06/01/2013 06:17 pm ET Updated Aug 01, 2013

Life Lesson: Making the Ask

Twenty-five years ago, Bob Babbage, who is now Kentucky's most successful lobbyist, was running for State Auditor and I was his combination of Finance Chair/Campaign Chair/Press Secretary.

It was a small campaign.

I took Bob to lunch with one of my most successful clients to ask for a donation. I was extremely nervous and asked Bob to ease into the request at the end of lunch after he and my friend got to know each other better.

Bob agreed.

Thus, we sat down, the waiters handed us the menus and the very first thing Bob said was, "Johnny (not the real name), you look like the kind of guy who could give my campaign $4,000." As I was falling out of my chair, Johnny responded, "No, but I can give you $1,000."

End of conservation. We had a nice lunch and Johnny handed over the check on the way out the door. Johnny became Bob's friend and gave to every campaign after that.

I learned an important life lesson in raising money for charities or political campaigns: How to make the ask.

Bob and Johnny both understood that Bob was going to ask for a donation. Rich people get that kind of request all the time. By asking upfront, Bob got the issue off the table and the tension out of the situation.

Bob did a couple of other things right.

He asked for the money himself. He did not send a letter or what is more common now, the scare tactic email. He did not have a flunky or hired gun make the pitch as so many charitable organizations and political campaigns do.

Johnny wanted to have a direct relationship with the head dog and was willing to write a $1,000 check to have it. Bob understood that is it a lot harder to turn down the candidate, looking you in the eye, than it is turn down a call or a letter.

I was nervous that Johnny would be unhappy with me. I thought he would be upset about putting him in a position where he was being asked to write a significant check.

The opposite held true. Johnny was thrilled that I had such as close relationship with someone with vast potential and that he could help Bob, and me, by donating to the campaign.

Babbage understood the Tip O'Neill adage: People liked to be asked.

Babbage got a $100 donation from Tip himself when he was running for his next office, Secretary of State.

O'Neill had spoken to a group in Kentucky and Bob had arranged for he and I to get O'Neill to the airport. Bob told the Speaker, "I read where you said people liked to be asked, and I would like for you to donate to my campaign." O'Neill gave Bob a check for $100. (I was campaign treasurer and kept a copy of the check.)

The only race Babbage ever lost was the only time Kentucky used public financing in a gubernatorial race. His ability to ask anyone at any time for a donation was negated.

Fundraising comes down to factors. Being brave enough to ask someone for money and finding people who are interested in the cause you are espousing.

The outstanding new book, Happy Money, written by two behavioral economists, helped me quantify what Tip O'Neill knew decades ago: People like to be asked and feel better about themselves when they use their money to help others.

The other factor is how they are being asked and who is doing the asking.

I had the leader of a charitable organization take my wife and I to dinner. All evening long, I kept waiting for the pitch for money. I never got it. Instead, I got a letter a week later.

It would have been hard to say no when we were all sitting together. It was a lot easier to say no to the letter.

I know there must be someone responding to the barrage of email, phone solicitors and impersonal direct mail requests that clog our mailboxes, but I am not one of them. If you trace my donations to any charity, you will find that someone I knew or respected asked me personally to help out.

The other thing the charity or candidate needs to do is say thank you.

I like to help. Everyone likes to help, but no wants to be taken for granted or treated like an ATM machine.

I had a politician who hit me for a donation every election cycle and ignored me until the next election came up. I finally cut him off and explained why.

In business, your best clients are repeat clients. The same holds true in raising money. Saying please and thank you will take you a long way.

And could allow your charity or campaign to achieve your dreams, goals and objectives.

Don McNay is the bestselling author of Life Lessons From the Lottery and co-author of Life Lessons from the Golf Course.