Addressing Skill Gaps in Sales Team Training

Most sales orgs aren't failing because of effort. They're failing because they're trying to scale hustle instead of skill. Here's what nobody wants to hear: You can only grind so much. You can only work harder for so long. You can only add more effort before you hit the wall. But skills? Skills have no ceiling. Skills compound. Skills scale. Every elite performer in every field knows this. Sales is the only profession where we still pretend more dials equals more mastery. Science says the opposite. Now let me be clear: Effort absolutely matters. You can't be lazy. You can't skip the work. Effort is the foundation. But effort doesn't scale. And here's what's actually happening: most orgs are burning people out by applying more effort to the wrong places. More cold calls to bad lists. More follow-ups on dead deals. More time in the CRM, less time on skill. That's not a strategy. That's a hamster wheel. So how do you actually develop skill that scales? Deep Practice Beats More Practice Elite performers grow skill by practicing in the struggle zone. Not easy reps. Not mindless repetitions. Precision, mistakes, and correction strengthen neural circuits. Most orgs give reps more calls, not better rehearsals. Retrieval Beats Review If your reps can only explain your value prop when the slide is on screen, they don't actually know it. Hustle says "watch this recording." Skill says "tell me the story cold, from memory." Desirable Difficulty Works Smooth training produces fragile skills. Hard, awkward, uncomfortable training produces durable skills. If your team never struggles in practice, don't be surprised when they crumble under pressure. Real Calls Are Messy Most training is blocked: Week 1 discovery. Week 2 objections. Week 3 pricing. But real calls? All that at once. Chunk it first, then apply it together. Skill scales when practice looks like the game. Experience Doesn't Equal Skill 10 years of selling isn't 10 years of growth. Most sellers hit "good enough" then skill flatlines. Only deliberate practice breaks the plateau. Hustle can't fix plateau. Coaching can. Here's the punchline: Hustle increases output. Skill increases capacity. If you want a team that gets better every quarter, if you want revenue that compounds, if you want leaders who aren't stuck in the forecasting hamster wheel... Stop trying to scale effort. Start engineering skill. Skills scale. Effort caps. Build skill, and the whole machine gets lighter. P.S. I got deep into the science of skill development about 6-7 years ago, and it completely changed how I approach sales enablement. Some of my favorites: The Talent Code. Make It Stick. The Science of Accelerated Learning. Rapid Skill Development. Moonwalking with Einstein. If you're serious about building a team that actually gets better, start there.

