Lessons Learned From Unsuccessful Sales Calls

6/10 of our pitches used to fail, keeping me up at night until I learned a lesson that changed everything. You see, the majority of us who don't get a project even after pitching tend to shut down. Ignore the situation. Move on. So I started doing the opposite. I started calling the prospect who rejected us. Instead of moving on, I asked questions to understand why I wasn't selected. Mostly, we were the strongest contender, but we missed 1 crucial detail or the other. A conversation with a brand that rejected us changed my approach forever. So here's my so-called winning formula to use after every "no": • Get specific about who won and why • Understand the decision-making process • Learn how the project evolved after pitches • Uncover the hidden factors that played a role The most valuable insights were: - At times, it wasn't about our pitch at all - it was about how we presented our expertise. - Sometimes losing a pitch saved us from the wrong client fit. One prospect told us "we wanted something flashy." That rejection validated our premium positioning. - Most decisions are made in quiet conversations before and after. One prospect chose another agency because of a past relationship we never knew existed. - Projects often change shape after pitches. What starts as a full-service contract might split between multiple agencies or move in-house. Every "no" is a data point. Every loss holds the blueprint for your next win. Now, we treat each loss as market research and 2x'd our win rate. Do you ask for feedback after losing a pitch/deal? Drop a comment if you want my template message asking for insights to improve your next pitch! #pitch #insights #influencermarketing #improvement

I wasted years thinking small talk about weather made me good at sales. My process was embarrassingly simple: Pull up their LinkedIn, scan their last email, then wing it with some chitchat about their location or the weather. I assumed "natural rapport" meant improvising my way through calls. And I was wrong. Truth is, I was resisting structure. I believed scripting meant being robotic and proper preparation would kill authentic conversation. So I kept it casual, kept it flowing, and… kept missing opportunities. Then I started working with a sales coach. Every Wednesday at 10am, I'd get on a call to hear exactly why my approach was wrong. It was expensive, uncomfortable, and exactly what I needed. One day, he caught me using my favorite line (among others) while I talked through a sales call: "Any thoughts on that?" His feedback was brutal: "You're swinging between closed-ended questions that shut people down and questions that leave them hanging. What if, instead, you guided the conversation?" Ouch. Mind blown. He was right. In trying to keep things casual and unstructured, I'd been failing to guide meaningful conversations. My resistance to "scripted" questions wasn't just making my calls superficial—it was leaving both me and my prospects without direction. So we changed… direction: Create and rehearse a flow and replace every closed question with an open one. Instead of "Should I walk you through our services?"   → "What’s the goal?" then… “What’s behind that?” Instead of "Any thoughts?"   → "How would this fit into your current process?" Instead of "Does that pricing work for you?"   → "How does this compare to what you were thinking?" The difference was immediate. Prospects started sharing their actual concerns. Their real budgets. Their true decision-making process. All the things they used to hold back when I gave them an easy "no thoughts" escape hatch. Last quarter alone, we added a record in new MRR—twice our typical close rate. Sales cycles that used to drag on for 8 months now wrap up in 4. But the biggest change is that I finally see sales calls for what they *should* be: guided conversations with clear direction and open ended questions, *not* let-me-wing-this-trust-me-I-got-this improv sessions. The beauty of this approach is that it's not in any way manipulative or calculating. When you introduce structure and direction, you're also helping prospects quickly decide if what you have to offer is what they actually need. Everyone wins. P.S.   Try this today: Take your most common closed question and flip it into an open one, directing one. You'll be amazed at what people tell you when you stop giving them permission to say nothing.

