Family business advisors, like family businesses themselves, do not come in a one-size-fits-all package. Some come from a legal background, others may specialize in the psychology of family dynamics, while others may bring an expertise in strategic planning. Choosing the right one depends largely on your specific needs.

Nobody understands this better than Wealthaven founder Holly Isdale. In creating Wealthaven, Holly sought to fill a void by providing comprehensive family business advice by evaluating the complete picture, and then integrates business and family matters, prioritizes, and oversees or executes the plan.

With 20 years’ experience in top Wall Street investment firms, Holly has worked with senior leadership, philanthropic boards, and some of the wealthiest families in the world.

Recently Holly joined Ramia El Agamy and Amy Katz to discuss the intricacies of selecting a family business advisor and the common pitfalls to avoid in this process.

This episode of Conversations with Women in Family Business is co-produced with Amy Katz, founder of coaching-business Daughters in Charge.

Featured picture by Markus Spiske on Unsplash

Picture courtesy of Holly Isdale


An Interview with Holly Isdale, founder of Wealthaven

Ramia: Welcome back everyone to another episode of the WIFB podcast together with Amy Katz from Daughters In Charge and today we have a special guest, Holly Isdale who was the founder of Wealthaven. Thank you very much Holly for joining us today.

Holly: Thank you so much.

Ramia: So today we are going to tackle a very interesting subject, and that is the question of when do women in the family business require their own advisor. So, when maybe you outgrow or require more specialized input into your career or into your progress from your own advisor and when can you stay with the family’s advisor? Holly, first of all though, tell us a little bit more about your own trajectory and why you are passionate about family businesses.

I started out as a corporate tax lawyer. I found that, in the course of the work that I was doing, and at the time, we were doing lots of mergers and acquisitions. I would find that when I was in on a deal or a negotiation, I was just so interested and drawn to the families. I really liked it the stories of the entrepreneurs that we were working with and I wanted to be doing more of that type of advisory work. So, I switched over to finance pretty early in my career. Over the course of the last 20 years I’ve led the estate and financial planning groups for JP Morgan, Goldman Sachs, Lehman Brothers and Bessemer Trust. I started my consulting practice in 2010 in large part because I was so frustrated by the fact that when you are working with a financial advisor, they’re selling a product. My services were tied to the investment management products which might not have been the best ones for the clients. And so, I actually started the business because I had phone calls from clients who kept saying I just need you, will you please come and restructure my family office. Help me fire an advisor, help me hire an advisor and that’s where I am. So now my consulting practice really works in three areas. I work extensively with families and family-owned businesses on issues of governance and succession and I can help in education because of my background in finance and law and trusts. I get called into families where there’s just this sense of I really don’t know what I have. I’m trying to get my arms around it and the different issues. I like making things orderly and less chaotic. I set up and run family offices because many times in working with a family, they need a dedicated quarterback or someone on their side of the table. And I think that’s really the meat of it. To have somebody who’s sitting next to them who understands all the different pieces around the table. Who can give them the pros, the cons without any bias towards “but if you invest here you get me” or “use my law firm.” So that’s the start of the business. I really love family businesses because they drive the world’s economy. I love that you see innovation, I love the entrepreneurial spirit that you see. The challenge of the family business is often that the spirit and the drive and the vision that created it is in the senior generations, not down the next level. And unlike a corporate environment where I can fire my colleague, or I can choose to go somewhere else, I’m kind of stuck with my family. So I really love the business side with the family side and the ownership side and those are the three circles that form the core of family business, the academic side of family business work.

Ramia: Thank you so much for introducing yourself and you have a very rich background with a lot of experience. You have probably seen a lot of family businesses on the inside and their complexities. We are a complex bunch, I’m not ashamed of it. Amy and I talk about it all the time how every family is crazy and it’s great. But let’s speak very specifically about this whole issue of choosing the right advisor. I think it’s very interesting of you to say your reason for leaving the mainstream finance sector was in order to provide more customized solutions to each family and not having to push a certain product or a certain solution. If you had to give a checklist when a family or an individual looks for an advisor for the family business side of things, what are the primary three points that are things that you should look out for? More of a general level first and then we can drill down into the individual needs.

