Working with your manager
Ask for a skip-level conversation
A simple conversation to understand where your group is headed, from the person helping set the direction
Ask your manager's manager for 30 minutes to hear where the group is headed, and bring two or three thoughtful questions.
- 30 minutes
- You and your manager's manager
- Once or twice a year
- Conversation
Why this can work
Your manager's manager sees the bigger picture your manager is working inside. Hearing where the group is going, from someone helping steer it, lets you aim your work at what matters most.
Read moreHow to ask for a skip-level meeting
You’ll come away with a clearer view of where the group is headed, and one way your work connects to it.
- Tell your manager first.
Mention it before you ask, so it never looks like going around them. Many managers are comfortable with it, especially when you say why, and many have useful context to offer.
You“I'm thinking of asking your manager for half an hour to understand where the group is headed. Any advice before I do?” - Ask for 30 minutes.
A short note that says what it's for and makes it easy to say not yet.
To: your manager's managerI'd love 30 minutes sometime in the next few weeks to hear how you see the group's direction over the next year or so. It would help me make sure my work is pointed at what matters most.
I'll come with a few questions. And if this is a busy stretch, later is completely fine.
Swap the highlighted parts for your thing. Works on Slack, in email, or said out loud. - Prepare two or three questions.
About direction, not complaints. What is the group trying to achieve this year? What's the hardest problem they're working on? What would they want someone in your role to understand better?
- Ask for their advice.You“What advice would you give someone in my role who wants to be more useful to where the group is going?”
- Share what you learned with your manager.
A two-line summary afterward keeps them in the loop, and often hands them something useful too.
Good times to repeat it: once or twice a yearwhen the group's direction changesa few months after you get a new manager
Making it work for you
Every workplace is different. Here’s what to think about before you start, and what might get in the way.
Things to think about
Senior leaders usually answer for a few big outcomes. Knowing them tells you which of your projects will find support, and which will have to fight for it.
What might make this harder
Ask what worries them, and offer to share what you learn. If they'd still rather you didn't, wait, or suggest they join you.
Questions people ask
What is a skip-level meeting?
A conversation between an employee and their manager's manager, skipping a level in the reporting line. It's usually about direction and priorities, not about the manager in between.
What questions should I ask in a skip-level meeting?
Two or three about direction: what the group most needs to get right this year, what's hardest for them right now, and what advice they'd give someone in your role.
Is it okay to ask for a meeting with my boss's boss?
Usually, yes, as long as your manager knows and the purpose is clearly about direction. Many senior people welcome it.
Should I tell my manager about a skip-level meeting?
Yes, before you ask. It keeps trust intact, and your manager may have useful context for the conversation.
Why this works, and where it comes from
Company direction usually reaches people secondhand, a few layers down, with the why worn off along the way. Priorities that look arbitrary from where you sit often make sense a level or two up. A short conversation with someone setting direction can fill in the missing reasons in a way no all-hands tends to.
Skip-levels are usually something managers arrange for their teams. Asking for one yourself is less common, and it works just as well when the purpose is plainly about direction rather than about your manager. Asking for advice instead of feedback helps. People find it easier to suggest than to assess, and what they suggest often tells you what they value.
There's something in it for them too. Senior leaders often have less contact with the day-to-day work than they'd like, and a thoughtful question from someone doing it is genuinely useful to them. Coming prepared, curious, and interested in what they're trying to achieve makes you someone whose name they remember for the right reasons.
In your first few weeks with a new manager, hold off. Asking their boss for time before you've built anything with them can look like hedging. A few months in, the same request reads as curiosity.
Other simple things to consider
What to do next
More in Working with your manager
A few minutes that compound
Do it with Truest and it goes on your permanent record, in a Career Vault your employer doesn’t own.
See how Truest worksAlready a member? Log in- A reminder beforePut it on your calendar and Truest reminds you before it starts.
- On your recordWhen it's done, it goes on your record with your priorities and progress.
- Kept with the thing it was aboutSave what comes back in your Vault, next to the work it was about.
Read this alongside your role page
Tell Truest what you’re dealing with
We read every one, and we write guides for the things that come up most. Leave your email if you’d like to hear when we do.
An exercise written by Truest, based on our experience. Last updated September 25, 2026. We sell a career membership; where that’s relevant above, we say so.