Lessons from 20 years in sales

Brandon outlines the seven hardest lessons he learned from a 20-year sales career:

1. It all starts with intent: People may judge your actions, but you have to live with your intentions. keep them pure.

2. You're a human first, professional second: Avoid the 24/7 hustle trap. work hard and smart based on your own principles.

3. Embrace long-term thinking: Patience pays off in the long run. remember to keep your intentions pure.

4. Make staying calm your superpower: Worrying changes nothing. stay calm when things go wrong.

5. Failure is just a data point: Reflect on failures to turn challenges into lessons.

6. To go far, you need high-quality systems: Good systems help you make better decisions with your time, energy, attention, and money.

7. The only scoreboard that matters is your own: Avoid comparisons. focus on being better than you were yesterday.

8 mistakes I made

Alex on eight mistakes he made as a sales rep and the lessons he learned:

1. Defensive reactions: When prospects challenged him, he got defensive. Using call recording software helped him learn from his calls.


2. More isn’t always better: He defaulted to making more calls and emails, burning leads. Instead, he should have improved his messaging.


3. Lack of preparation: He winged his calls, thinking he was naturally good at sales. Practicing would have made him more polished.


4. Poor qualification: He didn’t differentiate between almost qualified and actually qualified leads, wasting time on bad deals. Implementing a qualification framework is crucial.


5. Looking for shortcuts: He searched for hacks instead of putting in the hard work. Great sellers put in the effort to learn.


6. No documentation: He didn’t document his processes, making nothing repeatable and wasting time.


7. Lack of measurement: He didn’t measure his work, so he had no idea what was successful. Identifying what works is essential.


8. Self-criticism: He was hard on himself, never celebrating wins and dwelling on losses. Sales has ups and downs, and being kind to oneself is important.

Takeaway: Implement what you learn immediately and consistently until it becomes second nature.

Advice after 10 years in sales

Jacob’s key lessons from over 10 years of sales experience:

1. Know the business: understanding your prospect's business is essential.

2. Warm intros win: a warm introduction or referral beats mass prospecting messages.

3. Start multithreading early: engage multiple contacts before your first meeting.

4. Focus on outcomes: prospects care about outcomes, not your product.

5. Identify key roles: know the difference between coaches, champions, and detractors.

6. Rare compelling events: truly compelling events are uncommon.

7. Align with prospect timelines: their timeline matters more than yours.

8. Budget follows importance: budgets appear if the problem is critical.

9. Navigate pricing gates: have a plan to clear all pricing hurdles.

10. Involve legal resources: legal teams get involved only when deals are real.

11. Expect procurement demands: procurement will always ask for more.

12. Text with your champion: for big deals, maintain close contact with your champion.

13. Closing is just the start: closing a deal begins the next phase of the relationship.