Leadership development is often approved with the best of intentions. Founders and senior leaders want stronger managers, better decision making, and teams that can operate more independently. A budget is set aside, a reputable training provider is chosen, and high potential managers are enrolled in programs that promise to make them more strategic, more inspiring, and more effective. On paper, it looks like a responsible, even visionary, investment in the future of the company. In reality, many organizations discover that the outcomes do not match the ambition. Months after the program ends, the same bottlenecks keep showing up. Escalations still land on the founder's desk. Difficult conversations are still avoided. Projects stall because no one feels truly accountable. The slide decks from the workshop sit untouched in a shared folder, and the organization returns to business as usual. At that point, leadership development stops behaving like an investment and starts behaving like a costly mistake.
This gap between intention and impact rarely comes from poor content. Most leadership programs offer solid frameworks on coaching, communication, decision making, and performance management. The facilitators are usually experienced and engaging. Participants often enjoy the sessions and leave feeling energised. The deeper problem is that these programs are often layered on top of systems that were never designed to absorb what is being taught. The training is imported, but the underlying operating model remains unchanged. Many leadership development efforts begin not from clarity about internal needs, but from comparison. A founder hears that a peer has launched a manager program and worries about falling behind. A board member suggests that it is time to "professionalise" the leadership bench. The organization goes shopping for an off the shelf curriculum, hoping that what worked elsewhere will work here too. The result is a copied playbook that is not tailored to the company's specific structure, culture, or stage of growth. When the organisation itself does not have clear answers to questions like "Who owns which decisions" or "How is authority meant to be distributed," even the best leadership frameworks have nowhere to land. Managers return to roles where responsibilities are fuzzy, escalation paths are informal, and decision rights are ambiguous. They might now know different models for coaching or conflict resolution, but they are still working in a system that quietly discourages them from using those skills.
Underneath this misalignment are several recurring design mistakes. One is the tendency to treat leadership as a personal trait rather than a role specific responsibility. People are told to "step up" or "act like leaders," but there is no concrete map of what leadership actually looks like at different levels. A senior engineer hears that they are expected to lead, but no one clarifies whether that means owning long term technical direction, mentoring juniors, or stabilising cross functional projects. Training then remains abstract because the job itself is undefined. Another mistake is retaining the founder or CEO as the ultimate problem solver for everything that matters. Even after training, managers know that serious issues will eventually be escalated upwards. If a client is angry, a project is delayed, or a team member is struggling, they wait for the top leader to intervene. No program can turn managers into real leaders while the organisation continues to signal that authority is concentrated in one individual at the top.
A third issue is the lack of reinforcing routines. Participants may learn how to hold effective one to one meetings, deliver constructive feedback, or facilitate decision making conversations, but their calendars do not change when they return to work. Weekly meetings remain dominated by status updates instead of coaching. Performance is discussed only during formal review cycles instead of being addressed in real time. Without recurring structures that create room for new behaviours, the ideas from training dissolve into good intentions. The visible cost of these misaligned efforts is the price of the program. For early or growth stage companies, this can be a significant line item. But the invisible costs are usually bigger. There is the opportunity cost of time, because every hour your managers spend in a training room is an hour they are not solving real operational issues. That trade off is worthwhile only if the program makes them meaningfully more capable of leading. When nothing about the system changes, the time commitment becomes a drag on delivery without a corresponding gain in performance.
There is also a cost to trust. Employees quickly spot the gap between what is preached and what is practiced. When they attend development programs filled with language about empowerment, ownership, and psychological safety, yet return to a culture where decisions remain opaque and difficult feedback is avoided, they learn a quiet lesson about what really matters. Over time, this gap can breed cynicism, especially among those high potential leaders who entered the program genuinely hoping to grow. Beyond that sits a strategic cost. Leadership development is one of the key levers for preparing an organisation to scale. If that lever is pulled in the wrong way, the company ends up with managers who appear developed on paper but are not truly equipped to carry more weight. You might have certificates, sophisticated frameworks, and polished language, but still suffer from role confusion, founder dependency, and fragile decision making under pressure.
Before committing to further training, it is worth asking some hard questions about the current system. If you disappeared for two weeks, what exactly would break first. Would delivery grind to a halt because no one else can make final calls on priorities and trade offs, or would your team continue to run on the basis of clear roles and decision rules. When a project fails, can you trace that failure to a specific owner and a specific decision, or do post mortems blur into vague comments about communication and alignment. You can also look at your managers' calendars. Do they have regular, structured routines that reflect the leadership skills you say you want, such as one to one conversations, coaching time, and cross functional decision forums. Or are their days consumed by reactive firefighting and endless status discussions. Skills grow where the calendar makes space for them. If there is no such space, leadership development will struggle to take root no matter how strong the content is.
Effective leadership development begins not with training topics but with how work actually moves through the organisation. A more useful starting point is to identify the critical leadership moments at your current stage of growth. For a small product team, these might include prioritising the roadmap, handling tensions between sales and engineering, and speaking honestly with underperformers. For a regional team, they might include balancing local autonomy with central direction, navigating cultural differences, and representing the company to external partners. Once you have identified these moments, you can define in concrete terms what good leadership looks like in each one. In a roadmap meeting, for instance, a strong leader frames the problem clearly, surfaces relevant perspectives, guides the group through trade offs, and then makes a firm decision with explicit reasons and next steps. That level of specificity turns vague ideals, such as "be more strategic," into observable behaviours that can actually be learned and practiced.
On that foundation, training choices become more coherent. You might design workshops that rehearse those exact scenarios, peer groups where managers debrief recent difficult conversations, or shadowing arrangements where emerging leaders sit in on key meetings and later reflect with senior leaders on what happened and why. Development then becomes a layer that supports real work, instead of an isolated event detached from day to day reality. Even the best designed content, however, needs reinforcement through structure. Rather than relying on enthusiasm after a workshop, you can install simple routines that are hard to ignore. If coaching is a priority, for example, you standardise a monthly one to one template that includes progress, forward planning, and personal check in, and you expect every manager to use it. If cross functional leadership is important, you create a regular forum where leaders from different teams review shared metrics and make decisions together, with clear norms about preparation and participation.
There are moments where a large, formal program is the right call. If you are about to double headcount, expand into new markets, or shift from founder led to professionally managed, a cohort based experience for your core leaders can help align language, expectations, and relationships across the organisation. In such moments, the investment can accelerate a necessary transition. But when your organisation is still unclear about reporting lines, accountability for key metrics, or basic performance management, a heavy program is usually premature. In those situations, smaller, targeted interventions combined with structural clean up often generate a better return. Clarifying roles, tightening ownership, and putting a few strong rituals in place can create more real leadership growth than any number of inspirational sessions.
In the end, leadership development is a design choice, not a checkbox. It will always consume money and time, but it does not automatically create value. It pays off only when it is anchored to clear roles, real decision moments, and reinforcing routines that keep inviting people to step into stronger leadership. When it is treated as a branding exercise or a generic perk, it becomes an expensive distraction that disappoints both management and the very people it was meant to empower. The simplest way to tell which path you are on is to imagine stepping away for a while and then asking yourself a blunt question. Would the development work you have done show up in how your managers behave, the decisions they make, and the problems they solve in your absence. Or would the organisation quietly wait for your return before moving on anything that truly matters. Your honest answer to that question will reveal whether your leadership development is an asset, or a costly mistake in disguise.
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