There comes a point in every founder’s journey when you quietly wonder whether all the money and time poured into leadership training is actually changing anything. You look at the invoices for workshops and retreats, remember the photos from the resort ballroom, and then compare that with how decisions still get stuck in the same bottlenecks. The trainers came and went. The slides were polished. Yet the way your managers lead, speak up, and handle pressure looks more or less the same. It is an uncomfortable thought, because it forces you to ask whether you have been buying real development or just well branded theater.
The truth is that leadership development is not a bad idea. In growing companies, especially in Southeast Asia and the Gulf, it is a survival need. The problem is how it is usually designed. Too many programs exist as one off events, disconnected from the actual flow of work. They are built around what sounds impressive to a board or an HR brochure, rather than what your people are struggling with on a Tuesday afternoon when a client threatens to escalate or a project begins to slip. When development is divorced from reality in this way, it rarely pays off. When it is anchored in the live problems of your business, it becomes one of the highest return investments you can make.
Designing leadership development that truly pays off starts with a very specific question. What business problems do you need this program to solve in the next twelve to eighteen months. Not in theory, not in a generic sense, but inside your actual company with your current team and runway. Are you trying to reduce founder dependence so that the company does not panic every time you are traveling. Are you trying to scale a bench of managers who can run new locations or product lines without hand holding. Are you trying to keep your best people from quietly checking out because they see no path upward. Unless you can name these tensions clearly, everything else you design will be vague and decorative.
Once the real tension is named, the design process should move from the work backwards, not from theory downwards. Many leadership programs begin with competency models, personality tests, or abstract values statements. They sound sophisticated, but they float above the daily grind. In reality, leaders grow when they are given responsibility for real outcomes that stretch them beyond their comfort level, with enough support that they do not collapse under the weight. So instead of opening a catalog of generic workshops, start by mapping your most critical pieces of work for the coming year. Think of product launches, key accounts, cross border expansions, restructuring efforts, or core system migrations. Then ask a hard hypothetical question. If you and your cofounder disappeared for a month, who would carry each of these on their shoulders.
From there, leadership development should be built around stretch roles, not just learning sessions. A stretch role is not a vague promotion. It is a clearly defined piece of ownership that truly matters to the business and is just challenging enough to require new behavior. It comes with real decision making power, clear boundaries, and a visible safety net that allows for mistakes while still holding a standard. The workshops, coaching, and content form the scaffolding that supports these roles. They should never be the main structure. When the program is a wrapper around meaningful responsibility, leaders learn through doing, reflecting, and trying again, rather than through absorbing abstract ideas.
This approach transforms what your calendar looks like. Instead of packing schedules with disconnected classes on communication, emotional intelligence, or strategic thinking, you anchor development around ongoing projects and decision rights. For example, if a manager needs to learn how to lead cross functional work, they should not only attend a module on collaboration. They should be the one chairing the weekly cross functional meeting, writing the brief, negotiating tradeoffs across teams, and closing the loop with stakeholders. The friction they experience in these tasks becomes the raw material for learning. Your role, and the role of any external partner, is to make that friction visible, safe to discuss, and structured into repeatable lessons.
For that to happen, feedback has to be frequent and honest enough that it sometimes stings, but safe enough that people can absorb it without shutting down. Many organizations outsource feedback to anonymous surveys and third party coaches because it feels neater and less personal. While external voices can help, the real transformation happens when feedback becomes a normal part of how the team operates, not a rare ritual. A short debrief after a tough client call, a quick reflection after a product launch, or a monthly one to one that focuses on leadership behavior rather than status updates can carry more weight than an expensive offsite. When people expect to review what went well and what could have been better, they start to see themselves as active learners instead of passive recipients.
