hint: equity is more flexible than base). 2/ Ask targeted follow-ups → “Could you explain the difference in flexibility between base and equity?” → “Is that $500k equity number a range, or something contingent on other offers?” You don’t need full answers. The goal is to gather context — not corner them. 3/ Push timelines with credibility Instead of saying: “I can’t decide that fast.” Say this: “I understand the team wants to move quickly — and I want to support that. But how can I make a life-changing decision in 24 hours?” Frame your ask around thoughtful consideration, not delay. This isn’t about playing hard to get. It’s about being clear-eyed, warm, and strategic — especially when the pressure’s on. Have you ever been asked to make a big decision fast? How did you handle it?

AE: I've sent 5 follow-up emails and nothing. Me: When did you last pick up the phone? AE: Two weeks ago. Me: There's your problem. Phone follow-ups close 3x faster than email-only sequences. AE: That feels desperate when they're not responding. Me: You've got it backwards. Professional buyers expect follow-up calls after missed commitments. Not calling signals you don't believe in your own deal. Here's what actually happens with persistence: First call - 11% callback rate. Second call - 22% callback rate. Third call - 33% callback rate. Your callback odds literally triple, but most reps quit after attempt one. AE: So I should call three times? Me: Within specific windows. Call within 24 hours of their missed date. Script: "We had [decision] targeted for Friday. Confirming whether we're moving ahead, adjusting scope, or closing this out for now." Not asking for favors. Asking for clarity on their commitment. AE: What if there’s no answer? Me: 80% won't pick up. Leave a 12-second voicemail with the same message. Then email three sentences: their stated goal, the specific outcome you deliver, two time slots. Second attempt 48 hours later with new info - a metric, case study, or insight. Third attempt in a different time window. Then pause for two weeks. AE: Why does email fail where calling works? Me: Email lets them hide. The phone forces resolution. When someone commits to a date then misses it, they're either struggling with internal alignment, got blindsided by another priority, or lost conviction. Email lets them avoid the awkwardness. Calling surfaces which one. You either unlock the real blocker or kill a dead deal. Both are wins. AE: This contradicts everything I've been taught about being respectful… Me: One AE I know avoided calls completely. Started dialing daily using this exact system. Closed 5 deals from follow-ups alone… two on the last day of the month. It takes an average of 8 touches to book a meeting, but most reps treat touch 2 like it's touch 20. The math is simple: triple your callback rate or keep wondering why deals die. AE: When do I stop? Me: After three calls with no response, pause two weeks unless you see a trigger event. But most will respond by call two because you're calling about their timeline, not yours.

"Is that a showstopper for you?" This is one of the most valuable questions I've ever learned to ask during negotiations. Why? Because the answer, whether 'yes' or 'no,' provides crucial insights. And insight is what you need most during a negotiation. I've found this question useful in various contexts, from hiring to acquisitions. Example: I was in the process of hiring someone but was constrained by a tight budget. I offered a salary range of X, and the candidate countered with Y. So I asked, "Is that a showstopper for you?" The implications of their answer are significant: 👎 If it is a showstopper: We both save time, recognizing that there isn't a fit. Alternatively, it forces us to approach the issue from a different perspective. (Assuming the range was also a showstopper for me.) 👍 If it's not a showstopper: The conversation advances, allowing us to focus on other essential factors. 👉 Pro Tip: After asking the question, be quiet and let the other party think and respond. The ensuing silence might be uncomfortable, but the insights gained are invaluable. Good luck!

When negotiating with adjusters, I frequently talk about life in general. If my child is sick, for example, I’ll tell them. Similarly, I ask them how they are and take detailed notes about what they say. If they tell me something personal about their life, I want to remember it. Then, in later conversations, I’ll follow up. How’s your family? Is your spouse doing ok? Your parents go through the surgery alright? Sometimes I believe they’re surprised I remember such things. But, it’s critically important to do such, both for the case, but also for being a good person. These types of conversations allow connection on the human level. They create spontaneous opportunities to develop relationships and make for a better experience instead of simply arguing back and forth. Moreover, if you connect on the human level, you’re seen as a friend, not an enemy. You’re one of them, not the opposition. And if you’re a friend, well that’s someone they’re willing to go to bat for to get a case settled when they need to evaluate or seek more authority.