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Twelve red flags in a leadership offer, and the question to ask about each

A due-diligence checklist for anyone weighing a senior role in an organisation that is struggling.

In short

  • Most glass cliff risks are visible before you sign, if you ask the right questions.
  • The biggest warning signs are about information, authority, resources, time and support.
  • Each red flag below comes with one question to ask and what a good answer sounds like.
  • Score your offer in four minutes with the Glass Cliff Risk Scanner.

Before you start

Being offered a top job in a struggling organisation is flattering, and the timetable is usually rushed. That is exactly when people skip due diligence. This checklist slows the process down just enough. You do not need a perfect score to accept. You need to know which risks you are taking on and whether they can be fixed in the contract. If you want a quick score first, run the Glass Cliff Risk Scanner.

Information

1. You cannot see the real numbers

Ask: "Before I accept, can I see the management accounts, cash forecast, open litigation and the last regulator letters?"

Good answer: a confidentiality agreement and a date. Bad answer: "You'll see all that once you're in."

2. Nobody will say why the last leader left

Ask: "What did my predecessor try, and why did it not work?"

Vague answers often hide a disagreement with the board that will become your disagreement too.

3. Others turned it down

Ask the search firm: "How many people have you approached, and what made them say no?" Their reasons are a free risk assessment.

Authority

4. The mandate is spoken, not written

Ask: "Can we put my scope, decision rights and how success will be judged in a mandate letter?" A mandate that is not written down can be rewritten after you fail.

5. You must keep the team you inherit

Ask: "How many senior appointments can I make in my first six months?" A turnaround with no power over the team is a turnaround in name only.

6. The board is split

Ask each director you meet: "What would you need to see in the first year to know this is working?" If the answers contradict each other, you will be judged against all of them.

Resources and time

7. "Do more with less"

Ask: "What investment is committed, and is it in a board minute?" Resources promised in conversation tend to disappear by the next budget cycle.

8. The deadline is shorter than the problem

Ask: "When will the board formally review progress?" If the answer is sooner than the time it takes to hire your team, the timeline is a trap.

9. The starting point is not acknowledged

Ask: "Will the board record the position I am inheriting?" If the crisis is not on record, you will be blamed for it.

Support and protection

10. No named sponsor

Ask: "Who on the board is my sponsor, and how often will we meet?" Leaders without a sponsor learn about problems at the same time as their critics.

11. Weak exit terms

Ask: "What happens if the strategy changes, the organisation is sold, or the board changes its mind?" Severance is cheapest to negotiate before you start, when they need you most.

12. You would be a visible "first" with no support around you

Ask: "What support do you give leaders in their first year?" Research links atypical leaders to more scrutiny and less support. A coach, a peer network and a clear communications plan reduce that risk.

When to walk awayIf the organisation refuses information (flag 1), refuses to put the mandate in writing (flag 4) and offers no resources (flag 7), the conditions for success are missing. A better title will not fix that.

Turn red flags into terms

Every flag above maps to something you can negotiate. Our guide How to negotiate a turnaround role explains how, and the Offer Protection Builder produces a prioritised list you can take into the conversation. If the offer is live and the stakes are high, a confidential role review pairs you with an adviser who has negotiated these terms before.

Weighing a role like this?

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Questions

How do I ask for financial information without looking difficult?

Frame it as preparation: you want to arrive with a plan, not spend your first month discovering problems. Serious boards expect the request and will offer a confidentiality agreement.

Should I accept if only some red flags are present?

Often yes, if the flags you see can be fixed in writing before you start. The danger is accepting while the most important ones are still open.

Who can help me review a leadership offer?

An employment lawyer for the contract and an executive coach or adviser with turnaround experience for the role itself. Our confidential role review can connect you with both.

Sources and further reading

  1. Morgenroth, T., et al. (2020). Psychological Bulletin, 146(9), 797–829. Link
  2. Glass, C., & Cook, A. (2016). Leading at the top: Understanding women's challenges above the glass ceiling. The Leadership Quarterly, 27(1), 51–63. Find the paper
  3. HBR IdeaCast: Why the glass cliff persists (2024). Link

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