100+ Questions

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This booklet is the first installment in a series that will provide a complete book and experience I am calling “The Exceptional Executive’s Field Guide”. This guide is for executives who wish to lead their software development organizations through the chaos of the wild to their highest potential.

An Overview

Project teams should build smart, aggressive plans that enable them to make commitments to their management and ultimately their customers. A smart plan is one that is well thought out to provide the quickest, high-value option possible. The “quickest” refers to the design approach. Being quick should always be paired with commitments the team can keep and even beat.

I have found over and over again teams build plans and deliver results based on the questions that leaders ask. For example, one vice president asked repeatedly for software developers to, “hurry up and get the software to testers so they could start finding the defects.” The developers of course obliged and the testers found so many defects it took twice as long as development to find and fix enough of them to deliver a working product.

Building smart plans quickly with low effort requires leadership to ask the questions that drive the kind of results you want. In other words, this book of questions was created to set and reinforce expectations of excellence in the teams that build your products.

The questions are overlapping on purpose. I expect you to vary the questions and keep your teams thinking. This can be done by asking the right questions in as many diverse ways as possible over multiple project reviews. For any project plan review, please add your own situational awareness and judgment. I expect you to customize the questions for your situation, eliminate questions that are irrelevant, and be sure to ask questions that are not listed here but critical to your organization.