Succession planning across generations

Becca Timmins
Becca Timmins

This is the second in a series of three posts, where I consider the challenges of intergenerational conversations and how we can facilitate them more effectively for better outcomes. You can find links to the other two posts at the end.


For financial advisory firms, few conversations are more fraught with generational landmines than those surrounding succession planning. With the founder’s life’s work and legacy at stake, emotions can run high, and clashing expectations can quickly derail discussions.

Not all founders want to sell to consolidators at the end of their career. Many would much prefer to pass their legacy and their clients on to a trusted next generation.

In this situation, one of the issues I often see is the desire to keep everyone happy, resulting in no-one saying what they really mean. It’s all very well meaning, but can have some pretty disastrous consequences!

Where to begin?

The first step is to create an environment of openness by understanding the disparate generational perspectives in play. 

The leadership styles and beliefs of the 70s, 80s and 90s were very different to current leadership teaching. For example:

An older principal may define success primarily through professional achievements and the continuation of their firm, whereas younger successor candidates could place higher priorities on work-life balance, autonomy, emotional intelligence, or making a broader social impact.

Perhaps the principal is waiting for the successor to step up, take control and show strong leadership to demonstrate their readiness for them to take a step back. Meanwhile the successor is worrying about treading on ties and experiences the principal’s guidance as micro management.

Rather than hearing these perspectives, we often make assumptions about the other’s intentions and miss the opportunity to learn from each other and reach common ground. 

Exploring them with mutual curiosity and respect can be a game changer. What deep-rooted assumptions about ambition, status, or life purpose may be colouring how each generation sees the path forward? Unearthing and sharing these is critical for reaching common ground.

Shifting dynamics

Even with healthy dialogue, succession is a complex and lengthy process that will come with ups and downs. That’s actually completely normal and if there aren’t tensions sometimes you’re probably not talking about the important stuff!

I often see younger people recruited and nurtured with an eye on the succession plan. While the original hierarchy remains unchanged, things go swimmingly and everyone is really happy. However, as skills and experience develop, and those younger people move into more senior positions it can become harder. The status quo is challenged and so the dynamics shift. Most businesses find that hard to navigate.

Anyone who has navigated parenting a teenager into adulthood will be familiar with similar challenges! 

The same suggestion applies though. Listen, keeping a really open dialogue. 

When you hear feedback that you don’t particularly like – that’s probably because you know there’s truth in it (my 14 year old pointing out how stubborn me and his older brother can be the other week being a case in point!).

It’s complex

Navigating succession is complex. Many think that because they’ve got great existing relationships it’s going to be simple and they can manage it without conflict.


Most of us have baggage that we are blissfully unaware of, hang ups about all sorts of things, and often major change can make us feel unsafe. 

Recognising that it’s going to be hard, expanding your skillsets and support network could be a huge help.

Progress will be gradual and plans will continually evolve. Younger and older parties need to make peace with this iterative reality, and manage any attachment to rigid outcomes. I’ve seen that learning to listen better, and holding conversations in a Thinking Environment, with rules about not interrupting and taking distinct turns can really help. 

Honour the past and re-imagine the future

As you navigate the journey, honour the stories and legacies that came before, while remaining open to boldly re-envisioning the future in alignment with evolving values and priorities as well as the ever changing external factors (tech, regulation and the rest). 

If you can find ways to nurture trust, and be vulnerable across generations, that will help. 

Make space for all voices and viewpoints, while finding the shared interests. With deliberate facilitation and commitment from all sides, even the most daunting generational divides can be bridged for a successful transition. 


If you’re navigating a succession in your business, learning more about the Thinking Environment and how it supports trust and healthy debate in meetings is a great place to start. Take a look at the Transforming Meetings programme here, or get in touch for a chat to see how I could help you navigate the complexities. It’s an area that I have personal experience in, within a family business and am always very happy to share from my own experience.

This is the second in a series of three posts on the topic of intergenerational conversations. Links to the others are below.

Building trust in intergenerational financial planning

When assumptions stop helping

Photo by Vitolda Klein on Unsplash

Becca Timmins

Becca is an accredited Time to Think Consultant, Coach and Facilitator. She has extensive experience coaching and developing people within a Thinking Environment framework, working with individuals and teams at all levels, primarily within financial planning businesses.
Social share CTA

Becca Timmins

Becca is an accredited Time to Think Consultant, Coach and Facilitator. She has extensive experience coaching and developing people within a Thinking Environment framework, working with individuals and teams at all levels, primarily within financial planning businesses.
Social share CTA

Keep in touch

If you would like to be added to our mailing list and receive our blog and details of future courses and offers just leave your details below.

Subscription Form

Similar Reading

A taste of transformation

A taste of transformation

It's difficult to put into words the profound experience of truly thinking for yourself, uninterrupted.  Experiencing it first hand though, is something entirely different - it leaves people buzzing with excitement about incorporating this pioneering approach into...


Submit a Comment

Your email address will not be published. Required fields are marked *