A couple of weeks ago, I completed the Leader Assistant Challenge—a transformative experience created by Jeremy Burrows, author of The Leader Assistant: Four Pillars of a Confident, Game-Changing Assistant. Through small, intentional actions, I reshaped how I work, connect, and lead. Each week offered a fresh perspective on leadership, inspiring me to show up with greater clarity, courage, and purpose.
This post captures the mindset shifts, strategic growth, and quiet wins that helped me step into my role as a true strategic partner—not just supporting the mission, but evolving within it.
Week One: Building Habits of Focus, Leadership, and Connection
May 23–29, 2025
Week one of the challenge series is complete, and it’s already made a meaningful impact. Each day pushed me to examine how I work, connect, and lead—stretching me in ways that felt both productive and personal.
Day 1: The Focus Challenge
Turning off distractions for a focused hour was more powerful than I expected. That uninterrupted time helped me tackle my inbox and regain clarity—but more importantly, it reminded me how much small interruptions erode productivity. Practicing sustained focus is now a non-negotiable part of my leadership growth.
Day 2: The Networking Challenge
I haven’t acted on this one yet, but it’s top of mind. Jeremy’s reflection on working “under a rock” resonated deeply. I’m reminded that networking isn’t just a numbers game—it’s about creating a community of shared experiences and support. I’m ready to step out of my comfort zone and connect with fellow assistants for insight, encouragement, and collaboration.
Day 3: The Salary Increase Challenge
While I’m not yet asking for a raise, I’m preparing. This challenge reframed the salary conversation as a professional step—not a confrontation. I’ve started building my accomplishments log and am embracing the idea of advocating for my value with clarity and confidence when the time is right.
Day 4: Leadership Lunch Break
Taking an intentional break to learn and reflect on leadership was incredibly refreshing. I left my desk, unplugged, and let myself absorb lessons about influence and presence. The biggest takeaway? Assistants are leaders. We steer culture, create calm, and contribute in ways that deserve recognition. I plan to build more of these reflective breaks into my routine.
Day 5: Help a Neighbor
Today was all about support. I created a tailored QTC document that sparked an important strategy conversation with our Medical Director—opening the door for deeper involvement and visibility. I also offered help to teammates, proving again that small gestures can spark big shifts in connection and morale.
Final Thoughts:
This first week reminded me that growth doesn’t have to come from grand gestures—it’s found in the daily choices to lead with focus, connect with purpose, and show up with intention. Here’s to continuing this momentum in week two!
Week Two: Protecting Your Energy, Embracing the Little Things, and Growing Boldly
May 30–June 5, 2025
Week two of the Assistant Challenge brought some powerful realizations. From spontaneous chats to boundaries and brave questions, this week invited me to take small—but meaningful—steps toward being more intentional, empowered, and connected in my role.
Day 6: Spontaneous Lunch
There wasn’t time for a proper lunch break today—but the heart of this challenge still landed. As an introvert, I often keep my head down, but I recognize the quiet power of casual connection. I’m holding onto the suggested conversation starters for future moments—a hallway chat, a coffee break, or even a spontaneous Teams call. Every interaction is a chance to understand the people I support just a little more.
Day 7: Little Things Matter
This was such a validating reminder. The routine tasks we often overlook—scheduling, formatting, following up—are actually the foundation of trust and excellence. This challenge reframed the “small stuff” as vital, and reminded me that every detail I handle with care helps leadership shine. It deepens my pride in the work that often happens behind the scenes.
Day 8: Just Say No
Today, I practiced saying “No” with grace. It was a boundary-setting moment that reminded me how empowering it is to protect my time and capacity. Each respectful decline allows me to say “Yes” more meaningfully elsewhere. This challenge helped reframe “No” not as a rejection, but as a form of self-leadership.
Day 9: Deal with Interruptions
Interruptions are a constant challenge—especially when your job is to be available. But I took steps today to regain control: updated notification settings, blocked focus time, and added a status message to reduce the pressure to reply instantly. These shifts, though small, gave me space to do deeper work and think more clearly. My takeaway? Focus is a leadership tool worth fiercely protecting.
Day 10: Ask Your Executive This Question
Whew. This challenge hit me in the gut—in a good way. Asking my executive directly for feedback on how I’m doing feels incredibly vulnerable. I haven’t done it yet, but I’m sitting with it. I know discomfort often signals growth, and when I’m ready, I want to ask that question with courage and openness. The potential to learn, improve, and grow stronger in partnership is worth it.
Final Thoughts:
This week wasn’t about grand gestures—it was about daily courage. Whether it was setting a boundary, sparking a hallway chat, or simply rethinking a routine task, each challenge invited me to lead from where I am. And that’s exactly what I plan to keep doing.
Week Three: Leading Boldly, Protecting Energy, and Cultivating Intentional Communication
June 6–12, 2025
Week three dove deep into leadership mindset, self-care strategies, and strengthening executive partnerships. Each day invited me to rise fully into my role and manage my energy with intention—key steps toward sustained impact and balance.
