Thriving Through The Transition a.k.a Winning At Digital Transformation

I was tipped off to watching this video by an IT leader in the education sector that I really admire for his approach to IT (high levels of service at the front end and high levels of automation in the back end), so I watched the presentation as soon as I got the chance to sit down and focus on it and take some notes.

Digital Transformation? Everyone is over it aren’t they? It’s cliched already right?

Plenty of people yawn when they hear Digital Transformation yet again, however despite this attitude I gained a lot out of Jeffrey Snover’s presentation and when the Chief Architect for Azure Storage and Cloud Edge, not to mention one of only eleven Tech Fellows in Microsoft, speaks it is generally worth paying attention! So I suggest you spend 30mins to watch but if you prefer to speed read, here’s a summarized version of my notes with some added thoughts and reflections.

Jeffrey’s three key themes were:

  1. Transitions – and the role they play in your career
  2. Transitions – and the role they’ve played in Jeffrey’s own career
  3. Digital Transformation – how this can be the catalyst to supercharge your career

Given the audience of developers he was presenting to, the focus on career impact is understandable, however it was his wider observations of what businesses must do to survive, and then thrive, that were of equal interest to me.

It is through Digital Transformation that disruption can occur and create opportunities to change the linear progression of “stairway jobs” (those that have a steady career progression of step by step improvements) and provide the opportunity to experience “elevator jobs” (periods of time where a career pathway can be accelerated by demonstrating skills that move the company forward).

The idea of positioning yourself (where possible within your existing organisation and role) as someone who is “moving the organisation forward” is neither new or especially insightful, but I find that in regular conversations many people still treat their job as a J.O.B. – something they show up to do in isolation of the wider plans or strategic direction of organisation. Hearing from someone like Snover who has experienced remarkable success in his work career call this out as key so early on in the presentation shows just how important this is.

Industry Transitions Can Hit Organisations Hard


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This is true across the board and I see Education wrestling with the impact of Digital Transformation on a frequent basis, as every area of the educational experience is permeated with technology. As I’ve written about regularly, I don’t see the classroom teacher or university lecturer being replaced any time soon but they should be leveraging technology to assist learning in a multitude of new ways.

Jeffrey referenced his time as a UNIX expert at Digital and later as a Windows NT fan, which created his “elevator job” – the time when he was able to grow significantly in his career. However, when industries started to transition away from vertical integration and towards horizontal integration (ironically, the opposite of what is happening now), Digital did not survive this shift. As Jeffery described it:

They were excellent at doing something that no longer mattered

Within a relatively short period of time the industry changed dramatically and many companies did not adapt.

Do You Want To Be Relevant?

As Digital started the inevitable process of selling off various divisions one by one, Jeffrey moved to Tivoli where he continued to be an expert on NT until one day the CTO posed the hard hitting question to him:

You’re one of the hardest working guys here, you’re super smart, but the issue is the product you work on makes me $15K every time I sell it. I want you working on a product that makes me $2-20 million – so my question is: do you want to be relevant?

In this moment of clarity he realised that his work, whilst valuable, was not moving the company forward and he moved roles as the CTO guided him to.


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This is a really interesting anecdote in leadership as well. How often, or willing, are senior leaders to guide key people in their careers? The better ones do this on a regular basis, even if that may mean potentially losing them from their team or even organisation. The flipside is if you’re seen as a boss or company that promotes talent into greater roles, you’re far more likely to attract new talent in the first place that wants to work for you.

I’ve been in various leadership roles where I’ve thought to myself “Gee, I’d hate to lose that person from my team” but by investing in their professional development and giving them increased responsibilities I’ve generally got more in return from them – although inevitably they moved on to bigger roles as their skills/experience outgrew what could be offered to them.

Doing The “Now” With An Eye On “The Future”

This was perhaps one of the most instructive parts of the presentation, precisely because it is one of the hardest things for anyone to balance. Having moved to Microsoft, Jeffrey could see that the future of computing was going to be very large scale data centres that were going to need high levels of automation and scripting to manage i.e. a Command Line Interface (CLI). He wrote the Monad Manifesto  outlining his vision of using .NET for automation and it was this vision that eventually led to the creation of PowerShell. At this however, Microsoft was fully focused on improving the Graphical User Interface (GUI).

This put him on the outer, requiring a “do now” approach to be combined with a longer vision of what the future was likely to require and the talk includes a few humourous stories such as one exec asking him in frustration “Just what part of Windows do you not f**king understand?” Ultimately, Jeffrey found the way forward by getting a powerful backer and forming a “Coalition of the Willing” which took the form of the Microsoft Exchange Server team who could completely see the value in high levels of automation and had a multi-billion dollar business to back it. It was this level of support that eventually saw .NET and PowerShell added to Windows, but it had taken him five years of his working career.


The key take away for me from this section was finding the right business case or backer to prove the value of your proposition and then form a coalition to drive this forward. An idea you may possess in isolation that is not getting traction may either not be articulated clearly enough for others to understand the value, or may not be as great as you think it is!

Why Software Is Eating The World

Marc Andreesson, software developer and, amongst other things, co-founder of the Netscape web browser said way back in 2011 that software would eat the world by replacing traditional business models with software equivalents. This is not hard to see:

  • Bookstores replaced by Amazon
  • Adverts replaced by Google
  • Music replaced by Spotify, iTune
  • Telecoms replaced by Skype and free VoIP/Chat apps
  • Recruitment replaced by LinkedIn

Even in situations where the physical product remains, often the value add is delivered via software e.g. cars still exist but much of the best differentiation between competitors or models of car is software delivered e.g. safety features, navigation, entertainment, fault reporting etc.

ALL companies need to assume that a software revolution is coming and will hit their industry hard.

