How to cultivate digital leaders in your organisation 

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Follow Peter Verster’s steps for digital transformation success

Over the past decade, we’ve seen a sharp rise in the number of organisations undergoing widespread digital transformation projects to cut costs, gain competitive edge, streamline their operations, or secure their place in an increasingly noise market. 

Getting the ‘frozen middle’ on board enables you to cascade change through the organisation  

However, along with this rise in change implementation, we’ve also seen a significant proportion of these companies run into challenges with their projects that have either resulted in far more modest results than those hoped for, or complete project failure. 

Almost all of the time this has come down to one of two things. Not assigning appropriate funding to the project or, far more commonly, a disconnect between the project plan and the skills, capabilities, and culture of the people required to execute and maintain that plan.  

While there may have been a change in technology, the digital skills, effective leadership, culture change and monitoring haven’t been in place to ensure long-term success. 

Companies with a strong commitment from their leaders (both board level and middle management) see far more success in their digital transformation projects. There are two key problems that need to be solved here: 

  1. Having visible commitment, sponsorship and leadership from the CEO and board.  
  1. Engaging middle management to lead their teams and embed digital principles day-to-day. 

Visible commitment of CEO 

To run successful digital change projects requires a CEO that is supportive, not just in theory, but also in practice. CEOs and board members who check in with project progress at least quarterly and involve themselves in steering and championing the effort consistently see better results than those who delegate the project to a “digital team”.  

It’s crucial that the leader and key executives have a high profile and active role in communicating the importance of the transformation. Senior leaders need to participate in frequent reviews of progress, giving visible support to team members, and they should be seen by the whole business giving regular updates on this progress, with enthusiasm and purpose. 

When the CEO and board members are seen as driving the initiatives, when they are meeting with the transformation team regularly, it underpins the importance of the digital transformation priority. 

Motivate and empower middle management 

Engaging middle management in change projects can be tough – often they don’t buy into the transformation because their goals and incentives are not aligned with the digital transformation efforts. Getting the ‘frozen middle’ on board enables you to cascade change priorities through the rest of the organisation. By not involving them, you risk losing the engagement of the entire front-line workforce.  

To combat this, follow these steps: 

  1. Involve middle managers early in the process, developing the objectives, business cases and approach to transformation, and making these relevant for their team/business area.  
  1. Give them the support, information and tools to cascade the right messaging to their teams and make communication as simple as possible.   
  1. Link their performance objectives to the success of the digital transformation.   
  1. Reward those who become champions of digital progress and give them career-advancing opportunities to be further involved in the projects.  
  1. Provide mentoring and feedback to help them understand the impact of the digital initiatives and empower them to lead change. Purpose motivates people, so ensure they know the purpose and help them buy into the vision.  

Employing high quality digital talent 

Attracting and retaining digital leaders will be a key element of any digital transformation strategy. Creating a diverse team with a good mix of digital expertise and general organisational experience will give you a strong foundation to use as a springboard for ongoing innovation. 

Employee value proposition 

Bringing digital talent into your organisation requires you to have an offer that is attractive for the best talent in a competitive market. This means creating an EVP that the best leaders in the marketplace will buy into. People want purpose and they buy into companies who can authentically communicate what they stand for and demonstrate the value they will create.  

More than that, the chances are the talent you need to attract is passive, which means your brand and proposition needs to be all the more attractive to grab attention. 

Some key things to think about when setting your EVP:  

  • We live in a time where people are more concerned with wellbeing and work-life balance than ever before, so offer flexibility in a range of ways – this could include location, hours, holidays, childcare/parental care packages, wellbeing allowances etc. 
  • People also want to know that they’re contributing to something high quality, so leverage your own industry successes to attract people. 
  • Many are looking for fulfilling and challenging growth opportunities in their career. Giving concrete examples of career progression plans, and guaranteed opportunities for growth, development and promotion can be extremely attractive. 
  • For younger talent, mentoring can help fast-track careers and improve soft skills or experience and insight into management and leadership skills. Offering mentoring with key company leaders is a good way to attract those looking to break into leadership. 

Company culture 

Candidates with a high level of digital and technical ability will have the luxury of taking their pick of the roles. But as mentioned, it’s not just the skills that can cause a transformation to fail. It’s also the company culture.  

That’s why it’s also important to hire for soft skills – which are often far harder to gauge during interviews. They’re also not standard – different soft skills work in different situations and organisations, so it’s very dependent on the culture of the existing team. 

But these soft skills that can cause the trickiest barriers when implementing change projects. Alongside overcoming the existing corporate culture, changing the prevailing mindsets and attitudes within a business is the core challenge for change projects. Having a strategy to develop these soft skills across teams will give any company a competitive advantage that others will struggle to imitate. 

Improving company culture, ready for digital change, requires breaking down silos, increasing effective collaboration, and working in ways that complement and emphasise individual skills.  

Doing this requires a framework that can be adopted quickly, adjusted for team requirements, and can deliver results without stifling innovation and autonomy. 

I have developed a suggested five-step framework for cultivating digital talent that is simple to roll out, and will balance your priorities, timelines, and talent development goals. 

  1. Show your commitment through your resourcing decisions  
    To begin with, clearly communicate that those who perform best and champion digital, will be involved in the digital transformation efforts and be given opportunities to move up the ladder internally. Reward team members who look to increase their digital skillset, go above and beyond to champion digital projects at work, or take the initiative to get to grips with new technologies that support their work or their team. 
  1. Take an open-source approach to finding talent  
    Next, create a detailed assessment of your current team, and highlight where the gaps in skillset are. Create a talent acquisition plan that fills these gaps through redeployment, upskill, hiring or accessing freelance/agency support. Working on your company EVP will make it easier to access great talent quickly. Where needed, bring in external experts and freelance talent to fill or support pivotal roles – especially where more sought-after digital skills are required. 
  1. Ensure effective team composition 
    Look at your team composition. The team needs to be made up of digitally literate people with a range of soft skills, from a wide cross-section of business departments. These people will become advocates, driving new thinking, and embedding new processes in their respective areas. Create personal development plans for individuals with high potential and bring them in to work on exciting projects that will engage them and upskill them. 
  1. Manage talent dynamically to sustain employee engagement and morale 
    As you go, implement visible ways of celebrating success, and manage morale, especially when things get tough. Not every project will be plain sailing, and there will be many barriers to success along the way. Keep spirits high by celebrating wins and moving on fast. Reward those who work hard and do well, and don’t shy away from replacing poor performers.  
  1. Create a talent pipeline 
    Finally, it’s crucial to keep an eye on what talent is needed and when. Digital capabilities are in low supply and high demand. Build a pipeline of talent so that you can fill gaps early. One tactic for this is to be continually upskilling staff across the breadth of the company. Digital skills are not just for teams directly involved in digital transformation – they need to be cascaded throughout. Giving team members opportunities for growth will motivate them to be involved and could highlight hidden gems within your organisation. 


Cultivating digital leaders across your organisation requires dedication and patience from the top. Yes, there are quick wins, but lasting change will come through long-term projects: creating an effective and attractive EVP, engaging talented team members, and creating excitement about digital transformation, setting up processes that reward those who take initiative and champion change.  

There will be bold decisions required to drive commitment. CEOs will need to have the courage to make changes, to push a new vision, and potentially look at changing the leadership. Alongside this, it is critical that leaders demonstrate compassion and care – layoffs, reskilling and redeployment are inevitable. Keeping morale high during a substantial change of process can help smooth the turbulence. 

Peter Verster is author of AI for Business and Founder of Northell Partners 

Peter Verster

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