The Hidden Work of Successful Salespeople

I just analyzed the calendars of 50 top performing sales reps. The difference between quota crushers and quota missers isn't what you think. It's not their territory. Not their product. Not their comp plan. → It's how they structure their TIME. After a decade coaching thousands of sales professionals I've noticed something. High performers don't work more hours. They work different hours. They obsess over IPAs. Income Producing Activities. Average reps spend over half their week on admin garbage. Top earners ruthlessly protect time for revenue generating work. I recently tracked my own time for two full weeks. Down to 15 minute blocks. The results shocked me (Yes, I’m still able to shock myself sometimes). Even though I teach this stuff I was spending 35% of my week on $20 per hour tasks instead of $2,000 per hour activities. I was stepping over hundred dollar bills to pick up pennies. Here's exactly how elite sales performers structure their week. Increasing pipeline - 25 to 30% of time Cold outreach that actually converts Social selling that builds real authority Discovery calls that uncover massive pain Creating opportunities not just conversations Progressing pipeline - 25 to 30% of time Moving deals forward with clear purpose Meeting key stakeholders Running customized demos Building business cases that sell themselves Closing pipeline - 15 to 20% of time Negotiating from a position of strength Handling objections before they surface Working legal and procurement strategically Actually asking for the business Upgrading skills - 15 to 20% of time Mastering objection handling frameworks Improving discovery techniques Studying influence and persuasion Learning from top performers Here's how to reclaim your time starting today. Step 1. Run a brutal time audit Track every 15 to 30 minutes for one full week. No lying to yourself. No rounding up. Just raw data on where your time actually goes. Step 2 . Categorize every single activity Time wasting activities that cost you money Low value admin worth $20 per hour Core selling activities worth $200 per hour High leverage skills worth $500 plus per hour Step 3. Calculate your IPA percentage What percentage of your week is spent directly generating revenue? If it's under 75% you're leaving massive money on the table. Step 4. Eliminate, automate, delegate Eliminate the zero dollar per hour activities completely Automate the repetitive busywork Delegate the necessary but low leverage tasks I hired an EA after realizing I was wasting 14 plus hours weekly on tasks I could delegate for $25 per hour. That's $28,000 in opportunity cost every single week. The math is brutally simple. $20 per hour tasks times 14 hours equals $280 value created $2,000 per hour tasks times 14 hours equals $28,000 value created What if the biggest lever to grow your sales income isn’t what you sell - but how you spend your time? ⏳ I unpacked the whole strategy in the comments 👀

Coffee is for closers. That line, and the toxic bravado behind it, needs to go. The best consultants and salespeople don’t sell. They start with one simple question: “Why?” And The Wolf of Wall Street is not a how-to sales guide. It’s a cautionary tale soaked in ego and adrenaline. Glengarry Glen Ross? Same thing. A masterclass in manipulation and moral bankruptcy, yet somehow these warped tactics, fast talk, pressure plays, "always be closing" still show up in sales training, and yes, recruitment floors. The recruitment industry, like it's close cousin real estate, is littered with outdated tropes: “Sell the pen.” “ABC: Always Be closing.” “Dominate the room.” Say whatever it takes to close the deal. These tactics are not just outdated. They’re shallow. Real influence doesn’t come from how well you pitch, post, or promote. It comes from how well you listen and whether what you say is backed by substance. Take “Eddie,” a self-proclaimed million-dollar biller with stories spanning Manhattan, London, and beyond. Mate, we all know it’s smoke and mirrors. A performance. You aren’t Brisbane’s own James Bond. The truth? -- The best salespeople don’t push. They pull. -- They don’t dominate the room. They open it up. -- They don’t talk more. They listen better. But not just any questions. They ask the ones no one else dares to. The ones that peel back assumptions, uncover motivations, get to the root of the problem. Most people ask what. Good people ask how. The best ask "why." Why? Because “why” changes the conversation. It unlocks purpose. Invites honesty and builds trust. “Why did that matter to you?” “Why do you feel that way?” “Why” is a shortcut to the truth. I remember sitting in a team meeting years ago. Nick, a sharp and well-respected colleague, was pitching a cost-saving plan that completely missed the mark for our customers. Instead of challenging him directly, I just kept asking “Why?” Five times. Eventually, he paused, and concluded there were better, more customer-focused options. That’s the power of better questions. Not to trap someone, but to help them see more clearly. When you lead with curiosity, you’re building connection. You’re showing someone you care about them, not just the transaction. And that’s where trust happens. That’s what actually drives referrals, sales, and loyalty. Take it from me, someone who spent +20 years getting this wrong. It turns out that the sale is just the byproduct. The real win? Be the person who gets it. Who listens when others talk. Who connects instead of convinces. Be the person who gives it all away for "free." Because you know it will come back around anyway. So next time you’re in a conversation, sales or otherwise, ditch the “pitch script.” Get curious. Ask better questions. Go where others don’t. And above all, ask "Why?" The real magic in winning the deal, doesn't happen when you sell. It happens when you understand. Enjoy the coffee.

