Would You Skydive Without a Parachute? How to Delegate With Confidence.


Roger had been working way too much and knew he needed to reprioritize and delegate. But he was nervous about letting go of control and was having difficulty identifying what he could delegate.

I was surprised when he mentioned he was going skydiving to celebrate his 50th birthday.  As a manager, he was practical and task-focused.  This was a side I hadn’t seen before. It was hard to imagine him jumping out of an airplane, totally out of control, free falling at 10,000 feet. It seemed out of character. 

Honestly, it would be out of character for me, too. I considered what I would need to be ok about jumping. Here’s what came to mind:

  • Training – Instructions and the opportunity to practice my skills in a safe environment.
  • Motivation – To know why I should do it and encouragement to hang in there as I developed confidence.
  • A parachute – I’m not jumping unless I have the necessary resources.

Would you push someone out of a plane without ensuring a safe landing?

Yet that’s what many managers inadvertently do. They assign responsibilities and then disappear without making sure the conditions for success are in place – only to reappear after the splat.

Or they stand next to their people the entire time, micro-managing them, and never let them make the jump.

Both of these approaches to delegation have the same effect:  the delegation fails.  It creates a self-fulfilling prophecy that reinforces their attitude that delegating is risky. No wonder they are reluctant to delegate.

Effective delegating is more than assigning responsibility.

Here are 7 guidelines to be confident you are delegating effectively.

1. Plan to delegate.

  • Consider your direct report’s skills, interests, and current workload.
  • Delegate recurring tasks, detail work, attendance at some meetings, and activities that may become part of your direct report’s future responsibilities.
  • Don’t delegate performance evaluations, disciplinary actions, confidential tasks, tasks specifically assigned to you, and sensitive situations.
  • Allow your direct reports some participation in determining what and when tasks are delegated to them.
  • Determine what monitoring should look like based on the complexity of the task and your direct report’s skills and confidence. Don’t disappear, but don’t over-supervise. Hovering is counter-productive.
  • Delegate to the lowest level at which the task can be successfully accomplished. Do not bypass your direct report, but give him or her the authority to delegate the task.

2. Communicate clearly and completely.

  • Be specific, clear, and complete in communicating: What are the tasks, the goals, constraints, what good performance looks like, how progress will be monitored, how performance will be evaluated, when and how results of the task will be communicated you.
  • Get acknowledgement that your direct understands and agrees to the assignment.

3. Grant authority.

  • Grant enough authority to do the job: enough power and control over resources to get the job done.
  • Inform all who will be affected that the delegation has occurred.

4. Provide resources and recognition.

  • Provide all information that is available and relevant; pass on other information as it becomes available.
  • Ensure they have access to the resources needed to be effective.
  • Give public credit when your directs succeed at delegated tasks, but not blame when they make mistakes.

5. Don’t take it back.

  • Require your direct reports to first propose their ideas for solutions to problems rather than just asking you what to do so you don’t end up taking on their work.
  • Do not interfere, undermine, or “take the delegation away” unless your direct is clear that corrective action needs to be taken.

6. Maintain accountability.

  • It should be clear that your direct report has the responsibility for seeing the job well done and the authority to make needed decisions.
  • Remember that the ultimate accountability remains with you.

7. Delegate consistently.

  • Delegate consistently, not just when you are overloaded or when tasks are unpleasant.

A note to those who have been delegated to:

If someone has delegated to you and it’s not working out, try using this checklist as a diagnostic. Is something not in place? Don’t jump out of the plane without making sure you have a parachute and are confident you know how to use it.


27 comments to Would You Skydive Without a Parachute? How to Delegate With Confidence.

  • Jesse, I smiled when I first saw this post and the picture above, because years ago I, too, went sky-diving, and received the same sort of surprise reaction as Roger did! As for delegation, unfortunately, too many people swing between the two extremes you outline above. We can indeed delegate with confidence when we provide our direct reports with the tools and resources needed to successfully do their jobs, including on-going communication and accountibility. Unlike the two extremes of micromanaging or packing a player without a chute and pushing them out of the plane, this solution empowers the direct report while providing foundational support for continue growth. Great post!

  • Hi Sharon, I enjoy imagining you skydiving. :-)
    Thanks for your thoughts on delegating and furthering the conversation.

  • Hi Jesse,

    First, I love how you tell a story that connects me with the concepts you are communicating. Thank you.

    My experience with leaders, entrepreneurial folks in particular, is delegation is a real problem. They can’t let things go. Do you have suggestions for helping reluctant leaders begin the process of delegating.

    Thanks for all you do,


    • Hi Dan,

      Delegating itself can feel like jumping out of a plane for some folks. In that case, they need instructions, encouragement and resources. My guidelines provide the instructions.

      But they also need ongoing support and feedback to keep following the guidelines. I think coaching is a great resource.
      Other thoughts, anyone?

