How to coach and manage your most difficult managers

Executive overview

Some managers damage teams through poor interpersonal skills, rule-breaking, or inability to handle conflict — yet termination is rarely the right first move. A structured six-step coaching process can turn a problem manager around before the situation escalates.

Ignoring a difficult manager doesn't fix them; a deliberate coaching plan does.

Signs you have a difficult manager

• Direct reports file more complaints than from other teams
• Higher turnover or transfer requests from one team
• Team productivity lags compared to peers
• Manager gets angry easily, raises their voice, or retaliates
• Manager ignores established procedures or is stuck in old ways
• Nosy or over-involved in employees' personal matters

The six-step battle plan

1. Review complaints and observe patterns — check one-on-one notes, project completion rates, and whether the manager deflects blame onto others
2. Offer management training to all managers — broad rollout prevents the problem manager from feeling singled out
3. Evaluate their management style — use 360-degree feedback surveys; assess communication skills and how they handle criticism
4. Run mock scenarios — role-play interviews, feedback conversations, high-stress situations, and team meetings; invite other managers so the problem child can see different styles in action
5. Have a direct one-on-one conversation — works best when the manager is likely to respond well; may be a first step or last resort depending on personality
6. Escalate to their manager — if issues persist, involve senior leadership; keep them updated throughout so escalation is not a surprise

Recommended training resources

• The Art of Caring Leadership — Heather R. Younger
• Inclusion on Purpose — Ruchika Tulshyan
• Let's Grow Leaders (Karen Hurt and David Dye) — leadership workshops

Benchmarking continuous improvement

• Hold skip-level meetings with the manager's team to gauge progress
• Ask whether employees who complained previously feel improvement
• Check in with the manager directly on how they feel about their own development
• Assign regular training modules to all managers, not just the difficult one
• Use an HRIS to assign training and require completion acknowledgement