What is keeping leaders awake at night?

What I’ve learned from CEOs and business leaders about their key challenges!

Recent conversations in my consulting work with CEOs and executive teams have revealed a striking consistency in the challenges leaders are facing today. These are not the traditional operational issues that can be solved with process improvements or strategy tweaks; they are deeply human, psychological challenges that weigh heavily on leaders and often leave them feeling frustrated and fatigued.

The challenges are also remarkably consistent for leaders working in diverse industries, including finance, health, retail and government. What I’ve learned from these leaders has inspired me to share the following important insights and tips for leaders and organisations in my upcoming "Leadership Reimagined" series. But first what are these challenges?

Building Collaborative Relationships

Topping the list of leadership challenges is maintaining constructive and collaborative relationships within their teams, their board and key stakeholders. One CEO I have been working with shared how he spent nearly a year building agreement and commitment with his executive team and next-level managers to implement a new line of services for customers, only to learn that a sub-set of his managers were actively impeding progress and two of his executive team members were covertly in conflict with each other. On top of this, increased scrutiny from the board was eroding his once-trusted relationships.

These relationships are not just about getting strategic alignment; they require fostering a culture of psychological safety and shared accountability. The imperative to cultivate these relationships is clear: without them, even the best strategies falter. The CEO added,

“Leaders can’t lead without investing in building strong relationships with their peers, teams and staff. Healthy relationships don’t just happen by themselves.” 

Managing Performance Nuances

The next most critical challenge is performance management. It's not the lack of performance management systems, but the nuanced interpersonal dynamics leaders require to manage performance effectively. A senior executive shared her struggle managing two team leaders with drastically different performance levels and needs. The executive realised her current approach to managing the different performance needs of the two leaders also influenced the underlying conflict between the team leaders. Nearly all the leaders I spoke with mentioned the delicate balance they must maintain between coaching staff growth and ensuring accountability.

Empowering Proactive Leadership

A recurring insight from my discussions with executive leaders is the need for what I call “lead-up” capability among next-level managers. Many CEOs observe their potential future leaders, holding back and waiting for directives rather than taking initiative. When discussing this challenge further with several CEOs, I explored how executive leaders and next level managers could work together as a more aligned organisational leadership group. It was at this point that most CEOs recognised their shared responsibility addressing this challenge at both levels of leadership.

This challenge speaks to a deeper need in leadership development and how we cultivate a culture where leaders at all levels feel empowered to act, innovate, and know when lead and when to follow. 

Navigating Industry Disruption and Changing Customer Expectations

Finally, the rapid evolution of market demands, new technology and industry disruption frequently leaves CEOs feeling isolated in their strategic responses. For instance, a CEO I worked with felt solely responsible for steering the company through turbulent technological changes. It became evident that his leadership team felt ill-equipped to handle such disruptions. Despite attempts by many CEOs to involve and empower their team, they often feel the burden of anticipating and responding to these shifts, with many team members defaulting to “business as usual” strategies.

There is an urgent need for leadership teams to develop strategic capabilities which enable a more distributed leadership approach of agility and responsiveness. This is a challenge not just for leaders but also how they involve their staff.

A Call to Reimagine Leadership

The landscape of leadership is evolving, and so too must our approaches. All the challenges involve leaders having the required interpersonal and intrapersonal capabilities along with a systemic approach for leading complex human dynamics. Each of these challenges isn't just a hurdle but an opportunity to redefine what effective leadership looks like. In my forthcoming "Leadership Reimagined" series, I will delve deeper into evidence-based strategies and real-world approaches that equip leaders to address these pressing issues.

If you are a leader or work with senior leaders, what are the biggest challenges you are seeing? Join the conversation and share your experiences as we delve deeper into redefining leadership for today's demanding business environment.