How I switched from Program Manager to CTO

During the first quarter of 2017, I was wrapping up a massive digital transformation project "VOD Wars" in its second year of running and nearing completion. A program that I led from inception in the capacity of Chief Program Director (for Multichoice Group) as some classic corporates call this role, Amazon has a similar role called the  Single Threaded Leader (STL). 

I was responsible for co-ordinating multiple programs and workstreams  that cross-cut multiple businesses. Each business had their their own heads of technology, engineering, program & project offices, operations & support functions. Each business also had their their our business goals & KPIs and in addition, had to support group-wide goals (Group-wide goals are akin to Amazon's S-Team goals). Whilst my primary stakeholders were CEOs of the various business units, I had to not only keep my eye on the high level (managing upwards and indirectly influencing across businesses that I had no positional hierarchy at all (as I was doing my own thing as an independent senior management consultant), I also had to stay close to the technical engineering, operations, support, marketing and customer experience details on the ground. The program was a great opportunity for me since I'd always wanted to experience every piece of the Video Entertainment value chain puzzle as much as possible. 

Prior to VOD Wars, I'd further strengthened my exposure to all domains of the media Video Entertainment business, by being the chief program director for launching a new video streaming business "Showmax" to Africa, in 2015. This too, was a wonderful experience, launching a business start-up from zero to launch in under ten months, co-ordinating every business (legal, finance, marketing, strategy), technology (buying a new tech stack, integrating new offshore development team, building & customising product features, integrating payment vendors, 3rd party integrators, etc.) and operations (content workflows, infrastructure & customer support). 

And before Showmax, I'd been leading major group-wide initiatives for advanced and internet-connected devices (I was lead end-to-end program manager for DStv Explora, for a small stint delved with the then nascent DStv Mobile), and before that, spent my time as technical program & product manager for advanced set top box middleware software, NDS Mediahighway/Videoguard platforms.

In fact, the last time I was engineering-focused, strictly speaking was in 2010 - when I'd taken up the role of Principal Engineer after inventing a Speaking TV/EPG - a role change, after being involved in project, program and product management before then. And the years 2011-2013, when I'd helped transform the consumer devices division of Multichoice, to use modern software engineering methods of planning, product development and end-to-end systems integration, in getting them to launch their first version of DStv Explora.

Being a rock-star program manager consultant in a niche industry in Africa, did come with its perks! I billed by the hour, and was mostly in control of my time. I had back then in 2014-2017, experimented with 4-day work-weeks, I took personal time off (PTO) for long periods of time (sometimes 2 months unpaid or more). It was around this time that I had started working on my RAGE model for personal development. As I dived deeper into my professional self-reflections, the following realisations about my aspirations started to really gnaw at me:

