BoSUSA25 | Claire Lew | The Blind Spots That Break Us – What Leaders Are Missing Most in the Age of AI

Claire Lew shares lessons from 24 months of working closely with CEOs and executive teams at software and AI companies. She’ll highlight the most common blind spots she’s seen where leaders have succeeded, where they’ve stumbled, and what we can learn.

You’ll leave with practical ways to help your team perform at the highest level, and to lead with clarity and confidence in an AI-accelerated world.

1. THE BLINDSPOTS
THAT BREAK US
BUSINESS OF SOFTWARE 2025
Linkedin → /clairelew
Website → canopy.is
What Leaders Are Missing Most in Age of AI

3. Who feels behind? !

5. You

6. You
Me

7. You
Me
Everyone

8. Google Translate
Uber
Spotify
Pinterest
Instagram
TikTok
ChatGPT
Months to get to 100 million global monthly active users
0 20 40 60 80
Time to Reach 100M Users
Source: UBS / Yahoo Finance

11. Compressed Change

12. Compressed Change
+ High Uncertainty

13. Compressed Change
+ High Uncertainty
= Increased Blindspots

14. TODAY
Biggest things I’ve
noticed leaders missing in
last 24 months

18. Website → canopy.is

20. Last 24 months…

21. 123
45

22. 1

24. “I just need people to
adopt AI…”

25. Only 8% of workers are
using AI daily.
(Gallup, June 2025)

26. The biggest barrier to AI
adoption isn’t technology;
it’s organizational change.-PETER YANG, Product Operator Roblox,
Creator with 139,000+ subscribed
“
”

27. TOP REASONS PEOPLE DON’T USE AI AT WORK

28. Competence Penalty: “Will I look worse if I say that AI wrote this?”
TOP REASONS PEOPLE DON’T USE AI AT WORK

29. Competence Penalty: “Will I look worse if I say that AI wrote this?”
Pride/Existential Fear: “I don’t want to be replaced.”
TOP REASONS PEOPLE DON’T USE AI AT WORK

30. Competence Penalty: “Will I look worse if I say that AI wrote this?”
Pride/Existential Fear: “I don’t want to be replaced.”
Waste of Workslop: “I don’t want to waste my time reviewing and fixing what AI created.”
TOP REASONS PEOPLE DON’T USE AI AT WORK

31. Competence Penalty: “Will I look worse if I say that AI wrote this?”
Pride/Existential Fear: “I don’t want to be replaced.”
Waste of Workslop: “I don’t want to waste my time reviewing and fixing what AI created.”
Compliance Bind: “The corporate AI tools we’re allowed to use are bad so much worse
than what I can use outside of work, so I don’t use them.”
TOP REASONS PEOPLE DON’T USE AI AT WORK

32. Competence Penalty: “Will I look worse if I say that AI wrote this?”
Pride/Existential Fear: “I don’t want to be replaced.”
Waste of Workslop: “I don’t want to waste my time reviewing and fixing what AI created.”
Compliance Bind: “The corporate AI tools we’re allowed to use are bad so much worse
than what I can use outside of work, so I don’t use them.”
Cognitive Load: “I don’t know where to start.”
TOP REASONS PEOPLE DON’T USE AI AT WORK

33. Competence Penalty: “Will I look worse if I say that AI wrote this?”
Pride/Existential Fear: “I don’t want to be replaced.”
Waste of Workslop: “I don’t want to waste my time reviewing and fixing what AI created.”
Compliance Bind: “The corporate AI tools we’re allowed to use are bad so much worse
than what I can use outside of work, so I don’t use them.”
Cognitive Load: “I don’t know where to start.”
Bandwidth Issues: “I don’t have time.”
TOP REASONS PEOPLE DON’T USE AI AT WORK

34. AI adoption in your company
is not a technology problem,
it’s a cultural transformation
problem.

35. “The way we do things.”
CULTURE IS…

36. Artifacts.
Espoused values + beliefs.
Basic underlying assumptions.
SCHEIN MODEL OF CULTURE

37. The things you do + say.
Espoused values + beliefs.
Basic underlying assumptions.
SCHEIN MODEL OF CULTURE

38. The things you do + say.
The things you say you believe.
Basic underlying assumptions.
SCHEIN MODEL OF CULTURE

39. The things you do + say.
The things you say you believe.
The things you actually believe.
SCHEIN MODEL OF CULTURE

40. Basic underlying assumptions.
The things you actually believe.
SCHEIN MODEL OF CULTURE

41. Artifacts.
EXAMPLE
AI stipend. Slack channel for AI prompts + ideas.

42. Espoused values + beliefs.
“I think it’s important to stay up-to-speed with AI.”
EXAMPLE

43. Basic underlying assumptions.
“I take a lot pride in my craftsmanship and see
using AI as a hit to what I love most about my job.”
EXAMPLE