🚨 𝗦𝗲𝗹𝗳-𝗮𝘄𝗮𝗿𝗲𝗻𝗲𝘀𝘀 𝗶𝗻 𝗦𝗮𝗹𝗲𝘀? Most teams think they have it. I know.. The word 'Self-awareness' has been tossed around like a chew toy - too worn out to grab, too overused to notice. But here's the thing: Old doesn't mean it's not classic gold. After 10 years of working in sales orgs & another 12 working with sales teams, I've watched this pink elephant stomp on more deals than a poor pipeline ever could. Here's the expensive reality when sales pros lack self-awareness in their: 🔹 𝗪𝗼𝗿𝗹𝗱𝘃𝗶𝗲𝘄 → The lens they unconsciously use to assess prospects. Eg: They instinctively prioritise prospects who ‘look’ successful or come with swanky brand names - assuming they’re the only high-value leads. 🔴 Potential Fall: Missing golden opportunities because they're too busy judging prospects through personal biases. ✅ Move: Coach the team to challenge their own surface-level assumptions. The right prospect isn’t always the most obvious one. 🔹 𝗧𝗵𝗼𝘂𝗴𝗵𝘁 𝗣𝗮𝘁𝘁𝗲𝗿𝗻 → The internal narratives shaping their approach. Eg: “Let’s get this done in the shortest, most efficient way.” 🔴 Potential Fall: Rushing the process—jumping into selling mode before fully understanding the prospect’s real needs, leading to shallow conversations & lost deals. ✅ Move: Efficiency isn’t just speed—it’s outcome. Train reps to be empathic listeners - not just to gather information, but to connect with emotions. 🔹 𝗘𝗺𝗼𝘁𝗶𝗼𝗻𝗮𝗹 𝗣𝗮𝘁𝘁𝗲𝗿𝗻 → The underlying emotions shaping their behaviour. Eg: “If they say no, they’re rejecting me.” 🔴 Potential Fall: A ‘No’ to the product feels like a ‘No’ to them. Instead of detaching, they spiral—dwelling in shame, overanalysing the loss, or get hijacked into a mode of desperation for a quick win. ✅ Move: Detach identity from the deal. Coach teams to build intrinsic self-regard. The best salespeople study the ‘No,’ refine it, & move forward—without dragging their self-worth into it. 🔹 𝗛𝗮𝗯𝗶𝘁𝘂𝗮𝗹 𝗔𝗰𝘁𝗶𝗼𝗻 → The behaviours shaping how they’re perceived. Eg: “Clients matter. Everyone else? Not my problem.” 🔴 Potential Fall: Transactional over relational. They chase deals but neglect non-clients, peers & strategic relationships—making them forgettable, unlikable, and unreferrable. ✅ Move: Likeability is leverage. Train reps to build genuine connections, not just close deals. Being great at sales means people want to work with you again, & send others your way. Case in point? I work with massive sales teams but would only refer clients to the ones I trust & like. Sorry, not sorry. Self-awareness in sales isn’t just about knowing your strengths & weaknesses. It’s about knowing your blind spots before they cost you business. The best sales pros I've met are connectors, listeners, & self-correcting individuals who don’t let their own ego, assumptions, or habits get in the way of a deal. Which point resonates? Share below! 👇🏼 #SalesEQ #Resilience

Partner enablement is often thought of as how we are enabling our partners. But sales teams are the frontline of revenue, and their success often hinges on understanding the value partnerships bring. Many organizations fail to equip sales reps with the tools and training they need to make the most of partner-driven opportunities. If you want your partnerships to truly drive impact, you must tailor enablement for your sales team. Here’s how to get started: 1. Sales reps need clarity on how to integrate partnerships into their process. Make sure your training covers: * The Partner Pitch: What’s the unique value of a partner-driven lead, and how should they position it to the customer? * Co-Sell Opportunities: How do they collaborate with partners during the deal cycle? Define roles and responsibilities for seamless execution. * Engagement Process: What’s the step-by-step process for involving a partner? Whether it’s looping them in for a demo or escalating technical questions, clear guidelines prevent delays and confusion. 2. Provide Easy-to-Use Tools: Sales enablement shouldn’t feel like homework. Create resources that are quick to access and easy to use, like * Quick-Reference Guides: Summarize partner value propositions, key metrics, and FAQs in a single document. * Cheat Sheets for Objections: Offer pre-written responses to common challenges when selling partner-driven solutions. * CRM Templates: Use CRM workflows to automate the partner engagement process, keeping it simple and repeatable. 3. Integrate Training into Sales Routines Don’t overwhelm your sales team with one-off workshops. Instead, embed partnership enablement into their day-to-day routines: * Add partner updates to weekly sales meetings. * Offer bite-sized training videos or guides they can review on-demand. * Celebrate wins from partner-driven deals to reinforce the value of collaboration. 4. Pair new sales reps with a “partnership ambassador” on your team to provide hands-on guidance during their first partner-driven deals. When sales teams understand how partnerships drive value, they become powerful advocates for partner-driven growth.

