Harry Sheehan

Harry has a busy practice which covers Personal Injury, Employment, and Tax. He is ranked as a leading Junior within The Legal 500 2025 Personal Injury Guide, and a Rising Star with The Legal 500 2025 Employment Guide.

Harry has been instructed as junior counsel in a number of large and complex cases. He was instructed in the Supreme Court proceedings in Professional Game Match Officials Limited v HMRC [2024] UKSC 29 as junior Counsel to Jonathan Peacock KC and appeared in the Supreme Court as junior counsel to Robert Weir KC in the case of Cape Intermediate Holdings Ltd v Dring [2019] UKSC 38. He regularly acts as sole counsel in both the civil courts and employment tribunals.

Prior to commencing Pupillage, Harry read Philosophy at Cambridge and obtained a masters from UCL where he studied the nature of promises.

• Recommendations

  “Harry is very responsive and helpful. He is also very thorough and provides detailed advices.” - Personal Injury, Legal 500 2025

  “Harry is a trusted advisor. He’s highly intelligent and technically sound.  The best thing is that he gives an honest and impartial view of a case – and provides a clear strategy, together with practical and client-focused solutions” - Stephen Hall, Lawyer, BT Legal.

  “From a Solicitor’s perspective, Harry is a great barrister to work alongside. Harry is flexible in his approach and takes on board the level of support and advice requested by the client and/or Instructing Solicitor.” - Bronya Greatrex, Solicitor, Hempsons

  “Harry strikes an incredibly important balance between robust and persistent when necessary whilst being respectful, charismatic and unprovocative and understands how to subtly tweak this balance to suit the preferences of the Judge he is before and based on the progress of the hearing” - Bronya Greatrex, Solicitor, Hempsons.

• Employment

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  Harry is ranked as a Rising Star within The Legal 500 2025 Employment Guide.

  Harry has a broad practice covering all areas of employment law and acts for both claimants and respondents. He appears regularly in the Employment Tribunal and is commonly instructed in cases with complex factual backgrounds and cases that are of particular reputational importance to his clients. Harry has also been instructed on a number of occasions in the Employment Appeal Tribunal and is comfortable with appellate litigation raising novel issues of law.

  Harry has a particular expertise in employment status. He was instructed as junior counsel in the appeal to the Supreme Court in Professional Game Match Officials Limited v HMRC [2024] UKSC 29 , the leading authority on employment status. He was also previously instructed as junior Counsel in Kickabout Productions Limited v HMRC [2022] EWCA Civ 502[HS2] , an IR35 case in the Court of Appeal concerning employment status and the construction of contracts of employment.

  Harry's recent instructions in the Employment Appeal Tribunal include: 

  Parnell v Royal Mail Group Ltd [2024] EAT 130 – The Claimant had presented 13 successive claims in the Employment Tribunal, which were consolidated into two separate proceedings. The claim for reasonable adjustments was upheld in the first proceedings, but dismissed in the second proceedings. The Claimant appealed on the basis that the two judgments were inconsistent, and that the second tribunal had misapplied each of the respective legal tests. Harry acted pro-bono for the Claimant.

  British Telecommunications plc v Robertson (UKEAT/0229/20/RN) - Harry acted for the successful Respondent, appealing against the decision of the Employment Tribunal that the employee had been both unfairly dismissed and subjected to s.15 discrimination arising from disability. HHJ Auerbach J accepted that the Tribunal had failed to properly apply the test for causation under for the purposes of s.15 after reaching an unexpected finding in relation to disability. He also found that the Tribunal had erred in relation to the claim for failure to make reasonable adjustments, and dismissed that aspect of the claim without remitting it to the Tribunal.  

  San Diego v Bagshot Rehab Centre Ltd and anor – The Claimant raised concerns about onboarding procedures at a care home for patients with substantial clinical needs and was dismissed after being employed for 1 month. The ET found that expressions of concern were not a disclosure of information. The Claimant appealed on the basis that the Tribunal failed properly to apply the test for a ‘qualifying disclosure’. Harry acted pro-bono for the Claimant.

