How to Create Urgency in Sales: Ask More Questions

Great sales isn’t just about the product but it’s about digging deep to uncover the real pain points. Genuine curiosity is what transforms a pitch into a meaningful solution.

Sales metrics used to feel extremely confusing. Until Mark Kosoglow showed me how to actually use them. Like a lot of managers, my team sometimes struggled to book meetings. So I tried a bunch of things to fix it - new email campaigns, different outreach times, dedicated time blocks for prospecting. We eventually found it was an activity problem, but I cringe thinking back to it because I spent so much time fixing problems I didn’t even have. Here’s the truth: when something like “meetings booked” goes down, it could be for ten different reasons. Activity. Messaging. Timing. Without a framework to help identify the root cause issues of your sales process, you’re just guessing at what to fix. That’s where Mark’s L1 & L2 metrics come into play. Here’s how they work: 𝗦𝘁𝗲𝗽 𝟭: 𝗨𝘀𝗲 𝗟𝟭 𝗺𝗲𝘁𝗿𝗶𝗰𝘀 𝘁𝗼 𝗳𝗶𝗻𝗱 𝘄𝗵𝗮𝘁’𝘀 𝗯𝗿𝗼𝗸𝗲𝗻 𝗶𝗻 𝘆𝗼𝘂𝗿 𝘀𝗮𝗹𝗲𝘀 𝗽𝗿𝗼𝗰𝗲𝘀𝘀.  L1 metrics are things like meetings booked and S1-S2 conversion. Once you find an underperforming metric, move to the next step. 𝗦𝘁𝗲𝗽 𝟮: 𝗗𝗿𝗶𝗹𝗹 𝗱𝗼𝘄𝗻 𝗶𝗻𝘁𝗼 𝗟𝟮 𝗺𝗲𝘁𝗿𝗶𝗰𝘀 𝘁𝗼 𝘀𝗵𝗼𝘄 𝘄𝗵𝘆 𝘁𝗵𝗲 𝗟𝟭 𝗺𝗲𝘁𝗿𝗶𝗰 𝗶𝘀 𝗯𝗿𝗼𝗸𝗲𝗻. Let’s say meetings booked (L1) are down. Stack rank the reasons why they could be down and look for underperforming data. Those reasons are your L2 metrics. So if your team hasn't been sending many emails, then your meetings booked issue is likely due to a lack of activity (not messaging, not timing). So start by fixing that. If something in your sales process isn't broken, don’t fix it. Instead, use L1 & L2 metrics to identify your actual issues quickly. That's a lesson that would've save me a ton of time and a lot of headache. Want the full breakdown? Check out the newsletter under my name — I walk through the exact metrics Mark’s used his whole career to diagnose sales process problems fast.

Sales is harder today. Not because reps suddenly got worse, but because the game changed. Your buyer already knows what they want. They’ve done the research. They’ve compared competitors. They’ve already narrowed the shortlist before you ever reach out. That means every moment of outreach has to count. Here’s what still makes sales easier, or at least, more winnable: 1️⃣ Preparation Know the customer inside and out. Use AI, use data, use intent signals. The rep that shows up most informed wins. 2️⃣ Personalization Generic outreach is invisible. Tailored messages that speak to their goals and pain points break through. 3️⃣ Effort The reps who are all in on their product and all in on their customer will always outperform. 4️⃣ Consistency These behaviors are controllable. Doing them every day is the difference between one great quarter and a great career. 5️⃣ Human connection People still buy from people. Building trust isn’t a soft skill, it’s a competitive advantage. 6️⃣ Courageous conversations Asking hard questions reveals truth. And truth wins deals. 7️⃣ Always be closing Not in the old-school sense. Always be learning. Always be progressing the deal forward. The challenge is that data doesn’t always capture these things. CRMs track activity and pipeline velocity, but not authenticity, tone, or trust. Those are qualitative signals that decide who wins and who doesn’t. That’s why conversational analytics and qualitative AI matter now more than ever. RevOps and Sales Ops teams are moving past dashboards. They’re starting to decode what happens inside the conversation, the words, tone, confidence, empathy, and clarity that separate average reps from elite ones. But there’s another layer that matters just as much - process. RevOps and Sales Ops teams must focus on process analysis. Reps should spend the majority of their time doing what they do best. Selling. If processes are manual or clunky, they become blockers. The goal is simple: provide the most help to each rep without them lifting a finger. Help them prepare faster. Help them stay accurate. Help them get to impact quicker. And above all, automate the repetitive tasks that steal time. Give hours back to sellers, managers, and enablement so they can focus on what drives outcomes - curating, coaching, and developing the strongest, most impactful sellers possible. Because sales success comes down to two things: The quality of the conversation, and the efficiency of the system behind it. Quantitative data tells you what happened. Conversational data tells you why. Operational design determines how fast you can improve both. The teams who figure that out first will own the next era of growth.

