For something we talk about all the time and build heavily into every one of Executive Platforms’ ten annual events (with more on the way), I was surprised when I spotted the last time I wrote a blog post specifically about the Digital Revolution was all the way back in the beginning of May, and the last time we got into real ‘How to Get This Right’ content was all the way back in January.

Let me correct that lapse right now.

One of the things I love most about this subject matter is that while everyone’s Digital Transformation Journey is different, they all have the same sorts of landmarks and landscapes. You can speak to someone in the early days of their journey with a good idea of how things are going and what comes next, and you can also have a conversation with a one-time early adopter who can look back with a bemused expression born of hard-won experience at all they have gone through to bring them to where they are today, while still being able to enjoy looking forward to all that is still to come.

No one ever seems to finish Digital Transformation. The companies that have found real success with it are the first to admit that by the time they have realized their initial ambitions, the scope of what they wanted to do has changed, and so has the technology that now makes even loftier goals possible.

I have had the pleasure of interviewing a lot of people about digital transformations. The links in that last sentence are only a small fraction of the conversations I could highlight for you. I thought for this week’s blog post I might gather together some of the questions I make a point of asking. and that the executives I have interviewed tell me they ask of themselves. For everyone reading this whose organization is on its own Digital Transformation Journey, I hope most of these are already familiar ideas to you. If any of them are new, I would encourage you to build them into your own list of questions moving forward.

Let’s get into it, shall we? For the sake of giving this column some structure, who don’t I start by breaking the questions up by their first word.

The Whats

What are we trying to accomplish? That is the big question, isn’t it? It is surprising how many digital transformations struggle for a lack of clarity on something as fundamental as defining a specific and achievable goal. How do you know if you’re making progress or not if you have not defined success ahead of time? Here’s an important follow up:

What makes that our primary objective? Again, a big question that you need an honest and persuasive answer for before you can expect positive outcomes. Most successful digital transformations are about solving a real need within the existing business. Digital transformations imposed from on high because, “Well, our competitors are doing it…” Does not tend to resonate well down onto the teams and people who did not ask for it, do not want it, do not understand it, and see no benefits from it. Without motivation, efforts stall. No one wants to disrupt what they are doing without a good reason. Nobody gets outside their comfort zone without a purpose. What is the challenge you are trying to solve or the opportunity you are trying to realize through digitization? The more specific you can be about this, the more it will move people to make it work.

What is a realistic timeframe to achieve our objective? There are as many right answers to that as there are types of digital transformation journey, and there is a popular line of thinking where Digital Transformations never actually end at all. By the time your company is well-launched into its journey, there will always be something new and more to do. That said, a successful Digital Transformation —be it a small-scale pilot or a holistic digitization of the entire organization and its business ecosystem— is going to have understandable timelines involved, if only so it can course correct and troubleshoot as things either fall behind schedule or move forward based on unexpected rapid progress.

What are we doing on a day-to-day, week-to-week, month-to-month, and year-to-year basis to make steady progress? I love this question, because that is when people really start embracing their Digital Transformation as a journey, and breaking down what they contribute every step along the way, adding up over time. In many of the interviews I mentioned earlier there is some variation of, “How do you eat an elephant? One bite at a time…” Well, this question gets into the details of that, and if you don’t have good answers for the daily, weekly, monthly, and yearly actions you are doing to achieve your goals, you probably have identified why you are not making real progress.

We could ask a lot more Whats, but let’s move on to some ‘Who’ questions.

The Whos

Who is responsible for making this work? Now one popular answer to this is that Digital Transformation is everyone’s responsibility, but most people I talk to about this will admit that when something is everyone’s responsibility, it’s really no one’s responsibility. Yes, leadership has to come from the top, and yes, if the grassroots of an organization have not bought into the change, effective transformation will not happen, but that is not to negate the importance of having a Digital Transformation Champion or Champions, whatever their actual job title may be. Give them the resources and support they need to succeed. Allow them to work with anyone and everyone, winning hearts and minds along the way. Celebrate their successes, and learn from their setbacks. Having the ‘Who’ figured out is a huge part of getting where you want to go.

Who do you work with to make this happen? Again, big question! Almost every Digital Transformation has external partners of one kind or another, and choosing who is the best fit for your organization and its goals is a multi-faceted decision that I would never dream of summarizing in a sentence or two. I will also put it to you that most organizations also want to build up an internal expertise and capability to build, maintain, support, and improve their own digitization efforts over time. Attracting, developing, and retaining the right people internally and externally to support the Digital Transformation Champion(s) is going to be one of the greatest contributions senior leadership can make to their organization’s successful digital transformation.

Other ‘Who’ questions are going to be more specific and less universal. How about we move onto some ‘Where’ questions?

The Wheres

Where Do We Start? Now that is going to depend on a lot of your answers to the Whats and Whos, but in broad strokes most successful Digital Transformations embrace some version of the, ‘Think Big, Start Small, Scale Fast’ model, so choose your starting point with an eye for a pilot project that is easily achievable, readily understandable, and fairly dramatic upon completion. I could have just said start with the low-hanging fruit, but I wanted to be clear it’s not just about finding quick wins, learning from them, and turning around and doing it again somewhere else. You want your pilot project to inspire the people working on it while also serving as an example and ambassador for where the Digital Transformation Journey is going to take you next. Go in primed for success. Make where you start easy and clear for anyone paying attention to follow what is happening, and then be ready to champion a big result as part of the soft skills of change management to get more people on board as you move on to the next thing.

