Sales Training Programs

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...

For my first 16 years in tech sales, I averaged 240K/year W2 income. In my last 4 years, I averaged 720K/year. In order to triple my income, I had to change my sales approach entirely. Here's what I changed: I started using a new approach that I now call Yo-yo selling: 🪀 Yo-yo selling emphasizes starting at the executive level, conducting thorough discovery within the organization, and then returning to the executive with a tailored business case. Like holding a yo-yo, you are constantly in communication with the Executive Sponsor and updating them as you collect information and conduct deep discovery lower down in their organization. You are literally going up and down the organization, but always taking everything back to the Executive Sponsor to surface your findings along the way. Here's a breakdown of the framework: 🎯 𝐈𝐚𝐧 𝐊𝐨𝐧𝐢𝐚𝐤’𝐬 “𝐘𝐨-𝐘𝐨 𝐒𝐞𝐥𝐥𝐢𝐧𝐠” 𝐅𝐫𝐚𝐦𝐞𝐰𝐨𝐫𝐤 This strategy involves a three-step process: 1. Start at the Top (Executive Engagement) Initiate contact with a senior executive to understand their most pressing challenges, the reasons behind the need for change, and the consequences of inaction. If your solution aligns with their needs, secure their sponsorship for further discovery within their organization. To secure the Executive Meetings, it's essential to create a tailored POV (point of view) on where you think you may be able to help them based on your initial research of their highest level goals and priorities. Chat GPT has made this research a LOT faster now. 2. Conduct In-Depth Discovery (Middle Management) Engage with department heads and key stakeholders to uncover the day-to-day challenges they face. Focus on understanding their processes, pain points, and the implications of current inefficiencies. Gather direct quotes and insights to build a comprehensive view of the organization's needs. 3. Return to the Executive (Present Findings) Compile the insights gathered into an executive summary and business case. Present this to the executive sponsor, highlighting how your solution addresses the identified challenges. Tailor your demonstration to focus solely on relevant aspects that solve their specific problems. 🚀 Why It Works 1. Accelerates Sales Cycles: Engaging executives early ensures alignment and expedites decision-making. 2. Builds Credibility: Demonstrates a deep understanding of the organization's challenges and showcases a tailored solution. 3. Facilitates Internal Buy-In: By involving various stakeholders, you ensure that the solution meets the needs of all parties, increasing the likelihood of adoption. I'm pleased to share that that Yo-yo selling was recently awarded as a Top 15 Sales Tactic of All Time by 30 Minutes to President's Club, and I received a cool plaque for entering the 30MPC Hall of Fame. Since I have no chance of entering the Hall of Fame for my baseball or golf game, this is a nice consolation prize 😁

[Steal this] Recently, I ran a hands-on "Building with AI" workshop that walked our Duolingo Product Managers through spinning up brand-new language-learning challenges using the latest AI-powered prototyping tools. Here's the exact workshop guide that you can use with your team. ⬇️ Why we did it: Great PMs ship fast and learn fast. The session let the team: → Practice modern visual-to-code tools (we used Lovable and imported real Figma files with Builder.io) → Stress-test AI chat interfaces for real product work → Walk away with a functional prototype they could show (or lovingly roast) in front of their peers What we learned: → AI tools aren't replacing PMs, but they are giving them a new storytelling tool → The barrier isn't the technology. It's giving people permission (and carving out time!) to experiment → Our team is creative af - we saw games, creative lessons, roasts, you name it! Try it with your team:  We're open-sourcing the entire workshop guide. Why? Because when more PMs can prototype at the speed of thought, better products get built. Period. Your PMs are sitting on massively creative ideas! This workshop unlocks them in one afternoon. How are you experimenting with new AI tools? 👇

How do you build long-term relationships with customers? It’s not about clever sales tactics. It’s about mindset. One of the biggest shifts I’ve learned is this: neediness is the enemy of trust. When a potential customer senses that your advice is driven by your own urgency or desire to close a deal, it sets off alarm bells—because it means your motives might not be aligned with their best interest. The alternative? Focus on being a trusted presence over time. ✔️ Show up consistently ✔️ Listen carefully ✔️ Offer value without strings attached When you’re guided by genuine curiosity and service, customers come to see you as a long-term partner—not a one-time vendor. That’s the foundation of loyalty and that’s how relationships endure.

