Why EAs who push back well get further than the ones who never do

Conversations EAs are avoiding (and how to have them)

There's a conversation you've been putting off.

You know the one. Where you're sitting in a meeting thinking "this keeps happening and someone needs to say something." Or you're in the car on the way home replaying the moment you didn't speak up, again. Or you've drafted the message three times and deleted it every time because you couldn't figure out how to say it without it sounding like a complaint.

In our latest group coaching session, I asked how everyone was feeling about managing up before we started. Half the room said uncomfortable. Most said it depended entirely on the executive.

Which, yes. But the EAs I've watched succeed long-term aren't the ones who "got lucky with a great boss". They're the ones who figured out how to say the hard thing in a way that actually landed.

That's what this is about.

Before anything else: is it actually worth raising?

I want to start here because I think this is where a lot of advice goes wrong. Not everything deserves a conversation. Some things are genuinely yours to manage internally. Some things are worth noting once and letting go.

Falling off that horse on either side costs you. Raise everything and you become high-maintenance, your exec starts filtering you out. Raise nothing and you become invisible, ineffective, and eventually you leave.

So before you say anything, run it through four questions:

1. Is this a pattern or a one-off? A diary clash is a one-off. Never having visibility of what's coming is a pattern. One-offs: usually let it go. Patterns: worth naming.

   
   

2. Does it actually affect your ability to do your job? If the honest answer is "no", you might just be annoyed. That's relatable, but it might not need a conversation. If "yes", it's a legitimate professional discussion, not a personal complaint.

   
   

3. Is there a business case for changing it? DO NOT skip this one. If raising it leads to a better outcome for your exec, your team, or the business, go. If it's mainly about your comfort, reframe it first, or sit with it a bit longer.

   
   

4. Are you the right person to raise it, right now? Timing and relationship matter more than the actual words you use. Even the right conversation can land badly if your exec is in crisis mode or trust is still being built. Read the room.

Walk yourself through those four questions and you'll usually know. Raise it. Raise it differently. Or park it for 30 days and see if it still feels urgent.

The three conversations that actually come up

If you've decided something is worth raising, the next question is how.

The structure I use, and the one we worked through in the session, is SBI. Situation, Behaviour, Impact. It was developed by the Centre for Creative Leadership and it works because it takes the personal charge out of the conversation. Instead of commenting on who someone is, you're describing what happened, what you observed, and what the effect was. Then you add a clear ask.

Here's what that looks like across the three conversations EAs tend to avoid most.

"I need more from you"

This one is so common and so damaging when it goes unspoken.

You don't have the context you need. You're not across the priorities. You're working half-blind and compensating by just... working harder. And never actually saying anything.

Here's the reframe: asking for what you need is not a weakness. It actually serves your executive. You do better work when you're not guessing.

Instead of: "I feel like I'm not always across things."

Try: "The last couple of weeks, the board prep and the client renewal, I didn't have enough context to get ahead of things. I kept ending up reactive when I could have had stuff sorted earlier. Can we do a quick check-in each week so I know what's coming?"

Specific situation. Specific behaviour. Real impact. Clear ask. This one often works fine over Slack or email. There's no emotional charge, it's practical, and it gives your exec something to actually respond to.

"I want to flag something"

This is the one that makes people most nervous. The fear is that it'll land as a complaint, or damage the relationship, or put your exec on the defensive.

And sometimes, if it's handled badly, it does.

The shift is this: your exec doesn't need to know you're frustrated. They need to know there's a problem affecting the work, and that you've thought about a fix.

Instead of: "I find it really stressful when you change priorities last minute."

Try: "Can I flag something I've been noticing? The last month or so, when priorities shift after the weekly plan is set, I end up redoing work. Last week it was about three hours before the board pack. Could we do a quick check mid-week to catch changes earlier?"

No blame or emotion. What you're doing now is naming a specific pattern, pointing to a concrete example, and providing a suggested solution.

This one belongs in person or on a call, not over text. Tone does a lot of work in these conversations and text strips it out entirely.

"Here's what I think"

This is the one that makes EAs feel like they're overstepping. Who asked you?

The answer is: you don't always wait to be asked. Strategic EAs offer a view.

There's a way to do it that lands well, and a way that doesn't.

Badly: "I think we should approach this differently." Too vague. Easy to dismiss.

Well: "I've been looking at the supplier review. I've got a thought on the sequencing that might be worth hearing. Got two minutes?"

That little ask at the end matters. You're not pushing your opinion on anyone. You're flagging that you've got something useful and letting them choose to receive it. Almost no executive says no to that sentence. And once they say yes, use SBI.

"The last two reviews, we went to commercial terms before internal sign-off was confirmed. Both times we had to renegotiate. If we flip the sequence and lock internal alignment first, I think we'd move faster and look more organised. Worth trying it this round?"

That's not overstepping. That's exactly what a trusted operator sounds like.

A few things that will sink it regardless of how good your content is

You can nail the SBI framework and still have the conversation go sideways. Usually it's one of these:

Starting with an apology. "Sorry to bring this up, I don't want to cause any issues, but..." You've already told your exec this is uncomfortable and probably not worth their time. They'll agree with you.

Being vague. "Communication could be better" is a mood, not feedback. Give them something specific they can actually do something with.

Dumping the problem without a direction. "I'm really struggling and I don't know what to do" puts everything in their lap. Come with at least one idea, even a rough one.

Picking the wrong moment. In front of others. Right before something big. When they're clearly under pressure. Timing is genuinely part of the skill.

Over-explaining because you're nervous. The more you pad it out, the more diluted the actual point gets. Say the thing. Stop. Let them respond.

The EAs who get promoted, protected and genuinely valued aren't the ones who never push back. They're the ones who push back well.

If you've got a specific situation you want to talk through one on one, you can book a free 20-minute call with me.

I'd love to hear from you. ☕

Trinity

Trinity James is a Career Coach, founder of Views Professional Development and the APAC Lead for EA How To — a professional development membership for Executive Assistants across the globe.