Summary

Duration: 2 hours

Group Size: ~10 participants

Format: In-person, highly interactive

Workshop Objectives

By the end of this session, participants will be able to:

• Identify which collaboration habits are working and which are missing
• Understand what makes habits stick in cross-functional work
• Co-create 3-5 specific collaboration habits for their team
• Design accountability mechanisms to support new habits
• Create a practical plan for implementing and iterating on habits

Materials Needed

• Flipchart/whiteboard
• Post-it notes (multiple colours)
• Printed handouts: Collaboration Habits Assessment, Habit Design Framework, Habits Toolkit, Habit Implementation Template, Team Action Plan
• Large paper for habit mapping
• Markers
• Timer
• Name tags/table tents

Process

SEGMENT 1: Opening & Discovery (25 minutes)

Welcome & Context Setting (3 min)

• Brief welcome and workshop objectives
• Ground rules: focus on building helpful habits not criticising current practices, practical not perfect, start small
• Normalise that good intentions don’t always translate to consistent habits

Activity: “Collaboration Habit Stories” (22 min)

Purpose: Surface what’s working, what’s missing, and where habits break down

Individual Reflection (7 min):

Think about your cross-functional collaboration experiences:

On separate post-its, capture:

• One collaboration habit that works really well (what is it? why does it work?)
• One area where we have good intentions but habits don’t stick (what breaks down?)
• One thing that falls through the cracks regularly (what gets missed?)
• One collaboration frustration that keeps repeating (what keeps happening?)

Silent Posting and Clustering (6 min):

Create four flip chart areas:

• “Habits that work” (what’s going well)
• “Good intentions, poor follow-through” (where habits don’t stick)
• “Falls through the cracks” (what gets missed)
• “Repeating frustrations” (what keeps happening)

Everyone posts their sticky notes, reading others as they go

Facilitator clusters similar themes in each area

Group Discussion (9 min):

As a group, look at all four areas:

• What patterns do we see in habits that work?
• Why do some good intentions not become habits?
• What commonly falls through the cracks?
• What frustrations keep repeating?
• What would change if we had better habits?

Frame: “Today we’ll design practical collaboration habits that stick and address what’s not working.”

Facilitator Notes:

• Push for specific examples: “poor communication” becomes “we agree in meetings but then work happens in silos and people are surprised by decisions”
• Common working habits: regular brief check-ins, clear updates in shared channels, quick problem-solving sessions, celebrating small wins together
• Common habit failures: elaborate systems that are too complex, meetings that don’t lead to action, update processes that feel like bureaucracy, habits that work for some but not all
• Common things that fall through cracks: handoffs between functions, keeping everyone informed, involving right people in decisions, follow-up on actions, sharing context
• Common repeating frustrations: finding out too late, being surprised by decisions, duplicated work, waiting on others, miscommunication
• Some may be defensive about current practices: emphasise building on what works, not criticising what doesn’t
• Watch for blame patterns: redirect to “what habit would prevent this?”
• For intact teams, this reveals real pain points to address
• Listen for underlying causes: is it lack of habit, wrong habit, or systemic issue?
• Note the difference between missing habits vs. habits that exist but aren’t followed

SEGMENT 2: Understanding Effective Collaboration Habits (15 minutes)

Mini-Teach: What Makes Habits Stick in Cross-Functional Work (15 min)

The Definition:

Collaboration habit: A regular, repeated practice that team members do consistently to work together effectively.

Key distinction: Habits vs. intentions vs. one-off actions vs. complex systems.

