Salesforce Skill Development

Some of my hardest lessons as a sales leader came when figuring out how to setup and run training (learn from my mistakes!) Me as a new leader: "Great we have 10 topics we want to cover... let's do 1 a week. 2.5 months later we will have covered SO much ground!" 🙃 Training was more of a "box checking" exercise. Someone shared feedback on what they wanted to learn, and it got added to the list Having one 30 or 60 minute training on any topic is never sufficient, and I did the team a disservice So what was missing? And what did I seek to add later? 👉 Focus Instead of 10 topics, we might go into a quarter with 1-2 priority focus areas. The deeper engagement on a narrower topic is not unlike narrowing your focus on a smaller set of ICP accounts This creates room for practice, follow up sessions, different voices delivering the material, and ultimately makes the content stickier 👉 Engagement from other departments Where applicable, involvement from other departments can add incredible value to your training program. For instance, when you are training on a new product category, it is valuable to: - Hear firsthand from Product how it's built - Align your training timeline with Product Marketing so that materials are ready to go as the training commences - Work with Marketing so that messaging aligns to how you can sell it and everyone has the same talking points from day 1 - Work with Rev Ops to identify a market opportunity to apply your learnings - Have Sales Enablement help prepare uses cases in your sales tech stack 👉 A system to encourage accountability Once the trainings are delivered, how do you know that the sales team was paying attention? That can take many forms: - Group activity like pitch practice - Measuring adoption through tools like Gong - Contest/SPIF to encourage initial matching sales activity - Knowledge tests in your LMS (my least favorite) 👉 Repetition There's a reason Sesame Street used to repeat episodes during the week - once wasn't enough to get the message home! While your sales team isn't full of 3 year olds, similar principles apply Bottom line: instead of thinking about any topic as a single "training", think about creating "training programs" for your team 🎓 Tying it all together for a training on "New Product A" Week 1: Product & Product Marketing introduce the new offering Week 2: Outside expert/marketing/leadership deliver the industry POV Week 3: Team gets together to identify prospects and practice the pitch Week 4: Team provides feedback on material and prospecting plans are built incorporating the training Weeks 5-8: Measuring adoption through Gong. Shouting out strong adoption and privately helping laggards identify gaps in understanding Week 6: Short contest to encourage cross/up-sell opportunity creation Week 12: Revisit/Feedback #SalesEnablement #SalesTraining #LeadershipLessons #CorrCompetencies

How I run sales meetings that lead to next steps 90% of the time. Running a successful sales meeting involves clear communication before, during, and after. Often, attendees aren't sure what to expect, so we have to make sure to set the tone before the call even happens. So I send an agenda 24 hours prior to the call and include the following. • What topics will be discussed • Questions to answer beforehand • Use cases if applicable Also, make sure to do some research about the company so you have context. No one likes an unprepared sales rep. During the call immediately set expectations. • Ask if they have a hard-stop • Refer back to the email to set the agenda for the call • Mention that you did some research and tell them what you found Be an active listener and ask deep discovery questions to uncover pain. As the call wraps up, make sure to leave 7-9 minutes to guide them through the next steps. Here is an example: "Typically, when we see a problem like this, we would most likely include (x person) and (y person) on the next call to discuss how we help in that area. Would Thursday at 10am EST work for you?" I book these meetings directly from Calendly's browser extension while still on the call because it's quick, smooth, and instant. Calendar invites are sent before we end the call so you remove the possibility of being ghosted after. We still have work to do after you nail down the next steps. We ain't done yet. Send a summary email, not to do more selling but to recap for accountability. • What their main goals/priorities are • Timeline • Next steps When you have a system to run better meetings, it leads to great results. P.S. Do you agree with this framework? #BetterMeetings

