Digital Transformation, Digital Experience, Digital Thought Leader, Digital Coffee Table, Digital DevOps Team, Digital Dystopia

Some of these things are not like the others.

Have you ever said or heard the phrase ‘digital’ so many times it loses all meaning? Try saying it a hundred times and see if the word still sticks in your brain. If you’re like me, it’ll slide right away like a fried egg off a bald head.

Now imagine baldy over there is your company. It’s risky for a thing to be so pervasive that one cannot escape it, or mentions of it (or articles about it - no the irony is not lost).

The problem is that there is so much work out there, and so many things that could do with a digital transformation (my thoughts on that phrase here:, it can be difficult to find a place to start.

As Laozi stated, a journey of a thousand miles begins with a single step. How do we identify that first step? More importantly, how do we ensure that the thing we’ve identified is in fact, a first step, and not the first mile, the tenth mile or the hundredth mile?

Mark Rosenberg commented on a previous article and stated that based on his experience, while you can educate the entire org on what becoming digital really means, it’s often a challenge to digitally transform a large, classic portfolio. Mark went on to explain that the most important thing to get right when considering what to paint with the digital brush, is defining the outcomes the business wants to see and then aligning use cases.

This paints the picture of a large organization looking at change, as being best served by starting small. By starting with products in verticals relevant to a business’s chosen outcomes, and the teams that look after those products, you provide people with a tangible start and end point, clear boundaries, and the most important thing of all;

Psychological Safety.

No betting the company, no gambling the product, no guessing the market.

Starting without psychological safety can be ruinous for your efforts to change. I’ve previously experienced executives lock up and be unable to make decisions. I’ve seen relationships between colleagues ruined because what is obvious to one incites a fear-based response in another. I’ve seen trusted advisors turn in to detractors that actively try to undermine the effort to change - because they don’t feel safe! For a staff member totally reliant on the company for their living, the prospect of deep upheaval starts ringing alarm bells, and they aren’t bells that can be un-rung easily.

When you come to make the change, be that making digital your default proposition (what does that even mean?) or just applying a digital lens to the way you currently work, you enable staff to participate fully. You empower them to work without worrying about the blowback of a mistake made while learning.

Starting small in this way can also be kinder on your customers. Rather than presenting as a different company overnight, with different offerings or a different business model, we can present a kinder, more thoughtful approach.

Recall when the company that makes your favourite product ‘went digital’ - they turned off the call centre and switched to an online, email only support model, because it’s digital and it’s cheaper. I’m not sure what was more irritating, waiting on hold for half an hour or waiting three days for a job to be done that would normally have taken a five-minute conversation with a human. If you focus your change on the wrong things or are in it for the wrong reasons, your customers will suffer.

Thinking more about selecting that first step though, it feels like you could approach the question from multiple angles. In heeding Mark’s advice from earlier, you need to ensure your company has set those outcomes for you to draw on. Assuming that’s been done,

A Choice appears:

Of these outcomes, which one is the most valuable to our customers?


Of these outcomes, which is the easiest for us to achieve as a first step?

What’s the risk?

Your answer will likely depend on your risk appetite. Personally, working to deliver the most value to customers feels like the best approach. Should you achieve that outcome, you have the best chance of your customer base rewarding you via the bottom line. On the other hand, should this outcome not be achieved or should you not provide a good solution, you’re also much more exposed for the same reason.

Thinking back to when I had to make this choice, my focus and customers weren’t the main revenue stream for the business. This meant that for me in my role, ‘most valuable for Alex’ was not actually the most valuable for the business. It was a weird time on reflection. This meant that I could take on a risk profile that was a bit more aggressive than might fit your context. While it was the most valuable thing for my area, it was actually an easy step for the business to take.

Where risk is a greater concern (or perhaps when you only have one key product that drives company revenue) the safer option is usually to tackle a smaller option. I won’t call them low hanging fruit because, in my experience, low hanging fruit tend to not really exist. They are actually difficult problems masked by a lack of understanding or data.