Sales teams often build from the top down. That’s why they break. I’ve spent decades studying what separates consistent performers from one-hit wonders. It comes down to this pyramid. Start at the foundation. Habits. Three clear priorities every morning. Follow up with purpose, not just to check in. Maintain clean systems. Build momentum through small daily wins. Consistent structure beats motivation every time. Next level up. Skills. Discovery that uncovers real impact. Objections handled early, not late. Negotiation anchored on outcomes. Demos that show value created, not features listed. The best sellers talk less, listen more, and guide with intent. Then comes Mindset. Treat rejection as feedback, not failure. Build confidence through preparation, not personality. Stay curious. Optimize for learning first, outcomes follow. Growth-oriented sellers outperform those chasing quick closes. Now you’re ready for Process. A predictable pipeline rhythm. Templates that move fast but personalize where it matters. Measure what converts. Forecast with evidence, not optimism. Disciplined process closes more deals than instinct alone. Finally, Edge. Build a reputation that precedes the meeting. Share wins and playbooks internally. Run experiments, not guesses. Coach others. Visibility and credibility create warmer referrals and more inbound.

Your best rep converts at 52% while others struggle at 19%. You think it’s a talent issue. Psst… It's not talent. After analyzing 100+ sales teams, I've discovered what's really behind performance gaps. Most revenue leaders assume it's talent and throw money at symptoms: → Implement MEDDIC when only 30% have qualification issues → Hire more reps when the problem is conversion rates → Roll out Challenger when the gap is discovery skills Let me give you some real client examples why it’s not a talent issue 👇 A fintech company spent $280K rebuilding lead generation when the real problem was discovery calls averaging 22 minutes instead of 47 minutes like their top performer. One methodology change fixed it in 30 days. Your top performer hasn't gotten lucky. She's cracked a code others haven't. A cybersecurity company hitting 43% of $28M target. CEO wanted to double from 12 to 24 reps. Our analysis revealed their top performer converted qualified leads at 67% while everyone else averaged 23%. Same territory. Same leads. Same training. The rock star developed a discovery framework that identified economic buyers and quantified business impact within two calls. Everyone else ran generic discovery hoping for the best. We built systematic frameworks based on his approach. Result: $4.2M additional revenue with the same 12-person team. An HR tech’s pipeline looked healthy at $38M. Analysis revealed 71% of opportunities stuck in discovery 60+ days. Proper qualification frameworks dropped pipeline to $22M but closed rate jumped from 23% to 41%. Result: $2.3M more actual revenue. Look. Your team isn't broken. Your reps don't lack potential. You need to systematically identify conversion leaks and install frameworks that address them. Your best rep has already solved your revenue problems. We just help you build frameworks so everyone else can execute like them too. — Get a complete revenue diagnostic here: https://lnkd.in/ghh8VCaf

In 2 years, we cut Aligned’s sales cycle from 75 to 22 days, while moving up market and increasing ACV 44%. The key? Our team meets EVERY WEEK to optimize our sales playbook. Here’s our end-to-end workflow: 1. Playbooks get old within a few months—Build a regular update cadence How buyers evaluate you and make decisions constantly changes as your product, market, competitors, and economy change. Discussing these changes weekly forces us to adapt. We figure out if we need new enablement assets, training, or if our workflows need a refresh. 2. Most playbooks are “Set & Forget”—Build a system to monitor & analyze At Aligned, we use Deal Rooms to run our playbook. We analyze our best and worst-performing rooms weekly based on buyer engagement. This helps us understand what aspects of our process are effective and identify gaps. For example, an AE might create a new tab to run competitor comparisons or a business case framework that drives more exec engagement. 3. Most wait too long—Quickly turn gaps into sales or buyer enablement assets Most teams lack a routine to find OR fix gaps. Also, most teams put too much weight on sales enablement assets like scripts or training materials. Last week, Kevin "KD" Dorsey told me he sees deal rooms as an excuse for constantly creating buyer enablement assets like ROI calculators and guides. He said, “Investing in buyers must become a habit, or you’re not going to get far”. I couldn’t agree more. 4. Most skills stop at training—Embed every new skill into a dedicated template I’m a 4x sales leader. One thing I was NEVER able to do right is to get the team to consistently follow the playbook. At Aligned, we’ve tackled this by updating all customer-facing workflows in our deal room template (e.g. How we run MAPs, POCs, Business Cases...). We then use the internal-only view to templatize resources like discovery and demo frameworks. Centralizing it in one place makes it easier for the team to follow our processes. 5. Over-standardization is as bad as winging it—Encourage breaking your process A sales leader’s dream of having the ‘perfect’ process executed by their team can also be their worst nightmare. Yes, you want AEs to see what good looks like and follow what works. But do it too often, and you end up killing intuition and creativity. THE essence of what makes complex selling work is knowing how to dance. That's why our biggest updates to our template come from our team on the front line, not top-down. TAKEAWAY: There’s no quick fix for improving Deal Velocity metrics. Simply increasing price 15% won’t magically solve ACV. There are multiple potential root causes to identify. And multiple ways you can address them. But what you truly need… Is a structured way to enhance your process. Monitor, Analyze, Iterate, and Scale. That’s what has worked best for us. You have to be strategic about it. EDIT: People asked—Aligned is the Deal Room we use. It's 100% free to try https://lnkd.in/dwX_Zizk

