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A Review of Digital Executor: Unraveling the New Path for Estate Planning

By Jason Moyse.

“We live in the digital era, where technology has transformed how we communicate and engage, even how we die.”

That’s a key line from Sharon Hartung’s second book, “Digital Executor: Unraveling the New Path for Estate Planning”.

Sharon’s background is as impressive as she is humble which is to say, vastly measured. As a professional engineer, she has an extensive record in IT project management and consulting, having built and maintained large enterprise systems for both public and private sector clients as an officer in the Royal Canadian Air Force, retiring as captain before joining IBM Global Services where she went on to a further illustrious run leveraging her plethora of degrees and certifications for real world execution of complex projects.

She has now moved on to an exemplary encore career which is fascinating and a service to others as she is a member of the Society of Trust and Estate Practitioners (STEP) focusing on digital assets and the “death positive” movement. Her prior book was a consumer primer titled “Your Digital Undertaker: exploring death in the digital age in Canada.”.

Her latest offering is focussed more broadly than her home country, and aimed less at the individual “consumer” with the intended audience being the estate advisor community which includes a broad swath beyond just traditional lawyers, tax and wealth professionals and in fact, increasingly, a technology lead set of practitioners as well. Her laudable and stated intention is to raise awareness of estate advisors relative to the impact that their clients’ digital footprint has on estate planning.

Sharon usefully delineates between estate advisors and service providers. Estate advisors include the professionals referred to above that are involved in varying measure with estate planning and administration. This can also include insurance advisors, financial experts, trustees, advisors and agents of fiduciaries and increasingly, technology professionals to say nothing of the numerous funeral/death care professionals who have deep expertise in addition to their deft skills managing the ultimate in human and emotional circumstances. Service providers are those businesses, organizations and entrepreneurs who provide technology, platforms and services that allow consumers and businesses to interact online.

There can be little doubt that this book is needed for its practicality, prescriptiveness, and overall snapshot of the current state of play related to death planning and digital legacy. It’s a service to all providers which should capture the attention of many, and if nothing else, the reader is left pondering next actions in respect of their own affairs!

I’ve known Sharon for a few years through my work as a board member at Directive Communication Systems, a platform for estate advisors, service providers and consumers that records digital property, online account and final directives to ensure digital property is visible, accessible and maintained while preventing digital content providers from locking out estates or deleting data. Information is stored with clear and binding user directives without using passwords.

In my experience, Sharon is not one for click-bait bombastic prose, even when she points out that more people die from taking selfies than by shark attacks on an annual basis. She’s fact based and a voice to be extensively trusted.

Perhaps she should be more “bombastic” or actually “brotastic” akin to much of the nonsense VC-backed, PR-astute startup entrepreneurs who publicly celebrate high-five fundraises, hiring “wins”, and “our mission is holier than thou” content.

Being a great marketer is a key skill, but let’s not trump (note little “t”) actual expertise with unbridled exuberance and potentially misplaced confidence. Sharon’s message is rich with practical insight on handling a pervasive yet mostly invisible challenge. It deserves attention.

There is little doubt that a confluence of factors are happening including the greatest intergenerational wealth transfer in history, coupled with software eating every industry and as Sharon posits, acceleration of all things digital in the estates space via the Covid pandemic.

However, a description of all things digital can and should be further edified as between transformation of delivery of traditional services, emergence of new services altogether, and, of particular interest, the birth of an entirely new class of (digital) assets.

As an example, entrepreneurial will and estate planning providers went with the “do it yourself” model sometime ago with paper based “will kits” which you could buy, believe it or not, at your grocery, pharmacy or hardware store. Most of those kits were “good enough” for low complexity estates. They were often challenged vociferously by lawyers, particularly amongst solo and small firm practitioners, as not only an unauthorized practice of law, but dangerous for the consumer. There are likely survivorship bias examples of people that would have been better served with traditional lawyer driven assistance, although much more expensive. On the whole however, good enough would be good enough for most and perfunctory execution is often sufficient to cover the needed bases.

That area has evolved into other delivery mechanisms which align with the times via on-line and digital offerings from companies like U.S. based Trust & Will, or Canadian based Willful, who are each enjoying impressive growth and have astute marketers at the helm. These offerings are likely sufficient for most modestly simple estates and are an evolution on the delivery of a service. In some instances, there is no such thing as a “digital will” and a glaring gap for electronic wills registration depending on legal jurisdiction. It stands to reason as an entrepreneurial bet, everything is changing.

