Join Tom Deans as we discuss why you need to share your will with your family.  We’ll go much further than just sharing your will.  Tom will tell us about why you need to have your family co-create your will with you.

Here are some things we’ll discuss:

  • Why you need a will in the first place.  You do have a will don’t you?
  • What a family meeting might be when it comes to sharing your will.
  • How to get the elders in your family to share their wisdom and why wisdom is more important than money.
  • Where transparency fits in with the healthiest of families.

Tom has become one of my favorite authors and thinkers.  He’s also the author of Every Families Business.  To learn more about Tom click here.


Today’s podcast features author of Time games. Tom Deans has spent his life in and around private businesses. In his first book Tom questions common wisdom whether it’s wise to give the family business to children, instead of having them buy it. In the second book, in the one we’ll be discussing today Tom talks about the need for family to have deep conversation about the wishes of elders when it comes to estate planning. We’ll be learning about why having an annual family meeting leads to healthy family relationships that last generations. So let’s get right to it.

Josh: Hey Tom, how are you today?

Tom: Josh, I’m very well, how are you?

Josh: I’m great, thank you.

Josh: So tell me what’s that wisdom all about and how did you end up writing it in the first place?

Tom: Well Josh, I think anyone who writes the book is trying to convince themselves of an idea and not the reader. And that held true to me personally and it definitely held true for the second book. I have been both and inheritor and a will gift significant estate. And I like anyone who has gone through that process has really been recipient of an amazing gift. I come from a family that has a really quite odd financial transparency.

We have found that in our culture to that not only have annual family meeting and even more regular meeting than, that embracing lots of discussion and openness transparency and kind of Socratic approach to asking questions of our children and then as we age and kind of strip away about finances and personal finances and money and who will inherit how much and when and what.

And that’s really what willing wisdom is about, it’s about to offer seven questions to help families bring some shape and form to that awkward, awkward conversation about money and aging and dying.

Josh: So, I know you want people to buy the book but what would you say is the most important question observant people need to answer?

Tom: Oddly not, I think it’s the last question, it’s really a question that deals with last wishes. Which on a surface looks like a money question but it’s not. But it is a question that I think most families avoid.

We know that a 173 million American adults have no will, they have no legal will. So we know that in the absence of a will there is really lots of ambiguity around how someone’s life will be celebrated. So in our family meetings we deal this head on, we have copies of our parents wills, they have ours. There’s nothing that says that I’m not going to predecease my parents. So there’s lots of sharing of legal documents. So that everybody kind of knows who the executors are, who will be in that position to way in and execute our wishes around our last wishes and how we’re celebrated.

It is unbelievable how families will tear themselves apart trying to figure out in the absence of a will how mom’s and dad’s life should be celebrated. It seems basic, it is often not the expensive family asset that divides family and sibling relationship after mam and dad die, and it’s often emotional subjects like funeral and how last wishes are celebrated.

Josh: So, has your family delineated how you’re going to do funerals and memorial services and end of life issues?

Tom: Well, we have in great detail. And you know as I taken this book on the road and worked with other kindred souls working with individual families typically significant families it is absolutely amazing. You would figure that billionaires have this stuff buttoned down but it is unbelievable, I would argue that the more the wealth and assets that their family have accumulated, the more difference that they put between their family and relationships around subjects like last wishes or advanced health care directive.

How mom and dad wanted to be treated by health care professionals as they are aging and losing control. So again you would think that the better planner you can buy the better plan. I think it’s quite the opposite. And you only have to look at the great figures in history, people like Robert F. Kennedy, who when he takes the bullet for his country in 1968 is assassinated in Los Angeles, good news he has a will, bad news he has his brother John as executive of that will, who was of course assassinated in 1963. So the rich, the famous, the powerful are prone on making some of the biggest mistakes in the estate planning. So the great lesson for all of us that you can’t buy this plans, we all have to work on them with our family in relationship in conversation today when we’re thinking clearly.

Josh: So, this is interesting. You think that the more money somebody has, often less they talk to their family. Why do you think that’s true?

