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Strategic Planning with Your Executive Assistant

Imagine this: you, sitting at your desk, faced with a mountain of strategy reports, timelines, and decision trees. It’s the classic executive struggle. But here’s the kicker—what if you already have a secret weapon at your disposal that could turn this chaotic pile of to-dos into a well-oiled strategic machine?

No, we’re not talking about a fancy new app or the latest “productivity hack.” We’re talking about someone who’s been there all along—your Executive Assistant (EA).

The Game-Changing Role of an Executive Assistant

Your EA isn’t just there to manage your calendar or send out reminders about meetings you probably scheduled six months ago. Nope. The modern EA is the Robin to your Batman, the Watson to your Holmes, and occasionally, the Gordon Ramsay to your undercooked business strategy. (Sorry, not sorry).

Executive Assistants today aren’t about administrative support—they’re about strategic partnership. And if you haven’t started leveraging your EA in your strategic planning, you’re missing out on an invaluable asset.

Here’s why and, more importantly, how you should be doing it.

Why EAs Make Excellent Strategic Partners

Before we get into the how, let’s answer the million-dollar question: why involve your EA in strategic planning? Aren’t they supposed to just take notes and organize things?

Here’s a secret: EAs have a bird’s eye view of your organization and your schedule, relationships, and priorities. In short, they know what’s happening behind the scenes (maybe even better than you do!).

1. They’re Masters of Multi-Dimensional Insight: Think of your EA as the spider at the center of your organization’s web. They’re not just hearing the news from one department; they’re hearing it from every department. This means they have a unique perspective on how different parts of your business connect, which silos need to be broken, and which projects need an extra push to align with the broader strategy.

2. EAs Have An Eye for Trends and Patterns: While you’re knee-deep in financial reports and vision decks, your EA is observing the subtle patterns: who consistently delivers, which meetings are turning into time-wasters, and what projects are taking off faster than a SpaceX rocket. EAs have the advantage of connecting dots that might not even be on your radar yet.

How to Involve Your EA in Strategic Planning (And Make It Work)

You’ve probably realized by now that involving your EA in strategic planning is a no-brainer. But like any relationship, it’s all about finding your rhythm. Let’s dive into how to do it effectively:

1. Share Your Vision Early On

Communication is key—just like in any relationship (business or otherwise). Your EA needs to be in the know about the “big picture” vision for the company. When you share the overall goals, priorities, and potential obstacles, your EA can align their efforts with what truly matters.

But here’s the fun part: don’t just dump your vision on them. Have a casual conversation. Grab coffee or lunch and chat it out. Think of it as strategy without the PowerPoint.

Pro-tip: Give them context, not just content. Help them understand why this strategy matters. Maybe it’s about gaining market share or optimizing internal processes. When they get the “why”, they’re more likely to identify opportunities and roadblocks with you.

2. Delegate the Details (Without Micromanaging)

Strategic planning can be exhausting because, well, it’s easy to get lost in the weeds. But here’s where your EA shines. They’re detail-oriented ninjas who thrive on creating order out of chaos. Delegate those nitty-gritty details to your EA, whether it’s creating a project timeline, coordinating with stakeholders, or gathering essential data.

Remember: delegation isn’t about dumping tasks. It’s about entrusting responsibilities. Give them the authority to act and make decisions in their domain. You’ll be surprised at how efficiently your EA can keep the strategic wheels turning.

3. Get Their Input (And Actually Listen)

You didn’t hire your EA because they can type fast, right? (Although, hey, that’s a bonus). You brought them in because they’re smart, insightful, and resourceful. Leverage that!

When making key decisions, get their input. They have a perspective on things that you don’t, and they’ll often have the empathy to spot red flags or opportunities that you might overlook.

And the key part? Actually listen. Ask for feedback regularly, and encourage them to share their ideas, no matter how outside-the-box they might seem. You never know—your EA might drop the next big idea over lunch.

Integrating Your EA into the Strategic Process: A Step-by-Step Approach

Let’s break it down. Here’s a roadmap to ensure you and your EA work in strategic harmony:

Step 1: Initial Strategic Review Sessions

Start with a review session where you and your EA discuss past strategies. What worked? What tanked? (We’re all human; even strategies bomb sometimes.) Take time to set goals and decide on metrics for success.

Step 2: Regular Check-In Meetings

While most EAs and executives have regular check-ins, these meetings shouldn’t be limited to “here’s your schedule.” Include a strategy update in every meeting. Talk about the goals, current progress, and any upcoming pivots.

Step 3: Involve Them in Planning Retreats

Planning retreats shouldn’t just be for executives and directors. Include your EA in these sessions. They can provide valuable insights and handle the logistics, letting you focus on the big picture without stressing over the minutiae.

Step 4: Evaluate and Reflect Together

At the end of each quarter, conduct a strategy reflection with your EA. Analyze what hit the mark and what didn’t. Reflecting together helps in realigning your approach for the next quarter.

Examples of How EAs Drive Strategy

Still skeptical?

Let’s get real and look at some concrete ways your EA can help you with strategic planning:

1. Planning for Market Expansion

If you’re exploring new markets or expanding into new territories, your EA can take the reins on research and coordination. They can schedule exploratory calls, research potential partners, and ensure all data is neatly packaged and ready for you to make informed decisions.

2. Streamlining Internal Processes

Are you dealing with bottlenecks that are causing delays? Give your EA the responsibility to coordinate a cross-departmental task force. They’ll have a better grasp of who to involve, when to meet, and what to tackle first, helping streamline internal workflows faster than you could on your own.

3. Project Managing High-Priority Initiatives

You can’t oversee every major project without burning out. Instead, let your EA manage the timeline, handle follow-ups, and ensure all parties are on the same page. This way, you’re free to focus on strategy while your EA keeps the projects on track.

Avoiding Common Pitfalls

Of course, nothing’s perfect—strategic planning with your EA included. Here are some common pitfalls to watch out for and how to avoid them:

1. Not Setting Clear Boundaries: There’s a difference between strategic delegation and overloading your EA. Clearly outline which decisions are theirs to make and which need your input. This prevents confusion and avoids misunderstandings.

2. Skipping Feedback: Make it a habit to ask your EA for feedback on the planning process itself. What’s working for them? What’s not? This feedback loop helps fine-tune your collaborative approach over time.

3. Undervaluing Their Role: Your EA isn’t just another cog in the wheel—they’re a key player. Recognize their contributions and show appreciation. This keeps them motivated and encourages proactive engagement in future planning.

Your EA Is Your Secret Strategic Weapon

There’s a reason why the most successful executives often have strong partnerships with their EAs. It’s not about offloading work—it’s about elevating your strategy. Your EA isn’t just an admin—they’re a strategic asset, ready to help you anticipate challenges, tackle opportunities, and bring your vision to life.

So, next time you’re knee-deep in strategic planning, don’t just see your EA as a note-taker or organizer. See them as a partner in crime (the legal kind, of course) and start leveraging their potential to the fullest.

After all, you already have a secret weapon in your corner. Now, it’s time to start using it.

A Word to the EAs

If you’re an Executive Assistant reading this, give yourself a pat on the back (seriously). You are the unsung heroes of strategic planning, the glue that holds it all together. Keep pushing, keep strategizing, and most importantly, keep being awesome.

There you go—strategic planning with your Executive Assistant can be a game-changer if you do it right. Remember, it’s all about partnership, trust, and a shared vision for success. Now go on and start plotting your next big strategy, one coffee chat at a time.

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