The Shay Show #45 - How to Manage Underperforming EmployeesThe Shay Show #45 - How to Manage Underperforming Employees
Journey To Freedom
Shay Doran shares four key lessons from 12 years of leading teams on how to handle underperforming employees with honesty and clarity. The episode focuses on practical ways to set expectations, listen properly and let people own their performance changes.
22:36•4 Aug 2021
Honest Conversations: Handling Underperformance Without Losing Your Humanity
Episode Overview
- Make sure expectations are crystal clear before labelling something as underperformance.
- Use regular one-to-ones so performance issues are never a surprise to the employee.
- Listen carefully to the person’s perspective; there may be hidden personal or work-related factors.
- Have open, honest conversations about whether the role truly suits their skills and motivation.
- Let the employee design their own plan to improve, then ask what support they need from you.
“It's about having an honest, human-to-human, open conversation.”
How do people find strength in their journey to sobriety? Sometimes it's by learning to have braver conversations at work too. This episode of Journey To Freedom shifts the focus from personal habits to leadership habits, zeroing in on a challenge many managers dread: dealing with underperforming employees. Host Shay Doran shares 12 years of real-life experience, starting from his first team at 19, through banking, sales, and regional leadership roles.
He talks openly about the awkwardness of these conversations, admitting that in his early days he sometimes hid behind corporate training language and came across as detached. You’ll hear him reflect on moments where he “took it too far”, and how those mistakes pushed him to handle performance issues in a more human way. Shay breaks underperformance down into everyday situations: lateness, missed targets, low morale, resistance to change, even serious issues like theft.
From there, he offers four simple, repeatable principles. First, there should be no surprises; underperformance needs to be highlighted early in regular one-to-ones. Second, “listen intently” and remember there might be unseen struggles behind the behaviour. Third, have honest, direct conversations, asking questions like, “Are you really enjoying this?
Is this really the role that you want to be doing?” And finally, let people own their performance and their plan to change, instead of the manager taking on all the responsibility.
Throughout, Shay keeps the tone practical and relaxed, reminding entrepreneurs and leaders that these chats “do not need to be scary” and that “it’s about having an honest, human-to-human, open conversation.” For anyone trying to build a healthier life and a healthier team at the same time, his approach offers a straightforward way to deal with underperformance without losing your compassion or your sanity.
Ready to face that difficult conversation you’ve been putting off, and maybe free up some energy for your wider recovery journey too?
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