Leaders with Ambition - Lesley O'Leary

Lesley O'Leary - Chief Operating Officer at Charles Russell Speechlys

We’re constantly evolving – towards ever better things – so long as we stay curious! That’s the message from Nicky Acuna Ocana’s guest on this episode of Leaders with Ambition. Lesley O’Leary’s career provides a vivid roadmap for what it looks like to maximise potential and do so with delight.

As Chief Operating Officer at Charles Russell Speechlys, she incorporates lessons throughout her varied career (in real estate as well as legal services spaces) to create a workplace culture based on inclusivity, personal development and innovation. Lesley has stayed open to growth and connection at every stage, welcoming challenge and learning how to advocate for herself – and then by extension for those that she has gone on to lead.

She shares thoughts on how her leadership style has taken shape and the role of both mentoring and networking in getting her there. You’ll learn about the power of staying curious and engaging with a coach as well as what secret ingredients have helped this busy marketing and business development professional stay grounded and happy in both her family and career.

The episode includes a fantastic tip for introverts navigating business events and encouragement for those cultivating the confidence to speak up at the table. And, speaking of using our voices, Lesley also leaves us with parting words of wisdom, including: Don’t be afraid to ask!

Says our dynamic guest: “If there’s something you want to do, you need to tell somebody and work out a plan. And if it’s not (a job) they see in their future, that’s alright too!”

If you enjoyed this discussion, please click here to find previous episodes of Leaders with Ambition.

Key Takeaways

Starting out

Raised on the Isle of Skye, Lesley’s early life was happy but remote, inspiring her to explore world travels and pursue university (the first in her family).

Entry level

Role models and mentorship start with even our earliest work experiences, which is how Lesley acquired some of her early career skills while working in real estate.

Levelling up

How Lesley put marketing and sales development skills acquired in the real estate sector to work while leap-frogging through a series of roles in London.

Lesson in self-care

What Lesley learned as a new mum who suffered post-partum depression at a time it was little understood. Supporting your own well-being matters!

Knowing yourself

How Lesley came to understand the significance work had in her life and how she succeeded in integrating it with family life – thanks in part to the professional (and personal) network she had developed.

Speaking up

Why learning to use her voice and act with confidence were key to Lesley fully taking her place at the corporate table.

Mentoring matters

What Lesley does to ensure she’s always engaging with and extending her network, for her own development and the development of others.

Tip for introverts

Get to networking events early, when it’s much easier to connect with other attendees!

It’s a match

Why Lesley enjoys working in the legal field – the intellect, challenge and chance to develop evidence-based sales and marketing strategy (first at Herbert Smith Freehills, then Travers Smith).

Work-life balance

How Lesley has learned to put in place healthy boundaries to protect her well-being against competing demands and chronic people-pleasing.

Family dynamics

Why clear communication and collaboration is foundational (and essential) for dual-earning couples who want to raise children… in harmony!

Changing course midstream

What it looks like to reverse a big decision (like relocating to Australia!) at the last minute and come out well, both professionally and personally.

Strategic shift

About Lesley’s intentional migration from transactional marketing and BD work to bigger-picture advisory and leadership roles at Charles Russell Speechlys.

It’s another match

How the COO’s mandate to solve problems, motivate people and remove roadblocks fits well with Lesley’s skill set, attributes and interests.

Leadership philosophy

Why Lesley sees her job as a leader of peers. It’s not to know everyone’s job but to provide the right tools to help them to flourish in their roles.

Future-proofing

About the importance of staying curious, engaged and ahead of ongoing developments impacting legal services (such as the emergence of AI).

Key resources for supporting EDI

Staying curious.
Seeking out reverse mentorship.
Working to ensure an even playing field.
Creating space for everyone to bring their authentic self to work.
Be willing to learn from mistakes!

Advice for leading healthy workplaces

Create a culture that supports just “being” as opposed to constantly doing.
Carve out space for self-reflection.
Schedule time to review what’s working and not and how things might change.
Always say yes to coaching, and be an active participant in the process!
Keep learning through podcasts, reading, networking.

Evolving into leadership

How Lesley culled her experiences with managers (good and bad) to evolve her own style in combination with professional development resources.

Current biggest challenges for COOs

“Permanent crises” in geopolitics – elections, conflict, markets, etc.
Managing office space and usage in a hybrid world.
Workplace productivity as well as support.
Figuring out how to strike a hybrid balance of in-office and remote.

Culture of collaboration

Why Lesley emphasises teamwork and leverages a variety of voices and expertise to innovate and solve problems (small and large).

Change & opportunity

About Charles Russell Speechlys’ focus on AI as a means to support client experience, providing tools that meet needs and accelerate goals.

Lesley’s career highlights

Feeling that she makes a difference and adds value.
Interacting and learning from – as well as teaching – great people.
Helping to develop and promote careers.

Words of wisdom

'Be brief.'
'Back yourself.'
'Ask for the job! And know that, if it doesn’t work out, that’s okay too!'
'Make sure you feel that what you do – whatever it is – matters.'
'Be able to take feedback, adjust and pivot moving forward.'

Key quotes

“It’s not just thriving and asking for the roles that you want but having the confidence to ask for it as well!” (Nicky)
“Being a stay-at-home mum is not for everybody. I respect those that make that choice and it works for them, but I love work… and when I’m happy I think the family tends to be happy as well.”
“The (business) relationships that we build over time are important. They’re a great foundation in all of our lives. People genuinely do want to help each other if they can.”
“(Speaking up) is about trusting yourself and that comes with age and confidence.”
“I love the intellect of lawyers. I like the challenge of presenting them with evidence!”
“I’m an unusual pick for COO. My background is not finance but for us as a business that’s not what it’s about … It’s about client service excellence.”
“I like problem-solving, taking things apart and putting them back together, and a lot of a COO’s role is dealing with inertia and trying to make things happen.”
“Being experimental might not be encouraged in some law firms … but how are we going to grow or have an entrepreneurial spirit if we’re not willing to learn from our mistakes?”
“We’re so busy ‘doing’ sometimes (but) we’re human beings and need to take time out just to ‘be’ rather than ‘do’ all the time!”
“Everyone is brilliant at telling you what the problems are, but to solve a problem takes a team. So you’ve got to get the right team around the table.”
“Don’t assume that everybody else is a mind-reader. If there’s something you want to do, you need to tell somebody and work out a plan. And if it’s not something they see in your future, that’s alright too!”

About Lesley O’Leary

Working in partnership with the Managing Partner and Senior Partner, Lesley provides executive oversight and leadership of the firm’s operational professionals to help Charles Russell Speechlys implement its plans for increased profitability, innovative working practices and processes in alignment with the firm’s strategy, aspirations, brand and values.

Initially joining the firm to lead its Business Development & Marketing function, Lesley has more than 25 years of experience enabling partnerships to provide creative solutions for clients.

About Nicky Acuna Ocana

Nicky has led high performing recruitment teams for over 25 years. As the Regional Managing Director of Ambition UK, Europe & US, she leads a team of highly-skilled recruitment consultants who are experts in their niche specialist areas. With an extensive network of senior and board-level contacts, she is also heavily involved in Executive Search, focusing on Director level appointments across Business Services for a range of Professional Services firms.