Ready to ask for that long-overdue promotion or pay rise but not sure how to start the conversation? Regina Stroombergen, Head Creative Tinker at Thinkerbell with extensive agency experience across Melbourne and London, offers practical strategies for building your case, while Dr Aileen Alegado, clinical psychologist and Director of Mindset Consulting, provides psychological insight into workplace dynamics. Together, they tackle the question of how to ask for a promotion or pay rise with confidence, especially when facing challenging workplace situations. Their advice? Prepare thoroughly, consider different perspectives, and remember that sometimes the best promotion comes from knowing when to move on.
Asking for a promotion or pay rise can feel like navigating a minefield—especially in the creative industries, where the path to progression is often anything but clear. Maybe you’ve been taking on more responsibility, consistently delivering strong work, or watching less experienced colleagues move ahead. At some point, the question bubbles up: Is it time to ask for more?
It’s a fair question—and one many creatives struggle with. How do you advocate for yourself without rocking the boat? How do you push for recognition while maintaining good relationships with your team? Whether you're dealing with gender bias, feeling undervalued, or just ready for the next step, learning to ask for what you’re worth is a key skill.
Helping unpack this topic are Regina Stroombergen, Head Creative Tinker at Thinkerbell (with years of agency experience across Melbourne and London), and Dr Aileen Alegado, registered clinical psychologist and Director of Mindset Consulting, who brings over 15 years of experience supporting professionals in high-pressure roles. Hosting the discussion is Andy Wright, Founder of Never Not Creative and CEO of Streamtime.
Regina’s advice? Start with a clear and considered approach:
"I think if I was in your position I would ask to have a meeting with your boss and make it clear um that you want to talk about sort of career progression salary um maybe culture culture of the business and that type of thing so there's no sort of surprises when you do catch up."
She also recommends backing up your ask with tangible contributions and clarity around your goals:
"Then I guess put your case together as to um why you deserve this pay raise and promotion um as well as sort of what you want to be doing so I want to be more client-facing I want you know more responsibility in this area and that type of thing and see how it goes."
In other words: set the tone early, come prepared, and communicate with clarity. These things build the foundation for a confident and constructive conversation.
Sometimes, what feels like a career block might be something else. Regina offers a helpful reality check:
"He might not be intentionally holding you back and trying to hide you it might just be that they're very um I guess assertive and maybe over the top but at the same time he might be doing that in which case if he says no you're not being more client-facing I'm not giving you a promotion or a pay raise then you might have to leave."
She’s not suggesting you settle, though. If your request is denied without a clear explanation, or you’re consistently undervalued, it may be time to explore other opportunities:
"You don't want to work somewhere that doesn't give you the sort of the value that you deserve."
Andy touches on a common concern—what happens if you do decide to leave, but there’s a non-compete clause in your contract?
"I think like if it is so specialised I think to be honest and this isn't legal advice and we can certainly direct you in the right place for legal advice but I think it was so specialised I'm not sure the non-competing Clause would even be defendable."
He follows up with practical advice:
"Often it's normally a case of look if I can't I think that the thing here is if you've had that conversation and you've set it up like Regina just said um and you've kind of Fairly talked about the situation you're in and that you both agree that it would be best if you know you moved on because you're not going to get the opportunities that you're looking for then actually you know it's perfectly fine then for you to go and find you know you you have a skill and you need to be able to continue that's how you make money I don't think it would be very defendable um to kind of try and enforce that."
Long story short: most non-compete clauses are hard to enforce, especially if they would stop you from using your skills altogether. Don’t let the fine print silence a fair career move.
If preparing for this kind of conversation is affecting your mental health or sense of self-worth, you’re not alone—and it’s okay to seek help. Asking for what you need at work can feel incredibly vulnerable, especially in environments where support isn’t always a given.
Our comprehensive help section includes 24/7 resources and mental health services that can support you through these moments. No shame, just support.
You don’t have to figure this all out solo. NNC Circles are small peer support groups where creatives gather monthly to talk through work-related challenges—including things like salary negotiations, career progression, and confidence at work.
These groups are private, facilitated, and designed to foster honest, non-competitive conversations. Sometimes hearing “I’ve been there too” makes all the difference.
Asking for a promotion or pay rise doesn’t make you difficult. It makes you proactive—and clear on your worth.
By preparing your case with evidence, setting the tone with open communication, and knowing your boundaries, you put yourself in the strongest position possible to have an honest conversation about your future. And if the answer is no, or the support just isn’t there? That clarity can be just as powerful as a yes.
You deserve to be seen, valued, and fairly compensated for your work. Whether that happens where you are now or somewhere new, the act of advocating for yourself is never wasted. It’s how you grow, professionally and personally.
Head Creative Tinker at Thinkerbell with Melbourne & London experience across sectors from auto to fashion. Founded MIA to champion mums in ads & co-founded The Aunties, supporting women in creativity.
Registered clinical psychologist & Director of Mindset Consulting with 15+ years’ experience supporting corporate professionals through therapy, coaching, wellness programmes & retreats.
Founder of Never Not Creative, CEO of Streamtime & co-chair of Mentally Healthy, driven to make the creative industry fairer & more human. Believes great work should never cost wellbeing.