🛑 Stop Blaming Your Sales Team. (It’s Not Their Fault.) A sales leader recently told me, visibly frustrated, “Most of my salespeople just don’t perform!” If I had a dollar or Euro for every time I heard that, I could retire tomorrow. 😉 The truth is, salespeople aren't failing because they lack skills or motivation. They fail because leadership often hands them the steering wheel but forgets to give them a map, fuel, or driving lessons. The actual performance gap isn’t in the sales seats—it’s in the coaching box. The Unhelpful “Coaching” Checklist 📝 You cannot develop a professional sales team by merely instructing them to do these things: - Attract new customers. - "Pick up the phone and make appointments." - Begin mailing prospects. - "Do something..." That's the sales equivalent of telling a marathon runner, "Just run faster!" It’s management by wishful thinking, not strategy. The Shift: From Manager to Master Coach 🚀 The issue isn't malice; it's a lack of a clear, actionable system. As leaders, our role is to transition from being mere administrators to becoming Strategic Developers who equip others with the tools for consistent success. Here's what your sales team truly needs to transform into a high-performing engine: ✅ The Blueprint: a customised sales playbook and a consistent, measurable sales process. (Without a process, dependable results are unlikely.) ✅ The Edge: Training in successfully prospecting for new business and creating a competitive advantage against major rivals. ✅ The Drill: Well-organised, near-real-life role-play sessions designed to refine skills, improve attitude, and boost confidence under pressure. ✅ The "Why": Grasping and leveraging the genuine motivation of your salespeople to enhance both new business acquisition and customer growth. ✅ The Retention Strategy: Identifying what is essential for your existing customers so your team can keep them long-term and enhance their value. 🔥 The Urgency of Investment Neglecting sales development isn't "saving money." It's the most costly strategy you can choose. Every day you postpone investing in a strong sales structure is a day you leave high-value revenue on the table. Break the cycle of blame and start the cycle of growth. You have talented people. Provide them with a system that enables them to succeed. With 40 years in sales and management, I specialise in transforming vague goals into tangible, high-impact performance systems. If you're ready to stop blaming your team and start building a Killer Sales Engine that provides predictable, sustainable results, let's have a chat. Send me a DM and we'll meet and talk! P.S. What is the most common, unhelpful advice you've heard a sales leader give their team? Share your story below! 👇

