Getting Past the Executive Assistant to Reach a Decision-Maker

EAs field pitch calls constantly and can tell within a sentence whether a caller is being straight with them. Say clearly who you are, who you're trying to reach, and why, in one or two sentences, rather than trying to sound like you already have a relationship with the executive or burying the ask in vague language about "connecting."

An EA who understands exactly what you want is far more likely to either put you through, tell you honestly that it isn't a fit, or point you to the right person instead, all of which are better outcomes than a call that goes nowhere because nobody could tell what you actually wanted.

Asking an EA to "pass along a message" gives them nothing to actually act on. Instead, offer something specific and short enough that they can forward it as-is: a two-sentence summary of the specific reason this matters to their executive right now, tied to something real, a recent announcement, a role change, a competitor's move, not a generic pitch.

The easier you make it for the EA to forward something that reflects well on their own judgment for passing it along, the more likely they actually do it instead of letting it sit in a folder.

The reps who reach executives most consistently have usually talked to the EA more than once before asking for anything. A short, genuinely useful check-in, sharing a relevant piece of news about the executive's industry, congratulating a company milestone, costs almost nothing and builds the kind of familiarity that makes the next real ask land differently.

This only works if it's genuine. An EA can spot a transactional "relationship-building" email that exists purely to set up a future ask, and it tends to backfire worse than never reaching out at all.

A clear no from an EA is useful information, not a wall to climb over by going around them. Ask directly what would make the request relevant, timing, a different angle, a different stakeholder, and respect the answer. Trying to bypass the EA entirely after a no, by finding the executive's personal email or reaching them on a different channel, usually reads as exactly what it is and can burn the account for good.

If the EA says the timing is wrong, take the honest answer over pretending you didn't hear it: a well-timed follow-up months later, referencing that earlier conversation, tends to land far better than an end run around the person who told you no.

The EA shouldn't be the only thread you're running on a target account. Reach other stakeholders in parallel, a champion-level user, a peer executive, so the deal isn't entirely dependent on one gatekeeper's willingness to forward a message. This isn't about working around the EA; it's about not putting all the account's outreach through a single point of contact, which is fragile regardless of how well that relationship is going.

When a deal does move forward, keep the EA in the loop on scheduling and logistics rather than dropping them the moment the executive replies. That's usually the point where reps stop being polite to the EA, and it's also the point the EA remembers longest.

Habits that keep the gatekeeper on your side:

• State who you are, who you want to reach and why in one or two plain sentences on the first call.
• Offer a short summary the assistant can forward as written, tied to something real like a recent announcement or role change.
• Check in with something useful before you need a favor, so the relationship exists when you make the real ask.
• Treat a clear no as information, ask what would make the request relevant, and respect the answer.
• Run parallel threads to other stakeholders so the account never depends on one person forwarding a message.