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Delegation: Key Leadership Skill


I recently heard from a friend--a brilliant, highly skilled, and charismatic leader--who said that she "stinks at delegating." It turns out that a lot of people have a problem with this skill, and it is particularly difficult for many women. Perfectionism and hard work may get us promotions, but after a certain point, a manager has to be able to delegate authority in order to free herself to be a leader. Leaders think big thoughts; they don't line edit every document that leaves the office.


The delegation process.


Depending on your position in an organization, you may be delegating whole projects or easily definable clerical tasks. The same general process can be applied to assigning a project to a team or assigning routine clerical tasks to your assistant:


  1. Identify what can be delegated;

  2. Determine the objectives of the task;

  3. Identify who is available to do the work;

  4. Decide on the delegate's level of authority for the task, based on skill levels and job description;

  5. Set milestones, methods for reporting progress, and what support and resources will be needed;

  6. Communicate clearly your expectations and needs up front;

  7. Let them do the work;

  8. Follow up, as needed, giving constructive feedback and coaching for future projects.


Up-front effort is a long-term investment.


Many people get caught in a trap of thinking, "It will take me longer to delegate this than it will to just do it myself." Yes, it will take you less time to do that single task, but if you take the time to train someone else to do it now, they will be able to take on similar tasks in the future. Moreover, involving your staff in projects and giving them meaningful work increases their skill and motivation. Good delegation increases trust and strengthens your whole team.


What to delegate?


First, consider what you do every day. This time log can be used to jot down what you do in a day and to help you think through whether each task has a high impact on the work you do (planning, visioning) or whether it is something that you can delegate to someone else. I like to do this kind of log every now and then as a reflective exercise. It can act as a wake-up call about how I'm balancing my work and where I'm putting the most effort.


You don't want to delegate high-profile tasks when there is a time constraint or a high risk of error. It might be best to manage sensitive relationships yourself, for example. Hiring and recruiting is also a high-impact task that is best to keep close tabs on. Without good people, teams fail and delegation is impossible.


The easiest things to delegate are those which have well-defined rules and parameters. Routine administrative tasks, like regular reports, paperwork, claims sheets, or data gathering are also good to hand off to someone else. If you are a bit of a control freak about major projects, keep your eye out for small portions of a larger goal that you can hand off to someone else. Also, be aware of your team's strengths and your own weaknesses. When you delegate things you hate to someone who enjoys the work, morale increases along with outcomes.


An example: The Spreadsheet from Hell


I started working on the Spreadsheet from Hell sometime last week. We are cleaning up vital data sets to make information more accessible to our customers. That's the big picture and the ultimate goal.


For most of the data set cleanup, automation is my go-to for delegation because a computer can do the work of months in a matter of minutes. But the Spreadsheet from Hell is a rebel, with over 1000 lines of wrong check-digits and mismatched text. It refuses to be simply uploaded where it belongs.


It is not worth my time to input each and every line of data manually. It's time to delegate.


Who to delegate to?


As I said, automation is the first go-to for delegation, whenever possible. From there, you want to delegate a task to the least costly staff member on your team who has the skill and job description appropriate for the work. In the case of The Spreadsheet, I plan to give it to a part-time staff member who is very careful with details and follows written directions well. Checking up on the completed project will be tricky, so reliability is an important aspect of delegate selection.


Good management in other areas makes delegation easier. Hiring good people is important. Once hired, you have to know your team's skills and strengths. You must trust them, and they must trust you. You have to know that they will complete the task to the best of their ability. In turn, they have to trust that you aren't going to jump down their throats if they ask questions or make a mistake.


Delegation can be an opportunity to mentor team members' growth if a project or task would benefit someone's goals or aspirations. Sometimes, this means providing more support for the project than you would when delegating to a more experienced team member, but the long-term benefits can well outweigh the drawbacks.


Identify details of the task and objectives.


Identifying who will do a task is inextricably linked with what the task requires. In the case of The Spreadsheet from Hell, I decided to create very specific written instructions with screenshots for each step of editing, uploading, checking, and troubleshooting.


The objective of the task is to a) get the information uploaded; b) make sure that what has been uploaded actually works. So the instructions make it very clear how to meet those two objectives.


Identify and communicate the delegate's level of authority.


The Spreadsheet from Hell is only a tiny part of a larger project. The delegate on this project has little experience or skills in the system, so her scope is limited to this task. However, in doing this limited task, I hope she will learn details of our systems. If she is self-motivated to gain more authority and autonomy, she may explore the systems now that she has access to them. Once she has increased her knowledge, I can assign her larger parts of the project that require more judgement and authority.


I would normally delegate the whole project to a person whose primary job description is to provide customer access to electronic resources. Let's call this person the Data Manager. (Unfortunately, I have no one working in that particular position right now). The Data Manager would have full authority over completing not only this task, but the whole data project, and their work would be evaluated based on bigger picture outcomes. Ultimately the Data Manager would be responsible for answering the question, "Can our customers get to the information we have paid for?" That is a much higher level of authority and responsibility than the Spreadsheet requires; in turn, that person would have more autonomy over their work and how they reach their objectives.


Provide appropriate resources and support.


The person you delegate to will need more or less support and resources depending on their basic competencies and their commitment to the work. For example, the woman who will be working on The Spreadsheet from Hell doesn't know the systems or how they work. She has, in the language of situational leadership, "low competence." She does have a strong commitment to the job, however. Therefore, she needs very specific directives, but she doesn't need a lot of emotional support to finish the task. That means that I can hand her the project with specific instructions, and trust that she will get the work done.



