Thursday 23 March 2023

Sense making, apples v oranges, finding a path forward from multiple options by asking searching questions

I've been writing about my experiences as technology executive when I was placed in the midst of uncertainty and high ambiguity that impacted both my personal and professional aspirations in a big way. Making the decision to leave my experiment into boutique management consulting behind, after building a solid reputation as a high-level program manager, switching to a deeply technology role into a business unit that was going through disruption due to both external and internal forces -- was not an easy, straightforward transition to make. I experienced classic imposter syndrome (see this post). Nevertheless, looking back now, more than five years on, those experiences helped shape me to becoming more well-rounded, what some would call a diverse Business, Technology and Operations (BTO) executive - or - as Amazon calls it, a Strong General Athlete (SGA).

My writing this month is on communication methods, mechanisms and tools: 
  • How should CTOs (engineering leaders / technology executives) communicate to all groups of stakeholders?
  • What tools of writing and visualisations to use?
  • How to use critical thinking and the art of reflection to deep dive on the technology strategy - calling out the good, the bad and the ugly?
  • How to dive deep to sense make by asking searching questions, that force upwards stakeholder management to engage in guiding the teams on strategy?
  • How to find a common ground and build bridges between two (perceived) competing technology organisations?

Questions & Answers Tree - Seeking Clarity from Executives

Let's recap the situation:

In 2017, I took on the role of CTO for an online video streaming technology platform. The business unit was part of a traditional satellite PayTV company, that created an online companion application to supplement its existing TV subscribers to watch TV on the go, initially through web & mobile applications ("Delta" platform) - by investing in digital media division. Not long after this value added service was created, about two years later, the parent investment company, started up a new video streaming business ("Sierra" platform borne in the cloud, no attachments to traditional PayTV like Netflix), completely independent from the existing PayTV business. The two businesses hardly interacted or shared common product, marketing or technology elements for the first two years. When I joined in 2017, there was talk about potential synergies and closer partnerships - which directed my three year turnaround strategy - to modernise Delta closing the gap on Sierra, thus creating comparable modern video consumer experience (Netflix was the bar). A year later, additional complexity and uncertainty came in when the parent investment company, decided to unbundle its independent video businesses to allow itself to focus solely on e-commerce ventures. What happened? Naturally, Sierra business was folded into Delta - create a new business with two product & engineering organisations running in parallel: 2 CPOs, 2 CTOs - tasked to figure out what the future world could look like in creating a Delta 2.0 strategy.

As part of the interactions, still being the management consultant (at the time, I was regarded as independent without any affiliations to taking any sides - since I worked with all businesses before and had existing relationships with all), I helped the executives tackle their options.

The first one - let's understand the assumptions and questions that challenge assumptions. Can executives be clear about their end game? What is the vision? Why are you so caught up about the apparent duplication in tech platforms?

Here's the tree:

Comparing Apples to Oranges: The decision table view

When two engineering teams are challenged about their platforms doing essentially the same thing, especially when the ask comes from non-technical executives, very often engineering leaders become defensive and say "Ah, you can't compare apples with oranges, you must compare apples with apples". Whilst this might be technically accurate, this is not the way to manage communications with stakeholders. Part of technology leader's job is to simplify technical and product capabilities, meeting your customer and stakeholder needs, where they're at. Even if you feel a visual oversimplifies, you still need to tell a story, like the one I used to gain approval that cemented Delta 2.0 roadmap:


Who knew that four years later, I would be digging out the same mechanisms to help AWS executives, (in my first month barely completed onboarding by the way) to decide on a technology stack that my engineering team would need to build/deploy/operate - for providing calls / chats support as their technical call centre platform, servicing one of their highly-regulated, strictly controlled, private cloud partitions? See below decision table, similar oranges to apples story:


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