The Curious Leadership - Coaching Engagement Toolkit
cThe Curious Leadership · Coaching Engagement Toolkit
Sample toolkit
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Client-facing · Visible process
How a Six-Month Engagement Works
What happens, when, and who's involved across a six-month engagement.
1
0Pre-start

Chemistry

A candid 45-minute conversation to test fit both ways. No obligation. If it's not right, we say so.

45 minCoachee + coachNo fee
1Weeks 1-3

Foundations

Three-way contracting with the sponsor or manager and coach. Goals are signed off. Launch leadership 360 and/or stakeholder interviews if desired.

Three-way contractingGoal agreementLeadership 360 and/or stakeholder interviews
2Months 1-6

Core coaching

Fortnightly 60-90 minute sessions. Every session is confidential for the coachee. If concerns arise about the engagement itself - momentum, attendance, fit - those are raised with the sponsor early. Session content stays confidential.

~12-14 sessionsFortnightly, including leadership 360 debriefCoach support between if needed
3Month 3

Midpoint sponsor review

A structured check-in on momentum - aggregate themes only, never session content. Recalibrate goals if needed. Leadership 360 high-level development plan or key stakeholder check-in.

Sponsor or manager + coachee + coachAggregate themes only
4Month 6

Close-out & sustainability

Close-out meeting, close-out report, recommendations for the organisation and leader development plan.

Close-out and recommendations360 re-testing or stakeholder check-point if desiredLeader development plan

Rules of engagement

  1. What's said in coaching stays in coaching. Sponsors see progress and themes; they never see session content. This is to ensure trust and transparency is in place for all.
  2. Everything shared with the organisation is agreed with the leader first. Reports, 360 summaries, development plans - the leader sees them before anyone else does.
  3. Goals are contracted three ways at the start. If change is required, we can recalibrate.
  4. Honesty both ways. If coaching isn't the right intervention, or momentum stalls, it gets named early.
The Curious Leadership · Coaching engagement toolkitSample
Client-facing · Foundations phase
Intake meeting
The one-on-one conversation with the coachee, to understand where they're starting from.
2

The intake meeting is where the coach meets the coachee one-on-one to understand where they're coming into coaching. This is an illustrative outline of what it covers.

What we cover

  • 1Introductions and background. How the engagement came about, and space for the coachee to introduce themselves, their role, and what's going on for them right now.
  • 2Current context (20-30 minutes). The coachee's context, challenges and goals - what they're struggling with, what they hope to change through coaching, and any expectations they're bringing.
  • 3How we will work together, and agreeing the way forward. The coach explains how they coach, the coach and coachee discuss expectations, and together they agree on fit and how to go forward.
The Curious Leadership · Intake meetingSample
Coachee-facing · Foundations phase
Coachee Intake Form
A short form for the coachee to complete before coaching begins.
3

Take your time with these. There are no right answers - the more honest you are, the more useful the coaching will be.

We all have underlying fears or beliefs that hold us back from being our best, and recognising them is one of the most important parts of coaching. Note a few things that might be holding you back - for example: "I lack confidence", "I feel like an impostor", "I second-guess myself all the time". For each one, mark how much it affects you right now.

Something holding me back · 1

On a scale of 1 to 10, how much does this impact your mindset, how you show up, and what you can achieve right now?

1 · barely10 · a great deal
Something holding me back · 2

On a scale of 1 to 10, how much does this impact your mindset, how you show up, and what you can achieve right now?

1 · barely10 · a great deal
Something holding me back · 3

On a scale of 1 to 10, how much does this impact your mindset, how you show up, and what you can achieve right now?

1 · barely10 · a great deal
Something holding me back · 4

On a scale of 1 to 10, how much does this impact your mindset, how you show up, and what you can achieve right now?

1 · barely10 · a great deal
The Curious Leadership · Coachee intake formConfidential
Client-facing · Foundations phase
Three-way engagement meeting
Coach, coachee and manager, aligning on the engagement before coaching begins.
4

The coach, the coachee and the coachee's manager meet together to agree what the engagement is for. Holding it as a three-way conversation means everyone commits to the same goals in the open. This is an illustrative outline of what it covers.

