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tips and stories to help you
execute a road map effectively6
Andrew Hsu
About me...
Past
Electrical engineer for oil-refineries
Product manager
Present
Building high performing cultures
tip #1
Spend time with what’s difficult
a story about...
Users reporting the site is down
before we know.
Spend time with what’s difficult
Client - “The site is down.”
Spend time with what’s difficultSpend time with what’s difficult
Client - “The site is down.”
Me: “Client’s saying the site is down,
what’s going on?”
Spend time with what’s difficultSpend time with what’s difficult
Client - “The site is down.”
Me: “Client’s saying the site is down,
what’s going on?”
Engineering: <silence>
Spend time with what’s difficultSpend time with what’s difficult
Client - “The site is down.”
Me: “Client’s saying the site is down,
what’s going on?”
Engineering: <silence>
Me: “Marco?”
Spend time with what’s difficultSpend time with what’s difficult
Client - “The site is down.”
Me: “Client’s saying the site is down,
what’s going on?”
Engineering: <silence>
Me: “Marco?”
Engineering: “We’re looking into it.”
Spend time with what’s difficultSpend time with what’s difficult
Problem is fixed.
Service restored.
Spend time with what’s difficultSpend time with what’s difficult
Spend time with what’s difficultSpend time with what’s difficult
Client replies are sent.
I hope we retro properly and it doesn’t happen again.
Me: “How can we not know the site’s
down before someone else?”
Engineering: “It’s complicated.”
Spend time with what’s difficultSpend time with what’s difficult
1 month later
Spend time with what’s difficultSpend time with what’s difficult
Client - “The site is down.”
Spend time with what’s difficultSpend time with what’s difficult
Me: ugh.
Client - “The site is down.”
Spend time with what’s difficultSpend time with what’s difficult
“Seriously, again?”
“It’s complicated.”
Spend time with what’s difficultSpend time with what’s difficult
Spending the time required.
Spend time with what’s difficultSpend time with what’s difficult
Don’t just hope it was fixed.
Spend time with what’s difficultSpend time with what’s difficult
● “What broke?”
● “How did it break?”
● “How are the broken pieces interconnected?”
Spend time with what’s difficultSpend time with what’s difficult
● “Access completely revoked when one item fails.”
● “The front end sends false alarms.”
● “The back end alert is not interpretable.”
Spend time with what’s difficultSpend time with what’s difficult
Definitive next steps defined and put into our work queue.
Spend time with what’s difficultSpend time with what’s difficult
How to notice, where you need to spend time...
● People you regularly shy away from speaking with
● Persistent problems that aren’t improving
● Any problem without definitive next steps
● “That’s so weird”
● Where you feel a sense of urgency and your team does
not match that
Spend time with what’s difficult
tip #2
Answer your own first questions
a story about...
shifting strategies
Answer your own first questions
The strategy keeps
changing.
Answer your own first questionsAnswer your own first questions
You’re upset
The team is upset.
Answer your own first questionsAnswer your own first questions
“What are YOU doing?”
“Why does the strategy keep shifting?”
“How can we ship if everything keeps changing?”
Answer your own first questionsAnswer your own first questions
Answering the first questions.
Answer your own first questionsAnswer your own first questions
“What are YOU doing?”
They’re trying to make the company successful.
“Why does the strategy keep shifting?”
They’ve learned something new, seen something new, noticed
that what was planned is not working.
“How can we ship if everything keeps changing?”
We need to prime the team to adapt more quickly because the
market keeps shifting.
Answer your own first questionsAnswer your own first questions
Shape your new convo.
Answer your own first questionsAnswer your own first questions
“The strategy has shifted a lot lately which is causing the team and I
anxiety. I’m guessing this is due to: the old plan not working, you
found something better, you learned something new.
To help us adapt better, what did you learn? What changed? etc...
<conversation>
To keep us moving, I believe (1) This is the new impact goal (2) I
will convey new goals for the team as X, Y, and Z (3) Can we start
regular Friday sync ups so I can update the team on Mondays.
WDYT?
