Sales Mindset Development

This might be the most important career advice in sales. Because here's the truth: Your reputation travels faster than you do. Your name comes up more than you think. Decisions about your future happen without you. Every. Single. Day. Think about it... That promotion you're hoping for? Being discussed in rooms you're not in. That big account you want to work? Being decided by people you've never met. That leadership opportunity? Being influenced by what others say about you. The uncomfortable truth? Success in sales isn't just about crushing quota. It's about having advocates. People who say "Give them a shot" when others doubt. People who defend your approach when it's questioned. People who mention your wins when you're not around. Here's what ACTUALLY happens when you have real advocates: ↳ Opportunities find you before they're posted ↳ Your mistakes get context, not just criticism ↳ Your ideas get championed, not stolen ↳ Your growth gets fast-tracked, not delayed ↳ Your reputation becomes your strongest asset But here's the part most people miss: To have people fight for you... You need to fight for others first. That SDR grinding it out? Mention their progress in the team meeting. That peer who helped you close a deal? Make sure leadership knows. That manager who coached you? Tell their boss what it meant. Because advocacy isn't luck. It's reciprocity. The rep everyone wants on their team? They've been building others up for years. The manager everyone respects? They've been defending their people consistently. The leader everyone follows? They've been fighting battles for others quietly. Here's what fighting for others ACTUALLY looks like: When someone's not in the room: - Correct misconceptions about them - Highlight their strengths - Share their wins - Provide context for their challenges When opportunities arise: - Recommend them even if it doesn't benefit you - Connect them with the right people - Put their name forward - Open doors they can't open alone The magic of advocacy in sales? It compounds. Every person you genuinely support becomes part of your network. Every battle you fight for someone builds trust. Every time you elevate others, you elevate yourself. Not through manipulation. Through genuine support. So ask yourself: Who are you fighting for when they're not around? Whose potential are you highlighting? Whose success are you championing? Because the people who win biggest in sales aren't just the best closers. Be the person who fights for others. Watch how many start fighting for you. Your career will never be the same.

“Josh, I’m afraid to cold call.” Fear comes from feeling like you’re trying to get something—a meeting, a referral, or a sale. It doesn’t feel good to come from a place of taking. If you don’t fully believe in what you’re offering, it feels like you’re trying to trick someone into giving you their time. You feel inauthentic. And that’s where the anxiety creeps in. But when you focus on giving, the fear fades. Imagine you had the cure for cancer. Would you hesitate to cold call someone? Absolutely not. You’d feel an urgent need to share it because you’d know the value you’re bringing. The same principle applies to cold calling. If you believe in your product and its ability to solve real problems, your mindset shifts. You’re not tricking anyone—you’re offering something that could genuinely help them. Here’s the key: let go of the outcome. Problems only matter if they matter to the prospect. Instead of pitching, ask a question that highlights a potential issue, like: “When you bring groceries up to your 5th-floor apartment, do you make multiple trips, or do you use a foldable wagon to carry everything up at once?” Then lean back. Let them reflect. When you approach a call with a mindset of giving and detach from the result, the fear melts away. And if you’re still afraid? That’s okay. Do it afraid.

When I speak with people, especially in the Family Office world, the first thought on my mind is how I can help them. Sometimes that means introducing one Family Office to another, connecting people who share values, or sharing knowledge without expecting anything in return. These contributions compound over time and return in powerful ways. In this community, relationships come before transactions. The first questions are about trust, integrity, and whether values align. Once that foundation is in place, everything else follows. Offering value without expectation changes the dynamic. A thoughtful introduction, a timely perspective, or even the willingness to listen builds trust faster than a pitch ever could. Over time, these gestures create reputations that open doors and deepen partnerships. The principle is simple. The more you give, the more you get. Generosity builds momentum, signals authenticity, and encourages others to share opportunities and build together. This matters even more as the next generation steps forward. They care deeply about values, impact, and the character of the people they work with. Aligning with that mindset requires consistency, honesty, and the willingness to give first. By focusing on what you can contribute, you strengthen relationships and create opportunities that last. In the Family Office world, giving builds trust, and trust remains the currency that matters most.

