Why You Need Ongoing Sales Training

"We brought in a trainer for two days and nothing changed." Of course it didn't. You treated training like a checkbox activity. Sales leaders constantly make this mistake: → Hire external trainer for 2-day workshop → Everyone gets excited during sessions → 30 days later, zero behavior change → "Training doesn't work" Wrong. Your approach to training doesn't work. Here's what actually happens: Day 1: Reps are pumped. Taking notes. Asking questions. Day 2: Still engaged. Ready to implement everything. Day 30: Back to old habits. Zero retention. Why? Because you treated symptoms, not the disease. You didn't change their daily habits. You didn't provide ongoing reinforcement. You didn't build systems for accountability. Real training that creates lasting change looks different: #1 It's diagnostic first. Before any training, you identify specific skill gaps through call reviews, deal analysis, and performance data. Not generic "they need better discovery" but specific "they ask surface level pain questions but never uncover business impact." #2 It's delivered in sprints. Six weeks of twice-weekly sessions beats a 2-day workshop every time. Reps can practice between sessions, get feedback, and build muscle memory. #3 It includes reinforcement systems. Weekly coaching calls, peer practice sessions, and manager check-ins. The learning doesn't stop when the trainer leaves. #4 It measures behavior change, not satisfaction scores. "Did you like the training?" is worthless. "Are you now asking better discovery questions?" matters. #5 It provides job aids and frameworks. Reps need cheat sheets, email templates, and conversation guides they can reference in real situations. Most importantly: It's customized to your specific challenges, not generic sales advice. The companies that see 40%+ improvement in performance don't do one-off training events. They build learning into their culture. They have weekly skill-building sessions. They do call reviews with specific feedback. They practice objection handling until it's automatic. Stop buying training like it's a magic pill. Start building capability like it's a muscle that needs consistent exercise. Your reps deserve better than motivational speeches that wear off in a week. — Tired of wasted training budgets? I'll design a performance improvement system that actually creates lasting behavior change. Book a diagnostic: https://lnkd.in/ghh8VCaf

Are your salespeople covered in Band Aids? Too often, sales leaders are on the hunt for the quick fix. The “Band Aid” solution. We study harder. We memorize scripts. We push product knowledge into our reps until they can recite it backwards and forwards. And for a while, it works. But here is the problem: Band Aids always fall off. They cover the wound, they buy us time, but eventually, we need another one. In sales, that means temporary bumps in performance but not real transformation. Here is the truth. If your sellers only learn to regurgitate product details, you are training them to compete in the most transactional game possible. And in today’s world, transaction alone will not win. Buyers expect more. They need more. Imagine this instead. What if your sellers not only knew the product inside and out, but also knew how to truly communicate? I mean really communicate, in a way that makes the person on the other side of the conversation feel seen, heard, and connected. That is not a Band Aid. That is a root solution. That is the kind of capability that does not peel away with the next quota cycle. When sellers learn to connect at the human level and deliver the product knowledge with clarity and confidence, the outcome is predictable: Stronger trust Shorter sales cycles Deeper relationships Sustainable growth No more Band Aids. Just real sales transformation. If you are a sales leader, ask yourself: are you training your people for the quick fix or equipping them for lasting change?

Stagnation is the stealthy competitor in the sales world. Here's why 👇 After 30+ years across corporate sales and now running my own sales consulting business, I've seen firsthand how resting on old laurels means falling behind. The top performers in sales aren’t just naturally talented — they're perpetual students of their craft. Here’s what decades in the field have taught me you need to be doing as a salesperson: ↳ 𝐀𝐝𝐚𝐩𝐭 𝐭𝐨 𝐌𝐚𝐫𝐤𝐞𝐭 𝐃𝐲𝐧𝐚𝐦𝐢𝐜𝐬: Sales trends and client needs shift rapidly. Staying updated is no longer an option if you want to stay relevant. If you lean on what's worked for you in the past, you might not have a very bright future. ↳𝐄𝐧𝐡𝐚𝐧𝐜𝐞 𝐘𝐨𝐮𝐫 𝐒𝐤𝐢𝐥𝐥𝐬: Each new strategy, tool, or piece of technology you master sharpens your existing skills and often opens entirely new avenues for client engagement. Role practice with your managers (or if you're a manager, implement role practices for your team) ↳𝐄𝐱𝐜𝐞𝐞𝐝 𝐂𝐥𝐢𝐞𝐧𝐭 𝐄𝐱𝐩𝐞𝐜𝐭𝐚𝐭𝐢𝐨𝐧𝐬: Today's clients are more informed than ever. They expect their sales contacts to be advisors, not just order takers. They value sales professionals who are knowledgeable and forward-thinking and can quickly identify if you're an old dog unwilling to learn new tricks. Continuously updating our team's knowledge and approach has kept us competitive and has been a cornerstone of my success. Whether you're just starting in sales or are a seasoned pro, embracing a mindset of continuous improvement is one of the most important things you can (and should) do. Don’t just aim to keep up — strive to set the pace.