A common trap is designing leadership programs only for those who already look like leaders on the surface. Strong presenters, confident speakers, and politically savvy individuals often receive most of the attention. In early stage companies, however, some of your most important future leaders are the quiet operators who keep projects steady, build trust inside the team, and solve problems without drama. If your leadership development only rewards visibility and smooth talking, you send a signal that optics matter more than substance. By grounding development in real ownership instead, you give quieter contributors a viable path to grow without forcing them to mimic a personality that does not fit them.
Culture adds another layer of complexity that founders in Malaysia, Singapore, and KSA ignore at their own risk. Many people are socialized from school and early work experiences to respect hierarchy, avoid open conflict, and keep criticism private. At the same time, companies say they want proactive leaders who challenge decisions, raise concerns early, and take initiative. Imported programs that copy Western leadership styles word for word often clash with local expectations and quietly fail. The answer is not to lower the bar for leadership. It is to teach practical ways to disagree and escalate within the culture. People can learn how to question decisions using data, how to ask clarifying questions instead of making accusations, and how to surface risk in a way that protects relationships and allows others to save face.
Another reason many leadership programs fall flat is that they talk about influence but never touch actual power. It is easy to run training that teaches people how to persuade stakeholders or manage up. It is much harder to change who actually has authority over key decisions. If every major call still flows through the same two founders, your managers will quickly understand that the program is mostly symbolic. The real curriculum is who gets invited into which conversations, who signs off on what, and who is trusted with information. To make leadership development real, you need to open up at least a few decision forums and bring emerging leaders in as co decision makers, not just note takers or observers.
For founders, there is also a mindset shift required. Leadership development is often framed as a benefit for employees or as a line item under HR. In reality, it is a hedge against your own limitations. By committing to a deliberate pipeline of leaders, you are buying back your future time and attention. You are securing shorter approval cycles, fewer emotional fires that only you can put out, and more capacity to focus on the moves that actually change the trajectory of the company. Of course, this means surrendering some control and accepting that people will make imperfect decisions while they learn. The question is not whether they will stumble. The question is whether your system treats those stumbles as tuition or as evidence that only the founders can be trusted.
Measurement should support this mindset, not complicate it. Many organizations obsess over sophisticated engagement surveys and elaborate leadership scorecards. These can look impressive but consume energy and rarely change day to day behavior. Instead, focus on a handful of signals tied directly to the problem you set out to solve. Are more decisions being taken at the right level without constant escalation to the top. Are cross functional initiatives shipping closer to schedule without burning people out. Are your best performers staying and saying yes to bigger roles instead of leaving because they feel stuck. Are customer issues being spotted and resolved earlier, so you hear about them sooner and in a calmer way. These practical indicators tell you whether your investment in leadership is compounding or just smoothing over symptoms.
There is one more uncomfortable truth. When leadership development is done properly, it does not only create growth. It also exposes misalignment. Some people will discover that they do not actually want the tradeoffs that come with leadership. They may enjoy the status that comes with the title but resist accountability when things go wrong. Others may attend every session and nod at every principle, only to revert to old patterns once pressure hits. This is not a sign that your program has failed. It means your program is revealing who is genuinely willing to grow with the company and who is not. It is better to see that clearly while the organization is still adaptable than to discover it when you are trying to scale across regions with a shaky leadership core.
If you are serious about building leadership development that truly pays off, the first move does not involve a grand blueprint. It involves a focused experiment. Choose one or two strategic projects for the next quarter. Assign them as stretch roles to emerging leaders. Wrap those roles with consistent feedback, simple coaching, and clear decision rights. Adjust your own behavior to match the level of trust you claim to want to give. Watch closely for six to twelve months and be honest about what you learn. In the end, the real engine of leadership development is not a deck, a slogan, or a venue. It is the way ownership, feedback, and power are designed inside your company. When those elements are aligned with the realities of your culture and your strategy, you do not just create better leaders. You build a business that moves with or without you in the room, and that is when leadership development stops being a nice idea and starts becoming a genuine multiplier.
WhatsApp
Instagram
Threads
