The Engineering Executive's Primer

Chapter 4. How to Plan

Some years back, I interviewed a senior leader for an engineering role, and asked them a question about planning. I enjoyed their response, “Ah yes, the ‘P’ word, planning.” That answer captured an oft heard perspective that planning is some sort of business curse word. Even when it goes well, planning is an objectively difficult task. When it goes poorly, the business loses months or years of potential progress.

James Carse’s Finite and Infinite Games (Free Press) proposes that you can view most things in life from two different perspectives. The first is seeing life as a series of finite games, with clear rules and specific ways to win. The second is seeing life as an infinite game, with rules that are evolved over time by its players, and where the goal is continuing to play. Although planning is often viewed as a finite, rules-heavy process, I find it much more useful to approach planning as an ongoing game with dynamic rules. It was only when I was able to look past the stated rules that I was able to become an effective planner.

Guiding your company through the dynamics of planning is uniquely impactful executive work and is an area where effective executives can greatly distinguish themselves. In this chapter, we’ll walk through:

• Discussing the default planning process at most companies

• Dividing planning into three discrete phases: financial plan, functional portfolio allocation, and roadmap

• Establishing a shared timeline across the three phases ...