Harry Watling was announced as part of Rob Edwards' coaching staff following his appointment in June 2025.

His coaching journey began at the age of just 15. He quickly obtained his badges, including the UEFA B Licence aged 18. He joined Chelsea as a development centre coach aged 19, and later progressed to work within the club’s Academy. 

After five years at Chelsea, Harry was with Millwall from 2014 to 2018, coaching the Under-15s and U16s. He also spent time in a similar role at West Ham United before becoming head coach of Hartford Athletic in the United States in 2020.

While with the USL Championship club – one tier below MLS – Hartford set records for most goals, points and clean sheets in their history. He resigned from his role in June 2022 to return to England for family reasons.

A month later he was appointed first-team development coach with Queens Park Rangers, who started the 2022/23 campaign in fine form. The coaching staff, including Harry, moved to Rangers in November 2022, where they remained until October 2023

Harry was appointed manager of National League club Ebbsfleet United in September 2024, and departed by mutual consent later that year.

He returned to football with Boro to form a vital part of Edwards' staff.