Field Note · People, teams, and operating leverage
Build Context Before You Make the Next Hire
A vague job description describes the person a company hopes to find. A useful onboarding design describes the decisions, context, relationships, deliverables, and first proof that will let a real person succeed.
A thinking frame by Andrew Moss
The questions I get
Usually some version of these:
- What should we document before hiring an executive?
- How do we keep a new leader from spending 90 days discovering hidden expectations?
- What does good onboarding look like for a context-heavy role?
What a lot of people seem to think
Hire a strong person, hand them the mandate and a folder of documents, and assume a documented process will make the work scalable.
How I look at it
Great people still need a fair system. Make the decision-relevant context visible, define the first proof, and distinguish repeatable from scalable. The work is not scalable until someone other than the founder can run the full playbook, another person can check it, and the segment is coherent enough that the same method actually applies.
Why the decision matters
The cost is rarely confined to the line item.
If the sequence is wrong
The new hire spends the first months reverse-engineering unwritten expectations, gets judged against a moving target, and may recruit people into a role that was never made coherent.
If the sequence is right
The person can learn faster, earn trust through visible early proof, assemble the right team, and distinguish inherited constraints from choices they own.
How reversible is it?
Moderate, but a failed senior hire can cost a year of momentum, damage a team, and weaken confidence with customers, boards, and investors.
The short answer
Build the context, then prove the run-and-check system.
Name the decisions, outcomes, source material, relationships, authority, constraints, cadence, and first deliverables. Pilot the full playbook with the new leader, make the quality check explicit, and use founder rescues as evidence about what the system still has not taught or bounded.
A useful pictureA great player needs a field, a position, teammates, and a way to review the film.
The hero view of hiring imagines one executive arriving to fix the company. Durable performance comes from the person, the team, the context, the full playbook, and a feedback system that lets everyone improve.
Move fromA heroic mandate and document folder→Move towardA winnable, reviewable operating system
The order I would use
Take the right steps in the right order.
- 01
Name the blocked decisions
State what the company cannot decide, execute, or own well today.
- 02
Define early proof
Write observable 30-, 60-, and 90-day outcomes, including learning and relationship milestones.
- 03
Assemble decision-relevant context
Provide trusted data, history, customers, commitments, team dynamics, prior decisions, constraints, and open questions.
- 04
Clarify authority and handoffs
Separate decisions the hire owns, recommends, approves, influences, and escalates.
- 05
Pilot the full playbook
Test whether the same end-to-end method applies to the intended segment and whether someone else can run it.
- 06
Make the check explicit
Define who reviews consequential work, what good looks like, and how verified corrections improve the next cycle.
- 07
Count rescues and redesign
Use founder intervention and recurring exceptions to improve the role, playbook, segment, and onboarding system.
Questions worth answering
Before the next irreversible move:
- What must be materially better by day 90?
- Which context exists only in one person’s head?
- Can someone else run the full playbook without hidden founder labor?
- Who can check the result against an explicit standard?
- For which segment does the same end-to-end method genuinely work?
What not to do
Do not hire a biography into an undefined, uncheckable system.
Do not use a responsibility list as a substitute for priorities. Do not expect a great executive to read minds. Do not call documentation scalability when diagnosis, exceptions, review, and client trust still collapse back to the founder.
Keep the perspective
It takes a team and a system that helps the team improve.
Strong leaders can attract people and establish a way of working. The company creates the commercial leverage when it makes the field winnable, the context usable, the playbook transferable, and the correction loop visible.
Common follow-up questions
Should a startup document everything before hiring?
No. It should make the decision-relevant context visible: current facts, priorities, authority, dependencies, relationships, and early outcomes.
Does a great executive need to arrive with a team?
Not always. The useful signal is whether the person can attract, develop, and coordinate the capabilities the mission requires.