Why Collaboration Habits Matter:

For consistency:

• Predictable ways of working
• Don’t have to reinvent each time
• Reduces cognitive load
• Creates reliability

For inclusion:

• Everyone knows how to participate
• Clear entry points for contribution
• No one left out accidentally
• Transparent processes

For effectiveness:

• Information flows smoothly
• Handoffs work reliably
• Problems surface early
• Decisions involve right people

For relationships:

• Regular touchpoints build trust
• Small interactions accumulate
• Create sense of “team-ness”
• Make collaboration feel natural

Four Types of Collaboration Habits:

1. Communication Habits

What they are: Regular ways of staying connected and informed

Examples:

• Brief daily or weekly check-ins
• Standard update formats or channels
• Regular team meetings with consistent structure
• Clear escalation paths

Purpose: Ensure everyone has information they need when they need it

2. Coordination Habits

What they are: Regular practices for managing dependencies and handoffs

Examples:

• Dependency mapping at project start
• Handoff checklists or protocols
• Regular sync on blockers
• Clear “ready for handoff” criteria

Purpose: Make cross-functional work flow smoothly

3. Decision-Making Habits

What they are: Regular processes for making and communicating decisions

Examples:

• Clear decision rights and involvement
• Standard way to propose and discuss options
• Documenting decisions and rationale
• Communicating decisions to affected parties

Purpose: Involve right people and move forward efficiently

4. Relationship Habits

What they are: Regular practices that build trust and connection

Examples:

• Celebrating wins together
• Acknowledging contributions
• Informal connection time
• Collaborative problem-solving
• Learning from mistakes together

Purpose: Create psychological safety and team cohesion

What Makes Habits Stick:

Simple and specific:

• Clear what to do
• Not complex or elaborate
• Easy to remember
• Takes minimal effort

Regular and frequent:

• Happens on schedule
• Not sporadic or occasional
• Built into rhythm of work
• Becomes automatic

Valuable for everyone:

• Everyone sees the benefit
• Not just overhead or box-ticking
• Makes work easier or better
• Worth the investment

Has clear triggers:

• Obvious when to do it
• Tied to time or event
• Everyone knows it’s happening
• Part of existing workflow

Includes accountability:

• Someone owns it
• Team reminds each other
• Track whether it happens
• Adjust if it doesn’t work

What Makes Habits Fail:

Too complex:

• Too many steps
• Requires too much setup
• Hard to remember
• Takes too much time

Irregular or unclear:

• No clear schedule
• Depends on someone remembering
• Falls to bottom of priority list
• Competes with “real work”

Benefits unclear:

• Feels like bureaucracy
• Can’t see the value
• Doesn’t solve real problem
• Just adds overhead

No accountability:

• No one owns it
• Easy to skip
• No reminder system
• No consequences if missed

One-size-fits-all:

• Imposed from outside
• Doesn’t fit team’s needs
• Not co-created
• Ignores context

The Habit Formation Process:

Stage 1: Design (today’s workshop)

• Identify what habits would help
• Make them simple and specific
• Ensure everyone understands the value
• Agree to try them

Stage 2: Launch (weeks 1-2)

• Start with 1-2 habits only
• Make them visible and easy
• Remind each other frequently
• Celebrate small successes

Stage 3: Establish (weeks 3-4)

• Habits start feeling normal
• Require less reminding
• Add 1-2 more habits if ready
• Adjust what’s not working

Stage 4: Sustain (ongoing)

• Habits are automatic
• Part of “how we work”
• Iterate and improve
• Add new habits as needed

The “Start Small, Build Up” Principle:

Better to:

• Start with 1-2 simple habits that stick
• Add more once those are working
• Build gradually over time

Than to:

• Launch 10 habits at once
• Have them all fail
• Get discouraged and give up

How Long Does It Take?

Research suggests: 18-254 days for habits to become automatic, average 66 days

For collaboration habits: Expect 4-6 weeks for simple habits to feel normal

Be patient: Building sustainable habits takes time

SEGMENT 3: Assessing Current Collaboration Habits (20 minutes)

Framework Share: Mapping Your Collaboration Landscape (3 min)

Before designing new habits, understand your current state. What habits exist? Where are gaps? What needs strengthening?

Four areas to assess:

• Communication habits: How do we stay informed?
• Coordination habits: How do we manage dependencies?
• Decision-making habits: How do we involve people and decide?
• Relationship habits: How do we build connection and trust?