Answer your own first questionsAnswer your own first questions
Application
● Write down your first questions / reactions
● Answer them on your own
Use your answers to:
● Present your understanding of the current situation
● Present a potential solution
● Ask stakeholders what’s changed and what they think
Answer your own first questionsAnswer your own first questions
tip #3
Find a translator
a story about...
Why doesn’t anyone else feel my
urgency
Find a translator
I look at JIRA and know
we aren’t going to “make
it.”
Find a translator
Stress
Find a translator
We don’t deliver.
Find a translator
Repeat.
Find a translator
One day I start talking to
an engineer about my
frustration.
Find a translator
I’ve found a translator.
Find a translator
Me: “I’m stressed….”
Find a translator
Me: “I’m stressed….”
Engineering: “Why?
Find a translator
Me: “I’m stressed….”
Engineering: “Why?
Me: “I know we’re not going to deliver”
Find a translator
Me: “I’m stressed….”
Engineering: “Why?
Me: “I know we’re not going to deliver”
Engineering: “I understand what you’re
saying, but I don’t know how to fix it.”
Find a translator
Engineering: “There’s nothing in JIRA
and no obvious problems for us to act
on.”
Me: “What do you mean you don’t
know…”
Engineering: “I understand what you’re
saying, but I don’t know how to fix it.”
Find a translator
Immediate: Fill JIRA sooner with bugs and tickets so people
can act upon the issues.
New problem: Find a way to convey standard % of sprint
that’s taken by QA, bug fixing, and “urgent requests.”
Find a translator
How to know you likely need a translator
● How do they not get this?
● I can’t seem to get my point across
● I can’t explain what I see to people
● You’ve been struggling to change things for months,
and things are not changing
Find a translator
tip #4
Keep pulling to understand
customer impact
a lesson from
performance review conversations
Keep pulling to understand customer impact
“I feel like I’m being micro-managed”
“You are being micro-managed.”
Keep pulling to understand customer impact
“I always hit my deadlines.”
“You always hit YOUR deadlines.”
Keep pulling to understand customer impact
We always need to be asking questions and helping each
other hit the client deadlines and client impact.
Keep pulling to understand customer impact
“If you don’t want to be pushed, you need to pull.”
Keep pulling to understand customer impact
How to know when you need to pull
● Lack of clarity on how client will be delivered
● Lack of clarity on when client delivery is
● Not confident we can deliver
● Any time you are blocked
● When you see holes in your logic
● Lack of consensus with all stakeholders for client launch
Keep pulling to understand customer impact
tip #5
Teach in story
a story about...
timelines
Teach in story
Monday kick off structure
● Week 1 - client dates
● Week 1 - features
● 4 week - client dates
● 4 week - features
Teach in story
Monday kick off
Invites need to be sent to
launch a client this
Wednesday.
Teach in story
Thursday
“Hey did you send those
invites?”
Teach in story
Thursday
“Hey did you send those
invites?”
“What invites?”
Teach in story
… I trust nothing
Teach in story
Tell stories about what the expected stakeholder
experience is.
Teach in story
“On Wednesday, our Agent (George Clooney), will be
presenting to 150 people at Universal Studios.
After he presents, he will direct them all to register. They will
go to their emails while in this meeting and look for the
registration link.
We need to make sure the client has the email and George
doesn’t have a terrible time”
Who is on point for this?
Teach in story
How to know when to tell stories
● Anything that has a client impact
● Features
● Releases
● Timelines
Teach in story
tip #6
Be positive
a story about...
me
Be positive
a story about...
me + Esley
Be positive
How to notice you’re not optimistic
● I’m bored
● “I have to do this”
● “I should do this”
● Not being excited about going to work
Be positive
How to be more optimistic
● Ask yourself “how have I already achieved what I’m
seeking to do.”
● Ask yourself: “what’s the story I would tell someone
about what went well last week.”
● Go visit your clients and help them
● Work with people who work with clients
● Work with someone optimistic
Be positive
Recap
1. Spend time with what’s difficult
2. Answer your own first questions
3. Find a translator
4. Keep pulling to understand customer impact
5. Teach in story
6. Be positive
thanks!!
