Top 4 Lessons from Analysing 65 Digital Transformations

At Salesforce, we have the opportunity to work with thousands of organisations across the globe. We help them transform their business, improve their customer and employee experience, and redefine the way they use technology.

My job at Salesforce Professional Services is to help with the biggest, most complex, and most challenging of these digital transformations. Over the years, I noticed that my customers often came up against the same challenges. So I began tracking these challenges and then worked with other Professional Services experts to track their customers’ transformations.

In the end, 58 Salesforce people collaborated in this research, bringing their experiences in roles such as program and technical architects, success managers, account executives and partners, and agile coaches.

Together, we have tracked 65 transformation programs across the globe so far. In our endeavour, we’ve collected and analysed our customers’ and our teams’ experiences, pain points, lessons learnt, and tactical and strategic takeaways.

In doing so, we have applied one of the most important practices we recommend to our customers: data-driven decision-making.

The result is a database of Salesforce customers’ transformation lessons. And the biggest lesson? Don’t ignore the “soft” human-related challenges, such as aligning different stakeholders. In fact, we found that tackling the soft challenges early had the highest correlation with transformation success, along with four specific lessons.

1. Tech problems are often caused by human-related issues

By aggregating insights from the 65 programs, our database gives us a global view of the enterprise transformation landscape and a clear understanding of the programs’ similarities and differences. It also gives us a tool we can use to quickly identify patterns across specific industries and regions.

Of course, every organisation is unique, and we have come across many different roadblocks to change. However, using our database, we identified 26 common challenges, which were roughly divided in half between soft challenges and “hard” technical issues.

Then, as we dug deeper into our collective experiences, we were able to confirm that soft and hard challenges were often linked. In fact, we found that human-centred issues were the root causes of most technical challenges.

For example, if a technical team is struggling, running late, or over budget with an integration project, it may be because a leadership team underestimated the complexity of the integration when planning the project. Or they didn’t consult the right technical people to begin with. As a result, the technical team may not have had enough time or resources for the project.

Making matters worse, tech problems often surface in the later phases of a transformation, such as during deployment, often delaying the overall program.

We also found this type of challenge was common in programs across all industries and regions, leading us to our next key lesson.

2. Solve foundational soft challenges first

Taking this approach further, we identified foundational soft challenges that should be addressed at the beginning of every significant transformation.

It starts with defining the goals and scope of the program, along with details such as:

• What needs to change and how and when?
• Who needs to have input into those changes?
• Who is accountable for them?

It’s a process that should be done diligently and honestly without overselling the benefits or promising unrealistic outcomes or timelines. Overselling can lead to issues such as underestimating complexity, which in turn can cause the same technical problems, delays, or budget overruns that we described earlier — along with disappointed stakeholders, executives, and potential shareholders.

With the program defined, your organisation can then tackle foundational soft challenges, including:

• Differing assumptions between people and teams
• Underestimating complexity
• Lack of accountability by key stakeholders
• Lack of alignment between teams
• Stakeholder changes

Other soft challenges that need to be addressed early include:

• Loose requirements for projects
• Grey areas of accountability, particularly during handovers
• Too many cooks and a lack of bias for action
• Conflicting parallel programs.

Once these challenges are addressed, your teams will be better able to deal with technical issues in the program’s development, testing, deployment, and go-live phases.

How soft challenges affect hard challenges across transformation phases:

3. Address challenges in large transformations methodically

In our experience, the more ambitious the transformation is, the more important it is to tackle the soft challenges early and in a methodical way.

That’s because as the scale of a transformation increases, so does the program’s complexity and the potential for ambiguity in stakeholders’ assumptions, accountabilities, and expectations.

The program’s scale should not only be measured by the breadth of the transformation across teams, divisions, and regions but also by the depth of the specific issues to be tackled. These may include:

• The number and types of new and legacy systems
• The complexity of IT architecture, integrations, and data models
• The volume of data and amount of technical debt.

Once you have scoped and defined the program, you can address the foundational challenges. Aligning stakeholders is the most important and most difficult to get right. That’s because many different teams will need to be included: IT and business functions, different business units and locations, and participating external stakeholders such as vendors and system integrators.

That doesn’t mean there can’t be healthy tension between stakeholders. For example, it’s important that the service team can give honest feedback to the development team on a self-service app, based on their experience dealing with customers.

Ultimately, teams do have to align to drive the transformation in the right direction. And here, measures such as cross-functional, design-thinking workshops can help get programs off to a good start.

However, you can’t just “set and forget” solutions to soft challenges. The multifaceted nature of today’s transformations and iterative agile development cycles make it vital to continually address soft issues.

The key to ongoing stakeholder alignment is to have a company-wide methodology that enables it. At Salesforce, we use a framework called the V2MOM, which aligns everyone from the CEO down and across every team by defining their vision, values, methods, obstacles, and measures.

Based on these lessons, we have also developed a Strategic Planning engagement to co-create our customers’ vision, goals, and approach to transformations as early as possible.

4. Choose partners that can help you through every phase

Our database also reveals the importance of building a good, balanced team with experienced professionals from the customer, systems integrator, and Salesforce. These teams delivered higher levels of transformation success and overall satisfaction across all stakeholders.

The database is also helping us at Salesforce Professional Services work with various stakeholders to overcome roadblocks. We know, for example, that if a technical team is struggling with hard challenges, it may help to escalate the issues to upper management or executive level, to tackle the underlying soft causes.

Salesforce Professional Services can help customers during every phase of their programs. Not only do we have world-leading technical architects and other specialists, but we also have experts who can help with the strategic side of transformations. We can help clients apply all five aspects of V2MOM, for example, to align their teams.

In particular, we can help identify metrics that allow customers to measure the progress and outcomes of their programs. After all, data-driven decision-making is a best practice that should apply to a transformation as well as everyday operations.

Your next steps

At Salesforce Professional Services, our goal is to align our efforts with the success of our customers’ programs. To this end, our database of customers’ transformation lessons has become a valuable tool. It gives us a clearer understanding of how to help our customers overcome their challenges and achieve success.

We would be delighted to help you with your transformation by providing more insights from our database and tapping into our strategic and technical expertise. But no matter who you work with, I hope these insights from our database help you understand the importance of addressing human-related challenges early.

Reach out to our experts to learn how we can help you succeed.