Activity: “Collaboration Habits Mapping” (17 min)

Purpose: Make current habits visible and identify where to strengthen

Individual Assessment (6 min):

Using Collaboration Habits Assessment handout:

For each of the four areas (communication, coordination, decision-making, relationship):

• What habits currently exist in this area?
• How well are they working? (working well / inconsistent / missing)
• What’s one habit we need in this area?

Small Group Sharing (8 min):

Groups of 3-4:

Share your assessments

Create a collective view:

• What habits are working well across all four areas?
• Where are habits inconsistent or missing?
• What patterns do we see?
• Which area needs most attention?

Capture top 3 gaps or inconsistencies on flip chart

Whole Group Gallery (3 min):

Each group posts their top 3 gaps

Everyone does quick gallery walk

Notice patterns across groups:

• Which gaps are common?
• Which areas need most work?
• What surprises us?

Facilitator Notes:

• Help people distinguish between “we do this sometimes” and “we have a habit of doing this”
• Common working habits: quick daily standups, shared project channels, regular retrospectives, celebrating milestones
• Common gaps: proactive updates, involving right people early, clear handoff processes, acknowledging contributions, follow-up on decisions
• Common inconsistencies: habits exist but not everyone follows them, habits work in some situations but not others, habits depend on one person remembering
• Watch for: habits that worked before but don’t anymore (team changed, context changed)
• Some may think they have habits when they don’t: test with “does this happen every time without someone having to remember?”
• Listen for: which habits matter most to which functions (different needs)
• For intact teams, this creates shared understanding of current state
• Note where habits are missing vs. where existing habits aren’t working

SEGMENT 4: Designing Communication and Coordination Habits (25 minutes)

Framework Share: Designing Effective Habits (5 min)

Good habits are simple, regular, valuable, and specific. Use this formula to design habits that stick.

The Habit Design Formula:

[Frequency] + [When/Trigger] + [What] + [How Long] + [Who]

Example: “Every Monday at 9am, all functions share a 2-minute update on blockers and priorities in our team channel”

Elements of well-designed habit:

Frequency: Daily, weekly, bi-weekly, monthly (be realistic)

When/Trigger: Specific day/time or event trigger (“after project kickoff”, “when milestone completes”)

What: Specific action (not vague like “communicate better”)

How long: Time-bound (brief is better)

Who: Clear who participates or owns it

Making habits concrete:

Vague: “Better communication”

Concrete: “Every Tuesday at 3pm, 15-minute standup where each function shares: what we shipped, what we’re working on, where we’re blocked”

Vague: “Keep everyone in the loop”

Concrete: “When making a decision that affects other functions, post in #team channel with @mentions for those affected before finalizing”

Vague: “Improve handoffs”

Concrete: “Before handing work to another function, complete 3-question handoff checklist and schedule 10-minute walkthrough”

Activity: “Habit Design Workshop - Part 1” (20 min)

Purpose: Design specific communication and coordination habits

Setup (2 min):

Based on gaps identified in Segment 3, identify top priority areas:

• Communication: Where do we need better information flow?
• Coordination: Where do handoffs or dependencies break down?

Small Group Habit Design (15 min):

Divide into 2 groups:

• Group 1: Design 2-3 communication habits
• Group 2: Design 2-3 coordination habits

For each habit, use Habits Toolkit handout:

Step 1: Name the problem (3 min)

What specifically breaks down or gets missed?

Step 2: Design the habit (8 min)

Using habit design formula:

• Frequency: How often?
• When/Trigger: When does it happen?
• What: What’s the specific action?
• How long: How much time?
• Who: Who’s involved?

Step 3: Test the design (4 min)

Check:

• Is it simple enough to remember and do?
• Will it actually address the problem?
• Is the value clear to everyone?
• Can we realistically sustain this?
• Does it fit our working style?

Gallery Share and Refinement (3 min):

Groups post their designed habits

Quick review:

• Which habits feel most valuable?
• Which might be too complex?
• What’s missing?

