For Entrepreneurs, Confidence in Your Advisers Is Your Most Important Investment
When your business and estate are at stake, can you really count on the people who are helping you? Trust in your team starts with asking the right questions.


If your estate includes private equity investments, operating businesses or intellectual property interests, I’d wager that you have asked about client confidentiality during every introductory meeting with a potential adviser. I believe that almost every wealth adviser, bank officer, broker, portfolio manager and trust officer has responded to your inquiry with the same assurances:
“Our clients’ confidentiality is one of our primary concerns. We do not disclose your information to any third party unless you request it. Our electronic communications are encrypted whenever they include sensitive, financial or confidential information.”
A leap of faith
Of course, these kinds of statements do not answer your question, do they? Perhaps, because what you seek is not an assurance of confidentiality but of confidence in that adviser. I wish it were easy for you to build confidence in your advisers. You must share so much information so quickly to obtain the financial, fiduciary and legal services you need. And it is almost a leap of faith when you engage a new adviser based on trust that they have not had time to earn.

Sign up for Kiplinger’s Free E-Newsletters
Profit and prosper with the best of expert advice on investing, taxes, retirement, personal finance and more - straight to your e-mail.
Profit and prosper with the best of expert advice - straight to your e-mail.
Sometimes, my trust company is hired after a single conversation with the prospective family as the directed trustee for a wealth transfer strategy related to a business transaction involving tens of millions of dollars. Almost invariably, it is an introduction by a trusted adviser that laid the necessary foundation for building that kind of confidence.
If you may soon be selling your share of a successful business or other highly appreciated assets, you must engage a team of experts with confidence in their abilities.
Many moving parts
For example, my trust company often serves as an independent trustee, so clients may obtain certain income and estate tax benefits, asset protection and other advantages through a sale involving a trust. But for any trust strategy to succeed, all the advisers serving a client must understand the many moving parts of these transactions to effectuate and preserve the intended tax and financial benefits. And while doing so, they must each employ established practices to safeguard the client’s confidential information.
The process to establish such a trust in conjunction with a properly executed business transaction will necessarily include dealings with a broad variety of parties: sellers and buyers (and their officers, employees and tax and legal advisers); one or more banks and trust companies, law firms and accounting firms (and their staff and associates); one or more brokerage or financial firms (and their staff and associates); and family members (either in the know or unaware of these activities). That is an abundance of essential and tangential people with access to confidential information at a very sensitive time.
Transactions that involve intellectual property, trade secrets and/or the sale of company stock or assets sometimes require complete secrecy. An inadvertent disclosure to customers, suppliers, distributors or competitors could alter those relationships and undermine established goodwill, confidence in supply and sales agreements, and even the negotiated features of the transaction itself, such as the market valuation and sales price. All the nondisclosure agreements in the world won’t provide effective security if some of these parties lack the requisite expertise to execute a multistep transaction or fail to follow standards and practices controlling disclosure.
Personal involvement is crucial
But how do you ensure that your proposed business transaction and trust strategy will be protected? You must personally involve yourself diligently in the selection process and rely on your instincts. There are certain steps that seem to fall into place all on their own, but only if you let them. Foremost is the selection of your advisers.
Your corporate transactional attorney or your trust and estate attorney is hopefully a long-term adviser. Usually, one of these two advisers will first propose establishing a trust to obtain a greater benefit from the sale of your company or other assets. So first, meet with both these attorneys together so they may explain the division of labor and outline the many steps to implement an irrevocable trust strategy as a component part of your transaction.
Often, but not always, this will be a “foreign trust” — so called because it is established under a state law outside your resident state. But, sometimes, the trust will be established in your own state if your state doesn’t impose an income tax, offers strong directed trust laws, and the strategy merely requires an independent trustee (usually a trust company rather than an individual trustee).
Questions to be asking
You may be able to rely on your trust and estate attorney to have the expertise needed to draft a resident or foreign directed trust and advise on its risks and benefits in relation to a business transaction. But this practice requires a working knowledge of corporate, personal and fiduciary tax law, the trust laws of multiple states, and how to structure business transactions that may require company reorganization and strategic tax elections.
So, don’t be shy about asking how many of these trusts they have established, how many have involved a transaction like yours, and to walk through the risks and benefits of the strategy and the chosen jurisdiction.
Second, ask for a recommendation for the trust company you should use. Choosing a store-front trustee or simply using your bank because they operate a trust company means that the adviser with the most direct and continuing connection to your trust assets — your trustee — may not even understand the terms of the trust instrument, much less have the expertise to preserve its tax savings and other benefits. There is a real difference between trust officers trained to administer a large book of personal trusts and a dedicated fiduciary team with a proven track record as a knowledgeable and effective administrator for complicated irrevocable directed trusts and the related business transactions.
Third, ask the senior adviser at the trust company to introduce you to the team. Their team should include a wealth adviser, trust officer, associate support officer and a portfolio manager, with a bench of analysts focusing on securities, bonds and alternate investments. Each of these experts has a role to play in the success of your trust, even several years after the transaction closes. But you must have confidence in more than their expertise. You also need their loyalty; their dedication to your interests over theirs; their ongoing partnership with your own legal, tax and accounting advisers; their ingenuity and proactivity in identifying opportunities through long-term planning; and their objectivity in assessing the risks and benefits of their proposals.
Finally, you need confidence in their commitment to protecting your confidential financial and personal information so it will never be shared without your permission or used to further anyone’s interests before your own. This last item, confidence in your advisory team, begins with a leap of faith and grows with the relationship.
Get Kiplinger Today newsletter — free
Profit and prosper with the best of Kiplinger's advice on investing, taxes, retirement, personal finance and much more. Delivered daily. Enter your email in the box and click Sign Me Up.

