Coaching, Trust and the Cost of Misreading Your Rep With Sian Taylor

In this episode, Shivan is joined by Sian Taylor, Sales Manager at Klaviyo, for a candid conversation about one of the most overlooked responsibilities in leadership, understanding your reps before you coach them.

Sian shares a pivotal early management mistake: focusing on performance metrics instead of the person behind them. The result? A damaged relationship, a loss of trust, and a painful rebuild that taught her how much leadership really hinges on empathy.

They discuss coaching blind spots, misreading motivation, and how to have tough conversations without losing your team. If you’re stepping into sales management, or already navigating that tricky balance of people and performance, this episode is packed with honest lessons that can shape your approach.