My first 100 days as CTO: Resetting the Mental Model

[Disclaimer: I write about my past work experiences, dating back to 2017 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 rather showcase my work portfolio to current and future prospective employers, through my writing].

In my previous post, I shared how I switched from being a high level Business, Technology & Operations Program Director to a General Manager of Technology & Platforms (fractional CTO) - and disclosed my feelings of imposter syndrome at the time.

Looking back, this role helped me immerse myself fully into the fast-moving-pace of "immediate get done now, everything is important" culture, ambiguous and uncertain, competitive, make-a-plan do-it-yourself courage, sheer multitude of technology options, rapid development at internet-speed -- not that I wasn't familiar with the domain before -- but this time, I was in the trenches, with full responsibility to turn the ship around and make something a success. Previously, as a management consultant, I would advise and highlight risks, I would coach and help the business put together some plans - and then coordinate the delivery. But I wasn't accountable for delivery as consultant. I wasn't responsible for people management. I wasn't responsible if the platform crashed and get paged 2am. I had no skin-in-the-game...this time, it was totally different. I had skin-in-the-game - which meant that I was leaving the world of consulting behind, back in the trenches, leading from the front as well as guiding from behind, and at times digging the trenches myself. 

What I'd accomplished in the 3.5 years was largely positive on many fronts with more upsides than downsides - but it wasn't all hits! - there were some big misses too. (A future post will share my hits and misses). But in the end, after my time-box was over, despite embattled with some scars of hard graft, I left the world of TV/Video behind, knowing that I'd met my aspirations...handing over the baton to a very capable 2IC that would end up lifting the team even further.

The Situation - VUCA !

I joined the company at a time of massive change and uncertainty. The group company embarked on a complete overhaul of its business and organisational design across the board. Typical with most corporates in Africa, the company contracted one of the big consulting houses to lead the transformation program. Their intention to create a new operating model that would better set them up for the future, i.e. "future fit the business". As a result of this new operating model, entire businesses were remodelled, some businesses reducing roles (job cuts), whilst new lines of business set up for the future (new roles to be advertised & fulfilled). Some businesses were also merged and thus resulting "duplication" were optimised for efficiency. This FutureFit program started slowly and would run for 18-24 months, with its orbit soon to approach my business unit later that year. 

So joining in May 2017, knowing there's upcoming organisational changes, already started my engagement on uncertain, unsteady ground. So as a result of this uncertainty, I decided to transition first as a contractor (Interim fractional CTO consultant) to wait-and-see what happens with the new business operating model designs; and if/when an opportunity presented itself for a permanent role, then apply. 

At the time, I joined the digital business "DStv Digital Media" (DDM) had already been through change, having merged Mobile & Online businesses into one, focused on Digital Media. The product portfolio was expansive covering 55+ countries in Africa, servicing 5 commercial entities in the areas of: web sites hosting, content management, voting applications, sports app, video streaming apps, set-top-box applications, etc. Servicing these product portfolios was a single technology team, which I was responsible for. The role in itself was ambiguous and sensitive, as I had to take over from the previous leader who decided to hang around as an individual contributor focused on innovation.

Despite the uncertainty and impending changes that could come by FutureFit program, my teams still had to get on and deliver. Our business customers were increasingly losing trust in the engineering's team ability to maintain commitments to timelines - almost every project or product release was late. Further, the end customers weren't enjoying great levels of customer experiences as the platform was unstable. Almost every weekend there were outages, that took long times to recover - sometimes customers issues and outages over weekends would only be looked at the next Monday. The state of the technical platform drove many of the business stakeholder and my product customers to insist on the engineering team improve to becoming "world class".

Their partners (other technology teams within the group) also didn't enjoy the best relationships with this new team I was joining. Lack of trust, failed commitments and constant tug-of-war on systems ownership and capabilities - a clash of the traditional structured "IT" versus the modern, fast, scrappy digital tech pirates. There was always tension, most of it being unhealthy.

The state of my engineering team in terms of morale, motivation and appreciation - was not in the best health either. As a result of the constant pressure from customers and stakeholders, late deliveries, being pulled in multiple directions, having to support multiple projects simultaneously with limited resources, not having enough budget for adequate tooling and infrastructure - being on the receiving end of loud, upset customers...I'd inherited a team in distress. Futurefit was also looming, people had seen their friends leave the company as redundancies (layoffs) were made public. It was just a "matter of time" that the restructure find its way to them. So, yeah, fair dose of volatility there. Add to that, their leader was replaced by someone renown for hardcore program delivery - what did this guy know about tech, and why should they trust him when they still had access to their previous leader?

