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Bets, Boards and Missions
@johncutlefish
cutle.fish
Last 12 months
100s of teams
Small changes, big impact (or fail gracefully)
Shared understanding & communication
The Team
1. The messy middle
2. Framing bets
3. Explore “ownership” boundaries
4. Hack the language…
5. Designing the work taxonomy…

6A. Flattening the model…
6B. Layering in interventions and OKRs…
6C. A big, visual, hybrid board…
The messy middle…
1
1-3h 1-3d 1-3w 1-3m 1-3q 1-3y 1-3decades
Sense
Respond
1-3h 1-3d 1-3w 1-3m 1-3q 1-3y 1-3decades
Sense
Respond Messy Middle
Play the random Jira ticket game.
From a 1-3h “tasks” to a 1-3y
company bet in >3 steps
We’re working on that ticket to [the
mission of that ticket] to help us
[some higher level mission], which
will help us [some even higher level
mission], which will help us [some
even higher level mission]….
(repeating)
We’re working on Jira ticket ACT-1252 to
predictively auto-fill transaction details,
which will help us improve the efficiency
of the bank reconciliation workflow,
which will help us retain larger accounts
with in-house bookkeepers, which will
help us increase recurring revenue AND
will help us market to larger prospects
who we “lost” when they trialed the
reconciliation workflow
Which we believe will help us improve
the efficiency of the bank reconciliation
workflow by saving between 15 and 20
minutes to finish the process…



because we know 80% of customers
spend ~15 minutes per reconciliation
filling out data we have a 90%
probability of guessing accurately.
Framing things as bets…
2
Bets can be…
Big
Small
Risky
Safe
Prescriptive
Descriptive
Big batch
Increment friendly
Upfront gamble
Change bet over time
Networked/connected
Isolated
1-3h
1-3d
1-3w
1-3m
1-3q
1-3y
1-3d
Write some BetLibs
Map some bets
http://tiny.cc/you-betcha
Explore “ownership” boundaries
3
A. Build exactly this [to a predetermined specification]
B. Build something that does [specific behavior, input-output,
interaction]
C. Build something that lets a segment of customers complete [some
task, activity, goal]
D. Solve this [more open-ended customer problem]
E. Explore the challenges of, and improve the experience for,
[segment of users/customers]
F. Increase/decrease [metric] known to influence a specific business
outcome
G. Explore various potential leverage points and run experiments to
influence [specific business outcome]
H. Directly generate [short-term business outcome]
I. Generate [long-term business outcome]
A B C D E F G H I
Dev
UX
PM
A. Build exactly this [to a predetermined
specification]
B. Build something that does [specific
behavior, input-output, interaction]
C. Build something that lets a segment of
customers complete [some task,
activity, goal]
D. Solve this [more open-ended customer
problem]
E. Explore the challenges of, and improve
the experience for, [segment of users/
customers]
F. Increase/decrease [metric] known to
influence a specific business outcome
G. Explore various potential leverage
points and run experiments to influence
[specific business outcome]
H. Directly generate [short-term business
outcome]
I. Generate [long-term business outcome]
A
B
C
D
E
F
G
H
I
Team
PM
GM
Team
PM
VPoP
GM
Org 1 Org 2
Categorize a sample of work.
Make it visual.
A. Build exactly this [to a predetermined specification]
B. Build something that does [specific behavior, input-output,
interaction]
C. Build something that lets a segment of customers complete [some
task, activity, goal]
D. Solve this [more open-ended customer problem]
E. Explore the challenges of, and improve the experience for,
[segment of users/customers]
F. Increase/decrease [metric] known to influence a specific business
outcome
G. Explore various potential leverage points and run experiments to
influence [specific business outcome]
H. Directly generate [short-term business outcome]
I. Generate [long-term business outcome]
Hack the language…
4
Problems/Solutions
Projects
Experiments
“Done”
“Done”
Dependency Wrangling
Debt
Opportunities/Interventions
Missions
Bets
Decision Point
Review & Measurement
Playing Tetris
Drag
Catalog language in use.
Try subtle changes.
Designing the work taxonomy…
5
What must you
eventually know about
this work to make
good decisions at the
right cadence?
How does work appear in these queues?
How often? With advance notice? Who puts work in these queues?
Dependencies on other groups
Deadline? (real or not)
Cost of being late (or not delivering feature)
Size of effort
Expect impact of item
Ability to measure impact (and time)
Data on existing usage
Who is advocate? Who are stakeholders?
What is solution certainty? (range)
What is problem uncertainty?
Impacting current customers?
Type of design work
Core improvements
New feature development
Bandaids/fixes
Skills/functions required
Customer visibility
Collaboration model (e.g. contractor teams)
Urgency (P0, P1, P2)
Assumptions / beliefs
Learning goal? Permanence?
Risks willing to incur
Needed / caused by / blocked by tech debt
Background / prior story / veracity of data
Headwinds / blockers
Connected to core strategy?
Reactive vs proactive
Tech used
Org visibility
PIA factor / fun factor
Do not disturb - focus required
Solve tech debt / add new tech debt
When do you need to know the info?
Who needs to be around?
Tags V1 Vs.
“Got it! So we will have a PRD
template that EVERYONE needs to
fill in, and review it at each and
every handoff?”



