Why are digital transformations so hard (and how can they be easier)?

Digital transformations are not easy at the best of times. If delivering software is unpredictable, expensive and fraught, then digital transformations are that but on steroids. 

You’ve got multiple teams working on multiple products or problems. These entail all the same issues that plague products normally (how do we find the right problem to solve, how do we set the right scope etc) but with a whole bunch of new problems too. 

I’ve worked in 3 digital transformation programmes. Here are a few thoughts on how we can - if not make them easy - at least avoid some common pitfalls.

Get the right, experienced people

No messing about here. You’re trying to completely transform how an organisation works. This is hard work and using people who are inexperienced or don’t have the right experience only makes it harder. 

In all 3 digital transformations I worked in there were issues with resourcing. In one, the organisation redeployed existing staff members into digital roles but didn’t give them any training in how to do those roles. It was tough for them and tough for their teams who needed an experienced pair of hands.

In another, contractors with the right job title were hired but they didn’t have any experience in working in agile, user-centred ways. This led to frustration and conflict and, on one memorable occasion, a team member defending their design and shouting at users, ‘YOU TELL ME HOW TO MAKE IT BETTER THEN’. Ouch. 

These problems aren’t insurmountable, but they slow teams down because before you can deliver anything you need to get on the same page about how you’re going to work. And when you’ve got stakeholders demanding results, that’s rarely a luxury you can afford. 

Personally, I think digital transformation programmes should be weighted towards mid-weight and senior roles, at least at the early stages when you’re still trying to define how to move forward.

Be explicit about how you want them to work

So you’re doing agile. Great. What does that mean then? 

You can’t assume that just because all your people claim to have the right experience they will actually work in the same way. So be crystal clear about your expectations. Should they work in sprints and hold agile meetings? Are they expected to report on risks and dependencies? Should teams be allowed to self-organise and be non-hierarchical? 

In the programmes I worked on, lack of clarity on these points led to problems. For example, teams would agree what they were going to work in a sprint but then senior managers would ask for new tasks to be done at short notice. This threw all the timelines off and created stress. But when the team pushed back nothing changed because there was a soft rule that people with more senior job titles were permitted to pull rank. 

In another example, a team were working on an alpha. Half the team thought that meant coming up with a single solution and validating it worked. The other half thought it meant coming up with multiple solutions and seeing which elements worked or didn’t work and then iterating to create something new. That lack of agreement about what the alpha phase is for created tension that could have been avoided had expectations been set at the start.

This doesn’t mean all teams need to work in the same way. But having that shared understanding in place at the outset means teams have something they can work to - or deviate from for good reason.

Watch the culture like a hawk

Digital transformation programmes are a breeding ground for bad cultures. 

First, this is a programme that is likely going to have a lot of budget and attention thrown at it. So there’s a lot of people sensing opportunities for themselves and trying to cover themselves in glory. More contracts for me! More power for me! So they start to compete. They work against one another instead of together. They try to undermine each other to the top brass. 

And this kind of culture is directly counterproductive to the organisation’s aims being achieved. Digital transformation programmes live and die by the ability of people to put their own ego and interests to one side to work collaboratively.

Second, sexism, racism, classism - all the isms - exist. They exist everywhere, whether as conscious or unconscious bias. And they are deeply corrosive to an organisation’s ability to deliver great work because people do not work in organisations where they have to deal with that shit. If they’re good, they leave and if they’re good, organisations need them. 

In my experience, leadership teams are the key here. No one cares about diversity and inclusion when HR sends out newsletters. People care when the people in charge care. So that means leaders being clear about what the expected behaviours are. 

It means being clear that people will be judged, not only on what they deliver, but on their ability to collaborate well with others and retain good staff. It means being clear that discriminatory behaviours will not be tolerated and putting in place mechanisms for people to highlight them. It means regularly taking a temperature check of how people are feeling in the form of surveys or other tools and acting on the findings.

It’s all worth it.

Digital transformation programmes will never be easy. But they can be easier by hiring or training the right people, being clear about expectations and putting in place mechanisms to encourage a positive working culture. With serious money at stake and serious opportunities for our organisations to be better, it’s worth it. 

Photo by Michael Yuan on Unsplash.