Celebrating the benefits of cross-generational mentoring

Traditional mentoring is typically seen as a one-way street. A young or relatively new entrepreneur benefitting from the guidance and advice of someone far more experienced in their field who in return hopes to “give something back” to the new generation.

However, conventional mentoring is evolving, with cross-generational practices growing in popularity. This new style of mentoring is tearing up the rule book and bridging a prominent gap between those involved in the mentoring process. There is no longer a mentor and a mentee, instead both individuals learn from each other. The experienced entrepreneur passes on the knowledge they’ve accumulated over the years, while the newer entrepreneur helps to improve and evolve their counterpart’s skillset with fresh ideas. 

Championing the concept of cross-generational mentoring is Jo Dalton, long-time Great British Entrepreneur Awards judge and the founder & CEO of leading executive search and people consultancy, JD & Co. Jo is the experienced entrepreneur in a cross-generational mentoring relationship with Antonia Timpany, the founder of Timpany’s, an online marketplace for pre-loved designer bags, clothes and shoes. In this article, Jo dives into the benefits of her mentoring partnership with Antonia, how it works and what she has learnt from the experience.  

What I’ve discovered in recent years is that the mentoring relationship has changed. It is no longer a case of passing on what I’ve learnt during my career as an entrepreneur. Through my experiences working with Antonia and other young entrepreneurs I have found that they are just as willing to challenge me as their mentor which has significantly helped evolve and develop both of our skillsets.

How does it work?

Of course, everyone’s mentoring relationship is different and people work in different ways. Antonia and I have been working together since 2016 and from that point on we have been meeting up regularly, usually once every six weeks or so to go through sales, finance, marketing and PR. We look at what has worked in the past and plan for the future. We’re always available to bounce ideas off each other. In between our one-on-one meetings, we use WhatsApp, we call and we email. It’s very much a constant conversation.

I try to hold up the mirror and challenge Antonia, but in a way that is not too directive. My role in my business requires me to make decisions daily, if not hourly, so I try to give considered and balanced views. I challenge Antonia where needed and try to bring clarity of thought and strategy, but not take over.

What we get from it

I think one of the greatest things about cross-generational mentoring is its ability to give both tangible and mental benefits. As one example, Antonia is committed to vlogging and her passion for it inspired me to take it up. She helped me to grasp the technical elements of creating video content for myself and the business. When someone is so passionate about something like that, it’s a perfect opportunity to learn the small, key details you need to stand out.

I’ve also benefitted from a change in mentality. Working with someone so positive, enthusiastic and motivated, it’s almost impossible not to be infected by that same mindset. Video content is not something I’d ever considered before and isn’t something I was comfortable with at the time. Antonia’s passion inspired me to step outside of my comfort zone, to try something new and explore a new avenue for myself. I’m incredibly grateful to her for that.

I’m also someone who has gained quite a few ‘battle scars’ over the years and they are so often valuable to me in my business, but it is important to see the world through fresh eyes. That’s what Antonia gives me – an insight into new ideas and new skills that can help me and the business. In turn, Antonia would say that while she has a better understanding of these things, she could do with a few more battle scars, so that is where we complement each other perfectly. It provides an excellent diversity of thought.


Thankfully, Antonia and I are lucky enough to have had such a great working relationship. We bounce off each other’s energy and are constantly striving to improve. The challenges of cross-generational mentoring are more internal – for example, dealing with your own personal challenges. For me, it is juggling my time and providing it at the right time. But luckily, this is something I have honed over the years. It can be easy to put your own business first, but when you mentor you have to be prepared to give your time to someone else’s business. It requires patience but the buzz of supporting someone relatively early on in their entrepreneurial journey is hugely satisfying. You can’t buy that feeling. In that respect, the challenge is far outweighed by the benefits that both myself and Antonia get from our relationship.

As a mentor and board advisor to several entrepreneurs, I’m an avid fan of cross-generational mentoring. It is important, however, to seek out a relationship with someone based on the value it can deliver in diversity of thought. It’s vital to have someone from a different background, or at a different stage in their career to you. If you work with someone similar to yourself, the value you gain from it will be severely limited. It’s not always easy, but if you’re open to someone challenging your thinking and changing your outlook, cross-generational mentoring can be transformational for your business and you as a person.

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