How first-time LMS implementations actually succeed

This playbook describes how first-time LMS implementation is run at JollyDeck.

It is written for HR ops teams in organisations of 50–250 employees, where SSO is already in place and learning must operate as a system, not a side project.

The focus is execution. Ownership is explicit, sequencing is enforced, and failure modes are addressed directly. This is not a buying guide, a feature overview, or a culture manifesto. It is an operational reference designed to be followed.

Executive summary

This playbook documents the operational model used to implement an LMS for the first time at JollyDeck.
It is designed for organisations of 50–250 employees where:

• SSO is already in place and mandatory
• HR operations owns people data and process cadence
• managers control time, prioritisation, and enforcement
• compliance training exists and cannot fail

The core premise

First-time LMS implementations do not fail because of technology.
They fail because ownership, identity, and manager accountability are weak or implicit.

This playbook solves for that by:

• assigning single-point ownership to HR ops
• treating SSO and identity as foundational, not optional
• using compliance training as the early anchor to force real behaviour
• engineering managers into the process via reporting and escalation
• defining hard stop conditions that prevent silent failure

What success looks like

Within 90 days:

• all users authenticate via SSO
• mandatory learning completion is predictable and visible
• managers act on overdue learning without manual chasing
• HR ops workload decreases rather than increases
• learning becomes an operational system, not a project

This is not a culture manifesto.
It is an execution manual.

An internal playbook for HR ops teams (the JollyDeck way)

This guide is written for organisations implementing an LMS for the first time.
It assumes:

• 50–250 employees
• an existing identity provider (Microsoft Entra ID / Google Workspace)
• SSO is mandatory
• HR operations owns people data and operational cadence

This is not a buying guide.
This is not a feature overview.

This is a practical implementation playbook designed to prevent the most common LMS failure modes.

Who this guide is for (and who it’s not)

This guide is for:

• HR ops teams responsible for onboarding, compliance, and people data
• L&D teams working inside HR ops constraints
• internal implementation leads coordinating HR, IT, and managers

This guide is not for:

• organisations experimenting with “learning culture” without operational backing
• teams without a clear HR ops owner
• implementations where managers are not expected to act

If those exclusions feel uncomfortable, pause the implementation. The LMS will not save you.

The uncomfortable truth about first-time LMS implementations

Most first-time LMS projects do not fail technically.
They fail operationally.

The most common failure modes are:

1. The LMS launches without real ownership
   HR, IT, and L&D all “support” it. No one runs it.
2. Managers are informed, but not operationally bound
   They agree it’s important, then do nothing when deadlines collide.
3. Identity and user data are treated as a setup step
   Instead of as the backbone of automation, reporting, and trust.
4. Content perfection blocks launch
   Teams wait for a “complete catalogue” and ship nothing.
5. Adoption is measured too late
   By the time learning performance data is reviewed, behaviour is already set.

This playbook exists to design these failures out.

The implementation model

The JollyDeck implementation model is phase-based, with hard gates.

Each phase has:

• a single operational owner
• a concrete output
• a go / no-go decision

You do not “move on” because the calendar says so.
You move on because the system is ready.

The phases

1. Charter and ownership
2. Identity, SSO, and user model
3. Minimum viable learning catalogue
4. Manager-led pilot
5. Launch and adoption operations
   

Each phase links directly to the JollyDeck LMS implementation checklist, written as executable tasks.

Why SSO matters (and why JollyDeck treats it as foundational)

In organisations of this size, SSO is not about convenience.
It is about legitimacy and adoption.

When SSO is enforced:

• users appear automatically and correctly
• organisational structure is inherited, not re-created
• managers see their teams without manual mapping
• learning assignment and reporting become reliable
• the LMS feels like part of the company, not a tool

When SSO is absent or optional:

• users trust the system far less
• login issues consume HR ops time
• managers disengage
• reporting becomes suspect
• automation breaks

At JollyDeck, SSO is treated as a first-order requirement, not an add-on:

• one identity source
• no parallel user databases
• no manual reconciliation loops

If SSO is not ready, the implementation should not proceed.

Ownership model (non-negotiable)

• HR ops owns the LMS
• IT supports identity and security
• managers own completion
• L&D supports content quality

This is not a shared responsibility model.
Shared responsibility is how LMSes quietly die.

HR ops is the only function positioned to:

• maintain people data integrity
• run recurring operational cycles
• enforce deadlines
• escalate when required

Managers are not “engaged”.
They are instrumented.