Instead consider…
Shapes of work
Try a “design a one-pager”
exercise (or one-pager checklist)
Letter-to-the-future 

One-Pagers and Kickoff “Decks”
Flattening the model…
6A
3-9mo1-3y
Mid/Long
Term Value
North Star
Input
Input
Input
Health
Indicators
Level 1 BetsLevel 0 Bets
Value Creation Model
Beliefs, Assumptions, Strategy
Weekly Learning Users (WLUs)
# of Weekly Users who are active
and share a learning that is
consumed by at least 2 other people
in the previous 7 days.
Activated Accounts
Organizations that have reached at least 5
WLUs.
Broadcasted Learning (BL)
A chart, dashboard, or Notebook consumed by
2 or more people within a 7 day period.
Consumption of Learnings (CoL)
Total reach of BL in an organization within a 7
day period.
North Star workshop
Layering in interventions and OKRs…
6B
3-9mo1-3y
Mid/Long
Term Value
North Star
Input
Input
Input
Health
Indicators
Level 1 BetsLevel 0 Bets
Value Creation Model
Beliefs, Assumptions, Strategy
Target Input(s)
Level 2 Bets
1-3mo
3-9mo1-3y
Mid/Long
Term Value
North Star
Input
Input
Input
Health
Indicators
Level 1 BetsLevel 0 Bets
Value Creation Model
Beliefs, Assumptions, Strategy
Target Input(s)
Level 2 Bets
1-3mo
OKRs
Forecasted impact on input
Map work to Inputs.
A big, visual, hybrid board…
6C
Level 2 Bet
Target Input(s)
Level 3 Bet
Focus On

Next
To Try Trying Review
ReviewFocusing
To Try Trying Review
To Try Trying Review
Team A
Team B
Team C
1-3mo 1-3w
OKRs
Impact 

on

Input
3-9mo1-3y
Mid/Long Term
Value North Star
Input
Input
Input
Health
Indicators
Level 1 BetsLevel 0 Bets
Value Creation Model
Beliefs, Assumptions, Strategy
3mo
Observe continuously, revisit periodically
North Star



1-3 year bets
Inputs
Focusing
Trying Review
Inputs
Inputs
Inputs
Get out that tape.
Get those magnets.
http://tiny.cc/hybrid-board
Questions

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Bets, Boards, and Missions

  • 1. Bets, Boards and Missions
  • 3. Last 12 months 100s of teams Small changes, big impact (or fail gracefully) Shared understanding & communication
  • 5. 1. The messy middle 2. Framing bets 3. Explore “ownership” boundaries 4. Hack the language… 5. Designing the work taxonomy…
 6A. Flattening the model… 6B. Layering in interventions and OKRs… 6C. A big, visual, hybrid board…
  • 7. 1-3h 1-3d 1-3w 1-3m 1-3q 1-3y 1-3decades Sense Respond
  • 8. 1-3h 1-3d 1-3w 1-3m 1-3q 1-3y 1-3decades Sense Respond Messy Middle
  • 9. Play the random Jira ticket game. From a 1-3h “tasks” to a 1-3y company bet in >3 steps
  • 10. We’re working on that ticket to [the mission of that ticket] to help us [some higher level mission], which will help us [some even higher level mission], which will help us [some even higher level mission]…. (repeating)
  • 11. We’re working on Jira ticket ACT-1252 to predictively auto-fill transaction details, which will help us improve the efficiency of the bank reconciliation workflow, which will help us retain larger accounts with in-house bookkeepers, which will help us increase recurring revenue AND will help us market to larger prospects who we “lost” when they trialed the reconciliation workflow
  • 12. Which we believe will help us improve the efficiency of the bank reconciliation workflow by saving between 15 and 20 minutes to finish the process…
 