Want to know why top performers close 2-3x more deals than average reps? It's not that they're smarter. It's that they've mastered deep work. After studying hundreds of high-performing sellers, I've found one consistent pattern: They protect their prime selling hours like their life depends on it. Most reps are drowning in shallow work, constantly switching between email, Slack, CRM updates, and social media. Each task switch costs you 23 minutes of focused energy. The result is a day filled with activity but empty of results. Here's how innovative sellers are implementing deep work: 1️⃣ Power Blocks They schedule 90-minute uninterrupted blocks for their most important selling activities. No email. No Slack. No phone. Just focused execution on revenue-generating work. 2️⃣ Energy Management They align their most important tasks with their peak energy hours. For most, that's 9-11 AM, not 3 PM after back-to-back meetings. 3️⃣ AI-Powered Prep They leverage AI to prepare for sales calls in half the time. "I feed the AI my call notes, recent news, and past objections. It gives me a hyper-focused prep document in 5 minutes instead of 45." 4️⃣ Elimination Before Optimization Before trying to get faster at tasks, they ask: "Does this task even need to exist?" You can't optimize what should be eliminated. 5️⃣ Digital Minimalism They turn off all notifications during selling hours. No Slack pings. No email popups. No LinkedIn alerts. The sellers implementing these practices aren't working more hours. They're just getting 3x more value from the hours they work. Most sales organizations obsess over activity metrics while ignoring the quality of focus behind them. What would happen if you protected just one 90-minute deep work block every day?

I’ve seen commission payouts for 100s of enterprise salespeople. Every AE earning over $750,000/yr had mastered 7 key selling skills: 1. Ruthless Disqualification Great selling starts with spending time with prospects who can buy and be successful with their solution. This means the most important thing is recognizing if a “love connection” is possible. Does the account match the ICP? Is there a compelling event? Are the right resources in place to be successful? If yes, they invest time. If not, they recognize it quickly and put it in nurture. 2. Always-on Discovery Big sales come from building big value, and big value comes from constantly doing discovery and understanding client needs. Discovery isn’t something to rush through, it’s always on, every conversation should involve some discovery. You can also uncover another clue on how to make your client successful. 3. Deliver Value Up Top (And Often) Having said that… salespeople can make the mistake of focusing *exclusively* on discovery early, because they know it’s important. You have to balance discovery with bringing value, or clients get bored and feel like it’s a one-sided relationship. Great salespeople bring value with unique perspectives on the market, competitors, the clients' challenges, etc. 4. Build a Reference Network of Similar Buyers The highest earners build a network of similar buyers, who trust them, and who are available to connect with new prospects. This is a super-advanced skill which takes time to cultivate, but when in place is game-changing. 5. Give To Get Mentality Prospects will ask for a lot through a sales cycle. On one hand, this show’s engagement, on the other, it does not mean they are committing the resources necessary to become a customer. Examples: When a prospect asks for a demo, ask to make sure all the right people are going to be present to evaluate. When a prospect asks for a trial, ask for the right level of executive engagement to make sure it’s set up for success. 6. Confidence To Ask For A Big (Fair) Numbers Too many salespeople are quick to discount. They’ve spent months building value, believe in a solution that’s important for their clients, and then forget about all the value. This hurts them, the company they work for, and ultimately their customer because they’ve created a dynamic that isn’t sustainable, a losing money proposition. Ask for what’s fair to support a win/win sustainable relationship with your customer. 7. Refuses To Ghost After the Sale The best salespeople are available and stay involved after the sale to make sure the client is wildly successful. This gives them credibility in understanding how to make others successful, builds their network, and makes their companies successful. --- What do YOU think are high W2 enterprise sales skills?

One sales conversation can reveal a belief someone didn’t even realize they had. I once coached a rep I’ll call Sarah who consistently avoided conversations about price. Whenever the topic came up she redirected the discussion, offered a discount, or delayed the conversation entirely. At first it looked like a negotiation problem. But when we talked privately, the real issue surfaced. Growing up, money had always been a source of stress in her home. Talking about money felt uncomfortable, and charging someone thousands of dollars felt almost wrong. That belief quietly followed her into her career. Once she recognized it, everything changed. Her confidence shifted, her conversations improved, and her results followed soon after. Sales behavior almost always has a belief underneath it. When the belief shifts, the behavior often follows. What belief might be quietly shaping the way you or your team sells? 