  Johnson vs Latchman (UKEAT/0239/19/OO) - Harry acted for the successful Claimant, responding to an appeal against a decision to extend the time for a Claimant to bring a claim for disability discrimination. Tucker J found that the ET's findings were open to it, and that, in any event, she would have made the same decision. 

  Godwin Jumbo v Zonal Retail Data Systems  (UKEAT/0275/19/LA) - Harry acted for Respondent and successfully defended an appeal against a decision not to allow the Claimant to amend his claim to add four new causes of action where the Claimant had argued the ET had misapplied both the tests for extension of time and the balance of hardship test for applications to amend. 

  Le Page v East London NHS Foundation Trust (UKEAT0161/19/OO) - Harry represented the Respondent who successfully applied for costs following withdrawal of the Claimant's appeal. Eady J accepted the Respondent's submissions and awarded costs having found that the appeal was both unreasonable and misconceived. 

   

  Harry has recently been instructed in the following matters in the Employment Tribunal: 

  • Ashraf v NHS England  – Harry acted for the successful Respondent in a 10 day trial for race and religious discrimination and part time worker detriment. The Claimant had made 38 allegations relating to events that took place over 5 years. Harry successfully defended the claim in its entirety.
  • Hall v BT plc – Harry acted for the successful Respondent in a 6-day trial for unfair dismissal, sex discrimination and sex discrimination. The Claimant was the sole-carer for his disabled daughter, and argued that the Respondent’s decision to restructure the business without permitting him to work from home was discriminatory. The Claimant sought to apply s.19 of the Equality Act 2010, relying on his daughter’s disability, by analogy with the comparable European case of CHEZ. The case involved a novel attempt to interpret s.19 in accordance with the Marleasing principle. Harry successfully defended the claim in its entirety.
  • Warburton v Openreach Ltd – Harry acted for the successful Respondent in a 10-day trial for trade union detriment, disability discrimination and victimisation. The Claimant alleged that he had been subjected to detrimental treatment during a redeployment process because of his status as a senior trade union and health and safety representative. He also alleged that he had been treated detrimentally because of his dyslexia. Harry successfully defended the claim in its entirety.
  • Harry is instructed in relation to ongoing  remedy proceedings in a disability discrimination claim. The ET has found that the Respondent is liable for discrimination, and the Claimant seeks £740,000 for lifelong loss of earnings on the basis that the discrimination caused severe psychiatric injuries.  
  • Singh vs M&S plc - Harry acted for the Respondent in a seven-day hearing, dealing with numerous allegations of discrimination arising from the Claimant's disability which alleged to culminate with forcing the Claimant to resign. Harry successfully defended the Claim in its entirety
  • Black vs FCO Services - A ten day trial for constructive unfair dismissal and disability discrimination in which Harry acted for the Respondent (led by Christopher Stone KC) and successfully restricted the scope of the Claimant's claim to the month prior to dismissal although the claim related to events took place several years beforehand. 
  • Smith v The University of Brighton Academies Trust – Harry acted for the Claimant in a 5-day whistleblowing claim. The Claimant was an Assistant Principal who complained that pupil safeguarding procedures were not being properly followed prior to being made redundant.
  • A highly contentious whistleblowing case (acting for the Respondent) in which anonymisation orders have been made and the disclosures are said to have been made in bad faith which was listed for an 8 day hearing prior to settlement. Harry was successful in defending the anonymisation order despite challenge by the Claimant. 
  • Sterling v Genesis Research Trust and Professor Lord Winston  - Harry acted for the successful Respondents opposing an application for interim relief on the basis that the redundancy exercise leading to the Claimant’s dismissal was likely genuine. 
  • Robertson v British Telecommunications plc - Harry acted for the Respondent in the two-day remedy hearing, dealing with issues of pensions loss and loss of earnings over a period of two years following dismissal, and was successful in obtaining judgment in the sum contended for by the Respondent.

