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
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
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?
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
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