Holly: I think it’s important to understand where they are coming from and what their skill set looks like. That would be the first. In many advisers, what you find is they are coming out of finance and they are a private banker or a finance person. They sort of break into four groups: you have the people who fled finance who are doing this. You have people who have fled law who are doing this. The bulk of people in the family business space tend to come from psychology backgrounds and consulting backgrounds so you have a lot of psychologists. You also have a lot of family members with the idea being that “I sold my business and I learned a lot in the process and I’m going to help you with your business.” None of those are bad, you just have to understand what it is that you need. Someone who sold their business is going to know what their family business was and what their family issues were. And they tend to see everything through that lens. Someone from a legal perspective is going to see their tool box as being legal documentation and you start to see lawyers doing this wearing a lawyer hat and that could be an issue. On the finance side, certainly the investment firms are offering more family business consultants. I ran the team that did estate and financial planning and you’re starting to see these teams trying to do more family business advising. I think the biggest limitation is they only go so far. So, if you really need somebody who’s going to be on the phone with you at two o’clock in the morning, who’s going to be running the family meetings, those are very limited to find in the financial space. So, understanding their field of origin and if that’s what you need. On the psychology side, the problem or the limitation with a psychologist if they are excellent at the family dynamics and bringing people together but when it comes to actually implementing it, that’s where I found families getting frustrated. We would have a great meeting, we all sing “Kumbaya,” but then when they left, there was nobody to make it stick in terms of the legal and the structural.

The second thing is where they get paid from. If it’s free, it’s not what you want. A lot of the investment firms offer it for free because you’re buying investment stuff. The problem is the free pay structure is not leading to them doing the kind of work that you necessarily want. And this is expensive work, so understanding how they get paid, understanding what the costs look like. And then it’s fit. I will tell clients when we start working that we’re going to form a very tight relationship. We’re going to have very deep levels of trust. And some of them look at me like they’re skeptical. But this is very personal, it’s highly individual.  It’s opening up your family’s dirty laundry and saying you know what, you’re just like everybody else. Your family struggles are not unique and that can be nerve-racking to open yourself up to this type of vulnerability. Often you get to the point where you’re bringing in an advisor because there’s a challenge, a problem, and you need somebody from outside to facilitate it. That means losing control and possibly having to compromise and those are scary things.

Amy: I have a quick question. You talked about using a team of advisors. Would you suggest that one advisor, no matter what their specialty is, serve as the lead to coordinate all the potential helpers?

Holly: I do think it’s important that someone come into quarterback, be it to someone like me or be it one of the advisors. I think the challenge that I’ve seen is sometimes the person that says they’re going to coordinate it may not have a good understanding of what the issues are or all the different players. But yes, it’s important that someone is in there as long as the client commits to bringing in all the players because it is expensive when they work on an hourly basis to bring advisor together to really talk about what the issues are.

Ramia: I found that interesting. I was also going to throw this back to you, Amy in terms of the overlap of what we’re talking about. So, Amy with your very successful coaching business in focusing on daughter’s in the family business, Holly just explained to us essentially three things. Essentially the provenance of the field for the advisor is important. If they get paid and where they get paid from is important and their motives and then generally the psychological fit. When you look at this and someone says I’m looking for a coach specifically, is there a big overlap in terms of what we need to be looking at when we make that choice? Or do you feel it’s slightly different when it comes to coaching?

Amy: Coaching I think is a very discreet intervention. I would never presume as a coach to offer advice of any kind. Second of all, I’m very clear and I think advisors need to be about what the limits are of their expertise. I have worked as a team member with financial people who are advising the same family. It’s remarkable to me though that over time, the financial person knows that family pretty well. I do respect your view of the family dynamics because they often teach me something when I’m working with the whole family. But coaching is pretty discreet, it usually focuses on role, on personal choices that the client wants to make, managing the family, managing the career, and those kinds of issues.

Ramia: Holly, from your perspective now, when we look at the situation of women specifically in the family business. You must have had the experience with all types of family compositions from father to son, mother to daughter, I’m sure you’ve come across it by now. Have you experienced a big difference between advising female-led family businesses and male-led family businesses? Or do you feel it’s pretty much the same? Have you advised and individual family member to actually get a separate advisor? Have you ever come to that moment in time?

Holly: You know, I don’t see that much of a difference between the female-led in the male-led. Because every leader has their own personality and so it’s always hard to say is it the female or the male. Where I see the biggest difference with women in the family business is moving into a leadership position. I think as women, we tend not to do something until we can check every single box. Whereas men are like “How difficult can it be? I am, after all, me, I can do this!” So often women moving into a leadership role, are sitting here thinking “I can’t do this, I don’t know how to do this! I shouldn’t do this! this isn’t for me!” And you’re like, “Of course you can do this, it’s not rocket science! Secondly, there are people to help you. And the third is, the skills that you’re going to bring are going to be different than what your cousin or your uncle or your dad brought to the business.” And making them embrace that is the biggest difference in the emerging leader. Because with the emerging male leader, you’re often needing to rein them in — “Whoa tiger!” And the coaching– there is much more emphasis on the fact that they’re still the young whippersnapper, they haven’t proven themselves. They tend to come in hard. Whereas the women are so insecure, where you’re saying “no, you can actually ask for these things.”