Facilitator Notes:

• Push for specificity: “regular updates” needs to become “every Thursday at 2pm, 10-minute Slack standup”
• Help groups keep habits simple: if design has more than 3 steps, it’s too complex
• Common communication habits: brief regular standups, standard update format in shared channel, weekly email summary, quick Monday priorities sync
• Common coordination habits: dependency check at project start, handoff protocol, blocker escalation process, weekly sync on cross-functional work
• Watch for: habits that require too much time (brief is better), habits that duplicate existing meetings, habits that only work for some functions
• Test realism: will people actually do this every time? If not, simplify further
• Ensure habits have clear owners: someone needs to facilitate or remind
• For intact teams, these become their actual new habits
• Some groups may design too many habits: help prioritise the 1-2 most important
• Look for habits that create natural collaboration, not just compliance

SEGMENT 5: Designing Decision-Making and Relationship Habits (25 minutes)

Framework Share: Habits for Decisions and Connection (5 min)

Decision-making and relationship habits are often overlooked but crucial for effective collaboration.

Decision-making habits ensure:

• Right people involved at right time
• Clear how decisions get made
• Decisions communicated clearly
• Rationale is documented

Common decision-making habits:

• Decision log in shared space
• Standard involvement process (who needs to be consulted vs. informed)
• Regular decision-making meetings with clear agenda
• “Decision made” communication template

Relationship habits ensure:

• Regular connection and trust-building
• Appreciation and recognition
• Psychological safety
• Sense of shared team

Common relationship habits:

• Celebrating milestones together
• Regular recognition of contributions
• Weekly wins sharing
• Monthly retrospective or reflection
• Informal connection time
• Collaborative problem-solving sessions

These habits often feel “soft” but have hard impact on collaboration quality.

Activity: “Habit Design Workshop - Part 2” (20 min)

Purpose: Design specific decision-making and relationship habits

Setup (2 min):

Based on gaps identified, focus on:

• Decision-making: Where are people surprised or excluded?
• Relationships: Where is trust or connection lacking?

Small Group Habit Design (15 min):

Same groups as before, but swap:

• Group 1 (was communication): Design 2-3 decision-making habits
• Group 2 (was coordination): Design 2-3 relationship habits

For each habit, use same design process:

Step 1: Name the problem (3 min)

What specifically breaks down or is missing?

Step 2: Design the habit (8 min)

Using habit design formula:

• Frequency, when/trigger, what, how long, who

Step 3: Test the design (4 min)

Is it simple, valuable, sustainable?

Gallery Share and Refinement (3 min):

Groups post their designed habits

Quick review:

• Which habits feel most impactful?
• Which might need adjustment?
• What resonates?

Facilitator Notes:

• Help groups see value of relationship habits: they feel “nice to have” but are crucial for collaboration
• Common decision-making habits: post decisions in standard format, involve affected parties before finalizing, weekly decision sync, clear escalation path
• Common relationship habits: Friday wins sharing, monthly team lunch or coffee, recognizing contributions in team meeting, retrospective after major milestones, celebrating project completions
• Watch for: decision habits that are too bureaucratic (should make decisions easier not harder), relationship habits that feel forced or inauthentic
• Relationship habits work best when they feel natural: build on what team already enjoys
• Some may resist “soft” habits: help them see connection to collaboration effectiveness
• For decision habits, clarity about who decides vs. who’s consulted is crucial
• Test if habits address real frustrations from opening activity
• Ensure habits don’t require too much coordination overhead

SEGMENT 6: Selecting and Planning Implementation (20 minutes)

Framework Share: The Implementation Approach (5 min)

Don’t try to launch all designed habits at once. Start small, build up gradually.

The 1-2-3 Implementation Model:

Week 1-2: Launch 1-2 habits

• Choose simplest, highest-value habits
• Focus all attention on these
• Remind each other frequently
• Celebrate when they happen

Week 3-4: Check and adjust

• Are these habits sticking?
• Do they need tweaking?
• Add 1-2 more if ready
• Drop what’s not working

Week 5-6: Expand or sustain

• Add more habits if team is ready
• Focus on sustaining what’s working
• Keep iterating

Success looks like: Small number of habits that actually happen consistently, not large number of habits that fail

The accountability question:

Who will:

• Remind the team about the habit?
• Track whether it’s happening?
• Raise the flag if it’s not working?
• Lead habit check-ins?