𝗜 𝗹𝗼𝘀𝘁 𝘀𝗮𝗹𝗲𝘀 𝗯𝗲𝗰𝗮𝘂𝘀𝗲 𝗜 𝘄𝗮𝘀 𝗹𝗶𝘀𝘁𝗲𝗻𝗶𝗻𝗴, 𝗻𝗼𝘁 𝘂𝗻𝗱𝗲𝗿𝘀𝘁𝗮𝗻𝗱𝗶𝗻𝗴 𝘁𝗵𝗲 𝗿𝗲𝗮𝗹 𝗰𝗼𝗻𝗰𝗲𝗿𝗻. For a long time, I thought I was strong at handling objections. I’d respond clearly, explain the value, and even share proof of outcomes. But people still hesitated and then it clicked me. I was hearing their words, but I wasn’t catching what was underneath their doubts, fears, and unspoken concerns. Here are 𝟮 𝘀𝘁𝗲𝗽𝘀 that helped me shift from listening to truly understanding: 𝟭. 𝗣𝗮𝘂𝘀𝗲 & 𝗣𝗿𝗼𝗯𝗲: ↳ Slow down: Don’t jump into explaining. Take a breath. ↳ Listen between the lines: What emotion sits behind the objection? Fear of risk? Lack of clarity? Past bad experiences? ↳ Ask better questions: Simple, open prompts like “Can you tell me more?” reveal what they actually mean. ↳ Hold space: Let them express their real concern without rushing to fix it. 𝟮. 𝗔𝗰𝗸𝗻𝗼𝘄𝗹𝗲𝗱𝗴𝗲 & 𝗔𝗱𝗱𝗿𝗲𝘀𝘀: ↳ Validate their concern: Sometimes people just want to feel seen before they feel convinced. ↳ Get to the root: Address the fear, not just the statement. ↳ Respond with clarity: Once you understand the real issue, your explanation becomes sharper and more relevant. ↳ Build trust: Understanding creates safety. Safety creates decisions. 𝗡𝗼𝘄 𝘁𝗵𝗲 𝗻𝗲𝘅𝘁 𝘀𝘁𝗲𝗽 𝗶𝘀 𝘁𝗼 𝗽𝗿𝗮𝗰𝘁𝗶𝗰𝗲 𝘁𝗵𝗶𝘀 𝗱𝗲𝗲𝗽𝗲𝗿 𝗹𝗶𝘀𝘁𝗲𝗻𝗶𝗻𝗴 𝗶𝗻 𝗲𝘃𝗲𝗿𝘆 𝗰𝗼𝗻𝘃𝗼. #sales #coach

My sales training consisted of two things: A "lead list" (aka burned, cold, stale accounts) and a headset. That was it. Very sink or swim vibes. As you can imagine.. I made every mistake in the book. After hundreds of cold calls, meetings, and in person visits.. I've learned some things along the way. Here are 10 lessons I now know to be true (and still use to this day): 1. Confidence is key. Your tone matters more than you think. If you don’t believe in the service you’re selling, they won’t either. Speak with clarity and know your value. 2. Discovery is everything. Instead of pitching, start by asking questions. If you don’t know their pain, you can’t position your service as a solution. No one wants a band-aid without a cut. 3. Listen more than you talk. Most shippers will tell you exactly what they need, when they need it and how to close them - if you let them talk. 4. Lead the conversation. You're the expert. It's your job to lead the conversation towards clarity and next steps. It's okay to get off course here and there but don't lose direction completely. 5. Rejection isn't personal. Sometimes you can use the no to refine your approach, sometimes you can use the no to just simply move on. 6. Follow-ups is where the sale happens. The first call rarely results in revenue. But stop with the “just checking in” emails and voicemails. Bring value. Share insights. Stay relevant. 7. If there’s no next step, there’s no close. If there's no next step - expect ghosting and lost momentum. Shippers are busy, and you are too so don't just book a next step or call for the sake of it - make sure there's clear purpose in continuing the conversation. 8. Be yourself. I make 'notes' and 'scripts' all the time but if you use a script as a crutch, instead of a tool.. you won't sound like yourself. People buy from people, and people aren't perfect. We fumble over our words, we say 'ums' and can lose track of our thoughts. It's okay. Your authenticity will do more for you than your script, I promise. 9. Walk away when it’s not a fit. The fastest way to waste your time and energy is trying to force something that doesn’t fit or serve either side. Disqualify early and move on. 10. Stay in student mode. Whether you get formal sales training or not, never stop learning. Don't just copy tactics. Study what works, experiment in your own sales process and keep sharpening your mind. Last lesson that I've found to be very true that's not on the list.. Sales is what you make it, and you can choose to make it fun. Sometimes we get so bogged down with "I need revenue/freight/customers now!" that we get in our own heads and make more mistakes than we need to. Don't be over critical of yourself. Sales is a learning process, no matter if it's your first day or your 900th. Happy Prospecting! 🫶