44. Basic underlying assumptions.
“I’m worried about being replaced.”
EXAMPLE

45. Basic underlying assumptions.
“I don’t have the bandwidth to prioritize this stuff.”
EXAMPLE

46. Artifacts.
Espoused values + beliefs.
Basic underlying assumptions.
… are NOT always aligned.

47. If you want to transform culture,
you must directly address your
team’s basic underlying
assumptions.

48. (And you need to figure out
what your team’s basic
underlying assumptions are)

49. Questions around specific
moments of energy
TRY THIS
Look for contradictions.
Where does your team say one thing (e.g., “I want to use AI”) but does
another (e.g., doesn’t adopt new AI coding tool).

50. Questions around specific
moments of energy
TRY THIS
Ask yourself: What would someone
have to believe to act this way?
Where does your team say one thing (e.g., “I want to use AI”) but does
another (e.g., doesn’t adopt new AI coding tool)

51. Questions around specific
moments of energy
TRY THIS
Ask your team: “I’m noticing ___.
Could you help me understand?”
Make your intention clear that you’re not trying to punish or call out,
you’re trying to help them make progress.

52. Then, to influence basic
underlying assumptions…

53. Symbolic Framework
BOLMAN + DEAL

54. Symbolic Framework
Symbols are basic elements of culture.
BOLMAN + DEAL

55. Symbolic Framework
What is important is not what happens – but what it means.
BOLMAN + DEAL

56. Myths, vision, values.
Heroines and heroes.
Stories and fairytales.
Rituals and ceremonies.
Metaphor, humor, and play.
ORGANIZATIONAL SYMBOLS

57. Myths
What’s your team’s origin story? How can you be more
deliberate in how you share the founding of your team?
EXAMPLE

58. Myths
Shopify: Founded to “allow more people to consider [entrepreneurship] as
a career.” Reflexive AI usage →“bringing all the best tools to bear so our
merchants can be more successful than they themselves used to imagine.”
(From CEO Tobi Lutke’s April 7, 2025 internal company memo)
EXAMPLE

59. Heroines + heroes
Who in your team do you prop-up, reward, and celebrate?
EXAMPLE

60. Heroines + heroes
EXAMPLE
Whoop: Hilary Gridley, Head of Product, looks for examples of how
employees improve others’ AI fluency when reviewing promotions.

61. Heroines + heroes
EXAMPLE
Duolingo: Highlights team members at“AI Show and Tell”
at all-hands meetings.

62. Stories
What stories do you tell to exemplify the basic underlying
assumptions you want to be true?
EXAMPLE

63. Stories
EXAMPLE
Shopify: CEO Tobi Lutke created his summer 2024 all-hands talk with AI
agents and presented about that.

64. Rituals + ceremonies.
What rituals + ceremonies can help embody the basic
underlying assumptions you want to be true?
EXAMPLE

65. Rituals + ceremonies.
EXAMPLE
Duolingo:  Blocks off two hours every Friday for AI (“FriAIdays”)
experimentation and demos.

66. Play
How are you creating opportunities for play in a way that
affirms basic underlying assumptions?
EXAMPLE

67. Play
EXAMPLE
Zapier: Quarterly hackathons where best ideas are presented to leadership.

68. Once you try to shift culture,
you want to make sure your
team can stay stable + adapt…

69. Four Anchors of Stability

70. PREDICTABILITY

71. CLARITY
PREDICTABILITY

72. CONTROL
CLARITY
PREDICTABILITY

73. CONTROL
CLARITY
PREDICTABILITY
CARE

74. Case Study: Zapier
(September 30, 2025)

75. Case Study: Zapier
97% of team says they “use AI every day.”
(September 30, 2025)

76. CLARITY

77. Questions around specific
moments of energy

78. Questions around specific
moments of energy
CLARITY
Name what you’re NOT doing
specifically.
“We are not naming any new strategies today. That may come later.”

