From teenagers to trustees managing the multigenerational digital divide

From teenagers to trustees – managing the multigenerational digital divide

This article is written by Tim Ramsey and Juliet Young, Partners at Schillings.

Today, an online search is the starting point for how the world sees you. Whether it’s a news article on Google or an Instagram post, these digital breadcrumbs can paint a surprisingly detailed picture of a family’s lifestyle, values, and vulnerabilities. 

For high-profile multigenerational families, this digital footprint isn't just a matter of curiosity. It can have real-world impacts. It can influence whether families are free to pursue personal, business, and philanthropic interests discreetly, or if they are exposed to headlines, hostile attention, or investment disruption. And, in an age of AI, what you put online impacts what is summarised about you – not always accurately.

Generational differences

Managing this online presence is complex, especially across multiple generations. While some family members may be deeply cautious, others — often younger — may see the online space as a platform for expressing their identity, engaging in activism, or pursuing entrepreneurship. A teenager might post regularly about a cause they are passionate about, while an older sibling who is taking a leadership role in the family business may prefer to avoid digital exposure altogether.

These differing attitudes can lead to conflict. A genuine effort by one generation to manage the family’s digital reputation can be perceived by another as censorship or control. Without careful handling, such differences widen gaps in understanding and trust, complicating not just online privacy decisions, but broader family dynamics. 

There are also differences in understanding of technology. We often hear Gen Z being blamed for “over-sharing” on social media, but in our experience older generations’ lack of understanding around privacy settings mean that they inadvertently share more than they should. For one client who asked us to check what was available online about his children, it turned out to be a proud grandparent who was the source of the potentially damaging posts. 

A three-step approach to managing the divide

Finding common ground can be difficult. We’re often asked to help families navigate these generational divides and develop shared, sustainable approaches to online privacy. To do this, we use a three-step framework that has successfully helped many families build consensus around core principles while allowing for individual expression. Focusing on making privacy real, shared and personal creates a practical and respectful model for digital privacy in multigenerational families.

Make it real

People are naturally optimistic — we tend to think that bad things happen to other people, not to ourselves. That optimism bias can make it challenging to generate a sense of urgency around online privacy, especially when past experiences haven’t delivered any obvious negative consequences.

To overcome this, it’s useful to begin by simulating what a hostile actor — a journalist, cybercriminal, or campaigner — might find through open-source research. By meticulously combing through this public content, risks can be identified. In one case, we uncovered Strava running routes that pinpointed the home address of a family member. In another, we almost cracked a password based on a pet’s name revealed on social media. These findings are powerful catalysts, bringing the issue to life – and showing just how quickly a stray comment or photo can become a privacy vulnerability or reputational firestorm.

Make it shared

Once awareness is raised, the next challenge is achieving consensus. It’s not enough for a few family members to be cautious — everyone must understand the risks and commit to a shared solution. Families need safe, structured spaces to think about privacy together. For this reason, facilitating in-person workshops is hugely beneficial. 

These workshops should include structured exercises, simulations, and informal moments — like shared dinners — that help ease tensions and build empathy. The goal is to co-create a “family privacy charter”: a shared framework that outlines values, principles, and boundaries.

It’s not uncommon to discover that family members have more in common than they realise. Differences often reflect style and emphasis, not fundamental values.

Make it personal

Even with shared principles, individuals need space to interpret and apply them in a way that aligns with their own values and goals. Here, one-to-one coaching, incorporating behavioural science, can be hugely beneficial. This coaching should explore family members’ personal ambitions and how online privacy can support — not hinder — them. 

We’ve seen these workshops open conversations and instigate change across generations. For example, a teenager who once felt their identity was overshadowed by family legacy came to see that a controversial online profile might harm their credibility when launching a non-profit. Realising this on their own terms led them to adjust their online presence — not because they were told to, but because it helped them get closer to what they really wanted.

Making the issue real, the solution shared, and its application personal has helped many families navigate the digital world with more unity, confidence, and security.

In doing so, they achieve something priceless: peace of mind in a world where privacy is increasingly rare, but even more valuable.

Case Study: Multigenerational Privacy Strategy for a Public Family

A high-profile family facing increased scrutiny because of political office engaged Schillings to assess and manage their digital footprint. The goal: to protect the privacy and reputation of the client and their children.

Make it real: A rapid online investigation simulated what a hostile actor could uncover in a day. The findings — from reputationally damaging playlists on Spotify, passwords on data breaches and location data from Snapchat - made the threat tangible and urgent. 

Make it shared: We sought through introductory conversations with each family member to understand the family’s core values – what they could all agree on was the desired outcome as the principal stepped further into the limelight. 

Make it personal: One-to-one coaching sessions created space for each family member to receive feedback on their existing online footprint and think through how what they wanted to communicate online aligned with their wider ambitions. These feedback and coaching sessions were held privately so that there was no judgement from other family members. 

One family member in their early twenties was so concerned about intrusion; all their social media accounts were deactivated. Another created some guidelines on what they’d post – allowing them to build their career, without unnecessary media attention. Throughout the sessions we provided practical guidance on how to manage their privacy settings or think creatively about sharing content while not divulging personal information. 

The result - the principal took the next step in their political career, and the kids were able to continue their careers and studies without disruption. 

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