I have two intense, non-business memories about feeling intimidated.
The first experience happened when I was a 21-year-old undergraduate co-op student. I had just accepted a 6-month position with a large insurance company. The head of the department I was about to join was being promoted to a new role in the company. So the staff invited me to attend their private celebration dinner at the finest restaurant in town.
There were only 6 people at the table. Someone ordered a $100 bottle of wine. This was more than 40 years ago.
The sommelier brought the bottle to the table when someone said, "Herb will taste it."
I had seen James Bond do that in a movie once. So I smelled the cork, then swirled the wine in my glass. I held the glass up to the light. I smelled the wine. I tasted it. And then I said: "I'm sorry, but this is not acceptable."
It tasted terrible, like vinegar. The whole restaurant went silent. My heart was pounding. What if I had accepted the bottle and the others at the table felt it had turned to vinegar? What if the bottle was fine? My only experience in drinking wine up to that point was sipping Manischewitz at Passover.
The sommelier was great. He took the bottle back and brought a new one. A bit later in the evening, I excused myself to go to the restroom. The sommelier stopped me and told me that I handled the situation very well.
He had tasted the wine, and I was right. It had been stored improperly and had turned to vinegar. Phew! My actions were vindicated. But boy was I intimidated by the whole event.
My second memorable intimidation experience happened during a trip to Las Vegas. The dessert sun beat down on The Strip as I strolled to the Mirage and the Seigfried & Roy Secret Garden Zoo, which houses the beautiful white lions and tigers used in their magic act. I walked down a diagonal entry path to enter the attraction.
In front of me was a very large rectangular cage. At the left end were two fully grown male and female white lions sitting on a rock, eyes closed, chests heaving, sound asleep. Or so I thought.
Six to 8 people were standing at that end of the cage taking pictures of these magnificent animals. The male lion's head jerked up quickly and his eyes popped open to meet mine.
The movement was so abrupt that every one of the others watching the lions turned quickly to see what the lion was staring at. Now those strangers were staring at me, too.
That lion's eyes continued to follow me as I moved down the entry path and then walked around its cage. His head pivoted as far around to the right as it could and even behind him. He then moved his head quickly to the left so as not to lose track of me. I don't know if my scent was similar to Seigfried, Roy, or the lion's lunch. But that was intimidating.
I've since learned that you only experience intimidation when you feel out of control regarding a potential outcome or you perceive that the outcome will negatively impact you.
In business, you can overcome feelings of intimidation by following these guidelines.
Tip 1: Don't accept "no" for an answer.
Remember, your case begins when the client says "no" or "I'm all set." Don't let their hesitance become intimidating when really, your fun has just begun.
You have nothing to lose, and you may have a great deal to gain.
Here's something I regularly say to skeptical prospects: "All of our existing clients told us that they didn't need us at the first meeting." Prospective new clients never say, "Wow, I've been waiting for a financial planner (insurance agent, investment advisor, etc.) to call me."
It is likely that they already have a team of existing advisors. I like to ask, "Are you comfortable enough with your existing team of advisors to accept a second opinion — for free?" All you need is a chance to get up to bat and review their current situation.
I also like to think that in my business, there is only "yes" and "maybe"; never "no."
If you do strike out, ask, "Who else do you know who could benefit from working with me?"
Remember, you have nothing to lose.
Tip 2: Stay up at bat. (Keep asking questions.)
Estate size (or income) is just another zero: $1million, $10 million, $100 million, $1 billion.
I have worked with a few billionaires. You might think that because of their financial success, they have covered all of the bases you are going to show them.
But this is rarely the case. Many of them have been so preoccupied amassing their high income or net worth that they failed to attend to many of the details of their own estate.
Consider a recent case in which we were getting nowhere. I just kept asking questions. My opening finally arrived when I talked about the differences in generation-skipping (rule against perpetuities), state by state.
He had just moved his home and business headquarters to a state that had repealed the rule against perpetuities. His previous state, which was the situs for all of his estate planning documents, still had the rule that generation-skipping lasts for the "lives in being," plus 21 years.
He had an 8-year-old grandchild, so a significant amount of his assets won't be in anyone's taxable estate for 100 years. His advisors suggested that 100 years would be "long enough."
I countered. "Ask citizens of United Kingdom how they felt about losing Hong Kong after 100 years," I said.
Of course, no successful client ever accepts anything that's "good enough." He liked the idea of perpetuity meaning perpetual, as in forever.
Tip 3: Get past the gatekeeper 
Gatekeepers are there to say "no." So remember, it's just a game.
