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Horizons: Family Office & Investor Magazine

Octavian Graf Pilati: How to use Design Thinking in Succession Planning

Monday, September 19, 2022

Octavian Graf Pilati comes from a family (Khevenhuller) whose history dates back to before the year 1000. He studied mechanical engineering at the TU Vienna. In the years 2015-2018 he managed the crisis in the family business stemming from a failed investment.

Every family has to deal with succession planning in some form or another. No matter if you own very little or if you are incredibly wealthy. By using Design Thinking the succession planning process can be enhanced to reap better results. Design Thinking puts the involved family members at the centre of the process and evolves around their needs. This way succession has the potential to bring the family closer together and to ensure long term stability.

The longer a business or wealth has been in a family and the more generations it has been around for, the more people are usually involved in a succession. Multigenerational businesses often have several hundred family members. And it is to no surprise that in many families the topic of succession is a gunpowder keg, and any member owns a tinder box. It is no wonder, that in many families one or two members may decide at some point to put a match to the keg and see what happens. Even though this is not really in the interest of the family, it happens far too often.

In over 90% of cases, where a family loses wealth, it comes down to the family itself. Of which 25% alone are due to a badly managed succession and 60% due to a breakdown in communication and trust. (Vice Preisser, Preparing Heirs).

What are the reasons when a succession plan fails? What makes a succession successful? What do we need to consider when planning a succession? These are just some questions we will try to explore.

Succession is a people problem

There is so much more to a succession than just the assets that are to be inherited. There are relationships to inherit, there is a legacy to inherit, and there are values to inherit. Not only this, but the next generation needs to find their own way with what they inherit. If they even want to inherit from the previous generation.

From my own experience and from what I see around me, succession more often than not is a painful process for a family. It comes with disputes, hurt feelings, a sense of injustice and broken relationships. Some families manage to recover, and others do not.

Succession is a people problem and not something you can solve with contracts and complicated structures. The people who are the problem are the ones that should be responsible to find a solution. And when I mean “the people who are the problem” I mean everyone involved. We usually believe the others are the problem and that we are the only sensible ones. However, when there is a dispute, it takes more than one person to create one. As it is a human problem, the best way to solve the issue is to use human-centered design.

Succession is a problem that needs to be solved for each family individually and a succession plan is the product, which solves the problem. Each family is different: they have different relationships, number of members, assets and values. All of these make succession a highly complex and unique problem. Every succession will need its own unique succession plan. There is no right and wrong in general terms; there is only whatever is right for a certain family.

Family members have different believes and needs and with these come different roadblocks. Often there are year old emotions from growing up together, which are sealed away somewhere and then erupt during the succession process.

Sometimes there are secrets, which are discovered or exposed during succession. And as you might guess, all these issues have the people involved at its root.

How to approach succession from a human- centered perspective

We as a family – my family - failed in our last succession, which led to me pondering upon the topic and looking into our last three successions. I found that the same mistakes have been repeated over and over again and I could not stop thinking on how this could have been avoided.

The topic of succession can lead to much pain and suffering in a family and can be a topic for therapists to work through with members for years. Many families pay lawyers and tax advisors a lot of money to create tax and inheritance law efficient succession plans, to later find out that family members don’t agree. Patriarchs often believe they know how succession should be, but never speak to the next generation. The next generation often believes they know what succession will be like, but never speak to the generation in charge about it. No surprise then, that family members end up depressed when these expectations are not met.

Anyway, as an engineer I love to solve problems and create products. This is where human-centered design and essentially design thinking come in. Human-centered design means that when we try to solve a problem and create a solution, the solution should evolve around humans. Humans have needs and would like these needs to be met. So, any solution needs to be centered on humans and their needs we want to meet. As succession is a people problem, the humans should be at the center of the solution. Design Thinking (DT) is nothing more than a human-centered approach which was created to explain how designers and engineers think when trying to solve a problem and design a solution.

Design thinking in a nutshell

There are several DT processes out there, and I personally like to use the Stanford DT process as a guideline and for laymen I like to use the 4D Diagram by the British Design Council.

