10 Questions on Advertising… with Lucky Generals’ Helen Calcraft

But she’s also run those agencies with a huge dollop of empathy, understanding what it takes to not just say the right thing but do the right thing too. She’s launched hugely important industry initiatives such as TimeTo, which tackles sexual harassment in the advertising industry, and a Cancerversary policy, which sees agencies like hers offer a day off to anyone who has undergone cancer treatment to take a day out each year to process, grieve, celebrate and simply breathe.

So yes, if we were to start with anyone, we wanted it to be Helen. And she was kind enough to say yes. Because kind she most definitely is. We hope you find her answers – and all the answers shared in this series – to be as inspiring, insightful and powerful as the subjects themselves.

1. If you could go back and relive one day in your career, which would it be?

There have been so many incredible days, so this is nearly as bad as being asked to name your favorite film! But if I had to name one, I think it would be the day we won the Twitter pitch.

At the time, Lucky Generals was not yet a year old, and as a self-funded startup, we were still having some dark days, wondering whether we could make a success of this venture. Twitter was our first major competitive pitch against the best of the best in our industry. It was also one of the most exciting brands on the planet at that time.]

To this day that pitch remains one of the best presentations I have ever been a part of. The thinking and the work was transformative, and we all brought our A-game. Thankfully, the client team agreed, and that “yes” call was one of the greatest moments of my whole career.

2. Now tell us about the day that still gives you nightmares.

One day does stick out as being deeply distressing. We were in the depths of Covid – no one had the tools to cope with the sudden and seismic change to our lives. As a small, ramshackle, young, creative company our entire success had been rooted in community and camaraderie. Immediately after the third lockdown was announced, things felt bleak.

So I decided to ditch the Teams screens and simply telephone everyone at the agency to ask, on a human level, how they were doing. We had taken the decision to take pay cuts to ensure that not one redundancy would be made at this time, so I think everyone felt safe to be vulnerable.

The stories of loneliness, isolation, claustrophobia, anxiety, depression, grief, fear, loss, and overwhelm were harrowing. Although many of the Generals told me they appreciated the chance to simply talk, I felt pretty helpless and hopeless. There are days when that whole period feels like a strange dream. In fact, for so many, it was a nightmare.

3. Who gave you the piece of advice you still live by – and what was it?

As a recovering people-pleaser, something I have wrestled with all my life is a fear of burdening others. This has meant that I always have my hand in the air to take on responsibility and, if in doubt, I have done things myself rather than ask others to do them.

One of the best pieces of advice I was ever given as I stepped into leadership was from the remarkable and resplendent Juliet Timms. We were talking about how to be a great managing director, and she said, “Here’s how. As soon as something lands on your desk, pause and ask yourself – who can I give this to?”

She is so wise. If you are trying to be a good leader, the answer is not, “Oh gosh, I will just do that as it will be easier/quicker/kinder to others.” If you’re a one-person agency, you aren’t empowering anyone, you aren’t allowing others to rise, and you will burn yourself out. This is the first piece of advice I now give to people on promotion day, so I am paying it forward. Thank you, Juliet!

4. What piece of work done by someone else are you truly jealous of?

I am drawn to, and occasionally utterly jealous of, work that unites a profound human insight with astonishing creativity (you know, the work that seem so obvious in hindsight because the insight is both universal and true, and it feels like it’s been hiding in plain sight). This kind of work is exemplified by the timeless Guardian Points of View ad. It feels so current, over 30 years on.

I am also jealous of Like a Girl, and more recently, the blindingly clever WoMen’s Football campaign challenging unconscious gender bias head-on, right before the 2023 World Cup.

5. What’s your elevator pitch to people thinking about getting into the advertising industry for the first time?

There has never been a more exciting time to join this industry. Brands matter more than ever, and they are being built in a whole new way, with technology that is there to be harnessed, not feared. So, you can be a pioneer! And for people starting out today, there is a chance to progress at pace based on merit (rather than taking notes and pouring coffee for years like my generation did). You get to teach as well as learn, and to make a difference from the get-go.

6. What drives you to start your own agency… and what drives you to do it twice!?

If I am honest, I am something of an accidental entrepreneur. Just before I co-founded my first agency, I did an MBA and was offered a vast array of courses on setting up your own business, but I didn’t even take one of them as I didn’t imagine I would ever do that. One month after completing the MBA, my first boss, Jeremy Miles, asked me to start an agency with him. Doh! But at least I had the courage to say yes without hesitation.

Once I experienced entrepreneurship, I fell in love with it. But even then, I don’t think I would have started a second agency without my partners, Danny and Andy. My work life has been defined by great partnerships and I know for sure that in adland, successful startups are a team sport.

7. You’re a self-confessed new business junkie. What’s the very first thing you do when a big new brief comes in?

You are right – I bloody love new business! And I have done a lot of it over the years. Being the person who gets the call is the best and the worst job in the industry. And I have learned the hard way from the “no” calls that it isn’t enough to answer the brief/be correct with your strategic thinking/show amazing work/have the best chemistry.

To win, you must be obsessed with winning. Because nine times out of 10, there is a millimeter between you and the team coming in second. So, pretty much the first thing we do when the brief comes in is to get in a room and ask, “What will it take to win this?”

8. In Hovis, you guys created the ad of the decade. At what point do you know when a campaign like that is going to be special?

I think you know if the work is going to be special the night before you present it to your client. You know when an idea is powerful when it can be articulated seamlessly in single sentence, or a few words or just one image. If this this simple promise comes with goosebumps, you are on to a winner.

For Hovis, the whole presentation was three words:

· Boy

· Bread

· Britain

A boy is sent out to the shops by his mam to buy a loaf bread for his tea and runs all the home through 122 years of history in Britain (inextricably linking the brand to the story of this country). And just like that, Hovis was restored as a heart of the nation brand.

9. Lucky Generals seems to thrive working on big, populist, fun brands (as did MCBD). What’s the secret to winning and working with those?

That’s so true. My partnership with Danny and Andy was born of creating what was voted by the British public as their ad of the decade. Over a decade later and in a different agency, one of our proudest moments at Lucky Generals was when the American public voted our ad for Amazon's Alexa to be their favorite ad of the Superbowl. We were the first British agency to ever achieve the number one spot. We have created the most viewed ad of the year worldwide on YouTube four times in the last eight years, and we always aim to create work that moves people.

It is such an honor for people to love your work, to talk about it, to seek it out and to share it. Clients can feel it when you genuinely care about what real people think, more than you care about a room full of people in a London hotel wearing dickie bows. They know they can trust us to do right by their brand.

10. Across AMV, MCBD and Lucky Generals, you’ve worked on some pretty fun and illustrious brands. But what’s the one brand in your career that’s got away?

Gosh, there have been many wistful and even heartbreaking moments when a pitch hasn’t gone our way. Some brands you really do fall in love with, and it truly hurts when you’re told you aren’t “the one.”

But weirdly, the brand that still hurts my heart the most goes back to the first question in this interview. One of the most thrilling moments of my career was winning Twitter. But we never got to execute the strategy and make the work that won the pitch (due to so many changes and pressures at Twitter). Now, the Twitter we knew and loved has truly gone. And the spirit and integrity of that magical brand has an ugly black x where a beautiful bird used to be. Yep. That’s the brand that got away, not just from me, but from everyone with a soul.