Set milestones, deadlines, and methods for reporting progress.


These, too, depend on the skill and job description of your delegate. For the Spreadsheet from Hell, I will simply designate a deadline for the entire task, and have the person doing the project let me know when it is done. Early on, I will check in to make sure that the instructions are clear, that she is comfortable doing the task. I will also check with her to make sure that she thinks the deadline is reasonable based on how quickly the project goes and how it meshes with her regular workload.


If I were delegating to the Data Manager, we would collaborate on project goals and milestones, and set milestones for reporting progress. For example, I might ask them to let me know when each large data set is up and running, or when a certain percentage of databases are complete.


Pro Tip: I have found that setting milestones and reporting progress through a project/team management tool (we use Asana) helps me micromanage less, saves me time, and helps me keep a birds-eye-view of the projects we are all doing. When I give instructions verbally, or people come to me with progress reports, I tend to go into problem-solving mode, which does not help people learn to think through their own roadblocks. By putting everything in Asana, we reserve our in-person meetings for planning and collaborating, and I provide support and problem-solving when they request it, not because I'm a meddling manager.



Let them do the work.


If you do all the steps above with clear communication, you should be able to step away at this point and let your delegate do the job. If you are constantly looking over their shoulders, you aren't doing your own work, and you haven't really delegated anything. You are also communicating that you don't trust them. Your goal, as a manager, is to hire good people, support them as they need it, but get out of their way and let them do the work. People with some autonomy at work are happier and more productive than those with little or no freedom over their work lives.


Give useful feedback and use it as a coaching opportunity.


When you give feedback on the completed work, focus on the outcomes of the project, not the process for getting there. Let them know what they did well. Ask leading questions to help them reflect on the work they did and how it might be improved in the future. (How do you think that went? What challenges did you have?) If they don't identify the weaknesses of their work on their own, provide specific and objective information, free from emotional judgments. ("I tested some of the links you have been working on, and I noticed that quite a few are broken. Here is one example. What do you think happened there?) In an ideal world, you say all the right things, and your staff responds with openness and honesty. When it doesn't go well, the conversation is likely to escalate into a blame game. Step away from that situation as tactfully as possible and do your own reflection on how to improve the conversation the next time.


How to let go


For the perfectionists and control freaks among us, letting go is the hardest part. You have to accept that your delegate is unlikely to do the task exactly the way that you would, especially in a task that has fewer hard-and-fast rules than The Spreadsheet from Hell.


1) Focus on the outcomes.


The scenario: Say you want your assistant to call 100 people by the end of the week, and you need notes on each of the calls. If you were doing the project, you would make the calls all at the beginning of the week, as quickly as possible, and write up your notes as soon as you complete each call. You are shocked to discover that your assistant has spread out the work to make 20 calls each afternoon and to take notes while the client is still on the phone. You are sure this is a terrible plan and that she won't be able to pay attention to the clients while writing notes. You also want the project done as soon as possible.


Before you jump in and tell her exactly how to make the calls, think about the objectives of the task. Do you really need the calls complete before Wednesday? If so, why did you give a Friday deadline? Consider that your assistant's personality is different from your own. She may listen better when taking notes. She may have more energy and feel more personable in the afternoon than in the morning.


2) Know your own hot buttons, plan for them, and communicate them.


I once had a boss who edited everyone's writing to death. I am no slouch at writing, but I once wrote over 10 drafts of a single document to respond to his line edits. Yes, it was an important report that was going to the state. Yes, a person should write multiple drafts of anything to make it as readable as possible. But with him, each and every draft wasn't getting clearer; it was just getting closer to his writing style than my own. By the time I left his line of command, I had stopped writing multiple drafts of my own before giving it to him, and I learned to give him reports close to external deadlines to force him to make all his edits at once.


When I started delegating writing projects to others, I found that I have the same tendency. It is hard for me to let something leave our offices written in a tone that is not my own. I have struggled with letting go of my need to control these things. The last thing I wanted to do was to have my skilled staff respond as I had done, with much less commitment to the task and sizzling resentment.


I have finally decided to change what and how I delegate written projects. If I care deeply about how an item is worded when it leaves our offices, I delegate writing a "draft" of the piece, not a completed project. I let the team member know that I want them to get the important points down in writing and I'll do the final polish on the piece and send it out. It takes less time for me than drafting from scratch, but I still have final authority and voice.


If I care less about how an item is worded, but I want particular content included, then I can give details on the content to the team member and trust them to polish the work. It won't sound like I wrote it, but if I trust the person to write grammatically and clearly, I can let it go.


3) Value individual difference, and know your team's strengths.


No one is going to do a task exactly as you would. If you have hired good people and you know their strengths, delegate to match those assets. When possible, create teams that have all the skills necessary for a project. For example, if you need to have an infographic created for your business, you might put together a team that has someone with graphic design skills, someone with research skills to locate the data, and someone with writing skills for the copy.


The challenge on small teams is that you need each person to have a broader range of skills. That might mean that you have to depend more on your own skill set. You will either provide detailed instructions up front, or you will have to do more of the work yourself. Investing time and resources into broadening an individual's skill set increases their value to the team.

Ask for help to up your game.

Delegation can be a real challenge, and it is intertwined with other factors of being a manager in a way that is sometimes hard to untangle on your own. If you would like to talk through your leadership and management challenges with an objective outsider, consider hiring Messy Desk Consulting for leadership coaching. On-site or virtual workshops with teams are also available, tailored to your organization's functional needs.















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