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? 

Long before Google, I had a student job at the biggest toy store in Europe, Hamleys of London. Specifically, the one in Regent Street. I was 24, working mostly on commission, selling the Puzzle Car – an interactive jigsaw puzzle. At first, I found it challenging to get out of my comfort zone to stop people so I could pitch the toy. I’d do the demonstration, explain what it does, and watch people smile, nod—and walk away. No sale. But I paid attention. I started noticing patterns. Some people were drawn in by the movement of the toy itself. Others needed a push—a story about how their kids would love it, or how it was the perfect gift. And then there was the biggest sales driver of all: crowds. When one person bought, suddenly, three more wanted one too. If a crowd gathered, more people stopped to watch. And the more people watched, the more people bought. It was my first lesson in FOMO and social proof—and it wouldn’t be my last. But beyond that, selling toys at Hamleys turned out to be a crash course in business, leadership, and startups. Here are 5 lessons that still stick with me today: 1 – Storytelling sells People don’t buy products; they buy emotions, experiences, and stories. The best pitches aren’t about features—they’re about making people feel something. 2 – Rejection is part of the process For every ten people who watched my demo, only one would buy. Sound familiar? Founders hear "no" way more than "yes." The trick is to keep going and not take it personally. 3 – Know your audience Parents wanted to hear how educational and safe the toy was for their kids. Kids just wanted to see it move. The message mattered as much as the product. 4 – Energy matters If I looked bored or unmotivated, people kept walking. But when I was excited, when I believed in what I was selling, people stopped to listen. Whether you’re leading a team, pitching investors, or selling a product, your energy is contagious. 5 – You eat what you kill Working on commission meant no guaranteed paycheck. If I didn’t sell, I didn’t earn. It was a powerful lesson in accountability—something every founder understands. No one is coming to save you. You have to make it happen. Looking back, I didn’t know this job would teach me so much about business, startups, and leadership. But the fundamentals are the same, whether you’re selling a toy or building a company. What was your first job, and what did it teach you?

Using Story to Sell: This simple shift can change everything for your sales team. Because of pressures from quotas, salespeople often walk into meetings thinking about how they can get what THEY want out of it (a sale) rather than how they can help THE CUSTOMER get what they want. This will actually cause fewer sales because salespeople don't truly understand how they can help the customer overcome a problem or achieve a goal. But in reality, you and your product are the MENTOR and your customer is the HERO. In classic story archetypes, the mentor is the person who helps the hero get "unstuck". They give them a magical gift or a special tool that helps the hero forge ahead on their journey. (Think about how Obi-Wan gave Luke a lightsaber.) This is where an empathy walk becomes your secret weapon. Airbnb transformed their entire strategy after doing an empathy walk. They mapped out their customers' average day step-by-step and asked at each point: "Where does our customer get stuck? How can our product help them get unstuck?" This simple exercise revealed something crucial they'd missed...they needed a mobile-first strategy. You can apply this same principle to your sales conversations: 1. Map your customer's journey before your next meeting 2. Identify the exact moments where they struggle 3. Show how your product (the magical gift or special tool) helps them overcome these specific obstacles When you truly understand where your customer gets stuck, you can position your product as the perfect tool to help them succeed. And when you help heroes succeed, they remain loyal to you forever. #SalesTraining #EmpathyInSales #SalesStrategy

