Starting the Philanthropic Conversation

The philanthropic conversation is one of the most valuable conversations an advisor can have. It is the single best way to engage the next generation, deepen client relationships, and grow the assets you steward. And it is the rare conversation that has nothing to do with markets, which is exactly why it matters.

Here is the thing most advisors already sense. Your clients made their money to do something with it. They are already having conversations about what their wealth is for, around the dinner table, with their kids, in quiet moments. The only real question is whether they are having those conversations with you, or without you.

Why it feels hard

If raising philanthropy feels awkward, you are not alone. The discomfort is almost universal, and the data says so:

• 77% of advisors cite a lack of expertise in advising on philanthropy.
• 67% say they do not adequately understand structured giving.
• Very few feel genuinely confident bringing it up at all.

It is not a failure of skill. The conversation just sits outside the usual script. If your relationship is built on returns and planning mechanics, pivoting to the "soft stuff" can feel out of place, or out of your lane. So it often does not happen:

• Advisors wait for the client to raise it first.
• Clients wait too, assuming their advisor is not interested or not equipped.

One recent study put it perfectly: advisors and clients are ships passing in the night, both wanting the conversation, neither able to connect.

The most common trap: opening with tax

When advisors do raise it, many lead with the technical angle, the deduction, the vehicle, the strategy. The data says that is backwards:

• 40% of advisors think tax is what drives giving. Only 21% of clients agree.
• Clients say their real motivators are making an impact and that it feels good.

Open with tax and the conversation feels transactional. Open with the client, and it opens up.

You do not need to be an expert. You need a way in.

You do not have to become a philanthropy specialist to start. You do not need to know every vehicle or every charity. You need one good question, asked with genuine curiosity, and the willingness to listen.

The best opening questions share one quality: they start with the person, not with charity, tax, or mechanics. They are high-altitude. They invite a story, not a number.

Here are three that work.

1. "Beyond your family and your business, what kind of impact would you like to have on the world around you?"

This pushes the client past what they have already worked out for family and business, and into territory they may never have been asked about directly. It surfaces latent intent, sometimes about their community, sometimes a specific cause, sometimes a quieter sense of legacy. Of the three, this one is often the most revealing, precisely because no one has asked it before.

2. "Have you and your family had explicit conversations about giving back? About what causes matter, why they matter, and what you'd like to do together?"

This surfaces a gap most families do not realize they have. Vaguely supporting a handful of charities is not the same as a shared conversation about what the family stands for. The answer almost always reveals whether there is appetite to bring the next generation in, which is the conversation that protects the relationship across a wealth transfer.

3. "If you were to be more intentional about your giving, making it part of your overall plan rather than a series of one-off decisions, what would have to be true for that to happen?"

This is the qualifier. The client either says "I have not thought about it like that," which is the moment they start to, or they name what they would need to make it real, which hands you the roadmap to the next conversation.

Let the questions do the work

You will notice these questions do not require you to have any answers ready. They require you to be interested.

Think back to when holistic planning first took hold, when tools like Conquest pushed the conversation past products and returns toward goals, values, and what a client actually wanted their life to look like. Asking "what do you want your money to do for you" felt soft at first, almost outside the job. Now it is the job. The best advisors became the ones who could ask the open question and listen to the answer.

The philanthropy conversation is the same muscle, pointed at a new question. You are not learning a new skill. You are using one you already have. The client's answer will pull the conversation toward the specifics, the causes, the family, the capacity, and that is where the real work begins.

What comes next

When a client engages with these three questions, you have opened up the three dimensions that matter: their values, their family, and the structure of their giving. The natural next step is to turn what surfaced into something real, a philanthropic plan that captures who they are as a giver and what they want their giving to do.

That is the moment the conversation stops being a nice exchange and becomes part of the value you deliver. Tools like WellAdvised are built to take what surfaces in that conversation and turn it into a structured, shareable plan. You do not have to have all of that figured out before you start. You just have to start.

So before your next client meeting, pick one of the three. Ask it, and listen.