I’d like to encourage you to stop trying to get past a gatekeeper. In reality, these people are not a fierce negative force. They can be your best ally in getting what you want-a meeting with the boss.
Make the receptionist a friend. Make the assistant a friend. Remember and use their name. Have some sympathy for their job and busy day and tell them so. It doesn’t take long. You can benefit from the fact the people who are typically thought of as “gatekeepers” are actually real people. You can also benefit from the fact that most job seekers calling for a meeting don’t bother to make the gatekeeper a friend.
Will everyone try to help you? Probably not, but see how high a success rate you can get. If they don’t, then you can network in other ways to meet the executive. But don’t say anything negative to either of them. If you underestimate the power of the assistant, you could just end up as toast.
Be ready with a brief and truthful statement about why you want to talk to their boss. Let them know you just need a few minutes. You’ll be amazed at how helpful some of them will be.
I typically call very senior executives during the course of my recruiting. I write down the assistant’s name as soon as I hear it (my brain cells seem to be dying at an alarming rate these days!). By taking time to remember the assistant’s name and being truthful (and brief) about why I was calling, I found a lot of them went out of their way to get me some time on the boss’s calendar.
Whenever possible I compliment the executive on their assistant, and email the assistant my sincere thanks. I’ve never regretted taking a few minutes to make them a friend.
In one case I called an executive three times. The assistant and I had fun brief conversations each time. The first two times, the assistant told me she would give her boss the message, but he didn’t call. The third time she went in to his office and told him he had to take my call! How much better than that does it get?
Everyone you talk to is a networking contact. Instead of rushing to “get past” take a few moments to create a relationship. I hope this helps in your job search networking into the hidden job market.