JollyDeck LMS implementation checklist

This checklist describes how LMS implementation is run at JollyDeck under normal operating conditions.

In practice, not all constraints can always be satisfied at once. HR ops teams often operate within structural, political, and technical limits they do not fully control.

The purpose of this checklist is not to ignore those realities, but to make trade-offs explicit. Where a task cannot be completed as written, that constraint should be recognised, recorded, and consciously accepted. Silent compromises are what cause LMS implementations to fail.

If a step is skipped, it should be skipped deliberately — with a clear understanding of the risk introduced and the work deferred.

First-time rollout (HR ops–led)

This checklist defines how LMS implementation is done at JollyDeck.
Tasks are written to be executed, not interpreted.

Phase 0: Charter and ownership

Owner: HR ops
Timing: before any system setup

Top priority

• define LMS scope (who is included now; who is explicitly excluded)
• confirm compliance training as the initial anchor use case
• confirm SSO as mandatory (no local credentials)
• assign HR ops as LMS system owner
• assign escalation authority to HR ops

Then consider

• document manager accountability for learning completion, not promotion of the LMS
• secure executive sponsor backing for enforcement

Do not proceed if:

• ownership is shared or unclear
• compliance is deferred
• managers are exempt from accountability

Phase 1: Identity, SSO, and user model

Owner: HR ops (with IT support)
Timing: before any content work

Top priority

• designate the identity provider as the single source of truth
• enable SSO in JollyDeck
• disable password-based login
• import users automatically via SSO
• define user roles (learner, manager, admin)
• validate manager-to-direct-report visibility

Then consider

• map departments and teams from the identity provider
• validate learner visibility of assigned learning
• test joiner flow (new user appears automatically)
• test mover flow (department or role change is reflected)
• test leaver flow (access is revoked correctly)

Do not proceed if:

• users require manual creation or correction
• SSO can be bypassed
• managers cannot reliably see their teams
• joiners or leavers require manual intervention
• identity data is being fixed inside the LMS

Phase 2: Minimum viable learning catalogue (compliance-led)

Owner: HR ops + L&D
Timing: after identity is stable

Top priority

• define the mandatory compliance learning set
• define which roles require which compliance training
• create or import compliance courses into JollyDeck
• define completion deadlines for mandatory learning
• assign compliance learning by default
• validate completion tracking
• validate overdue status visibility

Then consider

• create a short “how learning works here” course
• assign onboarding learning paths (if applicable)
• validate learner access to assigned learning
• validate reporting accuracy for HR ops

Do not proceed if:

• mandatory learning is missing
• compliance roles are undefined
• completion cannot be reliably tracked
• overdue learners are not immediately visible
• HR ops cannot extract accurate reports without manual work

Phase 3: Manager-led pilot

Owner: HR ops
Timing: before organisation-wide launch

Top priority

• select pilot group that includes real managers
• assign real compliance learning to pilot group
• require managers to view team progress
• require managers to act on at least one overdue learner

Then consider

• collect friction points (login, reporting, clarity, timing)
• resolve blocking issues
• retest reporting after fixes

Do not proceed if:

• managers ignore reports
• HR ops cannot trigger action
• completion stalls without manual chasing

Phase 4: Launch and activation

Owner: HR ops
Timing: once pilot passes

Top priority

• send manager briefing (expectations and mechanics)
• assign organisation-wide mandatory learning
• activate automated reminders in JollyDeck
• monitor adoption daily for first 7 days

Then consider

• send learner launch communication
• resolve issues immediately
• confirm reporting stability

Do not proceed if:

• reminders are disabled
• managers lack clarity on expectations
• HR ops cannot intervene decisively

Phase 5: Adoption operations (30-60-90 days)

Owner: HR ops
Timing: post-launch

Top priority

• establish weekly HR ops review cadence
• send weekly manager progress digests
• escalate overdue mandatory learning

Then consider

• review content usage
• retire unused or ineffective content
• adjust learning paths
• review reporting accuracy
• document operational improvements

Do not proceed if:

• compliance completion is unpredictable
• manager intervention does not occur
• HR ops workload increases over time

Explicit stop conditions (pause immediately if…)

• HR ops loses control over user data
• SSO is bypassed
• managers are not held accountable
• compliance reporting becomes unclear
• manual work increases after launch
  

Stopping early preserves trust.

What this checklist intentionally avoids

• feature comparisons
• motivational theory
• culture narratives

Those do not prevent failure.
Operational clarity does.

Last update: January 2026