THE TEMPEST TWO / PROPOSAL FOR AIRBNB
THE
EXPLORER
PROJECT
Building a leadership team that takes Airbnb to the next level.
AIRBNB HAS ATTRACTED LEADERS WHO BELIEVE DEEPLY IN ITS CULTURE. THE OPPORTUNITY NOW IS TO TURN THAT BELIEF INTO GREATER OWNERSHIP OF WHAT COMES NEXT.
20
LEADERS PER COHORT
January 27
KICK-OFF
The kickoff and the experience are the core of the proposal. The six-month leadership development programme is included as an addition to enhance the experience, sitting between the kick-off and Experience for each cohort.
01 · The Opportunity
A DECADE LONG PARTNERSHIP
Airbnb has been part of The Tempest Two's story throughout our ten years of existence. From leadership offsites in London to keynotes in Dublin and Portland, we have an established history of bringing our approach to Airbnb teams. This proposal builds on that relationship to support the next chapter of Airbnb leadership.
The opportunity is leaders who stretch their own ambition, set a high standard through their actions and give their teams the confidence and support to do the same. Stronger relationships across functions will help them take responsibility for collective progress beyond their immediate teams.
What follows is a kickoff that brings every leader into the same room, and an experience in Yosemite that makes it stick. Alongside those two, and entirely optional, we have set out a six-month leadership programme for a cohort of 20, in case Airbnb wants to go deeper than the brief asked for.
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02 · The Outcomes
What should be different
Own Airbnb's next chapter
Leaders turn pride in Airbnb's culture into personal responsibility for driving the business forward and shaping that culture through their actions.
Stretch yourself
Leaders test self-imposed limits, approach unfamiliar challenges with curiosity and take ownership when the route is uncertain.
Lead across boundaries
Leaders build trust across functions by working through challenge together, supporting one another and taking responsibility for a shared goal.
Grow ambition within your team
Within the first month, leaders hold individual growth conversations with each team member, agreeing a meaningful stretch opportunity and the support needed to pursue it.
03 · Why This Approach
Useful, not forgettable
Traditional leadership development can be useful but forgettable: a series of ideas consumed in a room, with limited connection to the moments when leadership is tested. This programme would put leaders into an unfamiliar but carefully designed environment, create a meaningful degree of stretch, and use expert facilitation to turn the experience into practical behaviour.
The Tempest Two exists to show people what they are capable of. We aren't a traditional leadership company, and believe that true growth only happens when you remove people from the classroom, and get them working together in a way that feels uncomfortable & original.
Core design principles
Participation over consumption
Leaders learn through action, reflection and discussion, not a sequence of presentations.
Inclusive stretch
Routes and roles scale to different abilities while preserving a shared objective, meaningful challenge and dignity for every participant.
Designed for transfer
Every challenge links explicitly to Airbnb leadership, and each leader commits to growth conversations with every team member inside the first month.
Part One · Kickoff, San Francisco
The Explorer's Mindset
Everyone starts here. A keynote and a half-day experience in San Francisco, for the full leadership group. This acts as the starting point of the project, connecting belief in Airbnb's culture with responsibility for shaping what comes next. A great opportunity to set intentions, build relationships between leaders but also with ourselves, and kick-off the project.
All
Leaders invited
45-60
Minute keynote
2 Hour
EXPEDITION EXPERIENCE
0.5
DAYS REQUIRED
The keynote
A high-energy, story-led session about removing the word can't, stretching personal ambition and taking ownership when the route is unclear, drawn from a decade of expeditions and the leadership work that came out of them.
Airbnb-specific content shaped around the new cultural work and the realities leaders are navigating now.
Original stories and practical principles from our expeditions and work with leadership teams.
Audience participation so the event models the behaviour it is advocating.
A simple leadership challenge that every attendee takes back to their team.
The Expedition
Team building that actually works! The Expedition is our team challenge, run across the city, where leaders put the keynote takeaways into practice inside the same afternoon they heard it. It is competitive, physical enough to feel real, and designed so no team can succeed without someone stepping up.