DT is an iterative process using divergent and convergent thinking. In simple terms: if you want to reduce options to find the right one, you first need to create as many options as possible. This is often where people take a wrong turn in problem solving. We try from day one onward to find the perfect solution and we spend way too little time creating many solutions without judging them.

Also, the iterative part of problem solving is often misunderstood. Only in rare cases will you be able to seamlessly follow through the process without backtracking your steps here and there. It is not unusual to have to start again once you have reached halfway through and you realise some of your assumptions and hypothesis turn out to be incorrect. It is disastrous to continue with a false hypothesis.

Looking at the DT process as an example: it can be the case that when you are in the ideation phase you realise that you defined the problem badly, so you need to go back to the define phase and see what went wrong. Then you realise that you lack some information and back you go to the empathy phase. It doesn’t mean your work was for nothing. Maybe you just lack some bits and pieces, or you were completely off course.

Before we dive into the five phases of the Stanford DT process it is important, that we understand families, family businesses and successions better.

Four circle model of family businesses

In general terms a wealthy family or business family consist of subcomponents and is part of a larger system. By looking at the “three” circle model (I added a 4th out of experience) we can see that each person can be part of several different systems or part of all of them. Any individual which is embedded in the family can be part of the other three systems or not.

Often family businesses have external shareholders, such as managers or employees. Families often have trusts for philanthropic efforts or other community projects and often are deeply embedded in the local communities of where their family or business is situated. Not every family member can or wants to be operationally involved, some won’t even want to own shares.

What makes a succession great?

What is a succession? Essentially it is a transition from one generation to the next. In this transition many different things are moved. Not only wealth, but also values, purpose, legacy, relationships, people (for example employees) etc. Not every generation will put the same value to each of these “assets”, which can light the gunpowder keg.

We see a lot of issues and problems in succession, which poses the question: What actually makes a good succession? After sitting for a while and pondering upon it, I decided to ask my network and I have gotten a host of different answers from family members and advisors. I have to admit I posed the question not so clearly, which actually ended up being good. Some people focused on the process and some on the outcomes. While some themes were recurring, there were others which came up only once. And there was not a single point, which I would see as bad advice. Below I will list an excerpt of some of the answer I got:

  • Open and honest communication.
  • Honest assessment of skill and interest, preparation, recognition, and management of egos.
  • Shared values and a common understanding of the family purpose.
  • Ensuring that standards are maintained during and after the succession process.
  • I would like to add empathy. We need to listen everyone.
  • I’d say that purpose is near the top of the list. Individuals with purpose—and families with a shared purpose—seem to thrive through adversity and challenge. Purpose is a wonderful gift, but cultivating it is hard.
  • Start early!
  • The estate of one of my best friends has the truly great tradition of getting out of the way once you are retiring ...meaning the older generation is moving not only to the dowager house but to a completely different town not too far away to be able to meet regularly - but somewhere where they can’t see what’s going on at the estate on a regular basis ... that enables a clean break and a smooth transition I think because each generation has to re-invent the estate for their times.
  • What makes a succession great is if everyone is satisfied in the end. Not necessarily getting everything they want, because that isn’t always possible, but at least satisfied and the family unit intact. How that happens, when that happens and with whom is completely subjective to the individual family. Each one is different with its own nuance. But if I can walk away after the succession, and everyone is still hugging each other (or at least still talking to each other) then I feel it was a great succession.

Reading through the opinions above, we can see that not everyone has the same definition of a great succession. If you ask me, all the mentioned above are parts of a great succession. If all the above is met, then the succession was truly great.

My favourite there is that if everyone in the family is satisfied and the family is still intact, then the succession was successful. This goes really well with the Harvard’s negotiation project. A succession is nothing more than a negotiation between generations, between people essentially. And you should always aim for a solution which does not only satisfy your interests, but also leaves the relationship intact. Even better if the relationship improves though a succession, which a succession has the power to do.

One aspect which is incredibly important is also the timing. When should you start with a succession? On the day your children are born! That is when you need to start planning: What do they need to learn? How do I empower them? How can they build their own identity within the family and business? What are our family purpose and values? The criteria that make a succession great boils down to the family and what their unique situation and needs are. If the family is not intact prior to a succession, we can use a succession to try and repair relationships. That would make it great in this specific scenario.