Tom: Well, we know from the data that people who amount significant wealth particularly business owners, the first rule of business is about control. Right? So when you’re the majority share-holder, whether you’re the founder or not, if you’re the controlling share-holder you get to exercise control. That is what we learn and that is what teaches us how to accumulate wealth.

And that very principle is often what creates great problems in estate plans. Particularly as we age we seem to think that control is at the center of the greatest safe plans but in fact is actually relinquishing of control. So watch from the people who don’t have much wealth but never had a culture of exercising control actually find giving up control pretty easy. So the act of ageing and dying is the ultimate act of control, it’s where we rely on those which we forge deep relationship on trust and respect. Those – have great depths, this idea of relinquishing control. So the great business owners that have mastered this.

Josh: So to the people who are listening and might recognize, when we were talking about have to be in control themselves, what kind of advice would you give them?

Tom: You know, the great patriarchs and matriarchs, and I use those words knowing that many listeners will be unfamiliar with them or have a clear sense of what it means. We lost the cultural familiarity of what it means to be a great patriarch and matriarch. The great ones, the ones that have really let their generation to become an even greater dynastic family, have something in the family culture that give them a signal on a point in time to create space around them for their prodigy, especially prodigy to not just become good as them, but they take it upon themselves to make their prodigy even better.

And there’s graciousness and humility that drives this kind of wisdom. And what they are teaching and preparing their heirs is something that transcends money. It is about ideas and creating a sense of chosen being whole and true to themselves to pursue that which is real to them. And in many cases that is different than running the same business, it means being real and that sometimes means taking a family on a different direction and taking different kinds of risks with family money.

When we as patriarchs and matriarchs take away that space and try suck all the oxygen out of the room because of our own greatness and magnificence, we get the kind of family legacy that we deserve which are the ones that collapse under the burden of trying to replicate what is already been.

Josh: So, what you’re saying or what I’m hearing you say is you really have to let the next generation take their own path. And having that conversation make a richer life.

Tom: I think so, and I think that that seems pretty straight forward but that being informed by matriarch or patriarch that shares just not only the wisdom of life lessons that have gone well for the family but the hard part where someone, a family has pulled up significantly short or has made a serious mistake, those are the greatest gifts of all.

Those are the pools of wisdom that helps the next generation from making the same mistakes and to become better. And that’s what I alluded early it’s those kind of gift that have nothing to with money or clever tax plans or legal structures but everything to do, as I said, with culture of learning and culture of teaching. And hoping for more and hoping quite frankly for someone to continue your work.

Josh: So tell me, how would you get that conversation started? It seems pretty challenging to me.

Tom: Well, I think this is hard and this where I have great help in a form of advisers, sophisticated advisers, who hold a family meeting in an idea of a family meeting is not a natural one to a family. To hold the family meeting, I think that’s huge. I think that is such a culturally difficult conversation to start it just fits the role of adviser. And I’m not an adviser, I don’t do that work but there are thousands of qualified people like yourself that can do that kind of work. That can start that conversations and shape that conversations and bring intergenerational view of wealth management.

I think family has always been at the center of wealth management. It’s not about getting 20 % of return on invested capital it is about getting a good return on your invested money, but also rapping some purpose around that so that it releases potential in the next generation. Who’s starting that conversation? It’s not family, it’s advisers, the best advisers.

Josh: What advice would you give to an adviser and how to approach this subject if he feels uncomfortable doing so?

Tom: Well, I think the best way to do it is to talk about their own experience. And I got to tell you Josh, I was speaking in Chicago not long ago, about 6 weeks ago and I had a room full of financial advisers and half of the advisers in that room did not have a will themselves. So they are incapable on drawing on their own narratives, to share their own difficulties in starting with this conversation with their own family.

They can’t relate to their clients because they haven’t done their work. See that’s really crucial. Advisers need to share their own personal struggles in starting family conversation around money, ageing and dying. That’s when they grain trust and respect and credibility.

Josh: So what you’re saying is first advice is better get themselves a will and all the other stuff that goes along with it. And second, they really need to be having their own family conversations.

