The 7 Hidden Leadership Challenges That Can Derail Even the Best Leadership Development Programmes
- Jaya kashyap
- 12 hours ago
- 12 min read
At Esendia, our coaching team has worked with 100s of leaders across many different sectors, supporting them on their journey to senior roles. And one fact has become crystal clear: even the most carefully designed leadership development programmes can fail if they don’t address the hidden hurdles that rarely appear in leadership books or competency frameworks.
These are the challenges that often surface only behind closed doors: in coaching sessions or leadership circles. Left unaddressed, they can hinder personal growth and career success.
To bring these challenges to life, we talked to three of our executive coaches: Adam Armstrong, Becky Remington and Karen Wills, to unpack what they observe in their leadership coaching work every day.
In this article, we explore the seven hidden leadership challenges that our wider coaching team hears most frequently and share design tips to help you build programmes that address these issues effectively. Where available, we’ve included additional data points to highlight the scale of the challenge and to help you build a business case for adding some of our recommended elements to your programme.
1. “I’m Too Busy to Think Strategically” - Time as an Asset
The Data
According to a McKinsey study, 80% of executives say they don’t have enough time for strategic thinking, with operational tasks consuming the bulk of their day.
Source
[https://www.mckinsey.com/capabilities/people-and-organizational-performance/our-insights/make-time-for-strategy]
Coaching Insight
This challenge frequently comes up in our coaching conversations, usually expressed with a mix of guilt and frustration. Leaders say, “I’m just too busy to think.” But when we unpack this, it’s rarely about absolute workload. It's about what is filling up the time. We help leaders shift from focusing on roles and responsibilities to asking: “What’s soaking up your time that isn’t in your job spec?”
Our coach Adam calls these distractions time sponges. These are interruptions, unnecessary meetings, emotional labour from team issues, or stepping in to rescue others. These often stem from misplaced accountability. Adam guides leaders to identify the two or three things only they can do. He helps coachees identify the unique contributions where they add value that others cannot add.
Becky adds an important layer: time and energy challenges don’t stop at the office door. She encourages the leaders she works with to identify personal values to help set boundaries and avoid feelings of disconnection at home or burnout.
Karen sees the lack of space for strategic thinking as one of the most persistent challenges facing emerging leaders. She explains. “It’s not that leaders don’t want to think more strategically, it’s that they don’t get the chance.
Programme Design Tip
Add stretch projects to create opportunities for strategic thinking.
In her coaching work, Karen often recommends stretch projects as a practical first step. These are longer-term but tightly scoped initiatives, so they build strategic capability without adding pressure. Particularly for emerging leaders without regular exposure to senior-level conversations, they offer a valuable bridge into more strategic thinking.
2. “It’s Just Quicker If I Do It Myself” – The Letting Go Dilemma
The Data
A Harvard Business Review study found that 50% of managers are deeply uncomfortable with delegation, despite understanding its importance.
Coaching Insight
Delegation challenges are rarely about skill and almost always about mindset. We often hear, “It’s just quicker if I do it myself,” but underneath that is often a deeper story. Adam introduces leaders to the concept of relational dynamics using transactional analysis. He helps them examine whether they are engaging with their teams from an Adult-Adult dynamic (mutual responsibility and respect), or slipping into Parent-Child patterns, where they take on too much and overprotect and disempower their teams unintentionally.
Becky’s coaching often uncovers fear-based assumptions. Leaders may assume their team members will struggle, underperform, or reflect badly on them. But these are projections, not facts. The real shift comes when leaders begin to see delegation not as a risk, but as an opportunity for others to grow, and for themselves to lead with greater headroom. Sometimes the desire to hold on is rooted in care, not control as leaders want to protect their team from pressure. But, as Becky says, without trust, there’s no room for others to step up.
Karen brings in another important angle: managing upwards. Some leaders take on too much not just because they can’t let go downward, but because they feel they must constantly prove themselves to those above. They avoid difficult conversations about bandwidth or boundaries, leading to overcommitment and ultimately quiet resentment. Coaching helps them find the language and courage to address this dynamic directly.
Programme Design Tip
Add 1:1 coaching to help leaders uncover underlying assumptions.
1:1 coaching is a powerful way to help leaders explore the deeper assumptions, fears, and often unconscious relational patterns that shape how they interact with others, be they more senior or more junior. These dynamics can influence behaviour, triggering responses that aren’t always aligned with the leader's intent. Coaching provides a confidential space where both challenge and support enable leaders to unpack these barriers, reflect on how they respond in different situations, and build the courage to ask open questions rather than rely on assumptions. Crucially, it’s also a space where their own thinking can be safely challenged to allow them to test whether long-held beliefs are still serving them or holding them back.
