Career Insights: Key Challenges for Leaders

As we are now firmly into 2026, we take time to reflect on the key challenges leaders are likely to face:

Culture

The ‘why’ still remains central to culture. To get the best from employees and other stakeholders (investors, suppliers and customers), communicating why the business exists, its purpose and what it is trying to achieve remains vital. From this point, communicating values and beliefs, establishing tone and method of communication, how people are treated and how the business identifies itself inspires employees to work hard and commit for longer. Other stakeholders feel focused and excited to invest and that they are part of something bigger. This all starts and finishes with leaders.

Working Patterns

This is linked to culture but is also a key part of operational and delivery strategy. Hybrid and remote work can bring challenges around productivity, trust, culture, and inclusion, they also challenge cost-based decisions in respect of technology and infrastructure. Employees and senior management are likely to have different expectations about working patters and location. How this is managed is key to employee retention and customer and client satisfaction.

Technology

AI and technology remains in flux and is an extremely difficult market to navigate. What to use and how to use it effectively is likely to change in the coming years. Short term commitments to technology providers may be key as the market develops, products change and providers consolidate. Asking the right questions of CTOs and product providers, as well as understanding the use case, limits of systems, costs of use and possible termination is vital.

Knowing your customer and client base is also vital in this context, it will be important to remain authentic. Each business is unique and those which lean on AI or other technology too heavily are likely to be judged by their customers and stakeholders if technology takes the soul away from the service or product outcome.

Global and Political Forces

It goes without saying that global and political forces remain in flux and are highly unpredictable, dividing public opinion and culture, but also generating regulatory and compliance uncertainty.

These play out in real time by slowing investment decisions, product development strategies and can create supply chain and trade instability, adding delays and cost.  Investors and are likely to look for leaders who are most likely to navigate these challenges with them.

Leaders must be agile, forward-looking, and politically aware, balancing short-term survival with long-term strategy while maintaining trust with stakeholders.

Leadership in 2026

Leadership in 2026 comes with no shortage of challenges; from navigating culture and hybrid work to leveraging technology responsibly, understanding global forces, and securing the right talent. At Hummingbird, we are committed to connecting organisations with exceptional leaders who can meet these challenges with purpose, agility, and resilience.

If your organisation is looking for leaders who can shape culture, drive innovation, and inspire teams, let’s start the conversation. Likewise, if you are a leader seeking your next challenge, we’d love to hear from you.

Warm Regards, 

Mariken O’Donnell, Founder, Hummingbird Recruitment