The Art of Delegation

TL;DR Want to lead well? Start delegating well. Most leaders think they’re delegating—but in reality, they’re either micromanaging or abdicating. Instead, use mandates to transfer real power.

There are two basic types of delegation. You can delegate a task, or you can delegate an outcome. To illustrate:

During WWII, future Yugoslav dictator Tito earned his nickname, which in the local language means, literally “You-that”. Tito would be walking among his troops, see what needs doing, and point to the task and the person close by able to tackle it. Perhaps this is how all dictators get started. Doubtful veracity of the story aside, it illustrates the first level of delegation – easy to observe tasks that can be quickly delegated and likely quickly completed. If you do that often enough, you might get things done AND get a reputation.

Now consider the second approach: delegating an outcome. During the 16th century, England and Spain were engaged in their own version of a cold war. Seeking to enrich the crown without provoking outright conflict, Queen Elizabeth I issued a “Letter of Marque” to Francis Drake. This commission authorized Drake to target Spanish ships and ports and take a share of spoils legally. It was a legal license to do piracy—no micromanagement, just a wickedly clear outcome: “Go annoy Spain. Come back richer.”

Delegating in this way also gave the crown plausible deniability—a useful political tool. In practice, broad authority was often necessary for distant expeditions, whether of discovery or plunder (sometimes a blurry line). Direct oversight from the court was impossible due to distance and slow communication. To accomplish anything, leaders far from home needed significant autonomy.

Delegating outcomes empowers people to use one’s own best judgment to decide what and how specifically needs to be done. The practical result is a very high degree of autonomy and separateness.

Delegation is an ancient problem, mostly related to statesmanship. In today’s world, however, it mostly occurs as part of running large and complex business organizations.

The modern state of delegation

No. 1 complaint we hear from CEOs is that their senior leaders are not doing what they need them to do. The most frequent complaint we hear from the senior leaders is that they are not clear on what is required of them and do not feel empowered to do their best work. In short, delegation is broken.

The pathologies we see most often:

• Task Delegator in Chief. Many founders pride themselves on “rolling up their sleeves” and tackling details. While admirable at first, this approach doesn’t scale. Only tasks that catch the founder’s attention get done, and senior hires soon feel sidelined, waiting for their turn. Founders become bottlenecks, and progress slows— your cute startup habits are now company-killing bottlenecks.

• God of the Gaps Leaders. Some leaders escape the first trap, delegate outcomes but realize they have not clarified how trade-offs and decisions will get made and coordination costs managed – and quickly get sucked back into detailed work as they try to align their leaders, manage silos and egos, and unify the organization. It is hard and unfulfilling work.

• The Talent Churner. Sometimes leaders swing too far toward outcome delegation. They hire top talent, hand over big objectives, and step back. While empowerment is real, expectations remain unspoken—how things get done, what success looks like, or what “fit” truly means. Delegation often becomes “take care of this” without clear direction. When results fall short, failure is blamed on the talent, not the lack of clarity. The result? A costly cycle of hiring and firing, and a myth that “only special people succeed here.”

• The Missing Leader. Some leaders are like a horizon, more of a concept than a lived experience. They give very broad remit that can be summarized as “be successful and do good work”, and then leave others to it, acting only when high-level outcomes are not delivered, and then acting mostly to reprimand and fire. Their key and only question is “have you delivered?”. Managing by OKRs is a popular enabler of such leadership.

I am sure there are many others; this can be left as an exercise to you, dear reader. Common denominator across these predictable mistakes is that leaders need to find a good balance between “delegating a task” and “delegating an outcome”. Modern organizations attract talented people who resist micromanagement, yet they still need enough structure and coordination to prevent chaos. Full autonomy rarely works; thoughtful balance is required. How to find it?

The Mandate approach

Stop giving key hires jobs and start giving them mandates. Mandate is a container for agency – it delegates much more than a task or a project, but it does not quite delegate full autonomy. When it works well, it provides the right balance of clarity, support and freedom – it enables agency. It delegates power.

It has three main components:

I. What does success look like? Senior leaders have titles, job descriptions and KPIs. But, often, these things serve to obscure not clarify the mandate. What is the job of a CFO at this company, at this time? Is it to ensure we don’t run out of cash? To enable fund-raise and manage investors? To control budgets and therefore other executives? What is considered most difficult and why? The right answer provides clear alignment on priorities and how they stack up.

II. What can you actually decide? What is this role authorized to do in terms of budget, decisions and trade-offs to manage. What exactly is the power being delegated? And, most importantly, what is not being delegated? Where and how is the role expected to align with others?

III. How will we work together? How exactly will the work be overseen? How does the leader like to work? What is expected in terms of frequency and depth of updates? What needs to be escalated and how? This will vary significantly based on the familiarity of the CEO with the domain, skills and reputation of the person delegated to and perceived importance and difficulty of the task.

That’s it. That’s the whole system. Easy?

In our experience, it takes real time and energy to build deep alignment on these questions. It’s not about filling out templates or ticking boxes. Instead, it requires honest conversations, surfacing disagreements, and working through misunderstandings—until everyone is truly on the same page.

It is an effort, yes, but it prevents significant tensions and mistakes down the road – and the fact that this process is somewhat difficult to go through just indicates the likely misalignment that would’ve happened if this work did not take place. And, as with any process, it needs to be periodically renewed (at least annually!).

Why this breaks (and how to fix it)

Having led this process for a set of clients, here is where things typically snag:

• Strategy misalignment. It is sometimes unclear what exactly needs to be done and how the tasks can best be “chunked” out to enable their delegation. In other words, strategy is not clear enough. Fix that first. This does not mean strategy needs to be perfectly clear – questions, explorations and uncertainties too can be delegated.

• Self-defining roles. We often hear leaders saying that they are paying top dollar for top talent, and therefore it is a waste to tell them what to do. They mean “how”. You should certainly not micromanage talent coming in, and they can refine their own tasks – but you are hiring them for a reason and need to specify that reason. You would not call a plumber without defining what needs fixing, even if you know nothing about plumbing. Did you just say, "be smart about pipes"?

• Founder Mode. Founders are not the same as CEOs. They tend to be deeper, even foundational, in some areas of the business – and you do not want to lose that genius by delegating it away. Fine. Keep 2-3 things. Micromanage the hell out of them. Delegate everything else. If founder needs leverage, make sure it is clear that’s what’s required – they are calling the shots in this domain, and leaders joining will experience some first-class micromanagement.

• Romanticizing the early days. Experience of “garage team” is one of camaraderie; frequent interaction, iteration and alignment – an almost constant course-correction. The intensity of this process is enchanting - early stages of scale-ups are usually stories of epic teaming of this sort, and quick task delegation. And yet, as companies get bigger jobs get bigger and it is time to accept that some mandates will be required. Your nostalgia is costing you. Let. It. Go.

Ultimately, leaders must face some tough truths: growth brings imperfection, complexity, and a loss of the cozy control of early days. You can’t scale what you can’t let go. The intimate, all-hands problem-solving of a 10-person startup doesn't work at 100 people and definitely breaks at 1,000.

But here's what most leaders miss: Letting go doesn't mean abandoning your team. It means creating clear containers for autonomy—mandates that empower without abandoning. Mandates aren’t bureaucracy—they’re your secret weapon against misalignment.

Start small. Pick one direct report. Spend three hours creating a real mandate together. Delegate power and accountability instead of a task. Watch what happens when someone truly understands what success looks like and has the authority to achieve it.

That's delegation that scales. That's the art of delegation.