Reps will forget 70%+ of what they learn within a week of training (Gartner). A week! And it's 87% within a month. Your sales org is likely making huge investments in PipeGen right now. You're leveling up SDRs. Enabling AEs to self-source more pipeline through outbound. All of that work is a complete waste of time if you don't build in a "make it stick" rhythm. Here’s a 4-part framework we use to help our clients increase qualified opp creation by 20%+ on average: ✅ 1) Train The two most overlooked parts of training: simplicity and tailoring. Whatever you teach must be simple. We call this "eating complexity." Workflows and tools should be easy to use and follow. Second, the training must be tailored by segment and role. You can't give generic outbound/sales training to AEs, BDRs, and AMs. You can't give the same advice to an SMB and an enterprise rep. Reps should leave a session wondering, "How does this apply to me?" Do that work for them. ✅ 2) Practice Every training session should be interactive, workshop style. Retention is much higher when practice happens immediately after learning. Leverage breakout rooms during enablement sessions. Shoot for 10-15 min. of learning and then 10-15 minutes of doing. Managers should facilitate practice in part of their 1:1s and weekly team meetings. Bonus points if managers schedule a regular stand-up to practice new techniques. Stop practicing on prospects. ✅ 3) Observe The biggest mistake here: coaching reps based on their memory of what happened vs. what ACTUALLY happened. An unskilled rep is unconsciously incompetent. In other words, they don't know what they're not good at. You can't rely on a rep to tell you how things went, then coaching them to that. You need to watch it live. Outbound calls need to be recorded. Look at their emails. Every manager should spend deliberate time watching their reps out in the wild. ✅ 4) Coach This is where the magic happens. You need deliberate coaching during 1:1s. We recommend having at least a bi-weekly 1:1 that's dedicated to coaching vs. deal/pipeline reviews. Your managers need enablement on HOW to deliver great coaching. Spend time coaching the coach. ~~~ This 4-part framework has helped our clients like Shopify, Gong, Rippling, and more get great results from training programs. What'd I miss? Drop a comment below.

"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

Too many reps are still winging their meetings. They show up. They talk too much. They forget to follow up. And then they wonder why deals stall. The top reps I’ve trained over the years all have one thing in common: They don’t just HAVE better meetings, they RUN better meetings. Here’s what they do differently: • They send a shared agenda before every call • They follow the 40/40/20 structure to guide the conversation - 40% Discovery (focused on impact) - 40% Value Alignment (From the executives priorities down) - 20% Next Steps (dates, owners, action items) • They send summary emails with key take-aways and get the client to confirm it • They use tools like Otter.ai to automate the admin and focus on selling The best part? You can steal these frameworks for free. This is the Sales Conversation Playbook I built with Otter.ai: https://lnkd.in/eKxVwep4 It’s short, tactical, and loaded with tools you can use right now to increase conversion. Meetings don’t move deals. Clear next steps do. Use some of the tips and tools in this workbook to run your next call and let me know if it makes a difference. #MakeItHappen #MeetingExecution #sponsor #Discovery

Most sales meetings fail because of indigestion (too much info shared too quickly) NOT starvation (not enough info shared). Here are some ways to aid "digestion": 1. Send a meeting pre-read to your prospect. Nate Nasralla has some great content about "pre-meeting memos" 2. Frequently check for comprehension. Contrary to what your average sales influencer tells you, asking "does that make sense?" isn't gonna ruin your deal. 3. Better ways to check for comprehension: "How's this compare to what you're doing today?" or "What do you think the rest of the team will think of this?" 4. Read body language. If they look confused, they probably are. 5. Speak on ".8x speed" instead of 1.25x speed. This might be your 147th time explaining a concept, but it's the first time your prospect is hearing it. 6. Connect the dots for your prospect. When you show them a feature, explain how it's relevant to the situation they shared with you. 7. Speak their "language". If your prospect uses different words to describe a process/problem that aren't the exact words you're used to, it's OK to use their language to make things easier for them to understand. 8. The more you can customize your demo environment to show "their data" or situations tailored to theirs, the better. 9. Post-demo, instead of sending the full call recording, try sending a "highlight reel" with snippets from the call. 10. Not my idea, but Kyle Asay had a great post the other day about how one of his AEs will incorporate "demo time stamps" into a mutual action plan/POC to make it extremely easy for the prospect to find info. How else do you help your prospect "digest" information? 

