An example of a CTO's operating year's business plan

I'm continuing my series of posts sharing my work portfolio from my past as a technology executive (CTO) when I was directly responsible for a large engineering team (150+ people excluding partners). I approached this role as the next big challenge in my career aspirations. I gave myself a timebox of 3 years, after that, I'd intended venturing on to something else outside of the video world. I'm grateful for the experience as I left with learning all types of executive-management skills for managing business and technology operations. I also accomplished praiseworthy results in what would seem a short amount of time, in just 3 years. This shows how much intensity and density can be packed into a 3 year work experience. I know I would probably not see that much excitement and high-stakes challenges again for some time, even as I write this post in 2023, five years later, whilst working with Amazon's AWS...

Every CTO/Engineering Leader must write an Operating Plan

If you're a technology executive and you're not owning your very own technology operations business plan, in writing and not through high-level powerpoint slide decks, then you're missing a trick and you're missing out on a powerful asset and artefact, that IMHO, is essential for navigating your technology journey. Even before my time with Amazon, I used to write a lot, despite my employer not being a writing-documents oriented company, especially at executive leadership level. Personally, I needed a way to make sense of things, apply critical thinking and process my thoughts into a credible strategy for executing. I also needed to take my senior managers on my journey, lead by setting an example of thought-leadership through writing (because writing documents was unfamiliar to some managers). I also wanted to reach the software engineers on the floor, doing the day-to-day work, help them see the big picture and grasp how the work they do matters to the end goal. 

Another benefit of sharing your technology strategy in written form is to promote alignment and information sharing across many groups of stakeholders - customers, internal partners and external third-party primary partners. As a CTO for a specific business segment (online video), I had my own company's leaders as my primary stakeholders (CEOs, fellow C-Suite top team peers like Customer Acquisition, Retention, Marketing, Sales, Ops, Product, etc.), I also had to support other business' shared goals. In addition, I was part of a wider group structure of the parent group company, inheriting goals from the Group-CTO, Group-CIO, Group-CDO and Group-CISO domains. So the ever familiar problem of having multiple demands placed on a technology organisation. 

As a leader then, you need a mechanism for alignment on your execution plan for the year - this is usually an organisation's yearly operating plan. The aim is to show how you, as the engineering leader are accounting for all the priority goals you're taking on from your various customers and show how the work you plan to deliver, relates to achieving those goals and objectives. Additionally, the specific technology initiatives that you are taking accountability for yourself (like tech platform modernisation, addressing technical debt, etc.) remain nevertheless important for your org to deliver results and meet stakeholder expectations.

Below is one version of a year plan that I authored and used as a constant reminder for checking in and reflections on progress. Let me know if it helped you :-)

[Disclaimer: I write about my past work experiences, this post dating back to 2017-2020 referring to entities that no long exist today (in 2023). Previous mentions of such entities are widely in the public domain through news media outlets, press briefings, launch announcements, etc. I take time to ensure that nothing I share exposes commercially sensitive material. My intent is to share my learnings and experiences to teach and mentor people on a similar path to me; with the side benefit of showcasing my professional work portfolio to current and future prospective employers & head hunters, through my writing].