The outgoing leader was still attending the management meetings, contributing to strategy discussions. I had to tread carefully because the work I need to do, demanded calling out all the problems & issues in a respectable manner. The respected the the principle of "respect what came before", but it was still an awkward interaction to be in, sharing my ideas for getting the engineering team in shape and on the road to being "world class" with their ex-leader in the room.

A further sensitive issue was one of my direct reports, a senior software manager openly challenged me for the position - and was extremely unhappy that I was given the role (as they were allegedly promised the role as being next in line). Not a good way to earn trust on the first week on the job! So I seriously had to earn trust upwards (customers, stakeholders), downwards (directs) and sideways (peers & partners) as well.

Added to this was a level of complexity of the system in the way that newly created DDM business co-existed with a few commercial entities as well as how the technology division (my group), interacted with the wider enterprise technology group body. Engineering platforms for multiple products to run in 55+ countries, with each country having its own unique custom features as well as priorities for differentiating markets - all supported by a small scrappy team with a shoestring budget, adds a different spin to complexity.

With all this, I was still excited to take this challenge on. The experience was going to stretch me initially, take me out of my comfort zone. I entered the role knowing the known unknowns, was fully aware of what I needed to do. 

I was in for quite the ride! My opportunity to turn the ship around...

My 100 day plan

My first 100 days had to demonstrate: 1\ A bias for action to address the burning technical issues; 2\ Earn trust of my customers, stakeholders and people by pitching a credible technology plan in place; 3\ Deliver results that showed positive progress; 4\ Influence Futurefit program with new ideas influencing positive changes whilst protecting the team to focus on delivery.

Here's my morning papers (journal entries) setting out my 100 day thoughts:

Fri 11-May: Morning Paper

This DDM role is seemingly chaotic, need to find a balance and a way of prioritising and managing my work in progress. I can't be working every day long hours, need to find the balance and time for my other interests. Officially my days start from Monday, of which I will enter a countdown from 90 days! I must set myself something to achieve in the first 90 days.

First stab: By the end of 90 days, we should have:
- settled with product management on a common backlog that drives the work
- delivered at least one release of DStv Now
- kicked off a stream and have a concrete plan of action for a Platform SDK API
- have a realistic plan for the platforms improvements
- agreed on roles and responsibilities between the various customers and my teams

Within the first 30 days, I need to:
- workshops with product & planning team
- complete handover with R (1st week of june)
- complete a 360 review based on feedback from DDM & External customers
- complete view of all the people in the division
- a full view of people by skills, competency and career aspirations
- a view of the vision and strategy for the group - Why do we exist, What are our outputs, how we go about it?
- agree reporting from all lines - Architecture / Dev / Platforms
- set clear objectives on delivery
- agree a way of working/transitioning VOD Wars program

Within the second 30 days:
- town hall with full tech team
- objectives, pds, measurements of performance clearly defined and agreed by all

Within the third 30 days:
- publish approved strategy & objectives
- must have delivered some feature increment
- reporting & dashboards in place
- improved working relationships with customers
- platform network optimisation plan executing in full swing
- vod wars program transitioned out

Tuesday, 2 May 2017

Ideas for DDM-GM role

Here's some topics to note if you take the GM role:

• Workshop retrospective - aim is to get people to understand the current reality. Timeline of company showing where they started, turning points and current period
• Map out worlds of interaction of teams - micro and macro worlds. Showing customer relationships and where DDM teams fit within this world.
• Talk through the trust curve and get people to vote into areas of the curve. Where do they think they sit? Need to draw quadrant map.
• Talk about RAGE model. Do a workshop mapping out current reality, aspirations, goals n expectations.
• For each line manager, draw a job card mapped to rage, split by work worlds (DDM, VET, customers, etc.) career and personal categories. For each apply the RAGE model
• Self Assessment. Create survey based on Agile Good Ugly book. Get leaders to rate themselves according to criteria of systems engineering practices.
• Workshop with team to define what "world class" means
• Develop vision and mission for group. Tie back to company objectives. The Why golden circle. Why, How, What. Why does DDM exists? How do we behave to reach the Why? What actions or results to we produce that speaks to the Why?
• Get to know everyone. Radical candor. Review CV, skills and experience. Growth/Performance matrix - who are the rockstars? Who are the superstars? Who likes stability? Who wants to grow fast?
• Discuss the Cynefin model.
• Teach the Dreyfus model.
• Team self-assessment down to each last person (identify gaps, growth, training, etc.)
• Career Ladder - does DDM have one?
• Build authentic relationships
• Build trust from outset
• Do not dictate - listen, embrace collaboration & welcome criticism
• Implement Personal Kanban - time management - teach it?