What sales leaders aren’t telling you about training effectiveness. Three months ago, a company spent thousands of dollars on sales training. Today, nothing has changed. This isn't just their story. It's an epidemic in sales leadership. Here's what I discovered while researching for my upcoming book on entrepreneurial leadership👇 Traditional training fails because it treats learning like an event, not a journey. It's like trying to get fit by attending a one-day gym session. Last quarter, I worked with a team that took a different approach. Instead of a massive training budget, they invested in daily micro-learning moments: Their sales manager spent 15 minutes each morning reviewing one call with one rep. They focused on a single aspect - maybe it was tonality, or question technique, or objection handling. Over 90 days, every team member received personal coaching that stuck. Their conversion rate doubled, but more importantly, their confidence soared. Real growth happens in these small, consistent moments of feedback and practice. This insight became a cornerstone of my Sales Pitch Mastery program. We don't just dump information - we build daily improvement habits. The future of sales leadership isn't in grand training events. It's in creating a culture of continuous learning. What small learning moment could you create for your team today? #sales #coach #salestraining #salestips #strategies #salesstrategies #salesprocess #teams #growth

Professional athletes spend 90% of their time training — practicing the fundamentals, sharpening their skills, and preparing to win — and only 10% of their time actually performing. Yet in Corporate America, most of the time... it’s the exact opposite. I know in most sales organizations they spend 90% (or more!) of their time performing — in meetings, on calls, trying to close deals — and barely carve out time to actually practice and grow those skills. Then we wonder why people burn out or plateau. This illustration below says it all: Pro athletes would never skip practice and expect to perform at their best. But too many companies still expect championship results with almost no dedicated time to develop the craft. That’s why I’m so proud of how we do things at Associa led by our masterful trainer Jenniffer Harrington, CMCA. With Jennifer's guidance we make continuous training and development part of our culture — not a once-a-year event. From onboarding to advanced workshops, we invest in our people’s selling skills, leadership capabilities, and industry knowledge so they can perform like champions when it counts.

Most revenue orgs don’t teach unit economics and it's time to better equip our teams. Too many sellers - and more leaders than you’d think - don’t understand how client-facing items such as payment terms, pricing, and opex truly impact them and the business decisions made around them. If more people actually understood how their company makes money, they’d make totally different decisions. It would lead to better negotiating and knowledge of when to say “yes,” “no,” or “how can we meet in the middle” convos. Without, we reward revenue that looks good on paper, but unbeknownst to the sales and ops teams, create risk that inherently hurt the business. In 2025 and beyond, we have to teach this better. Yes - we need to train teams on features, positioning, and differentiation. But we also need to train them on: • Opex • Payback periods • The compounding effect of CSAT on retention • And how all of this ties into business health (and job security) If this sounds like a general finance crash course, it is. And it's needed in today's high-stakes macro environment and comp expectations. How can we win if we don't know the game we're playing? This transparency is valuable even when discussed with clients (of course, with no IP shared). It helps shape the "why" behind your proposals v "my manager says we need to be at X rate." These are the strategic conversations that build long-term internal and external partnerships and it starts with training. It starts with investing in the professional development of our teams. Goes without saying but it also starts at the top.

