Before you look for anyone, define the engagement. Five questions do that work: the challenge you are solving, the scope it requires, your organizational context, the function involved, and your timeline. Each answer narrows the field, and skipping one points the search in the wrong direction.
Most searches run the other way. A title gets written, a job description follows, and the field is set before anyone has asked what the work actually requires. These five questions sit at the centre of every client conversation we have, and they all come before the role.
What's the actual challenge?
Name the problem before the position. A vacant seat, a growth constraint, a transformation, and a capability you have never built in-house each call for a different engagement and a different person.
- A vacant seat is continuity. Someone left, the work carries on, and you need steady hands while you decide what comes next.
- A growth constraint is capacity. The business is outrunning what the current team can carry.
- A transformation is change. You are moving the organization from one state to another and want someone who has done it before.
- A missing capability is expertise that has never been on the payroll.
What scope does the work actually need?
Decide how much work there is and how long it lasts before you decide who does it. A defined project and ongoing part-time support are completely different engagements, and many organizations that arrive certain they need a full-time permanent hire are surprised by what this question reveals.
- A defined project has clear edges: a deliverable, a start, and an end.
- Ongoing part-time support is continuous and open-ended, a standing seat at reduced hours.
- A full-time permanent hire carries the most cost and commitment, and often more than the work in front of you actually requires.
What's your organizational context?
Your organization type shapes the match. A nonprofit and a privately held SME operate under different constraints, governance dynamics, and timelines, and the right person for one can be the wrong person for the other.
- A nonprofit answers to a board and often a funder, decisions move through committee, and the work carries a mission weight that shapes how a candidate fits.
- A privately held SME usually has a faster decision path and an owner whose priorities set the tone.
The same finance engagement looks different across the two, with different reporting expectations, different stakeholders, and different definitions of a good month. This is less a question you answer cold and more one experience has taught us to ask.
Which function needs attention?
Name the function precisely. The right finance professional and the right operations professional are different people with different instincts, and the same holds across marketing and IT.
Precision is what turns a vague ask into an actionable search:
“We need senior help” describes a feeling. “We need a finance professional who can stand up monthly reporting and cash-flow forecasting for a thirty-person company” describes a search.
The more exactly you can name the function and the work inside it, the faster a shortlist takes shape and the closer the first candidates land.
What's your timeline?
Set the timeline early, because urgency changes the approach. “We needed someone last Tuesday” and “we are planning sixty days out” are two different searches run at two different speeds.
- A planned timeline opens room for a wider search, more candidates, and time to weigh fit against a longer horizon.
- An urgent one rewards reach into an existing network of vetted, available professionals, and ours is built to deliver qualified candidates within ten business days.
Why define the engagement before naming the role?
Because starting with the title sets the search in motion before anyone has described the work. A role gets named, a job description follows, and the field narrows around assumptions these five questions would have tested first.
Across our more than 600 matches between Canadian organizations and the experienced professionals they needed, these questions have stayed at the centre of every conversation. They keep the search anchored to the work itself, so the right person becomes far easier to recognize when the candidates arrive.
SeasonedPros offers fast access to a network of business professionals ready to tackle complex challenges and drive organizational growth. Resource expertise faster with on demand talent for fractional, interim or project roles. Reach out today to learn how we can help:
