Family Business Audiocast | Episode 24 | Wendy Diamond | Deloitte

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About Our Guest:

Wendy Diamond is the Chicago Office Tax Managing Partner and serves as the U.S. Family Enterprise leader for Deloitte Private, providing specialized assistance to multi-generational businesses in navigating the complexities associated with family-owned enterprises. With 25 years of experience, Wendy’s expertise lies in strategically advising private companies and their owners. Her knowledge spans various areas, including income tax and succession planning for privately-owned businesses and single-family offices. She provides guidance on diverse topics such as family office structuring, process and technology transformation, transfer pricing, and trust and estate planning. She assists clients in identifying and addressing critical issues and opportunities, including evaluating capital needs, preparing for leadership transitions, and developing philanthropic and community relations strategies.

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[Transcript]

R. Adam Smith: [Intro] Welcome to the Family Business Audiocast on LinkedIn. I am R. Adam Smith, creator of this audiocast series. As an entrepreneur, investor, founder, investment banker, and board leader the last 25 years, I am fortunate for my many experiences within the family firm industry.

A warm thank you to our live audience on LinkedIn today – and for those listening in the future.

A brief comment on why I created this broadcast: private companies are a passion of mine, having grown up in a family of entrepreneurs, and having engaged for two decades in deals, strategic transformations, investments, and boards, with an array of fascinating family enterprises, family firms, and family offices. I founded this series to offer a useful platform for listeners to hear from veterans, academics, and leaders in the vast family firm ecosystem. Whether you are a family business owner, building, running, or advising a family office, or just expanding your family office activities, I hope these conversations are useful and enlightening. And now, it is time to turn our attention [01:00] to our accomplished guest on today’s episode.

Today, I am pleased to host Wendy Diamond. Wendy, it's great to have you today from Chicago.

Wendy Diamond: Thank you so much. I'm happy to be here.

R. Adam Smith: Fantastic. Appreciate it. So, a few words on Wendy. Wendy serves as the Chicago Office Tax Managing Partner, and she also heads up the US Family Enterprise platform at Deloitte, where she leads a dynamic team of tax professionals dedicated to understanding and meeting client needs. And, for over 25 years, she was also the head of multiple divisions at Deloitte, previously Arthur Andersen. She advises multi-generational businesses on navigating the complexities of family ownership. And, this expertise spans a very wide range of areas in the family firm and family enterprise practice, including tax, succession planning, family office structuring.

All of these equip her with the insights to address a wide range of challenges [02:00] from capital needs assessment to succession planning to leadership transitions. No shortage of things to do for your clients, right Wendy?

Wendy Diamond: Absolutely. Always evolving. Always interesting.

R. Adam Smith: Wonderful. Let’s get started with a couple questions, and then we’ll talk a little bit about Deloitte, get back into some other questions, maybe have some time at the end for some questions from the audience.

First of all, you manage the Family Enterprise platform for one of the largest accounting practices in the world, if not the largest, depending on what survey and what year you're talking about. So, just share with us a bit about how you got there and what it's like for you working there.

Wendy Diamond: Sure. As you noted, I'm a tax partner by background, but one of the great things about Deloitte is the opportunity to continue to expand and learn more about the services that we as a firm across all of the functions can bring to family enterprises. And, growing up, I started [03:00] working on family offices as an intern. And then, as I transitioned, I did more work with family-owned businesses before they had a liquidity event, and then I was able to transition my knowledge from working on family offices to help clients through those liquidity events and now setting up family offices as well.

So, I love this group of clients. They're always dynamic. There's always something interesting happening with them, whether it is what they're doing with their business or what they're doing in the community.

R. Adam Smith: Absolutely. You know, I cover hundreds of family offices, and most of them are doing deals or making investments or buying companies but there's a much larger business out there with family enterprises or business of families. Maybe just for everybody, a bit on your point of view on the scale of the family enterprise community in the world, and how do you see it growing?

