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The 8 Deadly Sins of
Buying PeopleWare
Itamar Goldminz
Buying good software is hard!
Only 60% “met their goals”
30% deemed failures
$100M of every $1B invested is “wasted”
- PMI, “Pulse of the Profession”, 2017
Buying good software is hard!
Common mitigation strategy: look for “social proof”
Buying good software is hard!
An outsider’s perspective is helpful only after we’ve
developed our own first-principles perspective on what
“good” looks like because...
Our mileage WILL vary
My perspective
1. No underlying philosophy
The 8 Deadly Sins of Buying PeopleWare
Underlying philosophy:
Leadership = Communication + Coaching + Emotional intelligence
1. No underlying philosophy
Source: cultivate.ai
Misaligned underlying philosophy = guaranteed adoption failure
● Articulate your own philosophy first
● Extract the tool’s philosophy
● Test for alignment
1. No underlying philosophy
1. No underlying philosophy
The 8 Deadly Sins of Buying PeopleWare
2. Discounting the user
“People don’t want to be amazing at our tool, they
want to be amazing at the broader context”
Kathy Sierra - Javaranch.com founder
2. Discounting the user
We buy tools to drive human behavior change
Effective behavior change:
2. Discounting the user
Direct the Rider
(Rational mind)
Motivate the Elephant
(Emotional mind)
Shape the Path
(Environment)
Source: Switch -
how to change
things when change
is hard
Is the tool addressing all three?
How will you complement missing elements?
1. No underlying philosophy
2. Discounting the user
The 8 Deadly Sins of Buying PeopleWare
3. Evaluating in isolation
How software is sold
3. Evaluating in isolation
Know where the tool needs to begin and end
Optimize for minimizing overlap with existing tools
3. Evaluating in isolation
ATS
HRIS
Goals
Engagement
Comp
But in reality...
Look for high interoperability:
API-based ecosystem (pre-existing apps)
is better than…
APIs
is better than…
Pre-built integrations with specific tools
is better than…
Manual CSV-based data import/exports
is better than…
Closed tool (data exists in isolation)
3. Evaluating in isolation
1. No underlying philosophy
2. Discounting the user
3. Evaluating in isolation
The 8 Deadly Sins of Buying PeopleWare
4. Passive engagement
Not every piece of software is a primary system-of-record
that will always be open in the user’s browser.
4. Passive engagement
is not
If it’s low-frequency (for example, goal setting)
OR
event-triggered (for example, PTO approval)
→
the user needs to be engaged via a different always-open
system (email, phone notification)
4. Passive engagement
1. No underlying philosophy
2. Discounting the user
3. Evaluating in isolation
4. Passive engagement
The 8 Deadly Sins of Buying PeopleWare
5. Data or Insights?
5. Data or Insights?
5. Data or Insights?
5. Data or Insights?
1. No underlying philosophy
2. Discounting the user
3. Evaluating in isolation
4. Passive engagement
The 8 Deadly Sins of Buying PeopleWare
5. Data or Insights?
6. Constraining pricing
Typical pricing scheme: by-seat pricing
6. Constraining pricing
Friction with every new seat
Disincentive for wide adoption
Encourages information silos
Better pricing scheme: pay by-org-size pricing
6. Constraining pricing
1. No underlying philosophy
2. Discounting the user
3. Evaluating in isolation
4. Passive engagement
The 8 Deadly Sins of Buying PeopleWare
5. Data or Insights?
6. Constraining pricing
7. Only software
7. Only software
1. No underlying philosophy
2. Discounting the user
3. Evaluating in isolation
4. Passive engagement
The 8 Deadly Sins of Buying PeopleWare
5. Data or Insights?
6. Constraining pricing
7. Only software
8. A fool with a tool
“... is still a fool!”
8. “A fool with a tool...
B.A. Baracus
A-Team
Grady Booch
Developer of UML
8. “A fool with a tool...
Recruiting process stages and
workflow
?
?
?
OR
OR
OR
Self/Peer/Manager question prompts
Channel naming conventions and
discussion guidelines
1. No underlying philosophy
2. Discounting the user
3. Evaluating in isolation
4. Passive engagement
The 8 Deadly Sins of Buying PeopleWare
5. Data or Insights?
6. Constraining pricing
7. Only software
8. A fool with a tool
www.linkedin.com/in/itamarg/
www.medium.com/org-hacking
Itamar Goldminz
Thank You!