What we cover

  • 1The goals of the engagement. What the coaching is for, and what success looks like for the coachee, the manager and the business.
  • 2The measurement outcomes. What we'll track, and what will tell us the work is landing.
  • 3What needs to shift, and what will be different. The specific changes everyone wants to see, named openly while all three are at the table.
  • 4Agreeing goals and expectations. Through the conversation we land on what the goals look like, along with any other expectations, so everyone starts aligned.

After this, the coach meets the coachee one-on-one for the intake conversation.

The Curious Leadership · Three-way engagement meetingSample
Client-facing · Foundations phase
Goal setting
The areas every leader sets clear, defined goals against.
5

Setting clear, measurable goals so that your leaders have accountability to clear outcomes.

Examples of measures that goals are set against:

Delivery and execution

The business outcomes this leader is accountable to. Supporting the leader to define how they'll achieve clear, outcome-driven goals and work with other stakeholders and areas of the business.

Leading a team

The team this leader is accountable to build. How this leader builds the team around them. Goals will be set against factors like engagement, retention of high performers, span of control and depth, delegation, and handing over decision rights.

Leadership

How they lead, and how they're experienced. We'll determine the gap through a 360 leadership survey, manager feedback and stakeholder feedback in the business.

Personal development and well-being

What does this leader need to lead with more clarity and confidence? These goals are set in private with the coachee, based on what they need to work on personally to help them achieve their goals.

Personal indicators to shift

Alongside these goals, each coachee names a few personal indicators they want to shift and self-scores where they're starting, on a simple 1-6 scale. The real indicators a coachee chooses aren't shared outside coaching. The example below is illustrative, based on a real client, and shows the intake point only.

Confidence
Intake
2
Stress
Intake
2
Exhaustion
Intake
1
Imposter syndrome
Intake
2
Scale: 1 (weighing on me) - 6 (thriving) · self-scored at intake
The Curious Leadership · Goal settingSample
Interview guide · Foundations phase
Stakeholder Interview Guide
Short, confidential conversations with the people who work closely with the leader.
6

The questions

  • 1At their best, what does Alex bring as a leader?
  • 2What could Alex be doing more of?
  • 3What could Alex be doing less of?
  • 4In six months' time, what is the observable shift Alex could make that would demonstrate these changes?

Synthesis note

Cluster the responses into 3-4 themes. Share the themes with the leader, never attributed comments. Lead with strengths, then the shifts that would make the biggest difference. If only one person raised something, hold it lightly.

The Curious Leadership · Stakeholder interview guideConfidential · Not attributed
Sponsor deliverable · Midpoint / quarterly
Midpoint / Quarterly Engagement Report
Enough visibility for the sponsor to feel confident, without ever breaching the coachee's confidence.
7
Coachee
Alex Rivera - VP Engineering
Manager
Mary Cuthers - Chief Technology Officer
Sponsor
Kelly Adams - Chief People Officer
Engagement
6-month · per-engagement
Reporting period
Q1 · Jan-Mar 2026

Engagement health

Sessions delivered9 sessions over 24 weeks (target of 12)

Goals on track

Goal 1On track
Goal 2On track
Goal 3Early progress

Note: Leadership 360 completed. Alex will lead the walk-through of the report and initial development plan.

Focus areas this quarter (agreed with coachee)

Delegation & scale

Moving from being the technical decision-maker to building a team that decides well without them.

Executive presence

Leading peers and the exec team with the same authority they lead their own function.

Observable shifts

Colleagues in the midpoint check-in noted Alex is delegating more visibly and stepping back from detail. Early, but directionally clear. Deeper work on peer-level influence is underway and will show over the next quarter.

Where the organisation can help

The biggest enabler right now is org-side: giving Alex genuine air-cover to let their team make (and occasionally fumble) calls. Growth here is as much a system change as a personal one.

Personal indicators (coachee-owned)

The coachee is tracking a set of personal indicators on a 1-6 scale. The movement is shown below. The indicators themselves stay in coaching, and the coachee decides what, if anything, is shared here.

IntakeNow
Personal indicator 1
Intake
2
Now
4
Personal indicator 2
Intake
2
Now
3
Personal indicator 3
Intake
1
Now
3
Personal indicator 4
Intake
2
Now
4
Scale: 1 (weighing on me) - 6 (thriving)
The Curious Leadership · Midpoint / quarterly reportPrepared 31 Mar 2026
Deliverable · End of engagement
Close-Out Report
Where the engagement landed, and the plan to carry it forward.
8

The last 6 months in a paragraph

Alex came in leading brilliantly at the level below the one the company now needs. Over six months the centre of gravity shifted from being the best engineer in the room to building a room that doesn't need them to be. The work isn't finished but the direction is now self-sustaining.