Wendy Diamond: You know, obviously it's a topic that's hard to [04:00] nail down the number of family enterprises that exist in this world because, you know, there's always a new one being formed. I think what's interesting about family enterprises is, while many, you know, survive for decades, generations, even if there is a liquidity event, there's something about the background of a matriarch or a patriarch or their child or grandchild; there's a level of entrepreneurism, I guess I would say, that they're always creating a new business. And so, while we may, you know, in certain periods of time, see liquidity events happening, I think that as those liquidity events happen, there is new innovation happening as well, and it's just in the blood of many of these families to create the next business, which I think has been really impactful. As you probably note as well, Adam, that even when there is a liquidity event, many of these families are choosing to do direct private equity [05:00] investing and basically creating the next empire.

So, I think it is something, just part of their history, their backbone, that creates more and more family enterprises.

R. Adam Smith: Absolutely. There is a lot of complexity. I continue to be surprised when we see the latest surveys from you guys at Deloitte or the new RSM report, the JP Morgan report, the Campden report, the UBS report. Comments from some of our colleagues on this platform have been also quite useful in the space as well.

We've had guests, that you know, from Peter Vogel to Alfredo de Massis, Angela Robles, Richard Wolkowitz, Christina Wing, Martin Roll, of course your contemporary Karen Costa over at RSM. So, there's been a lot of information shared. I agree with you that nobody really knows the exact number, but they're absolutely exploding in different ways. I also would love to hear your thoughts on the multi-family office structure and some of the ways that Deloitte serves the multi-family office structure as well.

[06:00] Let's talk about some of the challenges these enterprises face. Maybe share, how do you advise them in the complexities of the development of the family enterprise? Let's say some challenges when they want to grow, they want to acquire, and then of course when they want to prepare for sale.

Wendy Diamond: Yeah, I would say from growth and acquisition, there's a couple of areas that I would say these family enterprises are focused on, whether it is organic growth and really looking at digital transformation. What are they doing? What are they reinvesting back into the business to transform and really meet the needs and anticipate the needs of their clients? And so, that is always a discussion, as you know, with family-owned businesses, how much are they going to invest back into the business versus distributing, making distributions to shareholders? [07:00] And, that could have a significant impact on what could be distributed to the existing shareholders, but with a long-term view on the needs of the future family members as well.

So, I would say from a growth perspective, it's really been helping family-owned businesses think about transformation, whether it's technology that they use in the business, maybe it's technology that they use from behind the scenes on the business, how they transform their finance department, things like that.

And then, the other area I would say is really thinking about optimal talent strategies as well for growth. A lot of times growth comes from being able to acquire talent in the marketplace. And, when you think about incentive planning for acquiring that unique talent, we've worked with family-owned businesses to think about short-term and long-term incentive plans to attract and retain that talent that can help the companies grow. [08:00] That is something that we continue to see in high demand across these family enterprises because in many cases, as you also know, the companies may not, the owners may not transfer a part of the business itself, ownership in the business itself, but they still want to share the benefits of growth in the business with their management and employees, and this is one way to do so.

R. Adam Smith: Exactly. Some of the research I've read and the experts I've spoken with, including Professor Mat [Matthew] Hughes was on our show. He's a lead editor at FamilyBusiness.org and EIX. And then, we had a similar conversation around the challenges of entrepreneurship, human capital. Going back with Ron [Ronald] Diamond and of course Linda Mack and some other experts in the space, Korn Ferry, etc., they are trying to address the human capital disparity between the demands of the larger family enterprises or family office [09:00] and the availability of that talent.

Maybe just a little bit more on the human capital side. Maybe talk about the value of the board of directors or board charter, and then maybe talk about the importance of a CEO, the talent of the CEO, being an internal CEO or an external CEO.

Wendy Diamond: Yeah, I mean, I guess let's start with the value of the board of directors. There's a couple things I think we should highlight there, one being as family-owned businesses look to formalize their boards, really looking for outside board members, whether they're in an advisory capacity or truly become independent board members, it really brings a level of increased specialization. And so, for example, identifying board members with specialized experience with transitions, whether it is, you know, somebody has passed or somebody is going to retire that's [10:00] in the family that has run the business, really helping to think through how can they make that as seamless of a transition.

The other part of that, when you think about the board, is really looking at the profile of the family and thinking about what diversity of thought, what diversity of experiences, and just diversity of backgrounds do the board members need to have to align with the next generation of leaders, because the next generation of leaders really may look different; there may be more daughters in the family, whereas it may have been brothers that had started a business.