Why a Sales System is Essential When Selling a Solution or a product? In business, especially when selling solutions rather than simple products, success rarely happens by accident. It’s built on repeatable processes that create trust, move prospects through a journey, and turn interest into action. That’s where a sales system comes in. Whether you’re offering marketing services, consulting, software, or any tailored solution, a well-structured sales system is the backbone that supports growth and profitability. Without it, even the best offers can fall flat. 1. Consistency Builds Predictability A sales system ensures that every potential client has a consistent experience. From the first touchpoint to the signed agreement, you’re not leaving things to chance. This consistency allows you to forecast results, plan resources, and scale without the chaos of unpredictable sales. 2. Educates and Builds Confidence Selling a solution often means solving complex problems. Prospects may need education to truly understand the value you bring. A well-designed sales process guides them step-by-step — helping them identify their pain points, see the benefits of change, and trust that you’re the right partner to deliver it. 3. Identifies Bottlenecks and Opportunities A system isn’t just a script or a checklist — it’s a measurable framework. Tracking each stage (leads, booked calls, proposals, closes) reveals exactly where deals are stalling and what’s driving success. This data gives you the insight to refine and improve, rather than relying on guesswork. 4. Enables Scalability If your sales success depends solely on you, your growth has a ceiling. A documented sales system allows you to train team members to follow the same process, ensuring quality stays high while you focus on strategy, delivery, or expansion. 5. Protects Against Lost Opportunities Without a structured process, follow-ups get missed, leads grow cold, and high-value opportunities slip away. A strong sales system includes lead nurturing and timely follow-ups so that prospects stay engaged until they’re ready to commit. The Bottom Line When you sell a solution, you’re not just selling a product — you’re selling trust, clarity, and confidence. A sales system ensures that trust is built every time, results are measurable, and growth is sustainable. Before scaling your marketing or investing heavily in ads, make sure your sales system is in place. Advertising can bring people to your door — but it’s your sales process that gets them to step inside. #SalesStrategy #BusinessGrowth #LeadNurturing #CustomerJourney #SalesProcess #TrustBuilding #DataDrivenSales #ScalableSolutions #SalesSuccess #ClientEngagement

If you don’t constantly review your sales process & the way it flows, you’re probably missing revenue as it leaks out the sides of your funnel. Sales really is a numbers game. When you start to observe the way your pipeline breaths, you’ll see there are tweaks you can make to throttle percentages (%) within each stage. These small changes can have big impact on your overall conversion rate as a rep. In most b2b sales it generally looks something like 1) find company that fits ICP, figure out who to reach out 2) a certain % of those folks will actually pick up/answer 3) reply is a positive response 4) book an appointment to learn more  5) If interested, review a proposal  6) sign a deal But look deeper into what logically happens in-between each of those steps. factor in any internal decision making that might string sales from your pipeline. And how many deals are ghosting/falling off after you send out contracts. Is your data clean on the top & targeted to the right DMs? If not, all of your down-funnel metrics will suffer. Where do your reps source their data? — As a rep - think about how much you want to make every month & work backwards to see how many top of funnel actions you need to achieve that number. once you have those numbers, figure out how to decrease the number of prospects you need in the top of funnel to hit those same goals. ask yourself “where am I leaking revenue in my day-to-day”. The best salesfolks funnels look more like cylinders. 

Sometimes a deal looks fine in the CRM, but when you actually listen to the calls, it’s clear it’s not going anywhere. I’ve seen reps keep chasing when the signs are right there. Like when the buyer stops asking questions. No curiosity, no concerns. Just polite nodding. That usually means they’ve already moved on, even if they haven’t said it yet. Or when the person says, “I’m the decision maker,” but they’re not high enough up. They always answer the phone. Always reply. But they won’t loop in anyone else. That’s usually a no po, no power. And you can waste months there. And sometimes it just feels too easy. No friction, no objections. The rep walks away thinking it went great. But in enterprise sales, that’s rarely how good deals sound. The ones that close usually come with questions, pushback, even a little tension. That’s what it sounds like when the deal actually matters to them. When you're reviewing calls, what signals tell you the deal isn’t real?