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The 8 deadly sins of buying people ware

  • 1. The 8 Deadly Sins of Buying PeopleWare Itamar Goldminz
  • 2. Buying good software is hard! Only 60% “met their goals” 30% deemed failures $100M of every $1B invested is “wasted” - PMI, “Pulse of the Profession”, 2017
  • 3. Buying good software is hard! Common mitigation strategy: look for “social proof”
  • 4. Buying good software is hard! An outsider’s perspective is helpful only after we’ve developed our own first-principles perspective on what “good” looks like because... Our mileage WILL vary
  • 6. 1. No underlying philosophy The 8 Deadly Sins of Buying PeopleWare
  • 7. Underlying philosophy: Leadership = Communication + Coaching + Emotional intelligence 1. No underlying philosophy Source: cultivate.ai
  • 8. Misaligned underlying philosophy = guaranteed adoption failure ● Articulate your own philosophy first ● Extract the tool’s philosophy ● Test for alignment 1. No underlying philosophy
  • 9. 1. No underlying philosophy The 8 Deadly Sins of Buying PeopleWare 2. Discounting the user
  • 10. “People don’t want to be amazing at our tool, they want to be amazing at the broader context” Kathy Sierra - Javaranch.com founder 2. Discounting the user We buy tools to drive human behavior change
  • 11. Effective behavior change: 2. Discounting the user Direct the Rider (Rational mind) Motivate the Elephant (Emotional mind) Shape the Path (Environment) Source: Switch - how to change things when change is hard Is the tool addressing all three? How will you complement missing elements?
  • 12. 1. No underlying philosophy 2. Discounting the user The 8 Deadly Sins of Buying PeopleWare 3. Evaluating in isolation
  • 13. How software is sold 3. Evaluating in isolation
  • 14. Know where the tool needs to begin and end Optimize for minimizing overlap with existing tools 3. Evaluating in isolation ATS HRIS Goals Engagement Comp But in reality...
  • 15. Look for high interoperability: API-based ecosystem (pre-existing apps) is better than… APIs is better than… Pre-built integrations with specific tools is better than… Manual CSV-based data import/exports is better than… Closed tool (data exists in isolation) 3. Evaluating in isolation
  • 16. 1. No underlying philosophy 2. Discounting the user 3. Evaluating in isolation The 8 Deadly Sins of Buying PeopleWare 4. Passive engagement
  • 17. Not every piece of software is a primary system-of-record that will always be open in the user’s browser. 4. Passive engagement is not
  • 18. If it’s low-frequency (for example, goal setting) OR event-triggered (for example, PTO approval) → the user needs to be engaged via a different always-open system (email, phone notification) 4. Passive engagement
  • 19. 1. No underlying philosophy 2. Discounting the user 3. Evaluating in isolation 4. Passive engagement The 8 Deadly Sins of Buying PeopleWare 5. Data or Insights?
  • 20. 5. Data or Insights?
  • 21. 5. Data or Insights?
  • 22. 5. Data or Insights?
  • 23. 1. No underlying philosophy 2. Discounting the user 3. Evaluating in isolation 4. Passive engagement The 8 Deadly Sins of Buying PeopleWare 5. Data or Insights? 6. Constraining pricing
  • 24. Typical pricing scheme: by-seat pricing 6. Constraining pricing Friction with every new seat Disincentive for wide adoption Encourages information silos
  • 25. Better pricing scheme: pay by-org-size pricing 6. Constraining pricing
  • 26. 1. No underlying philosophy 2. Discounting the user 3. Evaluating in isolation 4. Passive engagement The 8 Deadly Sins of Buying PeopleWare 5. Data or Insights? 6. Constraining pricing 7. Only software
  • 28. 1. No underlying philosophy 2. Discounting the user 3. Evaluating in isolation 4. Passive engagement The 8 Deadly Sins of Buying PeopleWare 5. Data or Insights? 6. Constraining pricing 7. Only software 8. A fool with a tool
  • 29. “... is still a fool!” 8. “A fool with a tool... B.A. Baracus A-Team Grady Booch Developer of UML
  • 30. 8. “A fool with a tool... Recruiting process stages and workflow ? ? ? OR OR OR Self/Peer/Manager question prompts Channel naming conventions and discussion guidelines
  • 31. 1. No underlying philosophy 2. Discounting the user 3. Evaluating in isolation 4. Passive engagement The 8 Deadly Sins of Buying PeopleWare 5. Data or Insights? 6. Constraining pricing 7. Only software 8. A fool with a tool