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Alexandra Hollingshead lawyer photo

Ali advises the trustees of complex trusts on trust law, structuring and tax efficiency. She also advises families and individuals on wealth structuring and succession planning, often focusing on the specific legal and general needs of family businesses. Her approach to complex, multi-party tax and structuring issues is collaborative and empathetic, and she is also a qualified mediator.

Ali has an in-depth understanding of both the wide-ranging legal needs and commercial drivers of substantial landed estates and has advised the trustees of one of the highest-value estates in the UK for many years. Her practice ranges from complex trust and tax advice to the interplay of trust and divorce law.

She advises individuals, families and family offices on estate planning and succession strategies. Her focus is often on tax and succession advice, which first and foremost requires a listening ear. Ali supports her clients to put in place tailored, practical succession plans that mitigate the risk of family dispute and balance clients’ desires both to protect wealth for the long term and allow the freedom for younger generations to succeed on their own terms.

Ali advises on both UK and non-UK structures. She is adept at working with foreign lawyers to build practical and streamlined strategies.

Ali’s interest in the human stories inherent in her specialist legal field motivated her to qualify as a mediator. She deploys her mediation skills day to day for the benefit of her clients in managing multi-party files and advising with professional empathy.

Ali qualified as a solicitor in 2008.


Memberships & Accolades

  • Ali was named as one of the Top 35 private client lawyers under 35 in 2014.
  • Ali qualified as a mediator at Regent's College (March 2016) and is a Civil Mediation Council member.
  • Ali achieved a distinction in a counselling course at Birkbeck University (2013/14).

Ali co-hosts the highly-regarded Farrer & Co Next Generation conference each year, an event the firm runs with C Hoares, Dixon Wilson and Stonehage Fleming at the Grove Hotel. She enjoys giving the 'next generation' the opportunity to consider their attitudes to wealth, communication and their own family dynamics.



Alexandra is recognised as a key lawyer for Personal Tax, Trusts and Probate in the Legal 500 2022 Guide. 

"Alexandra Hollingshead stands out for being very hands-on and user friendly." (Legal 500 2022)

“Hard working… helpful and well targeted advice” – longstanding client and CEO of a large UK family office, June 2018

"Perceptive and engaged" – leading commercial mediator Ali worked with in August 2017

"Your suggestions and assessments were continually spot on" – leading mediator Ali worked with in December 2017

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