Running a leadership development programme and worried it’s not landing? Talk to us about how to integrate stretch assignments, peer reflection, and executive coaching into your offer.
3. “Am I Even Good Enough for This?” – Navigating Self-Doubt
The Data
Imposter syndrome is experienced by a significant number of people across professions and backgrounds. Research suggests that up to 70% of individuals will experience impostor syndrome at some point in their careers1. These feelings tend to intensify in contexts involving novelty, transition, or intense learning, such as medical training, where 55% of resident physicians exhibit clinical signs of impostor syndrome3. Importantly, impostor syndrome is not a sign of underperformance. In fact, over 30% of high-achieving individuals, those who appear outwardly successful, report feeling like frauds internally5.
Source: See the list at the end of this blog
Coaching Insight
Self-doubt can be a big part of making the transition to senior roles. It doesn’t always wear a visible badge. Many leaders who seem very confident in public admit in coaching sessions that they’re plagued by moments of uncertainty. Adam often works with leaders on the concept that self-doubt is situational, not permanent. It flares up in moments of high stakes, new visibility, or when stepping into unfamiliar territory. Recognising this can be a huge relief because it's not that they lack confidence entirely, but that their confidence is being tested by context.
Karen makes an important distinction between impostor syndrome and general low confidence. She highlights by how social media can feed unrealistic comparisons, and helps leaders understand that impostor thoughts don’t necessarily reflect a lack of skill. Instead, they’re part of the internal narrative that can be reshaped.
Becky often works with leaders to help them understand that self-doubt is part of who we are as humans. So long as we don’t hold on to it and let it shape our reality. Through coaching, leaders practise naming their fears, gently testing their assumptions, and reframing their stories. This creates cognitive and emotional space for growth.
Programme Design Tip
Use peer learning groups to normalise feelings of self-doubt
Becky advocated using peer learning groups or leadership circles to disrupt isolation. When leaders hear others' voices expressing similar doubts, it normalises the experience and fosters collective resilience.
4. “I Know It’s an Issue, But I Haven’t Said Anything” – Avoidance of Difficult Conversations
The Data
Gallup reports that only 27% of employees strongly agree that their manager provides meaningful feedback.
Coaching Insight
Few things derail teams faster than unresolved issues. Yet many leaders avoid difficult conversations, even when they know that change is needed. Becky frequently sees leaders struggle with horizontal power dynamics, such as challenging a peer or managing upwards. Without clear authority, they worry about repercussions.
Adam sees another challenge: leaders often worry they’ll say the wrong thing, especially in situations involving team members' personal challenges or sensitive topics like well-being. The fear of overstepping personal boundaries leads to damaging silence.
Karen further highlights that when it comes to difficult topics like racism, neurodiversity, or bias, many leaders say they don’t feel “qualified” to say anything. But again, silence sends its own message. In her work, she focuses on creating a permission mindset that helps leaders see that saying something is often better than doing nothing, and that not quite getting it rightthe first time around can be learning moments when handled with humility and curiosity.
Programme Design Tip
Provide training with clear techniques and easy-to-apply frameworks to help turn difficult conversations into learning conversations.
Normalise courageous conversations early in the programme. Offer practical training on how to navigate these moments using simple, accessible techniques. Make sure the workshop includes plenty of small group breakouts and space for personal reflection — this helps leaders explore their own discomfort and begin developing language that feels authentic, not aggressive, when addressing sensitive topics. Small group role plays give participants a chance to get comfortable with the techniques and practise them in a safe setting before applying them back at work.
Want to explore how to tackle these hurdles in your organisation?
Book a 1:1 conversation with our HR experts: https://www.esendia.com/contact
5. “But This Isn’t My Strength” – The Challenge of Shifting Identity
The Data: A Center for Creative Leadership study found that 50% of new executives fail within the first 18 months, often due to an inability to shift from operational to strategic leadership.
Coaching Insight
Karen describes how moving into senior roles means leading in areas where the leader no longer has deep expertise, as they did when they ran a team or a business in a space they knew inside out. That shift from knowing the answers to asking the right questions, is a tough identity leap for many leaders. It often takes time to recognise that asking the right questions is a skill in itself and brings real value.