 because we know 80% of customers spend ~15 minutes per reconciliation filling out data we have a 90% probability of guessing accurately.
  • 13. Framing things as bets… 2
  • 14. Bets can be… Big Small Risky Safe Prescriptive Descriptive Big batch Increment friendly Upfront gamble Change bet over time Networked/connected Isolated
  • 15.
  • 20. A. Build exactly this [to a predetermined specification] B. Build something that does [specific behavior, input-output, interaction] C. Build something that lets a segment of customers complete [some task, activity, goal] D. Solve this [more open-ended customer problem] E. Explore the challenges of, and improve the experience for, [segment of users/customers] F. Increase/decrease [metric] known to influence a specific business outcome G. Explore various potential leverage points and run experiments to influence [specific business outcome] H. Directly generate [short-term business outcome] I. Generate [long-term business outcome]
  • 21.
  • 22. A B C D E F G H I Dev UX PM A. Build exactly this [to a predetermined specification] B. Build something that does [specific behavior, input-output, interaction] C. Build something that lets a segment of customers complete [some task, activity, goal] D. Solve this [more open-ended customer problem] E. Explore the challenges of, and improve the experience for, [segment of users/ customers] F. Increase/decrease [metric] known to influence a specific business outcome G. Explore various potential leverage points and run experiments to influence [specific business outcome] H. Directly generate [short-term business outcome] I. Generate [long-term business outcome]
  • 24. Categorize a sample of work. Make it visual.
  • 25. A. Build exactly this [to a predetermined specification] B. Build something that does [specific behavior, input-output, interaction] C. Build something that lets a segment of customers complete [some task, activity, goal] D. Solve this [more open-ended customer problem] E. Explore the challenges of, and improve the experience for, [segment of users/customers] F. Increase/decrease [metric] known to influence a specific business outcome G. Explore various potential leverage points and run experiments to influence [specific business outcome] H. Directly generate [short-term business outcome] I. Generate [long-term business outcome]
  • 28. Catalog language in use. Try subtle changes.
  • 29. Designing the work taxonomy… 5
  • 30. What must you eventually know about this work to make good decisions at the right cadence?
  • 31.
  • 32.
  • 33. How does work appear in these queues? How often? With advance notice? Who puts work in these queues? Dependencies on other groups Deadline? (real or not) Cost of being late (or not delivering feature) Size of effort Expect impact of item Ability to measure impact (and time) Data on existing usage Who is advocate? Who are stakeholders? What is solution certainty? (range) What is problem uncertainty? Impacting current customers? Type of design work Core improvements New feature development Bandaids/fixes Skills/functions required Customer visibility Collaboration model (e.g. contractor teams) Urgency (P0, P1, P2) Assumptions / beliefs Learning goal? Permanence? Risks willing to incur Needed / caused by / blocked by tech debt Background / prior story / veracity of data Headwinds / blockers Connected to core strategy? Reactive vs proactive Tech used Org visibility PIA factor / fun factor Do not disturb - focus required Solve tech debt / add new tech debt When do you need to know the info? Who needs to be around? Tags V1 Vs.
  • 34. “Got it! So we will have a PRD template that EVERYONE needs to fill in, and review it at each and every handoff?”
 
 Instead consider…
  • 36. Try a “design a one-pager” exercise (or one-pager checklist)
  • 39. 3-9mo1-3y Mid/Long Term Value North Star Input Input Input Health Indicators Level 1 BetsLevel 0 Bets Value Creation Model Beliefs, Assumptions, Strategy
  • 40. Weekly Learning Users (WLUs) # of Weekly Users who are active and share a learning that is consumed by at least 2 other people in the previous 7 days. Activated Accounts Organizations that have reached at least 5 WLUs. Broadcasted Learning (BL) A chart, dashboard, or Notebook consumed by 2 or more people within a 7 day period. Consumption of Learnings (CoL) Total reach of BL in an organization within a 7 day period.
  • 42. Layering in interventions and OKRs… 6B
  • 43. 3-9mo1-3y Mid/Long Term Value North Star Input Input Input Health Indicators Level 1 BetsLevel 0 Bets Value Creation Model Beliefs, Assumptions, Strategy Target Input(s) Level 2 Bets 1-3mo
  • 44. 3-9mo1-3y Mid/Long Term Value North Star Input Input Input Health Indicators Level 1 BetsLevel 0 Bets Value Creation Model Beliefs, Assumptions, Strategy Target Input(s) Level 2 Bets 1-3mo OKRs Forecasted impact on input
  • 45. Map work to Inputs.
  • 46. A big, visual, hybrid board… 6C
  • 47. Level 2 Bet Target Input(s) Level 3 Bet Focus On
 Next To Try Trying Review ReviewFocusing To Try Trying Review To Try Trying Review Team A Team B Team C 1-3mo 1-3w OKRs Impact 
 on
 Input 3-9mo1-3y Mid/Long Term Value North Star Input Input Input Health Indicators Level 1 BetsLevel 0 Bets Value Creation Model Beliefs, Assumptions, Strategy 3mo Observe continuously, revisit periodically
  • 48.
  • 49. North Star
 
 1-3 year bets Inputs Focusing Trying Review Inputs Inputs Inputs
  • 50.
  • 51. Get out that tape. Get those magnets.