If you close $50k+ deals, I have news: Sales is not a numbers game. Sales is a skills game. 7 skills that grow your income without burning out on the volume game: 1. Finding 'the need behind the need.' Great salespeople dig under the surface. When buyers share their problems, they listen. But then they follow up with: "What's going on in your business that's driving that to be a priority?" THAT gets to the true priority. 2. Quantifying customer pain. No measurement, no money. Quantifying pain does three things: a) justifies the spend b) creates urgency c) helps your customer appreciate the magnitude of the problem. Try asking: "What metric is suffering as a result of these challenges?" 3. Creating champions. A great champion runs through brick walls to get the deal done. They sell your product internally when you're not in the room. Indeed: Salespeople don't close deals. Champions do. A league of champions is like a magnetic force for closing deals. 4. Business acumen. The best sellers in the world are actually businesspeople that happen to know how to sell. Don't just improve your SALES acumen. Improve your BUSINESS acumen. Senior execs will respect you 10x more than reps who only know the latest sales techniques. 5. Executive conversations You can close five-figure deals without this skill. But if you want to close six, seven, and eight figure deals? You better have gravitas when it comes to 'facing off' with senior execs. They're direct. They use plain language. They're efficient. 6. Negotiation. Negotiation is a 'threshold' skill. That means it makes almost all of your other skills more valuable. Becoming a great negotiator will pay dividends the rest of your life. Dig in and master it. 7. Writing. Clear writing indicates clear thinking. Sloppy writing indicates sloppy thinking. Your job as a seller is to persuade and communicate. Become a master of every medium that involves: - sales calls - written word - group presentations What skills would you add?

Something remarkable happened when we started bringing Customer Success leaders into our sales conversations. The traditional sales process transformed into a strategic partnership discussion that benefited everyone involved. After implementing this approach across hundreds of deals, we discovered benefits that went far beyond our initial expectations. Sales teams gained a deeper understanding of post-implementation challenges, which helped them qualify opportunities more effectively. Instead of focusing solely on closing deals, they began asking questions about operational readiness, internal champions, and resource allocation. Prospects received authentic insights into what successful implementation truly requires. Our CS leaders shared real examples of customers who thrived and openly discussed common obstacles they might face. This transparency built trust and helped prospects make informed decisions. Better aligned customer expectations from day one. When CS leaders joined these conversations, they highlighted potential roadblocks and success metrics based on similar customer profiles. This practical guidance helped prospects understand the work required to achieve their desired outcomes. This early involvement proved invaluable for our CS team. They gained visibility into the customer's vision before contracts were signed, allowing them to proactively plan resources and create tailored onboarding strategies. A surprising result was the reduction in "rescue" situations during implementation. We eliminated many issues that typically surfaced months into the relationship by addressing potential challenges during sales discussions. The data supported our approach. Deals that included CS leaders showed 40% higher implementation success rates and 25% faster time-to-value. More importantly, these customers renewed at significantly higher rates. For those considering this approach, start small. Choose strategic opportunities where CS insights could substantially impact the prospect's decision-making process. Document the outcomes and refine your strategy based on that feedback. Great customer relationships begin with the very first conversation.