In terms of their own advisor, yes, I have suggested it to people either as a coach on the outside, your own legal team, your own accounting team, whatever you need. And part of that is what are the things that you need to be successful and to feel that you are in control of the situation? And I definitely have done projects where I’m in just a bridge for somebody. I’m moving into this, it’s a coaching position but it’s got a lot of technical and educational aspects to it. Unless I’m doing the kind of coaching that Amy does, in which case, I’m working with a coach who’s thinking and really focusing on the personal presentation and communication issues. But I think that is more like (the family is saying) “I’m getting smart, I’m getting ready, I’m getting helpful.” I have clients where periodically they’ll call me just before they go into a board meeting or a family meeting just to say “this is what I’m dealing with. This is what’s going on, what do you suggest?” And then it’s preparation skills (for the meeting), so that’s sort of it.

I think the biggest time you have to bring your own advisor in is if there’s a conflict. Most attorneys should tell you that there’s a conflict and make you sign a conflict waiver. The basic issue is if an attorney is representing Amy and we’re all in the family business together and we start to work with Amy’s attorney, he might say here’s a conflict waiver, you just have to sign it. But it means that we’re recognizing that he has a duty to Amy. If you come into the mix, then he’s got to duty to you and sometimes it just gets to the point where nobody is supporting or advocating for me. So, having my own advisor so I’ve got somebody who has my back and whose duty is to me. The problem though is two-fold. It can be costly to bring in my own advisor. Often the family business is not going to pay for everybody bringing in their own advisor. They’re going to say we have this team in place, use them. And the second is it can be rather incendiary. You can see situations where there already is some tension and all of a sudden, you’re showing up with your own team of lawyers, it gets people nervous.

So, I think understanding the conflicts is the first part. Understanding that it could blow up on you and how to manage that. The second is really having some clarity why you’re bringing your own advisor. Because otherwise, the cost which is the other C- word here – Conflict, Clarity, and Cost. The clarity is what do I really need this person for? Is this person coming in to get me educated is, is this person coming in for coaching? Is this person coming in to solve a problem? Is this person just to give me perspective? Because bringing in a third party is not going to necessarily make sure that you win. I do see that a lot, people say well I’m losing and so I’m going to bring in my guy and they’re going to sit right next to me and then I’m going to win. And that doesn’t happen because this is all about collaboration and concessions, to bring into more C-words. You have to realize that so much of this is families learning the art of giving and taking. There are a lot of people who go to negotiation sessions, so I could be a good negotiator. At some point, you can be such a good negotiator that you make me mad and I get to a point where I’m just like fine. If I can get you out of my hair, I’ll sign anything. And that’s not a good negotiation because that comes at the expense of your relationship. I think you see that in family situations. You definitely see it in divorces, you see it and buyouts, you see it and a lot of family situations where people are like, I am so done with you. And that has a terrible effect on the ongoing relationship. Any good advisor that you’re bringing in needs to be helping you think the long game, not the short game. Because a lawyer is going to come in to solve today’s problem. An accountant or an investment manager is going to come in to solve their problem or to fill their need. I think that’s where coaches or family business advisors can really come in and help you think the longer-term.

Ramia: So as the acting family business member in this conversation, let’s turn this conversation around on you two.  Similarly, there are situations where you as advisors or as supportive players, you must come to a point where you realize that you’re not having the impact that is desired. I would like to ask you both a question in return. What are the tell-tale signs for an adviser to let it go? Or to actually advise that a family move on to someone else. I don’t know if many advisers are capable of giving up like that. I’m sure there are moments in time where you must realize that you need to fire your client. Have you ever been in that situation, either of you and what have been signs that you recognized okay I’ve stopped having the impact I’m supposed to have, and for everyone’s benefit, we need to move on?

