What digital transformation means to me…

Eliot Fineberg
2 min readApr 25, 2018

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Lots of organisations are talking about digital transformation. If you’re looking to hire someone to lead it, or if you’re going in to “transform” an org, I find it useful to ask these questions.

These are the question I ask.

  • These are what I really mean.

What areas do you want to improve and how do you hope “digital and design” can help do that. (being cheaper, faster, clearer?…)

  • Who is currently responsible for those areas? What is missing that needs to appear?

What new areas do you want to move into and what reasons give you confidence in success. (being new, different and interesting…)

  • Who should be responsible for those areas? What would give them a best chance of success?

Given a desire to make savings/profit of £XXm have you got areas where you have a degree of certainty that you can make gains and still improve quality?

  • How are you measuring the quality of service and the potential unforeseen impacts of changes you are making?

How much are you willing to invest/risk to make these changes happen?

  • Budgets? How quickly do you need things to work? Risk appetite?

What HR/restructuring/training/redundancy do you have in mind?

  • The Real Question. Digital Transformation is really a byword for changing the skills your organisation.

How flexible is your Target Operating Model given you want to take an agile approach?

How do you currently measure success from both a financial and a user/citizen/customer satisfaction perspective?

  • What data drives the organisation, is it the right data, is it modelled the appropriate way?

How empowered are your staff to make changes to the services they run based on user/citizen/customer feedback? How does the budgeting and governance work?

  • How open are you to changing the structures in place, how much do you really want a culture change?

What are your most expensive service/technology contracts? When do they come up for review? How are they going? Who is responsible for them?

  • What real things can we start to fix?

What are the current political priorities and how do you see them playing out into your service delivery / the service design of what you do?

  • What is the politics of the situation? How can we deliver on them or navigate them?

When you say “entrepreneurial” what are you specifically hoping to achieve? How would you be measuring that success?

  • Is this Innovation Theatre or some real measurable thing you want to achieve?

What are your most expensive/riskiest services?

  • What keeps the CEO/COO/MD/Minister awake at night?

Consultants, permanent staff and recruiters; anything you think I’ve missed?

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Eliot Fineberg

Writing things down to try and figure things out in public.