The do-or-die questions boards should ask about their digital investments


Like me as a board member, how often do you read your board report evaluating your digital initiatives and investments to discover that the project is behind schedule, over budget, the promised enhanced customer experience is not being delivered, and, to cap it all, there is a request for additional investment? Due to some or all of the following issues;

  • sluggish legacy IT systems
  • overspending on new software
  • tenants and staff are resisting the adoption/uptake of the new technologies,
  • upgrades not working.


For housing associations and boards looking to modernise their operations and better serve their residents, digital transformation is a critical step. However, simply investing in new technology is insufficient. According to a recent McKinsey study, even successful transformations yield less than their full potential, with organisations realising only 67% of the maximum financial benefits.

This generally creates a mood of apprehension in the boardroom: will the investment deliver the expected results, will new functionality stand the test of time, how to encourage digital uptake among employees and customers, and what are the risks?

To overcome the fear of failure and unrealised benefits, boards must take a strategic approach to ensure that their investments deliver on their full potential. In this blog, we will provide six pieces of guidance and ten questions that board members should pose to their executives to provide assurance that the benefits of their digital investments are being realised.

Setting Clear Goals and Objectives

Setting a clear vision, goals, and objectives for their digital transformation efforts is a critical step that housing association boards can take. This will help to ensure that all investments are in line with the organisation’s overall vision and mission. If the goal is to improve communication and engagement with residents, for example, the board should invest in tools and platforms that facilitate this, such as a resident portal or mobile app. To help you we have devised a guide on How to create your digital strategy”

Stakeholder Involvement

Involving all stakeholders is another critical step in the digital transformation process. Residents and other partners, in addition to the board and staff, are invited. By soliciting input and feedback from these groups, boards can ensure that their investments meet the needs of all stakeholders. Boards can ensure that their investments meet the needs of all stakeholders and that any issues or concerns are addressed quickly. To learn more, have a read of the latest Mckinsey article on “How effective boards approach technology governance”.


To ensure that their digital transformation investments are being used effectively, housing association boards should also establish metrics to track progress. This can include metrics such as the number of residents using the resident portal, the percentage of maintenance requests submitted through the mobile app, and the number of virtual meetings held. By monitoring these metrics, boards can identify areas where investments are having the most impact and areas where more work is needed.

Train and Support Staff

Digital transformation can alter how employees work, so it is critical that they are properly trained and supported. This includes providing employees with the training and resources they need to use new digital tools and systems effectively. Furthermore, providing ongoing support and resources can assist employees in continuing to improve their skills and knowledge. A housing association, for example, may train staff on how to use a new digital platform and set up a helpdesk to provide ongoing support.

Cyber Security

Establishing a strong cybersecurity framework that can shield the organisation and its residents from online threats is another crucial step. This entails educating employees on how to recognise and stop cyberattacks, putting in place strict password policies, and routinely assessing and updating the company’s security measures. Boards can protect their investments in digital transformation from cyber threats by adopting a proactive approach to cybersecurity.

Latest Trends

Finally, housing association boards must stay current on digital technology trends and developments. This includes attending conferences and networking events, joining sector associations, and subscribing to relevant publications. By staying up to date on the latest developments, boards can identify new opportunities to leverage technology to improve their operations and better serve their residents. To find out more, read our blog on the “10 Key Digital Trends in Social Housing in 2023″.

You’ve probably heard of or used ChatGPT, the natural language-powered chatbot that can have lifelike conversations or generate written text that most people would mistake for human. Similarly, DALL.E-2 has become an internet sensation, astounded by its ability to generate images and illustrations based on words fed to it.

ChatGPT can be used by social housing in a number of ways to improve customer service and streamline operations. Eg, the model can be integrated into the organisation’s website or mobile app to provide 24/7 assistance to tenants, answering frequently asked questions and troubleshooting common issues. ChatGPT can also be used to automate repetitive tasks such as rent collection, maintenance requests, and lease renewals. Additionally, the model can be used to analyse data on tenant satisfaction, identifying areas for improvement and providing insights for decision-making.

Key Questions

Some key questions that board members should ask their executive teams to ensure they realise the full benefits of their digital transformation investments include:

  1. What is our overall digital transformation strategy and how does it align with our overall business objectives?
  2. What specific initiatives are we undertaking that will exceed our customer’s expecations and when can expect a return on investment in our benefits realisation plan?
  3. How are we measuring the progress and success of our digital transformation initiatives and who is accountable for its delivery?
  4. Are we effectively leveraging data and analytics to gain insights and make informed decisions?
  5. How are we managing and mitigating the risks associated with digital transformation, such as cybersecurity and data privacy?
  6. How are we ensuring that our digital initiatives are ethical and compliant with relevant laws and regulations?
  7. How are we engaging and communicating with stakeholders, including customers, employees, and shareholders, about our digital transformation efforts?
  8. How are we building a culture of innovation and continuous improvement to stay ahead of the curve in our sector?
  9. Do we have the capabilities required and how are we addressing the potential impact of digital transformation on our staff, including reskilling and upskilling needs?
  10. Are we effectively managing the costs and resources associated with our digital transformation initiatives, and are we allocating them in the most strategic and optimum way?


By asking these key questions, housing association boards can gain a deeper understanding and provide themselves with some assurance that their digital transformation efforts are achieving their intended goals and benefits.

To summarise, while digital transformation investments can provide numerous benefits to housing associations, boards must take a strategic and holistic approach to ensure that these investments are utilised to their full potential. Housing association boards can help ensure the success of their digital transformation efforts by establishing clear goals and objectives, involving stakeholders, training staff,  tracking progress, implementing robust cybersecurity measures, and staying up to date on the latest trends.

To help you deliver your digital dividend, learn more by downloading our guide to delivering your digital dividend.

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