Where Are We Winning, and Where Are We Losing? There is a style of leadership I admire that includes regular and honest conversations among colleagues where you can admit whether you are doing well or doing poorly at something, not to divide people and projects into winners and losers, but to identify what is doing better than expected, what is doing worse than hoped, learn lessons from both instances, and adjust the expectations of one while finding ways to provide additional assistance and support to places that are struggling. While these conversations are good to have in any business and on any topic, they can be vital for Digital Transformations. In the proverb, “Success has a thousand fathers, failure is an orphan,” few orphans are more alone than the digitization effort allowed to wither on the vine because it was decided letting it die a quiet death was easier than trying to fix what was going wrong. Meanwhile, the successes that are not understood and replicated are at best a mixed result. If every success requires a reinvention of the wheel, the Digital Transformation Journey will make very little progress.  

Where Do We Go Next? This needs to be a reoccurring question throughout the Digital Transformation Journey.  Returning to that, ‘Think Big, Start Small, Scale Fast’ mantra, the ‘Scale Fast’ part depends on thinking about next steps even as you take the first steps. When this pilot project proves successful, what is the next logical application? How does that connect to the larger goals of the organization’s digitization efforts? Are we doing it because it’s easy, or because it’s impactful? What preparations need to be in place in terms of people and resources to roll this out with momentum and enthusiasm, rather than needing to start from scratch? Are there opportunities to work in parallel with other efforts elsewhere, working towards a greater whole faster? Thinking about the future in a logical way is a fundamental part of Digital Transformations.

A Few More Questions

We could go through a lot of ‘Whys’ and ‘Whens’ and ‘Hows,’ but this column is already getting fairly long, and I want to make sure we end with some impactful questions that are not lost in a lot of other content that I might include for the sake of being thorough.

Are You Prepared for Surprises and to Go Wherever the Digital Transformation Journey Takes You? As much as goal-setting, preparation, partnerships, planning, and course-correcting are all the difference-makers between digitization efforts that make progress and ones that don’t, it should be acknowledged that no one knows exactly what a successful Digital Transformation is actually going to do for their company in real terms before they start. The technology is changing so fast, and practical applications are being discovered all the time. Organizations trying to get on top of inventory will discover ways to improve quality control. Companies building up compliance capabilities will find automating that kind of data has a thousand other applications they never considered. Freeing people from automatable tasks will allow subject matter experts to do what machines can’t without increasing headcount. What is that going to do to your productivity? All this is to say, things are going to come up as your Digital Transformation Journey matures and you metaphorically start putting real distance behind you. Do not forbid yourself from exploring forks in the road. Be open to the improvisational prompt of, “Yes, and?” As long as you are not failing to achieve your original objectives, there can be a lot of room for more good things to happen.

If nothing goes as you expect, how are you going to handle it? I have avoided referring to the Digital Revolution until now, because I wanted to save the word ‘Revolution’ for when it can be discussed specifically in this context. Revolutions change things —almost always fundamentally and irrevocably— often in ways the revolutionaries did not expect. There is an expression, “Like Saturn, the Revolution devours its children” that harkens back to the French Revolution where some of the earliest and most passionate advocates of change were themselves consumed in the Terror and other repercussions of the changes they had themselves set in motion. Now I am not suggesting anyone is going to face a guillotine for their part in the Fourth Industrial Revolution, but I think it is worth taking a minute to think how fundamentally we are changing the way our businesses and organizations function.

One of the early success of this blog was entitled, “Will Automation Cost Me My Job?” Let me broaden that thought out beyond the personal. What are the chances your company’s Digital Transformation Journey changes not just how it works, but what it does? There are going to be businesses that go into Industry 4.0 modernization efforts and emerge as technology companies instead of what they were before. There are going to be people in your organization who prove so good at making Digitization work, they’ll spend the rest of their lives doing it. There are going to be tasks that would have taken a team of people years to do that will be achieved almost instantaneously by AI and Machine Learning in a way that is going to both scare people, and also redefine what we think is possible and what we should be trying to achieve with our working lives.

If nothing goes as you expect, how are you going to handle it? You can take that negatively, and some people certainly will. You can also see if as an extension and re-emphasis on my previous question: Are you prepared for surprises and to go wherever the Digital Transformation Journey takes you? Because like it or lump it, Pandora’s Box is opened. We are on this ride together, and things are going to change faster than we would believe in ways we may not imagine. Achieve your goals along the way —please do!— but we should also be asking at all times, what are we going to do when the unexpected happens that we did not expect and perhaps would not have wanted before?

The only constant in life is change, and as we all lean into our own Digital Transformation Journeys, it is important to question both where you are going, and what you will do when you get there.

We live in interesting times. Let’s see where life takes us.

Geoff Micks
Head of Content & Research
Executive Platforms

Geoff joined the industry events business as a conference producer in 2010 after four years working in print media. He has researched, planned, organized, run, and contributed to more than a hundred events across North America and Europe for senior leaders, with special emphasis on the energy, mining, manufacturing, maintenance, supply chain, human resources, pharmaceutical, food and beverage, finance, and sustainability sectors. As part of his role as Head of Content & Research, Geoff hosts Executive Platforms’ bluEPrint Podcast series as well as a weekly blog focusing on issues relevant to Executive Platforms’ network of business leaders.

Geoff is the author of five works of historical fiction: Inca, Zulu, Beginning, Middle, and End. The New York Times and National Public Radio have interviewed him about his writing, and he wrote and narrated an animated short for Vice Media that appeared on HBO. He has a BA Honours with High Distinction from the University of Toronto specializing in Journalism with a Double Minor in History and Classical Studies, as well as Diploma in Journalism from Centennial College.