Bossing It: For Bridget Flynn We’re All in This Together
As CEO of the Grayson Music Group, a group of music focused companies, Bridget Flynn combines strategic and creative thinking to help develop ground-breaking work and drive the brand forward. Her favourite place to play is at the intersection of business, creativity and technology, with a focus on promoting the value of music, artists and copyright, forging new partnerships and exploring new directions – the key to creative growth and opportunity.
LBB> What was your first experience of leadership?
Bridget> My parents letting me boss them around from the age of three.
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?
Bridget> I’ve always had a job since I was 12 years old. So I’ve had all sorts of “bosses” in my time. I think to become a great leader you must first experience being led - both the good and the bad. Take it all in. When you move into a leadership role, your daily experiences should further shape how you lead.
In other words - the best leaders recognise the need to constantly evolve, learn and be flexible based on the needs of the business and their team. I strive to lead from a place of authenticity, experience and accountability.
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?
Bridget> I guess so? It is a role which seems to have come naturally to me for most of my life. Leadership doesn’t necessarily mean you are at the top of the org chart. Leadership happens at every single level of organisations. So “working towards it” is not necessarily how I would look at things - leadership opportunities are there for the taking if you want them - no matter who you are or what you do.
As long as you are in it for the right reasons, you build from there and it should be pretty straightforward.
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?
Bridget> I think the initial drive to lead is likely something that is naturally a part of a person’s identity. Not everyone is a leader and that is totally cool. However, it is impossible to be a great leader without constantly learning from others - whether other leaders or more importantly your team.
Obviously some leaders are better than others. While there is no one style of leadership that is the best, those who operate from a place of self-interest or insecurity are going to have a tough go. It’s never about you, it’s about the business and most importantly the team of people you are working alongside of.
So learning to be better at recognising this and the ways in which you can bring this to the table every day should never end.
LBB> What are the aspects of leadership that you find most personally challenging? And how do you work through them?
Bridget> One of the biggest challenges I have faced personally is releasing or curbing my need to and for control. It is hard for me, and it is something I work on daily. Leaders are decision makers. They usually or often have the final say. Great leaders are good at making decisions and choices. The process for making decisions however can take many forms.
The most effective way I have found to release that self-interested desire to control is to use perception over opinion in my decision making process. Perception is objective based on observation and the information at hand, while opinion is subjective and often judgemental.
Over the years I have learned to trust my gut, but to also step back, listen, and be flexible and comfortable with changing my mind. Don't get me wrong - I’m still a work in progress on this front!
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?
Bridget> Of course!! Nobody is perfect, and from these “failures” you learn and become better.
My failures have come in all shapes and sizes. Communication - shutting down someone’s great idea, jumping to a conclusion or making a decision before getting all the key info or taking the time to properly hash it out.
Mentorship - not making enough time or being proactive in supporting new and long term staff.
Accountability - in my efforts to delegate and empower, taking too far a step back and leaving someone hanging.
I try to be a self reflective person, and spend time evaluating myself day to day on how I can improve and be better. Every morning I remind myself to: listen, take a beat, support, be accountable, and have everyone’s back.
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?
Bridget> I don’t think transparency comes at the expense of care and consideration. You must always use care and consideration, and understand where transparency is required and where it could be onerous.
Leading with emotional sensitivity and a recognition that knowledge is power is where you find the balance. Your team needs the information and transparency in the way that will allow them to not only do their job well, but also allow them to grow and build in their role and careers. The emotional sensitivity comes into play where as a leader you should know the information they need to achieve this, and ensure access to it.
On the other hand, too much unnecessary info or candor can be a burden - sometimes that is a burden to bear only by those “in charge”.
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?
Bridget> A core piece of my vision of what makes great leaders is mentorship. Whether given or received. Rather than have one person who is my mentor, I look to all of my relationships with partners, colleagues, team members, clients, friends, and family as places of mentorship and learning. I listen to a lot of podcasts and read a lot of books to access learning and advice from the greats.
At Grayson we’ve built our culture around mentorship - within and without. Doors are always open and mentorship is built in as a key responsibility in our roles as managers and leaders.
LBB> In continually changing market circumstances, how do you cope with the responsibility of leading a team through difficult waters?
Bridget> I try to stay calm, cool and collected. LOL. Although I don’t always succeed, I do try!
My partners and I operate the business from a place of fiscal responsibility while pushing for growth and innovation. The key is to encourage everyone to be comfortable with change, and trying and failing.
Arming every member of the team with the ability to have an active role in that growth and innovation by valuing every single person’s participation in our creative output and operations leads to a greater sense of belonging, accountability, and integrity. All of which are essential to feeling somewhat in control at the individual level in the face of the constant uncertainty and challenge of our industry.
LBB> As a leader, what are some of the ways in which you’ve prioritised diversity and inclusion within your workforce?
Bridget> The promotion of diversity and inclusion at an organisational level and within our industry at large is a huge priority for me.
A few examples of this priority in action are: training and development opportunities for our staff, the hiring of staff who’s key responsibilities are to increase access to the opportunities at Grayson Music Group to a wider and more diverse group of creators, and we invest as a business in organisations whose mandates are to support and increase diversity, equity and inclusion in our industry.
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?
Bridget> It’s EVERYTHING! We work in a creative industry. If people are unhappy and uninspired then everything falls apart. Our culture is built around collaboration and community.
As I’d mentioned above, every member of the team is regarded as a key piece of the puzzle when it comes to our creative output and excellence. We do love to be together and work together in the same space - and for most of the team - this is a reality most days of the week.
We have teams spread across TO, NY, Nashville and LA - so prioritising social gatherings and regular check-ins is very important. Technology has made it a lot easier to keep the flow of communication no matter where you are.
LBB> What are the most useful resources you’ve found to help you along your leadership journey?
Bridget> There is so much amazing stuff out there to learn and grow in your role as a leader.
I mentioned podcasts, books, but honestly CONVERSATION is where it is at!
I think that you can learn to be a better leader, communicator, and mentor from the most surprising of places. It isn’t always the “How to be a better leader” podcast where you will get those nuggets of wisdom, it could be from a chat you have with someone at the dog park, a conversation you overheard on the subway, or a slogan you read spay painted on a wall.
Just be open and soak it all in.
Leaders come in all shapes and sizes and remember, when you look at the “boss” at your company - that is just their role, like any other within the organisation. While the role usually comes with great responsibility and a ton of stress, don’t let it go to your head.
At the end of the day we are all in this together and without each other we’ve got jack shit.