   

  Harry’s recent advisory instructions include:

  A matter in which an employee working for a UK company lived and worked in the middle east and was responsible for developing the company’s interests overseas. Harry was instructed in connection with a dispute about the employee’s entitlement to a calculation of a bonus payment and was specifically asked to advise on jurisdiction, appropriate forum and territorial scope.

  A matter in which a senior employee was diagnosed with Parkinsons shortly before receiving notice of termination allegedly due to redundancy. Harry was instructed to advise as to whether the employer could be prevented from dismissing the employee by virtue of his contractual entitlement to permanent health ensurance. Harry was led by Andrew Burns KC.

  A case in which the same employee had brought two successive claims against the same employee. Harry was asked to advise as to the procedural consequences of the overlap between the two claims and to provide his strategic input on preparation of the latter claim for trial. Harry was also instructed on both claims and successfully defended both in full.

• Personal Injury

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  Harry is ranked as a leading Junior within The Legal 500 2025 Personal Injury Guide.

  Harry has experience in a wide range of multi-track personal injury matters. The majority of his instructions are in cases where the claimant has suffered a permanent or life-altering injury. He also has experience in attending inquests in matters where fatal accident claims are in prospect. Harry predominantly represents Claimants but also accepts instructions to act on behalf of Defendants.

  Harry was instructed as junior to Robert Weir KC appeared in the Supreme Court (as junior counsel) in the matter of Cape Intermediate Holdings Ltd v Dring [2019] UKSC 38 Harry acted for the successful Respondent.

  Harry's recent instructions include:

  • A case in which the Claimant fell from a scaffolding and suffered a very severe brain injury. he has suffered a catastrophic injury and is now confined to his bed for the majority of the time. He is likely to: have permanent care requirements, never return to employment, and experience incomplete neurocognitive recovery.
  • A case in which the Claimant suffered a severe leg injury when using a sandblaster to clean machinery in a powerplant. The Claimant was employed by a Polish company, subcontracted to a German company, and was injured whilst working in England. Permission has been granted to serve proceedings out of the jurisdiction on multiple defendants.
  • A case in which the Claimant suffered a spinal injury and became paraplegic as a result of delayed diagnosis to his spinal condition. The Claimant died 3 years later as a consequence of his paraplegia. Harry is instructed in connection with an ongoing inquest into the Claimant’s death on behalf of the bereaved family.
  • A case in which the Claimant was struck by a car whilst using a zebra crossing. He sustained a fracture to his right shoulder and developed persistent, chronic shoulder pain that has continued despite numerous surgical interventions. The claim was initially pleaded at around £500,000. 
  • A case in which the Claimant was shot during a hunting accident. The bullet passed through his arm and into his chest, severing or severely damaging the ulnar and median nerves and leaving the Claimant with very limited use of his arm. His arm is unlikely ever to be a useful tool again.
  • A case in which a wrist injury at work led the claimant to develop complex regional pain syndrome, the symptoms of which will be permanent. The case involved substantial disputed medical evidence with varying diagnoses in the fields of psychiatry and pain management.
  • A case in which the claimant suffered severe and disabling injuries to his wrist in a road traffic accident. The claim is pleaded in excess of £300,000.
  • A two day inquest into the death of a person resulting from a pulmonary embolism whose prescription for anticoagulation medication ended after a review appointment was cancelled due to the Covid 19 pandemic. Harry was instructed on behalf of the bereaved family.
  • A case in which the claimant’s foot was  crushed  in an accident work. Due to the  claimant’s pre-existing  diabetic neuropathy, this resulted in her developing charcot  arthropathy and suffering permanent disabling symptoms.
  • A case in which the claimant HGV driver was struck by a falling oak barrel which fell from the back of another driver’s vehicle and landed on his ankle, causing a crushing injury to the end of the fibula, and a break to the outer fibula. Primary liability was admitted but contributory negligence was alleged. The case settled for £110,000.
  • An accident abroad in which a claim was pursued under the Package Travel, Package Holidays and Package Tours Regulations 1992. The Claimants became trapped in a burning hotel in Spain and were exposed to smoke for a prolonged period of time which exacerbated pre-existing medical conditions.

