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? 

Pearls of Umar ibn Al-Khattab (1)

The best way to defeat someone is to beat him at politeness.

Do not grieve over what has passed unless it makes you work harder for what is about to come.

Whosoever shows you your faults is your friend. Those that pay you lip service in praise are your executioners.

I have never regretted my silence, as for my speech I’ve regretted it many times

The less attachment to the world. The easier your life.

-- Umar ibn Al-Khattab

Imam al-Ghazali on Time Management

Your time should not be without any structure, such that you occupy yourself arbitrarily with whatever comes along.

Rather, you must take account of yourself and order your worship during the day and the night, assigning to each period of time an activity that must not be neglected nor replaced by another activity.

By this ordering of time, the blessing in time will show itself. A person who leaves himself without a plan as animals do, not knowing what he is to do at any given moment, will spend most of his time fruitlessly.

Your time is your life, and your life is your capital: by it you make your trade, and by it you will reach the eternal bounties in the proximity of Allah.

Every single breath of yours is a priceless jewel, because it is irreplaceable; once it is gone, there is no return for it.

So do not be like fools who rejoice each day as their wealth increases while their lives decrease. What good is there in wealth that increases while one’s lifespan decreases?

Do not rejoice except in an increase of knowledge or an increase of good works.

Truly they are your two friends who will accompany you in your grave, when your spouse, your wealth, your children, and your friends will remain behind.

-- Imam al-Ghazali

 

2022 Personametry Tracking - Work/Life Balance & Harmony Update

Courtesy

It is time for my yearly ritual of analysing my time spent the previous year. This ritual is one of analysis and reflection, setting up the stage for planning & making new intentions for the upcoming year, 2023! 

I've been doing this exercise consistently over the last eight years! Am I crazy? Maybe?! I've become quite the data junkie, and I'm loving it! 

I know that tracking every activity and accounting for every minute of one's life might seem like overkill to most people. I on the other hand, actually quite enjoy doing so! :-) Primarily because having insights into how I spend my time has really helped me be more conscious and intentional about my aspirations, goals and expectations covering all dimensions of my life, seeking balance and harmony in my personal and professional streams. My methods allow me to focus and maintain discipline with my time...

This is my value system that describes my streams:

Muslim | Individual | Professional (Work) | Husband | Family-Man | Social/Friend

When someone asks me the following: Mo, how's life? Mo, how are you doing work-wise? Mo, how's things? Are you happy? Are you meeting your aspirations? Mo, what consumes most of your time these days? I can have a sincere and authentic conversation about it.

Yes, as some of my friends have argued that you "just know" instinctively where your time is being spent, on what and you just know the areas you need to improve on. Sure, I get that and agree. I find it much more useful to validate my instincts, verify anecdotes with quantifiable data & metrics to help me answer such questions: Where am I spending my time? Am I spending time in the right areas according to my priorities? Am I heading in the right direction? How am I growing? Where am I in my stages of growth across all my personas? How do I measure success? Am I growing holistically as a person?

In 2015, I researched productivity and personal development methods extensively, culminating to me creating my own frameworks:

1. RAGE (Reality Aspirations Goals Expectations). Knowing yourself, i.e. what you stand for, your value system, by identifying Personas. For each Persona, define Aspirations/Goals that becomes your long term personal roadmap. What emerges from this is a scorecard that you can track your progress, see example from 2020.
2. PERSONAMETRY is another concept I created that essentially captures key metrics about yourself, TIME being our most valuable resource. If time is our most valuable resource, do we not owe it to ourselves to account for it? For each Persona you identify with, Personametry is your personal telemetry. It can be extended to a variety of use cases, including overall happiness/stress sentiment analysis. If you're keen to learn more, check out this product specification document I created years ago, but alas, haven't developed the app for it as yet (alas, no time, wasn't a priority!)

Personametry complements RAGE by providing data insights, that I use to analyse if I'm trending in the right direction or not. Keeping a personal RAGE scorecard helps me keep track of how I'm progressing against my personal roadmap. In the last eight years alone, these frameworks have helped me reach my highest potential in climbing up the career ladder (making CTO, executive role), becoming debt free and remaining debt-free for 7 years and-running, improve my marriage enhancing the foundations (insha Allah), and rekindled relationship with family members, including long lost friendships, develop a more consciously confident identity as a Muslim in the workplace, make big bold decisions of starting over in my career (like walking away from CTO and big financial incentives rewards, take a pay-cut and step down in role) or start my own consulting, also make time to focus on paying it forward by offering my time to coach/mentor for free, etc. RAGE/Personametry has also helped me in being critically selective of where/what/whom I spend time with, I've learnt to say "NO" more often guarding my personas and setting boundaries, even with my own family and dearest loved ones.

Emerging from this experience so far are some interesting learning experiences, such as how one's goals and aspirations can change with time, depending on one's stage of life. For instance, where I'm at right now in 2023, is my profession is no longer what drives me (I'm consciously not seeking out the next promotion or level up because I've been there already and experienced the life of an executive), as I'm now seeking new experiences centred on creating more purpose, meaning and fulfilment...Having said this, I remain a pragmatist and so am open to new job opportunities that more closely align with my value system (example: NGOs/NPOs looking for CTO/CIO expertise, Africa-friendly timezone working hours is also being considered). If you know of any opportunities in this area, do get in touch!

Analysing 2022 v 2021 - Data Analysis & Insights

Since 2016 I've tracked 24,983 (±25K) activities as data points, tracking my life streams as: Muslim | Individual | Professional (Work) | Husband | Family-Man | Social/Friend - thus logging 60,572 (±60K) hours with an error tolerance of ±0.5% (99.5% capturing accuracy). In 2022 alone, I logged 8,715 hours, of which: Professional Work consumed 23%,  Personal Life 43% with the physical constraint of Sleeping accounting for 34%. Yep, we sleep for a third of our lives, and I have the data to back that up!

Suffice to say, I've made some good gains in 2022 that I hope to carry through into 2023. Check the slide show for the rest...

P.S. If you'd like to have a coffee/virtual chat about my RAGE/Personametry concepts, or you're curious to learn more, or seeking a mentor/coaching/networking opportunity or you simply want to learn about my workflows, then please get in touch!

You're not so perfect either, consider your failings too

Whenever you take offense at someone's wrongdoing, immediately turn to your own similar failings, such as seeing money as good, or pleasure, or a little fame -- whatever form it takes. By thinking of this, you'll quickly forget your anger, considering also what compels them -- for what else could they do? Or, if you are able, remove their compulsion.

-- Marcus Aurelius, Meditations, 10.30

Remember Socrates's tolerant belief that "no one does wrong on purpose". The clearest proof of that hypothesis? All the times we did wrong without malice or intention. Remember them? The time you were rude because you hadn't slept in two days. The time you acted on bad information. The time you got carried away, forgot, didn't understand. The list goes on and on.

This is why it is so important not to write people off or brand them as enemies. Be as forgiving of them as you are of yourself. Cut them the same slack you would for yourself so that you can continue to work with them and make use of their talents.

* Source: The Daily Stoic by Ryan Holiday and Stephen Hanselman