Your Career Doesn't Have to Follow a Straight Line:
Six Lessons for Strategic Operators
Career growth looks pretty straightforward on paper: gain experience, take on more responsibility, earn the next title, keep moving.
Except... that's rarely how it actually works.
Maybe you're trying to break into a new industry. Maybe you're doing Chief of Staff-level work without the Chief of Staff title. Maybe you really like your company, but you're starting to realize there may not be anywhere else for you to grow. Or maybe you're staring at a job posting with hundreds of applicants and wondering how you're possibly supposed to stand out.
These were some of the very real career challenges our students and grads brought to a recent Nova Weekly Coaching & Community session.
And because our community is full of people who have hired, been hired, changed careers, supported executives, built teams, and navigated their own winding career paths, the advice started flying.
We don’t gatekeep. Here are six takeaways worth sharing.
#1. Be Careful About the Story You're Telling Yourself About Your Experience
One of our students was talking about moving from agriculture and startup environments into a more traditional Executive Assistant role when she described her varied background as part of "the problem."
We stopped right there.
Because it wasn't the problem.
When you're making a career change, it's incredibly easy to start explaining your background by pointing out everything that doesn't fit.
I don't come from this industry.
I haven't technically had that title.
My experience is kind of all over the place.
But take another look.
Maybe working in a startup taught you to context switch constantly, operate without a playbook, figure things out quickly, and fill gaps before anyone had time to assign them.
Maybe working across completely different environments made you a better project manager, communicator, or dot connector.
The company you're interviewing with probably doesn't need another person who knows exactly what everyone else in the room knows. They may need the person who brings the skills the rest of the room doesn't have.
So when you catch yourself saying, "The problem with my experience is..." challenge yourself to finish a different sentence:
"The advantage of my experience is..."
That's the story you want ready before you walk into the interview.
#2. Don't Just Apply for Jobs. Get Closer to Where the Jobs Are.
One of our favorite pieces of advice from the conversation came from a Nova community member who compared networking to finding a "pocket listing" in real estate.
Think about it.
People inside a company often know well before a job is posted that an executive is coming in, someone is leaving, a team is growing, or a new position is probably going to be needed.
And strong EA and administrative communities in particular are incredibly connected. They know each other. They recommend each other. They know what's happening inside their organizations.
That's a very different position than being applicant #437 after a job hits LinkedIn.
So yes, apply for the job.
But also find the communities where people doing the work you want to do are spending their time. Talk to EAs. Talk to Chiefs of Staff. Talk to people in industries you're curious about.
And don't lead with, "Can you help me get a job?"
Ask them about their work. What do they love? What's challenging? What is changing inside their industry? What skills matter most?
You're building relationships.
Then someday, when someone says, "We're probably going to need someone..." there's a chance your name comes up before the job posting does.
#3. Get Your Interview Reps In
You can prepare for an interview all day long.
At some point, you need reps.
Take interviews. Have networking conversations. Practice explaining what you do. Get really good at answering the deceptively simple question:
"Tell me about yourself."
You should be able to explain who you are, what you're great at, and what you're looking for without needing five minutes to get there.
And here's one place where AI can actually be a fantastic practice partner.
Give it the job description. Ask it to act like the hiring manager. Have it ask you questions one at a time. Answer them out loud and ask it to evaluate how clearly you're communicating your examples using a framework like STAR.
Do it again.
And again.
It's a whole lot easier to discover that your favorite example takes seven minutes to explain when you're talking to AI than when you're halfway through the interview for the job you really want.
#4. Use AI to Prepare, But Make it Sound Like You
Speaking of AI...
Use it.
Use it to practice interviews. Use it to brainstorm. Use it to help you think through how your experience connects to a job description.
But when it comes to the actual application? Be careful.
Hiring managers are reading hundreds of applications, and you would be amazed how quickly AI-generated responses start sounding exactly the same.
Same opening.
Same perfectly constructed bullets.
Same words.
Same tone.
If 300 people are using the same tools to answer the same question, sounding polished isn't necessarily what makes you memorable.
You do.
Tell the story only you can tell. Include the detail another applicant couldn't copy. Let your personality come through.
AI should help you communicate your experience—not flatten your experience until you sound like everyone else.
#5. Ask What They're Actually Looking For
Job descriptions tell you a lot.
They don't tell you everything.
So ask.
Toward the end of an interview, try something like:
"Is there anything you're looking for in the ideal candidate that I wouldn't necessarily know from reading the job description?"
Or:
"If you could choose one quality that would make someone really successful in this role, what would it be?"
You might be surprised by how candid the answer is.
And now you have useful information.
Maybe they name something that happens to be one of your greatest strengths. Great, tell them why.
Maybe they name something that makes you realize this role isn't actually what you're looking for.
Also great.
Remember: you're not just trying to convince someone to hire you. You're trying to figure out whether you should want the job, too.
#6. If You Can't Move Up, Look Around
Another student brought us a completely different career challenge.
She loves her company. She's grown tremendously in her role. She's taken on more strategic responsibilities and gained exposure to leadership. She's doing work that feels increasingly aligned with where she wants to go.
Her goal is Chief of Staff.
The problem? Her company has essentially told her “that title isn't an option here.”
When you're ambitious and you've been working toward something, that's frustrating.
But once you know the wall is there, you have choices.
You can keep staring at it. Or you can start looking for another door.
What other departments exist inside the company? Who is doing strategic work you'd like to learn? Could you raise your hand for a project? Could you help another team solve a problem? Could you build experience in operations, strategy, programs, or another function that moves you closer to the work you ultimately want to do?
Maybe the path isn't:
Executive Assistant → Chief of Staff
Maybe it's:
Executive Assistant → Strategic Operations → Chief of Staff
Sometimes the best next move isn't up. It's over.
And if you've explored the other doors and there truly isn't anywhere else to go? You may have learned something important: you've outgrown the room you're in.
That doesn't make the experience you had there any less valuable. It just means it may have done exactly what it was supposed to do: prepared you for what's next.
One Last Reminder: Your Career Is Allowed to Look a Little Messy
There isn't one perfect path into strategic operations or the Chief of Staff role.
That's something we see every day at Nova.
Our community comes from Executive Assistant roles, operations, project management, communications, HR, startups, large corporations, nonprofits, and plenty of careers that don't fit neatly into a single box.
What matters is learning to recognize the skills you've built, talk about them with confidence, and keep moving toward work that gives you the opportunity to use them.
So get curious.
Talk to people.
Get your interview reps in.
Raise your hand for the project.
Apply for something that feels like a stretch.
And the next time you hear yourself explaining why your background is the problem, stop and ask:
What if it's actually the advantage?
Join the Conversation
There’s a lot you can learn from a course. There’s also a lot you learn by getting in a room with other people doing the work.
That’s why Weekly Coaching & Community is part of the Nova student experience. Every week, students and grads can show up with a question, talk through something they’re navigating, share what’s worked for them, or simply listen and learn from the conversation.
Weekly Coaching & Community is available to Nova students and graduates as part of their lifetime access to the Nova Chief of Staff Certification and community.
Learn more about becoming a Nova student → https://www.novachiefofstaff.com/certification