CEO's Corner: Master The Art Of Working With An Assistant (... so you can get more done in less time)
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Written by:
Filip Pesek
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Struggling to work effectively with your assistant? You’re not alone. Many CEOs feel bogged down by endless demands—late nights, constant emails, and a to-do list that never seems to shrink. Even with an assistant, it’s tempting to micromanage or take tasks into your own hands because, let’s face it, it feels faster that way.
But here’s the hard truth: the problem isn’t your assistant—it’s how you’re working with them.
For years, I, Filip, made that same mistake. I treated my assistant as a task-doer instead of a partner. But everything changed when I realized that an assistant can be so much more—a force multiplier for my productivity, a partner in leadership, and a key to reclaiming my time and focus. The shift required effort: building trust, creating intentional systems, and changing how I approached delegation. The result? I now save over 60 hours a month and feel like a better leader than ever before.
If this sounds familiar, don’t worry—it doesn’t have to stay this way. Mastering the CEO-assistant dynamic can transform how you lead, work, and live. This article will walk you through actionable strategies to unlock the potential of this partnership, helping you achieve more, stress less, and lead with confidence. Let’s get started.
Table of Contents
Building a Successful Partnership With Your Assistant (An Example)
To showcase what makes an assistant relationship truly exceptional, let’s explore a hypothetical scenario through three levels of engagement: bad, good, and great.
Hypothetical Project Scenario: Launching a Corporate Social Responsibility (CSR) Campaign
Your company is rolling out a new Corporate Social Responsibility initiative focused on supporting local communities. As the CEO, this initiative is a top priority for enhancing the company’s brand and employee engagement. The campaign involves:
- Identifying and partnering with a non-profit organization aligned with your company’s mission.
- Organizing a kick-off event to announce the partnership to employees, stakeholders, and the media.
- Developing a communications strategy to highlight the campaign across social media, press releases, and internal channels.
- Setting up employee volunteer opportunities to encourage participation and track engagement metrics.
Now, let’s examine how this project would unfold with a bad, good, and great assistant dynamic.
What a BAD Assistant Dynamic Looks Like 👎
- Kickoff:
You attend the initial strategy meeting and leave with a long to-do list. You intend to brief your assistant, but days pass before you hurriedly provide them with fragmented details. - Task Assignment:
You ask your assistant to research non-profits without providing specific criteria or priorities. Tasks like event planning and communications strategy remain on your plate because you feel it’s easier to handle them yourself. Your assistant feels unsure of their role in the project. - Information Flow:
When challenges arise—such as a non-profit partner requesting revisions to the campaign scope—you must intervene because your assistant lacks the context or authority to handle it. Communication feels disjointed, and bottlenecks slow the project.
Outcome: The campaign launches late, with little impact. Employees and stakeholders notice the lack of coordination, and the initiative feels rushed and uninspired.
What a GOOD Assistant Dynamic Looks Like 👍
- Kickoff:
After attending the strategy meeting, you brief your assistant during your regular one-on-one session. You provide clear objectives, priorities, and deadlines. - Task Assignment:
You delegate specific tasks, such as shortlisting potential non-profits and coordinating initial outreach. You also involve your assistant in event planning but retain oversight of key decisions like messaging and vendor selection. - Information Flow:
You cc your assistant on emails and ensure they’re part of relevant conversations. When challenges arise, they bring solutions for your approval, keeping the project moving.
Outcome: The campaign launches successfully, with positive feedback from stakeholders. While the execution is solid, the project required a significant amount of your time and oversight.
What a GREAT Assistant Dynamic Looks Like 👑
- Kickoff:
Your assistant attends the initial strategy meeting in your place and takes detailed notes. They return with a summarized plan, including key decisions for your approval and a suggested action plan. - Task Assignment:
Your assistant takes full ownership of the project. They research and select non-profit options aligned with your company’s mission, schedule meetings with top candidates, and present you with a recommendation. They independently coordinate the event, managing logistics, vendor negotiations, and a communications strategy. - Information Flow:
Your assistant keeps you updated on progress through concise weekly updates. They handle challenges autonomously, escalating only high-priority issues. The project tracker they’ve shared provides real-time visibility into milestones, ensuring you’re always in the loop without needing to micromanage.
Outcome: The campaign is a resounding success, praised by employees, stakeholders, and the media. Your assistant’s proactive leadership allows you to focus on high-level strategy and other priorities, knowing the initiative is in capable hands.
The difference between a bad, good, and great assistant dynamic highlights one undeniable truth: the success of the CEO-assistant relationship hinges on trust, access, and alignment.
A bad dynamic creates inefficiencies and frustration, while a good one provides support but still requires significant oversight. It’s only in a great dynamic-where the assistant operates as an empowered extension of the CEO-that true impact is achieved.
This shift doesn’t happen overnight; it requires intentional mindset shifts, clear communication, and the right systems in place.
As we move forward, we’ll unpack the tools and strategies needed to cultivate this kind of synergy, ensuring both CEO and assistant can thrive in their roles while driving organizational success.