And so, looking at certain demographics of the board could really be a critical part of having the next generation of the family align, and leverage the board and the way that they should to help take them to the next level.

R. Adam Smith: Sometimes, however, what I am [11:00] hearing and seeing is that the board charter, the original board charter—which relates back to the G1 and the legacy and the mission and the values of the G1—need to be modified and really evolve and modernize as you go through G2, G3, as you think about spending the internal wealth externally and to buy companies or even selling.

What do you and Wolfe Tone and your team advise in terms of, how aggressively is it necessary to evolve on the governance perspective when you think about helping these companies survive and grow?

Wendy Diamond: I think there are new challenges, outside forces, that are really impacting family enterprises and almost forcing them to really look at the experiences of the board members. So, what I mean by that is whether it's the rise in cyber-attacks and do they have somebody with cyber experience on their board, whether it's thinking about sustainability [12:00] and how will that impact their business, how customers see them, and so having a board member with that experience. Or even a board member with certain alliances. How the family enterprise grows its business may look differently because maybe they are going to elevate alliances as it means for new growth.

So, I think that those experiences are really what is causing family-owned businesses to look at their boards and say, I can't just have the matriarch or patriarchs, advisors, family, friends on the board. I really need to look to other advisors if the family enterprise is going to take it to the next level with the next generation.

R. Adam Smith: It's never an exact answer, right? But you've been helping families manage this intersection of their professional lives, let's say their mission of creating wealth or maintaining legacy or creating scale. Maybe can you share a bit about the [13:00] intersection of those professional commercial demands and their personal ones? And maybe just some advice to family advisors we have on this audiocast about stepping into this hybrid, this delicate balance between personal and professional.

Wendy Diamond: I would say that for family members who, at some point, will elevate and take on a greater leadership role within the company while they still are managing the dynamics potentially of certain family members who are not as involved, really taking on a stewardship mentality is critical.

And so, when we think about that, you know, the leader is a steward of this asset, this business, and thinking about how they can protect, improve, and grow it until it's passed on to the next generation; that is the top priority. It is not necessarily something that is going to stay with this person, it's about, how do you develop the next generation of leaders and create a blueprint for [14:00] generations to come?

I think the other important attribute to have, and this is for any leader, is intellectual curiosity, really taking the time to understand why things are being done, and before you assume something is wrong, thinking, really understanding, what's going on and why has it been done that way? And, in the instance of the individual who's now a leader in the business but still having to respond to the family as well, it's asking the right questions to understand what is impacting certain areas of the business and really understanding what opportunities might present themselves to the company by asking those questions.

It may be, how is the company going to use AI? Or how will the talent workforce look different in the future? How do we need to train them differently? How could growth change if we grow, [15:00] you know, across the US or globally? And so, really asking all of those questions and even at a younger age starting to think about what worked well with that person's transition and what would they do differently for the success to the next generation as well.

R. Adam Smith: Yeah, I like that point of view. We had a conversation with a G2, which is really a G3 manager of a large $3 billion privately-owned company you would know because your family is from Chicago and St. Louis. We had Kyle Chapman on the audiocast recently, and his father, Bob Chapman, was the inheriting owner for Barry-Wehmiller. And, in the conversation with Kyle, it was very interesting that being a younger president having massive responsibility, he found it quite useful to really run with the [16:00] existing mission and culture, but then modernize it with the board, with human capital, with branding, and also to take some of the internal liquidity for, in this case, a profitable family business, and then recycle it into ancillary businesses and create almost a private equity arm internally, which is quite interesting.

And that's, I think, very innovative and somewhat unusual, but I think that that decision to recycle some of the capital into diversifying activities will become quite vogue in the current market. What do you think about that?

Wendy Diamond: Yeah, I mean, this is always the debate of how much of the liquidity stays within the existing operating business. And, for example, where there is a family office, we commonly see there's a debate between the head of the family office or CFO of the family office and the operating business CFO and the desire to pull cash out of the operating business [17:00] so that family members can diversify their wealth.

