Beyond salary, title, and start date — the questions that determine whether your next NFP, aged care, or education role will be a great chapter, or a regretful one.
When you're at offer stage, the temptation is to focus on the obvious: salary, title, start date, leave entitlements, hybrid arrangements. All important. But none of them tell you whether you'll thrive in the role.
After many years placing senior people into purpose-driven organisations, these are the six questions I'd ask if I were the candidate.
1. "What does success in this role look like at twelve months?"
This is the single most important question and almost nobody asks it properly.
You're listening for whether the answer is specific or vague. "We want someone to lead the People function effectively" tells you the organisation hasn't thought it through. "We want our turnover down from 22 percent to under 15 percent, we want the EBA renegotiated, and we want the leadership team's L&D capability uplifted" tells you they have.
If the answer is vague, ask a follow-up: "How will you and I know, in twelve months, whether this has gone well?" Be persistent. The answer matters.
2. "What's the hardest thing about this role that you haven't told me yet?"
Every senior role has something difficult about it. A difficult Board Director. An unresolved cultural issue. A function that's been under-resourced for years. A predecessor whose departure was messy.
Good organisations will answer this question honestly. They'd rather you go in eyes open than discover the difficulty at month three and disengage.
If the response is "there's nothing really, it's just a great role" — be sceptical. There's always something. The question is whether they trust you enough to name it.
3. "How does the Board actually engage with management?"
This is particularly important for CEO, executive, and senior leadership roles. Board-management dynamics make or break senior careers in the NFP sector.
What you're trying to understand:
- Is the Board strategic or operational in its focus?
- Does the Chair have a constructive working relationship with the CEO?
- Are individual Directors generally helpful, or do some create friction?
- How does the Board handle disagreement with management?
- Are Board papers used well, or is everything debated in real time in meetings?
Ask the CEO (or your future direct manager). Then, if you can, ask the Board Chair too. The two perspectives are revealing on their own, and any gap between them is more revealing still. For context on how Boards approach renewal, see Board succession in NFPs.
4. "What's the financial outlook for the organisation over the next two to three years?"
NFP, aged care, and education organisations are operating in tighter financial environments than they were five years ago. Funding cycles, regulatory cost pressures, donor base health, enrolment trends — all of these affect the organisation's stability and your ability to do the job.
Specifically ask:
- Is the organisation projecting surplus, balanced, or deficit operating positions?
- What's the reserves position relative to operating expenditure?
- Are there any major funding or revenue risks on the horizon?
- What's the appetite for investment in the function you're being recruited to lead?
Walking into a role where you'll be asked to drive change with no budget is a difficult experience. Better to know now. For broader sector salary and remuneration context, see our not-for-profit salary guide.
5. "Why is this role open?"
Ask this directly. The answer often matters more than candidates realise.
If the previous incumbent was promoted internally — that's usually a good sign. If they retired after a long tenure — fine, but ask about how the transition is being managed. If they left for another opportunity — fine, but probe whether anything in the role contributed.
If they were exited or resigned under stress — pay attention. That doesn't disqualify the role, but it raises questions about what changed (or didn't change) in the role that contributed to the situation.
In some cases, the role has been a revolving door. If you're the third Head of People in five years, there's a structural issue at play that won't be fixed by your appointment alone. Be honest with yourself about whether you can change it, or whether you'd just be the next casualty.
6. "What development and progression opportunities exist beyond this role?"
Not because you're about to move on. But because the answer reveals how the organisation thinks about people.
Organisations that take development seriously will have ready answers: external programs they sponsor, internal mentoring or coaching, exposure to Board work, sector engagement opportunities, secondments or stretch projects.
Organisations that don't will fumble for an answer or default to "we believe in promoting from within when we can."
Even if you're committed to staying in the role for many years, an organisation that invests in your growth is one you'll want to stay with. An organisation that doesn't is one you'll outgrow.
Bonus question for senior roles: "Can I speak to someone who used to work here?"
This is the question almost no candidate asks, and the one that often reveals the most.
A confident organisation will say yes and offer a couple of names. Even better, ask to speak to someone who left in the last 12 to 24 months. They'll have insights current employees can't or won't share.
If the organisation declines or gets defensive, that itself is information.
What the answers add up to
Individually, none of these questions is a deal-breaker. Collectively, they tell you whether the organisation:
- Has thought clearly about what they need from this role
- Trusts you enough to be honest
- Has functional governance
- Is in a financially sustainable position
- Has a healthy track record with this role
- Invests in its people
If most of the answers are clear and honest, you're probably joining a good organisation. If most of them are vague, defensive, or contradictory, you've just done yourself a significant favour by asking.
The recruiter's perspective
If you're working with a recruiter, they should be helping you ask these questions and helping the organisation answer them honestly. A good recruiter wants the placement to succeed long-term, which means both sides going in with eyes open.
If your recruiter is rushing you past these questions to closure — find another recruiter.
If you're considering whether NFP is the right sector for you in the first place, moving from corporate into not-for-profit covers the deeper sector-level questions worth thinking about first.
Sources
- Patterson Recruitment placement experience across senior NFP, aged care, and education roles
Considering an offer in purpose-driven work? Patterson Recruitment partners with senior candidates across not-for-profit, aged care, NDIS, and education. Browse current roles or book a confidential career conversation with Gab.
This article is current as at May 2026. Reflections drawn from Patterson Recruitment's senior placement experience.
