When I served on the Board at Oracle, I worked alongside a Sales VP who was remarkably sharp at sharing practical wisdom. He once dropped a truth on me that stuck: the higher you climb up the corporate ladder and the further removed you get from actual customers, the more disconnected you become from the day-to-day reality of the business.
He refused to operate from an ivory tower. Instead, he stayed grounded through three deliberate habits:
Insisting on customer face-time: He constantly asked salespeople if he could join their customer meetings. Sales reps initially hated it, assuming he was spying on them, and we all know how customer dynamics shift when a senior executive enters the room, as clients naturally pivot to address the highest-ranking person. But for him, direct market proximity was non-negotiable.
Walking the floor: He would regularly wander around, sit down with reps at their desks, and ask a simple, open question: "So, what’s happening?" It kept his finger on the pulse of the team's daily friction.
Leading from the front: During a campaign to drive CRM adoption across the org, he didn't delegate the rollout. When it came time for the live demo, it wasn't the head of pre-sales presenting. The Sales VP personally stood up, explained why accurate CRM data mattered to the business, and then walked the entire team through how to do it step-by-step.
The core leadership lesson here is simple: authority doesn't exempt you from execution—it amplifies the need for proximity. True executive leadership isn't maintained through reports and dashboards; it's built by staying close to the customer, remaining accessible to the front line, and visibly modeling the behavior you expect from your team.
Photo courtesy of Walpole Partnership

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