Software Estimation: Demystifying the Black Art

McConnell separates an estimate from a target and a commitment, then builds a practical toolkit for producing the first of the three. He covers the cone of uncertainty, the principle of counting and computing before resorting to judgement, calibration against your own historical data, and a range of techniques from analogy and decomposition through to proxy based methods such as story points. Later chapters deal with converting effort into a schedule, the politics of being pushed towards a number, and presenting an estimate as a range without appearing evasive. Written about software, though the reasoning transfers to any planning conversation where someone is demanding a single figure.