This is the most underrated problem I've seen when trying to build or expand partnership GTM: Leadership is initially fully behind a new partnership, excited about its potential, but that enthusiasm never makes its way down to the sales teams who are expected to execute. Without alignment, even the best partnership can stall before it has a chance to succeed. Why does this happen? Sales teams are often focused on their core products, and if a partnership doesn’t clearly benefit them or fit into their day-to-day operations, it becomes an afterthought. To turn things around, you need to make sure your partnership incentives, compensation, and training are in lockstep with the teams that will be selling your product. Here’s how to align incentives and drive results: 1. Ensure your incentives are compelling enough for frontline teams. It’s not enough to excite leadership—sales teams need a clear, tangible reason to sell your product. - Introduce a financial incentive or bonus structure that’s competitive with what reps earn on their core products. This could be a one-time bonus for the first sale, or an ongoing commission that rewards consistent effort. -Tie the incentive to their existing sales goals. If your product helps them hit their targets more easily, they’ll naturally prioritize it. 2. Structure partner compensation to motivate co-selling. If your partner compensation doesn’t align with their core goals, they won’t push your product. - Design a compensation plan that aligns with both the partner’s and your business objectives. For instance, if your partner’s core offering is hardware, incentivize bundling your software as part of the sale to create a win-win situation. - Offer performance-based incentives that reward partners for hitting key milestones—whether that’s a certain number of units sold, a specific revenue target, or even customer engagement metrics. Keep it simple and measurable. 3. Provide consistent training and engagement so your product isn’t just another checkbox. Sales teams won’t advocate for your product if they don’t fully understand its value or how to sell it. - Develop ongoing, bite-sized training sessions that fit into their schedules. Instead of overwhelming them with lengthy sessions, focus on 15-minute, high-impact trainings that teach them how to identify the right opportunities. -Pair training with real-time support. Join sales calls, offer one-pagers, and provide direct assistance during key customer engagements. When they feel supported, they’re more likely to feel confident pushing your product. This kind of alignment can make the difference between a stalled partnership and a thriving one. When sales teams are motivated, equipped, and incentivized to sell your product, the partnership stops being just another checkbox—it becomes a key driver of growth.

Many sales managers are unknowingly killing the growth and independence of their reps. They think they're coaching, but they're actually fostering a toxic dependency that chokes potential. Here's how it happens ⬇️ Rep brings a stalled deal to their 1:1. Manager says: "Did you send the follow-up email?" Rep: "Yes." Manager: "Did you try calling?" Rep: "Yes." Manager: "What about LinkedIn?" Rep: "I'll try that." This manager thinks they're coaching. They're actually teaching their rep to be a task completion machine The rep leaves that conversation with a to-do list, not strategic thinking. Great sales managers ask completely different questions → What changed in their business that might affect this priority? → Who else might be influencing this decision that we haven't talked to? → What would have to be true for them to move forward next quarter instead of this quarter? These questions force reps to think like business consultants instead of activity generators. The goal isn't more touches. It's better understanding. Your 1:1s should build strategic thinking, not just drive task completion When reps understand buyer psychology, they can predict what will work. When they just follow activity checklists, they're always surprised by outcomes. Stop managing what reps do. Start developing how they think.