• Tax

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  Harry has a broad practice in tax. He has experience in both contentious and non-contentious matters, and acts on behalf of both taxpayers and the revenue. He has experience in Capital Gains Tax, Inheritance Tax, Stamp Duty Land Tax, and overseas issues such as the Transfer of Assets Abroad Regime. 

  Harry is currently instructed on behalf of the Taxpayer in the Supreme Court proceedings in Professional Game Match Officials Limited v HMRC [2024] UKSC 29 (led by Jonathan Peacock KC).

  Harry was instructed on behalf of the taxpayer in both the Court of Appeal and Upper Tribunal hearings in HMRC v Kickabout Productions Limited [2022] EWCA Civ 502, which concerned the correct application of the Ready Mixed Concrete test in IR35 cases (led by Jonathan Peacock KC in the Court of Appeal and by Georgia Hicks in the Upper Tribunal). 

  Harry was instructed on behalf of the revenue in the Upper Tribunal hearing in Daarasp and anor v HMRC which concerned the application of the Ramsay principles to determine whether expenditure was 'incurred on' the acquisition of software rights as well as the construction of a closure notice for the purpose of determining the jurisdiction of the First-tier Tribunal (led by Aparna Nathan KC).

   

  Harry’s recent advisory work includes:

  Advising in the context of a settlement agreement that sought to indemnify an employer against historic liabilities to income tax and NICs on sums paid to its founder and director.

  • Advising on the SDLT consequences of the purchase of a property which included a number of separate buildings and an annex to the main building, giving rise to issues as to whether the property was non-residential and the extent to which it would qualify for multiple dwellings relief.
  • Providing advice concerning the repayment of an interest free loan by an offshore trust, giving rise to issues under the Transfer of Assets Regime and the repayment of a debt, and the meaning of a "debt on a security" under the TCGA 1992.
  • Advising (as junior to Marika Lemos) on the unwinding of a structure involving multiple offshore trusts, sub-trusts and companies, giving rise to numerous issues including the application of part 7A of ITEPA, the Transfer of Assets Regime, Capital Gains Tax and SDLT.

   

  Harry has recently been instructed in a number of tax cases in the First-Tier Tribunal on behalf of the revenue including:

  • An alleged tax avoidance scheme which sought to dispose of trust property in the UK and acquire similar trust property offshore to avoid a charge to inheritance tax of around 2.4 million pounds (led by Marika Lemos).
  • An alleged tax avoidance scheme which sought to avoid capital gains tax by relocating a trust through different offshore jurisdictions shortly before and after disposing of valuable assets (led by Christopher Stone KC).
  • An alleged tax avoidance scheme which sought to artificially engineer capital losses to reduce a charge to capital gains tax of around seven hundred thousand pounds (led by Marika Lemos).
  • An alleged tax avoidance scheme intended to circumvent capital gains tax in which the issues involve the identification of a "qualifying option" under s.143 TCGA 1992 and application of the Penalties Regime under both the Finance Act 2007 and the Taxes Management Act 1970 (led by Marika Lemos). 

   

• Clinical Negligence

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  Harry accepts instructions in all areas of clinical negligence. Although he most commonly receives instructions from Claimants, he is comfortable acting for both claimants and defendants and is regularly instructed on behalf of NHS trusts around the Country in the Employment Tribunal.

  Harry’s practice involves instructions on both County Court and High Court matters, as well as in disputed inquests. He is comfortable with matters that are both factually and legally complex.

