The Right Role at the Right Level
Why Your Last Hire Didn't Work Out (And How to Get It Right Next Time)
The hire where I made the same mistake, AGAIN
A few months after starting Helia, I hired a Chief of Staff who looked great on paper.
They had design AND product AND brand experience — and they knew our market. These were all things I felt nervous about and weak on. I wanted someone who could teach me and lead the way. And I found them!!!
Then, a very short (and LONG!) five weeks later, they transitioned out.
While I was so busy finding someone to make me feel more confident and bring technical expertise to the table, I forgot to ask myself what I actually needed the person to do!!!!
The new hire wanted to ask strategic questions + be a thought partner — and was up to find and manage contractors. What Helia needed was a doer who could produce.
My first CoS took a month to write a creative brief. The second CoS — with no official design or product experience — had a detailed project plan by day three.
Both were "Chief of Staff" roles. Very different humans. Very different fits.
When a candidate's motivation — creating, executing, improving, supporting — aligns with where your organization is and what you need in the role, most other gaps can be bridged. Misaligned motivation can't be fixed, no matter how strong the resume.
And, while I wish this was the first time this ever happened (and REALLY hope it will be the last), I have, for years, made versions of these mistakes.
I hired too fast because we were overwhelmed. I’ve hired at the wrong level because I didn't stop to think it through (see above). I've brought on coordinators when I needed directors, directors when I needed doers, and once spent over a year looking for a "unicorn" that didn't exist.
Each mistake cost us time, money, and team morale.
When I sat down to think about why I kept getting this wrong and to (hopefully!) make sure it didn’t happen again, I created four questions to help you make sure you’re hiring for what you want AND what you need, before you even start drafting the job description!
The Right Role at the Right Level Process
After making this mistake again, I got serious about creating a better way. The steps below are built from my own reflections and the brilliance of Helia Collective members Sophia Zisook and Caroline Fitz-Roy. If you’re a “Just give me the template I’m ready to get started” kind of person (aka Helia’s COO Libby), here are the three core steps and the Right Role at the Right Level Template we created to walk you through them.
Start with the four magic questions
Match level to decision-making authority
Be realistic about what support you can actually provide
If you’re “Tell me the magic behind each step that makes this work” kind of person (aka Helia’s Founder Jess), read on for the good stuff!
Step 1: Start with four magic questions
Before you think about titles or levels, get clear on the work that needs doing:
What it reveals
Urgent fires to put out
Gaps in capacity or capability
Dependencies on specific people
Growth trajectory and future needs
Question
What keeps happening that shouldn't?
What's not happening that should?
What's working but feels fragile?
Where do we want to be in 1-3 years?
These four questions will tell you more than any job description template or competency structure. The key is having the discipline to start ALL new hire processes with them (note to self!!).
What This Looks Like in Practice: A Real Example
We recently worked with a growing nonprofit whose founder was stretched impossibly thin.
The founder is a visionary leader with strong business acumen and an exceptional talent for driving systems-level change. But her involvement in daily operations was limiting her ability to focus on what she's actually best at: refining their model, identifying strategic growth opportunities, and building external partnerships.
When we ran through the four questions with their team, here's what surfaced:
What keeps happening that shouldn't? The founder was getting pulled into day-to-day issues at their regional site — team questions, funder reporting, process gaps — because there was no dedicated local leadership.
What's not happening that should? Strategic expansion conversations kept getting pushed. Program workflows (especially data collection) were messy. The regional team was relying heavily on the founder plus some remote support and contractors.
What's working but feels fragile? The field staff were highly trusted in their communities and delivering strong results. But without local leadership, everything flowed through the founder.
Where do we want to be in 1-3 years? Expanding the model to new sites — which requires the founder to be freed up, not more entrenched.
The three scenarios we mapped out
Once we understood the needs, we sketched three different hiring approaches:
Scenario 1: Three dedicated roles
Manager of Operations (day-to-day admin, finance, HR, compliance)
Chief of Staff/Deputy Director (founder's right-hand for strategy, fundraising, internal leadership)
Site Director (local team management, program oversight, on-the-ground accountability)
Pros: Strong coverage. Frees the founder to focus on expansion. Each person can specialize.
Cons: Highest cost. Requires coordination across three leaders.
Scenario 2: Combined roles
Director of Operations & Strategy (owns both internal ops AND supports the founder on strategy/fundraising)
Site Director (local leadership and program integrity)
Pros: Lower cost. Simpler reporting. Still provides local leadership.
Cons: Hard to find someone great at both ops AND strategy. Role may become too broad.
Scenario 3: Lean + outsourced
Part-time operations consultant or outsourced services (finance, HR, admin on contract)
Chief of Staff (full-time or part-time strategic support)
Site Director (local leadership)
Pros: Lowest cost. Flexible. Can scale up later.
Cons: Less control over outsourced functions. Gaps between part-time coverage.
What they decided
They went with a version of Scenario 2 — with a plan to revisit in 12 months as they grew. The "right" answer wasn't permanent; it was right for this moment.
