Enter the Boardroom

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Episodes

197

Latest episode

Oct 2026

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EN-GB

About the show

Enter the Boardroom is the podcast of the Enter the Boardroom Community. Each week, Nurole CEO Oliver Cummings sits down with leading Chairs, board members, CEOs and academics, drawing out the insights and hard-won lessons that rarely get shared in public. If you enjoy the podcast, the Community goes much deeper. You'll sharpen your board proposition, build a network of serious peers, stay current on the issues reshaping boardrooms, and access opportunities you won't find anywhere else. Visit etb.nurole.com to find out more. Listeners get a 10% discount by applying the code ENTER at checkout.

Listen to episodes

60 recent

October 28, 2026Episode 19742 min

197. Dr. Annalisa Jenkins OBE: How to build a plural career - lessons from 50+ board roles

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 checks before joining any board (05:55) How she earned a reputation for replacing CEOs (12:23) Life as a CEO, IPOs and genetic risks (15:20) Joining a board with no diligence, and what happened next (18:21) Losing a chair role by misreading the investors (21:33) A mental model for non-execs joining a biotech board (25:13) Running twenty boards, and her criteria for selecting board roles today (30:22) ⚡The Lightning Round⚡(36:42) Support the show Host : Oliver Cummings Producer : Will Felton Editor : Penelope Coumau Music : Kate Mac Audio : Nick Kold Email: podcast@nurole.com Web : https://www.nurole.com/nurole-podcast-enter-the-boardroom

October 21, 2026Episode 19640 min

196. Conor Boden: How private equity decides who gets the board seat

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) How to move from someone's radar into an interview process (14:21) Psychometrics versus other assessment techniques (19:48) The most common reason credible candidates miss out (21:37) Whether you can change how you come across in a private equity interview (23:01) The board intervention that changes a business most (25:19) Why chairs and NEDs don’t get invited back (30:55) ⚡The Lightning Round⚡ (33:41) Support the show Host : Oliver Cummings Producer : Will Felton Editor : Penelope Coumau Music : Kate Mac Audio : Nick Kold Email: podcast@nurole.com Web : https://www.nurole.com/nurole-podcast-enter-the-boardroom

October 14, 2026Episode 19540 min

195. Debbie Hewitt MBE: Chairing the FA - how to do the top job in the face of public scrutiny

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 governance rules created in 1863 (11:12) Why Debbie didn’t immediately push for women's clubs to join the FA (15:00) What CEO succession teaches you about choosing an England manager (20:10) The personal cost of chairing the FA (22:18) Three questions to ask yourself before you speak to the press (29:30) Debbie’s mistakes, building a portfolio (31:12)⚡The Lightning Round⚡(37:42) Support the show Host : Oliver Cummings Producer : Will Felton Editor : Penelope Coumau Music : Kate Mac Audio : Nick Kold Email: podcast@nurole.com Web : https://www.nurole.com/nurole-podcast-enter-the-boardroom

October 7, 2026Episode 19441 min

194. Matthew Lester: How a chair finds out what's really going on inside the business

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 Matthew checks whether the board is getting the full picture (22:18) The case for giving employees a seat in the boardroom (31:06)⚡The Lightning Round⚡ (33:54) Support the show Host : Oliver Cummings Producer : Will Felton Editor : Penelope Coumau Music : Kate Mac Audio : Nick Kold Email: podcast@nurole.com Web : https://www.nurole.com/nurole-podcast-enter-the-boardroom

September 30, 2026Episode 19344 min

193. Dame Hayaatun Sillem: How to use early board roles to accelerate your exec career and set up a non-exec portfolio

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 (15:16) Two moments Dame Hayaatun felt like the board added the most value (18:52) Why asking for more information can create a bottleneck (26:09) Where non-execs cross the line with management (28:36) A 3-step framework for deciding what’s next: motivation, aspiration, consideration (35:22) ⚡The Lightning Round⚡(38:52) Support the show Host : Oliver Cummings Producer : Will Felton Editor : Penelope Coumau Music : Kate Mac Audio : Nick Kold Email: podcast@nurole.com Web : https://www.nurole.com/nurole-podcast-enter-the-boardroom

