Long Story Short
Your hires aren’t working out because there’s a mismatch between what your org really needs and the role/level you hired for. Don’t have time to read this whole article? The Right Role Right Level Template in our Right Hire Toolkit can get you started.
Jump to How!
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 costs us time, money, and team morale.
The Key Takeaway
When I sat down to think about why I kept getting this wrong and to (hopefully!) make sure it didn’t happen again, I realized the problem was that I was starting with the job description. What I needed to start with instead, was getting clear on what the organization needs in this moment and what it can provide to a new hire.
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 we built you a Right Hire Toolkit we created to walk you through them.
- Step 1: Start with the four magic questions
- Step 2: Match level to decision-making authority
- Step 3: 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!
How These Steps Work
Step 1: Start with four magic questions
Before you think about titles or levels, get clear on the work that needs doing:
| Question | What it reveals |
| What keeps happening that shouldn’t? | Urgent fires to put out |
| What’s not happening that should? | Gaps in capacity or capability |
| What’s working but feels fragile? | Dependencies on specific people |
| Where do we want to be in 1-3 years? | Growth trajectory and future needs |
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.
What I needed to start with instead was getting clear on what the organization needs in this moment and what it can provide to a new hire.
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.
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.
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).
The harder questions
Be honest with yourself:
| Question | Your answer |
Will this person need to make significant decisions without checking with you first? | Yes / No / Sometimes |
| Will they need to build systems or processes from scratch? | Yes / No |
| Will they represent the org externally in important ways? | Yes / No |
| Does the work require navigating a lot of ambiguity? | Yes / No |
| Will they manage other people? If so, how many? | Yes / No |
| And critically — what can YOU actually provide? | Yes / No |
| Question | Your answer |
| How much time do you have for training and oversight? | A lot / Some / Very little |
| How much direction can you give day-to-day? | Detailed / General / Minimal |
| Are you ready to let them make decisions you might disagree with? | Yes / No / Depends |
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.
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.
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.
What each level 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:
Operations + Executive Support
| Role | Quick Look | What they will NOT do | Salary Range |
| Executive Assistant | Keeping the trains running — calendar, travel, basic coordination | Strategic leadership or program ownership | $55-85K |
| Operations Manager | Systems and processes — team coordination, process improvement, vendor relationships | Executive leadership or strategic planning | $70-100K |
| Chief of Staff | Extension of executive capacity — strategic projects, cross-team coordination, board support | Pure administrative work or dedicated program ownership | $90-140K |
| Deputy Director | Organizational leadership — team management, strategic planning, program + ops oversight | Primarily administrative or project-based work | $130K+ |
See the full Common Roles Reference Guide in our Right Hire Toolkit 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!
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
THE WHY INTERVIEW: The most important interview you’ll ever 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. 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!
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
If You Want Help
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
Connect with Caroline!
What to take with you
- Right Role Right Level Template: A step-by-step template for working through the four magic questions, matching level to decision-making authority, and reality-checking whether you can actually support the hire you’re considering.
- Finding Your People Worksheet: A structured reflection to help you hire for your real culture—not the one in your values statement.
- Common Roles Reference Guide: A reference table breaking down common roles across five functions (ops, development, sales, program, product) — with quick descriptions, sample responsibilities, what each level won’t do, and salary ranges.
- The Why Interview Template: A guided conversation framework for uncovering whether a candidate actually wants to do the specific job you’re hiring for — not just any job with that title.
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
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?
Not sure Caroline‘s the right fit? Talk to Helia directly!
About Jess
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.