My daughter Nat (16!) at an Angel City football game! Nat has sat in on a LOT of my interviews over the years (pandemic, driving to/from school, etc.) - and is now a VERY savvy interviewer.
The point isn't to copy their structure. It's to see how breaking down the four questions — and then mapping scenarios with real tradeoffs — helps you figure out what's actually right for YOUR organization right now.
Trying to figure out what structure makes sense before you start recruiting?
Nina Jacinto helps leaders think through what they actually need from their team structure — the kind of diagnostic work that clarifies whether you need one role or three. → Email Nina at nininarjacinto@gmail.com with "Helia Connection" in the subject line.
Step 2: Match level to decision-making authority
A common mistake is hiring at too senior a level because we want to signal importance, then not actually giving that person the authority that comes with the title.
Gut-check: Which of these sounds like what you need?
A) "I need someone to execute tasks with clear direction from me." → You're probably looking at Coordinator/Associate level. Make sure you have time to train and oversee them.
B) "I need someone to own a function and make day-to-day decisions, but I'll still be involved in bigger calls." → You're probably looking at Manager level. Make sure you can give them enough context and autonomy to own the day to day.
C) "I need someone to run this area independently — I want to hand it off and trust them to figure it out." → You're probably looking at Director level. Make sure you're actually ready to give them that authority (and the salary that comes with it).
I know - a random dog photo!!! And we got REALLY clear on why for the second pup, needed to play wildly well our first (there’s nothing that can tire a dog out like another dog and we couldn't keep up) AND we wanted a dog that would snuggle and be a little more loving than our I want to be right next to you and will protect you in all things but please only touch me when I want to be touched. The specifics shifted (size, age, etc.) but the why our family needed a second pup were a YES the whole way through!
The harder questions
Be honest with yourself:
1) Will this person need to make significant decisions without checking with you first?
2) Will they need to build systems or processes from scratch?
3) Will they represent the org externally in important ways?
4) Does the work require navigating a lot of ambiguity?
5) Will they manage other people? If so, how many?
And critically — what can YOU actually provide?
1) How much time do you have for training and oversight?
2) How much direction can you give day-to-day?
3) Are you ready to let them make decisions you might disagree with?
Step 3: Be realistic about what you can support
Sophia Zisook, who helps organizations build equitable hiring processes, is refreshingly direct about this: "Too many organizations hire junior people because they can't afford senior folks, then expect them to perform without the support they need."
Every level of hire requires different support from you:
Coordinators need clear direction, training, and regular oversight
Managers need context, connections, and some autonomy
Directors need authority, information, and trust
VPs/C-Suite need partnership and latitude
If you don't have time to train someone, don't hire at the coordinator level. If you're not ready to share decision-making, don't hire at the director level.
At one stage at Think of Us, I set a guideline that everyone we hired had to have at least 2+ years of work experience AND had done at least a version of the job we were hiring for before. We were running SO thin and growing SO fast that we didn’t have the time to dedicate to training and support. Every time we hired someone who needed foundational training in “how to’s” versus role-specific work, we weren’t showing up for them and we were setting everyone up to fail. It wasn’t the most popular choice given what we valued hiring individuals with lived experience AND, when we were honest about our capacity and our priority to put our work and impact first, it was an obvious decision.
Two level-specific mistakes I've made
Hiring too senior: I once brought on a Director of Development with incredible fundraising experience. Six months in, they were frustrated because I wasn't ready to have them independently manage our largest donor relationships. The title suggested authority I wasn't willing to give. We should have hired a Development Manager instead.
Hiring too junior: I once hired a brilliant but junior operations associate because the salary fit our budget. By week three, I realized I didn't have time to provide the training and oversight they needed. The budget worked, but I couldn't actually support someone at that level.
If you're wrestling with this exact tradeoff — budget vs. support capacity — that's a great thing to talk through with someone outside your org. [Book 30 minutes with Sophia Zisook](CALENDAR LINK) and she’ll help you think it through.
What each level might actually looks like
Here's a snapshot of common operations and executive support roles — what each level does, what they WON'T do, and typical salary ranges:
→ See the full Common Roles Reference Guide for Development, Program, Sales, and Product roles with the same breakdown.
A note on salaries: These are national averages for the social sector based on 2025 numbers. Adjust 20-40% higher for major cities (NYC, SF), 10-20% lower for rural areas. Org size and funding model matter too, and the dollar amounts will change each year. Take this as directional versus “it,” of course!
When to do this yourself vs. bring someone in
Everything I've shared here? You can do it. If you're willing to slow down and answer the four questions honestly before writing a job description, you'll avoid most of the expensive mistakes.
