Struggling With The Human Side of Leadership

Picture this: Walking into a role as VP of Sales, greeted by a team that, while full of potential, struggles to hit targets. It’s a scene many of us have faced – a scenario that instinctively triggers an urgent emotional desire to flip the script. This situation was the reality in my last VP role,…

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Ignoring Early Warning Signs: A Sales Leadership Misstep

Early Warning Signs: Talent We often ignore signs that our team’s talent needs to be aligned. It’s easy to miss, but spotting these signs early can make a difference. Let’s dive into how we can get better at this. Talent Assessment: The Four Buckets  Sales talent can be categorized into four types: Sales leaders often…

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The Pitfall of Misaligned Goals

Untangling a Web of Priorities I think back to yet another role of mine. I came in as the VP of Sales, brought in to turn around another underperforming team. A team, I soon discovered, who were more than capable of delivering the numbers we needed. Capable, if not for the plethora of “priorities” they’d…

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A Tale of Two Methods

As a vice president, I worked with several direct reports. Each with a unique approach to their roles. It quickly became apparent that their engagement method and grasp of numbers significantly impacted their success and the perception of their leadership skills. This experience highlighted three critical areas in managing upwards and keeping your organizations informed:…

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Integrating Sales and Product Teams for a Landmark Deal

The perfect story for this week’s newsletter came from my last job and a vast deal we worked on. This deal was big and messy, and we knew we needed an edge, something to put it over the top. Faced with a complex deal that demanded a more profound understanding, we turned to an often-overlooked…

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