Your top rep closes $2M a year. Naturally, you want them training new hires. Six months later, those new hires are struggling, and your star rep is frustrated. "They just don't get it. I showed them exactly what I do." And that's exactly the problem! Your best salespeople don't follow best practices. They've transcended them. They close deals through intuition, relationships, and experience that can't be taught in a training session. Top performers are jazz musicians. New hires need to learn scales first. - Your star rep might skip discovery because they can read micro-expressions over Zoom. - They might break every pricing rule because they know exactly when and how to negotiate. - They wing demos because they've given the same pitch 500 times. It's bonkers to try and teach that to a new hire. Here's who should actually be training your team: 1. Your solid middle performers. They follow process because they HAVE to. They've systematized what works. They can explain the "why" behind each step because they still think about it. 2. Your recent successful hires. They remember what it was like to not know anything. They can bridge the gap between "complete beginner" and "functional rep." 3. Your former reps who became great managers. They've learned to articulate what used to be instinctive. They understand both the craft and the teaching. So, what should your gangster top performers do? - Shadow deals, don't lead training. - Let new hires listen to their calls. But have someone else explain what they're hearing and why it works. - Share war stories, not methodology: "Here's a crazy deal I closed" is valuable. "Here's how you should always handle objections" from someone who doesn't follow their own advice is not. - Mentor specific skills, not general process. - Use them for advanced topics: complex enterprise deals, handling C-level conversations, navigating procurement. Teaching is a skill. Selling is a skill. They're not the same skill. 🙂 Your best reps became great by breaking rules they mastered first. Your new hires need to master the rules before they can break them. So stop expecting your closer to be your teacher. Use them for what they're great at: closing deals and inspiring others to want to get there. But for actual training? Find someone who remembers what it's like to need a process. Because the rep who "just knows" can't teach someone who doesn't know yet.

Do you really think replacing the salesperson will fix occupancy? Outside of legitimate HR issues, swapping out a salesperson because of metrics alone often creates more damage than progress. And no— A PIP is not a strategy. It is usually an admission that leadership missed the real issue. Before you post the job ad, answer this: Where is the pipeline actually breaking? • Is it lead-to-connection? • Tour-to-advance? • Advance-to-decision? • Or the absence of a real next step? Most teams aren’t underperforming because of effort. They are underperforming because the process is vague, unfocused, and poorly coached. Here’s what actually moves occupancy: 1. Dive into the pipeline—not the personality Metrics don’t indict people. They expose skill gaps. 2. Narrow the focus Fix one or two conversion points, not everything at once. 3. Train to the gap Teach how to advance a family, not how to “follow up.” 4. Bake in accountability Coaching without accountability is encouragement. Accountability without coaching is punishment. And let’s stop chasing unicorns. Great salespeople are rarely found fully formed. They are created—through clarity, coaching, repetition, and leadership. One more uncomfortable truth: If occupancy isn’t moving, look upstream. You also need regional leaders who can coach and train, not just: • Send polished emails • Re-state CRM data • Micromanage basic tasks Occupancy doesn’t change because of reports. It changes because someone teaches, observes, corrects, and advances the team. Hope is not a growth strategy. Leadership is. #hiring #teambuilding #greatleaders

When I was first in enablement, a leader told me, "I don't care what works for other companies; I care about what's working for us right now." That always stuck with me. Much of what I do in enablement involves gathering data, strategies, and stories about what's working well for our best reps. This has impacted how I run sessions related to sales skills. They've become question-based modalities rather than "training." I present data on what's working well, situational statistical differences between top performers & average performers (specifically at Egnyte), and anonymized Gong call snippets. During those discussions, I ask the reps several questions - my sentences skew inquisitive rather than declarative. Why is this? Because reps don't want to hear blathering general sales advice on a 200-person call about how they should sell. Reps seem interested in what else is out there, and what's working for peers they respect. There's an element of FOMO there. It's better to present compelling data (shoutout Gong trackers) that impact closed/won in small groups and make it interactive by asking reps how it compares to their experiences. How would they change a shown example? How have similar examples impacted their deal execution? Why do they think that is? How have they overcome common pitfalls? The answers to skill improvement pathways likely lie within your reps; creating a forum to debate strategies and share experiences empowers them rather than alienates them with platitudes. So, rather than spending a ton of time rehearsing what you will say, gather your data and think hard about the powerful questions you will ask. The reps' responses and the facilitation of healthy discussion will sort out the rest. #presenting #facilitatingtraining #enablement