The art of conducting a digital transformation

  • Technology installations are getting easier, but with them comes greater transformational challenges.

  • Project managers, often the first to be cut, are uniquely suited to help clear blockages and protect people.

  • Conducting the moving parts of a transformation is necessary to ensure alignment.

A digital transformation is like an orchestra. Stay with me here. It’s a metaphor that works surprisingly well to explain why some transformations get stuck in a cacophony of muddled goals and why others smoothly crescendo into a digitally-enabled, thriving business. 

You might think, when reflecting on your own transformation projects, that everything is going pretty well. Each project unit — much like the orchestral sections, be it brass, strings, percussion — has its lead, perfectly suited to their expertise and following the ‘sheet music’ of your strategic roadmap. 

But transformations fail quite often. Why? One reason is that organisations, eager to attain leaner business models, implement industry software that boasts quick installation. But they make a key mistake: they don’t have a conductor; in this case, the humble, often expendable, project manager.

The complex problem of simplicity

Many organisations’ first foray into digital transformation is software implementation. As technology has become more sophisticated, tailored to industry pathways and floating above us in the cloud, its implementation has become a simpler proposition. In many cases, installing an entire new product suite can be done in just a few mouse clicks.

Without the need for software developers to customise programs, or hardware to be maintained, the difficulty of a technology project seems to disappear. So, if it’s as easy and as quick as some promise, it may be difficult to justify the cost of a project manager. It can seem unwarranted and invite the perception that a senior tech lead can manage it.  

But what is often missed, is that projects, even tech ones, are just as much about people and processes as technology. Businesses invest in technology to enable their organisations to stay compliant, cyber safe, current, agile. Technology enables transformation — but transformation is never just about technology.

When a digital transformation has ground to halt, many businesses find that what they thought was simply a tech implementation, has been unmasked as a hidden transformation. And a transformation takes time and effort to both plan and run. And discipline to manage. 

Direction and tasks need to be set — and tracked. Difficult decisions need to be made and justified with evidence. Expectations need to be managed. Budgets need to be maintained. Timelines need to be met. Employees need to be onboarded, upskilled, brought along on the journey. Blockages cleared. 

All these skills are those held by a professional project manager.

A missing people link

There are as many benefits as skills in project management. The success of a digital transformation very often boils down to one thing: people. No matter how you scope them, transformations are complex and people will always be the trickiest part of them

This is where orchestration is needed. While your individual teams — be they HR, finance, IT — may be going perfectly well, each works in their own specialist field. This is true even when your teams are agile and cross-functional — their speciality will be one part of a puzzle. With no one to let the brass section know that their part of the score is too loud, no one will hear the strings come in. If percussion tempo is just slightly out of sync with woodwind, the overall piece of music will not come together. 

Project managers excel in uncovering these misalignments by utilising the power of the dumb question. Simply by asking “Why?” can get experts, in their effort to explain to the de facto ‘layman’ of the project manager, to question their own assumptions of how things must be done. And in doing that, it can open up the rest of the team to ask linking questions — e.g. if you did things that way, I could then do this. Momentum begins.

Transformations involve moving parts, and more often than not, each part affects another, whether or not it is aware of that fact. The project manager’s questioning gains a unique perspective on where ‘ins and outs’ or individual projects are not going to match up, identifying cross-dependencies and misalignment.

Further, with questions come answers, and project managers are well-placed to listen. When brought into digital transformations that have gone pear-shaped, project managers often find that teams are exhausted. They’re shattered, because they’ve been doing everything in their power to keep the project afloat. With deadlines and KPIs, their world can become myopic — and suddenly anything other than sticking to the plan, even if it’s clearly going in the wrong direction, is just not an option. And they have no one they feel they can tell.

A good project manager can help loosen this perceived bind, helping teams to see the bigger picture, shielding them from outside pressure, providing opportunities to reconsider and assess real versus imagined risk. 

Addressing the project management gap

Whether you have a project manager in your organisation, or want to ensure that you are addressing the skills that a project manager brings, here are some aspects to consider when undergoing a transformation:

  • Ask questions — Not only does it show your interest in how the project is really going, it breaks up entrenched mindsets, gets things moving and can highlight synergies (or misalignments) to pay attention to.

  • Bring the perspective — When down in the details, it can be hard for people to assess risk. Make sure assumptions are correct when it comes to deadlines and directions. 

  • Pay attention to the health of your team — Are people looking tired? Give them a break and a bit of breathing space. It will not only lead to better work, it will also build trust.

  • Trust your instincts — Especially for executives. If all the reports say things are ticking along but something feels off, it probably is.

  • Be prepared to pause — If a project is going wrong, stop. If it’s going down the wrong path, pause and take stock. It will only get infinitely worse if you don’t. 

  • Respect your conductor — If you don’t have a project manager, but instead assign someone to keep things running smoothly, they need to have carved out time to do so. A conductor doesn’t have time to sit down and direct a whole orchestra when they have a day job to do. 


As organisations implement digital solutions to bring efficiencies, boost productivity, streamline processes and explore new business models, it is easy to get swayed by the ‘ease’ of which such things are promised. As anyone who has gone through a digital transformation project can attest, it can take twice as long as you think it will and, because people are involved, be more complex than you imagined. 

Without the visibility that a dedicated project manager brings, or the experience of having gone through such projects before, it can be easy to underestimate the ‘extra’ work that needs to take place around the edges. The mentoring, questioning, people support, hand-holding and reality checking provided by a project manager must not be undervalued.

Whether you hire a professional, or dedicate time to someone’s role, a project manager will prove essential to ensure your project remains on track and that everyone in the orchestra is playing the same tune. That will be music to every CEOs ears.