Personalized Sales Coaching Approaches

✨Just wrapped up a coaching engagement that I can't stop smiling about 😄 When this sales rep first reached out to me, she was on a performance improvement plan 📉 and genuinely questioning whether she was cut out for sales. A veteran who'd been a top performer at previous companies, she was now missing quota for consecutive quarters at her new organization. "I'm doing everything the same way I always have," she told me during our first session. "But it's just not working here." That phrase – "the same way I always have" – was our first clue. After analyzing her approach, the pattern became clear. Her strengths had always been relationship-building and thorough discovery. Her previous companies sold complex solutions with long sales cycles where these skills shone 🌟. But her new company had a transactional offering with a shorter cycle, and her approach was creating friction rather than momentum. Instead of completely overhauling her style (which never works long-term), we identified specific micro-adjustments that would preserve her natural strengths while adapting to the new environment. 𝗪𝗲 𝗰𝗿𝗲𝗮𝘁𝗲𝗱 𝘄𝗵𝗮𝘁 𝗜 𝗰𝗮𝗹𝗹 "𝗣𝗮𝗰𝗲 𝗠𝗮𝘁𝗰𝗵𝗶𝗻𝗴" 𝘁𝗲𝗰𝗵𝗻𝗶𝗾𝘂𝗲𝘀  – ways to maintain her thorough approach but calibrate it to her prospect's buying velocity. For instance, instead of a comprehensive discovery, we designed a "Quick Discovery" framework focused on just three critical questions  with optional deep-dive paths depending on the prospect's engagement signals 𝗪𝗲 𝗮𝗹𝘀𝗼 𝗱𝗲𝘃𝗲𝗹𝗼𝗽𝗲𝗱 𝗮 "𝗩𝗮𝗹𝘂𝗲 𝗖𝗼𝗺𝗽𝗿𝗲𝘀𝘀𝗶𝗼𝗻" 𝘀𝘁𝗿𝗮𝘁𝗲𝗴𝘆  – ways to articulate complex value propositions in simpler, quicker formats without losing impact. This preserved her consultative approach while respecting the faster decision timelines. 𝙏𝙝𝙚 𝙢𝙤𝙨𝙩 𝙥𝙤𝙬𝙚𝙧𝙛𝙪𝙡 𝙘𝙝𝙖𝙣𝙜𝙚 𝙘𝙖𝙢𝙚 𝙬𝙝𝙚𝙣 𝙬𝙚 𝙢𝙖𝙥𝙥𝙚𝙙 𝙝𝙚𝙧 𝙣𝙖𝙩𝙪𝙧𝙖𝙡 𝙥𝙚𝙧𝙨𝙤𝙣𝙖𝙡𝙞𝙩𝙮 𝙨𝙩𝙧𝙚𝙣𝙜𝙩𝙝𝙨 𝙩𝙤 𝙨𝙥𝙚𝙘𝙞𝙛𝙞𝙘 𝙢𝙤𝙢𝙚𝙣𝙩𝙨 𝙞𝙣 𝙝𝙚𝙧 𝙣𝙚𝙬 𝙘𝙤𝙢𝙥𝙖𝙣𝙮’𝙨 𝙨𝙖𝙡𝙚𝙨 𝙥𝙧𝙤𝙘𝙚𝙨𝙨 —𝙬𝙝𝙚𝙧𝙚 𝙩𝙝𝙚𝙮 𝙘𝙤𝙪𝙡𝙙 𝙗𝙚𝙘𝙤𝙢𝙚 𝙨𝙪𝙥𝙚𝙧𝙥𝙤𝙬𝙚𝙧𝙨 𝙧𝙖𝙩𝙝𝙚𝙧 𝙩𝙝𝙖𝙣 𝙤𝙗𝙨𝙩𝙖𝙘𝙡𝙚𝙨. She quickly turned things around, exceeding her targets and regaining her confidence. The lesson that keeps proving itself true: Sustainable sales success rarely comes from completely changing who you are. It comes from strategically adapting your natural style to the specific environment you're selling in. Have you ever found yourself in a new role or company where your tried-and-true approaches suddenly stopped working? How did you adapt? 🤔 #SalesCoaching #PerformanceImprovement #SalesSuccess

When I removed targets from my team, the first question every sales leader asked was... “How did you stop everything turning into chaos?” The answer was simple but not easy. We replaced top down targets with something far more powerful… A personal success blueprint for every rep. If you’ve never used one, here’s exactly what it is and how it works. It's a structured, data informed plan the rep co creates with their manager. It defines the inputs, activity levels & funnel metrics they need to achieve THEIR definition of success. It becomes the foundation for coaching, accountability & weekly 1:1s. Here’s how we built it. Step 1️⃣: Start with what top performers actually do... We pulled the data from our best reps. Things like... Discovery calls per week Discovery to qualified Opps created per month Opps to close Average deal size Sales cycle Etc....you get my point. This became our baseline blueprint. Not a rule, more like a map of effective execution inside our reality. Step 2️⃣: Understand the rep's intrinsic motivators... Because a blueprint only works if the rep is building toward something they care about. But first we needed to model the openness we sought from them. I shared my personal manual for working with me; a meaty guide that included lots of personal info, including my drivers & motivations. Then we found out what drove them... Some wanted a promotion. Some had a clear earning goal. Some wanted to rebuild confidence. Some wanted to be at the top of the leaderboard. Once you uncover the driver, you can build a plan that actually means something. Step 3️⃣: Build their personalised blueprint grounded in data... This is the coaching conversation where real change happens. It sounds like… “If your goal is £X and your deal size is £Y you will need around Z deals…” “Your win rate is X%, top performers sit at Y% percent…where could you realistically get it to?” “With your discovery to qualified at X%, how many discovery calls per week do you need?” The manager questions. The rep thinks. Together they build something ambitious but believable. And everything is rooted in their personal motivator...e.g. a clear path to promotion. The rep signs off. The manager commits to coaching to it. Step 4️⃣: Contract for accountability... This is where most leaders fall. We asked every rep… “When you fall behind, how do you want me to respond?” Some wanted a Slack nudge. Some wanted a short problem solving session. Some wanted it raised in weekly 1:1s Different reps need different triggers. Agreeing this upfront turns accountability into partnership. Step 5️⃣: Use the blueprint every week... Every 1:1 followed the GROW model. Goal, Reality, Options, Will. What’s working, what's not, what options do you see and what will you commit to this week? It keeps the conversation grounded in reality and solution focussed. 5 simple steps but success is driven by the quality of the coaching. That'll be my next post...

