The CTO’s Yearly Checklist

Previously published on Forbes on 8/19/2020

In a startup, as in any adventure, one needs to raise one’s head toward the horizon once in a while to ensure that one is still headed in the right direction. Well-run companies typically hold quarterly executive off-sites, and at least once per year, the product road map is refreshed. 

This is the perfect impetus to refresh everything in engineering: technology stack, tools, methodology, team and employee roles. Technology, tools or processes that used to work may become inadequate, or even break, as the company grows. A well-executed yearly review will identify the key challenges and opportunities for the following year, and thus allow you to identify the key decisions to be made inside engineering and to prepare for these decisions. 

While the executive review of the product road map will focus on the execution part of the road map, it is equally important to lead an innovation review within the engineering team to ensure that you retain your technology leadership against the competition. 

Finally, in order to have an effective yearly review, a lot of work must be done prior to the review (in order to inform the product road map decisions), as well as after it (in order to reflect the new product road map).MORE FOR YOUWill AI Save The Movie Consumer?A CMO’s Road Map To Leading In The Post-Covid Era16 Critical Steps When Updating Your Company’s Marketing Funnel

Before The Product Road Map Review

During the product road map review, the executive team will usually concentrate on customer-facing features and will ask for dates for key deliverables. In order to make this discussion as effective as possible, you need to research what the likely top requests will be. In addition, you need to identify technical debt, as well as noncustomer-facing features (quality, robustness, performance, business continuity, compliance/security) that must be addressed — and build a business case for each of these, along with timing and resource allocations.

Because your development capacity, velocity for paying technical debt back and customer-facing work are determined by the resources available, you need to negotiate your budget for the coming year, parallel to building our future plans. Conversely, making commitments to a product road map without a clear idea of resources available will lead to uncomfortable discussions later.

With a good idea of the major engineering projects in place, you can refresh your technology road map and discuss the new technologies you need to acquire in order to deliver next year — whether this technology is inside the product or part of your internal tools. For example, have there been any significant advances in AI, cloud computing or analytics that will improve your efficiency or increase your competitive differentiation?

Finally, a good retrospective of the team will complete the preparation for the annual review. Based on this year’s accomplishments and next year’s objectives, how does the team need to evolve? How do you need to evolve? Do you need to radically improve quality? Will your market demand a step up in security? Who on the team has delivered beyond expectations? Do you need to take new classes or get a mentor? A thorough retrospective should involve a broad consultation with people inside and outside the engineering team.

During The Product Road Map Review

Product road map review meetings — particularly when part of an executive off-site — are usually intense affairs with lots of passionate discussions (usually a good thing). As CTOs, we must accomplish two critical objectives:

1. Avoid committing to any delivery dates on the spot, unless we have absolute clarity on both requirements and resources availability. However, you must provide estimates of scope for key features to inform decisions on priorities.

2. Ensure that the most important deliverables on the road map have well-documented business cases, from which it will be straightforward to extract precise requirements.

After The Product Road Map Review

Even when the yearly product road map review does not bring major surprises, the aftermath always entails a lot of work, which consists of delivering the actionable product road map and figuring out the changes necessary to execute this road map — beyond writing the code.

An actionable product road map is a commitment from the engineering team to deliver certain features by certain dates. This implies that the budget has been finalized, requirements and resources are clear, and you have done a detailed-enough design and task breakdown to make these commitments with enough confidence and buffer that you will not disappoint your customers. 

In parallel, you must solidify our plans to refresh how you innovate, as well as how you execute. 

On the technical side, you need to complement the customer-facing product road map with your internal technology road map, your technical debt payback plan, and your tools and infrastructure upgrade plans. 

Finally, and too often forgotten, the organization must be refreshed: Team structure, culture, metrics, methodology, communication processes, technical skills and talent all need to be reevaluated with the active contribution of the teams’ leaders. 

This massive effort culminates with extensive communications: The product road map, once it has become actionable, is shared with the business teams inside the company. In addition, when sharing the road map with the engineering team, it is critical to highlight the planned improvements in engineering, which will make this road map realistic, along with associated growth opportunities for each individual. This communication must be well orchestrated through all-hands, team and individual meetings so that every single engineer continues to be motivated, challenged and rewarded by the year ahead. 

Finally, you need to give your team the tools for success, whether building up your direct reports and delegating more, defining new challenges to feed your continued motivation, learning new ways to lead, or implementing new technologies.

It is a lot of work to properly prepare and execute this yearly review. Yet, like most planning exercises, it usually bears fruits from the process itself of thinking about the future. Going into a new year with a well-thought-out and well-communicated actionable product road map provides a guiding path for everyone inside, and outside, the engineering department.

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