My first All Hands / Townhall - Reset Mental Model of 150+ People

Despite the uncertainty with the group business redesign, our business unit, DDM still had to deliver the years goals. As the financial year runs from April to March, I joined at the start of the fiscal year, a new division where I had to put together the plans for the year, strategy and guide an organisation through turbulent waters. My first All-Hands was meant to set the major scene for the transformation the teams were about to embark on, with me as their leader. On the day of the event, I was somewhat nervous but confident at the same time. Having worked through the leadership and consulted with them on my ideas, this was going to be the first time I'd be addressing the full group, engineers who I've not had any skip-levels with, not having the time to meet everyone since from Day One, I was immersed in operating, putting fires out. Looking back now, I feel I could have done a few things differently (future post).

Below is the slide deck I used for the All Hands. It was an in-person session, in the campus Auditorium that seated 200 people. I'd previously addressed larger crowds before at the same venue in my big program kick-off sessions. This was my first All-Hands to not only my engineering team but I also extended the invite to core partners (product management) and my manager as well.

My aim was to reset the team's mental model, helping them understand our purpose, where we fit into the system and how I see us transitioning, reminding them on our goals for the year - and finally busting some myths from corridor talks.

More Flux thrown into the mix for fun

Just as I was getting into a rhythm after publishing my yearly operating plan in the All-Hands, around September, 4 months into the stabilisation journey, the parent group company announced a big change to its business structure, creating a brand new business unit altogether, called "Connected Video" which found find DDM and Showmax coming together...this merger brought its own share of angst, anxiety and nervousness into the engineering teams - as now there were essentially two technology platforms providing video streaming capability to largely the same set of customers. The subsequent few months to Q4 of 2017, was me experiencing additional turbulence in the sea of change and flux of making career-changing decisions, contending with people (peers and directs) seeking to lead and emerge as the CTO for the new business. More posts on that later.

Did I deliver on my 90 day plan then?

Yes. Check it out... Whilst my engineering teams were deemed "stable" for the next two quarters at least, I was focused on working the bigger picture: Unbundling the tech stack, removing non-core services not related to video stream (website support, ISP-support, voting apps, sports apps), working with partners on new commercials, and designing for the future Connected Video technology organisational design, even though I was still a contractor and had no control, nor influence, of what the CEOs in the decision-making-seats would eventually decide.

A neat tool to bridge the gap between Product & Engineering: Combined Backlog

I came across this picture as I was browsing my consulting data archives. In one of my engagements, there was growing tension and trust issues between product and engineering teams. This is not unusual when these disciplines sit across different lines of business, or do not fall under a single leader. Often there is not enough transparency and sharing, or not enough mutual cooperation going on. 

Engineering/IT generally are not great at sharing the true nature of their technical challenges, architectural issues or simply, the state of technical debt. Even if there isn't much technical debt, engineering leaders and CTOs are responsible for owning a technology roadmap, usually the platform strategy roadmap which creates enough runway for future innovation. The situation is that the work needed to service both the Technology as well as the Product roadmaps, usually needs to be done by the same group of people - "same resources" - running into capacity conflicts, that drives escalation problems. Focus too much on technical streams, you starve the business / product / customer delivery. Focus on too much product features, you run the risk of crippling the technology stack through lack of innovation, foundational architecture thus creating too much technical debt. Healthy tension should exist - but - hope is not a good strategy. More often than not, introducing a simple mechanism of co-operative planning is a good way of building trust through disciplined execution.

As way to bridge this gap, a common solution is to meet half-way, creating a single backlog that combines both Product & Technical backlog items into a single shared Combined Master Backlog. Along with this, create simple mechanisms for managing the backlog with a regular cadence, and as a team, agree on some common terminology, e.g. understanding the status of a backlog item. 

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