Executive Assistant Mid-Year Check-In: 5 Reasons You’re in Autopilot Mode (And How to Fix It)
The six-month mark is where executive assistant partnerships can hit a dangerous crossroads. After years of placing support roles, we’ve seen what separates the partnerships that thrive from those that fall apart entirely. If you’ve experienced the frustration of an EA partnership that started strong but somehow lost its momentum, you’re not alone. But you also don’t have to accept it as inevitable. Here is why you need an executive assistant mid-year check-in.
The 6-Month Danger Zone
The six-month mark is where many EA partnerships hit a critical crossroads. It’s not that things are going badly – often, they’re going fine. And that’s exactly the problem.
By month six, the initial excitement has worn off. The learning curve has flattened. Both parties have settled into routines that work well enough. Everything feels… comfortable. And comfortable is where the problem begins.
What makes this particularly dangerous is that both the executive and the EA can mistake “fine” for “thriving.” The urgent fires are handled. The systems are running. But the partnership has stopped growing, stopped adapting, and stopped maximizing its potential.
When partnerships plateau at “fine,” they become vulnerable to:
- Complacency that leads to missed opportunities for optimization
- Communication drift as assumptions replace actual conversations
- Skill stagnation when there’s no push for growth or development
- Relationship erosion as the partnership becomes transactional rather than strategic
- Eventual dissatisfaction from both parties who sense something is missing
The 5 Main Reasons EA Partnerships Plateau at 6 Months
From our experience, we’ve identified five critical patterns that emerge around the six-month mark. These issues don’t impact partnerships immediately—they slowly diminish momentum and potential until change becomes necessary.
1. Settling for “Good Enough” Systems
The Problem: By month six, you’ve figured out systems that work. The EA knows how you like things done, and you’ve adapted to their way of managing tasks. It’s functional, so nobody pushes for optimization.
This is where partnerships develop solid rhythms but miss opportunities for excellence. Calendars are managed, travel is booked, projects are tracked – but when you dig deeper, there are often inefficiencies everywhere: duplicate systems, unnecessary approval loops, and missed opportunities for the EA to take on higher-level work.
Warning Signs:
- Systems that haven’t evolved since month two
- Duplicate processes or unnecessary approval steps
- Technology solutions that feel clunky but “work well enough”
- EA not looking for ways to work more efficiently
- Missing opportunities for the EA to take on strategic work
The Fix: Schedule monthly system reviews that go beyond “what’s working” to ask “what could work even better?” Create a shared document where both parties can note inefficiencies as they arise. Set quarterly goals for process improvement, whether that’s implementing new tools, streamlining workflows, or redistributing responsibilities. Make optimization an ongoing conversation, not a one-time setup.
2. Communication Patterns That Stop Evolving
The Problem: Early communication is intentional and frequent. By six months, you’ve fallen into patterns that feel natural but may no longer serve the partnership’s evolving needs.
This often looks like daily check-ins that scaled back to weekly or bi-weekly updates as trust built. Six months in, those weekly check-ins can become routine status reports rather than strategic conversations. The EA may have grown in capability, but the communication style hasn’t evolved to match.
Warning Signs:
- Conversations becoming purely transactional
- Communication patterns that feel outdated
- Decreased proactive communication from either party
- Check-ins that feel like status reports rather than strategic discussions
- Misalignment on priorities or expectations
The Fix: Conduct quarterly communication audits where you both assess what’s working and what needs adjustment. Experiment with different meeting formats – maybe weekly tactical updates and monthly strategic conversations. Establish clear agendas that balance urgent updates with future planning. Create space for the EA to bring ideas and suggestions, not just receive direction. Adjust communication frequency and format as responsibilities evolve.
3. Stagnant Responsibility Levels
The Problem: The EA has proven themselves capable, but neither party has actively discussed expanding their role or taking on new challenges.
This pattern emerges when EAs master their initial responsibilities but aren’t given opportunities to grow. Meanwhile, executives continue handling tasks that could have been delegated months earlier. The EA feels underutilized while the executive remains overwhelmed with work that’s below their pay grade.
Warning Signs:
- Either party feeling unchallenged or underutilized
- Missed opportunities for delegation or growth
- Responsibilities that no longer match current capabilities
- EA asking for more challenging work
- Executive still handling tasks that could be delegated
The Fix: Create a formal responsibility review process every six months. Make a list of all your current tasks and identify what could be delegated based on the EA’s demonstrated capabilities. Establish skill-building goals and create stretch assignments that allow for growth. Set up a “delegation pipeline” where new responsibilities are introduced gradually with proper training and support. Celebrate successful expansions of role and use them as stepping stones to even greater responsibility.
4. Losing Strategic Focus
The Problem: The partnership becomes reactive rather than proactive. You’re managing the urgent instead of focusing on the important.
By month six, many EA partnerships have become excellent at putting out fires but have lost sight of bigger-picture goals. The EA is handling everything thrown at them, but neither party is stepping back to ask whether they’re working on the right things.
Warning Signs:
- Focus shifting from important to urgent tasks
- Lack of discussion about bigger-picture goals
- Feeling constantly reactive rather than proactive
- Daily tasks that don’t connect to larger objectives
- No time allocated for strategic planning or thinking
The Fix: Institute monthly strategic alignment sessions separate from daily operational check-ins. Review quarterly and annual goals together, and ensure daily tasks connect to these larger objectives. Create “strategic time blocks” where both parties focus on future planning rather than current fires. Develop systems for categorizing requests as urgent vs. important, and protect time for the important work. Regularly evaluate whether current activities are the highest and best use of both your time.
