Four Questions To Ask Yourself For Successful Task Delegation

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Task Delegation

Great things are never achieved alone; they always are team efforts. This is true for general business, product development, sports, family life or pretty much any other domain you could think of. Wherever multiple people are required to get a job done, coordination becomes critical.

Coordination can be among multiple people with similar skill sets (e.g. a number of Android developers or a number of designers), or different skill sets to achieve a bigger goal (e.g. building a product with a developer, a designer, a PM, a QA, a sysadmin, etc.).

Therefore, successful task coordination and delegation are key in doing great work. While it definitely takes a lot of practice and experience to successfully delegate and everybody develops their own style over time, there are a few guidelines which can increase the likelihood of success.

Based on my own experience coordinating various teams over the past ten years, from various sizes, cultures, and styles, I find the likelihood of a positive outcome to dramatically improve when the following questions have properly been considered:

  1. Are the task and the output expectation clearly defined?
  2. Does the other person have the skills to execute the task?
  3. Does the other person have the authority to execute the task?
  4. Have I handed off tasks to this person before I know “how he/she ticks” and how to set them up for success?

This article will explain these four considerations in more detail as well as give concrete tips on how to improve your task delegation.

1. Proper task definition

Task Definition

A common mistake I often encounter when people delegate a task (myself included) is that the person did not think of the desired outcome properly before delegating.

Sometimes, this can be due to a lack of specific knowledge of the person trying to delegate a task. An example could be when a business person asks a tech person to “assess if somebody is a good tech hire” without having pre-defined what “good” means (e.g. no guidance in terms of what kind of experience would be relevant, what the goals of that role are, the critical success factors, etc.)

Other times, it could be due to either ignorance (e.g. in the prior example, the lack of understanding that “a good tech hire” is a rather subjective judgement and hence, not easy to answer with yes/no), or because of a lack of time invested to properly think about the task.

It is important to understand that this does not have to mean that you micro-manage every person you are working with. A task can be delegated with a vague description (e.g. “create a product strategy”)—but in that case, it is crucial that the person delegated the task and the person is supposed to execute the task jointly discuss what is the real purpose of the task.

In the example of “creating a product strategy,” it could be that a CEO asks a VP Product to come up with the product strategy which is supposed to support the overall business goal of growing revenues by 50% while also increasing customer retention. The CEO may not have a clear sense of how to do that, hence, pass this major task to a VP Product. The VP Product should make sure he clarifies the real drivers for this task and not just accept the request to “create a product strategy.” Otherwise, he may find himself surprised if his self-chosen priority and resulting strategy to minimize technical debt is not met with the expected enthusiasm.

Clear scope and requirements need to be understood as a shared responsibility between the person delegating and the person receiving a task. The person delegating the task should ensure he tries to clearly communicate the task but also the person receiving the task should not hesitate to ask any questions and clarify until a common understanding is established. One relatively straightforward way of verifying a mutual understanding can be to ask the person you delegated the task to, to paraphrase the task and ask them to explain their approach to solving and what the solution will roughly look like. This way you can check whether this matches your expectations and if not, do early corrections without significant time being wasted.

In summary, however, no matter whether the task is small or very large, without explicitly setting a clear goal and discussing what “success” would look like, chances of a happy outcome radically go down.

2. Ensuring appropriate task-skill fit

Skill-fit Task

In one of the first management retreats I attended, the HR director of that company held a presentation on how to deal with poor employee performance. One of the key messages was to ensure a clear understanding of poor employee performance cause (potentially perceived). A key distinction made in her talk was to understand whether an employee is demonstrating poor performance because he is not motivated to perform better, or, whether he is motivated but does not have the skills to perform better.

Over time, continuously putting people into jobs where they do not have the necessary skills will lead to people losing motivation. However, depending on the organization and culture, in my experience (especially in the startup or social entrepreneurship world) it is quite rare for people to show very low motivation levels from the get go if they are treated fairly. A more common case with people who appear to perform poorly seems to be that they are put on tasks where they do not have the appropriate skills.

While it is rare for somebody to be hired for one thing and then being asked to work on something completely different (e.g. hiring a designer and then asking them to do sysadmin work), it is very common to be overly optimistic or ignorant of the scales and complexities of tasks. Selling newspapers on the street is different from selling enterprise software contracts to governments. Building WordPress websites with customized features is different from building core analytics engines for big data projects. While many people will intuitively agree with this, the reality is often grey and distinctions are not easy to realize.

This is further caused by the natural dilemma between trying to help people grow by stretching them far outside of their comfort zone, and (unconsciously) setting them up for failures by asking too much of a person. Finding the right balance between a tough “good” challenge and a pure hail mary task requires a lot of experience and insight into both a person’s abilities and a task’s requirement. Through critical self-reflection and over an extended period, you can sometimes see a personal trend, whether you may be “asking too much” of the people you delegate to despite the best of intentions.

In the case of poor performance due to lack of appropriate skills, there usually tend to be three major options:

a) ask the person to do a different task

b) train the person to do that task if it makes sense from a cost/return perspective

c) let go of the person

While the implications of option (a) are obvious, option (b) and © deserve a bit more explanation.

A company’s mission typically is different from a school in so far that training somebody to do a particular task is an investment decision. Is the time spent on training that person justified? Are there good reasons to believe that the person will quickly pick up the skill and deliver good value? Or is it a long shot and it would be much more economical to hire somebody else for that task?

As an example, if I were supposed to design an entire website from scratch, I would struggle to do a great job. Essentially, I would have to start from zero and after a few years of training, I may be able to do a reasonable job. At that point, however, the company would have had to invest a very large amount of time and money into me, when in reality there are many highly talented designers available who could hit the ground running quickly. Therefore, in this case from a business perspective, it probably would not be a good idea to try and train me.