Tom: Well absolutely. They have to go with the next step which is controversial part of the book. And that is, that it’s not just enough to right a will, it’s really all about reaching out and writing the will work together with intended beneficiaries. I don’t understand how we can write will without seeking the knowledge and wisdom from recipients, intended beneficiaries. It makes no sense to me.

Why we hoard our wisdom and our desertions and leave it to when we’re dead. And our beneficiaries finding out what happens, how it goes down in some lawyer’s office. Where people have lots of questions and the person’s dead. So it not enough just to write the will, without collaborating on that will and sharing the contents of it while you are thinking clearly.

Josh: Interesting. So, something which I find interestingly is an idea about: mom and write a will, they bring their kids and they have a conversation. And the kid’s kind of shake their heads “yes” about mom and dad are saying. But you know the kids really are not in favor or agree what mom and dad are doing. How do you bring this stuff out? How do you have a positive conversation about that?

Tom: You know all I can talk about is our own experience. We use a series of questions in our own family loosely, at times more formally. And I have to make a point right now Josh that some of our best family meeting aren’t around the table with advisors but around the camp fire. You know that are informal. You have someone saying: “You know I want to bring everyone up to date but before I talk about my will I have a couple of questions. How kids do you think I came to have money, how do we came to be where we are with our finances?” And listen to how kids respond, seek their ideas, ask them what they would do if they inherit it, ask them how much money they need to satisfy their material wants. Ask them about their profits, desires, find alignment, find areas where’s disagreement.

Explore both of them. You know it’s not about everyone nodding their heads, this is hard difficult stuff but let me ask your perspective Josh… there are worst problems in this world than dividing wealth, this are the kinds of problems we want and need. So often we lose perspective, and again I would turn to the advisers to bring this perspective to families that are talking about this stuff. And the kids are ill prepared and I met some. I’ve met kids who if they inherit 100.000 $ they will be dead in 30 days because of their addiction. So why not explore that and find out what kind of instruments, financial products and services are in place to release potential when children are healthy. Similarly I see kids that inherit 100 million $ and turn it into a business because they are smarter and harder working that dad.

Josh: I would agree with that 100%. So most advisers probably don’t have the skills to have this deep, deep conversation. What would you recommend to them?

Tom: There are dozens and dozens of books on transition of family wealth but you can make this an academic discussion or you can make it existential. Advisers don’t ask their clients anything they are not prepared to do themselves. Go through this process of discussing with your own families. Respect that your client may have more wealth but the same issues. We are all concerned about our own children learning how much wealth we have. But I can tell you right now, our kids – we have two kids in college, they are almost in their last year of college, but look at our kids they both have copies of our will and both exactly know what our personal net worth, they know our advisor, our advisor is their advisor and my advisor is my father’s advisor.

We bring a kind of intergenerational view on our wealth and our advisors have a complete holistic inter-generational view on how our money was earned, which btw was very slowly, with taking lots of risks and never a straight line up. And that is important to our family that someone, our advisers have long historical view of our wealth. I think our advisers are the keeper of our family stories and we count of them to tell the stories.

Josh: What would be your number one piece advice you would give to a family about their wills?

Tom: That would be, don’t try to write the perfect will and don’t view it as a static document, it is a living document; the document that can be changes and almost certainly should be changed. I review along with my wife our will every year and almost not a year goes by that something doesn’t change. Or our financial situation, had my brother in and out of my will a couple times not because my relationship has changed with him, he has moved, he moved to U.S., he moved back to Canada, so as guardian that decision changes with his location. It is unbelievable how much can change in a year and that has to be reflected in a will. And I have to tell you that in the absence of that, when executives have predeceased the person writing the will, or if we pick executives that are much older than us, they often die. We have to keep these documents current. My number one purging would be to review the will don’t view it as a depressing document. View it as a document the most important written word that you leave behind that informs people what you really believe and thought about the relationship and about your hope for humanity.

Josh: So Tom, if people want to find your book how would they go about doing that?

Tom: It is as easy as clicking on

Josh: Well that’s pretty great, so we’re at the end of our time and I thank you so much for talking with us today, as always it’s fascinating stuff.

Tom: Josh, the pleasure was mine.

Josh: Thank you.

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