Timothy Barrett is a Senior Vice President and Trust Counsel with Argent Trust Company. Timothy is a graduate of the Louis D. Brandeis School of Law, past Officer of the Metro Louisville Estate Planning Council and the Estate Planning Council of Southern Indiana, Member of the Louisville, Kentucky, and Indiana Bar Associations, and the University of Kentucky Estate Planning Institute Committee.
-
Donating Complex Assets Doesn't Have to Be Complicated
If you're looking to donate less-conventional assets but don't know where to start, this charity executive has answers, such as considering a donor-advised fund (DAF) for its tax benefits and ease of use.
-
Travel trends you can expect this summer
The Kiplinger Letter Domestic trips will trump foreign travel amid economic uncertainties, though some costs are down.
-
Donating Complex Assets Doesn't Have to Be Complicated
If you're looking to donate less-conventional assets but don't know where to start, this charity executive has answers, such as considering a donor-advised fund (DAF) for its tax benefits and ease of use.
-
Think a Repeal of the Estate Tax Wouldn't Affect You? Wrong
The wording of any law that repeals or otherwise changes the federal estate tax could have an impact on all of us. Here's what you need to know, courtesy of an estate planning and tax attorney.
-
In Your 50s? We Need to Talk About Long-Term Care
Many people don't like thinking about long-term care, but most people will need it. This financial professional recommends planning for these costs as early as possible to avoid stress later.
-
Social Security Pop Quiz: Are You Among the 89% of Americans Who'd Fail?
Shockingly few people have any clue what their Social Security benefits could be. This financial adviser notes it's essential to understand that info and when it might be best to access your benefits.
-
Such Attractive Yields in High-Grade Munis Are Rare and May Not Last Long
According to this munis expert, the last time munis were this cheap was a brief period in 2023. If you kicked yourself for missing out then, you have a second chance now.
-
Financial Analyst Sees a Bright Present for Municipal Bond Investors
High-tax-bracket investors have an excellent opportunity to secure low-volatility, high-quality returns at yield levels rarely seen in over a decade.
-
I'm an Insurance Pro: How Not to Get Dumped by Your Insurance Agent
Your insurance agent or broker might show you the door if you do any of these five things. Being a good customer is about more than paying your bill on time.
-
Two Estate Planning Issues You Should Never Overlook
This estate planning attorney explains why proper asset titling and beneficiary designations make a big difference when it's time to transfer your wealth.