Amy: I can speak from my own experience. First of all, the contract that you set up, and I don’t mean a legal contract, I mean the expectations of what a client can expect of me and my sense of their expectations is so important. I was facilitating a family meeting and one of the members suddenly stopped and said I just want to tell you Amy, I’m furious at you. I was taken aback and it related to a prior meeting where this young man assume that I was playing favorites with other family members. So the issue of trust that the advisor whose working with the family unit, unlike coaching one on one is truly neutral. The value of that confrontation was that I had a chance to reflect on my behavior and what I said and also to explain that actually I wasn’t. But it was important in the evolution of trust between myself and that family. Sometimes getting that kind of feedback is important that it’s all out in the open.  In terms of my own limits, that’s not hard for me at all. I will fire a client when I feel like I’m beyond the range of what I know how to help them with. And that may be that I refer them to a therapist, I may refer to a financial advisor or an attorney. I’m just saying that good old phrase ‘that’s not in my wheelhouse’ is important. But I can tell because I’m not feeling confident, I’m feeling uncertain of how to be helpful. And then there are the tell-tale signs that people just don’t show up for meetings or there is a lot of grumbling. Those are some obvious signs of resistance.

Ramia: What about you Holly?

Holly: I think there are some situations where my job is really to get them to sustainability. So, you fire yourself to say “the work here is done!” and that’s the best situation where you got the problem solved and there’s stability. And as much as I love them, and I would love to be part of the family going forward, it’s not my job.  I think that’s an issue with a lot of advisors in particularly in the family business space. The relationships get so intimate, they forget that they’re not part of the family. I always am cognizant that I work for the family and I think there are times that working for the family can lead you to a point where you will say, okay my work is done. You were brought in to solve a problem, you’ve solved it. Maybe not the way the person who brought you in thought was the right solution. But everybody came to it and then the next problem comes up and it goes against the family member. You need to remind them that they  have to follow this process and the process is the same process that we did in the first place.

In terms of families where I have fired the clients, it’s usually a case where I do it when they’re not listening. They are misinterpreting my role as administrative and not strategic. So, I’ll get phone calls like” set up all these meetings.” There are some families that are just really rude. I remember a whole series of meetings for a family and at the end of two full days running investment RFP, everybody got up and left the room without saying a word to me. And we were all getting on the same trains home and it was just like, “really? Come on!” It was indicative of how they treat people, it was indicative of how they see people, it was indicative of how they saw the work I was doing. I think like Amy said, you will definitely see people grumble. I don’t argue with people about what my wages are. You’re either going to pay them or you’re not. I don’t like losing clients over compensation issues, however if they’re going to not do the work and not move forward and not make decisions, it just doesn’t make sense. I had another situation where we went in and we gave them very clear advice. It wasn’t what they wanted to hear, and it was very clear that all sides wanted something different. Nobody was willing to listen to any other perspective and that’s when I said no. I was doing that with another consultant, thank God because there was another person in the room.

Ramia: There was a witness to the crazy.

Holly: We were asking each other “are we going crazy here?” By nature, I look inward and ask “how can I do this better?” And then you just have to realize that it’s not a fit. I’ve had situations where they don’t return phone calls, they’re not making progress, we’re giving them homework and they’re not doing it. If we do that with the gym and you’re paying a gym membership and you’re not showing up and you’re not doing the work, you get frustrated and you start to resent the gym. I don’t want clients to ever do that, I’d rather cut it off and have them call me when they’re ready.

Amy: I would just add one thing to that and that is sometimes I will find a family where I know there are siblings or a parent-child conflict. When I start to convene them, I become the enemy and their conflicts have seemingly disappeared. I think that’s also a dicey roll for an advisor which is to become the object of all of the conflict. and trying to move that back into a space where real communication can occur. But sometimes it’s very hard to do and very hard to take.

Ramia: I can imagine. Well thank you very much both of you for a very candid insight into the kind of work that you’re doing. And thank you very much, Holly for joining us today and explaining your take. You’ve given us very useful takeaways of how to best use an advisor, what to look out for, what constitutes a fit and why. Very useful advice from your end. we hope to have you on the show again in the future. And wish you a lot of non-crazy families in your future client base.

Holly: I love my clients, I love all of them. is there somewhere I wish I could spend every day with the families because they’re just such amazing people.

Ramia: That’s great, you deserve them, you deserve them. I hope they stay with you for a long time and thank you thank you.

Holly: Thank you so much.


About Amy Katz and Daughters in Charge: Amy Katz Daughters in Charge

Amy Katz is an executive coach and social psychologist whose business, Daughters in Charge, focuses exclusively on supporting women in family businesses.  She is the author of Daughters in Charge: Learning to Lead in Your Family’s Business.