Every habit needs an owner (not to do it alone, but to ensure it happens)

Activity: “Habit Selection and Planning” (15 min)

Purpose: Choose which habits to start with and plan implementation

Whole Group Habit Selection (8 min):

Review all designed habits from both activities

Using Habit Implementation Template handout:

Step 1: Vote on top priorities (3 min)

Each person gets 3 votes

Vote for habits you think are:

• Most valuable
• Most likely to stick
• Most needed right now

Tally votes

Step 2: Select starter habits (5 min)

As group, choose 1-2 habits to launch in weeks 1-2:

Consider:

• Which got most votes?
• Which are simplest?
• Which address biggest gaps?
• Which have most energy?

Agree on 1-2 to start (3 maximum)

For each selected habit:

• Confirm the specific design
• Assign an owner
• Clarify who participates
• Identify where to document it

Individual Planning (5 min):

Individually, think about:

What will help me remember these new habits?

What might get in the way?

How will I support teammates in building these habits?

What’s one thing I personally commit to?

Brief Whole Group Share (2 min):

Quick popcorn: “One thing I’ll do to support our new habits is…”

Facilitator Notes:

• Help group resist urge to launch everything at once: start small or habits won’t stick
• If group can’t choose, help prioritise: which would have most immediate impact?
• Ensure selected habits have clear owners: without ownership, habits die
• Common mistake: choosing habits that sound good but are too complex for first launch
• Watch for: habits that only work for some people (may need adjustment)
• Make habit ownership visible: write names on flip chart
• Help group be realistic about capacity: launching during busy period is harder
• Some may want to launch more habits: remind them they can add more in weeks 3-4
• For intact teams, these become their actual implementation plan
• Document selected habits clearly: will be used as reference
• Check that everyone understands exactly what the habit is and when it happens

SEGMENT 7: Integration & Commitment (10 minutes)

Tool Distribution (2 min)

Provide take-home resources:

• Collaboration Habits Assessment (already have)
• Habit Design Framework
• Habits Toolkit (already have)
• Habit Implementation Template (already have)
• Team Action Plan

Team Commitments (6 min)

For intact cross-functional teams:

Using Team Action Plan handout, capture:

Our starter habits (launching weeks 1-2):

Habit 1: _______________________________________________

Owner: _______________________________________________

Habit 2: _______________________________________________

Owner: _______________________________________________

How we’ll remind each other: _______________________________________________

When we’ll check progress: _______________________________________________

Additional habits to consider (weeks 3-4): _______________________________________________

For mixed groups:

Individual commitments:

• One habit I’ll propose to my team
• How I’ll support building new habits
• One thing I’ll do differently

Closing Round (2 min)

Go around circle, each person shares:

“One habit commitment I’m making is…”

Facilitator provides:

• Reminder that habits take time to form, be patient
• Encouragement to start small and build up
• Note that some habits won’t work and that’s OK, adjust and iterate
• Appreciation for commitment to strengthening collaboration

Secret Sauce

Energy Management

• Segment 1 should surface frustrations while creating hope for better habits
• Segment 2 provides relief: habits can be simple and achievable
• Segments 4-5 (designing) should feel creative and empowering
• If energy dips after Segment 3, take 2-minute break before Segment 4
• Keep balance between realistic (start small) and optimistic (habits make a difference)

Common Challenges

“We’ve tried this before and it didn’t work.” Explore: What made it fail? Too complex? Not valuable enough? No accountability? Use that learning to design better.

Want to launch too many habits. Help prioritise: Start with 1-2. Add more once those stick. Success builds momentum.

Habits feel like bureaucracy. Redirect: Habits should make work easier, not harder. If a habit doesn’t add value, don’t do it.

