Lessons from Scott Leese

A titan in the world of sales, Scott Leese is a six-time sales leader, three-time author, and strategic advisor who has left an indelible mark on the industry. His career is a testament to his deeply held beliefs in process, mindset, and people-centric leadership. Having battled and overcome significant personal health challenges, Leese brings a unique sense of urgency and appreciation for opportunity to his work, inspiring a generation of sales professionals to achieve greatness. [1][2]

On Sales Process and Strategy

The cornerstone of Scott Leese's philosophy is an unwavering commitment to a defined and repeatable sales process. He advocates for a structured approach that removes guesswork and empowers teams to perform consistently.

Quotes:

"Most startups lack a structured sales motion. They don't have a playbook, a process, or a strategy. They run out of momentum just winging it because winging it doesn't scale." [1]
"Find pain. Build value. Talk about what the product does. In that order. Do not try to sell it in any other order. Your results will suffer." [3]
"Once you find a system that works, stick with it. As obvious as it may sound, too often we want to tinker with things out of boredom." [4]
"Prescription without diagnosis is malpractice." [5]
"I have to assume that i'm a better salesperson. than people who are just coming up. so i can't just take what's in my head and how i would pitch. it put it on paper and expect everybody else to execute. it...i got to dumb it down and simplify it a little bit." [6]
"The process was put in place for a reason, and if done correctly, it works." [5]
"I just assume everybody's going to tell me no. and that keeps me hungry. all the time." [6]
"Don't shy away from [objections]. Lean directly into them and have the conversations about known challenges as early in the process as possible." [4]
"The buyer knows every objection they're going to come up with before they ever decided to talk to you." [4]
"The Process provides a strategy to follow. It's a road map and a guide to help you get to where you want to go."

Learnings:

Document Everything: The biggest mistake early-stage companies make is not documenting their sales process. Create a playbook for everything from outreach and demos to follow-ups and contract sending. [7]
Simplify for Scalability: A sales process should be simple enough for the majority of the team to execute successfully, not just the top performers. [6]
The 10x Pipeline Rule: Always aim to have 10 times the pipeline you need to close. This creates a buffer and keeps the focus on continuous prospecting. [6]
Focus on the "Why": The key event in any sales cycle is uncovering why the prospect needs to solve their problem. [4]
Strip Out Complexity: Focus on solving the top 3-4 pain points for your ideal customer profile instead of overwhelming them with every feature. [4]
Early-Stage Work Should Optimize for Scale: The foundational work you do in the early days of a startup should be done with future scalability in mind. [1]
Just Ask for Referrals: The simplest way to get referrals is to ask for them at the point of sale when the customer is excited about the product. [8]
The "Learned, Earned, and Burned" Framework: Evaluate your career progression by asking if you've learned all you can, earned all you can, or if you're being burned by your current role. [9]

On Sales Leadership and Team Building

Leese's approach to leadership is rooted in genuine care, empathy, and a commitment to the personal and professional growth of his team members.

Quotes:

"I don't really believe anybody cares that much about their job or hitting quota. They care about what those things can do for them or their family or their loved ones." [8]
"If I can help Bill achieve his goals, and he moves on in two years because we don't have the right role for him, I've still done my job as a leader." [10]
"Stop asking your team to go into so many meetings and report on meaningless KPIs...Instead, ask your team what blockers they have and what's holding them back from doing twice as good a job." [8]
"You can't turn water into wine." [1]
"I think I would do better with a bad product and good people than a really good product and bad people." [6]
"It's not about me hitting numbers or looking good. If I can help my team members get where they want to go, that's success." [10]
"Being a great leader requires more than just having the best strategies and techniques. It's also about being open and sharing your journey, both the good and the bad." [11]
"Not everybody can move up with you, so you need to re-evaluate the people you're spending time with continually." [4]
"The best test to find. out if somebody's ready for leadership. is tell them you're thinking about them in terms of a leadership. role...what happens is most people just fall to bits." [6]

Learnings:

Tap into Individual Motivations: A good sales leader has deep, beyond-the-surface conversations to understand what truly drives each person on their team. [8]
Vet the Company, Product, and Founder: Before joining a company, thoroughly vet the leadership and the product to ensure alignment and avoid situations where you can't succeed. [1][8]
Hire for Passion and Motivation: Look for people who are passionate about the business and have a high level of intrinsic motivation. You can often gauge this by asking what they do in their spare time. [6]
Prioritize People Over Product: A team of great people can often outperform a great product with a mediocre team. [6]
Delegate Effectively: Understand your strengths and weaknesses and delegate tasks you're not good at or don't enjoy, such as sales operations.
Don't Over-Index on Industry Experience: When hiring, prioritize a candidate's drive, build-mentality, and experience at a similar company stage over specific industry experience. [12]
Give People a Chance: Be willing to take a chance on individuals who may not have the exact experience but demonstrate the potential to succeed in a role. [13]
Run One-on-Ones Differently: Start one-on-ones by asking about the individual's life and well-being before diving into pipeline and forecasts. [7]

On Mindset and Personal Development

Leese's personal journey has profoundly shaped his views on mindset, resilience, and the power of effort.

Quotes:

"You can control your efforts and that oftentimes is the differentiator between, who does well and who doesn't and who succeeds and who does not." [14]
"My only way to gain an edge was to outwork everybody." [14]
"I gained an extreme sense of urgency and appreciation for the limited number of opportunities we have in this world. So I just think I care more than most people." [1]
"Success boils down to one question: 'How bad do you want to make it happen?'" [15]
"The only difference between successful people and less successful people is how they handle those changes." [3]
"You have to be willing to do things you've never done before." [3]
"I focus on the outcomes, not how I get there, and I take action before I allow my head to overthink things." [1]
"One of the hardest parts of sales is separating what you do from who you are." [16]
"You almost have to have some element of delusional confidence... to become a VP of sales." [12]

Learnings:

Effort is the Great Equalizer: When you feel you lack experience or talent, you can compensate by outworking everyone else. [14]
Embrace an "Addiction" to the Process: Focus on consistently executing the steps of your process rather than obsessing over the results. The results will follow. [2]
Develop a Mindset of Success: Actively seek out opportunities to learn and network with peers and leaders to cultivate a growth-oriented mindset. [5]
Listen Actively: In a world where our minds wander, the ability to truly listen and understand before prescribing a solution is a superpower. [5]
Don't Get Attached to Deals: Assume every deal might fall through to maintain your hunger for prospecting and avoid complacency. [6]
Find a Peer to Talk To: The role of a sales leader can be isolating. It's crucial to have another practitioner to talk to who understands the pressures and challenges. [9]

Scott Leese's teachings provide a comprehensive blueprint for success in sales, emphasizing that with the right process, a relentless work ethic, and a genuine commitment to people, anyone can achieve extraordinary results.

Learn more:

Lessons from Scott Leese

On Sales Process and Strategy

On Sales Leadership and Team Building

On Mindset and Personal Development

Written by Antoine Buteau

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