And in many cases, we've seen that the families describe the existing operating business as their direct private equity, and they may want to get into other asset classes to think about, you know, how could they have a broader asset investment pool. And so, what we commonly see is then that gives family members choice. They may set up separate investment partnerships with different asset profiles, whether it's a liquid portfolio, you know, maybe a rental real estate portfolio, etc., but it also gives family members the choice whether or not they want to co-invest, going forward, all of the assets.

And I think we've seen positives of giving family members the choice as opposed to just having one family member—again, a matriarch, patriarch, or next-generation leader—make the decision for everyone.

R. Adam Smith: I agree with that. I want to turn over to your recent report. [18:00] It is useful for everybody to have a look at this family enterprise survey that recently came out by Deloitte, written by Wendy and her colleague, Wolfe Tone. It is a really wonderful 23-page report that is surveying hundreds of responses of current-gen and next-generation of leadership within their client base and talking about a range of really fascinating matters.

Maybe just talk a little bit about that survey and what is in there. And then, also talk a bit about some of your favorite findings, please.

Wendy Diamond: There are obviously many, many surveys out there, but what we really wanted to focus on, as you noted, was the differences in perceptions between the current generation, the generation running the business today, and next generation. And so, we surveyed within Deloitte Private, we surveyed over 500 family members. And a couple very interesting things to highlight.

First had to do with how confident are the different, the [19:00] current-gen versus next-gen, with succession planning. 24% of the current generation strongly agreed that their existing succession plan would allow the business to continue running smoothly without disruptions if an important family employee moved on, retired, or passed away. However, only 13% of the next generation felt the same way. So, there's definitely some uncertainty on how they feel.

And I think that is really important to note because what we found is, when you think about succession planning, oftentimes they are less likely, the current generation, to be open and transparent about the succession plan. And, we know from conversations with numerous family-owned businesses and their owners, it's difficult to have that conversation due to personal or emotional decisions, but it truly can have a [20:00] favorable impact on the transition of the family enterprise to the next generation if they have that open conversation.

And so, we've worked with those family enterprises and asked those tough questions. How much has the current generation of leadership shared with the next generation about the company's growth plan, liquidity considerations, or internal and external risks that impact the business? Who is going to lead the business going forward? Will it be a family member or will it be a non-family member? And what skills are necessary to take the family business forward to keep it a family business? And also, what is ownership going to look like, which in many cases, families may not want to share that.

R. Adam Smith: Transparency is a heated topic in these companies, in a sense, because there's no exact, perfect way to express that transparency, right? Especially when you're preparing for a merger, an acquisition, or consolidating the company, selling the [21:00] company. There's a lot of personal and emotional tension there. So, what do you all suggest in terms of where should that transparency lie? Does the buck stop with the CEO or is it with the founder or at the board member? And then, how does that transparency lead into decision-making?

Wendy Diamond: You know, it takes courage to be willing to have a transparent conversation. And I've seen some really successful family-owned businesses where they have leaders, either on the management team or on the board, who are courageous enough to be transparent, open, honest with the family and have that conversation about what could happen if they were to pass, for example, without doing the succession planning.

And, you know, that requires a level of trust going both directions whether or not, you know, the owners of the business trust [22:00] that group of advisors, whether it's management or the board, and whether, reciprocally, the board and management feel as if they have been given the responsibility and authority to share that honest feedback back with them.

But why I think that's important, just as an example, is if that succession planning has not been done and that conversation has not risen to the level of the board agenda, then the challenge will be, if somebody passes unexpectedly without the planning, it could be detrimental to the business if there's a significant liability in the owners of state as a result of this very illiquid asset. And when the company thinks about continuing on as a family-owned business, what does it mean to the liquidity of the business if they either have to redeem a shareholder, borrow money, take on additional liabilities for the business to pay [23:00] for that liability?

It could impact the growth of the business as well as future distributions out to shareholders. So, taking it back to why is transparency important? It's really benefiting future generations if you're willing to have that open dialogue, be transparent about what's going to happen, and then have the dialogue about what can be done to prepare for that.

R. Adam Smith: Absolutely. There's another leader in your firm, Dr. Rebecca Gooch, that I spoke with initially, and there's a post and report that she talks about, as your head of insight, that there is a need and a greater reliance on outsourcing. You talked about human capital. Also, we've talked about board of directors, the independent director role is super important, and just having expert vendors be around the family enterprise and the family office.

