Digital transformation is probably the biggest self-imposed change event you’ll ever go through. It’s a hard, high-stakes, high-visibility endeavour in which setbacks are not only possible but likely. McKinsey’s oft-cited 2019 research found that 70% of transformation initiatives fail – they take too long, cost too much or fail to deliver on their promise. But why so many?

As VP of Customer Transformation for Salesforce, I’ve had a front seat for many transformation projects. And while every company and project is different, I’ve seen some common causes of turbulence that are – relatively speaking – easily avoided, as well as some best practices that tend to set businesses on the right path.

In this blog we’re going to take a look at three common digital transformation obstacles (and what you can do to avoid them), as well as some tips to set your digital transformation initiative up for success. Ready? Let’s go.

Unsuccessful initiatives are those that are not delivered on time or budget. When an IT leader or owner is unsatisfied with the return on their digital transformation initiative, it’s usually due to:

1. Unspecific goals: Change is inherently disruptive. You need a solid North Star to help senior leaders galvanise their teams throughout that disruption towards a larger goal. Something specific and clear like “I’d like to fulfil 10% more parcel orders every month” is much more instructive than “we need to update our shipping software”. Specific goals help you make more focused and intentional technology decisions and provide a clearer rationale for change to the business. Benchmarks about where you are and what you want to improve are helpful to prevent regression when challenges arise and guide your team on where to focus time and effort.

2. Uncommitted stakeholders: The more your senior stakeholders understand the rationale of your transformation (i.e. “We're modernising our booking process entirely around the customer”), the more they can shepherd their teams toward the necessary behaviour change they might otherwise resist. Be generous and open with your strategy – share it widely and explain it thoroughly to anyone who wants to hear it. Stakeholders at every level can become evangelists of change in their own right if they understand and feel some ownership over the transformation taking place.

3. Unconfident technical leadership: People, process, technology – those are the three aspects to every digital transformation initiative. Most organisations have a pretty good understanding of how the first two interact. But many unintentionally treat technology in its own silo – something outsourced to subject matter experts rather than integrated as part of a holistic strategy.

In my experience, clearly expressed outcomes, committed and aligned senior executive teams, and the ability to lead technology-driven change are always present in successful digital transformation initiatives.

1. Plan to achieve something: Be clear about what problem you're solving and how you’re going to quantify it. Express those intentions clearly to your stakeholders and everyone involved in carrying out the mission – it will be your North Star during the entire lifecycle of your transformation effort.

2. Earn the full support of your team: Change management is as much about bringing people on board as it is about choosing the right solution. Establish a clear path forward and agree to keep each other on it.

3. Think beyond point solutions: Invest in more integrated, evergreen platforms that are ever-evolving behind the scenes. Where you can, choose technology platforms rather than products that are focused on a particular set of capabilities. That way you can focus on improving their business rather than keeping the lights on.

4. Empower technical leaders and experts: Let them guide you on where skills gaps lie and how they can be closed. Allow them to drive technological change that may be disruptive in the short-term.

5. Focus on your customer: Your customer should be a critical stakeholder in your transformation. Be intentional and explicit about how your initiative will improve their experience – or else don’t be surprised it doesn’t.

Digital transformation initiatives are so complex and multi-faceted it can be hard to diagnose why they slow down or stall. But beneath the complexity there’s often a deceptively simple root cause – misalignment, or a lack of clarity, or an underbaked/under-integrated strategy.

The truth is that every digital transformation is somewhat of a test-and-learn exercise. The best strategy for your business will depend on what your goals are, what processes you’re looking to improve, and how willing your company is to change. With these tips in mind, I hope you’ll be able to adapt to the inevitable roadbumps of transformation more confidently, and keep up momentum towards your vision.