What keeps Malta’s CEOs awake at night? – 242 Group Managing Director James Cassar

Behind the boardroom confidence, CEOs are juggling competing demands. So, we asked five of Malta’s business leaders what keeps them up at night. Their candid answers reveal the tensions, trade-offs and frustrations influencing leadership in 2026 – from AI disruption and workforce strain to bureaucracy, cash flow and changing regulations.

Here’s what 242 Group Managing Director James Cassar had to say.

What keeps you awake at night as a CEO in Malta right now?

The main challenge is balancing growth and structure within a group such as ours, ensuring that all the companies are receiving the right level of investment and support. The level of service is ultimately more important than growth alone.

If you could change one thing about Malta’s business environment tomorrow, what would it be?

People’s disregard for payment terms. It has become common to ignore payment terms, particularly in specific markets. This creates cash-flow challenges across almost all industries.

What’s your biggest operational headache right now?

Consolidating different companies within the group so they work more smoothly together. We’ve invested in a system, which is being rolled out in 2026, that will give managers visibility not only of their departments but of others too, helping them identify synergies and opportunities.

What aspect of running a business in Malta has become significantly harder in the past two years?

Human resources. Not because there’s no interest in joining us, but because perceptions of the industry’s requirements often don’t align with reality. The hard work required to thrive in events is frequently overlooked.

Apart from James Cassar, MaltaCEOs.mt also spoke to Harald Roesch (CEO of Melita), Cenk Kahraman (CEO of Finance Incorporated Ltd), Josef Said (CEO of Konnekt), and Alexander Chetcuti (CEO of Lift Services Ltd) on this subject. Watch this space as these interviews will be published in the following days on our website.

This forms part of a feature first published on Malta CEOs 2026, the sister print brand to MaltaCEOs.mt, both owned by Content House.