3 Expert Questions to Focus on Winning Digital Transformations

About a year ago, around this time a year, I spoke to a CIO about how to best kickoff digital transformation initiatives. His question, "How do I start? How do I find opportunities that will make a business impact and have the potential to drive transformation?"

I don't recall the specifics of the call and his circumstances but can answer these questions. 

My answers do not depend on whether you are new to the role of CIO or transformation leader. It also doesn't matter whether you are just starting a transformation journey, or, if you're at an inflection point and evaluating the initiative portfolio on where to focus, and what priorities to invest in.

As I said in the opening to Chapter 1 of Driving Digital, 

Look at your company as if it were your first day on the job. What would your first impressions be of how your business is operating?

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2020 Predictions: Agile - Devops - SRE, Low-code, and AI

It's been several years since I blogged on new year predictions. My last one published in 2017 covered blockchain (just getting started), AI (breakthroughs coming), talent gaps (growing challenge), and the importance of social business (even more critical).

In some ways, little has changed in three years, and yet so much has changed. My point is that grandiose predictions make great headlines and are fun to read, but are too ambitious for how fast the majority of industries, companies, and people change.

So last night, I came up with my predictions. These are more insights into how digital transformation has impacted multiple industries and what may happen in 2020.

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John Cusack Practical Quotes on Strong Digital Leadership

Every once and a while, I draw inspiration from movies and actors/actresses. I have a post paying tribute to the great movie. What about Bob? Baby Steps - A Guide to Digital Transformation. I have another post comparing executive meetings with a classic Darth Vadar scene from The Empire Strike's Back. My two personal favorite movie posts are product management advice from the Tom Hanks movie Big and using a great quote from The Hunt for Red October on challenging sacred cows and leaving the past behind.

So, for my last post of 2019, I'm going to share with you some of my favorite quotes from John Cusack and his movies. If you haven't see Better off Dead, Say Anything, or Grosse Pointe Blank, then you're missing some classic places to pull witty bits of wisdom that can be applied in many leadership settings.

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Why it's been a Remarkable Pivotal Year for Digital Leaders

What will you remember about 2019?

I believe 2019 will go down as a pivotal year for how businesses will continue to invest in technology, data, automation, and customer experience. In 2020 and beyond, more companies will look for digital transformation to drive growth opportunities and expand to new markets, while disruption will increase to those that are lagging.

Here are some indicators:

The top fintech news included Fidelitybuying Worldpay, the launch of Apple's credit card, and the controversy over Facebook's Libra cryptocurrency.

The top retail news story was the closing of 9,300+ stores including Payless, Gymboree, Sears, and Walgreens.

Digital health startups have raised well over $10 billion in funding across nearly 1,000 deals over the last two years with many investments targeting the “iron triangle” of health care systems.

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My Top Books 2019: Digital Transformation, Entrepreneurship, AI

One of my 2019 new year resolutions was to read more books. I signed up for GoodReads and stated a reading challenge with a modest goal of finishing twelve books. I finished twenty-four, and many of these books are great reads for entrepreneurs, CIOs, and other digital transformation leaders.

What makes a good book? My favorites have a strong focus, come from a unique perspective, are easy to read/listen, deliver a clear message, back their hypotheses with data or testimonials, tell personal stories, and are concise.

Here are my favorites in three topics: (i) digital transformation leaders, (ii) startup founders and entrepreneurs, and (iii) AI and data.

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Why SMBs Must Consider Upgrading their ERPs to Transform the Business

When your business is small or growing slowly, you can get away with a mix of disparate SaaS tools, spreadsheets, and collaboration over email to manage the business while leaders and employees focus on serving customers.

One of those tools is likely an ERP, financial, or accounting system. The finance person or team is probably using it to manage basic accounting, financial, and business reporting functions. In small and medium businesses, finance is likely operating siloed from the rest of the company.

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StarCIO Report: Digital Survey 2019

Several weeks ago, I wrote the article on CIO.com, 5 outdated technology practices that doom digital transformations where I dated several technology practices and suggested others that were replacing them.

Several weeks later, I opened a poll to selected CIOs, IT leaders, and high potentials to tell me which practices were most outdated in their organizations and what digital practices they were focused on maturing. The results are in and published in the StarCIO Report: Digital Survey 2019.

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