Want to stay motivated every single day? Borrow a strategy from Harvard. Then borrow another from stand up comedy. Together, they’re a powerhouse for momentum, motivation, and mastery. Here’s how it works: Let’s start with Harvard. Researcher Teresa Amabile studied 12,000 daily work diaries across 8 companies. She wanted to know: What truly motivates people on a day to day basis? What she found changed how we understand drive. The #1 driver of daily motivation wasn’t: Money Praise Perks It was progress. The days people made progress on meaningful work were the days they felt the best. Progress isn’t a luxury. It’s a psychological necessity. So how do we make progress feel visible especially on days when it’s not? Use a “Progress Ritual.” → At the end of the day, pause. → Write down 3 small ways you moved forward. → That’s it. No fanfare. Just ritual. This works because we rarely notice our progress in real time. It gets buried under busyness, meetings, and mental noise. The act of looking back gives your brain the reward it needs to keep going. Momentum builds from meaning. Now let’s add some comedy. Young Jerry Seinfeld had one goal: write new material every day. To stay on track, he created a brilliant system. Each day he wrote, he put a big red X on his calendar. Soon, a chain of Xs formed. And here’s the key: Don’t break the chain. One red X becomes two. Two becomes ten. Ten becomes identity. Whether you’re writing, coding, or training Daily action + visual chain = long-term motivation. Summary: The Two-Part Motivation System From Harvard: Record 3 ways you made progress each day. From Seinfeld: Mark an X for each day you show up then don’t break the chain. Progress fuels purpose. Consistency fuels confidence. Apply both and you’ll stay on track especially on the tough days. Because when your days get better, your weeks get better. When your weeks get better, your months get better. When your months get better, your life gets better. It starts with one small win today.

Sales is unpredictable. You’re responsible for a revenue target, but at the end of the day, you’re heavily dependent on your customer to make that revenue happen. However, the best Sales leaders know that the game isn’t about waiting for customers to take action - it’s about focusing on what you can control. And what you can control is how much you help your customers. Instead of obsessing over revenue numbers alone, shift your focus to tracking "help" metrics. Ask yourself: How many customers did your team call last week? How many did they reach out to via email? How many in-person meetings were conducted? How many follow-ups happened? When a customer called your Salesperson, did they pick up the call and solve the issue? Are your salespeople equipped with the right knowledge to truly help? These "help" metrics give you a better picture of how well your team is serving your customers. The more your team helps, the more trust they build – and the more that trust translates to revenue. Sales isn’t just about tracking revenue. Sales is about helping customers solve their problems. When your team is consistently there to guide, assist, and deliver value, the revenue will naturally follow. So, if you're a Sales leader, remember: Focus on helping. The numbers will take care of themselves.

Over 20 years of running companies, I’ve seen three traits that consistently separate the top salespeople: volume of activity, personalized outreach, and delivering value in every interaction. In a world of AI and automation, these things are more important than ever. Volume of activity There is a strong correlation between the number of calls, emails, and LinkedIn messages a salesperson sends and the number of meetings they book. That was true 20 years ago and it’s true today. At my first company, we didn’t have dialers. Reps manually punched in every number, I know… old school. One rep asked for a headset so he could move faster. He instantly doubled his daily dials and exceeded every goal we set. Today, there are more channels, more tools and more noise than ever, but the best reps know how to leverage automation to consistently execute a high volume of activities against the right accounts. Personalized outreach This is important because just pure volume isn't going to do it. You need to have strong personalization to your outreach to get people's attention because so much is being written by AI, is templated, etc. The best reps do real research on their prospects and use it to tailor their message. This might include referencing a shared connection, a recent announcement, or even a personal interest (I’ve seen reps find crazy stuff about prospects with some basic internet stalking). One of the best outreaches I ever received came from a rep at a bank who had been trying to get my attention. He sent a package with a framed New York Times article I was featured in, along with a handwritten note about why it resonated with him. He showed me I wasn’t just a name on a list. I had to take the meeting. Value in every interaction High activity and personalization go a long way, but the best reps consistently bring value to every conversation. That might mean sharing relevant trends, customer stories, or internal research. Most reps forget that even if they’ve never done the job their prospect does, they speak to more people in that role than most practitioners ever do. Sometimes it means connecting prospects with people or ideas they wouldn’t otherwise access, like the rep’s CEO or a high-profile customer. One of my top reps had a gift for becoming a kind of therapist. She would listen closely, reflect what she was hearing, and share examples of others facing similar challenges. It helped prospects feel understood. But all of it has to tie back to the value your company and product can deliver. When reps get this right, prospects actually look forward to their calls. The most interesting thing is that I have been saying this for many years to every rep I work with and only a very small portion will actually do these things. The truth is that none of this is easy. It takes time, effort, and discipline. But these are the three things that set the best apart.