For Helen Kennedy-Shamir, Chief Legal Officer at Checkatrade, it’s about understanding the business, communicating effectively and having the confidence to bring your personality to work.
Being approachable, building genuine relationships and being someone people actually want in the room are all part of Helen’s approach to leadership. From making time for fun with her team to her funny out-of-office messages, she shares why there’s room for humour and personality at work, even in a senior leadership role.
Helen has lived nearly every version of the in-house legal journey: private practice in Newcastle, a move to London, investment and listed-company work, big-company pressure, pandemic-era crisis management, and finally a role she calls the best job she’s ever had. Along the way, she learned that the jump from lawyer to trusted business leader has less to do with legal theory and more to do with judgement and communication.
You’ll hear how Helen moved from private practice into in-house life, what it really takes to adapt when your world shifts from advising clients to becoming the client, and why budgets, risk appetite, and board-level communication can feel like a completely different language. She also shares the defining lessons from working through COVID, maternity leave in the middle of global disruption, and a major takeover, and how those experiences shaped her as a lawyer and leader.
We break down:
Why broad experience matters more than a narrow legal lane
How top in-house lawyers talk in numbers, not just words
What great GC leadership looks like when you’re building trust, not just giving advice
How coaching, mentoring, and visible personality shape stronger teams
Why being in the office four days a week helps Checkatrade move faster and deliver higher-quality work
Helen also explains what she looks for when hiring, why “people, not roles” is the mindset that changes everything, and what aspiring GCs should prioritise if they want to become genuinely useful to a business, not just legally correct.
Her answer to what she wants to be remembered for is as clear as it is refreshing: how she made people feel, and that working with her felt worthwhile and enjoyable.
Essential listening if you’re an in-house lawyer, an aspiring GC, or a business leader who wants legal to be a strategic advantage rather than a bottleneck.
