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Alison Rood


Core skills facilitator | Digital project manager

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Digital transformation: how to help your people navigate through uncharted territory


Digital transformation is not all about technology. It is easy to forget, but a critical element to consider as your company’s tech evolves is how to support your people as you take them along the journey with you...

In 2016 it was predicted that global investment in digital transformation initiatives would  reach $2.2 trillion by 2019. It is therefore timely to discuss the challenges and goals companies should address when planning to deliver digital transformation.

We often focus on the technology element, but according to Andrew Greenway in his book ‘Digital Transformation at Scale: Why the Strategy Is Delivery’, “Digital Transformation is not all about technology; it is about changing the way you work.” 

In my previous article, we looked at the importance of seeking to understand what you are aiming to achieve from your digital transformation, understanding that you are not starting from scratch, as well as managing the change for your organisation, its employees and its customers.

In this article, we will move from discussing your technology to discussing  your greatest resource, your people, providing the steps your organisation can take to upskill a team for digital transformation, while supporting them to navigate the ever-changing landscape. 

Assessing skill sets

It is important to complete an audit of what skills you need to undergo digital transformation, and then gain an understanding of what your team is capable of in relation to the project’s tasks and goals.

Where there is a skills gap you will need to invest in your team to develop their competencies and capabilities. While buying in the resource as and when required is an option, this approach puts your business at risk of constantly needing to outsource work, which is particularly risky where errors are identified.

Bringing in the resource can also change your company culture as they will have a different way of working to those employees who may have been with your business for some time. A blended approach that focuses on developing your staff’s knowledge while complementing them with an external resource as and when required is often the best approach. 

It is important you do not allow yourself to be left behind. You need to understand what skills are required now to complete the transformation, who has them and who could be developed to achieve them. Do some homework and build a general awareness of the technologies within your business and what they deliver now and will deliver in the future. 

Multidisciplinary business

The way technology is moving may require you to create a multidisciplinary business that can bring together teams that can deliver your future objectives. A multidisciplinary team may consist of a product manager, project manager, lead developer, digital designer, user researcher, UX consultant, content editor, Google Analytics specialist, dev ops, front and back developers, and a QA tester.

One of the first challenges with creating a digital transformation delivery team is having to bring people together who have either moved location to join the team or are working across different locations, often in different countries, which can create cultural conflict issues.

Another challenge arises if your team works across different time zones as communication can end up being non-instant, leading to misinterpretation, rather than in real-time where team members can ask questions and obtain the answers they need, preventing confusion and delays. The key to overcoming these challenges are clear communication and well-defined objectives at the outset and throughout. 

Creating such teams can cause a lack of understanding between you and the new team members as well as between the team itself. It can sometimes be difficult to understand new team members who will have vastly different subject matter knowledge to that which you and your team know. They may also have a different way of working and have built a different understanding of company culture.

Merging a new and old workforce can create a culture shock and therefore needs to be carefully managed, otherwise you run the risk of old and new staff being in battle with one another, putting your digital transformation at risk.

Lead with empathy

In these two articles, we’ve looked at how you can start and maintain digital transformation and with this comes challenges for your team.  They are dealing with constant change, having to question the status quo, making changes where things may be perceived to still be working, and identifying an individual’s capabilities to carry out their role now and in the future.

All of this has an obvious impact on the individuals involved and this needs to be managed sensitively and carefully. 

What is important here is to lead with empathy. This starts with creating an environment built on trust and respect, by creating rapport with your team and building relationships with them. This can be greatly enhanced by understanding the individual's skill set, what their key deliverables are, and what pressures they are likely to experience. 

You need to create time and space to actively listen to your team to take a temperature check on how they are. Ask direct questions to avoid having to make assumptions, then carefully measure the response you receive, looking beyond the words being said and tuning yourself in to each individual’s body language. Be present in the moment and focus on the individuals you are communicating with and not other challenges or tasks you have in the back of your mind. 

Think about how each team member takes in information and speak their language, presenting information in multiple ways. This creates a shared understanding across a team who may assimilate information differently from one another.

For example, with the more ‘visual’ members of your team, ensure you are presenting them the information visually e.g. using a Gantt Chart or a wireframe. For auditory people, give them the opportunity to listen to the plans and talk it through with them to help them to make sense of the overall project.

Digital transformation: no easy feat, but essential

When considering your greatest resource – your people – digital transformation creates both challenge and opportunity. It is important to understand that you will be asking your team to venture into new territories and learn new skills, which may make them feel like they are lacking the knowledge and therefore have a weakness.

Added to this you will often need to recruit in new talent which can leave your team feeling left behind or obsolete. Make sure they know you plan on bringing them with you and are willing to invest time and money into their development to future-proof them for the fourth revolution of digital. 

According to Forbes, ‘70% of corporate transformation efforts fail as a result of being unfocused, uninspired and unsuccessful’, therefore, I leave you with two questions to have at the forefront of your mind when considering digital transformation:

  1. How will this technology fit into your existing business?

  2. What problem are you trying to solve, both at the people level and an operational level?


Author Profile Picture
Alison Rood

Core skills facilitator | Digital project manager

Read more from Alison Rood

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