Leading When Values Clash, Supporting Someone Through Personal Hardship, and Rebuilding Confidence After Failure [Office Hours #024]

Your questions. Answered.

👋 Welcome to a 🔒 subscriber-only edition 🔒 of our Office Hours newsletter with our founder, Ian Hallett. Every Tuesday, Ian tackles reader questions covering the most demanding challenges of management and leadership.

See all Office Hours editions here.

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In this week's edition, Ian answers:

1. How do you lead a team member whose values seem misaligned with the rest of the group or company culture?

2. How do you support a team member who’s going through a personal crisis without overstepping?

3. How do you help someone rebuild confidence after they’ve failed publicly or made a high-stakes mistake?

Let’s get started…

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Question 1:

Noah from Vancouver
How do you lead a team member whose values seem misaligned with the rest of the group or company culture?

Response:
Dear Noah,

This is one of those situations where leadership becomes as much about alignment as it is about performance. When someone’s values or behaviors feel out of sync with the culture, your job is to explore whether the gap is a misunderstanding, a mismatch, or an opportunity to evolve—on either side.

1. Separate Values from Behavior

Sometimes what looks like a values clash is actually a behavior issue. For instance, if someone values directness and the team values harmony, they may come across as abrasive—not because they’re misaligned, but because there’s no shared language for navigating that tension.

Start by getting curious:
"I’ve noticed some friction between your approach and the team’s norms. Can we unpack what matters most to you in how you work and communicate?"

You’re not accusing—you’re opening a door.