Estimates are a contentious topic in software development. They have value in many cases but increasingly are fraught with peril. Most of our development teams hate providing estimates and many managers are starting to view them as unnecessary. As senior software leaders, how can we determine whether estimates are helpful or harmful to our teams? We are excited to be joined by Beekey Cheung, a software consultant and blogger known as Professor Beekums, who has helped many leaders and teams go from fearing estimates to using them appropriately. He'll walk us through the value of estimates, how to overcome the hesitancy many have in giving them, and how to provide better estimates.

1. An Adult Conversation About Estimates
Beekey Cheung Brittany Shear
With: Moderated by:
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3. About The Speaker
Beekey Cheung is a software consultant with specialties in project management, team building, and software
architecture. His clients are primarily startups that have reached a phase where they need to scale. Beekey has a
knack for helping companies find the right balance between delivering quickly and managing technical debt. When
not working on technology, Beekey spends his time rock climbing and trying new board games.
About The Moderator
Brittany went to Emmanuel College, where she majored in Writing, Editing, and Publishing and minored in Marketing,
Psychology, and Communications. She now works with Aggregage as an editor and webinar host on sites including
CTO Universe, Product Management Today, and Project Management Update.

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Estimates!
An Adult Conversation
About Estimates

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Estimates?!
An Adult Conversation
About Estimates

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The Value of Estimates
• Hard deadlines (e.g. a conference or a board
meeting)
• Figuring out return on investment when prioritizing
work
• Help understand the complexity of a project
An Adult Conversation
About Estimates

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Why Are Estimates Hated?
An Adult Conversation
About Estimates

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Randomness in Estimates
An Adult Conversation
About Estimates

9. 9
Performance Reviews
An Adult Conversation
About Estimates

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Our Problem
An Adult Conversation
About Estimates

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Convince Teams to Use Estimates
An Adult Conversation
About Estimates

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Good Estimate Culture
An Adult Conversation
About Estimates

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Contingencies
An Adult Conversation
About Estimates

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Internal Releases
An Adult Conversation
About Estimates

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Customers Don’t Care About JIRA
An Adult Conversation
About Estimates

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Executive Communication
An Adult Conversation
About Estimates

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Make Sure Developers Understand The Product
An Adult Conversation
About Estimates

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Story Points
An Adult Conversation
About Estimates
5 SP == 1 day?
5 SP != 1 day?
What is 5 story points then?

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Story Points Are Hard
Time != Story points
Velocity == Story points in a Sprint
Sprints == Time
An Adult Conversation
About Estimates

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Transitioning to Story Points
An Adult Conversation
About Estimates

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Order of Magnitude Estimates
Minutes: 1 - 59 minutes
Hours: 1 - 7 hours
Days: 1 - 4 days
Weeks: 1 - 3 weeks
Months: 1+ months
Years: 1+ years
An Adult Conversation
About Estimates

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R & D Projects
An Adult Conversation
About Estimates

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Automated Testing
An Adult Conversation
About Estimates

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Estimates Are a Tool
An Adult Conversation
About Estimates

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Q&A
Brittany Shear
With: Moderated by:
Software Consultant, Professor Beekums, LLC
Linkedin page: /Beekey-cheung-26b8722
Twitter ID: @PBeekums
Email: contact@professorbeekums.com
Website: professorbeekums.com
Beekey Cheung
Assistant Editor, Aggregage
Linkedin page: /cto-universe
Twitter ID: @CTOUniverse
Email: brittany.shear@aggregage.com
Website: CTOUniverse.com
www.ctouniverse.com/webinar-series/cto-universe-leadership-series/