"Improve your discovery" isn't coaching. It's lazy leadership. 'Generate more pipeline' is absolutely worthless advice. And it's why your rep is still struggling. Sales isn't about big moves. It's about tiny adjustments. Aim small. Miss small. Yet most leaders give advice so broad you could drive a truck through it: "More revenue" "Better discovery" "Handle objections" "Close more deals" Cool. HOW? I had a rep scoring 95% on their call reviews. Crushing discovery. Building rapport. Creating urgency. Still couldn't close a deal to save their life. Why? They scored 0% on the close. Zero. Everything else was perfect. But they'd get to the end and freeze up. Stumble. Rush through it. One tiny miss. Entire deal dead. That's sales. A game of inches. You can nail 47 minutes of a call and blow it in the last 3. The fix wasn't "improve your closing." The fix was specific: - Stop rushing when you sense hesitation - Ask "What questions haven't I answered yet?" before ANY close - Use silence after pricing (count to 5 in your head) - Never end with "Does that make sense?" Four tiny adjustments. Close rate went from 12% to 31% in 6 weeks. Here's what real coaching sounds like: ❌ "Improve discovery" ✅ "Ask a second-layer question after every pain point" ❌ "Handle objections better" ✅ "When they say 'too expensive,' respond with 'compared to what?'" ❌ "Build more pipeline" ✅ "Add 10 connects on LinkedIn before your first call block" ❌ "Be more confident" ✅ "Stand up during your cold calls and smile when you dial" Specificity wins. Your rep doesn't need motivation. They need a microscope. Because in sales, millimeters matter. Miss the small things? You'll miss everything. Aim small. Miss small.

Sales Coaching Over Managing: Transformative Techniques to Unlock Your Team’s Sales Potential The moment it clicked Tuesday morning, my dashboard looked pristine and my forecast looked fine. Yet two reps pinged me with the same question: “What do you want me to do next?” That was the tell—our inspection habit had bred dependency. I was policing the board instead of coaching the player, and deals weren’t moving. Core thesis - Coaching scales because it builds judgment, not reliance. When reps learn to think, they stop waiting for instructions and start creating outcomes. A quick turnaround story One of my AEs—call her L.—was putting up big activity with thin results. Stage 2→3 conversion was stuck at 31%, and her cycle time had drifted past 70 days. I didn’t add more reviews. I asked for three calls: two first meetings and one late-stage negotiation. 💥We listened to the first 90 seconds together. L. led with a long company intro and skipped framing the problem. 💥We rewrote the open to start with a customer priority and a simple agenda. 💥We set a discovery rule: leave with three stated problems, two stakeholders, one next step—every time. Then we practiced. I played the skeptical COO and pressed on business impact. We introduced a simple 1–5 meeting quality score (clear outcome, problem depth, concrete next step). Four weeks later, L.’s Stage 2→3 conversion moved from 31% to 54%. Her cycle shortened by 12 days. Same effort, cleaner execution. That didn’t come from another dashboard—it came from coaching the moments that matter. Data-driven personalization I anchor coaching on three metrics: stage conversion, stage velocity, and meeting quality. It’s enough to find the leverage point without drowning in noise. 💥High-Activity/Low-Conversion: We work on the open and discovery. I use call intelligence to tag the first five minutes and the first objection. We tighten the opener and deepen problem triangulation. 💥Low-Activity/High-Quality: We focus on prospecting rhythm. We block two hours a week for outbound, improve message quality, and test two new channels. 💥Mixed bag: We pick the lowest metric, isolate one behavior, and run a two-week micro-experiment. Every deal review includes a “moment rehearsal.” We don’t rehash frameworks for sport—we practice the next 60 seconds that will actually move the deal. Closing thought Managing keeps the lights on. Coaching turns the lights on in your people. If you want scale, build judgment. What’s your most effective coaching question or 1:1 ritual? Drop it in the comments.

Coaching isn’t one-size-fits-all Too many new sales leaders confuse coaching with telling Coaching isn’t about giving answers Based on what worked for you It’s about guiding people toward solutions So they can own their growth The best leaders adapt their coaching style To where their reps are based on tenure, skill, desire… And to the situation: - 1:1 coaching → deep dives into skill gaps and goals - Group call coaching → pattern spotting that benefits the whole team - Training sessions → structured teaching new skills or processes - Micro-coaching → quick, specific feedback in the moment - Peer coaching → reps learning from each other’s wins and losses Coaching isn’t just a meeting on your calendar It’s an ongoing feedback loop Know when and how to deploy each type of coaching For the leaders out there — what’s your go-to coaching style? How have you created a coaching culture within your team? #SportsBusiness #SportsSales #SalesLeadership #SalesCoaching #SportsCareers #LeadershipDevelopment #CoachingCulture #TicketSales