What Keeps Leaders Awake at Night?

The headlines

A range of themes came up, such as economic and market uncertainty, regulatory changes, and technological challenges — of which some were beyond their control. There were also a number of common themes that cut across industries. Whether these views were held by functional leaders or business leaders, the themes fell broadly into three categories:

1. Organisational performance – ensuring they are effective as leaders at keeping the organisation focused and enabling efficient and effective performance.
2. Talent retention and succession planning – proactively keeping high performers, correctly identifying successors and keeping them motivated to stay in the organisation.
3. Leadership culture – leaders who have avoided difficult conversations are doing work their direct reports should be doing. Hence, they are reducing the time they spend on added-value work.

Did we find the key to a better night’s sleep?

Yes and No! Whilst many aspects of these themes are completely outside of leaders’ control, we know from our work as executive coaches that some people are more comfortable navigating ambiguity and able to think in more agile ways.  Where many leaders worry and procrastinate, effective leaders will proactively influence those factors beyond their direct control. This is an ability our clients often ask us to assess for and it is something that can be developed.

What Keeps Leaders Awake – the key themes

Most leaders we spoke with were being kept awake by one or more of the following areas:

1. Talent Management and Leadership Challenges – A recurring concern is whether the organisation has the right people in place, retaining talent, and whether leaders are providing adequate direction. A few leaders expressed concerns about succession planning, leadership behaviours, and the ability of executives to take ownership of the future.  This includes issues like leadership development, delegation, and empowering teams.
2. Performance and Productivity Concerns – Many leaders worry about their organisation’s performance, particularly in terms of achieving targets and balancing performance with other priorities such as wellbeing. This includes concerns about how to raise performance standards without harming company culture, as well as the challenge of maintaining high productivity during times of significant organisational or external change.
3. External Market and Economic Pressures – Several leaders mentioned concerns about external market conditions, including economic uncertainty, customer behaviour shifts, and legislative changes that could significantly affect revenue or operations. Specific examples include challenges related to the cost-of-living crisis, competitive pressures, or regulatory headwinds.
4. Cultural Shifts and Organisational Change – Leaders are grappling with maintaining or transforming company culture in the face of rapid change or evolving employee expectations. There is a balance to be struck between keeping the positive elements of a collaborative and psychologically safe environment while driving for higher performance. Culture-related challenges were frequently linked to leadership behaviours and role modelling.
5. Workload, Prioritisation and Resource Management – A number of leaders expressed concerns about workload pressures and the difficulty of prioritising amidst competing demands. This includes managing large-scale projects, navigating through digital transformation, and balancing immediate business demands with future investments.
6. Health, Safety and Wellbeing – Issues related to wellbeing, mental health, and maintaining work-life balance also appeared as concerns, especially in relation to managing stress, psychological safety, and the broader impact of workplace pressures on mental health.
7. Strategic Direction and Long-Term Planning – Several leaders are concerned about aligning the organisation’s strategic direction with future growth plans, including whether they are prepared to manage long-term investments and the potential impact of disruptive forces such as AI or market consolidation.
8. Financial Pressures and Sustainability – Financial strain, whether due to high overheads, underperforming areas, or the need to balance profitability with investment, came up as a recurring challenge. Leaders are worried about finding the right balance between cost-cutting and maintaining business growth.
9. Technology and Digital Transformation – Some leaders are struggling with the long timelines and higher costs of digital transformation projects, as well as the need to ensure they can meet the evolving digital demands of their businesses while keeping stakeholders patient.

These themes reflect the multifaceted challenges that modern leaders face, ranging from managing colleagues and performance management to external economic pressures and the complexities of leading through change.