How to Identify and Address Prospect Pain Points

Marketing to target accounts isn't about you. It's about solving their real, messy, human problems. The number 1 reason marketing campaigns fail? They're all about “us” when they should be about “them”. I see it every day; campaigns obsessing over: 💬 "Our unique differentiators" 💬 "Our feature set" 💬 "Our market position" Meanwhile, your prospect is lying awake thinking: 👉 "My team is drowning in work" 👉 "Our project is completely stuck" 👉 "I'm not going to hit my targets" 👉 "Leadership is pressuring me and I can't deliver" 👉 "If we screw this up, I'm on the hook" You need to know them on a human level. Because if you miss their pain points, you're invisible. Ready to make it about them? Here's your playbook: 1. Talk like a peer, not a pitch deck → Replace "leverage" with "use", "utilize" with "try", "implement" with "set up". Strip away the corporate speak. Write like you're messaging a colleague. 2. Lead with their pain points → Start messages with "I know you're dealing with..." or "Many [job title] tell me they struggle with..." Show you understand their world before pitching yours. 3. Focus on specific situations, not generic personas → Instead of “VPs at enterprise companies", try “Sales VPs with “X“ goal". Context beats demographics. 4. Educate first, sell second → Share frameworks, templates, and lessons learned. Build a content library that helps them win “right now”, whether they buy or not. The sales conversations will follow. 5. Show up consistently → Enterprise deals take 6-18 months. Map out a year of helpful content. One great post won't cut it - you need to become their trusted guide through the journey. 🎤 Your best campaign won't sound like a brag. It'll sound like empathy. It'll sound like: "Been there. Tried that. Here's what actually works." Looking for some legend-level stories of closers. Share a line or tactic that turned empathy into pipeline. 👇 _______________ If this post resonated with you, I’d be grateful if you could like it and follow me Jennelle McGrath for more insights. And if you’re feeling generous, a repost would mean the world. If there is anything I can do to help you in your journey, please do not hesitate to DM me! Thank you so much! ❤️

My sales manager always lectured me to uncover problems and dig for pain. My problem was most of my prospects would come to me and talk about goals they had. They'd say things like: "We're looking for a more efficient accounting platform" "We have a goal to expand our brand awareness" "We need a way to process invoices more quickly" ___ I would get stuck because I didn't know how to turn goals into problems/pain. Eventually I learned that you just need to "flip" the goal the prospect shares with you on its head and inquire about the inverse of that goal. Sounds like: Prospect: "We're looking for a more efficient accounting platform" You: "Could you tell me about the ways your current accounting system isn't efficient enough?" OR Prospect: "We have a goal to expand our brand awareness" You: "Is that because you feel like folks don't know you exist today?" OR Prospect: "We need a way to process invoices more quickly" You: "Is that because invoices are not getting processed quickly enough?" ___ Behind every goal is a problem, it's up to you to unearth it.

Sales reps frequently ask me, "What if the prospect doesn't have any pain points or projects they need to do now? What do I do then?" People are motivated by 3 things: Fixing problems Accomplishing goals Avoiding risks --------- Doing this ski run called 'Banana' at Crested Butte has been a goal. Was it a 'need to have?' No. It was a 'nice to have.' So why do it? There was enough snow for ski patrol to open the gates. It was sunny. We were feeling good, so we navigated the nasty traverse over and dropped in. Now I can cross it off the list. Accomplishing almost any goal involves some risk. That was true here. Although with conditions like this, the risks were minimal. Unconsciously my brain determined that the pain of same (having not skied it) was greater than the pain of change (the risks of hitting rocks). When the pain of same > the pain of change = people take action --------- What does this have to do with sales? Most sales reps ask prospects questions about pain points. They ask questions about current projects or initiatives. They ask questions about headaches and frustrations. And all this is really good. Except sometimes your prospects don't have any problems. They think, "If it ain't broke, don't fix it." This is where you change your line of questions. "It's great to hear that you're not feeling the pain of managing your cloud side by side with on premises. Most of my customers are." "What's the next step for you? What goals do you want to accomplish in the next 6 months?" The prospect/customer talks. Hopefully you hear some goals that align with your products and services. In that case dig deeper, quantify the impact, and find out who else is involved. But what if they have no goals? Easy. Switch to questions about risk. "I know you've been doing a lot of preliminary work on using generative AI. Many of my customers are realizing that the hybrid cloud / on-prem infrastructure is not going to be effective once they move more parts of business processes to AI. How are you thinking about that infrastructure risk for the future?" Always try to find problems they need to fix first. People are going to be more motivated to buy a fire extinguisher if there's actually a fire happening. But if there isn't a fire happening, selling a fire extinguisher becomes a risk mitigation tool. Or accomplishing a safety goal. There won't be as much urgency, so sales cycle times will potentially be longer. But ultimately you're going to have way more opportunities in your pipeline if you're asking about goals and risks as opposed to just looking for problems. #salesenablement #askingquestions #salescoaching #salestraining #salescalls #salestips