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The CEO’s Perspective: Why the CEO-Assistant Relationship Matters
It all changed when I stopped seeing my assistant as an administrative tool but rather started seeing her as a strategic partner. This shift wasn’t merely about delegating more—it was about aligning her role with my priorities and empowering her to take ownership of key areas in my day-to-day operations.
The Vision: A Seamless Partnership
A great CEO-assistant relationship isn’t just about productivity; it’s about creating a seamless partnership where both parties operate in sync. For me, this meant my assistant needed to understand my goals, decision-making style, and priorities so she could proactively support me. It wasn’t just about freeing up my time but amplifying my impact.
The CEO’s Role
Perhaps the most important lesson I learned was that the success of this partnership starts with me. My assistant can only be as effective as the systems and access I provide. For instance, I had to:
The Benefits of a Strong Partnership
As soon as we laid this foundation, the benefits were undeniable. I started freeing up more focus for high-value tasks, while my assistant felt empowered on what decisions to make and initiatives to take. This wasn’t just about efficiency—it allowed both of us to thrive in our roles.
But this did not come without its own fair share of difficulties, and there was quite a bit to learn on both sides. Neither is the mindset shift restricted to CEOs; it requires effort and adaptation on both sides of the partnership.
Actionable Tips and Systems for a High-Impact Working Partnership With An Assistant
Building a strong CEO-assistant relationship requires more than just delegation. It’s about creating systems, building trust, and empowering your assistant to be proactive. I’m going to share the strategies that worked for us:
1. Weekly Check-Ins for Effective Communication
Consistency is key. My assistant and I schedule weekly check-ins to review priorities, updates, and challenges. These meetings create a rhythm of communication and help us stay aligned. Even though I’m not a fan of meetings, this one exception has been worth it.
2. A Master Project List for Structuring Workflow and Tasks
We rely on a centralized project list-an organized spreadsheet that tracks every task and project. This list has three tabs: Active Projects, Archived Projects, and Recurring Projects. Each task includes details like priority, due dates, and status. This system ensures nothing falls through the cracks and gives both of us a clear overview of ongoing work.
3. Delegate with Clarity
One of my biggest mistakes was assuming my assistant could read my mind. Now, I make a point to clearly communicate the outcome I want, along with any relevant context, as outlined in this article by Forbes. This not only saves time but also allows her to take ownership of tasks with confidence.
4. Use Color-Coded Systems
To streamline communication, we’ve implemented a simple color-coding system for the project list. New information is highlighted in red, updates from me are in blue, and completed items are marked black. This visual approach makes it easy to focus on what’s most important at a glance.
5. Empower Proactive Problem-Solving To Build Decision Making and Trust
One of the most valuable shifts in our partnership was empowering my assistant to make decisions independently within predefined boundaries. For example, she knows which types of emails she can respond to on my behalf and when to escalate something for my input. This level of autonomy has been a game-changer.
6. Record Key Meetings
We record certain meetings to ensure nothing gets missed. My assistant uses these recordings to create detailed action items, which she adds to our project list. This has been invaluable for maintaining accuracy and accountability.
7. Build a System for Success
From day one, I tasked my assistant with building a “playbook” for her role. This document includes workflows, preferences, and best practices—a resource that not only improves her efficiency but also lays the foundation for future assistants to step in seamlessly if needed.
These strategies didn’t just help us work better together-they fundamentally changed the way I approached delegation and leadership. In the next section, we’ll discuss how to overcome common challenges that CEOs and assistants face when trying to optimize this relationship.
Pro Tip:
Be a teacher and mentor to your assistant, fostering their professional growth alongside completing tasks. Don’t just delegate work—take the time to explain the purpose and context behind what you’re doing and why it matters. Encourage them to observe client meetings, team discussions, and other relevant interactions to better understand the nuances of your role and the bigger picture. By CC’ing them on emails or sharing updates about ongoing projects, you’ll help them stay informed and aligned, empowering them to contribute more effectively and grow into a stronger support for you and your team.
The Assistant’s Perspective: Building a Thriving Partnership
From the moment I, Anna, started my first day as an assistant to a CEO client at DonnaPro, I knew this would be more than just keeping schedules and answering emails. To truly support the CEO client I was assigned, I had to understand not only his tasks but also his goals, priorities, and leadership style. This wasn’t about getting things done; this was about getting the right things done.
Understanding the CEO’s Needs
The first step in building our partnership was gaining clarity on his expectations. This didn’t happen overnight. It took consistent conversations and feedback to figure out how I could add the most value. I quickly learned that my role wasn’t just about executing tasks but also about anticipating needs and solving problems before they reached his desk.
Proactivity Is Key
One of the most important lessons I’ve learned is the value of being proactive. For instance, rather than waiting for him to ask me to schedule a meeting, I’d review his calendar weekly and suggest ways to optimize his time. I’d show up with solutions if there was some form of continuity or pattern, like double-bookings or back-to-back meetings without any breaks in between, rather than wait for instructions.
