Readiness to digitise: 12 questions to ask first

Laurence Smith offers twelve questions to help pinpoint your organisations point on the vital journey to digital transformation
By: | September 5, 2018

Have you recently been charged by your CEO to make sure your organisation “gets” digital: to drive a “digital transformation” or create an “innovation culture”?

Increasingly I get calls from Chief HR Officers and Chief Learning Officers who are rapidly embarking on this journey of change and looking for guidance.

I am often asked to share the lessons learned of the DBS cultural transformation from “damn bloody slow” to being the “Digital Bank of Singapore” (and in fact the “Best Digital Bank in the World’) over the last few years.

As I talk with the leadership team in each case, I try to assess where they are on their own journey. I know there are various assessment tools from big consulting firms out there, but I’m not aware of something less formal, that you can use as part of a dialogue to get a sense of where they are.

Over a conversation with HRM Asia’s Paul Howell, we came up with this list which pulls together everything I’ve learned, read, seen, and heard over the last few years in advising numerous firms on this journey.

It is not intended as a scientific instrument, but rather to give you insights as to possible gaps and opportunities in your own journey. So it is not a detailed map or GPS, but rather observations from a traveller further down the road…

When the topic of how do you measure readiness for digital transformation came up, these 12 questions flowed out quite naturally, and in this specific order. I would love your thoughts on how useful these may be.*

(*I have deliberately not provided definitions to the above as that is also part of the test. If you don’t know them, you need to learn them. Click here for a fun and free way to do so.)
  1. Does your leadership team have a clear organisational strategy for digital transformation?
  2. Has your CEO systematically invested, over time, in educating the board and their direct reports on digital transformation?
  3. Has your CEO integrated metrics and KPIs around digital transformation into their own scorecard?
  4. Has your CEO cascaded these KPIs to their direct reports?
  5. Does your organisation have a shared language around digital transformation?
  6. Have you trained at least 5% of your organisation in human-centred design, or Lean Startup, or Agile?
  7. Has your CEO set KPIs around the number of customer journeys or experiments to be conducted in the current calendar year?
  8. Has your organisation launched a broad initiative to understand the “digital world” or develop a Digital Mindset, or digital literacy? (“Digital Quotient” is the term favoured by McKinsey)
  9. Has your organisation realigned HR and talent practices, processes, and incentives to enable a culture of appropriate risk-taking and experimentation?
  10. Has your CEO explicitly recognised experiments and the value of the validated lessons gained from them?
  11. Do you have an understanding of what validated learnings are?
  12. Can you explain MVP to someone (no, that does not mean “Most Valuable Player”!)
(*How do you fare against the rest of the HR community? Take the 12 question quiz on SmartUp and check your score!)
I could write a paragraph about best practices and lessons learned on each of the above, but as a quick checklist on the essential elements of digital transformation, I think the above captures that which I have seen to matter most.


Laurence Smith

Laurence Smith



Laurence Smith is the host of HRM Asia’s Digital Mindset forum, and regularly contributes articles on how technology is changing the way workforces, and HR, operate.