Negotiating Like a Pro: What Most People Miss When Talking About Compensation
Ep. 87 on the All Figured Out Podcast
with Jillian Climie of The Thoughtful Co.
Let’s be honest—negotiation can feel awkward. Especially when you’re a parent, returning from a leave, or walking into a new role and just grateful to have landed it. But what if asking for more didn’t have to feel so… uncomfortable?
In this week’s All Figured Out episode, I sat down with compensation strategist Jillian Climie, co-founder of The Thoughtful Co., to talk about how to navigate compensation like a pro. And spoiler alert: it’s not just about salary.
Jillian spent over a decade designing executive pay structures for major companies like Lululemon, so she knows exactly how offers are built—and how to advocate for more, confidently and respectfully.
What We Get Wrong About Negotiating
The biggest mistake Jillian sees? Waiting too long to talk about compensation—or approaching it like you’re doing something wrong.
Negotiating isn’t greedy. It’s strategic. It’s a value conversation, not a guilt trip.
Jillian’s approach is all about preparation and positioning. Instead of rambling your way through a raise request or accepting whatever offer shows up, she encourages people to:
Communicate early and clearly
Know who’s in front of you (and how they make decisions)
Focus on your value, not your personal needs
Understanding Pay Bands (and Those Giant Ranges)
Ever seen a job posting with a salary range from $80K to $160K and thought, “What the hell am I supposed to do with that?” You’re not alone.
Jillian breaks it down like this:
If you’re new to the role and will need support = lower end
If you’re fully functioning in the role = mid-range
If you’re already a leader in the space = higher end
Approach the conversation with clear evidence of where you fall—and ask questions if the band feels too broad or vague.
Coming Back from Parental Leave? You Can Negotiate
One of the most powerful parts of our conversation was when we talked about negotiating after taking time off to have or raise kids.
Jillian’s advice?
Don’t wait until you’re back and frustrated.
Start the conversation early (before your leave, if possible).
Document your accomplishments and scope changes.
Know that your value didn’t drop just because you were away.
And if you’re returning to find that your team is smaller, your workload is larger, and no one’s talking compensation? That’s your signal to initiate the conversation.
Whether you’re stepping into a new role, pushing for a raise, or returning from leave, this episode will shift the way you think about your worth at work.
About Jillian Climie:
Jillian Climie is the co-founder of The Thoughtful Co., where she helps women confidently negotiate their compensation and close the gender pay gap. With over a decade of experience in executive compensation and corporate governance, she’s worked with companies across North America and the UK to design pay structures that support equity and transparency.
Connect with Jillian via her website, Instagram, and LinkedIn
About Andrea Barr, host of All Figured Out
Andrea is a certified career and life coach for parents. Through her coaching, she supports parents in finding better work-life rhythms so they can continue to grow personally and professionally without sacrificing family time.
Connect with Andrea via Instagram here.