Here are 6 of my biggest sales mistakes. (After 17 years in sales I’ve made a ton) Here are the ones I learned the most from: 1. 𝗧𝗿𝗲𝗮𝘁𝗶𝗻𝗴 𝗮𝗹𝗹 𝗽𝗿𝗼𝘀𝗽𝗲𝗰𝘁𝘀 𝘁𝗵𝗲 𝘀𝗮𝗺𝗲 At the beginning of my career, my prospecting process was: Get a list of prospects → use the same script for every call → rip calls No ICP, no research, no strategy. I wasted a ton of time & cost me and the company $$$. Quantity matters, but not at the expense of quality. ----- 2. 𝗖𝘂𝘁𝘁𝗶𝗻𝗴 𝗰𝗼𝗿𝗻𝗲𝗿𝘀 𝗶𝗻 𝘁𝗵𝗲 𝗽𝗿𝗼𝗰𝗲𝘀𝘀 I learned my company’s sales process, but in my mind, it was way too many steps. I was hired to close deals, and the process added friction. I wanted to go fast. So I started to cut out steps Allowed the prospect to dictate the next move Which resulted in every evaluation being different. Doing so had the opposite outcome I was going for. Process exists for a reason. ----- 3. 𝗦𝗲𝗹𝗹𝗶𝗻𝗴 𝘃𝘀. 𝗦𝗼𝗹𝘃𝗶𝗻𝗴 My early thoughts on selling were that I needed to “convince” prospects why they needed our product. I spent years thinking this defined great sellers. But the more I tried to “convince” the worse my results. It wasn’t until I changed my focus to “solving” problems that the tide turned. ----- 4. 𝗧𝗵𝗲𝗺 > 𝗬𝗼𝘂 I would spend hours prepping for meetings. Memorizing my talk tracks. My talk track: 30-45 min PPT monologue about my company & awards Looking back, I wish I could apologize to everyone who had to sit through one. Spend hours prepping. But make the conversation about them not you. ----- 5. 𝗕𝗮𝘁𝘁𝗹𝗲 𝗚𝗿𝗼𝘂𝗻𝗱. 𝗡𝗼𝘁. 𝗖𝗼𝗺𝗺𝗼𝗻 𝗚𝗿𝗼𝘂𝗻𝗱 For the longest time, I would get pissed anytime someone asked for a discount or tried to negotiate. I would go into every negotiation thinking I needed to: Hold my ground Defend our product’s value Believing that I needed to win That mindset cost me a ton of deals early in my career. Negotiating shouldn’t be adversarial - it should be collaborative. ----- 6. 𝗕𝗲𝗹𝗶𝗲𝘃𝗶𝗻𝗴 𝗘𝗢𝗤 𝘄𝗮𝘀 𝗟𝗶𝗳𝗲 𝗼𝗿 𝗗𝗲𝗮𝘁𝗵 Now I still struggle with this occasionally, but have gotten way better as I’ve gotten older. The EOQ can bring a lot of stress. I would prioritize it over everything: Missed family vacations Missed kid's sporting events Was absent during Holiday gatherings It’s by far my biggest career regret. EOQ is important. Balance is vital. Family is everything. Hope this helps someone. What mistakes have you made during your career?

What I learned from watching my own sales calls back. Humbling doesn't even begin to describe it. A few weeks back, I forced myself to review 10 of my recent sales calls. What I found made me cringe harder than watching my first video attempts. Turns out I was doing exactly what I tell clients not to do. The three moments that hit hardest: Moment 1: The Feature Dump At 12 minutes into a call with a SaaS founder, I caught myself listing every single thing our video funnels could do. Feature after feature. Benefit after benefit. His eyes glazed over at minute 8. I didn't notice until the replay. I literally wrote a post about this last month. Then did it anyway. Moment 2: The Fake Urgency Play "We only have two spots left for November..." I heard myself say it and wanted to crawl under my desk. I'd just posted about authentic selling with no pressure tactics! The prospect's voice changed immediately. Sales pitch guard up. Moment 3: The Interruption Pattern This one hurt the most. Every time the prospect started sharing a real challenge, I jumped in with a solution. Cut them off mid-sentence, thinking I'm a mind reader! I counted: 6 interruptions in 30 minutes. No wonder they needed to "think about it." What changed after watching these: Now I set a timer for the first 10 minutes of every call. My only job: Ask questions and shut up. I deleted all urgency language from my vocabulary. If someone needs time, they get time. I keep a sticky note on my monitor: "They're not buying your knowledge. They're buying your understanding." The results speak for themselves: Close rate before self-review: 31% Close rate after: 47% But more importantly, calls feel different now. Less performance, more conversation. The uncomfortable truth: We all have blind spots. The only difference is whether we're willing to look at them, admit our faults, and fix them immediately. Practice what you preach.

A couple months ago, I bombed a sales call. (Major learning lesson incoming) I thought I was crushing it during the call. But by the end? The prospect couldn’t see the value and said "no". Here’s what I did wrong (and what I’ll never repeat): 1. I sold the strategy, not the outcome Nobody buys “strategy.” They buy results. I was pitching a “LinkedIn content growth system” when I should’ve been painting a picture of: → Becoming the go-to authority in your niche → Turning your profile into a lead machine → Thousands of qualified followers in 90 days People don’t want the recipe. They want the cake. 2. I talked too much On this call, I dominated 80% of the conversation. This was a huge mistake. The buyer should be talking 70% of the time. Why? Because people don’t buy when they understand you. They buy when they feel you understand them. 3. I didn’t ask enough questions I wish I had asked these questions: • What does success look like for you? • What happens if nothing changes in 6 months? • Why do you want to start now? These expose their real pain and desires. And when you mirror it back later? They’ll see you as the only person who “gets” them. 4. I fumbled at the price When I said my price, I kept talking. Trying to justify it and fill the silence. But in this moment, silence is power. The moment you say your price—shutup. → No nervous explaining → No justifications → No discounts When you do this, you show that you're not confident in your own services, so you try to justify it. That call taught me something the hard way: Selling isn’t about convincing. It’s about listening so deeply that they convince themselves. P.S. What’s one lesson you’ve learned from a bad sales call?