  His recent instructions include:

  • A case in which the Claimant suffered a spinal injury and became paraplegic as a result of delayed diagnosis to his spinal condition. The Claimant died 3 years later as a consequence of his paraplegia. Harry is instructed in connection with an ongoing inquest into the Claimant’s death on behalf of the bereaved family.
  • A case in which the Claimant alleges that the failure to seek appropriate specialist input led to the stillbirth of her child. The Claimant is said to have suffered severe psychiatric injuries as a result.
  • A fatal accident where the claimant died as a consequence of her GP refusing to prescribe her with anticoagulant medication. Harry represented the family of the bereaved at a 2 day inquest.
  • A case in which the Claimant’s treatment while under anaesthetic is alleged to have been directly inconsistent with the treatment plan of her treating consultant and was not the procedure she was consented for.
  • A case in which the Claimant alleges that her severed tendons initially went undetected upon examination, which delay in diagnosis and treatment affected the severity of her long-term symptoms.

• Investigations

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  Harry has experience in conducting internal investigations.

  Recent investigations in which he has been instructed include the following:

  • An investigation into an allegation that a manager had orchestrated a sham disciplinary process and sought to coerce witnesses into giving false evidence.The investigation later expanded to include allegations that the same manager was stealing from his employer.

  • An investigation into an allegation raised by two employees that they were being bullied by their manager. Complaints had previously been made, and Harry was also instructed to consider alleged retaliation by the manager.

  • An investigation into an allegation that an employee had been abusing drugs whilst at work. The same complainant also raised complaints about how she had been treated by her employer after previous disciplinary proceedings in which she was a witness, which Harry investigated as part of the same process.

  • An investigation into allegations that an employee had been using CCTV footage to spy on another employee outside working hours.

  • An investigation made by the mother of a young child after her request to change working hours was refused. The investigation included consideration of whether there had been maternity discrimination, given the recent changes to the complainant’s childcare situation.

   

• Off-payroll working (IR35)

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  Harry has extensive experience of worker and employee status disputes in the context of both employment and revenue litigation.

  Harry was instructed on behalf of the Taxpayer in the Supreme Court proceedings in Professional Game Match Officials Limited v HMRC [2024] UKSC 29 (led by Jonathan Peacock KC). That case concerns the employment status of football referees (for tax purposes) and gives rise to issues including the nature of mutuality of obligations and control for the purpose of the Ready Mixed Concrete test.

  Harry acted for the taxpayer in Kickabout Productions Limited v HMRC [2022] EWCA Civ 502 in the Court of Appeal (led by Jonathan Peacock KC). The case concerned a number of issues including the proper application of the Ready Mixed Concrete test and the proper construction of hypothetical contracts of employment for the purposes of IR35.

  Harry is instructed in an appeal in the Employment Appeal Tribunal against a finding that an employer made an unlawful deduction from wages in sums paid to a PSC in a four party arrangement that fell within IR35.

  Harry has previously assisted Marika Lemos on behalf of a taxpayer in preparing pre-action correspondence in relation to a dispute with HMRC over the application of the IR35 provisions.

• Industrial Disease

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  Harry accepts instructions in industrial diseases cases. Although he most commonly receives instructions from claimants, he is comfortable acting for both claimants and defendants. Harry was instructed as junior counsel to Robert Weir KC in the case of Cape Intermediate Holdings Ltd v Dring [2019] UKSC 38, a matter in which documents were sought relating to the liability of manufacturer’s of asbestos.

  Harry’s recent instructions include:

  A case in which the Claimant worked in a workshop producing construction materials and developed contact dermatitis as a result of exposure to wood dust and industrial adhesive.

  A case in which the Claimant developed vibration White Finger after using modified vibrating tools in the workplace. Limitation was complicated by the Claimant’s pre-existing diagnosis of Reynaud’s syndrome and the gradual development of his symptoms.