# The Mountain Climber Retro

Participants map upcoming milestones across a planned period, pair them with anticipated obstacles, and specify preparatory actions needed to handle them. The session yields a structured roadmap linking concrete preparation tasks directly to project milestones.

**Time:** 45 minutes. UWT facilitation plan. The source provides the three prompt categories; 45 minutes gives adequate time for silent writing, subgroup prioritization, and action commitments.
**People:** 4 to 24. Individual reflection, small groups of 3 to 4 for section review, and whole-room consolidation

## Choose this exercise

**Purpose:** Map upcoming milestones, anticipate route obstacles, and agree on preparatory actions with named owners.
**Use it when:** At the start of a year, quarter, or major release cycle when a team needs forward-looking alignment on upcoming challenges.
**Skip it when:** When a team needs an urgent post-mortem to diagnose a recent failure or outage before planning forward.

## Materials and tools

- Three distinct colors of sticky notes (one pack of each color per subgroup of 4, or three colors per person)
- Fine-tip markers (one per participant)
- Wall space, whiteboard, or digital board divided into three columns: Milestones, Obstacles, Preparation
- Laptops or internet-connected devices (for hybrid or remote sessions)
- Digital timer

## Before participants arrive

1. Draw three vertical columns on a whiteboard or set up three columns on a shared digital board labeled: Milestones, Obstacles, Preparation.
2. Distribute sticky notes and markers to tables, or confirm all participants have edit access to the digital board.

## Say this to open

Today we look ahead across our coming cycle using the Mountain Climber framework. We will map three things: key milestones on our route, obstacles we might hit before each checkpoint, and gear or preparation we must complete now. Let us begin by recording our target milestones.

## How to run it

### 1. Frame cycle and write milestones (8 minutes)

Announce the target time horizon, such as the next quarter. Participants take 4 minutes to silently write major deliverables or checkpoints on their first color of sticky notes, one item per note. For example: 'Staging environment live by March 15'. Participants place notes in the Milestones column. The facilitator reads aloud and merges direct duplicates.

### 2. Identify obstacles along the route (9 minutes)

Direct participants to review posted milestones. Give 4 minutes of silent writing on a second color of sticky notes for obstacles: specific risks, dependencies, or skill shortages. Participants post notes in the Obstacles column beside the exact milestone they affect. A prompt example: 'Security sign-off delayed by third-party audit'.

### 3. Specify preparation and equipment (10 minutes)

Prompt the room: What preparations or tools must we pack to handle these obstacles? Participants spend 5 minutes writing tangible preparations, tools, or training steps on a third color of sticky notes. They post them in the Preparation column next to the corresponding obstacles. An example: 'Schedule audit pre-review in week two'.

### 4. Review sections and assign action owners (13 minutes)

Divide participants into subgroups of 3 to 4. Assign each subgroup a cluster of milestones. Each subgroup reviews the linked obstacles and preparations, selects their single most critical preparation action, and drafts a concrete owner and completion date. Subgroups share their single action with the whole room to verify feasibility and resolve cross-team dependencies.

### 5. Debrief and record commitments (5 minutes)

Confirm where final action items and the board photo or digital export will live. Lead a rapid whole-group debrief using the stated questions, taking brief responses from two or three volunteers to conclude on time.


## Debrief questions

- Which identified obstacle presents the highest risk if left unprepared?
- What is one preparation task that gives our team the greatest immediate safety margin?
- At what regular checkpoint will we review these preparations against our actual route?

**Finished output:** A board aligning milestones, expected obstacles, and a prioritized list of preparation actions with assigned owners and dates.

## Remote

Run on a digital whiteboard with three labeled columns: Milestones, Obstacles, Preparation. Use color-coded digital sticky notes. Keep video or audio connected. Run silent writing directly on the board. For step 4, split into digital breakout rooms of 3 to 4 participants to review assigned milestone clusters before sharing their primary action in the main room.

## Hybrid

In-person and remote participants join the same digital whiteboard from individual laptops. In-person members type their sticky notes online so remote members see updates simultaneously. Audio is shared through a centralized room microphone and speaker setup. Breakout subgroups can mix remote and in-person attendees via individual headsets.

## Access and participation choices

- Participants may submit thoughts silently via notes without speaking aloud.
- Any participant may pass during verbal sharing or choose to contribute solely to the Preparation column.

## If the session gets stuck

**Participants post broad, abstract obstacles like 'lack of alignment' or 'bad communication'.**

Ask the writer to connect the note to one specific milestone and name the exact handoff or tool that breaks down.

**The Preparation column fills with massive, multi-month deliverables instead of readiness tasks.**

Remind the room of the packing metaphor: focus on checks, tools, or decisions that can be completed within the next two weeks to be ready.


## Terms used here

- Milestone: A key delivery target, deadline, or intermediate checkpoint on a project schedule.

## Sources and adaptation

Observed in EasyRetro template library, attributed there to Echo Meter App.

Retained the three core prompts (Milestones, Obstacles, Preparation) from the Mountain Climber Retro template observed on EasyRetro. UWT added the 45-minute timed sequence, subgroup scoping to keep large groups on schedule, hybrid laptop requirements, neutral concrete examples, and debrief prompts.

[EasyRetro](https://easyretro.io/templates/the-mountain-climber-retro/)

Current run sheet: https://unitedwetransform.com/exercises/the-mountain-climber-retro/