If you aren't asking tough questions, you aren't doing your job

If you aren't asking tough questions, you aren't doing your job
Bringing up challenging topics with clients can be awkward and painful, but advisers need to become comfortable with the uncomfortable.
JUL 22, 2019

As fiduciaries, it's our job to push clients to think about uncomfortable aspects of their lives. To name a few: discussions around retirement and death, providing feedback on spending, estate planning, gifting to family members — or saying no to adult children. Bringing up challenging topics can be awkward and painful. Yet I've never lost a client for asking necessary questions. Advisers need to step up and become comfortable with the uncomfortable. This part of the job will never change: Every family faces difficult life decisions that impact their finances. Here are a few of my experiences– and key learnings. (More: Planning potholes and banana peels)

Laying the groundwork

My key observations: 1. If you serve in a fiduciary capacity, issues that present potential hazards to clients' financial security must be raised. 2. When raising a sensitive topic, it's important — and breaks the ice — to first ask permission to raise it. 3. Be patient; don't expect instant results. Clients likely need time to process any changes or new approaches. These kinds of decisions usually require follow-up and time. The client might need years to implement your advice and remedy the issue. 4. Warn clients from the get-go that you don't shy away from hard questions about their best interests. We call these "fearless conversations." During the first meeting with prospects, we describe these interactions as fundamental to the kind of advisory relationship we offer. (More: Milestone planning helps clients and advisers)

With family matters come intense emotions

I call it "the moment of truth": What you are about to say to a client will touch on powerful emotions that potentially could impact their most cherished relationships. Many sensitive conversations involve clients' immediate families. A particularly touchy topic is lending or gifting funds to adult children or other family members. Sometimes there's guilt involved, like making up for someone not being the "favorite" child. Or in the case of a blended family, one parent might feel strongly about a loan or gift, while the other might be resentful. In short, expect hefty family dynamics. As an adviser, you're not there to micromanage. Your role is to call attention when loans or gifts are putting your clients' financial futures at risk. You might suggest they include the gifting as a "goal" into their financial plan, so you can track it and make sure it remains sustainable. I always try to lead with the financial plan because it involves numbers — not judgment. My chief message is that I care about them and want to bring critical issues to their attention. Clients typically know when gifting is an issue and appreciate help with strategies and resolutions. Other sensitive topics include: • Reviewing estate plans. Pointing out inequities in outcomes following a death — and potential hardships for the surviving spouse. In one case, it took three years for a couple to finalize a plan that felt fair to both. • Overspending. If distributions going to a client are not adhering to their financial plan and are unsustainable, we need to take a deeper look. • Questions about a child's capacity to manage a bequest. Are safeguards needed? Should assets be kept in trust and a corporate trustee be appointed? (More: Calm in the storm: How advisers can combat emotional investing)

A deeper relationship

I'm happy to report that it does get easier, and virtually every time I've needed to ask the hard questions, the long-term outcomes have been positive. In the short term, emotions may arise — or not. Most clients recognize your courage in discussing profound, difficult issues. Invariably, your willingness to fight for their interests will deepen their trust in your relationship and your value to them. (More: When clients survive a mass shooting) Nick Strain is senior wealth advisor at Halbert Hargrove.

Latest News

The 2025 InvestmentNews Awards Excellence Awardees revealed
The 2025 InvestmentNews Awards Excellence Awardees revealed

From outstanding individuals to innovative organizations, find out who made the final shortlist for top honors at the IN awards, now in its second year.

Top RIA Cresset warns of 'inevitable' recession amid tariff uncertainty
Top RIA Cresset warns of 'inevitable' recession amid tariff uncertainty

Cresset's Susie Cranston is expecting an economic recession, but says her $65 billion RIA sees "great opportunity" to keep investing in a down market.

Edward Jones joins the crowd to sell more alternative investments
Edward Jones joins the crowd to sell more alternative investments

“There’s a big pull to alternative investments right now because of volatility of the stock market,” Kevin Gannon, CEO of Robert A. Stanger & Co., said.

Record RIA M&A activity marks strong start to 2025
Record RIA M&A activity marks strong start to 2025

Sellers shift focus: It's not about succession anymore.

IB+ Data Hub offers strategic edge for U.S. wealth advisors and RIAs advising business clients
IB+ Data Hub offers strategic edge for U.S. wealth advisors and RIAs advising business clients

Platform being adopted by independent-minded advisors who see insurance as a core pillar of their business.

SPONSORED Compliance in real time: Technology's expanding role in RIA oversight

RIAs face rising regulatory pressure in 2025. Forward-looking firms are responding with embedded technology, not more paperwork.

SPONSORED Advisory firms confront crossroads amid historic wealth transfer

As inheritances are set to reshape client portfolios and next-gen heirs demand digital-first experiences, firms are retooling their wealth tech stacks and succession models in real time.