Day 11: You Are a Leader
This challenge was a powerful call to own the leadership we already embody. It reminded me that leadership isn’t about titles or waiting for permission—it’s about stepping up with courage, clarity, and conviction. As assistants, we don’t just support; we help shape what happens next by leading beside our executives every day.
Day 12: Resist Burnout
Prioritizing my mental, physical, spiritual, and emotional health has become non-negotiable. I’m learning to listen to my energy and give myself permission to pause before hitting a wall. Planning a half-week off next week to recharge at the beach feels like the perfect way to reset and return grounded, focused, and refreshed.
Day 13: Lead with the Ideal Week Calendar
Managing a relatively straightforward schedule allows me to be proactive and thoughtful with time blocks. Still, I see the importance of carving out clear “focus” times for my executive, especially as our organization grows. I’m eager to explore the Ideal Week template and open a conversation about shaping a balanced, strategic schedule.
Day 14: Stop Looking at Facebook
A social media detox challenge was a welcome reminder of how much small distractions add up. Signing out completely helped me regain focus and presence for the day. The bonus tool for managing notifications without falling into endless scrolling will definitely be part of my toolkit moving forward.
Day 15: Check in with Your Executive
Weekly 1-on-1s with my executive have become invaluable. This challenge reinforced the importance of showing up prepared, curious, and intentional in those meetings. These conversations keep priorities aligned, roadblocks surfaced, and communication strong—even during busy seasons.
Final Thoughts:
This week reinforced that leadership starts with owning our influence and protecting our well-being. Intentional scheduling and authentic communication with our executives create space for success. Taking care of ourselves and our partnerships keeps us ready to lead with heart and purpose.
Week 4 Reflection – Assistant Challenge
Theme: Steady Leadership, Grounded Growth
Week 4 of the Assistant Challenge has been a mirror—showing me both who I am and who I’m becoming. It reminded me that being an Executive Assistant is more than mastering calendars, credentialing, and compliance. It’s about leadership at its most human level: attitude, accountability, rest, self-awareness, and strategic focus.
Day 16: Lead With Your Attitude
This challenge affirmed something I deeply believe: our attitude is our leadership signature. In a role where I support a Medical Director and often wear multiple hats, the emotional tone I set matters. I strive to be steady, warm, and solution-oriented—not just helpful, but hopeful. The real leadership test comes in how I show up when the inbox is bursting or the pressure is silent but heavy. This day reminded me to check in with myself before I check off the next task—and to lead from a place of calm intention.
Day 17: Were You Wrong? Admit It.
Owning my mistakes is never easy, but it’s transformative. This challenge brought me back to a moment when I assumed wrong and reacted publicly. Apologizing, sincerely and privately, not only repaired the damage—it built deeper respect. I’ve learned that accountability is the true currency of leadership. It’s not about being perfect, but about having the courage to make things right.
Day 18: Practice Resting
Rest isn’t a reward—it’s a requirement. After a beach trip with my family, I came back lighter, more centered, and with a new understanding that peace is productivity. This challenge reminded me that recovery isn’t just for weekends—it should be part of my rhythm. I’m more effective, more present, and more creative when I’m not operating on empty.
Day 19: Characteristics of a Good Assistant
This challenge turned the spotlight inward. The three traits I’m actively developing—patience, calm under pressure, and being others-centered—aren’t checkboxes, they’re daily disciplines. Each one invites me to pause, breathe, and stretch beyond my habits. Growth isn’t about harsh self-critique; it’s about compassionate self-honesty and the will to improve.
Day 20: 5 Steps to More Time, Energy, and Success
This challenge landed like a blueprint for the leader I’m becoming. I’ve started tracking distractions, protecting my focus, and prioritizing high-value work that aligns with my future goals—like a Chief of Staff role. Delegation, system design, and empowering others are no longer just strategies—they’re declarations of how I lead. This is how I multiply impact without multiplying burnout.
Final Thought:
This week has been a blend of reflection, recalibration, and renewed commitment. I’m reminded that leadership is not about being the loudest or most visible—it’s about being intentional with your energy, honest about your mistakes, and brave enough to rest and reset.
I’m not just doing the work—I’m becoming the woman who leads it well.
Week 5 Summary: Learning, Leading & Letting Go
Day 21 – Be Grateful
I reflected on my deep-rooted calling to serve, especially in the recovery field. While administrative tasks may be behind the scenes, I've embraced their ripple effect on patient care. I acknowledged the challenge of wanting recognition but are learning to lead with humility and ground yourself in gratitude—even when your efforts go unseen.
Day 22 – Be Confident
I recognized that confidence isn’t about having no fear—it’s about taking action despite fear. Each time I anticipate needs, hold hard conversations, or support my leader with intention, I build confidence and step more fully into my leadership identity.
Day 23 – Ask Clarifying Questions
I've learned that asking clear, strategic questions—especially working with a Medical Director who’s still developing leadership skills—is essential. Clarifying expectations early helps me go from just being helpful to becoming indispensable.