When I was a VP of Sales, I had SMB AEs making $200K+ a year. These AEs were closing 50-70% of their demos. Here are 5 techniques I taught them that you can use (even if you're a MM or ENT AE): 1. SEEK PAIN: If you don't know the prospect's: a) pain b) size of pain c) who's impacted by that pain then what the hell will you demo? They would not demo the software until they find out the prospect's pain points. So one of the questions we started asking to get to this answer as quickly as possible was: "What specific challenges are you dealing with that you think we'd be able to help you with?" 2. REJECT PROSPECTS: SMB sales is a double edge sword. You can be 'stuck' with a lot of leads & deals. Many of those deals are not a fit. So they take up space and time in your calendar. Although very hard to do, I trained them to be comfortable rejecting a lead if it didn't seem like it would close within 90 days. 3. DEMO OUT OF ORDER: Most bad demos follows a predictable demo flow. First talk about X, then show them Y, then cover Z. But many times, prospects only had 1 specific problem they wanted to solve, nothing more. And if you showed them how to solve that 1 problem you'd win them over. So a feature that would typically be saved until the end of the call was showcased right away. 4. ASK PRQs: Digging deep on discovery is hard to do (also for MM and Enterprise). Average AEs try to pigeonhole all of their discovery questions in the beginning of the call. This pissed off prospects. Instead, we sprinkled questions throughout the demo using PRQs (Process Related Questions). For example, before showing a relevant feature, ask: "Curious, what's your current process of managing your invoices today?" 5. MICRO-CLOSE: I used think closing happens at the end of a sales call. But closing is really just the sum of 'micro-closes' you do throughout your demo. At the end of a relevant feature, the AEs would ask: "Does this solve your problem of [pain]?" If prospects say YES, the AEs just micro-closed them on that. Do this throughout the call and you're compounding your close. P.s. Every top AE I trained has mastered discovery. 6,000+ AEs are crushing their disco using these 24 questions: https://lnkd.in/eR69raD4

In Never Spilt The Difference, author Christopher Voss reveals a negotiation tool called "labeling." Here's how I use it to overcome hard conversations in sales and negotiations. This year, I've taken 367 sales calls.  Most go fine. But once I had a tense prospect who was resistant from the jump. • Short answers • Negative vibes • Cynical remarks I couldn't understand what was wrong. But instead of asking her, I "labeled" to uncover the truth: "Sally, it seems like you've had a bad experience with a sales guy before, is that right?" She burst into a story of her older brother, a salesman himself, who spoke of ripping money out of people's hands. And how she now associated salespeople with evil. But after my label the tension was gone... We even had a laugh about it. The reason this works so well is simple. According to Chris, "Labeling negative emotions diffuses them; labeling positives reinforces them." The formula is: "It seems like + [What you suspect] + is that right?" Ultimately, it helps you get to the truth, together, in a non confrontational way.    Hope your try it! Let me know how it works. P.S. Have you read this book? I was pretty put off by the title but found it to be a world class help.

Most salespeople try to skip the “good.” And that’s a damn shame. Because if you want to create real conversations that convert, you need to understand what your prospect likes before you try to fix what’s broken. Here’s what I mean: Let’s say you’re selling insurance. And the person you’re talking to already has an agent they work with. Most reps want to tell you why you should switch to them. "We've got better policies, better service and better people to take care of you," And jump in with, “Let me do a free quote and show you how we can save you money!” In other words, "You made a bad choice to go with that person. I'm better." But what does "better" even mean? I don't want to get jammed on price, but there are reasons I don't mind paying more than cheapest. Here’s the smarter way to approach this situation. The No B.S. Sales way. Start with what they like. Ask, “who are you working with right now?” Then compliment them on their choice. "Great company." Validate their decision. "I'm always curious about my competitors, what do you like best about what they do for you?" Then dig deeper. “Ok, What else?” "Yup, I've heard that about them. Keep going until they’ve laid it all out. Agree with them about all the good things they've said about your competition. And then, only then, ask the pivot question: “If there were one thing you wish were better or different, what would that be?” Their defenses will be down and they will be more likely to share. Be surprised when they come up with something. Then ask "what else?" Now you’ve got the door open. You’ve uncovered a pain point they gave you permission to explore. This is called the Good → Bad method. And it works because it respects the prospect’s experience. It’s not about selling harder. It’s about understanding deeper. So stop skipping the good. Lean into it. And earn the right to help. Want more No B.S. Sales lessons? Send me a DM and let’s have a conversation.

I've made a lot of mistakes on discovery calls that cost me deals. There's one mistake I've found that seemed to completely shift how the rest of the call went. The faster I uncovered this, the BETTER the call went. The single thing? My SPEED in uncovering the ROOT problem. I was simply taking too long to uncover the real problem when I first got started. This meant less time on the call to dive in deep. Less time to have them soak in the pain. And it meant surface-level responses that don't make the prospect think. Here are 10 simple questions you can use to get to the root problem fast: (I'm pretty direct so take these and adjust them to fit your style) • What sparked you to book a call today? • What's making this a priority now? • What are you currently doing to address (Problem)? • How's that been going? • What if 6 months go by and you're still dealing with (Problem)? • How does that impact you directly? • How does that impact your company? • Who else is impacted by this? • How are they impacted? • If (Problem) was solved, how would you measure it? If you bolt on follow-up questions that dive in deeper with each response... Watch your prospect go from CURIOUS... to COMMITTED. Share to help more AEs crush it 🔁