Dear Board, what sort of “Agile Transformation” are you really after?

My problem with an “Agile Transformation” as a term, is that it’s not really helpful when trying to talk to people.

OK maybe if I used the definition of an Agile Entity as a thing that continuously adapts and evolves to best take advantage of it’s environment, then an “Agile Transformation”, being pedantic, could represent that first step the Entity takes from it’s Creation State to the first Changed State, with the constraint that the Changed State includes a working mechanism for internally triggered evolution (irrespective of how effective).

However, that’s also an unhelpful definition, as I haven’t seen that interpretation in anyone at C-Level who “buys an Agile Transformation Engagement from a Consultancy Organisation”. And that’s what I wanted to write about here. What I see there is usually something along the lines of “We should be better at our IT Development. Other organisations have used Agile and they seem to be better at IT. Maybe we should get some of that Agile IT to increase our effectiveness”.

Therefore I’m parking that thought, and once I’ve worked out how to clearly articulate what my opinion is on that subject, I’ll link to it here.

In the mean time, this is a list of questions I think are worth knowing the answers to as soon as possible in the life of an “Agile Transformation Engagement”. Or even before one starts.

Agile Organisations have very different cultural styles to hierarchical / bureaucratic / “traditional” (for the defensive clients) organisations. A Transformation Initiative (if such a thing can exist) will be about helping an organisation transform itself culturally into something else, one with more pronounced Agile Characteristics and Traits. I think anything that maintains the cultural status quo (especially if it’s a “negative-in-the-context-of-an-agile-organisation” one) is heading towards the Lip Service end of the adoption scale.

Warning: Some of these questions can be tricky to ask without risking being fired :-). All of these are aimed at either the Sponsor of the Transformation Engagement, or the C-Level Board if it’s broad enough.


Question: Where do you WANT to draw the boundary for the Transformation Initiative?

Question: Where do you HAVE to draw the boundary for the Transformation Initiative?


Question: WHAT do you define as “a Successful Transformation”?

Question: WHY do you think you need “an Agile Transformation”?

Question: Are you “all-in” on this Transformation? What happens if it’s not successful? Do you need a Backup Plan (or Escape Plan)?

Question: If the Transformation results in jobs changing, CAN you update your policy / HR strategy etc to suit? WILL you?

Question: If the transformation results in making some people redundant if they are unable/unwilling to re-train to the target operating model (candidates include middle managers), WILL you make them redundant?

Question: What did you have to do in order to get Board buy-in for the need for “an Agile Transformation”?

Question: When do you “need Demonstrable Results”? Why then? What constitutes “Demonstrable Results”?

Question: Do you have a “Trusted Adviser” to fact-check what you’re being told? If not, what is your level of trust? How can that be increased?


Question: What’s your strategy for sustaining the Transformation Initiative after I’ve left?

Question: What would happen if “after a while” (e.g. a couple of years), your organisation reverted back to the operating model as it stands now? Do you have to prevent that?


Question: How much are you willing to invest? Over what time frame? Is any of that investment conditional on evidence of progress?

Question: Can you tolerate the “Agile Transformation Initiative” as an annual overhead cost to be paid before projects and change budgets are calculated?

Question: Can you tolerate the “Agile Transformation Initiative” as just another project and therefore will need to justify its budget?

Agile Brands

Question: Is there a perception in the “entity-under-consideration” that Brand A/B/C is the right one? Have conferences, articles, experiences etc influenced that perception?

Question: Is there a strategic goal of “Installing” / “Implementing” Brand X? Or is the strategic goal “Adopting” Brand X?

Question: What happens to your Credibility / Authority / Respectability if despite the prevailing “Brand X Bias”, an alternative Brand is Implemented / Adopted?

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