Questions?
andrew.hsu@vegafactor.com
www.vegafactor.com
Appendix

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Executing a roadmap: Operationalizing a road map with your team, leadership, and client

  • 1. tips and stories to help you execute a road map effectively6 Andrew Hsu
  • 2. About me... Past Electrical engineer for oil-refineries Product manager Present Building high performing cultures
  • 3. tip #1 Spend time with what’s difficult
  • 4. a story about... Users reporting the site is down before we know. Spend time with what’s difficult
  • 5. Client - “The site is down.” Spend time with what’s difficultSpend time with what’s difficult
  • 6. Client - “The site is down.” Me: “Client’s saying the site is down, what’s going on?” Spend time with what’s difficultSpend time with what’s difficult
  • 7. Client - “The site is down.” Me: “Client’s saying the site is down, what’s going on?” Engineering: <silence> Spend time with what’s difficultSpend time with what’s difficult
  • 8. Client - “The site is down.” Me: “Client’s saying the site is down, what’s going on?” Engineering: <silence> Me: “Marco?” Spend time with what’s difficultSpend time with what’s difficult
  • 9. Client - “The site is down.” Me: “Client’s saying the site is down, what’s going on?” Engineering: <silence> Me: “Marco?” Engineering: “We’re looking into it.” Spend time with what’s difficultSpend time with what’s difficult
  • 10. Problem is fixed. Service restored. Spend time with what’s difficultSpend time with what’s difficult
  • 11. Spend time with what’s difficultSpend time with what’s difficult Client replies are sent. I hope we retro properly and it doesn’t happen again.
  • 12. Me: “How can we not know the site’s down before someone else?” Engineering: “It’s complicated.” Spend time with what’s difficultSpend time with what’s difficult
  • 13. 1 month later Spend time with what’s difficultSpend time with what’s difficult
  • 14. Client - “The site is down.” Spend time with what’s difficultSpend time with what’s difficult
  • 15. Me: ugh. Client - “The site is down.” Spend time with what’s difficultSpend time with what’s difficult
  • 16. “Seriously, again?” “It’s complicated.” Spend time with what’s difficultSpend time with what’s difficult
  • 17. Spending the time required. Spend time with what’s difficultSpend time with what’s difficult
  • 18. Don’t just hope it was fixed. Spend time with what’s difficultSpend time with what’s difficult
  • 19. ● “What broke?” ● “How did it break?” ● “How are the broken pieces interconnected?” Spend time with what’s difficultSpend time with what’s difficult
  • 20. ● “Access completely revoked when one item fails.” ● “The front end sends false alarms.” ● “The back end alert is not interpretable.” Spend time with what’s difficultSpend time with what’s difficult
  • 21. Definitive next steps defined and put into our work queue. Spend time with what’s difficultSpend time with what’s difficult
  • 22. How to notice, where you need to spend time... ● People you regularly shy away from speaking with ● Persistent problems that aren’t improving ● Any problem without definitive next steps ● “That’s so weird” ● Where you feel a sense of urgency and your team does not match that Spend time with what’s difficult
  • 23. tip #2 Answer your own first questions
  • 24. a story about... shifting strategies Answer your own first questions
  • 25. The strategy keeps changing. Answer your own first questionsAnswer your own first questions
  • 26. You’re upset The team is upset. Answer your own first questionsAnswer your own first questions
  • 27. “What are YOU doing?” “Why does the strategy keep shifting?” “How can we ship if everything keeps changing?” Answer your own first questionsAnswer your own first questions
  • 28. Answering the first questions. Answer your own first questionsAnswer your own first questions
  • 29. “What are YOU doing?” They’re trying to make the company successful. “Why does the strategy keep shifting?” They’ve learned something new, seen something new, noticed that what was planned is not working. “How can we ship if everything keeps changing?” We need to prime the team to adapt more quickly because the market keeps shifting. Answer your own first questionsAnswer your own first questions
  • 30. Shape your new convo. Answer your own first questionsAnswer your own first questions
  • 31. “The strategy has shifted a lot lately which is causing the team and I anxiety. I’m guessing this is due to: the old plan not working, you found something better, you learned something new. To help us adapt better, what did you learn? What changed? etc... <conversation> To keep us moving, I believe (1) This is the new impact goal (2) I will convey new goals for the team as X, Y, and Z (3) Can we start regular Friday sync ups so I can update the team on Mondays. WDYT? Answer your own first questionsAnswer your own first questions
