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4 tips for overcoming feelings of intimidation with clients

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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.Great business people know how to turn a "no" into a "yes."

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.)You can avoid intimidation by never giving up.

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.

Gatekeepers are there to say “no.”  So remember, it’s just a game.

How can you get around the gate-keeper and through the first gate? 

The client or one of the gate keepers (assistant, advisor) will frequently ask you to send more information so they can review your ideas. “Send more information” can be the same as a “no.” Here’s one way around that: Somewhere along the line, you identified what this person does for a living. Use that. Explore how thie prospect handles someone who tried to mount the old brush-off, “Send me more information?” In other words, take a page for your prospect’s own playbook.

Even after you pass the first gate, you may still have “gatekeeper” issues. Years ago, I had a client who owned a number of hardware stores. He only wanted to look at term insurance. The gate was closed to having any other conversation. But I was not intimidated.

I called the store as an anonymous potential customer. I asked, “What is the name of the best paint you sell? And, what is the name of the cheapest paint you sell … the one you might use to paint your dorm room just before you moved out?”

My last question: “If you were painting your own house, what paint would you select?”

The sales associate answered all of my questions. I used that material during my next presentation with my prospect. Here’s how: 

  • Instead of term, my presentation column used the name of the dorm room paint;
  • Instead of universal life, my column used the name of the paint he would use for his own house; 
  • And instead of whole life, my column header used the name of the highest quality paint they sold. 

He understood very quickly, then bought permanent coverage, a combination of universal and whole life.

Tip 4: Make the complex understandableYou can zap intimidation quickly by making the complex more accessible.

Complexity creates opportunity. This is where you may want to use the “send me more information” prompt for yourself. 

Never feel intimidated when a prospective new client lays out a complicated situation and poses several complex questions. You also don’t want to try and fake your through material you may not fully understand.

Instead, take down the information and say to the client: “Let me be sure that I fully understand your situation.” Then, read back to the prospect the information you took down. 

Next, tell your prospect that you realize the complexity of the situation. “You have asked very good questions. Let me be sure that I have them down exactly the way you phrased them.” Take time to read back those questions, in the prospect’s own words. 

Finally, you can show the prospect that you care. “Your questions deserve more than my quick response.  Let me review this information and get back to you” soon. Then, follow up when you said that you would. 

Don’t be intimidated by any client or any situation.  Ted Williams batted .406 and is regarded as one best hitters — if not the best ever — in baseball.  That means that nearly 60 percent (59.4 percent) of the time, he did not get a hit. 

If you get past the gatekeeper 40 percent of the time, that’s great. Just keep going up to the plate. Keep improving your skills. If you do strike out, role-play the situation with the most successful people in your office. Ask them how they would have handled the objection. Remember to seek mentorship from people who have genuine insight into your business.

All too often, I see inexperienced advisors sit down with other inexperienced advisors in an attempt to improve their outcomes. Why? Their batting average is like yours. 

The famous football coach Vince Lombardi told his players that “practice does not make perfect … Only perfect practice makes perfect.” otherwise you are just practicing the same old mistakes. 

There are very successful advisors either in your office or affiliated with your office.  Contact them.  It is amazing how often they are willing to share their experience with others.

Let me close with one last story.  A young advisor had attended one of my training classes.  We discussed the current estate tax exemptions, federal and state.  And we discussed the havoc caused by privately-held business owners not having adequate liquidity to pay estate taxes. 

The advisor came back after a failed attempt to convince a very wealthy business owner that he needed life insurance to pay for his estate taxes on an estate well in excess of the federal estate exemption.

I asked, “How was his marriage?”  The advisor said, “How did you know his marriage was in trouble?”  I said, “Because you told me how successful his private business was.” 

I then asked, “Do his kids side with him or their mother?”  Again the advisor asked, “How did you know that there is a strong rift between him and his kids?”  Same answer.

The kids felt that he spent way more time with the business than with them.   Why would he be interested in helping his children pay for his estate taxes? 

I then asked, “When is his first grandchild due?” The young advisor was beside himself.  “Are you psychic?” he asked.  “His first grandchild is due later this month.” 

I told the advisor to wait until the middle of the following month and call the prospective client back.  Once that little hand wraps around grandpop’s finger, he will be ready to talk about estate preservation.  He did and sold the coverage.

How did the young advisor know so much about the prospect’s personal situation?  Because, I emphasize the importance of building a family tree.  Are you married?  Who’s alive above you (parents, grandparents)?  Who’s alive below you (children, grandchildren)? 

How much financial support will you get from your siblings for your parents’ long-term care?  How much financial support will you get from your spouse’s siblings for your in-laws’ long-term care?

Don’t be intimidated.  Just stay at bat.  Ask another question.  And, if you are no longer in front of the prospect or client, then ask that question of the others in your office who can help you get back up to bat.

See also these articles by Herbert K. Daroff:

Changing your domicile: weighing estate costs and benefits

Citizenship and work habits: Do your job — all of it!

3 reasons why we don’t sell as much life insurance as we should

Taking your practice to the next level: a 5-stage guide


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