The Delegation Mistake Costing You Time and Money: Half-Baked Instructions
Ask any experienced assistant what consistently gets in the way of doing their job well, and you’ll hear the same answer over and over: unclear, incomplete, or just plain vague instructions.
That's right. It’s not too many meetings. Not outdated systems. Not even burnout. It’s the lack of direction from the very people who depend on them most.
Founders, entrepreneurs, and small business owners—you might be aware that you have the vision, the ambition, and the chaotic calendar to match. And while these traits are a strength in many ways, it also means you have a tendency to move fast, often causing your thoughts to come out in fragments: half-decisions, vague one-liners, or “just figure it out” energy.
The real problem? When those fragments are "delegated" to your assistant and you expect them to execute flawlessly, you’re setting both of you up to fail.
Let’s be clear: executive assistants are not magicians. They’re not mind readers. And they’re definitely not wizards conjuring your travel plans or inbox zero with a flick of a wand. They’re highly capable, resourceful professionals who cannot do their job without real information.
And by “real information,” I mean clear expectations, accurate timelines, historical context, and answers to follow-up questions. When you can’t provide that, here’s what actually happens:
Scenario 1: They Move Forward With Your Half-Thought
Your assistant does their best with what you gave them (which wasn’t much), so they make assumptions, guess your preferences, and try to fill in the blanks.
And then?
They get it wrong. Not because they’re careless, but because you didn’t give them the right input.
Now you’re annoyed. You think they’re not “getting it.” They feel blamed for your lack of clarity. Trust erodes. Resentment brews. And they start questioning whether they’re the problem—when the real problem is your rushed, incomplete communication.
Scenario 2: They Ask Someone Else to Decode You
They turn to someone else on your team—John, Suzie, whoever seems to “get” you—and ask, “What do you think she meant by this?”
Now you’ve got a game of telephone happening inside your business. Your assistant is executing based on someone else’s interpretation of your half-thought. That person might mean well, but they’re not you.
And suddenly your EA is building systems or making decisions based on someone else’s guesses—not your actual direction. You lose control over your vision. Your team gets confused. And the assistant you hired to make your life easier is now just chasing shadows.
Scenario 3: They Stop Until You “Circle Back”
Your assistant realizes they don’t have enough to go on. So they wait for clarification.
Except you never get back to them. You meant to, but something else came up. A week goes by. Then two. That project you wanted handled is now stalled, and you’re annoyed that it’s still sitting on their desk.
Meanwhile, your assistant feels stuck and demoralized. They’re trying to do their job, but you’ve given them neither the information nor the access to succeed. You’re frustrated, they’re frustrated, and nothing moves forward.
Here’s the harsh truth:
If you don’t have time to answer your assistant’s questions, you don’t have time to have an assistant.
Hiring support isn’t a passive move. It requires active participation and intentional delegation. You are the power source for your EA: your clarity, your expectations, your strategy.
Without that? They’re just guessing. And you’re just throwing money at someone you’re not really empowering.
Assistants are not plug-and-play. They’re not like a lamp you plug into your office wall that magically illuminates your priorities. They need your input to function. And not just once, but consistently.
Don’t expect them to operate at a high level if you can’t take five minutes to explain what success looks like.
Don’t punish them for missteps that stem from your own ambiguity.
And for the love of progress, don’t tank a great assistant’s confidence or career trajectory because you were too overbooked to give a real answer.
How to Delegate Better (And Get More From Your Assistant)
If you want to be the kind of leader who gets the best out of your assistant, here’s where to start:
Get specific. If you’re asking for help, include context. Deadlines. Who it impacts. Why it matters.
Make time to answer questions. A five-minute conversation now is better than a five-day delay (or a do-over) later.
Elaborate on recurring tasks. If it’s something they’ll be doing again and again, take the time to get it right the first time.
Give feedback without blame. If something isn’t working, talk about the system or process—not just the person. What wasn’t working and how can we improve it?
The assistant-founder relationship has the power to be wildly transformative. It can make your business more organized, your time more valuable, and your life less chaotic. But only if you treat it like a partnership—not a guessing game that even Sherlock Holmes would struggle to solve.
So, founders, CEOs, and entrepreneurial leaders: if you want to stop being the bottleneck in your business, start by answering your assistant’s damn questions. Completely. Consistently. And with respect.
That’s how the magic happens.
Want to learn how to delegate to your assistant better? That’s what I do.
Schedule a Discovery Call here and let’s talk about how to get you both on the same page.