What questions do you dread when you are exploring a client’s financial needs? The Dow Jones Wealth Management Advisory Council—which is made up of eight wealth managers and one industry consultant—recently unveiled what it believes are some of the toughest issues for wealth managers to discuss with clients.

Topping the list are immature children, the death of a spouse and dealing with children from a previous marriage.

To serve their clients best, advisors can’t shy away from these questions—and they must supply some answers of their own. Raymond Rivas, an advisor affiliated with LPL in Atherton, Calif., says he has dealt with several clients who had immature children—adults in name only who remain a burden to parents and/or would likely squander an inheritance.

For example, there was the 60-year-old son of an 87-year-old client who threatened suicide if Mama stopped supporting him. Instead of giving the son yet another lecture on the value of a dollar, Rivas recommended an incentive trust. Beneficiaries of an incentive trust only receive distributions of funds after criteria set by the benefactor are met. “The incentive trust basically says to the child, ‘I’m going to give you incentives after I’m gone so you have a productive life’,” Rivas explains. Incentives can be structured in many ways. For example, the trust can reward the beneficiary with a dollar for every dollar he earns. Or incentives can be designed to encourage the heir to go back to college or start a business.

Rivas says the subject of the immature child is usually introduced by the clients. “They might say something like. ‘I give my son everything but he never thanks me.’ You ask them how they feel about giving the child money—and at that point you shut up and listen for the next 10 minutes,” he says.

Talking to a client about the financial implications of the death of a spouse requires a little tactful digging on the wealth manager’s part. Patricia Bell, a member of the advisory council and a wealth manager at Merrill Lynch, says some clients may worry that they will disgrace their deceased spouse by delving into financial matters too soon after the death, but there may be important financial decisions that should not be postponed.

Diane Pearson, director of financial planning at Legend Financial Advisors in Pittsburgh, says she recently started working with a client who came to her one year after being widowed. The client’s husband had left about $2 million for his wife and daughter in investments in individual stocks. “They hadn’t done anything with the investments because they assumed that he had worked very hard selecting the stocks for them,” Pearson says. Indeed, the husband had done a phenomenal job building the portfolio. “But that’s something that you have to watch every day,” she says. Just because it was a good portfolio when he passed away in mid-2005, doesn’t mean it was still in good shape by August 2006.

Some issues are less taboo, but still difficult to discuss. Getting the full picture of a client’s financial situation means finding out about any previous marriages. Bryan Lee, CFP, is president of Strategic Financial Planning in Plano, Texas. His advice is to broach the topic during one of the first meetings with a client. “The conversation starts just as simple as asking a couple if this is their first marriage. It’s a simple yes-or-no question,” he says.

Then you can immediately get into the financial and legal implications associated with previous marriages—most importantly: Are there any children from the previous marriage?

Blended families can pose tricky financial-planning challenges. One important rule, the Advisory Council members say, is to keep all the children well informed of inheritance plans. “There has to be a big family meeting with each set of kids, and you have to tell them exactly what the plan is. Otherwise you’ll guarantee a blow up in the family,” Rivas says.

His approach is similar to Lee’s—just ask the client if they have discussed the inheritance plans with the kids. “If they’ve hired me to take care of the assets, then those are conversations we have to have,” Rivas says.