Many leaders have progressed in their careers because of strong technical expertise. They've been the go-to person, the problem-solver, the one with the answers. But now, in a senior role, value is created differently: through setting direction, making decisions in ambiguity, and enabling others to succeed.
Karen explains further that a transition into a more senior role is much more than a change in job title. It also requires a deeper level of reflection. She encourages leaders to ask themselves: What does leadership require at this level? What do stakeholders need from me now? What assumptions about being a ‘good leader’ do I need to let go of? This type of reflection builds self-awareness and helps leaders find clarity in uncertain situations.
Becky adds another layer, career ownership. This identity shift isn’t just about how leaders lead, but how they manage their own development. Too often, leaders wait passively for the next role or promotion, seeing career advancement as something that happens to them. But modern career management demands a proactive strategy. It’s about applying strategic thinking to your own career: spotting gaps, crafting your next move, and not waiting for permission to grow.
Programme Design Tip
Add 1:1 coaching to explore identity and value shifts
This challenge isn’t something that workshops can fix as it’s deeply personal. That’s why 1:1 coaching is so powerful here. It gives leaders the time, space, and support to explore what leadership actually means at their new level and what they might need to let go of to step into it fully.
Just like in Challenge 2 (the delegation dilemma), coaching creates a space where leaders can safely unpack the assumptions they’ve built their success on. This shift can feel uncomfortable at first. Coaching helps leaders make sense of this discomfort. It allows them to examine their personal definitions of “what good leadership looks like” and start to reframe those beliefs.
6. “How Do I Adapt My Style” – Leadership Style Authenticity
The Data
According to Deloitte’s Global Human Capital Trends report, only 20% of organisations believe their leaders are ready to adapt to new challenges.
Coaching Insight
As leaders step into more senior roles, one of the shifts they’re often unprepared for is the range of situations and people they now need to lead. The breadth of their role expands significantly. And that requires adaptability.
Adam often works with leaders who are starting to realise that what made them successful so far won’t serve them in every setting. They ask: “How do I stay true to myself, but also flex enough to meet people where they are?” The fear is that adapting means being inauthentic. Adam focuses on reframing this: it’s not about changing who you are, it’s about expanding your range. You’re still you, but with more gears to shift into depending on the context.
Karen, on the other hand, often sees a related but slightly different struggle: enhancing leadership presence. For some leaders, especially those who are quieter, more reflective, or who’ve been promoted for technical expertise, stepping into more visible spaces feels unnatural. One of the most common themes in her coaching is leaders who say, “I know I should speak up more in those big meetings… but I don’t feel confident.” Karen helps them explore what leadership presence means to them, and how to show up with intention, not just volume.
Ultimately, both challenges are about developing leadership range. Not being a different person in each room, but knowing how to use different parts of yourself, intentionally.
Programme Design Tip
Add 360-degree feedback and leadership diagnostics to help leaders understand the impact of their behaviours.
To help leaders flex their style without losing their sense of self, you need to show them what they can’t always see. That’s where assessments and feedback tools come in.
Becky highlights the importance of diagnostics like simulations and 360-degree feedback. “They help surface the unseen,” she says. “They show leaders where they already thrive, and where they might need to stretch. And when done well, they mirror the real-life complexity and pressures leaders face and not just abstract scenarios.” It’s not about pointing out what’s wrong, it’s about expanding awareness. Leaders often leave with a clearer sense of the situations that bring out their best… and the ones that subtly throw them off balance.
Karen builds on this by emphasising that effective feedback isn’t just about what comes from the top. It’s about creating space for multiple perspectives from peers, from direct reports, even from those they don’t always click with. The goal isn’t to chase some idealised leadership style. It’s to understand their own patterns, what’s working, what’s getting in the way, and how to adapt in a way that still feels real. When leaders receive high-quality feedback, especially through a process that is well-framed and thoughtfully facilitated, they begin to flex their styles.
7. “I Don’t Enjoy Managing People Remotely” – Hybrid Leadership Resistance
The Data
A Microsoft study found that 49% of managers feel they struggle to trust their teams to be productive when working remotely.
Source: [ https://www.microsoft.com/en-us/microsoft-365/blog/2022/09/22/hybrid-work-is-just-work-are-we-doing-it-wrong/]
Coaching Insight
Hybrid working hasn’t created brand new challenges. Instead, it’s just made the existing ones more pronounced.
