Hiring and headcount
Do we need another person, and what kind? Whether to add someone, when, at what level and on what basis — and how to tell a durable need from a busy quarter before you commit to a salary.
Free · usually only a few minutes · no account
Hiring is the most visible answer to a team under pressure and usually the first one that comes to mind. It is also the slowest, the most expensive and the hardest to undo. That does not make it wrong, and plenty of these questions end with "yes, hire" — it makes it worth checking.
The questions in this family all turn on the same two things: how durable the need is, and what a new person would actually own. A need that has lasted a year and is growing is a different proposition from a launch that finishes in March, and a role you can describe in a sentence is a different proposition from one you cannot.
The expensive mistake here is rarely hiring the wrong person. It is hiring before anyone has decided what the role owns, and discovering afterwards that the thing you were short of was not a person.
Worth settling before any of these
- How long the pressure has been there, and whether it is growing, steady or a peak that will pass.
- What the new person would own — outcomes, not a job title.
- Whether the salary is genuinely fundable, or fundable only at a stretch.
- Whether anyone already in the team could grow into it with support.
The questions in this family
Should I hire another person?
Sometimes. Whether a hire is the proportionate answer depends on how durable the need is, whether anyone owns the work today, and what a new person would actually add.
Read the answerWe have a skills gap. Should I train, hire or bring someone in?
It depends on how long you need the skill, how soon, and whether anyone in the team is close to it. Each answer points at a different route.
Read the answerShould I hire another salesperson?
Only once you know whether the constraint is demand, conversion or capacity. Another salesperson adds capacity; it does not on its own create a pipeline or fix a way of selling that is not working.
Read the answerHow do I know if my team needs more headcount?
Look for a gap that is durable, growing and visible in outcomes rather than in how busy people feel. Missed commitments, work that has quietly stopped and an inability to absorb anything new are better evidence than hours.
Read the answerShould I hire a graduate?
A graduate fits where the work is learnable, somebody has time to teach, and the capability is needed for years rather than months. You are buying potential and paying for it in supervision rather than salary.
Read the answerWhat should my next hire be?
Start from the constraint rather than the wish list. The right next hire is the one that releases the most work or removes the largest risk — which is often not the role that feels most overdue.
Read the answerShould I hire now or wait?
Timing is a real decision, not a delay. Hire now when the need is durable and fundable and the role is defined; wait when any of those is still a guess.
Read the answerShould I hire full-time or contract?
Contract buys speed and information; permanent buys accumulation. The right answer depends on how durable the need is and whether you need the knowledge to stay.
Read the answerShould I replace someone who left?
A departure is the cheapest chance you will get to ask whether the role should exist in the shape it did. Replacing like for like is a decision, not a default.
Read the answerShould I hire a junior or a senior?
Seniority is a decision about how much definition the role comes with. A senior defines the work; a junior needs it defined, and someone with time to do that.
Read the answerCan I afford to hire right now?
Affordability is not the salary. It is the salary plus recruitment, onboarding, management time and the months before the person is productive — against what happens if you do not.
Read the answerWhen should a startup hire its first engineer?
When there is durable technical work, someone who can judge technical quality, and enough definition for an engineer to own something rather than wait to be told.
Read the answer
Nearby decisions
These families overlap with this one often enough to be worth a look — most team decisions turn out to belong to more than one of them.