It is the holiday season – a time of bright decorations, sweet treats, and ugly sweaters at festive occasions. But as we all know, a hero’s work is never done, so before you sign off from advising for some well-deserved personal time at the end of the month, here are four important conversations you should prepare to have with your clients in 2023.

How do you feel about your investments and the strategy we put together?

By keeping this question rather vague and open-ended, you give your client an open floor to talk about what matters to them to ensure a personalized experience. They may be concerned about how macroeconomic events might affect their portfolio or unsure of what to focus on in 2023. Once you understand their concerns or questions, you can walk them through what industry professionals believe and show them their portfolio in real time. Maybe a client expresses interest in increasing their charitable donations in 2023, which opens the door to discussing tax optimization and sustainable investing (for a good example of how sustainable investing can go hand-in-hand with charitable donations, check out this recent blog post). Taking the time to listen to their priorities and concerns will give you opportunities to personalize how you support them moving forward.

What are your plans for 2023?

You will never know if you don’t ask! Even though studies show clients tend to assume that their advisors can help them with many aspects of their financial lives, they often don’t think to bring up future plans with their advisor.1 Through active listening to your clients’ future plans, you may identify opportunities for goal-based planning, tax optimization, and even ways that to provide new services like credit, healthcare, or insurance support. Such conversations help clients to feel heard and supported, while also helping to enable advisors to deepen relationships and grow their business.

How do you feel about your estate plan?

The “great wealth transfer” is here and likely top of mind for more of your clients than you might think. Even if they haven’t brought it up, ask if your clients have a will, estate plan, or trust. If so, have you had a chance to review it? When was the last time it was updated? If not, that may be a good goal for 2023! In addition to making sure their financial house is in order today, these types of questions may help your clients to prepare their family for tomorrow.

Who else should we bring into these conversations?

Research has shown that only 13% of affluent investors choose to work with the same advisor their parents used.2 Simply engaging with multiple generations within a client’s family, even briefly, can help you to build those relationships and retain clients. A good goal might be to find ways to meet and/or interact with one additional family member each year, starting with spouses and adult children.

These types of questions help you to focus on what’s most important: deepening client relationships, delivering more personalized portfolios, and growing your practice. Remember – while your holiday sweater may be ugly, your clients’ finances shouldn’t be. Prepare now to help your clients live an Intelligent Financial Life in 2023.

In the spirit of holiday cheer, the Envestnet Ugly Sweater Builder contest is now open! Embrace your inner designer and send in a submission today. Envestnet Clients who win will be chosen 12/26 and will receive their custom knit sweater. Join in the fun!


  1. “Market Insights 2022,” Spectrem Group,
  2. “The $70 Trillion Dollar Opportunity Understanding the Implications of Multigenerational Wealth Transfer,” Cerulli Associates,

The information, analysis and opinions expressed herein are for informational purposes only and do not necessarily reflect the views of Envestnet. These views reflect the judgment of the author as of the date of writing and are subject to change at any time without notice. Nothing contained in this piece is intended to constitute legal, tax, accounting, securities, or investment advice, nor an opinion regarding the appropriateness of any investment, nor a solicitation of any type.

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