Questions to ask managers and senior leaders

What does the first ninety days look like, and what would tell you it went well?

A director with a specific answer has thought about the role; one who says to come in and see is offering you the job of inventing it. Both are workable, but only one is what most people expect.

From: Questions to Ask Director

When everything on the list looks worth funding, how do you choose?

Listen for an actual bar: a payback period, a hurdle rate, a protected strategic carve-out. If there is no bar, only a discussion, capital tends to follow whoever argues hardest in the room.

From: Questions to Ask a CFO

What are you personally spending most of your time on this quarter?

Calendars reveal priorities that strategy decks hide. If their time is going somewhere the company narrative never mentions, that gap is usually where the real problem or the real bet lives.

From: Questions to Ask Corporate Leaders

How much can I discount before I need to come to you?

A clear number means you can negotiate in the room. If the answer is always check with me, expect deals to stall at the end of the quarter through no fault of your own, and plan your close dates accordingly.

From: Questions to Ask a Sales Manager

What tells you a team is in trouble before the numbers show it?

Early-warning signals are craft knowledge: attrition in one team, silence in meetings, small commitments slipping. Few leaders have written these down and most enjoy explaining them.

From: Questions to Ask Senior Executives

How do you keep the numbers you receive from being managed for your benefit?

Anyone senior gets a filtered view, and good operators build routes around it: skip-levels, sitting in on calls, reading raw tickets, unannounced visits. If they claim their reporting is simply accurate, they are describing a company they have not tested.

From: Questions to Ask a COO