However, digital delivery for estate planning does not necessarily equate to best practice in handling digital assets. Sharon provides helpful definitions from an array of sources in describing digital assets encompassing on-line accounts, photos, videos, social media, intellectual property, and perhaps emerging crypto based currency.

There could be sentimental as well as financial value attached to one’s digital footprint and in a gift of succinct summation, Sharon asserts that digital assets are your memories, money and records in digital form. Put more formally, digital assets that are owned by clients have varying rights to use (perhaps by licence) or access. They may be stored either on servers (on-line) or personal computing devices and forms of hardware.

Then of course there are email accounts which are both an asset on their own, but also the key repository for information about physical assets, debts, liabilities and other on-line accounts, as well as key relationship information regarding personal and financial matters. Increasingly, accounts like Google and Facebook are also the conduit to other online services by way of two factor authentication as a login credential – beyond just username and password – to gain access to other digital accounts and services.

So if an email or social media account are digital assets and part of the estate plan itself, what if beneficiaries or fiduciaries can’t access the account of the deceased account holder? For that matter, the entirety of a digital footprint or portfolio of digital services are not necessarily going to be discovered, and even when found, aren’t necessarily accessible with or without a will.

Before reading Sharon’s book, I had two key thoughts around digital assets and estate planning and unsurprisingly, she covered both in well articulated fashion based on an entire adult working life spent in technology. Those thoughts are primarily that there is a Y2K styled cliff ahead, which may not transpire in the benign fizzle of the original and in fact, has woefully insufficient attention being paid to it (much like climate change now being visible after decades of clear warnings). At the same time, this era of contemplation around digital asset management is akin to circa 1995 web life.

In the beginning of any changing tide, there is always an overabundance of fear, uncertainty and doubt. Simultaneously and on the flip side, as any personal development expert will tell you, justified excitement and unnecessary fear are often experienced in the exact same way.

The beginning days of web around the early to mid 1990’s were such a period. Everyone knew something big was happening, world changing in fact, and yet we had to endure wildly varied experiences which at times bordered on the comical. The idea of a web page was a static brochure on a screen, rather than a way of dynamically performing a service. Not only were the experiences varied in their quality, so too were the entrepreneurial ventures wrapping around the web in both underlying infrastructure and front end presentation. It would have been impossible to know which business would survive, including the original Amazon selling books over the internet.

That’s the era we are currently experiencing in relation to digital assets as a class and the delivery of services around estate planning. A rush of organizations (and venture capital) are bringing life to the death industry. For example, Trust & Will boasts 200,000 customers with a 300% year-over-year increase in transactions and a more than 250% increase in site traffic, to say nothing of a $15M (USD) Series B venture capital round in 2020. They also have partnerships with organizations like the American Association of Retired Persons which is a 38 million member organization with billions in revenue and among the largest circulation of publications in the U.S.

Also of note, and more germane from a digital asset perspective, is their partnership with 1Password, a leading password manager which allows for inventory of passwords which are in turn protected by a single password. Such a vault is capable of being shared with others even if that is not necessarily a good idea. The challenge however, is that mere password sharing is not estate planning. Passwords are not needed at all for the proper transition of digital assets. In fact, it’s not advisable although it remains go-to advice from all kinds of estate and service providers who ought to know better.

So what is the invisible tsunami part of the narrative?

The average number of digital services aligned to a single individual is growing exponentially as is the amount and value of data being held. In terms of what happens upon death or incapacity, very few on-line service providers, known as Custodians, have legacy settings (like Facebook) or inactive account management tools (like Google) or a Digital Legacy Program (coming with Apple iOS 15).

For the hundreds of other accounts aligned to an individual without such mechanism, absent a properly executed direction, the terms of service of the site provider Custodian will govern. This is largely a function of the evolving legislation which in the U.S. is known as the Revised Uniform Fiduciary Access to Digital Assets Act (RUFADAA) requiring explicit consent from the account holder to the provision (or perhaps restriction) of access to digital assets, falling which, terms of service reign above all else.