Instead of creating new teams or new ways of working, or creating new products that need love and investment, begin by conducting user research with a focus on that small problem. Share what you learn, and then act on it.

In the early stages of this work, it’s crucial to share what you’re learning with the rest of the business, and your stakeholders in particular. Once you’ve shown the knowledge you’ve gained, deliver a change to address that knowledge. If you can show that you’re learning from stakeholders, learning from customers and then applying that to your product, you build trust with all of those parties. Importantly, you build that trust in a way that is difficult to argue with. The data tells all.

I chose to look at a particular feature that wasn’t working well in a product. We asked some customers and non-customers to come in for interviews, ended up with a bunch of feedback that we then spoke to the rest of the business about. We had to challenge some folk as the feature had been designed initially based on gut feel. Engaging them as equals from a position of psychological safety meant we had a successful and robust conversation and were able to produce and deliver the product increment.

Snowballs get bigger as they roll

In the same way that you might snowball your debt repayments, snowball the way in which you deliver software. By demonstrating you can deliver in a customer focused way, and by tying that to the results the business might see, it becomes a lot easier to justify larger changes. At the same time, you are building confidence that you can actually deliver that larger change.

None of this requires Agile, Scrum, Kanban or whatever else. It just requires talking to stakeholders, talking to customers and responding to what you learn. If you can design this feedback loop to be short, and become more responsive to the market rather than driven by a project plan, you’ll be in a good place regardless of the chosen framework you want to use.

To me, this is true business agility. There’s no rocket science here, but it does require the things you started out with back in the garage with 8 of your friends, back when the business was young. It requires humility, a willingness to change and grow, and a willingness to get stuck into some problems that may be hard, ambiguous, poorly defined or a combination of those things. This is something that big businesses can lose as they become more process and governance driven (read: risk-averse) with growth.

I mention business agility because there is an implied link between business agility and speed or pace, and pace is something that a successful digital initiative can give your business.

I believe that the hallmark of a digital business is pace. Not technology or software or design. Pace in all things. This is why digital transformations are so lucrative. Providing businesses with the ability to turn on a dime and respond to market forces, legislative changes like GDPR, crises or opportunities. This is why digital is eating the world. This is why it comes up again and again.

Snowballing improvements to your product or chosen outcomes demonstrate pace. This is why we start small or start with one thing. To start big is too risky for the business. It threatens too many people needlessly. It works against the goals of the transformation.


We’re not doing digital for digital’s sake, it’s pace we want. Replacing a paper form with an electronic one doesn’t automatically please your customer. Getting them a response in minutes, not days certainly does though. Amazon is still selling books. The difference is that now you can access a huge variety of books online (more then your local bookstore would have in stock), order online and reasonably expect your order to arrive in a day or two. The days of having to wait for a week are gone. That’s pace. Digital, and the technology behind digital efforts, are simply an enabler. I’m sure that nobody at Amazon will ever regret investing in getting books to customers faster. Likewise, it’s unlikely a business that has tasted pace would regret it, even given the cost.

Getting back to our research, and the action we’ve taken; start small, get the knowledge and deliver that to a user. Even if it’s a limited section of your customers, that’s still good. If you’ve done it once, do it again. Rinse and repeat. As you become more familiar with the process of learning, building and showing, this feedback loop begins to feel natural. It begins to feel better than the way you used to work. It becomes the default to ask customers about their problems and views on your product before starting a bit of work. These lessons begin to show in other parts of the organisation. The organisation begins to think more about pace. More about how they might use technology to increase the pace. This is the turning point. The default position becomes to use digital methods, channels and so on (and the technology behind them) to solve customer problems.

Your digital transformation has begun.

In reality, it’s never as simple as this. Fortunately by keeping your cycle time low and your work chunked as small as possible, the chance of significant problems are reduced, and hopefully the damage any mishap might cause is likewise reduced.

Some points to take away:

Your context and the outcomes you want must guide your efforts.
Keep the psychological safety of your colleagues in mind.
Make sure that the work you do is aligned with the wider business.
Focus on the smallest thing, build trust and then tackle bigger problems.
Build with customers, not just with customers in mind.