Typical Roadblocks in Succession

Succession comes with a few roadblocks, which make the process hard and often painful. Before we dive deep, I would like to thank Dominik von Eynern for his research and support on this topic.

There are many different roadblocks in a succession and again they are individual for each family depending on their circumstances. Grouping them in general terms you have financial, operational environmental and behavioural roadblocks. Financial and operational roadblocks tend to be much simpler to solve as they usually need technical solutions. Environmental roadblocks involve things like the environment the family is in, societal changes, market changes etc. Behavioural roadblocks are however the most common problem to find in succession and in my opinion the most difficult to get around. Therefore, we will focus more on those in this article.


The first big issue is timing, which overarches all groups in a sense. We need to realize that timing is never perfect. When is the best time to start with making a succession plan? When should you act out the succession?

With this we stand in front of a big change that has occurred in the last 100 years and raises the complexity of succession: people live longer. These days it is not unusual that in a succession we need to take three living generations into account. And as we continue to grow our knowledge about the human body, we will soon enter territories where we have four living generations in a family.

Therefore, in my opinion succession is now a continuous process. Every time a new family member is born you will have to adapt your succession plan. People tend to have several careers these days. It is not unusual that an heir starts out with one career, which has nothing to do with the family business. And at a later point in time decides to get involved in the family business. Rigid and static structures may inhibit this.

Governance, rules and regulations

Each family has their own governance structure, some lack one completely. The governance structure may be helpful in succession or may not. Again this depends on the family and the structure.

In general, however, we can say that a static and rigid structure causes problems. We tend to forget that a family is a collective group of individuals and that the group members did not choose to be part of the family. You may say that spouses did, while in reality spouses chose a certain individual before the family (unless we talk about “gold diggers”). The next generation may not agree with certain rules or values. The values and rules may be outdated and not workable in the present time.

The better the family members are aligned in terms of purpose and values, the smoother the succession. Keep in mind though, that the likelihood of getting 100% of the family aligned is quite slim, especially the larger the family grows. This is something families often have a hard time to deal with as we sometimes just need to accept that a family member is different. Diversity is a strength not a weakness.

The patriarch and matriarch

Often it is the patriarch or matriarch who are a roadblock. The reasons can be multiple. Some have narcissistic tendencies, some may face an identity crisis, while some lack the trust in their children.

In the typical patriarchal family system, the patriarchs decides what happens and how things are done. Especially if it is the first generation, their strong willingness was probably a part of why they were so successful. When it is time for succession this can lead to them trying to impose a plan on the family. After all this is how they always did it. Succession is then often the point where the next generation finally stands their ground. Often their agreement to the plan is required, and this gives them a certain position of power against the patriarch. Then things get emotional and a dispute occurs.

The issue of trust can be for similar reasons. The patriarch and matriarch spent most their time working on the business and left the parenting to employees. The first seven years of our lives are very formative, especially concerning our parents. If our parents are not present in our childhood, we do not form a bond of trust with them. This is vice versa. Our parents then later become business partners for us. While a strong trust bond can be extremely valuable in business, due to the typical upbringing it is not present. On top of that, if the parents are strong willed people, the children tend to become people pleaser. They have to follow rules imposed on them. When the children are older, the parents – the generation in charge - are surprised by the outcome and feel that their children are not competent and strong enough to lead the business in the future.

It is also common to have patriarchs enter an identity crisis when succession planning starts. They are the business and the business is them. Letting go the reigns can mean they lose their identity. This needs careful consideration, they need something to look forward to after letting go. If you do not take this into account, you might make a succession plan that then never gets acted out till the patriarchs dies. After a certain age we start to lose our decision making capabilities, the world changes faster than we can keep up with. This is why many family business enter a crisis: the people making the decisions are past their prime time. Their experience is invaluable and should be a resource to the next generation standing in front of the steering wheel.

Childhood Trauma

While the patriarchs themselves are often a roadblock, the next generation is not innocent either. Often the next gen is battling with childhood trauma. Here we are not in general talking about extreme events such as physical abuse. Simply certain behaviours the parents showed them in growing up will lead to trauma. Toxic behaviours are adopted in childhood and carried on. We do not develop our own true self, if we are not in the right environment for it. We tend to copy others and who is closer to us than our parental figures. Now, if you parents are not present enough you will not only have your parents as parental figures but also the people who took care of you; many different people with varying values and behaviours. I can tell you from my experience this is really confusing.