Maybe just talk a little bit more about the outsourcing role. Of course, Deloitte is quite massive, but just at the basic level, like, what are the key three areas of outsourcing you think [24:00] adds the most incremental value that is supplemental to the internal resources of the family office?

Wendy Diamond: Family office or family enterprise?

R. Adam Smith: Let's do both. Let's talk about a family enterprise that just is a large, let's say, half-a-billion-dollar family company, no family office, and then maybe talk about the family office itself as an entity.

Wendy Diamond: I mean, from a family enterprise perspective, I think the real question is, when you think about the type of skills or talent that may exist in the community where the family enterprise primarily sits, when you think about that and you think about, “Do I have the talent pool that I need,” whether it is to do cyber, for example, whether it is to handle certain financial reporting, things like that. Do they have the skillset in their community? And if not, they may look to outsourcing alternatives.

In the family office setting, we see it come up in a number of ways. And again, [25:00] it goes back to talent shortages in some capacities because many high-net-worth families are looking for the same type of talent with similar skills. I will say, we commonly see—just because of the complexity of the structures that families often put in place to meet their needs—they often choose to outsource tax. The tax laws, you know, require incremental disclosure, the reporting is complex, the underlying investments are complex, and so, often we see tax being outsourced.

I would say, we're seeing an increase around what we refer to as controllership. So, even just the whole finance—partnership reporting, outsourced accounting—I should say, being outsourced as well, [that] volume of data. And we have the technology that can handle doing that reporting in a timely manner, as opposed to hiring talent to do that, buying or acquiring the technology to do it. Many families choose to outsource.

R. Adam Smith: [26:00] True. I just want to share for the listeners a couple of minutes on Deloitte. It's a super fascinating organization, actually a British firm founded originally in 1845. There was an actual Deloitte; William Welch Deloitte, was in London, and he then came over to New York, apparently in 1880, with a suitcase and probably one client, and now it's about $65 billion with a few employees—about 415,000 employees.

Despite the scale and being the largest accounting firm in the world for most of the recent years. Still today, Wendy? That's the largest accounting firm in the world, I think so, by revenues and or employees. 

Wendy Diamond: Yeah.

R. Adam Smith: But it's great to see the culture and the governance. And, the footprint of the firm results in continuous compliments by Bloomberg Business, being a top place to launch a career. Also, Gardner Group noted that it's the number one consulting service firm globally [27:00] for several of the last years. Of course, it's one of the Big Four. You actually started at Arthur Andersen, and I think if I read correctly, back in 2002, a decent amount of the Arthur Andersen business was merged into Deloitte, and then you began your career at Deloitte around that time.

Wendy Diamond: Yeah, I had actually been at Arthur Andersen for four years, and we all know what happened. And, in 2002, many employees from Arthur Andersen came over to Deloitte, and we've had successful careers. And we were welcomed with open arms.

R. Adam Smith: That’s right, No, it's fantastic. One last topic. There is a very robust capability at Deloitte around technology, emerging tech, business resilience, cybersecurity. Maybe just talk a bit about, we've seen these polls of concern in the LinkedIn community and different surveys about the family enterprise and the family offices being much more prepared for business resilience and especially cybersecurity, so maybe share a couple of [28:00] comments on what's going on and how do you help clients navigate their overall ecosystem for technology?

Wendy Diamond: Sure. Yeah, cybersecurity continues to be in the top three priorities of the board agenda. We did a survey earlier this year of 100 private company leaders, and we asked them about, where would you allocate productivity gains in the next 12 months? And 27% of them said they would allocate additional resources created by those productivity gains to improve cybersecurity.

So, cyber security continues to be top of the agenda, but it can't just be a “I'm going to check the box, I've done it,” and put it in a drawer. It is constant, an ongoing effort that needs to be maintained. And really, the key is, it's knowing that likely, you know, some cyber event will happen when we have different local family office forums or national family office forums. You know, we know this is a topic that [29:00] everyone wants to talk about. And it's really about how prepared are you to respond, whether you are a family office or a family-owned business because at the end of the day, it's about protecting what we refer to as the Crown Jewels, those assets, whether it's personal information, information within the business, so that the organization can maintain its operations, protect its brand, and maintain the trust either from customers or the family members in the case of a family office.

