[Flash] How Salesforce CEO Mentors Leaders

Benioff began his response by describing the endless amount of information that CEOs navigate daily: emails, texts, meetings, articles, reports, research, news, and updates.

To quickly navigate the overload, leaders tend to lean heavily on their vast experience and expertise to solve problems, often failing to consider or acknowledge new ideas or approaches.

Unfortunately, this I’m-an-expert approach favors efficiency over possibility.

To combat the hubris of previous experience, Benioff revealed his commitment to shoshin.

A Zen Buddhist concept, “shoshin” means having a beginner’s mind. It entails looking at a problem or a situation through the lens of a newcomer.

With shoshin, we are open, eager to discover, and free of preconceptions, assumptions, and expectations – just like beginners. With this frame of mind, anything is possible!

Imagine being new to a project, a problem, or a puzzle – the mind is filled with wonder and curiosity.

Benioff applies this same concept to mentoring.

When a leader calls Benioff for advice, he practices shoshin to ensure he meets the conversation with possibility, focusing first on the person, not the problem. 

Here’s how he unfolds a mentoring conversation:

• “Let’s start with your level of mindfulness and your mindset. Where are you?
• “What do you really want? That is the number one question to start.
• “What’s important to you?
• “Let’s start there with your vision and your values. That is where I want to spend the time with you right now.”

Benioff’s mentoring approach is like a pause button – encouraging people to see themselves first.

Mentoring is not about having all the answers. It’s about asking questions that prompt a change in thinking.

Benioff’s questions pause the propensity to fix problems with the been-there-done-it experience. He is unearthing a mentee’s core which then serves as a beacon for any advice, ideas, and guidance.

When a mentee asks for our support, we too risk leaning on our experience instead of exploring with our curiosity. Our desire to immediately fix a problem can drive us to offer a solution impulsively.

Where are you?
What do you hope for? 
What’s most important to you?

But starting with these three questions, we can create conversations that demand a beginner’s mind – ours and our mentees’.

© 2025. Ann Tardy and MentorLead. www.mentorlead.com. All Rights Reserved.