Verb (5-dan, う, transitive)
1. to choose at one's own discretion
お菓子を適当に見計らって買ってきて。Pick out some snacks as you see fit and buy them.
2. to choose when to do something; to estimate (the time for something)
タイミングを見計らって出て行けばいいのだな。So I should just wait for the right moment and leave.