Childhood trauma can lead to a host of problems. The problems can even become physical with health issues like chronic fatigues and MCAS. The traumas can result in a lack of boundaries and a lack of accepting boundaries. You are confused inside with who you are. Resentment and hate for the world and your family usually sets in. Some people drown their problems in addictions, from alcohol, to drugs, to sport. When a family has a strong legacy it can inhibit the next gens development, as a legacy comes with expectations. These expectations can carry a heavy weight, especially if our inner self wants to do something different.


Many families lack the communication skill that are required. The reasons for this often lie in childhood. If we never learn to communicate properly, we have a problem. If we never learn to listen to others or be empathetic, we cannot understand other people’s actions and intentions. If we do not learn to communicate our boundaries, they are constantly overstepped. If people do not communicate their boundaries, then we constantly overstep theirs. Without communication we have expectations of others, without them knowing. NO wonder then we are disappointed constantly. If we do not communicate our perspectives and how we see things, others will not understand how we see the world. This goes on and on.

With open and honest communication, we can mitigate most problems. If we are open to the world in general, it is easier to accept differentiating points of view. Accepting doesn’t mean we have to agree, it means we understand.

I had great communication problems with my parents. Their behaviour triggers me in many ways and the roots lie in childhood. Behaviour of certain members can trigger emotions such as anger, angst, sadness etc. When the family behaviour is generally dysfunctional, then members are not equipped to deal with these emotions. These emotions then inhibit communication. If you feel angry, the other person senses the anger and will be invested with anger themselves. I used to start shouting or walking out of meetings with my parents. These days I can deal with my emotions and keep calm. Any conversation will need a calm person to spread the calmness. If you have no one in the family, you will need an outside party to facilitate conversation.

A final word to roadblocks: we need to keep in mind that most of the family members are oblivious to these issues. They often neither recognise them in others and especially not in themselves. Do not expect to find open ears at your first attempt to address roadblocks. Denial is a defensive mechanism our brains like to use to protect us from harmful events. Just by denying something is not true or existent the pain of realising is kept away. At least consciously it is, the unconscious damage will still be present.

Applying Design Thinking on succession

The Stanford Design Thinking process, which we now apply on succession - consists of five phases: empathise, define, ideate, prototype and test. While the empathise and ideate phase are divergent stages, the define, prototype and test phase are convergent. Divergent means we try to increase the number of options and convergent we decrease the number of options.

Empathise Phase

As the title suggests, in the empathise stage we are empathetic. To start off we first need to understand what empathy is. The term is thrown around a lot without really being understood. Empathy is “the ability to understand and share the feelings of another” – Oxford Dictionary. Especially in the topic of succession, which involves lots of emotions from family members, getting empathetic is important. If you need to read a book on how to become more empathetic I can recommend you “Humble Inquiry: The Gentle Art of Asking Instead of Telling” by Edgar Schein.

When you are empathetic, you do not have to agree with the feelings of the other, that would be sympathetic. We do not aim for that. Family members will have all kinds of feelings and there will be feelings that you do not agree with, or other family members agree with. Understanding where these feelings come from and understanding the logic or trauma behind them is of great importance in this phase. As we have gone through already, childhood trauma plays a huge role in family dynamics.

In the empathy phase we want to find out the agendas and interests of everyone involved - family members, management (as we know the management of the company may not consist of family members), other stakeholders like creditors etc. As usual each family and family business has its own unique situation and constitution, so there is no standardized list for this.

Now there is one thing to be incredibly wary about and this is that people’s intent and their actions often do not align, the same applies for their interests and positions. People may say they want something, but in reality, they want something different. From own experience this happens a lot in families. Members are afraid of communicating their needs, believes, wishes and they hide behind a certain position they take. For example, the sibling wants the wealth to be split 50/50 with his other sibling, no matter if it makes financial sense. In reality though, the sibling feels unfairly treated by the parents and wants to leverage the succession to finally get treated fairly. As a rule of thumb I recommend to use the five-Whys- method ( from Sakichi Toyoda, where you ask Why? at least five times to get to the bottom of the issue.