79. Questions around specific
moments of energy
Make explicit exact next steps.
“Participate in the Zapier AI Hackweek… Review and bookmark the
rapidly developing AI Enablement Coda which is a centralized resource or
AI material…..”
CLARITY

80. PREDICTABILITY

81. Questions around specific
moments of energy

82. Questions around specific
moments of energy
PREDICTABILITY
Outline the Rules of
Engagement.
“The entire executive team is committed to this basic set of rules. We
will readjust them as needed in order to stay competitive and ensure our
success.”

83. Questions around specific
moments of energy
PREDICTABILITY
Here’s what’s NOT changing.
“For our current product, our strategy and bets remain in place.”

84. Questions around specific
moments of energy
PREDICTABILITY
Create a communication cadence.
“A small leadership team will provide daily correspondence with the
executive team to keep everyone on the same page. If there is nothing to
update, just update with ‘the status quo remains’…”

85. Questions around specific
moments of energy
PREDICTABILITY
Create a communication cadence.
What would be even stronger: “Every month, I’ll record a short Loom
with an update on how I see the AI landscape changing and how that
effects our business.”

86. CONTROL

87. Questions around specific
moments of energy

88. Questions around specific
moments of energy
Offer autonomy to shape their
environment.
“We’ll cancel the next week of work during the Hackathon to enable full
company participation… ”
CONTROL

89. Questions around specific
moments of energy
Give options when there can
be options.
“Join or watch our Weekly Hangout on March 30 to learn more
about Q2 goal setting.”
CONTROL

90. Questions around specific
moments of energy
Give options when there can
be options.
“Set a Q2 personal growth goal to use AI / ChatGPT in at least one
area of your daily work. If you’re not sure how, talk with your
manager.”
CONTROL

91. Questions around specific
moments of energy
Invite them to contribute to a
plan to move forward.
“Continue to look for areas where AI can solve problems 10x better,
cheaper, or faster for our customers (and internally within our operation)
given our existing strategy and initiatives.”
CONTROL

92. Questions around specific
moments of energy
Invite them to contribute to a
plan to move forward.
What would be even stronger: “I’d love your thoughts on: What are we
missing here? How can we be even more creative about learning and
utilizing AI?”
CONTROL

93. CARE

94. Questions around specific
moments of energy
Take accountability.
“I wouldn't be much of a leader if I sugarcoated. So in the spirit of
default to transparency…”
CARE

95. Questions around specific
moments of energy
Take accountability.
What would be even stronger: “No one has all the answers —
including me. But I’m dedicated to working with you all to adapt and find
the best way forward in these times of AI…”
CARE

96. Questions around specific
moments of energy
Cultural change takes time.
Took Zapier almost 2 years to get to 97% adoption → From 65%
adoption six months after ‘Code Red’ in 2023.

97. (Anti) Case Study: Opendoor
(September 26, 2025)

98. “There will be no ‘change
management’ here.”

99. “We will help you with
resources and training,
however it is ultimately up
to you to master this skill.”

100. “I know the last few days have
not been calm or easy - but
this speed and this amount of
change is our new standard
normal from now on.”

101. We’ll see how the results
shake out…

102. You’re likely to get better
results if you tackle AI
adoption as an org culture
problem, vs. a technology
problem.

103. Basic Underlying
Assumptions
Creating a Sense
of Stability
Culture Change →

104. 12

106. “Just do it…”

107. But no one is doing it.

108. Strategy has become a
slogan.

109. BAD STRATEGY

110. BAD STRATEGY
“Go AI First”

111. BAD STRATEGY
“Go AI First”

112. GOOD STRATEGYBAD STRATEGY
“Go AI First”

113. GOOD STRATEGYBAD STRATEGY
“Go AI First”
Diagnosis: Customer expectations
have changed for our product to have
faster results.

114. GOOD STRATEGYBAD STRATEGY
“Go AI First”
Diagnosis: Customer expectations
have changed for our product to have
faster results.

115. GOOD STRATEGYBAD STRATEGY
“Go AI First”
Diagnosis: Customer expectations
have changed for our product to have
faster results.
Coherent Approach: Rethink product
from first principles for faster time-to-
value.