“We don’t have time for new habits.” Reframe: Habits save time by making collaboration smoother. But start simple: 5-10 minute habits only.

Can’t agree on which habits to start. Normal. Try highest-voted ones first. Can always switch if they don’t work.

Some want elaborate systems. Simplify: Complex systems fail. Simple repeated actions succeed. Keep it basic.

Habits work for some functions, not others. Acknowledge different needs. Design habits that work for everyone or allow flexibility.

“What if we don’t stick to them?” Normalize: Building habits is hard. Plan for reminders and accountability. Adjust if needed.

Timing Flexibility

• If running behind: Reduce Segments 4 and 5 to 20 min each (3 min teach, 17 min activity)
• If ahead: Extend Segment 6 for more detailed implementation planning
• Can extend Segment 7 for more specific commitments
• Segments 4-5 shouldn’t be rushed: good habit design takes thought

Key Facilitator Moves

In Segment 1:

• Surface real habits problems, not sanitised versions
• Look for patterns: what commonly breaks down?

In Segment 3:

• Help distinguish between “we sometimes do this” and “we have a habit”
• Create clarity about current state

In Segments 4-5:

• Push for specific, simple habits (if it’s complex, simplify further)
• Ensure habits have clear triggers and timing
• Test if habit actually addresses the problem
• Help groups see value in all types of habits, including relationship ones

In Segment 6:

• Prevent over-commitment: start with 1-2 habits only
• Ensure habits have clear owners
• Make accountability explicit

Throughout:

• Emphasise “start small, build up” philosophy
• Keep habits simple and concrete
• Balance optimism (habits help) with realism (habits take time)

For Different Team Types

Intact cross-functional teams: This is real implementation work. They should leave with 1-2 habits to launch immediately and clear ownership.

Project-based teams: Create habits for project duration. Make them relevant to current work.

Mixed groups: Learn habit design principles. Practice they can apply in own teams.

Follow-Up Suggestions

• For intact teams: Launch starter habits immediately (next day or next week)
• Week 2: Quick check-in - are habits happening? Need adjustment?
• Week 4: Assess progress - what’s working? What’s not? Ready to add more?
• Week 6: Review and iterate - keep what works, drop what doesn’t, add new ones
• Monthly: Habits check-in as part of regular team meeting
• Quarterly: Assess full suite of collaboration habits, refresh as needed
• When team or context changes: Revisit habits, adjust as needed

Success Indicators

You’ll know the workshop worked if:

• Participants can articulate what habits are missing or inconsistent
• Clear distinction between different types of collaboration habits
• 1-2 specific, well-designed habits selected to launch
• Each habit has clear owner and accountability plan
• Team has realistic implementation approach (start small, build up)
• Energy and commitment to trying new habits
• Understanding that habits take time and iteration
• Plans for check-ins and adjustment

Appendix: Key Concepts Summary

Habits Take Time to Form

Expect 4-6 weeks for simple habits to feel normal. Be patient and persistent.

Start Small, Build Up

Better to have 1-2 habits that stick than 10 that fail. Add more once first ones are working.

Simple Beats Complex

Elaborate systems fail. Simple, repeated actions succeed. Keep habits basic.

Habits Need Clear Triggers

“Regular communication” is vague. “Every Monday at 9am” is clear. Make triggers specific.

Accountability Is Essential

Every habit needs an owner to ensure it happens. Without accountability, habits die.

Value Must Be Clear

If team doesn’t see the benefit, habit won’t stick. Ensure everyone understands the “why”.

Iteration Is Normal

Some habits won’t work. That’s OK. Adjust, adapt, try different approaches. Learning process.

All Four Types Matter

Communication, coordination, decision-making, and relationship habits all contribute to collaboration. Don’t neglect any area.

Context Matters

Habits that work for one team may not work for another. Design for your specific needs and working style.

Habits Enable Flow

Good habits make collaboration feel natural and effortless. They reduce friction and cognitive load.