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.