CIO Connect – CIOs: what keeps you awake at night?

Session Topic: CIOs: what keeps you awake at night?

Is it potential cyber-security hacks, or holding onto your best people, or your relationship with the CEO and Board, or your budget, or lack of progress on your digital transformation initiatives or whatever? In other words, what is your number one challenge and what help are you potentially looking for to help? Conversely, what advice are you prepared to offer to assist your CIO peers with their challenges and what advice would you give to your pre-pandemic self? Finally, what avenues do you leverage to connect with your CIO peers to network on challenges such as these ones?

Discussion Summary:

There was some great discussion and sharing amongst the 2 breakout groups.  Both groups though, were consistent in the top issues that are keeping CIOs awake at night.  The top 2 issues were:

  1. Cybersecurity
  2. Talent Management / Hybrid work

The following were the key discussion points and tips that were shared for each of these topics.


It’s important to raise awareness at all levels of the organization.  With the rising number of breaches and ransomware attacks that have been publicized, concern about cybersecurity has elevated to the Board level.

Some tips to address this were:

  • Use creative ways of communicating and raising the level of security awareness.
  • Build playbooks for responses to breaches and ransomware attacks.
  • Educate yourself to understand the regulatory, governance and compliance issues around security and also to be able to provide guidance to the security team. One CIO took a 3 month online course to get CISSP certification.
  • Bring in 3rd party industry leaders to provide updates and overviews on changing threat landscapes.
  • Develop a security roadmap and keep it constantly updated.

Talent Management:

Recruiting and retaining talent has always been a challenge, but even more so during the pandemic.  The labour market has been broadened with remote work, which has meant more movement of talent.  This has created loss of resources which have been difficult to replace.

Some tips to address this were:

  • Offer flexible work models where possible. Give consideration to keeping functional teams or ‘pods’ together when planning for in-office days.
  • Develop talent. Upskill and reskill to retain talent.  Succession planning and leadership development is more important than ever.
  • Avoid creating a division or ‘classes’ of employees with some working in office and some remotely. There should be equitable treatment and the same experience for all workers in a hybrid work model.

Host:     Gary Davenport
Moderators:      Kyoko Kobayashi and Rita Lazar-Tippe