Building Trust Through Reliability
Trust is the foundation of any successful partnership, and it had to be earned. I made it a priority to always follow through on commitments, meet deadlines, and communicate openly. When I didn’t know something, I asked. When I made a mistake, I owned it. Over time, this transparency built a level of trust that allowed us to work seamlessly together.
Tools and Systems That Worked for Us
To stay organized and ensure nothing slipped through the cracks, we implemented several tools and systems that have been game-changers. Here are our top suggestions:
- A Centralized Task List: Keeping everything in one place—whether it was in a shared spreadsheet or a project management tool—ensured we both had visibility into ongoing priorities.
- Color-Coding Communication: This simple technique made it easy to highlight updates, new information, and completed tasks.
- Regular Feedback Loops: Weekly check-ins gave us the opportunity to discuss what was working, what wasn’t, and how we could adjust.
Creating Space for Feedback
Feedback goes both ways. I appreciated that my CEO was open to hearing my perspective, whether it was about improving workflows or identifying inefficiencies. This openness made me feel valued and motivated me to bring my best to the role every day.
Together, we created a dynamic partnership, and in the next section, we’ll dive into actionable tips and systems that made all the difference.
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Overcoming Common Challenges in the CEO-Assistant Working Relationship
Even with the best systems and intentions, challenges are inevitable in any working relationship. Here are some common hurdles CEOs and assistants face—and how we overcame them:
Challenge 1: "I Can Do It Faster Myself"
This mindset held me back for years. I realized that while I could do many tasks faster in the short term, I was sacrificing long-term efficiency and scalability. The solution? Delegation as an investment. Training my assistant on tasks I initially thought were “too complex” saved me countless hours in the long run.
Challenge 2: Lack of Clarity on Roles and Expectations
In the beginning, there was often confusion about what my assistant could or couldn’t do. To address this, we created a delegation framework that outlined responsibilities, boundaries, and decision-making authority. Regular check-ins also gave us space to clarify priorities and adjust as needed.
Challenge 3: Trusting Someone Else with Sensitive Information
Trust doesn’t happen overnight. I started by giving my assistant access to less critical tasks and gradually expanded her scope as she demonstrated reliability. Transparency and open communication were key. Over time, I learned to trust her with even the most sensitive aspects of my work.
Challenge 4: Misaligned Priorities
At times, we found ourselves working on tasks that didn’t align with overarching goals. To fix this, we implemented a weekly review process to ensure our efforts were focused on the right priorities. This simple practice kept us aligned and minimized wasted effort.
Challenge 5: Communication Breakdowns
Miscommunication can derail even the best partnerships. To combat this, we established clear channels for different types of communication—whether it was a quick Slack message for minor updates or scheduled calls for more in-depth discussions. Additionally, our color-coded project list became a single source of truth for tracking progress.
Challenge 6: Resistance to Feedback
Feedback is essential for growth, but it can feel uncomfortable at times. We both committed to creating a culture of constructive feedback, where we could openly share what was working and what wasn’t. This mutual openness strengthened our partnership and allowed us to continuously improve.
By addressing these challenges head-on, we built a partnership that is both resilient and highly effective. In the final section, I’ll share some parting thoughts on how you can take the first steps toward mastering your own CEO-assistant relationship.
Conclusion: A Transformative Partnership
Mastering the art of working with an assistant isn’t a one-time effort—it’s an ongoing commitment to collaboration, communication, and mutual growth. This dynamic partnership has the potential to transform your leadership, productivity, and overall impact as a CEO.
Take a moment to reflect on your current assistant relationship. Are you providing the trust, tools, and clarity your assistant needs to succeed? Have you empowered them to take ownership of their role? Most importantly, what’s one thing you can change today to make this partnership more effective?
Your assistant isn’t just a support role—they’re your secret weapon. When you invest in this relationship and commit to building it, the rewards are profound. Greater focus, enhanced efficiency, and a thriving partnership that uplifts your entire organization are just the beginning.
FAQ
How do weekly check-ins enhance the CEO-assistant collaboration?
Weekly check-ins create a consistent rhythm for reviewing priorities, addressing challenges, and adjusting workflows, ensuring both CEO and assistant stay aligned and proactive.
What is a Master Project List and how does it streamline task management?
A Master Project List is a centralized tracker (with tabs for active, archived, and recurring projects) that logs priorities, due dates, and status, preventing tasks from slipping through the cracks.
How can I build trust and delegate more effectively to my assistant?
Start by granting access to your calendar and inbox for low-risk tasks, provide clear expectations, and gradually expand their scope as they demonstrate reliability—this fosters autonomy and confidence.
How can a virtual executive assistant boost my productivity?
A virtual executive assistant from DonnaPro handles email management, scheduling, research, and routine operations, freeing you to focus on strategic leadership.
Which tasks can I delegate to an executive virtual assistant to maximize my efficiency?
You can delegate calendar coordination, travel planning, meeting preparation, client follow-ups, and data entry to an executive virtual assistant. Discover our full range of virtual assistant services designed for CEOs.”
