Planning Strategies for an Engineering Executive.

Approaching Planning as an Infinite Process

Planning is often perceived as a daunting and finite task for businesses. However, it could be approached as an infinite process, where its rules are constantly evolving, and the goal is to continue to play. In this essay, we will discuss how planning could be executed as an infinite process, the default planning process at most companies, and planning’s three discrete components.

The Default Planning Process

By the time a company reaches a certain size, they usually have the same documented planning process. The executive team agrees on an annual financial plan, including a headcount plan. Every quarter or half, the executive team will create a planning artifact that outlines the plan for the upcoming quarter. Teams are responsible for managing their execution against the quarter or half plan, using a process of their choice like Scrum or Agile. There may be a monthly execution review to track progress against company goals.

However, each company has its specific details about when the process happens, what document you need to deliver to whom, and how budgeting works. There is always another layer of emergent rules based on behavior. Thus, even in companies where the executive team works together in good faith, new information could emerge that could invalidate the current plan.

Planning’s Three Discrete Components

To simplify planning and focus on its true value, it should be executed through three distinct phases that reduce the number of dependencies in each step. These are:

1. Set Your Company’s Resource Allocation Across Functions

This involves creating an annual financial plan that sets targets for revenue and expenses, broken down by function and business line. From this, you can answer questions like the relative investment into Research & Development (R&D) versus Sales & Marketing (S&M) or General & Administrative (G&A), as well as between the company’s products or business units.

2. Refresh Engineering’s Functional Portfolio Allocation

With a particular focus on Engineering’s functional portfolio allocation between functional priorities and business priorities.

3. Establish A High-level Quarter or Half Roadmap

Partner with your closest cross-functional partners, particularly Product and Sales, to establish a high-level quarter or half roadmap. This is the cross-functional agreement on the scope and timing of work to be done.

Establishing Your Financial Plan

The company’s financial plan is the foundation for all planning. It sets the targets for every business line’s revenue and each function’s expenses within that business line. The executive team will have to pull together an updated financial plan every year. This document contains a great deal of data that requires a deep understanding of what the numbers mean.

Defining Engineering’s Functional Portfolio Allocation

Companies have different views on what constitutes Engineering’s functional scope, and Security may or may not be included. Thus, the focus should on establishing a cohesive strategy that aligns Engineering’s priorities between functional priorities and business-driven priorities. This process must involve stakeholders affected by the plan.

Agreeing on The 3 to 12 Month Roadmap

A high-level quarter or half roadmap that outlines the cross-functional agreement on the scope and timing of work to be done must be established. The roadmap should be achievable and based on the corporate objectives set by the financial plan, Engineering’s functional portfolio allocation, and cross-functional partner priorities.

Establishing A Shared Timeline

All three planning components must be sequenced to ensure the creation of a shared timeline that aligns expectations across the executive team, functional teams, and cross-functional partners. This process reduces the number of dependencies and increases decision quality.

Exploring Planning’s Frequent Failure Modes

Although planning failure modes may be common, they are avoidable. Understanding why things went wrong will help in developing the right solutions. Common reasons for failure in planning include setting unrealistic targets, ignoring new information and failing to update the plan, and engaging in too much detail too soon.


Planning is difficult, but it doesn’t have to be. By treating planning as an infinite, ongoing game where rules evolve with time, companies can approach it more effectively. Simplifying the planning process into three distinct phases reduces dependencies and strengthens execution. Companies can establish a shared timeline that aligns expectations across all stakeholders and avoid frequent failure modes. By doing so, they can operate effectively and distinguish themselves as effective executives.

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