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Strong Opinions, Loosely Held

· 5 min read
Calvin Cheng

An old friend of mine queried, over hot mocha at a hipster cafe: "So Calvin, what is the most challenging technical skillset or programming language that you think I should master, to grow my tech career?",

I was most tempted to answer - "Haskell", "Erlang", "Rust", "electronics design", "cryptography" or "AI".

But I decided otherwise.

The most challenging technical ability to master is the ability to hold contradictory ideas in your head, remain zen regardless of uncertainties and execute despite a lack of clarity. To be fair, one can argue that this isn't really a technical skill and it sounds a lot more like soft skills.

Hear me out.

Why is this important?

This is a skillset that is relevant to us - even more so if one is a professional engineer - in this world around us dominated by technology. Navigating the noisy, diverse and often chaotic world of business goals, product design and engineering disciplines means that we are perpetually faced with diverse opinions and are compelled by tight deadlines to make clear decisions.

Being able to do so with a strong opinion, and yet be ready with contradictory opinions as backups and executed in parallel, is the 2nd order, high level bit that one needs to flip, in order to be successful as a principal engineer, or a successful executive.

This is one of the attributes (besides many other personalities) that I look for when I hire, or when I choose who I prefer to work with and who I want to work for.

But how? Any Case Studies?

That sounds confusing. Are there case studies we can learn from?

Here's one - Microsoft embracing Linux.

Linux was seen as a threat by Microsoft and declared as a virus that needs to be extinguished and its open source nature was compared to communism. A complete 180 degrees change of mind occurred when Satya Nadella took over as CEO.

To do so, Microsoft needed to overcome its own prejudices, and more significantly, it needed to overcome organisational resistance because financial incentives were aligned for their own in-house software capabilities. Changing behaviours is a monumental challenge and can devolve into endless technical debates with no outcome.

The Microsoft today leverages linux as a profit center as part of its Azure cloud offering and its engineers actively contribute to improving various linux distributions. Even though Azure's cloud offering places it 3rd place in market share behind Amazon's AWS and Google's GCP, it has managed to remain relevant.

Microsoft needs to have a strong opinion that its own Operating System is the best. Windows OS has been their core profit center since its founding. But Microsoft also needs to have a loosely held position about that as the competitive landscape changes.

Market Timing

Could Microsoft have changed its strongly held opinion earlier and be the market leader for cloud services?

Linux is the building block for most of cloud services today, holding more than 90% market share. Windows OS was designed for the desktop and was never really suitable for cloud services for many technical reasons. So in order for Microsoft to succeed in cloud, it really required both business acumen and technical know-how to understand how to leverage Linux instead of treating it like the enemy or dismissing it as a "toy" OS.

At that point in tech history - 2010s - there were a lot of shared server providers and emerging VPS providers like Linode, leveraging the open source license nature of Linux to provide convenient cloud servers.

So as a thought experiment, the important questions we can ask ourselves - with the benefit of hindsight - are

  1. What could Microsoft have done so that Azure embraced linux, become a category leader and innovated before Amazon launched its AWS cloud offering?

  2. How can Microsoft join the dots - that shared servers or Virtual Private Servers leveraging Linux on Virtual Machines will be fundamental to cloud services - when the dots do not appear to be related at that point in time? Before anyone does? At the correct market timing?

  3. How do we think outside the box within the Microsoft organisation? It is not hard to imagine that many executives and principal engineers are believers in their own ecosystem - and have financial incentives to remain so - and are mostly likely to take the "Strong Opinion, Tightly Held" stance.

The Billion Dollar Technical Acumen

Going to the root of the challenge - the challenge would have been to find and appoint leaders who have sharp intuition, who are willing to measure risks, execute on specific business and product experiments and can hold completely contradicting ideas in their head - "Windows is great" and "Linux is ALSO great".

Linux was and is Microsoft Windows' or Windows Server' competitor. But Linux was and is ALSO Windows' complement. Linux is technically appropriate for cloud services, viable precisely because it has no license fees and can be leveraged as such as a cloud offering, i.e. make money on rental of servers, not on license fees. And while Windows is Microsoft's profitable business line, Microsoft as an organization can continue to love and support its loyal Windows customer base.

And this, this ability to have "Strong Opinions, Loosely Held", is the Billion Dollar skill (technical acumen, and yes, soft skill) to deliver success and signal amidst the noise.