7 Delegation Mistakes That Make Your EA Ineffective.

You finally hired an executive assistant. They're smart, capable, and motivated.

So why are you still drowning in admin work?

Spoiler: It's not them. It's how you're delegating.

The Delegation Fallacy

Most founders think delegation works like this:

1. Hire talented person

2. Tell them what to do

3. They do it

4. You have more time

Reality check:

What actually happens:

1. You assign a task

2. They ask 5 clarifying questions

3. You give more context

4. They complete 80% of it

5. You spend 30 minutes fixing the 20%

6. Next time, you just do it yourself because "it's faster"

Sound familiar?

This isn't a talent problem. It's a systems problem.

The 7 Delegation Mistakes That Make Your EA Ineffective

Mistake #1: Delegating Tasks Instead of Outcomes

What you're doing:

• "Can you schedule a meeting with the investor?"

• "Can you book my travel for next week?"

• "Can you draft an email to the client?"

Why it fails: You're delegating the task, not the result. They don't know the why, so they can't make decisions independently.

What to do instead:

• "I need to close this investor by EOQ. Schedule a meeting when they're most likely to say yes, prep a brief on their portfolio companies, and send a pre-meeting agenda."

• "I need to be refreshed for the client presentation. Book travel that minimizes stress and maximizes rest, even if it costs 20% more."

• "The client is frustrated about the delay. Draft an email that acknowledges the issue, provides a concrete timeline, and reinforces our value proposition."

The difference: One is a task. The other is an outcome with decision-making criteria.

Mistake #2: Not Defining "Done"

What you're doing: "Can you handle the vendor onboarding?"

Why it fails: "Handle" could mean:

• Send them the contract?

• Set up their account?

• Schedule a kickoff call?

• All of the above?

Without a clear definition of "done," you get incomplete work.

What to do instead:

Create a "Definition of Done" for common tasks:

Example: Vendor Onboarding is "done" when:

• ✅ Contract signed and filed in Google Drive

• ✅ Payment set up in accounting system

• ✅ Account created with proper permissions

• ✅ Kickoff call scheduled with agenda sent

• ✅ Team notified via Slack #vendor-updates channel

Now "done" means the same thing to both of you.

Mistake #3: Delegating Without Authority

What you're doing: "Can you research event venues and send me options?"

Why it fails: You've delegated the work, but not the decision. They do all the research, send you 10 options, then wait for you to pick one.

You're still the bottleneck.

What to do instead:

Delegate with decision-making authority:

Level 1 (Recommend): "Research venues and recommend your top choice with reasoning"

Level 2 (Decide + Notify): "Book the venue that best fits these criteria and notify me"

Level 3 (Decide + Execute): "Handle all event logistics within $5K budget — I trust your judgment"

The more authority you delegate, the more time you actually save.

Mistake #4: No Decision-Making Framework

What you're doing: Your EA asks, "Should I accept this meeting?"

Why it fails: Without criteria, every decision requires your input.

What to do instead:

Create an if/then decision matrix:

Meeting Acceptance Criteria:

• ✅ Potential client over $50K ARR → Accept

• ✅ Existing top-10 client → Accept

• ✅ Strategic partner or investor → Accept

• ⚠️ Networking meeting → Only if we have a specific ask

• ❌ Vendor pitch → Decline with template response

• ❌ "Pick your brain" request → Redirect to office hours link

Now they can make 90% of decisions without asking you.

Mistake #5: Delegating Once, Then Taking It Back

What you're doing: You delegate email screening, then check your inbox anyway "just to be safe."

Why it fails: Your EA knows you're double-checking their work, so they stop taking initiative. Why make a decision if you're going to override it?

This creates learned helplessness.

What to do instead:

Week 1: Review their decisions daily and provide feedback Week 2: Review twice weekly Week 3: Spot-check once Week 4+: Trust the system

The goal: Get to a place where you DON'T check their work.

If you can't stop checking, your documentation isn't clear enough — that's the system failing, not the person.

Mistake #6: No Feedback Loop

What you're doing: Your EA makes a decision you disagree with. You fix it silently and move on.

Why it fails: They have no idea they did it wrong. Next time, they'll make the same mistake.

What to do instead:

When something goes wrong:

1. Explain the error: "The meeting got scheduled during my deep work block"

2. Clarify the rule: "Mornings are for strategic work — meetings start at 11am"

3. Document it: Add this to your calendar management guidelines

4. Close the loop: "Thanks for catching this — the updated guidelines are in the wiki"

Every mistake is a documentation opportunity.

Mistake #7: Treating Your EA Like a Mind Reader

What you're doing: "Just handle it the way I would"

Why it fails: They're not you. They don't have your context, your relationships, your priorities, or your decision-making patterns.

What to do instead:

Create an "Operating Manual" that includes:

• Your priorities and values

• Communication preferences (when to text vs email vs Slack)

• Decision-making frameworks

• Your pet peeves (nothing bothers you more than...)

• Your quirks (you hate calls before 9am, you triple-check every number)

Example snippet:

Communication Preferences:
- Text: Only emergencies (client crisis, system down)
- Slack: Urgent + needs response today
- Email: Non-urgent, can wait 24-48 hours
- Shared doc: Status updates, weekly reports

Meeting Preferences:
- No meetings before 10am (deep work time)
- Maximum 4 external meetings per day
- All meetings require agenda 24hrs in advance
- Default meetings to 25 or 50 minutes (buffer time)

Decision Authority:
- Under $500: Your call, notify me monthly
- $500-$2K: Your call, notify me within 24hrs
- $2K-$10K: Get my approval first
- Over $10K: We discuss together

The clearer your manual, the less they need to ask.

How to Build a Delegation System That Actually Works

Step 1: Document Your Defaults

For the next week, every time your EA asks you a question, write down:

• The question

• Your answer

• The criteria you used to decide

Step 2: Turn Decisions Into Rules

Look for patterns. Turn repeated questions into documented frameworks.

Step 3: Delegate in Layers

Don't hand over everything at once. Start with:

• Week 1: Low-risk tasks with clear rules (calendar invite formatting)

• Week 2: Medium-risk tasks with decision authority (email screening)

• Week 3: High-value tasks with oversight (meeting prioritization)

• Month 2+: Strategic tasks with full autonomy (vendor management)

Step 4: Measure What Matters

Track:

• ❓ How many times per day does your EA interrupt you?

• ⏰ How long does it take to complete routine tasks?

• 🎯 What percentage of decisions can they make independently?

Goal metrics:

• < 2 interruptions per day

• 90%+ independent decision-making

• 15+ hours/week reclaimed

The Real Job of an Executive Assistant

Your EA's job isn't to do tasks.

It's to build systems that make tasks unnecessary.

The best EAs:

• Turn one-off requests into documented processes

• Notice patterns and proactively create workflows

• Build decision frameworks so they don't need to ask

• Improve your operations, not just execute them

But they can only do this if you give them the tools: documentation, authority, and feedback.

The Bottom Line

If your EA keeps asking you questions, that's not a sign they're incompetent.

It's a sign your delegation system is incomplete.

The goal isn't to have someone who does what you tell them.

The goal is to build systems that run without you telling anyone anything.

Ready to fix your delegation system? Book a strategy call with JobSure — we'll audit your current workflows and show you exactly where the gaps are.