As I presented at the 2019 LegalGeek conference, password sharing is not an effective strategy for digital asset estate planning as that is essentially impersonation. With a properly executed directive, passwords are not required.

Part of the dilemma is that otherwise, power rests with Custodians and their terms of service which you couldn’t reasonably review for all of your accounts and even if you could, you wouldn’t be able to bargain away any of the terms or negotiate for additions. Today, some terms of service indicate that an account is non-transferable and terminates upon the user’s death. On the whole however, at present, 85% of site owners do not have any terms that address incapacity or death of the account holder in any meaningful or explicit manner.

The tsunami ahead is also the deluge of lost assets in the coming years as the uptake of the proper transfer mechanisms where they do exist will remain low, and more likely, most beneficiaries will rely on their estate advisor to uncover assets. It’s not unreasonable to imagine aggrieved beneficiaries suing their estate advisor(s) for not assisting the decedent in proper planning to provide access to assets from numerous digital accounts.

Most of the time, decedents are likely to leave the fiduciary and beneficiaries in the dark about their digital life unless the advisor follows a number of the prescriptive strategies, tactics and tools outlined in Sharon’s book. You’ll have to read the book to find precisely what those strategies entail.

An awakening has not really started as noted by Sharon. Among corporate trust companies and fiduciaries, an alarm bell is not yet ringing. It may manifest through demographics shifting as current retired and retiring generations transition to a more digital native cohort. For the present however, consumers, estate providers, service providers and Custodians are still mostly sleeping.

I have such an affinity for Sharon’s world view, that I have to stretch to find where I can take an opposing perspective. Regrettably, it’s in her optimism on the universe unfolding as it should. Throughout the book, Sharon suggests that as cases of lost or inaccessible assets mount, and awareness of consumers grows, the demand placed upon estate advisors, service providers and Custodians will require them to change their practices and operating models and they will be forced to stop relying on myths (i.e. password lists) to accommodate the legal and digital reality.

As I surpass 20 years in the legal industry, I’ve watched the billable hour persist despite its obvious disincentives for efficiency and commercial unreasonableness. Change is not inevitable and the timeline is not fast despite accelerants, even when the purchaser shouts from the rooftop. Incentives and interest drive everything and just as lawyers and law firms lack interest (and obviously incentive) for change -- so too among Custodians who have to protect the rights of all of their users (living and otherwise).

NetChoice, the primary public policy advocacy organization that promotes internet innovation and online commerce with all of the main Custodians as its members, holds the position that estate planners and others risk liability and criminal punishment when advising clients on the improper use of passwords to protect their digital assets and online accounts. Despite this, the member Custodians have failed en masse to meaningfully shift their terms of service to address account holder incapacity or death.

Sharon’s prowess as a project manager, particularly related to technology, no doubt seeps into her outlook on everything. This is an affliction from which I also suffer. At times, she postulates that what’s needed either from an advisor, beneficiary or decedent (while living) is to keep evergreen plans and checklists updated, tested, backed up and and managed on top of having a personal plan akin to the business context with a succession plan for home IT, including dry runs.

To have such a highly structured mindset, even for personal rather than mere business matters, is an outlier among most of the populus as it is very difficult to get traction with large swaths of people to follow in both intention and deeds. The vagaries of humanness get in the way and despite its rationality, too often, life is handled in messy fashion notwithstanding excellent advice like Sharon’s is available. People don’t think and act like well-reasoned project managers quite so pervasively unless they are freak flag fliers like Sharon and I. All the more reason for people to rely on advisors.

To seek out anything further from Sharon’s book which would be ostensibly worthy of deeper critique is overextending beyond the bounds of that which is her strength, well articulated reason. This book is required reading for those in the business of law, wealth, finance and technology planning, wherever digital assets are in play, that could form part of one’s digital legacy and footprint. The corporeal may end, but the digital does not.


About the Author

Jason Moyse is a Board member of Directive Communication Systems. His primary focus is working on behalf of Autologyx, a no code process workflow automation platform servicing corporates and professional firms in support of managed services. He is also the principal of Law Made, focussed on digital and legal operations, business design, process and technology. He is a frequent keynote speaker on legal innovation.

#JasonMoyse #bookreview #digitalassets #estateplanning #legaltech

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