The greatest irony of sales: The person who needs the deal the least is the one most likely to win it. The more you chase, the faster it runs away. I know that sounds crazy. Because most of us get into sales needing to close. We need the income. We need to hit quota. We need to keep our jobs. But here’s the truth: when you show up needy, you give off commission breath. And commission breath repels clients faster than anything. Why? Because the energy shifts from them to you. You stop listening. You stop being curious. You start trying to convince. And nothing turns a buyer off faster. The top 1% of salespeople I coach all have this in common: They detach from the outcome. They walk into meetings not trying to impress—but to understand. That’s why the biggest deals I ever closed weren’t me “selling hard.” They were me sitting at dinner with executives, asking where they wanted to go, what was in the way, and whether I could help. No pressure. No desperation. Just curiosity and service. So how do you detach when you really do need the money? Here’s what works: 1. Separate wants vs. needs. You don’t need every deal. You want them. Detach from the lifestyle expenses that trick you into thinking you’re desperate. 2. Know your financial runway. Calculate your net worth against your monthly cost of living. Most reps realize they’re not as close to the edge as they fear. That perspective alone removes pressure. 3. Shift your focus outward. The fastest way to get what you want is to help others get what they want. Zig Ziglar nailed it. 4. Anchor your worth in values—not quota. I know I’m valuable because I’m honest, disciplined, and I do the right thing—not because of my number. And ironically, the results always follow when I operate this way. 5. Sales is a transfer of energy. If your energy screams “I need this,” the buyer will run. If your energy says, “I’m here to help,” the buyer will lean in. TAKEAWAY: The less you need the deal, the more likely you’ll win it. Detach from outcomes. Detach from desperation. Detach from ego. Show up curious. Show up humble. Show up to serve. That’s what sales mastery really looks like. Service > Scarcity

Salespeople may be some of the most misunderstood professionals in business. Too often, sales is reduced to persuasion, pressure, or performance theater. But neuroscience tells a different story. The human brain is wired to detect threat before it detects value. Which means if a buyer feels pressured, skeptical, or misunderstood, the conversation is already working against you. The best sales professionals aren’t pushing people toward a decision, they’re creating the conditions for trust. They’re reading emotion, managing uncertainty, and asking questions that create relevance. They are helping buyers make sense of risk, change, and competing priorities. And they do it while carrying constant pressure themselves: •quota •rejection •uncertainty •high stakes conversations where every interaction REALLY matters That requires far more than charisma...it requires emotional regulation, resilience, and the ability to communicate in a way that makes another human feel psychologically safe. Great sales isn’t about convincing, it’s about reducing cognitive friction. And reducing cognitive friction helps build trust.

I have been a top sales producer throughout my career, but I was not my company’s best seller. Here’s the truth: There were much better: • Presenters • Negotiators • Communicators The skills that typically get associated with top sales performance tend to deal with what you do in the moment with a prospect: • Charm • Charisma • Relationships I'm good enough at those things, but what I like to think separated me was my ability to do deep work outside of those client-facing interactions. It was in the quiet moments when I could craft a proposal that read like a compelling story or do the proper research about parts of their business that needed my help. That's what produced the strategic body of work for my success with new companies and how and why introverted-leaning sellers can gain an advantage. If I did not work diligently to protect this time, to create those quiet moments to craft something special—everybody would've missed out—my prospects, my company, and me. This is why changing the nature of how we work, not just in sales, but in all roles, is critically important. 🐝

🎯Sales is the hardest job that looks easy. Busting a common myth that sales is all about talking and convincing, people often notice the wins, the confidence, the commission, and the closed deals, but rarely see the unanswered emails, the follow ups that go nowhere, or the deals that fall apart at the final step. Great sales is not loud or aggressive. It is about listening more than talking and understanding a problem, sometimes better than the person describing it. It shows up as calm, thoughtful conversations backed by preparation, rejection, and discipline. The irony is that when sales is done right, it feels effortless. But that effortlessness is earned through consistency, emotional control, and showing up every day even when outcomes are uncertain. Sales is not about convincing people into something. It is about earning trust again and again. That is why it looks easy, and why it never truly is. Follow me for more posts and insights!

Here’s a harsh truth: desperation smells. And in sales, it reeks. The worst salespeople chase. They try to convince buyers they have a problem when they don’t. It’s uncomfortable, off-putting, and - let’s be honest - ineffective. The best salespeople? They never do this. They operate from a place of strength, not neediness. When a buyer says, “We’re good, no problem here,” they don’t push. They respond with something like: "Sounds like things are going really well on your end. If that’s the case, I’m not sure we can help. Does that check out, or am I missing something?" And here’s where the magic happens: - The buyer agrees. “Yep, everything’s good on our side.” Perfect. You’ve just saved yourself time and energy. No forcing square pegs into round holes. Move on to the next opportunity. - The buyer opens up. “Actually, now that you mention it, there is something we’re struggling with…” Their defenses drop. Sales resistance melts away. Suddenly, it’s no longer about you selling - it’s about them sharing. The best salespeople understand that sales isn’t about convincing - it’s about uncovering. - They know when to walk away. - They’re curious, not pushy. - They understand the subtle social dynamics that make buyers feel comfortable enough to trust them. Desperation? It’s a deal-killer. But confidence? That’s a deal-closer. Selling from a place of strength means knowing your worth, respecting the buyer’s time, and focusing on the right opportunities - not forcing the wrong ones.