The most transformative shift I've made as a 4x founder is viewing my Executive Assistant not as an admin resource, but as a strategic partner in the business. This mindset completely changes the game. In the fast-paced logistics and 3PL world, decisions often need to happen quickly. When I first started Fulfill.com, I made the common mistake of using my EA simply for calendar management and travel arrangements. What I discovered through scaling multiple businesses is that EAs typically have exceptional institutional knowledge, emotional intelligence, and problem-solving abilities that remain untapped when we limit their role. My advice? First, be intentionally transparent. Share your priorities, decision-making frameworks, and business objectives regularly. I've found my EA makes dramatically better decisions when understanding the "why" behind my thinking. At Fulfill.com, my EA isn't just managing my schedule – they're making judgment calls about which eCommerce partners or 3PL providers deserve priority attention based on our strategic goals. Second, invest real time upfront. Document your communication preferences, response patterns, and delegation style. I personally use a simple "operating manual" that outlines how I like information presented, what constitutes an emergency, and my working rhythms. This dramatically reduces friction and creates autonomy. The most effective executive-assistant relationships I've observed happen when there's true partnership. My EA often attends key meetings without me, represents my perspective, and brings back the critical information I need – not a play-by-play of everything discussed. They're essentially an extension of my decision-making capacity. Finally, create psychological safety for feedback to flow both ways. My EA has saved me countless times by challenging my thinking or pointing out blind spots in my approach to complex fulfillment partnerships. Remember – your EA likely interacts with every stakeholder in your business ecosystem. When empowered correctly, they become a critical leverage point that expands your leadership capacity exponentially. In our fast-growing 3PL matching platform, this partnership approach has been absolutely vital to scaling effectively while maintaining quality relationships with both eCommerce clients and fulfillment partners.
Nervous-System-Aware Fractional COO & Yoga Teacher Trainer at Alison Reaume
Answered a year ago
After working with executives for over 20 years from multi-million dollar organizations to soloprenuers in a variety of industries, the most successful relationships I've had with executives is by building trust and autonomy. It takes time to trust your EA, but even if you've had a bad experience before or are just hiring your first EA it's leaning into trusting what they are capable of and being transparent in what you have on your plate. Not just from a check the box work list, but on a nervous system level where you are clear about when you are overbooked, overworked, are struggling so that they are given the space to do what they do best and support you when you need it most. And then give them autonomy, lean into the fact that it is likely they may think and process information differently than you and that is to your benefit. Give them a project or an assignment and let them sort it out, this is the who purpose of having an EA to take these things off your plate so let them run with it. This is how you build trust in the relationship and find better ways to strengthen and deepen that relationship over time.
One thing I always tell executives is to treat their Executive Assistant as more than just a calendar manager—think of them as a trusted partner in getting things done. Early in my career, I saw how some leaders underestimated the value of really leaning on their assistants, which only created bottlenecks. When you involve your assistant in understanding priorities and strategic goals, they can anticipate needs, filter distractions, and even push back when something isn't the best use of your time. At spectup, we've seen how the best executives empower their EAs to own their space, making sure communication flows smoothly and decisions get timely support. It's about building trust—when you share context, your assistant won't just schedule meetings but help shape your day in a way that keeps you focused on the big picture. The magic happens when assistants feel confident to speak up and offer solutions, and executives welcome that input without hesitation. I remember a CEO we worked with who'd started including their EA in investor meeting prep, and it changed the game—they anticipated questions and helped align follow-ups. That level of collaboration frees leaders to think ahead, rather than just reacting. So, the short advice: invest time early in building that partnership and keep the door open for honest, proactive communication. It pays off in efficiency and reduces stress for both sides.
One piece of advice I always give executives is to treat your Executive Assistant as a true strategic partner, not just an administrative helper. Early in my career, I learned that sharing your priorities openly and giving your assistant access to your calendar and projects helps them anticipate your needs and manage your time proactively. For example, by understanding my key deadlines and preferred communication style, my assistant was able to filter emails and prep briefing notes, freeing me to focus on decision-making. Regular check-ins are also essential—they keep both of us aligned and allow adjustments before small issues become big problems. When executives trust their assistants with meaningful responsibilities and maintain open communication, the partnership becomes far more productive and less reactive. This approach has made a huge difference in my own workflow and leadership effectiveness.