Skip-level meeting questions, and how not to waste them

A skip-level exists to find out what the organisation looks like from two levels down, not to review the person in front of you or the manager between you. That distinction decides everything: the moment it feels like either, you get the polite answer for the rest of the year. Say what it is for in the first thirty seconds, ask about the system rather than the people, and be explicit about what you will and will not repeat. The questions below are ordered from safest to hardest for a reason.

The questions, easiest first

Work down the list, not across it. The later questions only get honest answers once the earlier ones have shown you do something with the answers.

Open with the frame

This is not a review of you and not a review of [manager]. I am trying to understand what this place is actually like to work in from where you sit. I will act on themes and I will not attribute anything to you without asking first. Say it even if it feels obvious. They are wondering, and until it is said they will assume the worse version.

Warm-up, but real

What are you working on that you are actually pleased with? · What is something the wider team does not understand about your work? The second one is genuinely informative and it is easy to answer, which is what a warm-up is for.

The system questions

Where does work get stuck around here? · What takes far longer than it should? · What do we do that you think is theatre? · What decision are you waiting on that nobody has noticed? These are the highest-value questions in a skip-level, because they are things you genuinely cannot see and they do not require anyone to criticise a person.

The information questions

What did you find out later that you should have known earlier? · Where do you go when you do not know something? · What do you think we are hiding? The last one sounds aggressive and is not: everybody believes something is being withheld, and hearing what they believe tells you what your communication is failing to say.

The hard ones, once trust exists

What would you change first if you had my job for a week? · What is the thing people say in private that never gets said in a meeting? · Is there anything you have raised that went nowhere? Ask the last one only if you intend to chase it, because the answer creates an obligation.

How to handle criticism of the manager

Do not invite it and do not refuse it. If it comes, ask what the effect on the work is rather than what the person is like, and take it as one data point in a pattern you will check against others. Acting on a single skip-level report is how you burn both the reporter and your own credibility in one move.

The mistake that ends the programme

Hearing something and doing nothing visible. People work out quickly whether being candid with you produced anything. One skip-level where a named friction gets fixed — and is publicly attributed to "something that came up in skip-levels" rather than to a person — is worth more than a series of well-run conversations that visibly lead nowhere.

The close

Here is what I heard, here is what I am going to do, here is what I am not going to do and why. Including the third part is what makes the first two believable. Then follow up in writing within a week, and again when something actually changes.

Questions

What is a skip-level meeting?

A conversation between a manager and someone who reports to one of their reports. Its purpose is visibility into how work actually flows, not performance review and not supervision of the manager in between.

What questions should I ask in a skip-level?

Ask about the system: where work gets stuck, what takes too long, what feels like theatre, what people found out too late. Those produce useful answers without requiring anyone to criticise a colleague.

How often should skip-levels happen?

Once or twice a year per person is typical and sustainable. More often than that and it starts to look like supervision of the manager between you, which changes both relationships and rarely improves either.

Should I tell the manager about the skip-level?

Yes, before it happens, and tell the person you have. A skip-level the manager finds out about afterwards reads as an investigation, and that interpretation will spread faster than any explanation you offer later.

What if someone criticises their manager?

Listen, ask what the effect on the work is, and treat it as one data point. Do not act on a single report, and do not promise to. Check whether the same thing appears in other conversations before you do anything at all.

Should I record a skip-level?

We would not. The value of the conversation is candour that a person is choosing to extend to someone senior, and a recording device changes that calculation even when everyone consents. Take your own notes afterwards.

How do you prepare for a skip-level as the employee?

Bring one thing that is genuinely slowing the work down and one thing that is going well and is not visible from above. You do not need to prepare a critique, and a skip-level is not a performance conversation — if it starts to feel like one, say so.

Skip-levels are the clearest case for not recording a conversation. Whatever the law allows, a device on the table changes what a person two levels down will say to someone two levels up, and the candour is the entire value. Write your own notes afterwards instead.