How do you delegate effectively? What holds people back from delegating tasks?

I would add in the Do # 2, ask the employee to paraphrase what you're requesting. It's a common problem that people say that they understand what you say, and when the deadline comes, the result is not the expected. I call this practice "duplicate".

Professionals hold back from delegating when they 1) feel it will take to long to teach someone else how to perform the task and 2) fear the task will not be performed to the level they expect. Delegating effectively requires building a team you can rely on. Employees and contractors who consistently show initiative and success in their projects are more likely to be delegated to. Project management programs (ie Basecamp, TeamworkPM and Podio) allow collaboration on projects, while at the same time allowing tasks to be delegated with a clear expectation of deadline.

Delegation of work is necessary and important. The key factors that hold people back are their need for control and their sense that no one else can do what they do as well as they do it. In reality, we have to give up control as delegation is crucial for the success of any venture. There are no large companies today with less than 10 employees because as companies scale they hire people and allocate responsibility to their team.

To delegate effectively here are few ways, that I have noticed in the leaders in the companies employed that I had worked with:
1. They pick the right person — and it is not always about who can do it. Who needs to develop these skills? Who has capacity? Who has shown interest? Who is ready for a challenge? Who would see this as a reward? Successful delegators also explain why they chose the person to take on the task.
2. They are clear about what the person is responsible for and how much autonomy they have. In Drive: The Surprising Science About What Motivates Us, Daniel Pink writes that people often want autonomy over task, team, technique, and time. Successful delegators let their team members know exactly where they have autonomy and where they do not.
3. They describe the desired results in detail. This includes setting clear expectations about the outcome (“what it is”), how the task fits into the bigger picture (“why we’re doing it”), and criteria for measuring success (“what it should look like when done well”).
4. They make sure that team members have the resources they need to do the job, whether it is training, money, supplies, time, a private space, adjusted priorities, or help from others.
5. They establish checkpoints, milestones, and junctures for feedback so that they neither micromanage nor under-lead.
6. They encourage new, creative ways for team members to accomplish goals. It’s important for delegators to set aside their attachment to how things have been done in the past, so that they can invite, recognize, and reward novel approaches that work.
7. They create a motivating environment. Successful delegators know when to cheerlead, coach, step in, step back, adjust expectations, make themselves available, and celebrate successes.
8. They tolerate risks and mistakes, and use them as learning opportunities, rather than as proof that they should not have delegated in the first place.
Blockades to delegation are as follows:
1. Wish to perform tasks personally: This is one of the most significant Barriers to Delegation as many of the seniors and managers wish to complete all the work tasks and responsibilities personally. They feel that they will be in a better position to handle somewhat the same to their team. Delegator also feels that handling all the crucial tasks by himself will give him better control over others in the organization and creates his positive image in front of the management. Plus, it will also get him more importance by showcasing his skill set.
2. High levels of insecurity: Insecurity is also one of the prime reasons due to which managers do not delegate their responsibilities to their subordinates, teammates, and even to the management trainees. They have a constant feeling of fear and insecurity that if the other team members perform the task in a productive and better manner in his comparison, his position will be in danger. Such mindset and tactics can also be termed as manipulation as the subordinates, and other members of the team are not given a fair chance to showcase their skills and expertise.
3. Power and Authority: Many of the managers work with the constant mind perspective of having fully-fledged power and authority in their hands. They handle all the main tasks and responsibilities personally, and the ones that are not incredibly challenging enough are handed over to their subordinates with little or limited information. And this way, subordinates have to come to them again and again for inputs that make the delegator feel in command and authority. And this way, he can paint a positive picture of him in the eyes of top management.
4. Lack of trust and confidence in subordinates: Yet another one of the crucial Barriers to Delegation is the superiors having a lack of trust and confidence in subordinates. Along with the factors of faith and trust, there is also a factor of risk involved as the superior cannot take the risk by delegating vital and crucial tasks in the hands of the subordinates. If the subordinates are not capable enough to handle an imperative task, the superiors must display the attitude of handholding and support for the completion of the task as teamwork. The management also must take necessary corporate actions such as training and development of the employees if it wants to retain them for a longer period and increase the efficiency levels of work.
5. The organized structure of work: If the manager himself is not very capable and efficient enough to delegate the tasks and responsibilities to his team in an organized and structured manner, it acts as one of the Barriers to Delegation. There are complete chaos and a lot of issues in such a scenario as no one of fully aware of his roles and responsibilities as the delegator is not competent enough to handle and manage his team effectively.
6. Personal issues: Many of the managers have some of the other personal issues with some of the members of his team that result in the Barriers to Delegation. Personal issues can be aroused owing to various reasons such as competition, insecurity, personal bias, and others. This can also be counted as an unfair method as it does not provide a fair chance to others to prove their worth. It is very vital that delegator should understand that personal and professionals cannot be mixed and intermingled at the workplace. And such petty issues affect the overall environment of the organization.
7. Fear of failure: Many a time, the attitude of subordinates also acts as one of the Barriers to Delegation. They have a fear of failure and have a lack of confidence in taking over and effectively completing the tasks. And that is the reason they shy away from taking more workload and responsibilities on their shoulders.
8. No incentives: Quite several times subordinates and employees that are relatively new shy away from taking responsibilities owing to the lack of incentives and fruitful rewards from the organization. Hence, it is very necessary for the management of the firm to keep the employees motivated by rewarding them with good pay packages and incentives.
9. Lack of convenience: If there is a factor of lack of convenience and basic facilities for the employees to fulfil their tasks and responsibilities, they do develop a barrier in their mind to take additional responsibilities from their seniors. An organization should provide basic facilities such as travel conveyance, good IT facilities, good infrastructure, and other such vital facilities.
10. Organization size: Barriers to Delegation also result due to the size and scale of the organization. Small and medium scale organizations work a flat structure and hierarchy levels with no proper delegation structure, and authorities provided to the employees of the firm. Whereas large scale organizations have too many layers and hierarchy levels that result in various issues such as insecurity, fear of losing power, authority, and more.
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