Skip-Level 1:1 Question Bank

60 questions for leaders running skip-levels — 1:1s with a manager's direct reports, without the manager present. Used well, these surface blind spots the direct manager can't see from inside the relationship. Used badly, they undermine the manager and teach the team to go around them. Read the ground rules first.

Ground Rules — Say This at the Start, Every Time

"This isn't about going around [manager's name] — I do these with every team so I stay close to what's actually happening. Anything you tell me, I'll only act on in a way that helps you and the team, and I won't quote you back to [manager] by name unless you tell me it's okay to."

Never open with "so how's your manager doing" — it frames the whole conversation as a manager audit. Start with the rep's own experience and let manager-related answers emerge naturally.

A. Manager Coaching & Support (8)

1. "When did you last get feedback that actually changed how you do something?"
2. "How often do you and your manager talk about your development versus your numbers?"
3. "What's something your manager does in coaching that you wish every manager did?"
4. "Is there a skill you've been trying to build that you feel like you're figuring out on your own?"
5. "When you bring a problem to your manager, what usually happens next?"
6. "How would you describe your manager's coaching style in one sentence?"
7. "What's one thing that would make your 1:1s more useful to you?"
8. "Do you feel like your manager knows what you're actually working on, day to day?"

B. Career Growth & Development (8)

1. "Where do you want to be in 18 months, and does your current role get you there?"
2. "What's a skill you have that isn't being used right now?"
3. "Have you had a real conversation about your career path here in the last six months?"
4. "What would need to be true for you to feel confident about your next move, here or elsewhere?"
5. "Is there someone here whose career path you'd want to follow?"
6. "What's one thing holding you back from the next level, in your own honest view?"
7. "If you could design your own development plan, what would be in it?"
8. "What would make you feel like this company is genuinely investing in you?"

C. Team Culture & Psychological Safety (8)

1. "When was the last time you disagreed with a decision — what happened when you spoke up?"
2. "Do you feel like mistakes on this team are treated as learning or as liabilities?"
3. "Is there anything you've stopped bringing up because it didn't seem to go anywhere last time?"
4. "How does the team handle it when someone's having an off quarter?"
5. "Would you describe this team as competitive or collaborative — and how do you feel about that?"
6. "Is there anyone on the team whose voice doesn't get heard as much as it should?"
7. "What's something the team does well that doesn't get enough credit?"
8. "If something were wrong on this team, would you feel comfortable telling me directly?"

D. Workload & Process Friction (7)

1. "What's the most frustrating part of your week that has nothing to do with selling?"
2. "Is there a tool or process that wastes more time than it saves?"
3. "What do you spend time on that you don't think should be your job?"
4. "How realistic does your current workload feel, most weeks?"
5. "What's something that used to be easy and has gotten harder?"
6. "If you could eliminate one recurring task from your week, what would it be?"
7. "Where do you feel like you're duplicating effort with someone else?"

E. Recognition & Fairness (7)

1. "When did you last feel genuinely recognized for something — what was it?"
2. "Do you feel like effort and results are recognized evenly across the team?"
3. "Is there anyone here you think is underrated?"
4. "How do you feel about how comp/quota decisions get made and communicated?"
5. "Is there a difference between how top performers and everyone else get treated here?"
6. "What's something you did recently that you're proud of, that maybe no one else noticed?"
7. "Do you feel like the same people always get the good opportunities?"

F. Strategic Alignment & Communication (7)

1. "Do you understand why the company is prioritizing what it's prioritizing right now?"
2. "What's a decision from leadership recently that you didn't understand the reasoning for?"
3. "How well does information flow from leadership down to you — where does it get lost?"
4. "If you had one question for leadership that never gets answered, what would it be?"
5. "Do you feel like you know what's coming in the next quarter, or does it feel like surprises?"
6. "What's something leadership says that doesn't match what you actually experience day to day?"
7. "How connected do you feel to the bigger picture of what this company is trying to do?"

G. Retention & Engagement Signals (8)

1. "What would have to change for you to think seriously about leaving?"
2. "On a scale of 1-10, how likely are you to still be here in a year — and what's behind that number?"
3. "What's something a competitor or another company could offer that would actually tempt you?"
4. "When's the last time you thought about leaving, even briefly — what triggered it?"
5. "What keeps you here that isn't the paycheck?"
6. "If a recruiter called you tomorrow, what would they need to offer to get you to take the call seriously?"
7. "Is there a version of your job here that would make you want to stay long-term?"
8. "What's the one thing that, if it happened, would make today your last good day here?"

H. Closing / Forward-Looking (7)

1. "If you were me, what's the one thing you'd go fix after this conversation?"
2. "What haven't I asked that I should have?"
3. "Is there anything you want me to know that you haven't said yet?"
4. "What's one thing that would make the next skip-level even more useful?"
5. "How do you want me to follow up on anything we've talked about today?"
6. "Is there anything here you'd rather I didn't act on, even generally?"
7. "Anything else on your mind before we wrap up?"

What to Do With What You Hear (Follow-Up Protocol)

1. Never quote a rep to their manager by name without explicit permission — ask directly: "Is it okay if I mention this to [manager], and how do you want me to frame it?"
2. Aggregate before you act. A single comment is a data point, not a verdict. Look for the same theme across 2-3 skip-levels before treating it as a pattern worth raising with the manager.
3. Route manager-coaching gaps through development, not discipline — if multiple reports flag the same coaching gap, that's an input to the manager's own development plan (see the Coaching Effectiveness Scorecard for Managers), not a surprise write-up.
4. Close the loop with the rep. If you acted on something they raised, tell them — even briefly. Skip-levels that go silent train people to stop being honest in them.