Happy spooky season, readers! Today’s post is exploring the slightly spooky side of leadership, using your strategic leadership skills.
For some of you, “strategic” may not be a strength or leadership skill you immediately identify with, but I’m willing to bet you are using it more often than you think. In our Res Life roles, we encounter countless challenges, frustrations, and energy vampires competing for our attention. By this point in the semester, routines are beginning to settle, which also means we are starting to notice the issues around us… the process we thought we fixed, a new facilities challenge, emerging resident concerns, or a team dynamic that suddenly needs our attention.
Before long, our minds begin mapping out every problem we need to solve and how we are going to do it. Because once we fix everything, there will never be another problem again, right?
Wrong.
There will almost always be another issue, another process to improve, or another emergency that is not really an emergency asking for our attention. The question is not whether we care enough to respond. Many of us work in helping professions because we care deeply about serving others, supporting our communities, and solving problems.
The more difficult question is, “Where should we focus our energy, influence, and leadership when there are so many things we could fix?”
“Is this the hill you’re willing to die on?”
I don’t think of this question literally because, thankfully, work is not that serious. Instead, I think of it as an invitation to take inventory of our capacity before taking on another task, challenge, or responsibility.
For many of us, everything can feel important because we care deeply about our students, staff, and communities. We want to improve processes, support our teams, address inequities, and create meaningful change. But not every issue needs our immediate attention, and not every problem is ours to fix.
Read that again.
As a recovering overachiever and people pleaser, I have had to learn to consider my bandwidth and be more intentional about where I focus my energy and time at work. As I have moved through my career, I have learned the value of being strategic about what I take on, what I advocate for, and sometimes, what I choose to let go.
Strategic leadership has changed how I show up in professional spaces and the lens through which I view challenges. Instead of immediately asking, How do I fix this? I am learning to ask questions like: Does this need to be fixed right now? Is this mine to fix? Where do I actually have influence? And is this where I want to spend my limited time and energy?
The goal of this post is not necessarily to solve your problem (sorry about that!), but to give you a few tools for deciding which tasks, challenges, and hills are worth taking on. We can care about many things while still choosing what matters most right now.
Tips for using strategic leadership:
- Look for patterns: Take a step back and consider whether the issue is connected to a larger or recurring challenge.
- Consider your options: Identify two or three possible ways to respond and think about the benefits and challenges of each.
- Decide what needs your attention now: Ask yourself what is urgent, what can wait, and what will make the greatest difference.
- Invite others to help: You do not have to solve everything alone. Consider who may have the knowledge, relationships, or skills to help move the issue forward.
Let’s put these tips into action! Think of the quiz below as a personal check in to help you decide whether a challenge is truly your hill, what options you have, and where your energy may be most useful. And no, this will not be graded!
Choose Your Hill: A Strategic Leadership Mini-Quiz
Think about one challenge currently taking up space in your mind. Keep it in mind as you work through these questions.
1. What is really happening here?
- What is the actual issue?
- Is this a one-time problem or part of a larger pattern?
- Who is affected?
2. Is this your hill?
- Does this need attention right now?
- Do you have influence over the situation?
- Is this where your time and energy are best spent?
Note: You may not have all the answers right away to know if this is indeed your hill. Talk it through with a trusted peer or supervisor. They can help you clarify what needs to be addressed and how you are defining the problem.
3. What are your options?
Consider two or three possible ways to respond. Could you take action, wait for more information, involve someone else, or try a smaller first step?
4. What is your next move?
Choose the response that fits best:
- Push: Take action.
- Pause: Gather more information.
- Ask for help: Involve someone else.
- Let it go: Release what is not yours to solve.
Whatever you decide, remember that strategic leadership is not about solving every problem. Sometimes the most strategic choice is knowing when to push forward, pause, ask for help, or let go. Enjoy the strategic thinking process, give yourself grace, and remember it’s almost “let’s circle back to this after the holidays” season.