The trend above is clear – IT companies are replacing traditional leaders in the market capitalization leader board.  Jeffrey mentioned something that I’ve heard in a few different places now: LinkedIn shows more jobs for developers/programmers are being advertised OUTSIDE the tech sector than inside it. In other words, it’s not the tech sector hiring the most technologists: it’s non-traditional IT companies.

The ramifications for this shift are important for Education providers to understand and process. The need for STEM skills becomes ever more necessary because even if a student has no desire to go and work for a tech company, the chances are that the sector they do want to work in will still require significant levels of technical skill sets. How will the K-12 schooling sector respond to this? It’s happening already to some extent (check these Hacking STEM activities) and at a tertiary level many providers are trying to blend elements of computer science into other more traditional faculties to expose students to skill sets that will allow them to do tasks more efficiently.

This was starkly highlighted to me a few years ago when I was looking for some tutorials on how to programme in Ruby and Python. I found a post-graduate history student was posting a blog on his self-taught journey in these languages for others (like me!) to benefit from. His rationale for learning programming was clear: he could write scripts to scan large volumes of digital text looking for key words, ideas and authors and collate these into a meaningful reading list to follow up with later. There was no way he had the time to read that much manually – programming allowed him to “automate” elements of his research.

The “Other” Moore’s Law: Core vs Context


Credit: Wikipedia

In the last third of the presentation Snover focuses on the work of Geoffrey Moore and his work on Core and Context activities in businesses. Put simply:

  • Core Activities: these differentiate you by adding value to the business that you can charge a premium for, win new customers with and build brand reputation e.g. for Microsoft this is investing in software development.
  • Context Activities: essentially everything else. Whilst important to the running of the business, they are not differentiators e.g. for Microsoft this is receptionists, shuttles to get people to work – basically keeping the business running.

To be a leading business, you need to be investing your time, talent and effort into Core Activities, however naturally over time your competitors will respond, new ones will emerge, substitution will take place, a different angle will emerge in the market and you will no longer be able to charge a premium for the Core Activity like you once could.

Once a Core Activity becomes a Context Activity you must adapt …. and quickly.

I think about the above in terms of the release of major operating system updates. I remember, and it’s not that long ago, that you had to pay for the latest major releases of OS, whether that be Apple’s OS X (now MacOS) or going from Windows XP To Windows 7. Now, MacOS updates for free every 9-12 months and Windows 10 is releasing major updates twice a year – for free! The opportunity for revenue is now elsewhere as consumers expect major updates on a regular cycle and are not always willing to pay for this. Many companies have gone to the digital graveyard to die by not responding correctly or in a timely manner to the challenge of workloads shifting from the Core to the Context.

Snover’s Solution To Succeeding In Digital Transformation:

In the end, the final message for companies looking to succeed in Digital Transformation was in the following two points:

  1. Create Bandwidth:
    1. in simple terms, and perhaps somewhat unsurprising from someone with Snover’s background, his advice was to automate as much as possible and move to smarter solutions such as Software as a Service (SaaS).
    2. Use the cloud, but intelligently e.g. start with a “Lift and Shift” of workloads into Infrastructure as a Service (IaaS) so you’re no longer managing hardware on premise yourself, freeing up time, and then “Lift and Modernise” e.g. use of Containers.
  2. Invest in Innovation:
    1. Re-develop existing solutions to be cloud native e.g. using Platform as a Service (PaaS).
    2. Create as many repeatable processes as possible so you can go to market quickly and innovate your core solution rapidly in response to customer feedback.

By following the above, companies can reduce their IT spend away from “Context Activities” such as purchasing hardware, followed by deploying and managing it, and instead invest in SaaS and automation to create the necessary bandwidth within their organisation to start innovating.

The HEART of Digital Transformation is this: BUILD what differentiates you; BUY what doesn’t

Take Action:

The presentation concluded with the following list of “start doing” and “stop doing” advice, keep in mind the audience was developers:

Clicking Next – in the context of a GUI based environment Automating (scripting and PowerShell!)
Crafting no value add solutions e.g. using Exchange Server on Premise Leveraging SaaS to free up talent e.g. Use  hosted Exchange
Building snowflake servers and clouds DevOps
Low leverage architectures Leveraging Cloud allows you to focus less on the the underlying technology and MORE on the customer conversation
 Dialling it in Invest in your career

Concluding Thoughts:

I personally derived value out of listening to this presentation from Jeffery Snover, someone who has clearly “been there, done that” in his working career and insights on how to marry career progression with organisational relevancy was particularly useful.


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Midway through his presentation he pointed out that many organisations are still yet to engage with Digital Transformation and the likely impact this will have on their business. In my experience, even those that are starting to think about this tend to be at the first or second level of impact or “ripple” for example with the scenario of automated and driver-less cars. When asked what careers are most likely to be impacted by this, people generally list off the obvious: taxi drivers, bus drivers, couriers etc. I would suggest a second “layer” may be the automotive repair industry: driver-less cars are likely to crash less frequently which will significantly impact on the demand for panel beaters. Furthermore, they will be driven with optimum efficiency, so the need to tune and service a vehicle may be reduced.

However, think wider still: a significant percentage of police forces are used for traffic management, speed cameras and drink driving stops. Where there is no driver present, there is no need to police this component, so would you really be encouraging your child into a career in the police with an eye on road safety enforcement?

Education is no different – it will face competing pressures (as well as corresponding opportunities) as Digital Transformation, along with ever increasing levels of software, impact how education is delivered and consumed. There is opportunity to be involved “driving the business forward” and helping add value in this sector for those with an eye to it.

I am always keen to discuss what I've written and hear your ideas so leave a reply here...

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