September 23, 202646 min

192. Nick Wheeler OBE: The tortoise who built Charles Tyrwhitt - focus, founders and knowing when to step back

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 fine line between founder magic and founder interference (12:27) Why Michael Dell's £158 billion business still annoys Nick (19:38) The expansion mistake that sent Charles Tyrwhitt bust (21:02) Why a great interview tells you almost nothing - and what Nick does instead (26:18) The difference between building a brand and building a business (32:12)⚡The Lightning Round⚡(34:30) Audience Q&A (39:31) Support the show Host : Oliver Cummings Producer : Will Felton Editor : Penelope Coumau Music : Kate Mac Audio : Nick Kold Email: podcast@nurole.com Web : https://www.nurole.com/nurole-podcast-enter-the-boardroom

September 16, 2026Episode 19144 min

191. Debbie Wosskow CBE: How entrepreneurs can become high-impact board members

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 during her first exit (16:55) The Series B decision that split the Love Home Swap board (18:53) Three questions a NED should ask before accepting investment (26:07) "Organ donor rejection": why big names don't always survive in startups (28:49) How Debbie built her portfolio career (38:04) ⚡The Lightning Round⚡(42:08) Support the show Host : Oliver Cummings Producer : Will Felton Editor : Penelope Coumau Music : Kate Mac Audio : Nick Kold Email: podcast@nurole.com Web : https://www.nurole.com/nurole-podcast-enter-the-boardroom

September 9, 2026Episode 19041 min

190. Sir Lloyd Dorfman CBE: Why boards need to encourage more persistence and risk - lessons from Travelex and the Royal Ballet and Opera

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 Heathrow contract (09:06) Why entrepreneurial businesses see opportunities incumbents miss (14:04) Why Sir Lloyd bet Travelex on a £440m acquisition (16:05) The integration lesson from the £440m Thomas Cook acquisition (20:47) The challenge of leading a cultural institution after COVID (24:32) Why he banned hybrid board meetings (28:17) The mistake nonprofits make about commerciality (31:42) ⚡The Lightning Round⚡(34:34) Support the show Host : Oliver Cummings Producer : Will Felton Editor : Penelope Coumau Music : Kate Mac Audio : Nick Kold Email: podcast@nurole.com Web : https://www.nurole.com/nurole-podcast-enter-the-boardroom

September 2, 2026Episode 18940 min

189. Jacqui Ferguson: How boards choose a chair, and how to be the one they pick

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 Hewlett-Packard’s $8bn turnaround (10:12) Leading the search for Croda’s next chair, and why there’s no such thing as a perfect candidate (14:57) The 30 days it takes to run a FTSE 100 chair search (19:21) What separates the finalists in a chair search (22:13) Why Softcat kept its chair past the nine-year limit (25:38) The succession maths that made Jacqui rule herself out at Croda (30:44) Why 12 months as chair designate creates more problems than it solves (33:38) Support the show Host : Oliver Cummings Producer : Will Felton Editor : Penelope Coumau Music : Kate Mac Audio : Nick Kold Email: podcast@nurole.com Web : https://www.nurole.com/nurole-podcast-enter-the-boardroom

August 26, 202643 min

188. James Thornton: How to get founder-to-CEO succession right

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 CEO (01:38) His advice for any founder building a CEO (04:31) Why becoming CEO felt anticlimactic (08:16) The founder trick for empowering a CEO without micromanaging them (12:55) How to stress-test an acquisition (18:50) What James looked for when hiring board members (22:22) Running a travel company through Covid (34:14) The advice James would give himself looking back on his nine-year journey (37:43)⚡The Lightning Round⚡(39:44) Support the show Host : Oliver Cummings Producer : Will Felton Editor : Penelope Coumau Music : Kate Mac Audio : Nick Kold Email: podcast@nurole.com Web : https://www.nurole.com/nurole-podcast-enter-the-boardroom

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