Top 5 Reasons Your Sales Pipeline Slows (And They’re Not in Your CRM). In industrial markets, sales cycles are long. You expect technical hurdles, budget reviews, and pilot delays. But some of the most frustrating blockers aren’t strategic, they’re human. After 30+ years working on tech commercialization and industrial sales, I’ve seen many strong deals stall, not because the product wasn’t right, or the ROI wasn’t there, but because of disruption inside the customer’s own business. Here are the Top 5 unexpected, but all too common, reasons sales deals stall, and how to manage them: 1) Your Champion Leaves the Business - It happens all the time. You’ve spent months building a relationship, and then your main contact quits or moves roles. If you’ve only built one relationship, the deal goes cold. Fix: Always build a network. Engage at least 2–3 stakeholders across functions early. 2) Key People Go on Holiday or Parental Leave - It sounds small, but we’ve seen six-figure deals stall for months because a decision-maker went away for the summer. Fix: Get timelines agreed upfront. Ask “Who else can move this forward if you're out?” 3) The Company Reorganizes Mid-Cycle - New leadership, budget freezes, new priorities, it’s easy for your deal to get de-prioritized during change. Fix: Keep conversations linked to strategic outcomes. Make sure your solution aligns with multiple business goals, not just one initiative. 4) Procurement Delays You Didn’t See Coming - Even after technical approval, procurement can slow things down, especially in larger firms. Fix: Map the buying process early. Ask direct questions: “What’s the approval path?” “What’s the typical timeline?” “Who signs?” 5) Internal Confusion on Ownership - Sometimes deals stall because no one inside the customer actually ‘owns’ the next step. Sales, engineering, procurement, they’re all waiting for someone else. Fix: Be proactive in facilitating ownership. Offer to co-create implementation plans or assign pilot responsibilities. Sales and strategy often fail, not because the idea is wrong, but because we forget we’re dealing with real people, under pressure, with limited time and conflicting agendas. These delays are rarely personal, but without planning for them, they can derail months of progress. Great sales execution isn’t just about moving fast, it’s about keeping momentum when things slow down. TTIP Global Jim Hick | Andreas Sonntag | Cliff Spiro #TTIPStrategy #SalesExecution #IndustrialSales #DeepTech #CustomerEngagement #B2BGrowth #ScaleUp

15 Uncommon Sales Truths — Advice nobody told you (but should) Fresh, research-backed, and a little contrarian — here are 15 practical truths that most salespeople never hear, with one clear action you can take for each. 1. Sell the problem’s cost, not the product’s features. People buy to avoid pain or gain time/money. Quantify the ongoing cost of doing nothing and make that the focal metric. Action: For your top 5 prospects, write a one-line “cost of inaction” in currency or hours/week. 2. Your single best prospect is the person who once said “no.” A thoughtful “no” reveals objections and boundaries — and doubles as a consent to continue the conversation if handled right. Action: Revisit three past “nos” and send one insight or update that directly answers their objection. 3. Silence is a probing tool — not an awkward gap. Pauses let prospects reveal unguarded info and show you’re listening for meaning, not just waiting to sell. Action: In your next call, intentionally pause for 4–6 seconds after a key question and write what you learned. 4. Measure outcomes the buyer cares about — then report them back. If your KPI is demos booked but the buyer cares about retention, you look misaligned. Mirror their success metrics. Action: Ask every decision-maker: “If this succeeds, what metric will you show your boss?” Record it. 5. Treat your sales funnel like an investment portfolio. Diversify prospect types (fast-close, enterprise, referral leads) and size positions to balance risk and runway. Action: Categorize your pipeline into three risk buckets and rebalance until no bucket >60% of total value. 6. Create a “reciprocity ledger.” Track small value you’ve given each contact (intro, insight, report); it’s the invisible equity you can call on later. Action: Add a short note to three CRM contacts today saying what value you gave and when. 7. Pre-mortem every deal before you pitch it. Imagine the deal failed — list five realistic reasons why. Fix those before the next conversation. Action: Do a 5-minute pre-mortem for your largest open opportunity. 8. Use “micro-commitments” to avoid fence-sitting. Large yes/no asks cause paralysis. Replace them with tiny, no-pressure commitments that build momentum. Action: Replace one “Will you buy?” moment with “Can I send two options for you to compare by Thursday?” 9. Practice radical transparency on pricing psychology. Break pricing into choices and context: show the anchor, the popular choice, and what each option actually delivers. Action: Reframe one pricing conversation with a three-option layout and label the “most popular” one. 10. Track emotional temperature, not just lead score. A high lead score with low emotional warmth is fragile. Note tone, urgency, and trust signals alongside numeric scores. Action: Add a one-line “emotional temperature” (cold/warm/hot) to 5 CRM records and act accordingly. Check comment section for the others. cheers #salestips #sales #directorofsales