Where things moved

Delegation & scaleStrong movement
Executive presenceMeaningful movement
Owned vs. borrowed authorityEarly but progressing

Strengths to keep leaning on

Rare technical credibility, genuine care for their people, and a willingness to be coached - which is itself a leadership strength.

Areas to continue working on

Peer-level influence under pressure, and resisting the pull back into detail when a quarter gets hard. Both are habit under pressure, not capability. Alex shows a high level of self-awareness and has increased his ability to see where these behaviours are holding him back. (Refer to attached development plan for further details.)

Go forward plan

  • A monthly self-review against the two goals, blocked in the calendar.
  • A peer or mentor to pressure-test the hard calls - the coach's role, redistributed. Alex to determine with Kelly.
  • One standing delegation: a decision Alex commits to never taking back.

Personal indicators (coachee-owned)

Movement across the personal indicators the coachee chose to work on, start to finish. The indicators themselves stay in coaching; the coachee decides what is shared here.

IntakeEnd
Personal indicator 1
Intake
2
End
5
Personal indicator 2
Intake
2
End
5
Personal indicator 3
Intake
1
End
4
Personal indicator 4
Intake
2
End
5
Scale: 1 (weighing on me) - 6 (thriving)
The Curious Leadership · Close-out reportSample
Coachee-facing · End of engagement
Coachee Report
The coachee's own record of where they started, where they finished, and what is next.
9

Your personal indicators, start to finish

IntakeEnd of engagement
Confidence
Intake
2
End
5
Stress
Intake
2
End
5
Exhaustion
Intake
1
End
4
Imposter syndrome
Intake
2
End
5
Scale: 1 (weighing on me) - 6 (thriving) · self-scored

During intake, the coach and coachee talk through what's going on and what feels like it's holding them back. The coach's job isn't to question how they're feeling or how they define it - imposter syndrome, for example, is a label, not a description of what they're actually experiencing or what it is stopping them doing. The coach explores what it means to them, where they get stuck, and how it affects them, then looks again at the end for movement.

The Curious Leadership · Coachee reportConfidential to the coachee
Proposal · Model one
Individual Coaching Engagement
One leader, one defined outcome, over six months. The classic executive coaching engagement.
10

For a company investing in a specific senior leader - a new exec, a high-potential VP, someone stepping up a level. Fixed scope, fixed fee, clear boundaries.

What's included

  • Chemistry conversation
  • Three-way contracting with the sponsor optional
  • Leadership 360 or psychometric, and/or confidential stakeholder interviews optional
  • One-on-one coaching, targeted at fortnightly sessions across the engagement
  • Coach available between sessions when needed
  • Midpoint sponsor review and close-out report
  • Leader development plan

Investment

$9,200fixed fee · full 6-month engagement

Invoiced 50% on commencement, 50% at midpoint. Excludes travel where in-person is requested.

The essentials

Confidentiality: session content stays with the coachee; the sponsor receives progress and themes only. Cancellation: 24 hours' notice to reschedule without charge, and up to 2 sessions can be rescheduled last minute without charge - life happens. Beyond that, sessions are charged, to keep the engagement honest and respect everyone's time. Term: six months. Any unused sessions finish at the end of the engagement.

Larger engagements

Where there are more leaders to coach, the work runs as an embedded model on a negotiated retainer. One coach working across the team builds context a single engagement can't, and the approach and reporting stay consistent. Scope, reporting and pricing are shaped to the engagement - every one is different.

The Curious Leadership · ProposalValid 30 days
Proposal · Model two
Embedded Coach - Retainer
Ongoing coaching capacity across a leadership team, scoped to the engagement.
11

For scale-ups that want senior coaching available to several leaders continuously - a standing part of how the leadership team develops.

How it works

  • Two days per month, embedded and flexible
  • Coaching across up to 4 leaders, allocated as needs shift
  • Advisory access for the sponsor on team dynamics and org design
  • Quarterly aggregate read-out on leadership themes

Investment

$X,XXXper month · minimum 6-month term

Invoiced monthly in advance. Unused days don't roll beyond the following month.

The Curious Leadership · ProposalValid 30 days