You might want outside help if:
Everyone has a different opinion about what level to hire — and you need someone outside the politics to facilitate alignment
You're building your first leadership team — and want to get the structure right before you start recruiting
The role is strategic and high-stakes — and you want a thought partner on the design before you invest in the search
You keep making the same hiring mistakes — and need help seeing the pattern
Signs you might be making the wrong choice
Before you post that job description, run through this checklist:
🚩 You might be hiring too junior if:
You're hoping they'll "grow into" responsibilities you need covered NOW
You're planning to give them decision-making authority but hiring at coordinator level to save money
You find yourself thinking "they can figure it out" for complex work
The role requires building something new, not executing something established
🚩 You might be hiring too senior if:
You're not actually ready to give them the authority that comes with the title
Most of the day-to-day work is execution, not strategy
You're hiring a Director but planning to approve all their decisions
The real need is for hands-on work, but you want to signal importance
If you need a recruiting partner
Caroline + Jess chatting about recruiting magic for her Helia article!
Caroline Fitz-Roy at Fitzroy and Associates partners with social sector organizations on executive and leadership searches — from role design through final offer. Her approach is grounded in research and listening: she's not just activating her rolodex, she's building a custom market map for YOUR specific need.
She's a good fit if:
You're hiring for a senior role and want a recruiting partner who gets the social sector
You've been searching for months and aren't finding the right candidates
You want someone to manage the process so you can focus on running your organization
You need help understanding what the market actually looks like for this role
Ready to talk? → Email Caroline at caroline@fitzroyandassociates.com with "Helia Connection" in the subject line
Not sure who's the right fit? Book 30 minutes with Helia and we'll help you figure out who in our Collective might be.
What to take with you
Start here (free)
→ Right Role at the Right Level Template — Everything you just read in a neat template you can share or use with team members.
→ Common Roles Reference Guide — The full breakdown across five functions (Ops, Development, Program, Sales, Product) with salary ranges and what each level will/won't do.
Recommended Reading:
Hiring with Heart and Strategy — Sophia's full process for running a hiring process that's systematic, equitable, and actually finds the right person
Curiosity Over Persuasion — Caroline's approach to recruiting that's grounded in research and listening
When templates aren't enough
These tools will help you get started. And when the hires are critical OR you can’t quite get it right, we’ve got you!!!! Book 30 minutes with Helia and we'll help you figure out who in our Collective might be.
Questions to sit with
Think about your last hire that didn't work out:
Was it the wrong level, the wrong fit, or the wrong moment?
What would you do differently knowing what you know now?
For your next hire:
If this person succeeds wildly, what would be different in one year?
What kind of support can you realistically provide?
Are you hiring for where you are now, where you want to be in a year, or both?
Have you answered the four questions honestly — or are you jumping straight to the job description?
HELIA BONUS: The Why Interview
The Most Important Interview You’ll Do
This is my secret weapon — and honestly, probably the MOST important interview you can have (and one of my favorites!!!!).
Once you've designed the right role at the right level, you need to check whether candidates actually want to do THAT job — not just any job with that title. The Why Interview surfaces that. It comes VERY early (first or second round) and the technique is simple: ask them to introduce themselves and what sparked them to say yes to this conversation — then really listen. What do they lead with? Where does their energy shift? What do they skip over?
What you’re listening for is someone who wants to do the exact job you’re hiring for, and whose WHY for wanting to do the work matches your organization’s WHY. Skills can be taught; WHY cannot. Every time I've hired for skills over the why, it's been a mistake. Every. Single. Time.
→ Get the full Why Interview Template for the conversation guide and reflection prompts.
Real examples of hiring for why, not skills:
Target store GM → school food Sales Manager (Lupe!!!). No sales or school experience. But she loved figuring things out, thrived in fast-paced environments, understood data, and knew how to make things happen with ops. That's what we needed.
National funder's External Affairs lead → research and legislative work. They loved fitting all the pieces together and understood power dynamics.
Fashion industry PM → nonprofit communications. They knew how to make a million pieces fit together and brought a visual eye we didn't have.
Two Customer Success hires: One had no experience and didn't love people(!) but LOVED building systems. The other had tons of background and instant rapport but wanted things handed to them. We needed someone who wanted to build to make things work for people, not just connect. The hire with NO experience who didn’t like people = HUGE success. The other person left within a month.
Match the why — and everything else works out!
Want help building an interview process that screens for what actually matters — not just credentials? Sophia Zisook designs equitable hiring processes from job description through offer. → Email sophia@negotiatewithsophia.com with "Helia Connection" in the subject line.
About the Contributor
Jess Skylar is the founder of The Helia Collective. She's spent twenty years scaling mission-driven organizations — growing Revolution Foods from $14M to $170M and co-building Think of Us into a national leader. Along the way, she's hired hundreds of folks. Some became her favorite humans to work with. Others taught her what not to do next time.
-> Want to work with Jess and our team? Book 30 minutes with Helia and we'll help you figure out who in our Collective might be.
More where this came from
This article is part of Helia's hiring series. If getting the level right isn't your stuck point, you might find these helpful:
Finding Your People — How to identify who actually thrives in your culture
Hiring with Heart and Strategy — Sophia's full process from job description to offer
See who's in the Collective or tell us what you're working on and we'll point you toward the right person.
This article comes from years of hiring (and mis-hiring) at Revolution Foods, Think of Us, and beyond — and from conversations with the recruiters and people ops folks who've taught me what I was missing.
As always, take what's helpful, leave what's not, and make it your own.
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