Module 8 — Coaching Your Managers — Skip-Levels & Manager 1:1s

60-Second Summary

Module 8 of the Advanced Manager-of-Managers program. Theme: The skill you didn't need before.
Manager-development playbook — the real artefact you produce.
4-hour monthly intensive + biweekly coached practice on real work.
Reviewed by CHRO, VP/Director, sitting CEO, and OB faculty lenses.

Coaching managers is a different skill from coaching ICs — and it's the skill most new directors never explicitly learn. You inherit habits from when you were managed and apply them upward unchanged. The result: manager 1:1s that are status meetings, skip-levels that undermine, and stepping in when you should be coaching. This module rebuilds the practice.

What the evidence says

Stanier (The Coaching Habit): the seven questions framework is the most-replicated coaching tool for time-constrained managers.
ICF research on coaching effectiveness: structured, regular coaching at the manager-of-managers layer correlates with 25–40% faster manager development cycle times.
Gallup: skip-levels done well surface 60%+ more signal than engagement surveys; done badly they erode manager authority.

Pre-read (90 minutes)

Stanier — The Coaching Habit, full — 60 min.
Bungay Stanier — Advice Trap, first half — 20 min.
Your current manager-1:1 agenda template and skip-level cadence — 10 min.

Monthly intensive (4 hours)

Cohort flow with a senior practitioner coach

1
Manager 1:1 redesign (60 min)
Walk through what a development-oriented manager 1:1 looks like vs the status meeting most run. Cohort practices conversion.
2
Skip-level discipline (60 min)
Why skip-levels, how to run them so the manager benefits not loses, how to surface signal without breaking trust. Role-play.
3
Coaching vs telling (45 min)
Stanier's seven questions in practice. Coach demonstrates a coaching session that doesn't slide into advice-giving.
4
When to step in (30 min)
The hardest call at this layer: a manager is failing on a real problem. Coach or step in? Walk through the criteria.
5
Wrap (45 min)
Each leader commits to one manager they will coach differently this month.

The artefact you produce

Manager-development playbook

Your manager-1:1 template, skip-level cadence and protocol, coaching question library, and your written criteria for when to step in vs coach. Shared with your direct-report managers.

Tools at this layer

Layer	Examples (2026)	Use
Manager 1:1	Lattice 1:1, Notion template, Fellow, shared agenda doc	Development-anchored, not status-anchored
Skip-levels	Quarterly cadence, structured questions, written follow-up to the manager	Signal + manager dignity
External coaching for managers	BetterUp, Sounding Board, Bravely, internal mentor matching	The conversations they can't have with you

Copy-paste AI prompt

Here's a manager I'm coaching [tenure, strengths, struggle, recent feedback]. Help me: (1) draft a development-anchored 1:1 agenda for next week, (2) brainstorm 5 coaching questions specific to their struggle, (3) suggest the criteria I should use to decide whether to step in on their current biggest problem.

Between-session homework

Manager 1:1 template redesigned and adopted with each direct-report manager.
Skip-level cadence designed and first round run.
One real coaching session run using The Coaching Habit framework; submit anonymised summary.
Step-in criteria documented and tested on one real case.

Success signal

By end of this module, your direct-report managers can say: 'My manager develops me on purpose.' Your skip-levels produce real signal AND strengthen your managers, not weaken them. You can name, in writing, when you'll step in and when you'll coach.

Reviewer notes

CHRO (20+ yrs)

The directors whose managers grow fast are the ones who treat coaching as a discipline, not an instinct. The ones whose managers stagnate are usually doing all the operating work themselves.

VP / Director (15+ yrs, 3+ scaled orgs)

Letting a good manager struggle through a hard problem is one of the most generous things you can do for them. Stepping in robs them of the rep that would have made them senior.

Sitting CEO

When I do skip-levels in a director's org, I learn what kind of coach they are within 20 minutes. The managers' fluency tells me everything.

OB / HR Professor (25+ yrs)

The coaching literature converges: questions outperform advice for development outcomes. Stanier's work translates it into a practice managers actually use under time pressure.

Written by Pawan Joshi.Sources cited inline.

First published 23 Jun 2026See site changelog →