  • Gregg Peters

    Hi Jesse,

    I have seen many times where “Grant Authority” has not been followed. When we don’t grant the authority, or notify others that it has been granted, we set the individual up for failure. There have been occassions where I was not informed of the authority that had been granted to me, but I was left with the responsibility. Definitely places you on an island.


    • I wholeheartedly agree with you, Gregg. Giving someone responsibility without the authority to make the needed decisions is the equivalent of pushing them out of a plane without a working parachute. Thanks for emphasizing this important point.

  • Hi Jesse,

    To add to your reply to Dan’s query, I would add that it’s important to point out to reluctant leaders what they’d stand to gain from delegating appropriate tasks to their employees. Benefits such as helping to build a stronger team by improving their skills/abilities, thereby allowing your organization to accomplish more than if leaders were to keep their employees stagnating at their current skill level.

    Another benefit would be that in delegating certain tasks to their employees, leaders will free up their plate to deal with some of the more wide-scope planning and issues that they often struggle to manage because they spend so much time dealing with these other issues.

    By showing your employees, and yourself, that they can handle these new responsibilities, both employees and leaders can not only feel a greater sense of accomplishment, but they’ll also engender a greater sense of respect for one another.

    Helping reluctant leaders to shift their focus from what ‘power’ they perceive they might lose, to what advantages they stand to gain from delegating work to their employees will help make it easier for them to commit to such efforts over the long run.

    • Great point, Tanveer. The place to start in helping reluctant leaders begin the process of delegating is by showing them how it will specifically benefit them, their team and the company. You have listed some excellent examples of the benefits. Thanks so much for adding to the conversation.

  • Hi Jesse,

    Had to comment when I read the headline, made me laugh. Great post and of course I have some thoughts.

    Delegating as with skydiving as you point out so well can be rather nerve racking to even think about. But once you are out the door (all 7 guidelines confidently taken care of) it should be a blast. Of course as with skydiving it is always a good idea to check in with your surroundings and make sure all is well. Don’t want to land on a power line or wait too long to open you canopy.

    Delegation is wonderful when it works, but can be a disaster if it does not, so although you can go through a whole set of instructions, encouragement and resources which seem to be understood, the good old human factor is still lurking in the shadows. Keeping an eye does not mean not enjoying the ride, just stay aware and understand things can and do go wrong sometimes. If you are not prepared for a problem or you thought it would be OK once you got out the door, it may be your first and last delegated task.

    I totally get Dan’s comment about people (many entrepreneurial folks) not wanting to let go, and your advice about “instructions, encouragement and resources” along with Tanveer points of benefits being big incentives to let go. But sometimes people just don’t want to jump, sure they have their Parachute on, they have had their instructions, have the resources, understand the benefits but, no, they’re not going to do it.

    You could give them a push, that gets them out the door,(drop them in the deep end) but what happens then. One thing I have had success with for that first delegated task or first time delegating a task is to start with a task that is a less natural strength for the giver and more natural (strength), of the delegated. Giving a detail orientated task (when you are not detail orientated) to someone that is detail orientated, is a win win situation.

    Just as you start Skydiving using either a static line, tandem jumps, or with instructors holding onto you during your exit from the plane and subsequent free fall, that first delegated task should be set up for success on both sides.

    • Well said, Simon! A great description of the issues one faces. And an excellent suggestion for how to test the waters in delegating and create a win-win at the same time: delegate a task that plays to the strength of the person you are delegating to and that is not one of your own strengths. Hope you stop by again!

      • M Schak

        Hi Jesse-

        I am currently faced with 2 situations regarding my manager’s inability to effectively delegate. What I would like to do is effectively communicate to him that I feel unappreciated and untrustworthy for seemingly no reason.

        The first situation has to do with his delegating a task I would typically do (and enjoy doing) to someone who is scared to do it and disinterested. In addition to that, I found out from my colleague and not my manager that she was assigned to do these things. We even had a team meeting the day before, and this wasn’t discussed. I understand that other folks on the team should have the skills necessary when someone else is not available, but it felt like I wasn’t told on purpose, which causes paranoia.

        The second situation has to do with a project that I have been managing effectively for the last 4 years. I work with various groups within the organization to complete the project. This year, a different set of people from one group will be working on one portion of the project. I let my manager know that I would call a brief meeting to get them up to speed, and he asked me to do it on Monday, as he will be out of town Tuesday and Wednesday. Does he have to be there? Why can’t I inform these people of the procedures, etc? This makes me feel as though he doesn’t trust me.

        Do you have any advice for me regarding this? Thanks!

        • This is a bigger issue than your manager’s inability to effectively delegate. Much is being assumed and not communicated. You need information on why you were not assigned the task and why your manager feels the need to be present at your meeting. I suggest you request a meeting with your manager, explain you are confused about these situations and ask for feedback. Try to listen with an open mind. It may be there is something you’re not seeing that could help you improve your performance. Or it might be that your manager is not aware of your aspirations. See if you can open up communications, and get more information before you draw conclusions.