And so, we have worked with a number of family-owned businesses, family offices, to do both penetration testing to assess how ready is the company if an attack was to happen, as well as creating a roadmap. And we know in this environment, not everything can be done at once. And so, I think the important thing is working with these organizations to have a phased approach that may be 18, 24, 36 months and helping them prioritize what will help them mitigate risks [30:00] in a timely fashion so that you can maintain the trust of the client base.

And so, I think the key has been—whether it's cyber roadmap or any kind of technology transformation roadmap—being able to show organizations a path forward, but also recognizing that it has to be done in some paced manner, is really critical. Because we know at the end of the day, the companies still have their everyday business to do, their day jobs, and this is just an added responsibility that we can help support them with.

R. Adam Smith: That’s wonderful. Very, very important area, and important to be judicious but also have patience. That's a tough balance, right?

Wendy Diamond: Absolutely.

R. Adam Smith: So, we'll open it up for a question or two from the current audience. If you'd like to pop up on stage, just go down to your bottom right or put your hand up and we'll pull you up on stage for a question.

I have two on LinkedIn. I'll just ask one of them. [31:00] So, right now there is a massive amount of wealth generation after the boom years going through the family office community, right? That's creating significant wealth. Going to G2, going to G3, that creates massive tax matters and considerations, and of course, as we talked about, where to deploy that liquidity. What is the number one area where the incremental profits will be going the next 10 years out of successful family offices and their liquidity?

Wendy Diamond: I mean, I think if you look back at the Global Family Office survey we just did, Deloitte just released, it was over 350 family offices around the globe that there's still significant wealth that they responded that would be invested in private equity. And so, I think that we'll continue to see that trend happen. And, you know, with the patient capital as well that we always speak about, whether it's direct private equity or third-party funds, [32:00] that is where we anticipate the liquidity will go.

R. Adam Smith: I agree. I think that a lot of that allocation has come away from hedge funds and away from cash management into operating assets and also real estate, of course.

We do have one question here. Jasmine can come up on stage and ask her question now.

Wendy Diamond: Sure.

Jasmin Ren: Hi, Wendy. Absolute pleasure to meet you. I love listening to all the amazing insight you have. And as a woman in leadership, especially in the family office space, that's really inspiring to me. My question is actually curious to that specific statistic that you brought up, that you said that around, you said like 14% or so of these next-generation family members don't feel as prepared to take on the role and take on the strategies that are being integrated. So, I was curious, because I'm Gen Z, because I look to have a future somewhat in the family business space, I was wondering, how can we best adjust that and give them ways to feel more prepared, given the sort of behaviors, [33:00] strategic thinking, and just like development that we've had as a Gen Z kind of student and age group?

Wendy Diamond: Thank you for the question, first of all. I would say in many situations, you know, we also saw that, from the survey, that so many more family members are having outside business experiences before they come into a family enterprise. And so, I think those outside experiences are actually going to be very impactful because these individuals, Gen Z, bring a different perspective back to the family enterprise.

But for those who don't necessarily want to come back to work at the family enterprise and maybe they chose a path that was unrelated to the family business, I think it is still about helping give them financial literacy, helping them understand, you know, the industry, the priorities of the business, maybe not as much the metrics, but how to [34:00] ask the right questions to help the family make decisions if they have the opportunity, for example, to be on the board of a family-owned business. I think it's teaching them how to ask questions and how to think about new information they're getting. That's how they can continue to grow, evolve, and give back to the family enterprise.

R. Adam Smith: That's great. Thank you, Wendy. I'm glad we had that question actually.

Okay. Well, we'll wrap up today. I want to thank you, our family business audiocast attendees today, and our esteemed guest, Wendy Diamond. Wendy, thank you so much for today.

Wendy Diamond: Great. Thanks for having me.

R. Adam Smith: It was a pleasure. You're an aspiring leader and we look forward to seeing more great things from you and Deloitte.

This is R. Adam Smith signing off. Stay tuned for the next episode of the Family Business Audiocast on LinkedIn.

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