We thought our cold calling was crushing it until no-show rates shot up 30%. - Reps were hitting their dial targets - Meetings were getting booked constantly. - Pipeline looked full. But within a few weeks of starting, we noticed prospects weren't showing up to the meetings they had agreed to book (30% more than usual). Even with call reminders and morning-of check-ins, they'd ghost or reschedule forever. We were paying our reps for "successful" calls that led to zero revenue. Here's what was actually happening. - Our callers were incentivized on bookings, not quality. - They became "yes men" hunters, speed-running through calls to hit daily targets with zero qualification during the actual conversation. - Prospects were saying yes just to get off the phone, not because they were genuinely interested. No real pain point was identified, no budget discussed, no timeline established. When meeting time came around, they had no reason to show up because they were never really interested to begin with. The fix requires discipline: 1. Do actual qualification on the cold calls themselves.  2. Ask about timeline, budget, decision-makers, and what they're currently doing to solve the problem.  3. Have sales managers review calls and provide coaching.  4. Tie compensation to show-rates or closed revenue instead of just bookings. 5. Focus on legitimate conversations, not script speed-runs. This was a tough but important lesson for us. I hope I saved you from it!

The painful lesson I learned from a sales call that taught me the difference between a vitamin and a painkiller. Early after our fundraise, we were getting a ton of introductions to sales leaders interested in our product. Our first calls were always with sales leaders. At the time, our pitch was a natural language interface that leadership could use to ask questions about their data - without digging through dashboards. What we misunderstood was that excitement from sales leaders doesn’t necessarily mean excitement from RevOps. We got an enthusiastic intro to a RevOps leader and went into the call thinking it was a slam dunk. We’d validated the leader’s pain and thought we had a solid understanding of their systems and workflows. The call itself seemed to go great - she validated several points in our thesis, spoke most of the time, and enthusiastically agreed as I pitched. So how did it go so wrong? As the call was wrapping up, I asked if they were ready to move forward and what next steps might look like. That’s when she told me they weren’t interested. Not at all. Didn’t see that coming. I genuinely thought it had been one of my best calls. But what she said next stuck with me: while it was a “pain point,” it was buried beneath a much longer stack of higher priorities. Everything I thought I was “discovering” on that call was really me asking leading questions about where I thought the pain was. It was ultimately a vitamin, not a painkiller - and we never got to what truly mattered for the broader sales org. The call was focused on what I thought mattered, not what actually did. It ended up being one of the best lessons I’ve learned about stakeholder alignment - and how each group inside an org has its own, sometimes competing, priorities.

Why Salespeople Fail (And Why That is Actually Good News) Sales gets a bad rap. When deals fall through, quotas are missed, or pipelines dry up, the word failure shows up fast and loud. But here is the quiet truth: most salespeople do not fail because they are bad at selling. They fail because they are human. One of the biggest reasons salespeople stumble is they fall in love with the pitch instead of the person. We rehearse scripts, perfect decks, memorize features and forget to listen. Buyers don’t want to be impressed; they want to be understood. When the conversation becomes a performance instead of a connection, resistance sneaks in. Another common trap is chasing “yes” instead of clarity. Many salespeople are so focused on closing that they ignore red flags. A polite prospect is mistaken for an interested one. A maybe is treated like momentum. Real sales progress comes from honest conversations, not hopeful assumptions. Salespeople also fail when they personalize rejection. A lost deal feels like a personal verdict: I am not good enough. But rejection is usually about timing, priorities, or budget, not worth or skill. The best sales professionals do not avoid rejection; they recover quickly and learn from it. And finally, there is the pressure to look confident all the time. Sales culture often rewards certainty, not curiosity. But growth happens when salespeople admit what they don’t know, ask better questions, and stay teachable. Ego closes fewer deals than humility ever will. Here is the good news: every failure in sales is feedback in disguise. Each missed opportunity sharpens judgment. Each awkward call improves the next one. The salespeople who win long term are not the ones who never fail, they are the ones who fail forward. So if you are in sales and things feel hard right now, you are not broken. You are building something. Keep listening. Keep learning. Keep showing up. That is not failure. That is progress. #Sales #LearningInPublic #GrowthMindset #B2B