Day 43: Matching Sales Reps with the Right Prospects Using DISC Profiling When building a high-performing sales team, skill matters, but personality fit is just as crucial. The type of prospects your sales reps handle should align with their natural strengths. A great way to assess this is by using the DISC Personality Profile test. What is the DISC Personality Profile? The DISC model categorizes people into four personality types based on their behavior and communication style: ✅ D - Dominance (Results-Driven, Assertive, Competitive) ✔ Best for: High-ticket closers & fast decision-makers ✔ Works well with direct, no-nonsense prospects ✔ Tip: Keep pitches short, focus on ROI & logical benefits ✅ I - Influence (People-Oriented, Persuasive, Energetic) ✔ Best for: Warm leads & community-driven prospects ✔ Works well in networking, events, and social selling ✔ Tip: Use storytelling, case studies & relationship-building ✅ S - Steadiness (Patient, Loyal, Supportive) ✔ Best for: Long-term nurture sequences & consultative sales ✔ Works well with customers needing reassurance & trust-building ✔ Tip: Take a personalized approach, avoid aggressive closing tactics ✅ C - Conscientiousness (Detail-Oriented, Analytical, Structured) ✔ Best for: Selling complex solutions & high-risk investments ✔ Works well with logical thinkers & data-driven prospects ✔ Tip: Provide research, comparisons, and in-depth explanations How to Analyze DISC in Sales Hiring? 🔹 Run a DISC assessment before hiring to match reps with the right sales role 🔹 Observe their communication style during roleplays 🔹 Ensure their natural personality complements the type of leads they’ll handle ❓ What’s your DISC profile, and how has it helped you in sales? Comment below! 📌 Follow me for more sales leadership hacks, strategies for building an education business, and remote sales insights every Monday, Wednesday, and Thursday! #SalesLeadership #DISCProfile #SalesRecruiting #PersonalityFit #HighTicketSales #SalesPsychology

Most 1:1 meetings feel like a waste. But it’s not the meeting. It’s because nobody... Told either person what this meeting is actually supposed to do.   🚫 It is not a status update.  🚫 It is not a check-in box. It is the one place each week where someone should feel genuinely heard, helped, and pointed in the right direction. Every hollow one-on-one sends a quiet message to your team. That message is: I do not think this time matters. And people hear it. They stop bringing real problems. They stop sharing honest thoughts. They start looking for someone who actually wants to hear from them. That is how you lose great people without ever seeing it coming. Here is what a great one-on-one actually looks like from both sides: For managers, start here: This is not your meeting. It is theirs. Show up to serve, not to report. ✅ Keep it weekly. Reschedule. Never cancel. ✅ Private space. No phone. Full presence. ✅ Start human. Ask how they really are. ✅ Listen more than you talk. Every time. ✅ Ask: What do you need from me? ✅ Give specific feedback with real examples. ✅ Bring them into their own goal setting. ✅ Ask how you can be better for them. ✅ Take real notes and follow through on them. ✅ Celebrate actual wins, not just big ones. For employees, own this too: Walking in without an agenda means walking out without progress. ✅ Come with your own agenda always. ✅ Lead with a win and back it up with proof. ✅ Be specific about exactly where you need help. ✅ Bring long-term goals into the conversation. ✅ Ask directly about your development path. ✅ Name what feels unclear before it becomes a problem. ✅ Be honest about what is slowing you down. ✅ Ask for what you actually need out loud. ✅ If you feel unheard say it directly. ✅ Take real notes and act on them. ✅ Keep your manager updated between meetings. Your reset before the next one: ⇒ One win with real proof behind it. ⇒ One honest blocker to work through together. ⇒ One growth conversation to have out loud. ⇒ Clear actions before you leave the room. ⇒ Follow through before you meet again. The meeting is not the problem. The best thing a leader can do is make someone feel like their 30 minutes actually mattered. Do that consistently and people stop looking for the exit. 🎁 Want PDFs of my top infographics + growth tools? 👉 Go Here: https://lnkd.in/g2xbnwhp ______________________ 📚 Join my free workshop to build digital products that sell over and over. ➡️ Save your seat: https://lnkd.in/gNc9zSx6 _____________________ 🛠️ Want to build your own digital business? 🔥 I built something for you: https://lnkd.in/g69W4jPu Please repost to help others out there! ♻️