I used to think that "sales training" was a one time thing but then realized I was wasting a metric ton of money. I learned that with "one-time sales training," I'd get a blip in productivity increase but then reps will "revert to the mean." What does this mean? This means that they'll go back to their old stinky ways UNLESS you have a definite plan in place that is mandatory for the sales managers and the reps to continue for a long period of time. We spent over $300k on Sandler Training at one of my last companies but here’s what I did differently to make it stick: 1️⃣ Mandatory ongoing certifications—for reps and managers. 2️⃣ We baked Sandler’s language into our CRM so it became part of our daily workflow. 3️⃣ I continued 𝙢𝙮 𝙤𝙬𝙣 certification for 6 months to show everyone that I was ALL IN. Sales training without reinforcement is a huge waste of money and time. Learn from my mistakes. What other tips do you have to make one-time training stick better for the reps?

Think one-time training is enough? Think again. Here’s why daily coaching beats occasional training. Training Once Is Not the Solution: Many believe that a single, intensive training session is all SDRs need. But that’s like expecting an athlete to be game-ready after just one practice. The Reality: - Skills Fade: Without regular practice, skills get rusty. Habits Die Hard: People often revert to old habits without consistent reinforcement. Case in Point: After learning a new shortcut, people reverted to the longer path when it reopened. Similarly, many stopped frequent handwashing despite a pandemic. What Works: - Continuous Coaching: Daily practice and feedback keep skills sharp. - Consistent Reinforcement: Regular coaching helps maintain new habits. Doc Rivers, NBA basketball coach says, "Championships are won at practice." Don’t rely on one-time training. Say hello to continuous coaching to ensure lasting success. Change isn’t a one-time event; it’s a daily process. Start coaching your SDRs every day and see the difference. #sales #sdr #coaching

“The Best Salespeople Are Consistent Learners” Most people in sales are performing 99% of the time. Calls. Demos. Forecasts. Quarter-end chaos. Start again Monday. Meanwhile, professional athletes spend the majority of their time training… and a tiny fraction performing. And honestly? Sales should be the same. Because the best salespeople aren’t the loudest or the most confident — they’re the most consistent learners. They: • Review calls • Build reps • Get coached • Study objections • Work on their mindset • Practise the basics over and over again Most teams get a single “training day” once a quarter and wonder why reps plateau. What would happen if sales teams trained even 10% as much as athletes? Conversion goes up. Confidence goes up. Culture goes up. Training isn’t a luxury. It’s the competitive edge. What’s one thing you’re actively training right now a skill, a habit, a process? Drop it in the comments 👇 (And feel free to steal this framework for your own team.)

Last night the Founder/CEO of a Series A hyper-growth startup called me and asked why his salespeople aren't getting better. It took 1 minute to diagnose. I don't care how much training your VP Sales or Sales Trainer provide to the team, there's one thing that's always most important, yet often missed. That's Peer-to-Peer training (I call it P2P for short). P2P training should become your greatest knowledge sharing practice on a weekly basis. This makes sense when you get to the point of scale where you have top reps on the team who are crushing it. At a certain point they'll ultimately know more than your VP Sales or even trainer, because they're on the front lines every day. --- Here's how it works (super simple): 1. Schedule weekly team meetings that have only one item on the agenda; Peer-to-Peer training in open dialogue format 2. VP Sales, Director, Manager, or Trainer should host the session but the real magic is coming from the team 3. Everyone prepares in advance by bringing 1-3 scenarios to the table that they either need help with (or) want to teach to the team 4. Each rep shares their scenario (describes it, or plays a video, or shows the email dialogue) and either teaches the team what worked (or) asks the team what they would do in this situation 5. An open dialogue takes place, some debating, and eventually some consensus (if no team consensus, the leader provides it) 6. The VP Sales (or whoever runs the meeting) documents the agreed upon best practices and distributes to the team afterwards by updating scripts, objection playbooks, etc. --- By taking a proactive approach to facilitating P2P conversations each week you enable a massive amount of knowledge sharing that otherwise wouldn't happen. By requiring everyone to bring 1-3 scenarios to the table you push salespeople who would otherwise be less inclined to ask for help (or offer it) and the culture of the team becomes one of growing and learning together. As a sales leader, you'll be absolutely shocked at how productive these sessions become and how much YOU actually learn from your team. Don't just wait for questions to come to you... you have to facilitate these conversations on a regular basis. This is EVEN MORE important for remote teams who don't have the luxury of asking the person sitting next to them for help. How many of you have participated in sessions like this? If not... suggest it to your leader today. It's the one team meeting that's actually worth having on the calendar.