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"Mr. Arave, I'm done with my list. What can I do next?" Alex asked me. I stood center stage with the strike list in my hand, my guide for coordinating 60 students and 12 parents in dismantling our set for White Christmas. Little did I know this experience would teach me vital delegation skills I'd later use in my career in higher education administration—skills that would save me countless hours and help me build stronger teams.
After closing night of a theatre performance, the cast and crew stay late and dismantle everything in a tradition called "strike." I had participated in these for a decade before needing to lead one. There were two things that made this particular strike unique:
The Challenge of Delegation This experience taught me a fundamental leadership skill that would later prove essential in my professional career: the art of delegation. In this article, I'll share how I learned to delegate effectively, the mistakes I made along the way, and a framework you can use to master this critical skill yourself. Running a smooth strike is almost as much organizational work as it takes to direct a show, especially with a group this big. The only way to really get it done is to delegate. After an exhausting 2-and-a-half-hour musical for the last three nights, everyone was eager to get out as soon as possible. There is an urgency and laziness that can be a challenge to lead. Without a plan, it can quickly turn into "too many cooks in the kitchen," and suddenly three-quarters of the cast is sitting down and chatting while the others are getting everything put away. Having experience in this area and knowing what needed to be done, it was easy to make the transition into a leadership role by delegating tasks so they were completed efficiently and effectively. Outside of this theatre context, delegation of tasks hasn't been so easy for me. According to a Harvard Business Review study, leaders who effectively delegate experience 33% less burnout and their teams report 28% higher engagement. Yet the same research found that 78% of leaders struggle to delegate effectively, citing concerns about quality control and time investment. Why Mastering Delegation Transforms Your Leadership When I finally began delegating effectively, three things happened:
Perhaps most surprisingly, relationships improved as trust deepened in both directions. Delegation is a skill that can be learned. Like any other higher-level skill, developing it takes some unlearning. In professional settings, we are asked to do “the work”. In higher education admissions, “the work” is a combination of:
This is a set of skills that is developed through training and experience. As we develop these skills and become confident with them, we have an opportunity to be promoted or take on a leadership role. These roles tend to be filled based on hight performance of “the work” like the skills mentioned above or whatever advanced skills are required for the entry level. While “the work” provides the context for the leadership role, leading and managing is a very different set of skills that need their own development. Delegation is one of them. Quick Delegation Self-Assessment Ask yourself these five questions to identify your delegation blind spots:
If you answered "yes" to three or more questions, you likely have significant opportunities to improve your delegation approach. The Leadership Learning Curve There are lots of hard lessons when getting into a leadership position, even if you have experience. Taking on a new role will have a learning curve, especially if you're new to the institution or company. Before you can lead, you'll need to embrace and understand:
Getting into my first director role, I understood that delegation was necessary. So, I got to work assigning people tasks. I was killing it in assigning tasks. There was one problem: assigning a task is like expecting that my alarm is going to get me out of bed in the morning. Just as the alarm is a reminder of what to do, so is an assigned task. Delegation doesn't work unless the tasks get done. No matter how I assigned the tasks, it was hit or miss whether or not they were accomplished. The process was inconsistent at best. Inconsistency can be detrimental to building a team. In a situation like this, it's very easy—and in some work environments, supported—to put the onus on the employee. Telling myself and superiors that I assigned the task and it's up to the employee to figure it out and get it done. This is easy because it removes the responsibility from me and puts it elsewhere. As a teacher, I saw this happen quite a bit. Teachers absolving themselves because the students failed to pick up and retain the information without consideration of the students' learning styles, knowledge base, or social supports. Calling this out doesn’t absolve the employee, or the student, from the responsibility of their employment or education. In an ideal world, this is a two-way street where the supervisor and the employee meet each other in the middle and develop a path to success together. This is ultimately what I want to accomplish, but like so many ideals, it felt like a distant abstract concept without any concrete steps to get there. As much as I like to hold on to an ideal, if I can't make some semblance of it work in real life, then I'm left living a fantasy. Remaining frustrated in my daily work, and wondering why what I was doing wasn't working consistently. I had to figure out how to reach that balance between meeting someone where they're at and keeping them accountable to the work required of them. Common Delegation Mistakes One of the frustrating parts of learning any new skill is the mistakes that inevitably come with the learning process. No matter how many mistakes I make, I am somehow still surprised when I make them, especially after I think I have a hold of what I'm doing. Despite having delegated in the past, because it is a process driven by people, it is slightly different every time I need to do it. Here is a list of mistakes that are common when learning how to delegate, or more specifically, mistakes that I made while learning how to delegate:
Working through all these mistakes multiple times, I learned that delegation is not a one-and-done sort of skill but something that is consistently adjusted with the dynamics of the team and the work. Alongside learning to delegate, I had to learn how to give myself the grace to be flexible in my approach. Despite the mistakes I made, there were some successes with delegation that gave my staff confidence in their own skills and our work together as a team. A Framework for Effective Delegation "If you want it done right, do it yourself." This old saying captures the burden many of us feel when asking for help or putting responsibility on someone else. I have a hard time asking someone else to do something when I am pretty capable or could do a better job. When a task is being done that I feel I could do better at, I have a tendency to nudge my way in. I struggle to sit still if I think I can do better. This makes it hard for me to let go, to provide someone else the opportunity to do the work and develop the skills. More so, this behavior tends to take on a burden that increases unnecessary stress and leads to burnout. Part of leading is developing a team and recognizing that a team is capable of more than the individuals who make up the team. The only way to get to that point is the delegation of tasks to work together. Lack of delegation will prevent you from developing necessary skills that will prepare you to move forward. Train for delegation. Train for your replacement. I had to learn to let go of my own ability and create a structured plan that can help me relieve tasks to others in a supportive and collaborative way:
Simple Delegation Template For each task you delegate, clarify these five elements:
I keep this as a simple checklist in my notes app and review it before delegating any significant task. The Power of Structure Of this process of learning how to delegate, I have found one section that has become incredibly valuable for me: Structure—for a long time, I pushed against structure, finding it too constraining. As a young professional, I enjoyed the "complete creative control" of making my own decisions once given the assignment. I have mistaken again and again in thinking everyone is wired that way. Structure doesn't have to mean lack of freedom but more direction. As a leader, that aspect of the job is often in the title "Director of Admissions"—somehow I was missing that piece. When I reflected on how I took on a project, I realized I was providing my own structure, much of which was taken from my days producing theatre. I saw that part of the delegation process is to provide enough structure that gives staff enough room to know where and how to make decisions so they aren't lost in the project itself. One of my favorite examples of delegation structure is Tom Sachs' studio manual "10 Bullets". It's a set of principles that guide how his art studio operates, covering everything from maintaining tools to communication protocols. The bullets include directives like "Always Be Knolling" (organizing tools and materials at right angles), "Keep a List" (document everything), and "Sacrifice to Leatherface" (admit mistakes immediately).
When going through these bullets for the first time, they felt harsh and like something I would never want placed upon me. But as Jocko Willink preaches, discipline is the foundation for freedom. Creatively, when we have boundaries to push against, they provide a leverage point for being able to be more creative.
It's similar to pushing water through a hose. The water holds potential energy, but the hose allows you to turn it into targeted energy. The real trick behind this is we can't just adopt Tom Sachs' Ten Bullets and call it good. The structures that work for me and my team are going to be different from what works for you and your team. To develop a structure for support, we each need to experiment and weed things out. The good news is there are lots of things to steal from to give us a starting point. This is where both Pablo Picasso and Austin Kleon's advice comes in handy. Steal the things that make sense, and play with them to see if they actually work. I loved the idea of Tom Sachs' 10 Bullets so much that I created my own. I even made a little book. Some of the bullets stuck and some of them didn't, but the exercise was solid. It reinforced the idea that there's no answer; it's all just trial and error until you come up with a solution that works for you. This alleviated the pressure I felt when solutions I had come across didn't work for me. Putting Theory into Practice Recently, in two very different circumstances, I helped two of my younger staff take the lead on an event our office hosts. For the first event, I provided minimal structure, leaving her to do much of the work on her own and figuring out how to do things. This ended with the staff needing to pick up where balls were dropped, not because she deliberately dropped them but because she didn't know which balls were in the air. Despite her involvement in past events, she didn't keep track of how the event was run. Never having led an event herself, she didn't know what it took to lead others up to and through an event. The event worked out fine; we repeat the events every year, so it's more or less taking what we did the year before, making some minor adjustments, and then executing. Learning from this experience, I went about creating the necessary structure that would make delegating the next event easier. One of the problems that we run into with collaborative events is that the collateral for the event (schedule, meeting notes, attendee list, campus partners, etc.) ends up in different people's digital filing systems. This made it hard to reference the next year due to turnover or forgetting what we did. I created a shared "events" channel in our office's Microsoft Teams. This allowed campus partners not in our Team to have edit access to the folder and anything we put inside. Having one collaborative location made managing the event easier, and now that everything is in one location, we'll be able to reference it next recruitment cycle and not have to reinvent the wheel. The other major structure change I made was asking the staff member to work alongside me on leading the event. This walked them through the process, seeing how I did things, and giving them the autonomy to complete tasks on their own. By working alongside my staff member (step 5: Provide support and resources), I was able to demonstrate clear expectations (step 4) while building trust in her abilities (step 2). The shared Teams channel created the structure needed to monitor progress (step 6) while allowing for reflection and adjustment (step 7). Due to this tag-team approach to managing the event, we ended up naturally completing the steps in the delegation process, resulting in a successful event and a team member who now feels confident taking the lead next time. When done right, delegation isn't just about getting tasks off your plate—it's about developing your team, building mutual trust, and creating systems that make everyone more effective. Start small, be patient with yourself and your team, and remember that becoming an effective delegator is itself a skill worth developing. Get more like this directly to your inbox
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