5. Skipping Intentional Performance Maintenance
The Problem: When things are going well, it’s easy to skip the check-ins, feedback sessions, and performance maintenance that got you there.
The most dangerous phrase in any EA relationship is “things are going fine.” Fine is the enemy of great. Fine is where working relationships stagnate and eventually deteriorate.
Warning Signs:
- Feeling like the working relationship is “on autopilot”
- Skipping regular check-ins because “everything’s fine”
- Lack of feedback in either direction
- Lack of proactive thinking from the assistant
- Taking the working dynamic for granted
The Fix: Treat performance maintenance as seriously as any other business process. Schedule monthly one-on-ones that focus on effectiveness and efficiency, not just task updates. Create structured feedback loops where both parties regularly share what’s working well and what could be improved. Set performance goals alongside business goals, and track progress on both. Make operational effectiveness a standing agenda item in your regular meetings.
Executive Assistant Check-In Best Practices
The six-month mark isn’t a problem to solve – it’s an opportunity to leverage. This is when partnerships can either plateau or accelerate to the next level. Here’s how to conduct an effective executive assistant mid-year check-in:
Schedule Dedicated Time: Block out at least an hour for this conversation, away from daily operations. This isn’t a quick status update – it’s a strategic partnership review.
Use the Five Key Questions: Structure your discussion around the check-in prompts in the next section that spark meaningful recalibration and prevent autopilot mode.
Document Insights: Take notes on what you discover and create action items with deadlines. This isn’t just a conversation – it’s the foundation for your next phase of working together.
Set 90-Day Goals: Establish specific improvements or changes you’ll implement before your next quarterly check-in. Make them measurable and time-bound.
Follow Up: Schedule a brief 30-day check-in to assess progress on any changes you’ve agreed to make. This shows you’re serious about acting on the insights from your conversation.
The Power of Intentional Executive Assistant Check-Ins
The difference between partnerships that thrive long-term and those that plateau at “fine” often comes down to one thing: intentional maintenance. Great support partnerships don’t happen by accident – they require deliberate attention, especially at the six-month mark.
Here are the executive assistant check-in prompts we recommend for regular partnership recalibrations:
- What’s working really well in our rhythm?
- What feels clunky or unclear?
- What’s one thing I (the assistant) can take off your plate?
- What should we stop doing, start doing, or do more consistently?
- How do we each want to grow in the second half of the year?
Pause. Reflect. Adjust. That’s how good becomes great.
This proactive approach prevents partnerships from getting stuck in “good enough” mode. It’s the difference between partnerships that survive and those that truly thrive for years.
What Success Looks Like After a Successful Executive Assistant Check-in
Partnerships that prioritize intentional recalibration see remarkable transformations. Six-month conversations often reveal that EAs are ready for more strategic work and executives are ready to delegate higher-level responsibilities. These discussions can lead to EAs managing departmental budgets, leading cross-functional projects, or taking on strategic planning responsibilities – opportunities that never would have developed without intentional check-ins.
Some partnerships that seemed to be plateauing have been completely revitalized through mid-year recalibrations. When both parties take time to assess what’s working and what could be better, they often discover that communication preferences have shifted and responsibilities need updating. These conversations transform relationships from “executive assistant” dynamics to “strategic partner” collaborations.
The difference isn’t luck or perfect chemistry – it’s recognizing that six months is a critical juncture that requires intentional attention and proactive adjustment.
Beyond Six Months: Building Partnerships That Last Years
The six-month mark is your first major opportunity to transform a good working relationship into a great strategic partnership. But it’s not the last one. Partnerships that thrive for years understand that recalibration isn’t a one-time event – it’s an ongoing practice.
Quarterly Business Reviews: Schedule formal quarterly reviews that go beyond daily operations to assess strategic alignment, goal progress, and partnership health. Treat these like board meetings for your partnership.
Annual Development Planning: Create yearly professional development plans that align the EA’s growth with your business’s evolving needs. Include skill-building, training opportunities, and role expansion discussions.
Systematic Feedback Loops: Establish open and honest feedback systems that strengthen the working relationship. Weekly brief check-ins, monthly deeper conversations, and quarterly comprehensive reviews create multiple touchpoints for course correction.
Proactive Role Evolution: Plan for the EA’s role to expand and evolve. The best long-term partnerships continuously redefine responsibilities based on demonstrated capability, business needs, and mutual interest in growth.
Partnership Investment: Treat the relationship as a strategic business asset that requires ongoing investment in training, development, and communication.
The Bottom Line: Why Intentional Maintenance Matters
The businesses that build EA partnerships lasting years instead of months don’t get lucky. They get intentional. They understand that the six-month mark isn’t a milestone to celebrate – it’s a critical juncture that requires active navigation.
Great partnerships don’t maintain themselves. They require the same attention and intention that built them in the first place. The six-month mark is your opportunity to ensure your partnership doesn’t just survive – it thrives.
Ready to Turn Good into Great?
Don’t let your EA partnership plateau at “fine.” The six-month mark is your opportunity to recalibrate, realign, and recommit to building something exceptional.
The difference between partnerships that coast and those that accelerate often comes down to one intentional conversation. The question isn’t whether your partnership needs a mid-year check-in – it’s whether you’re ready to have the conversation that takes it to the next level.
Ready to beat the odds and build an EA partnership that gets stronger, not staler, over time? Get our ‘Maximize Your Assistant’ toolkit for the resources and guidance to build a strategic partnership that can last years, not months.