One city, many routes
Teams move across San Francisco solving a sequence of challenges, with no single obvious route and no leader appointed for them.
Decisions under time pressure
Information arrives incomplete and late. Teams have to commit, adapt and keep moving rather than wait for certainty.
Built on our own app
Our Expedition platform tracks progress, releases challenges and keeps a live leaderboard, so the whole room shares one story.
Deliberately cross-functional
Teams are mixed by function and seniority, so the relationships formed are the ones that are hardest to build day to day.
Part Two · The Experience
The Yosemite pilot
We take 20 leaders to Yosemite for a leadership retreat: three nights, two full days, deliberately mixed by function and background.
Yosemite gives the pilot retreat the right combination of proximity, scale and symbolism: accessible from San Francisco, meaningfully removed from normal work, and authentically connected to our own story on El Capitan.
20
Leaders per group
3
Nights
2
Full days
These leaders will have experienced retreats, away days and excellent hospitality before. Our ambition is to create something distinctive enough that they return to Airbnb proud to have taken part, with a story they want to share and an experience colleagues look forward to joining.
We would design the entire journey with the same care: the way the invitation arrives, the anticipation built through pre-experience communications, the welcome, facilitation, challenges and hospitality, and the post-experience communications that help the learning travel.
Part Two · Learn And Design For Scale
A system, not an itinerary
Within two weeks of the pilot we deliver a concise review of participant response, delivery quality and recommended refinements. This data will then allow us to pull a plan together for a scaled approach to the remaining group of leaders, exploring international locations.
Shared principles, facilitation, reflection and application stay consistent. The environment and physical challenge change by season and region.
Three possible settings
Swipe to explore each setting
Yosemite
Recommended 2027 pilot
Lake Tahoe
US alternative or later cohort
Nordic winter
Premium global version once proven
Leadership Development
Six months. One transformation.
To truly enhance the programme, we propose a six-month, cohort-based programme for 20 leaders. Each month targets a single capability that adaptable leaders rely on, and builds it through a repeating rhythm of learning, real-world challenge and reflection. The programme would run between the kick-off and the Experience.
6
Months
20
Leaders in the cohort
4
Stage monthly loop
6
Capabilities built
Our four-stage framework
Every month runs the same loop. We teach the idea, we make them use it for real, we hold them accountable while they do, and we bring the learning back to the group. Six times over. That is how insight becomes instinct.
Learn
A focused 90-minute workshop opening the month's theme with a clear framework and group discussion.
Shared language and awareness, grounded in their real context.
Apply
Each leader commits, in front of the group, to a challenge that forces them to practise the capability for real.
This is the rep. Application is where behaviour actually changes.
Check-in
A personal mid-month touchpoint while the challenge is live, keeping momentum and accountability high.
Support at the exact moment most programmes lose people.
Reflect
The cohort reconvenes to share what happened, what they learned, and what it cost them.
Peer reflection embeds the change and deepens the cohort bond.
Six months. Six capabilities.
Sequenced with intent, building from composure under pressure out towards leading a whole team through change. Each theme can be shaped around the realities Airbnb leaders are navigating that month.
01
Performing under pressure
Stay clear, decisive and effective when the load is heaviest and the stakes are real.
02
Building high-performing habits
Install the systems that sustain performance long after motivation runs dry.
03
Increasing personal agency
Move from passenger to driver, owning outcomes instead of circumstances.
04
Leading with courage
Act decisively despite fear, discomfort and risk, and have the conversations others avoid.
05
Navigating uncertainty
Make strong calls without the full picture, adapt as conditions change, and keep moving.
06
Leading others through change
Carry a team through disruption with clarity and confidence.
What the six months include
Six monthly modules, each a facilitated 90-minute workshop led by The Tempest Two
A structured personal challenge every month, applied in real work rather than in the room
Monthly individual check-ins to sustain momentum and accountability
Group reflection sessions that embed the learning across the cohort
Flexible delivery, in person or virtual, built around how the cohort works
All frameworks, tools and materials for every participant to keep
What changes
One clear shift: a leader who is better at adapting and thriving when things are uncertain, fast-moving or hard. Not just steadier in themselves, but the fixed point their whole team navigates by.