          • M Schak

            Thank you for your response, Jesse. I had a conversation with him just now, and we addressed both issues. He is a new manager (only 2 years now), and he does lack good communication skills. He was not trying to go behind my back intentionally, and I asked that in the future he just informs our group of new activities or delegation. He also said that he really doesn’t have to be at the meeting and knows I can handle it on my own. I do like him, and we get along well, but I feel at times that he micromanages and it’s not consistent. I do feel better, but my original perception became my reality. I’m glad I spoke with him. Thanks again for your feedback.

          • Glad to hear that. Sounds like you have more clarity and have set the stage for future conversations when you feel like you’re being micro-managed. Your comments reminded me of this post and thought you might enjoy it, if you hadn’t seen it earlier: http://seapointcenter.com/great-boss/ Best wishes, Jesse

  • Thanks Jesse and Tanveer, I appreciate you and your insights. Best, Dan

  • Great post and great comments.

    As I read the post, I found myself thinking of the scenario that Simon ended his comments – the tandem jump. When delegating the first time, I do think it is critically important to set them up for success. So the first time through might require a “tandem jump”. Even so, there will still need to be an allocation of grace during the cycles of learning for the delegated task(s).
    Thanks so much for sharing such a great metaphor and easy to follow points!!
    Looking forward to more!

  • Hi Jesse – I am forwarding this post to my client who hated his job. His management literally push him out of a plane every day without a parachute and then criticise him for breaking a metaphoric leg! They need to read this! Excellent content!

    • I’m so glad you did, Dorothy. My hope in writing this post was that people would be able to use it as a message to their boss, and that’s why I put the note to them at the bottom. I had originally considered writing this post in the form of a letter someone could pass on to their boss.

      Unfortunately this is too common of an occurrence – being assigned responsibilities without the direction, support and resources needed, (especially the authority). The consequences are damaging all the way around – to the direct report, the boss, and the organization.

  • Great post Jesse, and your guidance on delegating with confidence is concise and easy to follow. You can’t expect people to succeed in delivering on what you delegated if you do not train them or if they are not motivated to do it (most of the time that is a result of number 7).

  • […] a big deal in leadership.  Often it is such a big deal that it can be quite daunting. In her post: How to Delegate with Confidence, Jesse Lyn Stoner (@jesselynstoner)provides seven guidelines for achieving effectiveness in this […]

  • […] Would You Skydive Without a Parachute? How to Delegate With Confidence. (Jesse Lyn Stoner on My Blog) […]

  • Very nice posting. Two thoughts:
    1] Time and time again, I am astounded by how different academia is. Not that it has to be, but currently, it is. The idea that the relationship between a department chair and an “in the trenches” professor is one involving delegation would be completely foreign. Or, even more basic, the idea that one is a “direct report” for anyone is pretty unfamiliar. Academia, in my opinion, can become much better at just about everything by professionalizing the role of leadership — which does of course not simply mean introducing delegation but instead is more like your ‘granting authority’ and ‘providing resources’ points.
    2] Regarding the delegation discussion, I recently challenged a colleague who is an excellent researcher but has relatively little management experience to delegate more. When he asked how he would know if he had actually done it, I told him that he’ll know when he gives a task to someone and doesn’t feel (or, at least, act on) the urge to check up on the person. It’s a big step, but one has to have professional colleagues and then be able to count on them to deliver.
    Thanks again for the posting!

    • Hi Curt,

      It is interesting how many of the issues in leadership are different in academia, especially when viewed from the relationship between the professor and the department chair in higher education, or in elementary education between the teacher and the principal. This different also exists in other professional settings such as in a hospital between the doctor and the hospital administrator or the department head. In these settings, it is almost unthinkable that someone in management would have a say in how the professional practices his or her craft because they do not have the expertise. This is also sometimes the case in some businesses that employ specialized experts, especially in the areas of technology and research.

      However, from an institutional perspective, academia must answer the same questions as all organizations: why do we exist? what purpose do we serve? how are we going to fulfill our purpose? what are our key strategies? how will we obtain and maintain the resources we need? how should we be structured? how will we evaluate our effectiveness, what processes will we use, etc. And at a macro level – how will be make these decisions and how will we engage the minds and hearts of all involved – administration, professors and students (current and former). There are many conversations and decisions that need to occur on an ongoing basis, many of which have a direct impact on the professor.

      And as you point out, at the micro level, within the classroom or lab, professionals need to consider what and how much they are willing to delegate to those who assist them, whether they are doctoral candidates, teaching assistants or even colleagues in joint projects. It sounds like you gave your colleague good advice. Thanks for sharing your thoughts here.

  • Micah Yost

    Great post. Good stuff.

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