  • 32. Application ● Write down your first questions / reactions ● Answer them on your own Use your answers to: ● Present your understanding of the current situation ● Present a potential solution ● Ask stakeholders what’s changed and what they think Answer your own first questionsAnswer your own first questions
  • 33. tip #3 Find a translator
  • 34. a story about... Why doesn’t anyone else feel my urgency Find a translator
  • 35. I look at JIRA and know we aren’t going to “make it.” Find a translator
  • 37. We don’t deliver. Find a translator
  • 39. One day I start talking to an engineer about my frustration. Find a translator
  • 40. I’ve found a translator. Find a translator
  • 42. Me: “I’m stressed….” Engineering: “Why? Find a translator
  • 43. Me: “I’m stressed….” Engineering: “Why? Me: “I know we’re not going to deliver” Find a translator
  • 44. Me: “I’m stressed….” Engineering: “Why? Me: “I know we’re not going to deliver” Engineering: “I understand what you’re saying, but I don’t know how to fix it.” Find a translator
  • 45. Engineering: “There’s nothing in JIRA and no obvious problems for us to act on.” Me: “What do you mean you don’t know…” Engineering: “I understand what you’re saying, but I don’t know how to fix it.” Find a translator
  • 46. Immediate: Fill JIRA sooner with bugs and tickets so people can act upon the issues. New problem: Find a way to convey standard % of sprint that’s taken by QA, bug fixing, and “urgent requests.” Find a translator
  • 47. How to know you likely need a translator ● How do they not get this? ● I can’t seem to get my point across ● I can’t explain what I see to people ● You’ve been struggling to change things for months, and things are not changing Find a translator
  • 48. tip #4 Keep pulling to understand customer impact
  • 49. a lesson from performance review conversations Keep pulling to understand customer impact
  • 50. “I feel like I’m being micro-managed” “You are being micro-managed.” Keep pulling to understand customer impact
  • 51. “I always hit my deadlines.” “You always hit YOUR deadlines.” Keep pulling to understand customer impact
  • 52. We always need to be asking questions and helping each other hit the client deadlines and client impact. Keep pulling to understand customer impact
  • 53. “If you don’t want to be pushed, you need to pull.” Keep pulling to understand customer impact
  • 54. How to know when you need to pull ● Lack of clarity on how client will be delivered ● Lack of clarity on when client delivery is ● Not confident we can deliver ● Any time you are blocked ● When you see holes in your logic ● Lack of consensus with all stakeholders for client launch Keep pulling to understand customer impact
  • 57. Monday kick off structure ● Week 1 - client dates ● Week 1 - features ● 4 week - client dates ● 4 week - features Teach in story
  • 58. Monday kick off Invites need to be sent to launch a client this Wednesday. Teach in story
  • 59. Thursday “Hey did you send those invites?” Teach in story
  • 60. Thursday “Hey did you send those invites?” “What invites?” Teach in story
  • 61. … I trust nothing Teach in story
  • 62. Tell stories about what the expected stakeholder experience is. Teach in story
  • 63. “On Wednesday, our Agent (George Clooney), will be presenting to 150 people at Universal Studios. After he presents, he will direct them all to register. They will go to their emails while in this meeting and look for the registration link. We need to make sure the client has the email and George doesn’t have a terrible time” Who is on point for this? Teach in story
  • 64. How to know when to tell stories ● Anything that has a client impact ● Features ● Releases ● Timelines Teach in story
  • 67. a story about... me + Esley Be positive
  • 68. How to notice you’re not optimistic ● I’m bored ● “I have to do this” ● “I should do this” ● Not being excited about going to work Be positive
  • 69. How to be more optimistic ● Ask yourself “how have I already achieved what I’m seeking to do.” ● Ask yourself: “what’s the story I would tell someone about what went well last week.” ● Go visit your clients and help them ● Work with people who work with clients ● Work with someone optimistic Be positive
  • 70. Recap 1. Spend time with what’s difficult 2. Answer your own first questions 3. Find a translator 4. Keep pulling to understand customer impact 5. Teach in story 6. Be positive