Your sales managers are drowning in data—but starving for clarity. I was on a call last week with a VP of Sales who showed me his dashboard. 47 different metrics. I asked him : "Which number, if it moved 20% this month, would change everything?" Silence. Here's what I see happening: Leaders know *something* is off. Pipeline isn't converting. Reps are busy but not productive. Deals are slipping. But they can't pinpoint the actual behavior or skill gap that's causing it. Here's how to actually diagnose what's broken (and fix it fast): —— Step 1: Pick ONE North-Star Metric Not 10. Not 5. One. What's the single number that, if improved, would cascade into revenue growth this quarter? Could be: → Connect rate → Discovery-to-demo conversion → Demo-to-proposal rate → Close rate Pick the constraint. Ignore the rest for now. —— Step 2: Work Backward to the Behaviors Metrics don't move themselves. Behaviors move metrics. Ask: What are the 3–5 specific actions that directly influence this number? Example—if your North-Star is close rate: • Multi-threading (are reps building champion + EB relationships?) • Next-step clarity (is every call ending with a concrete commitment?) • Objection handling (are reps folding on pricing or timeline pushback?) Now you have a target. You know exactly what behaviors to inspect and improve. —— Step 3: Inspect the Work, Not Just the Outcome Most managers live in lagging indicators. They see the deal lost, the pipeline gap, the missed forecast—after it's too late. Top leaders inspect leading behaviors weekly: → Listen to 2–3 discovery calls per rep. Score them on your behavior checklist. → Review pipeline hygiene: Are next steps clear? Are close dates realistic? → Check activity quality: Are reps reaching the right people, or just burning through volume? You'll spot the gap in week one. You can course-correct in week two. —— Step 4: Use BIPSY to Diagnose the Root Cause When a behavior isn't happening, most managers assume it's a skill problem and throw training at it. But the issue might be: B – Behavior: They don't know they should be doing it. I – Issue Diagnosis: We don't know the CAUSE of the problem. P – Process: There's no clear standard or it's not reinforced. S – Skill: They know what to do but can't execute it well. Y – You (Impact): YOU as the leader aren't doing the right things. Diagnose correctly, and your fix is 10x faster. Don't guess. Diagnose. —— Step 5: Coach the Behavior Until It Sticks One conversation won't change anything. Great managers build a weekly rhythm: Monday: Inspect the work (calls, pipeline, activity). Tuesday–Thursday: Coach the gap in 1:1s with real examples. Friday: Measure early proof (did the behavior improve?). Rinse and repeat. This is system force, not brute force. The Bottom Line: Your team doesn't need more dashboards, more meetings, or more motivation. They need clarity and specific actions.

Most L&D professionals learned the Kirkpatrick Model early on. Fewer have seen it applied beyond Level 1. Here's what each level can actually look like when you put it into practice, not just the textbook definition. ✨ Level 1: Reaction 🔹 Textbook version: Did learners find the training engaging and worth their time? ✅ In practice: Instead of "Did you enjoy this session?", ask "Was this relevant to the work you do?" and "Could you apply this right away?" ✅ Metric to track: Relevance and applicability ratings, not just satisfaction scores. ✨ Level 2: Learning 🔹 Textbook version: Did learners gain the intended knowledge or skills? ✅ In practice: Replace recall-based quizzes with scenario-based checks. Can the learner apply the concept to a situation they'd actually face? ✅ Metric to track: Pre/post assessment scores on scenario-based questions, not just "did you pass the quiz." ✨ Level 3: Behavior 🔹 Textbook version: Are learners applying what they learned on the job? ✅ In practice: 30/60/90-day check-ins, manager observations, or peer feedback on whether the new behavior is showing up in real work. ✅ Metric to track: % of participants demonstrating the target behavior, based on manager or peer input, not self-reported confidence. ✨ Level 4: Results 🔹 Textbook version: Did the training impact business outcomes? ✅ In practice: Pick one business metric the program was meant to influence, before you build it, not after, and track the change. ✅ Metric to track: Movement in that specific KPI (error rates, time-to-productivity, conversion rates, retention) compared to a baseline. Most programs are measured thoroughly at Level 1 and barely at all beyond it. But Levels 3 and 4 are where the "did this actually matter" conversation happens, and they are also where L&D earns a seat at the table. Which level does your organisation measure consistently, and which one do you wish you could measure better? #LearningAndDevelopment #LnD #KirkpatrickModel #TrainingEvaluation #InstructionalDesign #LearningMeasurement #TrainingAndDevelopment #LnDStrategy