If I am somebody with great overall development skills, deep architecture knowledge, and adequate leadership experience, and now I am supposed to lead a project in a new programming language, it will be natural to think about how I can quickly learn and adapt within a few weeks and the overall benefit I already brought to the table is significant.

For case (b), an assessment has to happen of how big the gap is and whether it makes sense for the company to try and train the person to bridge that gap or whether finding someone else.

Case © can often be very difficult for young managers as it seems harsh to let go of somebody who is very motivated yet does not perform.

Personally, I am no friend of firing quickly and have a certain level of skepticism towards this option as I have found many less experienced managers to be overly fast to assume the person “isn’t working out” when it could be at least partially due to the way that person is being managed.

Despite maybe sounding slightly counterintuitive, I would argue that in these cases, a manager almost has a moral obligation to work with the employee on a clean way to let the employee go. Ultimately, that situation is neither long-term feasible for the company, nor the employee and a manager has no right to “waste” an employee’s time by trying to ignore the problem and not helping the employee find a better environment or set up elsewhere.

Understanding an employee’s skills in order to match skills and tasks is a task that requires experience and a lot of skills of the manager. The reality often is quite messy with few clear cases of mismatches and a lot of gray areas. Keeping such basic considerations in mind, however, can definitely help to improve the likelihood of success.

3. Authority to execute a task

Task Authorization

Imagine Jose Mourinho, a professional football manager, were to attend an amateur club’s football match. There is little doubt that he will be a more experienced and better manager than the manager of that amateur football club.

However, sitting on the sideline, he has no authority to give orders to the team and even if he were to demand one player to be substituted for another player, it would not happen unless the actual manager decides to make such substitution. At the same time, even though Mourinho may be the expert, nobody expects him to be calling the shots either. He has the skills, but is not responsible, doesn’t have the authority to execute and is not under the expectation of leading that team.

This extreme example is fairly intuitive, and the dynamics in football teams are well enough understood to follow this case. However, in teams similar situations can arise where somebody would delegate a task to somebody else who may have the skills and now is under the expectation to perform, but does not have the authority. This could be because, in order for that person to do their job, they require input from a third person, yet, that third person is not aware of his required contribution or, in particularly bad cases, refuses to cooperate. As a manager, therefore, it is crucial to ensure that when you hand off a task, you not only pass on the expectation for the person to perform but also provide that person with the authority to perform accordingly.

Providing somebody with the authority to behave in certain ways requires trust in that person’s judgement and that can be tough, especially for inexperienced managers. Full authority without any oversight can also be problematic, hence striking the right balance is key. In my experience, that is best achieved if both parties know each other reasonably well leading to the fourth consideration: prior joint experience.

4. Prior joint experience

Build relationships not databases

Managing people by definition has to do with people and the relationships you build with them. Each relationship is unique and relationships change over time (whether better or worse depends on the investment both parties make into the relationship). If you have worked very closely with somebody for an extended period, sometimes a simple sentence is enough to convey a complex idea. That same content, however, may need a one-hour meeting with somebody you have not worked with before.

When working with anyone new, I like to roughly apply a principle called “additive increase — multiplicative decrease” — something I first heard from a long time ago, surprisingly, with regards to an entirely different domain: network traffic congestion handling.

The idea at this momenthereby is simple because network bandwidth is limited overall and it is unclear at any given point how many different users are using that bandwidth, your computer would linearly increase the amount of data sent per time unit starting from a very low baseline as long as no collision is detected. If things go well, over time, you will enjoy a faster and faster connection. However, the rate of data transfer is halved each time a collision is detected. Therefore, it could be viewed as a carefully optimistic approach with strong “insurance” if things don’t go well because it decreases much faster than it increases.

When working together with somebody for the first time, I like to follow a somewhat similar approach. I will carefully try and start by handing off smaller tasks. If that seems to go well, I will keep handing bigger and bigger tasks while taking a more and more hands-off approach. However, if things didn’t go well, instead of slightly correcting, I would get much more involved for a short period before gradually handing off again.

I am a fairly optimistic person by nature and time is always limited and probably my biggest constraint. Hence, unless things blow up, I assume they are ok. However, this can mean that problems may remain unnoticed for a bit longer than they ideally should. Therefore, I personally find it to be much better for me to then take stronger immediate corrective action (exponential decrease) if things don’t go well, rather than being too slow in adjusting (linear decrease).

This approach can also work for other areas of management like onboarding people—you work with them the full first day, then maybe half the second day, spend two hours with them on the third day, one hour on the fourth day and then maybe stick with a rhythm of one hour every 2–3 days if things seem to go well. If there are signs of a problem, instead of spending slightly more time with them, you immediately spend a LOT more time with them. This in my experience allows for a better overall return on time spent, as ultimately problem prevention and early solving almost always ends up being less resource consuming overall than fixing a problem when it as become so big that it can not be ignored anymore.

Whether you chose this kind of heuristic or a different approach certainly depends on your own personality, experience, and style. The important takeaway message from my perspective here though is that, again, task delegation and management depends on the particular person you are dealing with and the more time you spend together, the more likely it is for the two of you to develop a good joint working mode.


In this article, we started by looking at some of the components of successful task delegation. Based on four specific questions, I tried to show you that often a rich experience and good judgement is required which leads to successful task definition being a somewhat “messy” problem. Being a crucial piece of management, we have seen how task delegation also quickly touches other considerations, introducing additional complexity. However, all said and done — I do believe that by keeping the aspects above in mind, you can dramatically improve your awareness of what task delegation includes and therefore improve your chances of success over time.

Please feel free to share any questions, insights or other good guiding principles you have found in the comments section below as I also believe that this is an area where everybody can keep learning and there always is further room for improvement (definitely I know that this is the case for myself!)