We want to gather as much information and data that we need for the succession as possible. This does not only include emotional issues from the family. You should look into competencies the family members have, you should look into what makes financially sense, you should look into where the economy might go etc.

Below you can see the human-centered design pyramid, which will give you a good guideline for understand people. It is important to ask Why?, How?, When?, What? and Who? in order to solve a human problem. A little tip from Simon Sinek is, that humans have a hard time to answer Why?, so try to package any Why-question behind a How? or What?. This will get answers that you would not get in a Why?. The human mind is not made to think in Why?. This is a lot to investigate, so do not worry if you do not find everything. DT is an iterative process, so you can come back to this phase and add things any time you find them.

Regarding the typical succession roadblocks, you should be able to identify all the roadblocks in the empathy phase. The first step to mitigate any problem and to improve is to actually be aware of the problem. Most family members will not be aware of the issues, especially the ones regarding themselves. Sometimes making people aware of issues can already be the solution to it. However, I would not bet on it being the case. Just the exercise of trying to understand each other and the whole family situation, will bring everyone onto the same page. In neurological terms it should help with getting the family better synchronised.

Define Phase

In the define phase we try to define the problem. This might seem a little silly, because our problem is the succession, so what needs defining. This is not such a simple matter as it seems. In the define phase you want to concise the issues down to specification points that you can then solve. From the empathy phase you will have found a bunch of feelings, characteristics, facts and interpretations, which will need sorting. It is very difficult to solve all the wishes all the members have. Essentially succession is a negotiation and there might be some win-win solutions. However sometimes we will need to settle for compromises. The aim is to have the family intact afterwards and decide on a course of action to transfer the family’s wealth.

The first thing you want to try and do is to write a problem statement. This is a simple sentence that describes the issue at hand. “Transferring the family’s wealth, while leaving the family intact.” seems like a good start, but try to get a little bit more specific. As mentioned multiple times, each family is different. Then you want to sort through all the information you gathered and see what the sub-problems are you want to solve. Each family member will have wishes, interests, needs and hopes they would like satisfied. Try to list them all. Then you will try to identify the vital points - the musts haves, and the nice to haves; the wishes.

What I then like to do is to weight the points accordingly using a scale of 1 to 5 or 1 to 3. It is unlikely that you will be able to design a solution that will satisfy all “must haves”, so you want to weigh them. Wishes I tend to weight with one point as they are a “bonus”. Later we will use the specification to judge ideas and concepts. Remember though, judging is not done till the prototype phase. Also don’t get tempted to judge people’s interests. If something is of great importance to a family member, then it is important to them. Be careful in the weighing here and take into account what you found out. You are not to judge the importance of family member needs; each will have communicated this to you clearly in the empathise phase.

The family coming together to define the succession issue and to decide on the roadblocks that need to be addressed – ideally with the help of a designer/ mediator - is a crucial part for alignment. Agreeing on the goals that are to be set should help the family members move in the same direction. In an ideal scenario the family can together overwork their family purpose and the values they live by. Or if those are non-existent, they should end up defining them for the first time.

Ideate Phase

Now - in the ideate phase - we actually get into creating ideas for the succession. I recommend using an open innovation approach, which means that we include the family members in the process of generating ideas.

In this phase it is crucial that we do not judge any ideas. Not ever. The aim is to create many ideas, and the ideas do not have to have “substance”. Ideas usually do not have substance, and when they do, they are a prototype already. Sadly, our society and often family culture insists on immediately judging everything, especially members who seem to have no experience or knowledge. Often the best ideas however come from these people, as they are not constrained within their box of thinking.

Thus, I recommend for all the ideation session that you have a “referee” whose sole purpose is to mediate and to make sure the rules are kept. Any attempt of judgement no matter from whom is shut down immediately by the referee. This should not be a family member as they should be involved. If the family does not want to involve an outsider, family members can take turns. I do still recommend using an outsider, as the aim behind this is not to have a social experiment. If you want to see if for example the patriarch shuts up when his nephew who at the moment is the referee tells him to, feel free to try.