Freezes or defaults to the old way when pressure lands
Holds their nerve and makes the call
Waits for certainty before making a move
Makes strong calls with incomplete information, then adjusts
Reacts to whatever circumstances throw at them
Owns the outcome and drives it forward
Avoids discomfort and the hard conversations
Steps into discomfort on purpose, knowing that is where growth lives
Protects themselves when change hits
Steadies the team and carries others through it
04 · Commercials
A single rate card
Each part of the programme is priced on its own. Travel, accommodation and production are not included and can be explored seperately . Figures below are placeholders while we finalise them.
SF Kickoff
Keynote and half-day Expedition in San Francisco, all leaders
$50,000
Yosemite Experience
Per group of 20, three nights, two days, facilitation and hosting
$40,000
Leadership programme (optional add-on)
Six months, cohort of 20, monthly workshops and check-ins
$10,000 per leader
Travel, stays and production
Accommodation, guides, partners and on-the-ground production
TBC
The kickoff and the Yosemite experience are the core of the proposal. The six-month leadership programme is priced separately as an optional add-on. The retreat cost falls as more groups are committed within the same season. Costs exc travel & expenses.
The investment sits far below a flagship business-school programme. It sits further below the cost of losing one capable leader who checks out in the middle of a change they were not equipped to lead.
05 · Measuring Success
Signals over impressions
The measurement approach should be designed with Airbnb's internal analytics team before the first cohort, combining immediate experience data with evidence of behaviour and network effects over time.
Before
Baseline sense of ownership for Airbnb's progress, confidence in taking on unfamiliar challenges, approach to supporting team members' growth, and strength of cross-functional relationships.
Immediately after
Quality and relevance of the experience, willingness to stretch and take ownership, strength of new peer relationships, pride in having participated, clarity of the first-month commitment, and likelihood of recommending the programme.
30 to 90 days
Completion of individual growth conversations, stretch opportunities and support agreed, early progress and feedback from team members, examples of cross-functional collaboration and continued cohort contact.
Across the rollout
Participant pride and positive word of mouth, interest in future cohorts and referrals, diversity of participation, completion, recurring behavioural themes, and evidence that leaders are enabling growth within their teams.
06 · Roles And Delivery Model
Who does what
Our role
Airbnb's role
Co-design the leadership narrative and programme architecture.
Provide the cultural context, leadership expectations and executive sponsor input.
Create and deliver the keynote and the half-day Expedition in San Francisco.
Confirm the kickoff date, audience and place within the wider agenda.
Facilitate the six-month programme, host the monthly check-ins and design the Yosemite retreat end to end.
Select the cohort of 20 and provide accessibility, travel and participant requirements.
Capture learning, report on impact and recommend the model for wider rollout.
Partner on measurement through the internal analytics team and decide which option to run.
For logistics, we can either lead end-to-end production and supplier coordination or work alongside Airbnb's existing events partner. The right model can be agreed once the option, group size and internal ownership are confirmed. If The Tempest Two handle production, we will need to charge an additional management fee.
07 · Decisions For The Next Conversation
Confirm the kickoff and Yosemite experience, and whether the optional six-month programme is included.
Confirm the kickoff date, audience size and agenda slot in San Francisco.
Confirm how the cohort of 20 is selected, and how many groups follow.
Agree the Yosemite window, accessibility needs and travel approach.
Agree whether Airbnb, an incumbent agency or our team owns production.
Define the evidence Airbnb needs in order to commit to a wider rollout.
ONE 60-MINUTE WORKING SESSION. ONE CONNECTED PROGRAMME.
A 60-minute working session to shape the programme Airbnb wants, resolve the delivery decisions above and confirm the commercials. Following that session we would develop the keynote concept, the detailed Yosemite itinerary, the delivery team, the risk and accessibility plan and the measurement framework for approval.