116. GOOD STRATEGYBAD STRATEGY
“Go AI First”
Diagnosis: Customer expectations
have changed for our product to have
faster results.
Coherent Approach: Rethink product
from first principles for faster time-to-
value.

117. GOOD STRATEGYBAD STRATEGY
“Go AI First”
Diagnosis: Customer expectations
have changed for our product to have
faster results.
Coherent Approach: Rethink product
from first principles for faster time-to-
value.
Coordinated Actions:

118. GOOD STRATEGYBAD STRATEGY
“Go AI First”
Diagnosis: Customer expectations
have changed for our product to have
faster results.
Coherent Approach: Rethink product
from first principles for faster time-to-
value.
Coordinated Actions:
(1)Teach + support team on AI skills.

119. GOOD STRATEGYBAD STRATEGY
“Go AI First”
Diagnosis: Customer expectations
have changed for our product to have
faster results.
Coherent Approach: Rethink product
from first principles for faster time-to-
value.
Coordinated Actions:
(1)Teach + support team on AI skills.
(2)Cut onboarding time by 50%.

120. GOOD STRATEGYBAD STRATEGY
“Go AI First”
Diagnosis: Customer expectations
have changed for our product to have
faster results.
Coherent Approach: Rethink product
from first principles for faster time-to-
value.
Coordinated Actions:
(1)Teach + support team on AI skills.
(2)Cut onboarding time by 50%.
(3)Prototype AI native v1 version of
product.

121. BAD STRATEGY

122. BAD STRATEGY
Goals

123. BAD STRATEGY
Goals
Vision

124. BAD STRATEGY
Goals
Vision
Mission

125. BAD STRATEGY
Goals
Vision
Mission
Catchphrase

126. GOOD STRATEGYBAD STRATEGY
Goals
Vision
Mission
Catchphrase

127. GOOD STRATEGYBAD STRATEGY
Goals
Vision
Mission
Catchphrase
“Strategy is discovering the
critical factors in a situation and
designing a way of coordinating
and focusing actions to deal
with those factors.”
- Richard Rumelt

128. RUMELT’S KERNEL

129. RUMELT’S KERNEL
CRITICAL
CHALLENGE

130. COHERENT
APPROACH
RUMELT’S KERNEL
CRITICAL
CHALLENGE

131. COORDINATED ACTION
COHERENT
APPROACH
RUMELT’S KERNEL
CRITICAL
CHALLENGE

132. NETFLIX
CRITICAL
CHALLENGE

133. NETFLIX
CRITICAL
CHALLENGE

134. NETFLIX
CRITICAL
CHALLENGE
“Physical media will die.
We’ll lose customer
relationships.”

135. NETFLIX
CRITICAL
CHALLENGE
“Physical media will die.
We’ll lose customer
relationships.”

136. COHERENT
APPROACH
NETFLIX
CRITICAL
CHALLENGE
“Physical media will die.
We’ll lose customer
relationships.”

137. COHERENT
APPROACH
NETFLIX
CRITICAL
CHALLENGE
“Physical media will die.
We’ll lose customer
relationships.”

138. COHERENT
APPROACH
NETFLIX
CRITICAL
CHALLENGE
“Physical media will die.
We’ll lose customer
relationships.”
“Own the direct
digital relationship.”

139. COHERENT
APPROACH
NETFLIX
CRITICAL
CHALLENGE
“Physical media will die.
We’ll lose customer
relationships.”
“Own the direct
digital relationship.”

140. COORDINATED ACTION
COHERENT
APPROACH
NETFLIX
CRITICAL
CHALLENGE
“Physical media will die.
We’ll lose customer
relationships.”
“Own the direct
digital relationship.”

141. COORDINATED ACTION
COHERENT
APPROACH
NETFLIX
CRITICAL
CHALLENGE
“Physical media will die.
We’ll lose customer
relationships.”
“Own the direct
digital relationship.”
(1) Acquire streaming
rights aggressively.
(2) Embed Netflix on
every consumer device.
(3) Produce original
content to lock in
subscribers.

