Having done this (or many parts of) for multiple billion dollar organizations in the retail, mall and loyalty space and having made my fair share of mistakes, my comments on "factors" would be:

1. CEO or COO led or at least owned - digital transformation is business transformation, not technology transformation. If it gets pushed down to CMO/CIO/CTO it can lose its power/urgency and create competing interests inside the company OR could be seen as "killing the sacred cows" of existing revenue generation
2. education, education, education - digital transformation is HUGE, deep and wide...it affects the whole company....it's new business models, new partners, new operating models, new marketplaces. Existing industry leaders haven't been exposed to them as they grew up and need lots of teaching, examples and ROI based backfill to support the investment and feel like they are making the right/smart decisions. i.e. if you've been in the retail business for 30 years, your exposure to "digital business" (not digital technology) has likely been limited as you've been running a retail company
3. Cultural implementation and human capital investment needs understood up front - reeducating ingrained processes/people and "this is how it's done" attitude is the Achilles Heel of the execution of transformation. Eyes wide open that your own people could be one of your largest barriers to success (after #5-7 below)
4. Outside help / empowered consultants - too many busy schedules, competing interests and legacy thinking inside existing walls at multiple levels (even if C-Suite is aligned)...you need a group that knows the game and can be the bad guy, the heavy or can force through some of the initial change to create momentum and be the "agile man in the room" to make stuff happen (see #6). This is especially helpful in creating the ROADMAP as all C-level executives get aligned outside of their core relationship with each other. (I'm obviously biased on this point as a consultant :) ). I will add that those OUTSIDE a company's walls also have much more exposure to tech, data, companies and strategy across multiple industries as it's their core job to know this stuff AND how to leverage it into YOUR industry
5. A vision / strategy....WHY are you doing this? What's the hypotheses that you're working towards / against? How will this transformation create competitive differentiation and growth? What are the new KPIs we will develop and be held accountable to?
6. "Digital" Pilots - fast and quick wins at a tactical level that ladder up to strategy. Creation of corporate agility - usually outside of / standalone from existing systems at the start. If you can't prove it fast, demonstrate ROI and open eyes, you will quickly allow detractors and critics to undermine even the idea of the value of digital transformation which can create a death spiral.
7. Execution - fast migration of pilot wins/learning into new lines of business or new processes. Transition to internal owners. Empowerment of staff, new incentive structures aligned with business + tech needs
8. Tech/Platform framework - How are you going to create a dynamic framework that can consume # 6 and #7 in 30-90 day bursts?
9. Measurement - Accountability....nuff said

Lots more but there's a few gotchas that hav "got me"

RG

I agree with Rob, I would add:

• Look at your competitors and learn from their mistakes.
• Set up what is valuable for your customers, improve their experience
• Adapt digital to the culture of your company
• Use data to create value
• Be flexible, you need to be quick in create new partnerships and adapting to the changing scenarios

Paolo Beffagnotti Thanks , on your thoughts - "Adapt a digital culture" - do you have any insights on this. This is the most common problem with age old enterprises such as Banks, Govt Organizations etc.

Paolo, I like it, but could you lighten up on "Adapt digital to the culture geometry dash breeze of your company" a little?

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