The most common ideation method is brainstorming. There are many more methods out there, which in my opinion yield better results. There are whole books and articles on ideation methods and before you get into the ideation phase you should either read these or have a designer who can help you through these processes. Getting the methods right makes a massive difference. My favourites are brainwriting, the seven thinking hats, wild ideas question, the morphological box, nature inspiration and SCAMPER. Here you find a good resource on ideation techniques: https://www.interaction-design. org/literature/article/introduction-to-the-essential-ideation-techniques-which-are-the-heart-of-design-thinking

In the ideation phase you can also invite lawyers, tax advisors and anyone you feel will bring value and their own ideas to the table. Outside perspectives are of great value. However, the same rules apply experts as to anyone. No judging, just ideas!

A lack of trust in the family is a very common problem, especially if the family business was the most present focus of the parents. Thus, creating ideas together can improve the psychological safety of the family. Finally, everyone gets to have ideas and not be immediately judged. Judgement coming later and by using methods such as the “Wild Ideas Question” can take away the fear of failure. This gives creative family members who might be portrayed as black sheep the chance to show their skills. People pleasers have a change to put forward ideas without trying to please anybody, with no judgment there is no pleasing as such. Strong characters learn to listen and to speak when it is their turn. As a final reminder I want to stress again, that these positive effects will only arise when ideation is done right. It is important to get the loud, judgemental, and narcissistic family members under control, or to build work groups which “protect” the integrity of the process.

Prototype Phase

To start of the prototype phase, we need to select the ideas that are worthy to become a prototype. We already prepared a framework for this using our specification from the define phase. You just go through your ideas and give them points for each specification point. Keep it simple, which means an idea either meets a point or not. You can then apply the weighing of these and go ahead with the top three. If you wish you can also add a “wild card” idea into it, which is the family’s favourite.

People’s feelings may change throughout the process and due to working together on this as a group the family might have moved closer. You could say they have become better synchronized (as my college Domink v. Eynern would say).

The prototype phase is where you get together with subject matter experts to develop concrete plans. This can be legal contracts, new company structures, working out philanthropic endeavours etc. Maybe a company evaluation if one of your succession options is to sell the business and disperse the wealth. Maybe a restructuring plan to make space for the next gen in the family business. The prototypes are as diverse as there are ideas. In simple terms, you try to make your ideas into a more concrete plan, that could be executed.

With the prototype the family gets to see, what they - with help - managed to create. For some families this may be the first time the family worked on something together and have an actual outcome. Seeing this can create trust levels.

Test Phase

In the test phase you usually test a product by trying to actively break it. In software you will have test versions like an Alpha and Beta Version that first customers can test. Physical products have to go through a myriad of tests where their application, features and their physical properties are tested to the extreme. The same applies for a succession plan. Test what you can. Try to find ways to test out the prototypes and parts of it, without making any irreversible steps.

If you decided your youngest daughter should become CEO, then let her give it a shot, while the current management is not too old to take over again. Or you add an extra CEO where she works alongside the current manager. Same applies to the idea of getting an external manager. Get one and try it before it is too late to reverse. Let children sit on the board of a company and experience what being a shareholder is like. Give them the possibility to make decisions. Some plans you can try to test through role play. Have family members play through scenarios - their new positions of management or ownership - and see what happens. Is it likely to work or is it a total disaster?

As a small piece of advice: remember that a plan is only good till the first point of contact. Your succession plan should be an iterative plan, just as the process is iterative. Things will change, you will discover things you have not seen at the start. At a conference, where I was part of panel on family office structures and succession, I remember a great point of a fellow panellists. He said that you cannot plan love, you can make all the best succession plans and then your son falls in love with an American woman and relocates to the US and all your plans are down the drain. As the family created the plan together, the family learns to fail or succeed together, rather than through individual efforts.

Succession planning starts the day your children are born! Do not wait till it is too late. In my opinion successors are not born. But it is for the family to educate the next gen properly, while giving them enough space to form their own identities and try out what they would like to do and who they would like to be. Following a structured process by creating a succession plan together gives the family a chance to improve their communication. The plan is ideally revisited regularly and steadily carried out.

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