142. “Smart people syndrome”

143. You have smart person
disease. You need to
craft your message and
make it simple and clear.-JIM ABEL (Head of HR of Triology) to
JOE LIEMANDT (CEO of Triology, now
CEO at AlphaSchool)
“
”

144. BAD STRATEGY

145. BAD STRATEGY
20-page
document

146. GOOD STRATEGYBAD STRATEGY
20-page
document

147. GOOD STRATEGYBAD STRATEGY
20-page
document
1 sentence

148. GOOD STRATEGYBAD STRATEGY
20-page
document
Rethink product from
first principles for faster
time-to-value.

149. Strategy translation

150. Natural temptation to just
repeat what you’ve been
told…

151. COSTS

152. Game of telephone
COSTS

153. Game of telephone
Can’t adapt
COSTS

154. Game of telephone
Can’t adapt
Micromanagement
COSTS

155. Resonating with a strategy
— not just repeating it —
is how someone can then
execute on the strategy.

156. Resonating, not just
repeating…

157. How?

158. Internalize the strategy
yourself.

159. INTERNALIZATION

160. •Have you taken the time to check-in with your own
response?
INTERNALIZATION

161. •Have you taken the time to check-in with your own
response?
•What resonates with you most deeply about the
new strategy?
INTERNALIZATION

162. Unpack the intent.

163. UNPACK INTENT

164. •What market insights did we noticed that prompted
this new direction?
UNPACK INTENT

165. •What market insights did we noticed that prompted
this new direction?
•What would things would look like if we were successful
at this?
UNPACK INTENT

166. •What market insights did we noticed that prompted
this new direction?
•What would things would look like if we were successful
at this?
•How do we view the prioritization and alignment of
this with our other current priorities?
UNPACK INTENT

167. Make it concrete.

168. MAKE CONCRETE

169. •What might specific goals look like for your team
(or teams you work with)?
MAKE CONCRETE

170. •What might specific goals look like for your team
(or teams you work with)?
•What might specific to-dos look like for your team
(or teams you work with)?
MAKE CONCRETE

171. Connect to compelling.

172. There are so many signals in
a company that if something
isn't explicitly stated, it gets
lost in the noise.

174. Relevant: How this applies to their job and
connects to what motivates them.

175. Relevant: How this applies to their job and
connects to what motivates them.

176. Relevant: How this applies to their job and
connects to what motivates them.
Compelling: Feels like it matters and is
interesting.

177. Something has to be at stake.
People don't change their
behavior unless there's a
clear upside.

179. Concrete examples, numbers,
and a vision of the future.

180. Concrete examples, numbers,
and a vision of the future.
“Once we implement this initiative, three months from now our support team will
transition to spending 70% on personalized onboarding experiences and proactive
customer success. A year from now, we'll have transformed our support team into a
strategic consultative function with advanced skills in customer relationships for both new
sales and retention — making your roles both more secure and more valuable.”

181. Anticipate challenges

182. Give your team a heads
up for how things might
feel day-to-day…

183. The Transition Period
“For the first few months, you'll be doing double-duty…”
“This might feel overwhelming at times, but we'll adjust workloads…”

184. The Learning Curve
“___ requires some new skills….”
“Here’s how we’re investing in training…”

185. The Changing Metrics
“We’ll now be focused on tracking…”
“Here’s how this will be reflected in performance reviews…”

186. The Emotional Journey
“It’s natural to feel unsure…”
“Here’s how we’ll celebrate wins along the way…”

187. Poor execution is often a
strategy translation
problem in disguise.

188. Execution requires a
strategy that is specific,
simple, and relevant.

189. “Just do it.”

190. Ask yourself:
Is your strategy a slogan?
Do you suffer from “smart-person syndrome”?
How much time have you spent on strategy
translation (if at all)?

191. 123

193. “Speed, speed, speed.”

195. EFFECTIVE SPEED REQUIRES

196. (1)Reference Points
EFFECTIVE SPEED REQUIRES

197. (1)Reference Points
(2)Feedback Loops
EFFECTIVE SPEED REQUIRES

198. (1)Reference Points
(2)Feedback Loops
EFFECTIVE SPEED REQUIRES

199. (1)Reference Points
(2)Feedback Loops
EFFECTIVE SPEED REQUIRES

200. REFERENCE POINTS

201. ❌ Fast directive
REFERENCE POINTS

202. ❌ Fast directive ✅ Clear expectations
REFERENCE POINTS

203. REFERENCE POINTS

204. ❌ “Can you just get this
done like this…”
REFERENCE POINTS

205. ❌ “Can you just get this
done like this…”
✅ “Here’s what success
looks like…”
REFERENCE POINTS

