Bossing It: Being Out of Your Comfort Zone with Cressida Holmes-Smith

Cressida Holmes-Smith is CEO at Lucky Generals. Cressida has been with the agency since 2018, joining from BBH where she was a business director and partner on Tesco. At Lucky Generals, she soon became a client partner before being promoted to head of account management and ultimately MD in 2020.

LBB> What was your first experience of leadership?

Cressida> Captaining the school hockey team. I was fast and fiercely competitive. But sadly never talented enough to be captain of the netball team - ultimate teenage leadership goal. Still unfulfilled - I should probably let that one go. 

LBB> How did you figure out what kind of leader you wanted to be – or what kind of leader you didn’t want to be?

Cressida> By experiencing other people’s leadership; I know what’s felt really good to me in the past, and what really hasn’t. For me, integrity and inclusivity are both absolutely key. It’s hard to follow someone who isn’t genuine, or who doesn’t appreciate difference. 

LBB> What experience or moment gave you your biggest lesson in leadership?

Cressida> Seeing how true to herself Lucky Generals’ founder Helen Calcraft is, especially as a female leader. She never feels the need to embody any masculine tropes, and leads with her heart on her sleeve, sleeves fully rolled up. She’s fiercely passionate, high-energy, high-empathy, vulnerable, courageous, and totally at ease in herself. 

LBB> Did you know you always wanted to take on a leadership role? If so how did you work towards it and if not, when did you start realising that you had it in you?

Cressida> I’ve never consciously thought about it - and I still don’t now to be honest - but I’ve always wanted to continue learning and pushing myself out of my comfort zone. Leadership was very much out of my comfort zone.

LBB> When it comes to 'leadership' as a skill, how much do you think is a natural part of personality, how much can be taught and learned?

Cressida> I think there has to be an inherent reason why people might want to be led by you; it could be creative talent, empathy, an infectious drive and energy… and then the rest can be taught and learned by working for brilliant leaders. 

LBB> What are the aspects of leadership that you find most personally challenging? And how do you work through them?

Cressida> There’s never enough time and you can’t be in all places at once. I’ve had to learn to delegate more, to prioritise the big impact stuff, and to be more at ease with imperfection and the unknown, trusting my instincts and happily surrounding myself with highly fun and talented people.

LBB> Have you ever felt like you've failed whilst in charge? How did you address the issue and what did you learn from it?

Cressida> How about every day? But I’m genuinely okay with failure as I don’t think perfection is a good model for leadership; if you want people to grow, they need to feel that it’s okay to fail along the way. Just do it fast and with integrity. Acknowledge it, correct it, learn from it, go again.

LBB> In terms of leadership and openness, what’s your approach there? Do you think it’s important to be as transparent as possible in the service of being authentic? Or is there a value in being careful and considered?

Cressida> I would say I’m pretty open, but I think there’s a middle ground. People don’t need or want to hear everything, most of the time. But understanding the why and the wider context can be helpful for people, as is sharing vulnerability, as it encourages empathy and bravery in turn. So I’m going to go with considered transparency.

LBB> As you developed your leadership skills did you have a mentor, if so who were/are they and what have you learned? And on the flip side, do you mentor any aspiring leaders and how do you approach that relationship?

Cressida> I’ve been grateful for multiple mentors, both formal and informal - ex-bosses, ex-clients, ex-colleagues - who I can call on for support and advice, as well as Melissa Robertson, CEO of our sister company and Sports & Wellbeing specialists, Dark Horses who has been a patient and regular sounding board in recent years. 

I’ve also recently worked with the Women’s Association to provide Mentorship to young women who might not see themselves as a leader or even in this industry - for them, I try to be relatable and show that it’s not out of reach, as well as helping with practical steps.

LBB> In continually changing market circumstances, how do you cope with the responsibility of leading a team through difficult waters?

Cressida> It’s pretty much all I’ve known as a senior leader, having taken on the managing director role mid-Covid. I see leadership as a privilege to enjoy, not a responsibility to bear, and I like having problems to solve. Plus the answer is always the same - make great work and the rest will follow.

LBB> As a leader, what are some of the ways in which you’ve prioritised diversity and inclusion within your workforce? 

Cressida> Lucky10Grand 

We recently partnered with Effie UK to fund £10K worth of marketing effectiveness training for working-class talent.

The initiative, Lucky10Grand is designed to mark both the agency's 10th birthday and its recent winning of the UK's top effectiveness prize - the Grand Effie - for its long-running campaign for Yorkshire Tea.

The fund will be administered by the social enterprise Commercial Break, with whom Lucky Generals has its own long-running relationship.

- Hiring and Work experience

Our hiring processes focus on blind hiring and panel interviews to reduce the risk of any unconscious bias, and we have reviewed our external recruitment partners to ensure we’re only working with agencies who share our values and commitment to better inclusion and diversity.

- Speakers 4 Schools

We have partnered with S4S, running week-long work experience programmes to give valuable insight to state school kids and are hoping to launch a 6-month internship programme next year to find our next generation of Generals.

- Revised policies

We’re really proud to have launched new policies including enhanced maternity & pregnant parent policy that offers 6 months paid leave; transitioning at work; period and menopause policies and a brand-new fertility policy with time-off and funding options so we can best look after our Generals when it really matters.

LBB> How important is your company culture to the success of your business? And how have you managed to keep it alive with increases in remote and hybrid working patterns?

Cressida> One feeds the other, and vice versa. Our success depends on our entrepreneurial, highly creative, fun-loving culture, and our success feeds that culture. If you’re making great work and winning pitches, whilst having fun, people are happy and fulfilled. We take the work very seriously, but not ourselves. And that doesn’t change whether we’re in the office or working from home.

LBB> What are the most useful resources you’ve found to help you along your leadership journey?

Cressida> Shout out to Creative Equals’ Business Leaders course and to Self-Space - both supported by Lucky Generals. Also shout out Lorraine.