01comp
Compensation Structure
The total construction of the package, not the base. Bonus structure, equity vehicle, vesting, refresh, severance, change of control, and what is and is not guaranteed in writing.
Questions- 01What is the mix of base, target bonus, sign-on, and equity over a full vesting cycle?
- 02What triggers full or accelerated vesting and what does the severance look like if the role ends in year one or year two?
- 03What is the bonus formula, who decides it, and what has it actually paid in the last three cycles?
- 04Is the equity refresh policy in writing or implied?
- 05What does the package look like in a down year for the business, not a good year?
Weak signalA strong headline number with vague bonus mechanics, no refresh, no severance, and a verbal promise that the rest will get figured out later.
Strong signalThe structure pays you to deliver, protects you if the seat goes sideways, and is documented in the offer letter.
02scope
Scope and Mandate
The actual size and shape of the seat. Org size, P&L, decision rights, budget authority, and a written, current charter for what the role exists to do in the first twelve months.
Questions- 01What does the org look like on day one, headcount, leaders, and budget?
- 02What are the three to five outcomes this role is being hired to deliver in the first twelve months?
- 03What decisions can you make alone, what requires alignment, and what requires approval?
- 04What did the predecessor own that has quietly been pulled out of the role?
- 05Where does the scope grow over the next twenty four months and where is it expected to shrink?
Weak signalBig title, fuzzy mandate, and a scope that is described differently by the hiring manager, the recruiter, and the peer interviews.
Strong signalA clear, current charter with named outcomes, named decision rights, and a budget that matches the mandate.
03altitude
Altitude
Where the seat actually sits in the org. Distance to the CEO, board exposure, and the level of decisions you are in the room for versus the level you are notified about.
Questions- 01How many layers sit between you and the CEO and has that distance changed recently?
- 02Which forums are you a standing member of and which are you a guest in?
- 03What board exposure does the role carry and how often?
- 04Are you part of the team that sets strategy or the team that executes it?
- 05Who is your peer set on the org chart and is that the peer set you want for the next move?
Weak signalThe title implies altitude the seat does not actually have, and the real decisions happen in a forum you are not part of.
Strong signalYou are in the rooms where the decisions are made, with a peer set that signals the level you want to be at next.
04sponsorship
Sponsorship
The political weight of the person who hired you. Their tenure, capital, and whether your success is tied to a sponsor who is themselves stable in the seat.
Questions- 01How long has your hiring manager been in role and how long are they likely to stay?
- 02What is their standing with the CEO and the board today, not last year?
- 03Are there other senior leaders who advocated for this hire or is it a single sponsor?
- 04If your sponsor left in six months, does the role still exist with the same shape?
- 05What happens to the mandate if leadership above your sponsor changes?
Weak signalA single champion brought you in, recently arrived themselves, and the rest of the leadership is neutral or quiet.
Strong signalMultiple senior stakeholders are invested in the hire, and the role survives a change in your direct sponsor.
05health
Org Health
The condition of the business and the team you are inheriting. Growth, runway, recent turnover at your level, and whether the seat is open because of expansion or because of pain.
Questions- 01Why is this seat open and what happened to the last person in it?
- 02What has turnover looked like at your level and one level below in the last twenty four months?
- 03What is the financial trajectory of the business and how long is the runway?
- 04What is the team you are inheriting and what shape is it in?
- 05What does the rest of the leadership team say about the company when they think no one is listening?
Weak signalRecent turnover at your level, a team in visible distress, and a story about the business that requires you to squint.
Strong signalA healthy business, a stable leadership team, and a team you are inheriting that is broadly intact and broadly competent.
06trajectory
Trajectory
What this role positions you for next. The market signal of the title and company, and the kind of seats this seat tends to lead to inside the company and outside of it.
Questions- 01What does this title and this company say about you in the market in two years?
- 02Where have the last three people in this seat gone next, inside the company or outside?
- 03Does this role open the door to the next level you want, or does it cement you at this one?
- 04What new relationships, exposure, or experience does this seat give you that you do not currently have?
- 05If you wanted to leave in three years, what would the next role look like from this seat?
Weak signalA strong title with no visible exit, no recent precedent, and a story that the next move will appear when you get there.
Strong signalThe seat is a recognizable launchpad, with recent precedent of people moving from it to the level you want next.
07cost
Personal Cost
What the role asks of your life outside the role. Relocation, travel, time, energy, family impact, and the opportunity cost of the work you will not do because this work is in front of you.
Questions- 01What does the role require of your time and attention in a normal week and in a hard week?
- 02What relocation, travel, or geography does it require and for how long?
- 03What does the role cost your family, your health, and the relationships outside work that you protect?
- 04What are you walking away from that is not on the offer letter, in equity, projects, or proximity?
- 05If the role disappeared in twelve months, would the personal cost still have been worth it?
Weak signalThe upside is loud and the costs are vague, deferred, or rationalized in a sentence that starts with 'it will only be for a while'.
Strong signalThe cost is visible, named, and acceptable to you and to the people the cost will land on.