206. REFERENCE POINTS

207. ❌ “Please no mistakes
this time around…”
REFERENCE POINTS

208. ❌ “Please no mistakes
this time around…”
✅ “Here’s an example
of the quality of work
I’m looking for…”
REFERENCE POINTS

209. REFERENCE POINTS

210. ❌ Deadlines
REFERENCE POINTS

211. ❌ Deadlines ✅ Context
REFERENCE POINTS

212. REFERENCE POINTS

213. ❌ “I need this by
tomorrow…”
REFERENCE POINTS

214. ❌ “I need this by
tomorrow…”
✅ “Here’s what’s driving
the urgency of this…”
REFERENCE POINTS

215. REFERENCE POINTS

216. ❌ “Please work on this
instead…”
REFERENCE POINTS

217. ❌ “Please work on this
instead…”
✅ “Here’s why we’re
switching up
prioritization…”
REFERENCE POINTS

218. (1)Reference Points
(2)Feedback Loops
EFFECTIVE SPEED REQUIRES

219. (1)Reference Points
(2)Feedback Loops
EFFECTIVE SPEED REQUIRES

220. FEEDBACK LOOPS

221. ❌ “What are we
working on?”
FEEDBACK LOOPS

222. ❌ “What are we
working on?”
✅ “What are we
learning?”
FEEDBACK LOOPS

223. FEEDBACK LOOPS

224. ❌ “What can I help you
with?”
FEEDBACK LOOPS

225. ❌ “What can I help you
with?”
✅ “Do you feel like
you’re being set up to
fail?”
FEEDBACK LOOPS

226. FEEDBACK LOOPS

227. ❌ “How do we move
faster?”
FEEDBACK LOOPS

228. ❌ “How do we move
faster?”
✅ “If you had to guess,
what do you think is the
underlying reason that’s
contributing our current
pace?”
FEEDBACK LOOPS

229. FEEDBACK LOOP TOUCHPOINTS

230. FEEDBACK LOOP TOUCHPOINTS
•Weekly Leadership Meetings

231. FEEDBACK LOOP TOUCHPOINTS
•Weekly Leadership Meetings
•Manager 1:1s with Directs

232. FEEDBACK LOOP TOUCHPOINTS
•Weekly Leadership Meetings
•Manager 1:1s with Directs
•Weekly Team Meetings

233. FEEDBACK LOOP TOUCHPOINTS
•Weekly Leadership Meetings
•Manager 1:1s with Directs
•Weekly Team Meetings
•Skip-Level Meetings

234. FEEDBACK LOOP SYSTEMS

235. FEEDBACK LOOP SYSTEMS
•Monthly Pulse Check

236. FEEDBACK LOOP SYSTEMS
•Monthly Pulse Check
•Pulse-survey that asks: “What’s one thing that’s confusing you
or slowing you down?”

237. FEEDBACK LOOP SYSTEMS
•Monthly Pulse Check
•Pulse-survey that asks: “What’s one thing that’s confusing you
or slowing you down?”
•All-Company AMAs

238. FEEDBACK LOOP SYSTEMS
•Monthly Pulse Check
•Pulse-survey that asks: “What’s one thing that’s confusing you
or slowing you down?”
•All-Company AMAs
•Monthly. Mix of 50% anonymous previously submitted
questions, 40% questions live, 10% questions you think people
might be too scared to ask but you want to answer.

239. “Speed, speed, speed.”

240. Reference points +
Feedback loops =
Avoid getting lost.

241. Ask yourself:
As you try to go faster, you have
feedback loops and reference
points to avoid getting lost?

242. 123
4

244. “My team needs to take
more ownership…”

245. Pulled into the weeds.
Projects stall.
Problems fester.

247. Two levels:

248. Two levels:
System

249. Two levels:
System
Individual

250. At the system level…

251. Positive
Problem-
Solving
Anxiety
Avoidance

252. Positive
Problem-
Solving
Anxiety
Avoidance
A team tries various responses until
something works. They’ll continue to use
this response until it ceases to work.

253. Positive
Problem-
Solving
Anxiety
Avoidance
A team tries various responses until
something works. They’ll continue to use
this response until it ceases to work.
A response is learned because team
successfully avoids anxiety by using it. It’s
likely to be repeated indefinitely.

254. Positive
Problem-
Solving
Anxiety
Avoidance
Daily sync meetings so you can spot
blockers faster. Move to weekly or
shortens them once original coordination
problems are solved.

