How I Went From Administrative Associate to VP People Without a Career Ladder (and the 5 Strategies That Made It Possible)

On this Page

Written by Kim Rohrer

Kim Rohrer is a veteran people leader, writer, speaker, and advisor with over 15 years of experience building human-centered cultures at high-growth companies. She is the founder of Patchwork Portfolio, author of the I Care Too Much newsletter, and co-host of the HR Confessions podcast. Today, Kim shapes the future of work through a portfolio of roles — from executive coaching to impactful communications to community architecture at Oyster® — and serves as a trusted advisor to forward-thinking HR teams.

Connect with Kim on LinkedIn.


I first got into HR because I wanted to help make the experience of work better. I liked knowing the rules (and where they were bendable), and I liked the feeling of creating a space that people could be proud to be a part of.

I didn’t set out to become a VP, though I eventually (politely) demanded my promotion to the seat I had earned at the executive table. I didn’t have a plan, or a career ladder, and I haven’t always grown laterally. There are so many ways to build a career, so many ways to be a leader … I wouldn’t try to prescribe one tried-and-true approach that always works.

If you’re earlier in your career and wondering how to chart your own path, I’d like to share a few tips based on advice I’ve gotten (and tweaked) and the lessons I’ve learned along the way.

1. Fall in love with the boring stuff (or find a partner who loves what you don’t).

It’s easy to get excited about culture decks, big announcements, and feel-good programs. But what moved the needle in my early career was operational excellence — payroll running on time, processes that worked, and systems that scaled.

I built a reputation as someone who could be trusted to get the basics right. That trust opened the door to bigger, more strategic projects.

As I grew (older, wiser, busier) I found I was more able to shift the “boring stuff” to other people on my team, who shockingly did not find it boring at all! I was able to hone in on my Genius Zones and spend more time doing the work that I loved and was uniquely good at. But when you’re just getting started, you kind of do have to be a hyperskilled generalist. Finding ways to work outside your wheelhouse is a power move.

2. Say yes before you feel ready. (But get thee to a mentor!)

Most of my biggest growth moments started with me saying “yes” to something that scared me (even when the thoughts inside my head were laughing nervously). 

  • Sure, I can make sure our paperwork is compliant. (I have no idea what compliance is!)
  • Absolutely, I can figure out how to do performance reviews. (I hate performance reviews!)
  • What if we had a Culture Book to send out to new hires? (I can figure out how to do that, right?)

Whether it was leading a new initiative, managing my first team, or taking on a project outside my comfort zone, I rarely felt 100% ready. But rather than sitting on the sidelines while watching other people fail upward, I harnessed the confidence of a mediocre white man and just did it anyway.

And I had a small circle of mentors on speed dial who I could call when I needed a gut check, a template, or reassurance. Some of those folks are still my closest colleagues today, and I still go to them when I need a little sanity (or vanity) check. Taking leaps, and asking questions, is the fastest way to prove you’re ready for a path to leadership.

3. Be unapologetically Human (but learn to speak Business).

Throughout my career, I’ve believed you don’t have to choose between being effective and being empathetic. People leaders are often expected to be the steady rock for everyone else, and it’s true — we don’t always have outlets within our organizations. But that doesn’t mean you can’t show vulnerability.

During uncertain times like layoffs, missed funding rounds, or tough product decisions, I have found that honest, human communication builds more trust than any polished script.

It’s OK to admit you don’t have all the answers as long as you commit to finding them.

One of the hardest things about approaching HR as an authentic, relatable human is that your other job in HR is supporting the business. If you want a seat at the executive table, you need to know how the business makes money, how functions intersect, and how talent strategy fuels growth. Early on, I prioritized building relationships with leaders across the company so that I could better understand their goals and constraints. 

When I advocate for new programs, it’s not just because I think they sound fun — I explain my thinking, share my research, consider the budget, determine how we’ll measure success, and ask for questions or hesitations early on instead of waiting until after I’ve done months of work. When I’m approached about adding headcount to a team, I don’t just say yes without thinking — I ask thoughtful questions about the org design strategy, management resources, and project prioritization.

Speaking their language made my work more accessible to them and helped me advocate for my priorities with credibility. 

You have to be able to walk the fine line between empathy for the people and understanding of the business. And you have to be able to show up authentically in both spaces.

4. Find your community (and keep learning, always).

HR can feel isolating, especially as you step into leadership. It’s not exactly professional for HR to air their grievances about people to coworkers (and let’s be honest, most of our gripes are about people), and most of the time, HR doesn’t have anyone to commiserate with at work. When I couldn’t find the community I needed, I cofounded the Organization Organizers (and more recently, Oyster’s People Builders, which I still work on). In later years, I joined a variety of professional networks and peer groups, attending happy hours and meetups and conferences to try to find my people. These relationships were lifelines when I needed advice or just someone to remind me I wasn’t alone in the hard moments.

Believe me when I say there are SO many more opportunities for connection now than there were when I was starting out! But you have to invest the time in finding the spaces that are right for you.  

What made me successful in my early career wasn’t the same skill set I needed as a Director or VP. I had to unlearn habits (like trying to do everything myself) and invest in new skills (like executive coaching and strategic planning), and I leaned on my community to help me develop and find resources to support my growth. I still do.

Leadership is about evolving, over and over again.

5. Remember why you started (and who you are).

It’s easy to get swept up in titles, scope, and the next promotion. But sometimes it’s helpful to reflect on why you’re even doing this at all — this work is ultimately about making work more sustainable, inclusive, and human. Remembering that can help you stay grounded when you’re overindexing on career trajectory.

If you’re in the early stages of your HR career, know that there’s no single path to leadership. Your story will look different from mine, and it should!

Stay curious, be a trusted collaborator, and lead with empathy. You might look up one day and realize you’ve become the kind of leader you once looked up to. ☺️

Communities

Reading & Resources

Offer Simple, Impactful Benefits

Skip the spreadsheets. Deliver the personalization employees want with stipends that are easy to use and easy to track.
Share the article
Share the article

On this Page

Offer Simple, Impactful Benefits

Skip the spreadsheets. Deliver the personalization employees want with stipends that are easy to use and easy to track.

Download the free Lifestyle Spending Accounts Guide

Download the free Lifestyle Spending Accounts Guide to learn why they’re the most low-maintenance

What’s next

Whether to invest in your team’s learning and development isn’t really a debate anymore. According to data from LinkedIn, 94% of employees say they’d stay...

Healthcare costs are rising at their fastest pace in over a decade, and GLP-1 medications are sitting at the center of that pressure. Employees want...

It’s 2026. Most companies aren’t only hiring within a commutable radius, and they haven’t been for years. While RTO mandates are certainly giving local hiring...

How I Went From Administrative Associate to VP People Without a Career Ladder (and the 5 Strategies That Made It Possible)

Schedule a demo

See how it works

Access the tour

Explore Professional Development Pro™ by Compt with an interactive tour and see how it can easily elevate your employee professional development program. 

Schedule a demo

Step confidently into the future of Professional Development management with Compt, where flexibility is limitless (or limited – the choice is yours!) and personalization is paramount.