Day 24 – Be Willing to Do (Almost) Anything
I express pride in being someone my team can count on. For me, real leadership is found in stepping in without needing to be asked—and saying, “that’s not my job” just doesn’t align with my mindset.
Day 25 – Outsource Your Job
Still early in my role, I'm learning which responsibilities are truly mine—and which I've assumed out of habit. This reflection helped me see the value in delegation, not as a weakness, but as a smart strategy for growth. I'm beginning to ask what truly requires my hands—and what could be done better by someone else.
Week 6
Day 26: Clean Your Desk (6/27/25)
As someone who treats clutter like a personal offense, I was tempted to reply, “Already done. Yesterday. And the day before that.” But in the spirit of team participation (and peak productivity), I gave my workspace a quick audit.
- Gave the monitor a spa day—because clear screens lead to clear decisions.
- Loose papers were handled accordingly: filed, recycled, or given a dramatic farewell wave.
- The snack drawer underwent a full audit. Categories established. Contraband removed. Salty now lives in harmony with sweet.
- Retired an army of pens that lost the will to write. Sticky notes that stuck around too long? Gone.
- Found a fossilized chocolate bar from 2024. It has been... respectfully laid to rest.
- Rehomed my daily essentials with the precision of a relocation specialist:
“Phone? Front and center. Keys? You've earned drawer duty. Lip balm? You’re in charge of morale.”
The truth is, a tidy desk isn’t just about aesthetics—it’s about walking into your space and feeling on point before your first email even loads. It’s like giving your brain a standing ovation before the workday begins.
Even for someone who thrives on order, it was a reminder: your environment reflects your mindset. And starting the day with a clear desk? It’s like telling chaos, “Not today, Satan.”
Here’s to keeping the energy high and the paper clutter low. Efficiency looks good on us.
Day 27: Propose Solutions (6/30/29)
As an Executive Assistant to a Medical Director in a dynamic rehab and behavioral health setting, I’ve learned that both open and closed questions have their place—especially when navigating credentialing, compliance, provider support, and admin ops.
That said, today’s challenge was a timely reminder to lead with more solution-oriented communication.
I typically use open questions to get clarity on preferences or when I’m gauging direction:
“How would you like to approach this case review?” or “What’s your preference for onboarding the new provider?”
But today, I shifted gears and brought recommendations instead of questions.
Instead of asking, “Should I prep the Competency Validation Form now or later?”
I said, “I’ve pre-filled the Competency Form and can send it for your review by noon—unless you'd prefer I hold off until after rounds.”
Instead of “Do you want to follow up with HR or should I?”
I offered, “I’ll loop in HR regarding the onboarding checklist unless there’s a specific point you’d like to address directly.”
This approach made our day smoother and gave my executive fewer decisions to make—which is always a win in a setting where brainpower is constantly taxed.
So, while I’ll still use questions strategically when needed, I see the value in leading with well-thought-out solutions.
Day 28 Shadow Your Executive (7/1/25)
The last time I attended a meeting solely to learn was during one of our monthly provider meetings. While I typically support with logistics and follow-ups, I used that session to actively listen and deepen my understanding of how clinical updates, compliance, and team dynamics play out across departments.
This week, I noticed my Medical Director is scheduled for a call with our billing liaison to discuss recent changes in payer requirements and preauthorization workflows. I’m not required to attend, but I’d like to ask if I can sit in—partly to take notes, but mainly to get a better grasp of how those conversations shape our internal processes and impact patient flow.
I plan to ask:
"Would it be alright if I sat in on the billing update call this week? I’d love to better understand how these payer discussions influence our prior auth process and overall operations. It’ll help me support you and the clinical team more efficiently."
This challenge reminded me that even meetings I’m not assigned to can be great learning opportunities if approached with the right intention.
Day 29: Surprise Your Executive (7/2/25)
This one made me smile—my Medical Director and I are cut from the same cloth when it comes to keeping things tidy. His desk is usually just as neat as mine, so there’s rarely a need to straighten anything up. But I definitely appreciate the reminder to look for small ways to support while staying behind the scenes.
As I prepared for a short bereavement leave, I’ve been focusing on leaving things in great shape—files organized, tasks up to date, and everything labeled clearly so he can function without a hiccup while I’m out.
Day 30: Find a Hobby
Like many of us, I’ve poured a lot of myself into my work—especially in my role as an Executive Assistant. I understand how easy it is to slip into the “always-on” mindset and unintentionally let the things that bring you personal joy fall to the side.
As I prepare to take bereavement leave, I’ve been reminded how important it is to create space for the things that restore me. One of those things is writing—it's a quiet, creative outlet that lets me reflect, dream, and decompress. I’ve dabbled here and there, but I’m committing to carving out more intentional time for it. Whether it’s journaling, working on personal projects, or simply putting thoughts to paper, writing has always been my space to breathe.
Thank you for this challenge—and really, for all of them. They’ve helped me reconnect with the “me” behind the job title.
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