• I was getting bored of being a program manager, I felt there was no challenge left and I was no learning anything new any more. I'd been reading, studying, applying and mastering the many forms of project & program management since 2008 and by 2017, I think I'd arrived and was feeling satisfied with my craft, as an expert program manager, a project leader at the top of PM hierarchy as explained here.
• I felt I reached my goals of understanding how to run a full blown video entertainment business as I had experienced by then, every single aspect of business, technology & operations of the Pay-TV value chain.
• I had my program management work mechanics down to an art form: I had a repeatable process, had built templates for structuring program charters, communicating progress, etc. There wasn't much more I could learn from the mechanisms needed in program management and was operating at the highest level of project leadership. A lot came naturally to me, operating on instinct most of the time.
• I felt could run a Project Management Office (PMO) with my eyes closed. I'd started mentoring and coaching other project & program managers but I was not interested in specialising in PMOs.
• I learnt the secrets of engaging and managing high-powered senior executives, I was confident in discussions, meetings, presentations and contractual negotiations.
• I was not sure I could continue being a consultant without having skin-in-the-game, or having a seat-at-the-table. 
• I had failed to land other consulting engagements outside the scope of Video / Media - so my "business" AS3 (Africa Systems & Software Services) was a one-man show, tied to one big corporate without hope of branching out of video - so why remain a consultant when I could have a seat at the table if I wanted to?
• As a consultant, I'd developed my own prime directives of knowing when to offer advice, opinion or put a proposal together. Consultants serve a purpose, they can lead through indirect influence but also need to remain humble and fully aware, that they don't really have any clout or say in strategic decision making. Something, if I'm completely honest with myself, I wanted to influence directly, I wanted my ideas to be heard, I wanted to be directly responsible for change, and influence strategy and change the status quo, if given the chance. I could sit on the sides and offer advice and witness slower pace of change, or get in the ring, get my hands dirty and experience true ownership, accountability and responsibility. I yearned for an opportunity to experience being a senior executive, responsible for a big organisation.
• I felt I'd drifted too far from the technology domain - and needed to get back to the core. After all, I built software myself in the early days, and have degrees in Engineering and a masters in Computer Science. I wanted to get closer to the tech teams building modern apps, internet scale. 
• I wondered if a Program Manager could switch back to being a Technology Leader - looking at people around me in executive roles, I felt I had more than the requisite experience and technical know-how to adapt and do the job.
• I needed to experience what it meant to be a manager with direct responsibility for people and bottom-line P&L. No more assisting from the sides.

With those reflections in mind, I explored new opportunities in the tech space, landing first an Interim CTO/GM (fractional CTO) role, still as a consultant for the first year which then later converted into a permanent role as Head of Technology/CTO for DStv Digital Media, Online Video Platforms, which then later became Multichoice Connected Video. I would spend the next 3.5 years intensely immersed in the role of CTO, learning new skills and soaking the experience all in: VUCA, big organisation of 150+ people, handling large budgets to the tune of R1.5 billion, growing people, making decisions with the seat at the table, navigating and surviving corporate politics and most importantly, getting my hands dirty with technology development again, turning around a distressed platform and reviving an engineering team...I decided to leave again as soon as I felt it was time for another change...however, I'd like to think I'd left the place looking better than I first found it. I'm going to share some of my experiences of this journey as and when I feel inspired to do so, like today. 

Getting to apply for a CTO role was nerve-wrecking at first, even though the job advertised was a General Manager - Technology & Platforms.  I felt like an imposter, full of doubt - classic imposter syndrome. I was vocally self critical so much so that I analysed and critiqued the original role guidelines advertised and provided a deep dive of my self assessment with regards to the role's expectations, benchmarking myself against what I assumed was the high bar for the role. I wanted the hiring manager to be fully aware of who I was, what my experiences were, and what my aspirations were as well before going into the interview. 

Looking back, I was only able to gain this trust based on my previous work as a program manager with a reputation for getting the job done, delivering results by earning trust, that the executives entrusted me with the role. 

One executive who is now the CEO of a large business, once stopped me in the hall-way and said "Mo, I don't know how you do it - but you have a remarkable way of making the complex look so simple!" 

Below is the original self-assessment I shared with the hiring manager for the role. I remain truly grateful to him for the opportunity and trust afforded to me. Here is the doc with my self-assessment. I'm sharing this with you because I believe it could be useful for your own professional review. When applying for a new role, even if it's outside your immediate comfort zone, it helps to take the time to analyse, commenting and rationalising how your present or past experiences can help you delivering in the new role. You don't necessarily have to lay all your cards open to the hiring manager as I did (because I'd already built up the trust relationships over previous years, so people knew me as a program manager but they weren't necessarily aware of my tech background). The prevailing advice you'd find in most career counseling is understand your current reality (be brutally honest about your current reality whilst being positive about your future aspirations) and look for ways your past skills and experiences can speak to the gaps in the role you seek. Every job spec asks for more than what's realistic, so don't give up without at first trying. Every new role comes with an opportunity to learn and acquire new skills, why else does one seek to level up, if not to learn?