The Executor Selection Framework
Your executor is doing your final tax return while grieving — pick someone who won't buckle under both.
The executor is the person who administers your will after your death — locating and liquidating assets, settling liabilities, managing trusts, filing tax returns, and distributing the estate to beneficiaries. The role is legally complex and emotionally gruelling. Sam Grice's framing is precise: it is like doing someone's final tax returns while also making decisions on financial assets and pensions, while grieving.
Most people default to naming a spouse or child as executor because of trust. But trust and competence are different axes. A partner who is grieving and has never navigated probate, pension redemption, or trust administration faces a compounded challenge. For estates with business interests, crypto holdings, or structured trusts, the stakes of errors are high — tax miscalculations, mis-distributed assets, or trust terms applied incorrectly can cost beneficiaries significantly.
Grice recommends a two-executor model: a professional executor service (or a financially competent personal contact) who does the administrative grunt work, paired with a family member who has oversight access. This separates the competence burden from the trust burden. The family member can verify that the professional is acting in line with the wishes expressed in the will; the professional handles the technical execution. Neither party is carrying the entire load.
- Trust and financial competence are separate criteria — your executor needs both, and you should assess them independently.
- Naming a grieving spouse as sole executor combines the hardest emotional state with the most demanding administrative task.
- A two-executor model — professional plus family oversight — separates competence from trust and distributes the burden.
- Business owners and crypto holders should treat executor selection as a specialised hire, not a personal appointment.
- The executor should know they are named, understand what the role requires, and have access to the asset map before death.
- Assess your estate complexity honestlyList what your executor will need to do: locate and liquidate assets, deal with crypto access, file tax returns, administer trusts, handle business equity. If the list includes anything beyond straightforward bank accounts and a property, treat executor selection as a specialised appointment.Pro tipAsk yourself: if this person received no guidance from me and had to start from scratch, could they navigate this estate without professional help?WarningDon't overstate complexity to justify a professional — simple estates genuinely don't need one. But don't understate it to avoid an uncomfortable conversation.
- Separate your trust list from your competence listWrite down who you trust most and who is most financially competent in your network — these may not be the same people. The ideal executor appears on both lists. If no one does, use a professional executor for competence and a trusted family member for oversight.Pro tipFinancially competent does not mean wealthy — it means comfortable navigating tax returns, investment accounts, and legal correspondence under pressure.
- Name a primary executor with a designated oversight partnerStructure the appointment so the primary executor leads on administration and a second person — typically a family member — has visibility into the process and can flag concerns. Even professional executor services like Octopus Legacy recommend this pairing: 'We do the grunt work; they oversee.'Pro tipGive the oversight partner explicit permission in the will to review the executor's actions — this formalises the relationship and prevents disputes.WarningAvoid naming a primary beneficiary as sole executor without thought — the conflict of interest is not illegal but can create family tension.
- Tell your executor before you dieConfirm with your named executor that they are willing and understand what the role entails. Share the location of your will and asset map. A surprised executor discovering their role at probate starts at a disadvantage the deceased created unnecessarily.Pro tipA brief conversation — 'I've named you as executor, here's what that means, here's where my documents are' — takes 20 minutes and saves weeks of delay.
The host initially wanted to name his co-host as executor for financial competence, plus his partner as beneficiary. Sam Grice walked through the options — naming two people, with the co-host leading on administration and the host's father providing oversight.
The episode co-host, who owns multiple limited companies, explains that his own will required more complex executor provisions — someone who could handle the equity stakes and 'key man' implications without the business being disrupted by a grieving partner who 'doesn't know anything about this business.'
Octopus Legacy offers professional executor services, and Grice's experience running this service repeatedly surfaced the mismatch between who people nominate as executor and what that person is actually equipped to do. He specifically observed that business owners, investors with complex asset structures, and anyone with crypto were consistently selecting executors who lacked the financial literacy to administer the estate correctly — not because they chose wrongly, but because they defaulted to trust rather than assessing competence.