Adam often sees leaders who enjoy hybrid working when it benefits them: fewer commutes, more autonomy, greater flexibility. But many of those same leaders still say, “I just don’t like managing people this way.” What they mean is that it feels harder to lead with the same presence, the same connection and the same clarity. And without the skills to do it intentionally, many slip into a transactional management style where they focused on tasks, check-ins, and dashboards rather than development, motivation or team culture.
The core skills of leadership haven’t changed. What’s changed is the level of deliberateness required. Empathy, listening clarity, and coaching all matter more in a hybrid setting because the informal cues are missing. Yet, many leaders are promoted into management without ever being trained to manage in this kind of environment. They bring their preferences, their habits, and their assumptions. And without support, those default modes can make leading in hybrid setups feel draining or disconnected.
Hybrid leadership isn't just about managing where people work. It’s about how leaders create trust and belonging, even when the team isn’t in the same room.
Programme Design Tip
Provide manager training
This is where solid and practical manager training is essential. But not just any training as it needs to reflect the realities of hybrid leadership. That means covering the basics like communication rhythms, trust-building, and visibility across distances. But it also means surfacing the deeper challenges we've already explored throughout this blog because hybrid working accentuates every single one of them.
Struggling to delegate? That’s amplified when you can’t see who’s overloaded
Avoiding tough conversations? Easier to do when meetings are scheduled and you don’t see the person for the rest of the day
Not enough strategic space? In back-to-back calls, time disappears entirely
So instead of treating hybrid leadership as a stand-alone issue, build programmes that integrate these themes. Make the connection between working style and leadership identity. Create reflection points on how leading from behind a screen might trigger old habits or fears. Use diagnostics like 360s to highlight blind spots in distributed settings. And offer 1:1 coaching to help leaders personalise what hybrid leadership needs to look like for them and for their teams.
The key is to stop thinking of hybrid as the side-topic and recognise that it is now the context for everything else. Leadership development needs to meet that reality or risk feeling irrelevant.
Final Thoughts: Building Leadership Programmes That Address the Hidden Work
At Esendia, we believe that addressing these seven hidden hurdles is not a “nice to have” but essential. These aren’t side issues. They’re the human challenges that show up in the real world, especially under pressure. And they’re often the very reasons why even well-designed leadership programmes don’t fully land.
That’s why we embed elements like diagnostics and 360 feedback to surface blind spots, coaching to explore mindset and identity shifts, and stretch projects to encourage strategic thinking and behavioural change. We include peer learning groups to normalise self-doubt and promote shared insight. We offer practical manager training designed for the complexity of hybrid teams. And we treat feedback from a broad range of perspectives as a mirror, not a verdict.
If you’re building your next leadership development initiative, here are the questions we think matter most:
Have you created enough space for reflection and strategic pause, not just activity?
Does your leadership programme provide support for the invisible work: mindset shifts, impostor feelings, delegation hesitations?
Are you helping leaders not just lead better, but see themselves differently?
Are you preparing them for the reality of hybrid leadership, where all these challenges become more pronounced?
And are your design choices grounded in the messy, relational nature of real leadership, not just models and frameworks?
Want to Go Deeper?
Watch our 360-degree feedback webinar where we explore how to surface hidden strengths and blind spots in your leaders.
Watch now: www.esendia.com/webinars
Or get in touch to learn how Esendia can support your leadership journey with high-impact, real-world-ready programmes that deliver results.
Data sources:
Clance, P. R., & Imes, S. A. (1978). The Impostor Phenomenon in High-Achieving Women: Dynamics and Therapeutic Intervention. Psychotherapy: Theory, Research & Practice, 15(3), 241–247.
Srisarajivakul, S., et al. (2023). Gender Differences in Imposter Syndrome Among Software Engineers. arXiv preprint, arXiv:2502.07914.
Villwock, J. A., Sobin, L. B., Koester, L. A., & Harris, T. M. (2016). Impostor Syndrome and Burnout Among American Medical Students: A Pilot Study. International Journal of Medical Education, 7, 364–369.
Cokley, K. O., et al. (2017). Impostor Feelings as a Moderator and Mediator of the Relationship Between Perceived Discrimination and Mental Health Among Ethnic Minority College Students. Journal of Counseling Psychology, 64(2), 141–154.
Crawford, S., & Macnamara, A. (2024). Understanding Impostor Syndrome in High Achievers: A Review. British Journal of Psychology, 115(1), 85–101.
Tulshyan, R., & Burey, J.-A. (2021). Stop Telling Women They Have Imposter Syndrome. Harvard Business Review.
