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By, Amy Unger
Running a good estimation meeting is hard. It’s easy to get lost in the weeds of implementation, and let weird social interactions slip into our estimating process. You, too, may have played Estimation Blackjack without realizing it, being “out” if you give an estimate higher than everyone else’s. Calling out these bad habits is difficult: we sometimes stop seeing them, or stay silent to keep the peace. In doing so, we risk our stakeholders making critical business decisions based on bad estimates. How, then, can we improve how we estimate? Let’s start by cataloging the ways things go bad, and then considering different ways to talk about it. I will introduce a compendium of bad estimating games, anti-patterns that can emerge over time in the estimation process. You’ll walk away from this talk with new vocabulary for humorously discussing and improving your team’s estimation dynamic so you can help your business or your clients better plan for their future.

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The video titled "Estimation Blackjack and Other Games: a Comedic Compendium" featuring Amy Unger discusses the complexities and challenges of estimating work in software development. Unger draws from her extensive experience as a software engineer and consultant, highlighting the significance of accurate estimation for project success and effective communication within teams.

Key points discussed include:  
- **Importance of Estimation**: Estimation is crucial for informing stakeholders about project timelines, which is essential for making decisions regarding resources, marketing campaigns, and business strategies. Accurate estimates can influence the success of a business and help teams avoid oversights.  
- **Challenges of Estimating**: Despite the necessity of estimation, it is often fraught with inaccuracies. Estimation aims to move from uncertainty to reliability but can sometimes lead to pseudo-deadlines that misinform stakeholders.  
- **Human Element in Estimation**: Estimating involves subjective human judgment and historical performance rather than precise prediction. Engaging the entire team in estimation discussions helps improve accuracy.  
- **Bad Estimating Games**: Unger humorously outlines several "bad estimating games" that represent ineffective practices:
  - **Solitaire**: Estimating in isolation without team input.
  - **Charades**: Estimating based on unclear or incomplete information.
  - **Dummy Bridge**: Making estimates without all relevant team members present.
  - **Slot Machines**: Revealing estimates sequentially rather than simultaneously, which can influence results unduly.
  - **Estimation Blackjack**: Pressuring team members to scale down estimates for fear of higher ones being unfavorable.
  - **Resistance**: Group dynamics where more assertive voices drown out others, leading to less accurate estimates.  
- **Improving Estimation Practices**: Unger suggests embracing uncertainty, using comparative estimates, and establishing an environment where open discussions about the estimation process are welcomed. Teams should prioritize learning from estimation inaccuracies to refine their processes without assigning blame. She emphasizes that meeting time for estimation is not wasted and that clear and honest communications about uncertainties can enhance teamwork and decision-making.

In conclusion, Unger’s talk encourages teams to approach estimation collaboratively, identify and mitigate ineffective practices, and use humor and new vocabulary to normalize discussions around improving estimation dynamics. Her insights aim to empower teams to make more informed decisions that benefit their projects and organizations.

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