As A.I. evolves, it’s not just changing how sales teams work, it’s redefining who does the work. Our new report dives deep into the emergence of agentic A.I. in B2B sales: intelligent, proactive A.I. agents that don’t just assist sellers, they act on their behalf. Here’s a breakdown of the key insights. - A.I. Is Sales Strategic Edge Best sellers are already leveraging A.I. agents & sales leaders recognize their transformative potential. Agentic A.I. is no longer experimental, it’s a competitive advantage driving sales success, especially amid economic challenges. A.I. agents help automate complex tasks, freeing top performers to focus on closing deals & building trust. LinkedIn & Ipsos research shows this shift is happening now. - Sales Teams Are Entering the Age of the A.I. Agent The next leap is Agentic A.I., autonomous tools that act on behalf of sellers. Agentic A.I. proactively prioritizes leads, crafts outreach, schedules meetings & advances deals with minimal direction. This autonomy reduces administrative tasks, letting sellers concentrate on closing rather than clicking. - Best Performers See the Future & It’s Agentic Our survey breaks down seller attitudes by quota attainment, showing high performers are much more open to A.I. agents. - Agents for the Prep, Humans for the Pitch Sellers feel most comfortable using agentic A.I. for early-stage tasks like lead identification, account research, prioritization & drafting outreach. Confidence drops for client-facing tasks such as sending emails without review, managing conversations & making calls. - The Agentic AI Payoff for Sales Leaders Leaders seek more than automation, they want to transform sales with smarter insights, better decisions & fuller use of CRM data. Their goal is to build an intelligent, adaptable sales engine that drives success in today’s fast-paced market. Navigating Agent Adoption Challenges - Sales leaders see agentic A.I. as a path to smarter selling, better insights, & faster revenue but adoption requires more than technology; it demands a mindset shift. Successful implementation depends on trust, confidence in data & responsible change management with human oversight. - Choosing the Right A.I. Partner Agentic A.I. success depends on quality data & models; sales teams must avoid scaling ineffective tactics amid low buyer trust. LinkedIn Sales Navigator will soon launch Sales Assistant, an AI-powered tool delivering personalized daily leads with real-time signals, insights & outreach tips. It combines intent data with LinkedIn’s vast network to identify decision-makers, suggest tailored messaging & adapt to each seller’s style, saving time & boosting effective, personalized outreach. Conclusion: Navigate the Future of Sales with Agentic A.I. The sales teams that adopt it thoughtfully, with strong partners & ethical practices, will lead the next era of B2B selling. Companies already investing in AI are reporting revenue gains, proving the payoff is real.

The Modern Sales Loop A repeatable system every sales leader needs to convert faster. The truth? Most sales teams don’t need more tools. They need better systems. Because today’s buyers are smarter, faster  and harder to impress. Here’s how top performers close faster without chasing harder 1️⃣ Understand Today’s Buyer (Research) — Study how your audience makes decisions — Identify pain points before the first call — Know what builds trust  and what kills it — Stay sharp on trends and competitors You can’t influence what you don’t understand. 2️⃣ Redefine Your Pitch (Reframe)  — Stop pushing features  sell outcomes — Tailor every message to the buyer’s world — Lead with insights, not product talk — Speak in results, not jargon Buyers don’t buy what you sell. They buy what it does for them. 3️⃣ Engage with Intent (Connect) — Ask questions that reveal real needs — Listen 70%, talk 30% — Personalize every touchpoint  email, call, demo — Make them feel understood, not targeted People buy from those who get them. 4️⃣ Guide, Don’t Pressure (Advise) — Position yourself as a trusted advisor — Back every suggestion with data — Focus on solving, not closing — Build mutual commitment, not quick wins Pressure closes deals. Guidance builds partnerships. 5️⃣ Measure, Learn, Repeat (Optimize) — Track what messaging actually converts — Review each loss  learn why — Refine your pitch every cycle — Repeat the loop  buyers evolve constantly Each loop makes you sharper, faster, harder to replace. Remember this: The best salespeople don’t chase. They guide. They teach. They loop. Modernize your pitch. Speak your buyer’s language. Close with confidence. If this resonated, share it with your team. Follow Andrew Wright for more insights on modern sales & marketing. Get your copy of my new book: 11 phrases that kill deals (and what to say instead): https://shorturl.at/QVOyY