255. Positive
Problem-
Solving
Anxiety
Avoidance
Daily sync meetings so you can spot
blockers faster. Move to weekly or
shortens them once original coordination
problems are solved.
Early on, founders reviewed every decision
to prevent big mistakes. Years later,
leaders still seek approval for every minor
action — not because it’s effective, but
because not checking in feels risky.

256. QUESTIONS TO ASK OURSELVES

257. QUESTIONS TO ASK OURSELVES
•Do we dismiss quick experiments?

258. QUESTIONS TO ASK OURSELVES
•Do we dismiss quick experiments?
•Do we punish fast failures?

259. QUESTIONS TO ASK OURSELVES
•Do we dismiss quick experiments?
•Do we punish fast failures?
•Do we shut down ideas too quickly?

260. QUESTIONS TO ASK OURSELVES
•Do we dismiss quick experiments?
•Do we punish fast failures?
•Do we shut down ideas too quickly?
•Do we talk… but then don’t walk the walk?

261. QUESTIONS TO ASK OURSELVES
•Do we dismiss quick experiments?
•Do we punish fast failures?
•Do we shut down ideas too quickly?
•Do we talk… but then don’t walk the walk?
•Might I be complicit? How might I be unintentionally
rewarding inaction?

262. At the individual level…

263. The obvious incentives
are external….

264. The obvious incentives
are external….
Performance Reviews → Compensation, Promotions.

265. But the most powerful
“incentives” are internal.

266. “People who are intrinsically motivated
experience greater interest, excitement,
and confidence, which in turn is
associated with enhanced performance,
persistence, and creativity.”
(Deci, 2008)

267. “Intrinsic motivation remains a
strong predictor of performance
quality even when extrinsic
incentives are present.”
(Cerasoli, Nicklin, Ford, 2014)

268. Individual
Motivation
Team
Goal

269. Create a personal frame
of reference for the work.

270. Motivation Goal
EXAMPLE

271. Motivation Goal
New AI pilot
EXAMPLE

272. Motivation Goal
New AI pilotChallenge
EXAMPLE

273. EXAMPLE

274. “Intellectual challenge”
EXAMPLE

275. EXAMPLE

276. “I wanted you to work on finding the
most creative, innovative solution because
I know you’re up for the challenge”
EXAMPLE

277. EXAMPLE
Motivation Goal

278. New AI pilot
EXAMPLE
Motivation Goal

279. New AI pilot
Helpful +
recognized
by peers
EXAMPLE
Motivation Goal

280. EXAMPLE

281. “Here’s how this elevates the work
of others…”
EXAMPLE

282. EXAMPLE

283. “Here’s how it will be making people’s
work in the org more efficient and
saving people time…”
EXAMPLE

284. EXAMPLE

285. Knowledge
EXAMPLE

286. Knowledge
Challenge
EXAMPLE

287. Knowledge
Challenge
Impact
EXAMPLE

288. Knowledge
Challenge
Impact
Money
EXAMPLE

289. Knowledge
Challenge
Impact
Money
Promotion
EXAMPLE

290. Knowledge
Challenge
Impact
Money
Promotion
Recognition
EXAMPLE

291. Knowledge
Challenge
Impact
Money
Promotion
Recognition
Flexibility
EXAMPLE

292. Knowledge
Challenge
Impact
Money
Promotion
Recognition
Flexibility
Creativity
EXAMPLE

293. Okay, so let’s say you
do all this…

294. “I’d like for you to step up more
and take more ownership in
projects.”

296. A) “I want you to proactively source ideas before you come
to new meetings.”

297. A) “I want you to proactively source ideas before you come
to new meetings.”
B) “I’d like for you to set strategy, goals, track metrics for a
project and share a weekly update with me.”

298. A) “I want you to proactively source ideas before you come
to new meetings.”
B) “I’d like for you to set strategy, goals, track metrics for a
project and share a weekly update with me.”
C) “I’d like for you to make decisions without my input on
anything that is reversible.”

299. A) “I want you to proactively source ideas before you come
to new meetings.”
B) “I’d like for you to set strategy, goals, track metrics for a
project and share a weekly update with me.”
C) “I’d like for you to make decisions without my input on
anything that is reversible.”
D) “I’d like for you to set aside 20% of your time each week
to brainstorm and experiment with way to innovate with AI.”

