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Enter the Boardroom

Enter the Boardroom

Enter the Boardroom Community 187 episodes Nov 11, 2026

Enter the Boardroom is a weekly podcast from the Enter the Boardroom Community. Host Oliver Cummings, CEO of Nurole, interviews leading chairs, board members, CEOs, and academics to uncover insights and hard-won lessons rarely shared publicly. The show aims to help listeners sharpen their board proposition and build a network of serious peers. It also promotes the community's deeper resources and offers a discount for listeners.

Episodes

199. Jacqueline de Rojas CBE: The most impactful questions in the boardroom
199. Jacqueline de Rojas CBE: The most impactful questions in the boardroom Nov 11, 2026 39:57 Jacqueline de Rojas is Chair of the Bletchley Park Trust. Throughout her career she has championed greater inclusion in technology and leadership. Listen to this episode to hear about: The search firm call that led to her first board seat (01:40) What she noticed when she met the board in separate rooms (04:31) Going from knowing things to asking things (10:24) The one question she’s dropped from
198. Alexander S. Hoare: How non-execs add value to an eleven generation family bank
198. Alexander S. Hoare: How non-execs add value to an eleven generation family bank Nov 4, 2026 39:26 Alexander S. Hoare is an eleventh-generation partner and director of C. Hoare & Co, the oldest privately owned bank in the UK. Listen to this episode to hear about: What it’s like to govern a bank when your own house is the collateral (01:25) The non-exec who stepped into a family war, and the question that ended it (06:22) How many non-execs is enough, and the dining table that sets the limit
197. Dr. Annalisa Jenkins OBE: How to build a plural career - lessons from 50+ board roles
197. Dr. Annalisa Jenkins OBE: How to build a plural career - lessons from 50+ board roles Oct 28, 2026 42:40 Dr. Annalisa Jenkins has held around fifty board and trustee roles across biotech, venture capital, public bodies and medical charities, including Compass Pathways, AVROBIO, Affimed and Mereo BioPharma. Tune into this episode to hear more about: The cold call that led to Annalisa’s first public board seat (01:37) The CV mistake that keeps first-time NEDs off boards (04:14) Two things Annalisa chec
196. Conor Boden: How private equity decides who gets the board seat
196. Conor Boden: How private equity decides who gets the board seat Oct 21, 2026 40:40 Conor Boden spent over two decades building boards for private equity funds. He was Head of Portfolio Board Development at Advent International. Listen to this episode to learn more about: What decides who private equity appoints as a chair or NED (01:42) Where to focus your time when no private equity board role is on offer (05:18) How private equity weighs track record against potential  (10:05)
195. Debbie Hewitt MBE: Chairing the FA - how to do the top job in the face of public scrutiny
195. Debbie Hewitt MBE: Chairing the FA - how to do the top job in the face of public scrutiny Oct 14, 2026 40:55 Debbie Hewitt MBE is Chair of The Football Association, the first woman to hold the role in its history. She is also a Vice-President of FIFA. Alongside football, she chairs Visa Europe and Compare the Market. Tune into this episode to hear about: Common misunderstandings about the FA (02:36) How to prioritise amongst stakeholders (05:30) How Debbie decides when to step in (09:08) Working with gov
194. Matthew Lester: How a chair finds out what's really going on inside the business
194. Matthew Lester: How a chair finds out what's really going on inside the business Oct 7, 2026 41:49 Matthew Lester is Chairman of Kier group plc and NED and Chair of the Audit Committee at Intermediate Capital Group plc. Previously, he was CFO of Royal Mail plc. Listen to this episode to learn more about: Two moments where non-execs had the biggest impact on the business (01:39) Why motivation outweighs knowledge in CEO hires (08:03) The hardest habit to break when you become a chair (16:21) How
193. Dame Hayaatun Sillem: How to use early board roles to accelerate your exec career and set up a non-exec portfolio
193. Dame Hayaatun Sillem: How to use early board roles to accelerate your exec career and set up a non-exec portfolio Sep 30, 2026 44:36 Dame Hayaatun is the founder and CEO of Argentic Associates. Previously, she was CEO of the Royal Academy of Engineering and the Queen Elizabeth Prize for Engineering Foundation. Listen to this episode to learn more about: How a non-exec role helped carve Dame Hayaatun’s path to CEO (01:35) How she landed her first non-exec role (11:22) How sitting on boards helped her improve in her day job (15:1
192. Nick Wheeler OBE: The tortoise who built Charles Tyrwhitt - focus, founders and knowing when to step back
192. Nick Wheeler OBE: The tortoise who built Charles Tyrwhitt - focus, founders and knowing when to step back Sep 23, 2026 46:47 Nick Wheeler OBE founded Charles Tyrwhitt in 1986 from his university room in Bristol. Forty years later it is a £400 million revenue business operating across the UK, US, and Europe. Listen to this episode to hear about: The tortoise rule: why the first 20 years are boring and the next 20 get exciting (04:34) Why the best business decision Nick ever made had nothing to do with shirts (08:03) The
191. Debbie Wosskow CBE: How entrepreneurs can become high-impact board members
191. Debbie Wosskow CBE: How entrepreneurs can become high-impact board members Sep 16, 2026 44:42 Debbie Wosskow CBE is one of the UK's best-known entrepreneurs. Today, she is NED of Channel 4 and co-chair of the government-backed Invest in Women Taskforce. Tune into this episode to hear about: Debbie's discipline around cash (01:17) Picking your boards wisely: what’s on the line as a non-exec (08:32) Why storytelling is important for founders (09:48) What surprised Debbie the most d
190. Sir Lloyd Dorfman CBE:  Why boards need to encourage more persistence and risk - lessons from Travelex and the Royal Ballet and Opera
190. Sir Lloyd Dorfman CBE: Why boards need to encourage more persistence and risk - lessons from Travelex and the Royal Ballet and Opera Sep 9, 2026 41:18 Sir Lloyd Dorfman CBE is founder of Travelex, the world's largest retailer of foreign exchange. Today, he is Chair of the Royal Ballet and Opera and sits on the Mayor of London's Business Advisory Board and is Chair of Dorfman Media Holdings. Listen to this episode to hear about: How Sir Lloyd talked his way into Heathrow Terminal 4 (01:35) How Travelex outbid the clearing banks for the
189. Jacqui Ferguson: How boards choose a chair, and how to be the one they pick
189. Jacqui Ferguson: How boards choose a chair, and how to be the one they pick Sep 2, 2026 40:44 Jacqui Ferguson started her career as a technologist in Scotland and rose to become a divisional CEO at Hewlett Packard. Today, she is a SID at Croda International plc and NED at National Grid plc. Listen to this episode to hear about: How Jacqui found out she was becoming chair of Tesco Bank (01:52) How a board actually decides who becomes its next chair (08:27) Working for Meg Whitman during Hew
188. James Thornton: How to get founder-to-CEO succession right
188. James Thornton: How to get founder-to-CEO succession right Aug 26, 2026 43:17 James Thornton is CEO of Intrepid Travel, the world's largest adventure travel B Corp, operating in more than 100 countries with $809 million in revenue and 317,880 customers in 2025. He became the company's first non-founding CEO succeeding co-founders Darrell Wade and Geoff Manchester. Tune into this episode to hear about: The five-year test: how James was quietly auditioned to become

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