One of the best ways to create authentic relationships with your customers, get honest feedback on your product and surface game changing ideas is to create a Customer Advisory Board (CAB). Here are the lessons I’ve learned about how to create and run a successful CAB. Your personal involvement as CEO is critical. If you lead it yourself, customers will engage at a deeper level. They’ll be more honest, more vulnerable, and more likely to become evangelists for your company. No one else can unlock this dynamic the way a CEO can. Be clear on the persona. Is your CAB for buyers, users, or budget holders? At BetterCloud, our sweet spot was Directors of IT. Not the CIO, not the IT admin. Know exactly whose voice you want in the room and tailor everything to them. Skip the compensation, give them “status”. Don’t pay CAB members—it gets messy. Instead, make them feel like insiders. Give them a title, early access to roadmaps, VIP treatment at events, and public recognition. People want to feel valued and influential, not bought. Set a cadence you can maintain. I tried monthly meetings once. That was a mistake. Quarterly is the sweet spot. One in-person gathering per year—ideally tied to an industry event—goes a long way in deepening relationships. Structure matters. CABs aren’t just roundtables. They’re curated experiences. Keep meetings tight (90-120 minutes), show real products that are still in the development process (even rough wireframes or high level ideas), and create space for interaction. Done right, they become the ultimate feedback engine. Build real relationships. Your CAB shouldn’t just exist in meetings. Build one-on-one connections. Text, email, check in at events. Keep it small enough that people feel seen and valued. When they have a direct line to the CEO, they stay engaged—and they speak the truth. Done right, your CAB becomes more than just a feedback mechanism. It becomes a strategic asset. It can shape your roadmap, sharpen your positioning, and strengthen your customer relationships in ways no survey ever could. For a deeper dive and detailed tactics behind each of these, check out the full writeup on the Not Another CEO Substack.

Why Your Sales Team Isn't Hitting Targets and HOW TO FIX IT 📊Today many businesses struggle with declining sales performance, and one of my clients - a mid-sized tech firm, faced this very issue. Despite having a talented team, they consistently missed their sales targets, leading to frustration and dwindling morale. They started sales coaching with me, and here's how we started and turned things around. Conducting Diagnosis: Understanding the Core Issues through a sales audit, and after an initial assessment, it became evident that several factors contributed to the poor performance. These are listed broadly as follows: 🚫Lack of Clear Goals: The sales team didn’t have well-defined, achievable targets. They were chasing numbers without a strategic plan. 🌀Inadequate Training: Despite their talent, the team lacked training in the latest sales techniques and tools. There was also an inefficient sales process at play. 🗯Poor Communication: There was a significant disconnect between the sales team and other departments, leading to missed opportunities and misunderstandings. 📌Low Motivation: Constant failure to meet targets had demoralized the team, impacting their productivity and drive. To address these issues, we implemented a comprehensive coaching and facilitation program focusing on well executed strategies: 🎯 Setting SMART Goals - to give the team clear direction and purpose. Fine tuning the sales process also contributed to efficiency. 💪Enhanced Training - on advanced sales techniques, product knowledge, and customer engagement strategies. 🧲Optimizing the Sales Process - by identify the bottlenecks and making necessary adjustments, we ensure that the process is customer-focused and aligns with their buying journey. 🎎Improving Communication - by establishing regular cross-departmental meetings and open communication channels to ensure everyone was on the same page. 👊Motivation and Incentives - by introducing a reward system to recognize and celebrate achievements, boosting morale and encouraging a healthy competitive spirit. Within three months, there was a complete transformation - the team had a high morale and camaraderie. Soon, they not only met but also exceeded their sales targets, achieving a 30% increase in sales. The clear goals, enhanced skills, and improved communication fostered a collaborative and motivated environment. The client’s sales performance skyrocketed, and the once-struggling team became a powerhouse of productivity and success. ✨✨ Need help identifying and fixing the issues in your sales team? Contact me for expert guidance and tailored solutions! 📌https://lnkd.in/dGGM5vCK #sonniasingh #sonniasinghleadershipcoach #salescoaching #salesoptimization #businessresults #SalesPerformance #SalesTargets #TeamMotivation #SalesTraining #SalesProcess #SalesLeadership