300. ???

301. What exactly do we mean
by “take ownership”?

302. State the specific
observable behavior.

303. OBSERVABLE BEHAVIOR

304. ❌ “Take ownership”
OBSERVABLE BEHAVIOR

305. ❌ “Take ownership”
✅ “Proactively source
ideas before meetings”
OBSERVABLE BEHAVIOR

306. ❌ “Take ownership”
✅ “Set strategy, goals,
track metrics”
OBSERVABLE BEHAVIOR

307. ❌ “Take ownership”
✅ “Make decisions on
anything reversible”
OBSERVABLE BEHAVIOR

308. ❌ “Take ownership”
✅ “Set aside 20% of
time each week to
experiment with AI”
OBSERVABLE BEHAVIOR

309. Ownership is an
observable behavior.

310. Consider the incentives
for action and inaction.

311. 123
45

313. “If I could just figure out how
to incorporate AI, a lot of our
problems would go away…”

314. I don’t think this is true
for a few reasons…

315. 95% of generative AI
pilots deliver $0 return
on investment.
(Project NANDA / MIT July 2025 - 52 interviews, 153 executives surveyed,
300 public deployments)

316. Sure, some AI pilots
are failing…

317. But the viral headlines
misses some nuances…

318. Bottleneck of our
own making

319. (Project NANDA / MIT July 2025)

320. Tap into the enthusiasm,
experience, and momentum
of your early adopters.
OPPORTUNITY

321. Assign a lead to fast-
track tooling approvals
EXAMPLE

322. Have team members
nominate which tools
they’d like to try
EXAMPLE

323. EXAMPLE
AI Taskforce

324. Vanity Game

325. (Project NANDA / MIT July 2025)
“50% of GenAI budgets go
to sales and marketing, but
back-office automation
often yields better ROI.”

326. Invest in using AI to create
efficiencies, rather than only
creating new offerings to
customers.
OPPORTUNITY

327. Zapier built a workflow that checks
Zendesk tickets and identifies customers
ready for sales conversations, turning
customer support into a revenue driver.
EXAMPLE

328. Integrate vs. Reimagine

329. (Project NANDA / MIT July 2025)
“95% failure rate for enterprise AI
solutions represents
[organizations that] continue
investing in static tools that can't
adapt to their workflows.”

330. (Project NANDA / MIT July 2025)
“95% failure rate for enterprise AI
solutions represents
[organizations that] continue
investing in static tools that can't
adapt to their workflows.”

331. Instead of merely adapting
workflows, reimagine your
workflows all together.
OPPORTUNITY

332. TYPICAL STRATEGIC ORIENTATION
(John Rossman, former Amazon exec)

333. TYPICAL STRATEGIC ORIENTATION
Requirements
(John Rossman, former Amazon exec)

334. TYPICAL STRATEGIC ORIENTATION
Requirements
Build
Deploy
Measure
(John Rossman, former Amazon exec)

335. TYPICAL STRATEGIC ORIENTATION NEW STRATEGIC ORIENTATION
Requirements
Build
Deploy
Measure
(John Rossman, former Amazon exec)

336. TYPICAL STRATEGIC ORIENTATION NEW STRATEGIC ORIENTATION
Requirements
Build
Deploy
Measure
Problem
(John Rossman, former Amazon exec)

337. TYPICAL STRATEGIC ORIENTATION NEW STRATEGIC ORIENTATION
Requirements
Build
Deploy
Measure
Hypothesis
Experiment
Scale Winners Cut Failures
Problem
(John Rossman, former Amazon exec)

338. EXAMPLE
Case Study: Intercom

339. EXAMPLE
Case Study: Intercom
Build a working prototype six weeks after ChatGPT
launched. Previously plateaued, now seeing 300%+ growth.

340. AI is not as a magic wand
for business value. It’s
only as useful as our own
orientation toward it.

342. I also don’t think AI is a
magic wand because of
the way LLMs function…

352. Vision

353. AI is really good at getting
from point A to point B —
but we as leaders are
uniquely great at deciding
what point B should be in the
first place.

355. “Behind”

356. “Ahead”

357. As leaders, we define
what is “ahead.”

358. THANK YOU!
Email → [email protected]
Linkedin → /clairelew
Website → canopy.is
Newsletter → newsletter.canopy.is