I once worked with a CTO who was genuinely blindsided when half his platform engineering team quit within a six-week window. He’d had no idea morale was collapsing. His VP of Engineering had been reporting that things were “challenging but under control.” The VP wasn’t lying, exactly — he believed that. But he was also too close to the problem to see it clearly, and too invested in his own management reputation to raise the alarm. If the CTO had been running skip-level meetings — sitting down regularly with engineers two levels below him — he’d have heard the warning signs months earlier.
Skip-level meetings are one of the most effective and most underused tools available to senior leaders. The concept is simple: a leader meets directly with people who report to their direct reports. A VP meets with individual contributors. A C-suite exec meets with team leads or senior ICs. The meeting bypasses one layer of management, giving the senior leader direct access to what’s actually happening on the ground.
Why Your Direct Reports Filter Information
This isn’t a criticism of your managers. It’s a structural reality. Every layer of management acts as a filter. Some of that filtering is useful — you don’t need to know about every minor process hiccup or interpersonal friction. But some of it strips out exactly the signal you need.
Nobody walks into their boss’s office and says, “My team is demoralised and I’m partly responsible.” Nobody leads their weekly update with, “The architecture decision I championed six months ago is causing significant technical debt and the team resents me for it.” These things get softened, reframed, or omitted entirely. Not out of malice — out of self-preservation, optimism bias, and the very human tendency to present a managed version of reality to the person who controls your performance review.
Skip-levels give you access to the unmanaged version. The raw signal. The complaints people share with each other but never escalate. The frustrations that seem too small to bring up individually but, taken together, point to a systemic problem that’s eroding your team’s effectiveness.
Handling the Trust Problem Head-On
Here’s where most leaders get skip-levels wrong before they even start: they don’t tell their direct reports it’s happening.
Your middle managers will feel threatened by skip-level meetings. That’s a guarantee, not a possibility. If they find out you’re meeting with their team members without warning, they’ll assume you’re investigating them, evaluating their performance through back channels, or preparing to undermine their authority. The relationship damage can be severe and fast.
Address this before you hold a single skip-level. Tell your direct reports — ideally in a team meeting, not in a side conversation that feels secretive — that you’re going to start holding regular skip-level conversations. Explain your reasoning plainly: you want broader visibility into team health, you want to hear directly from people doing the work, and you want to build relationships across the organisation. Make it clear that skip-levels are not performance evaluations of the middle manager and that you won’t use them to second-guess their operational decisions.
Then actually follow through on that commitment. Because if you hear something in a skip-level and immediately march into your VP’s office saying, “Sarah told me the deployment pipeline is a mess — why haven’t you fixed this?” you’ve just destroyed two things simultaneously: Sarah’s trust in the process and your VP’s willingness to support it.
Frequency, Format, and Setting Expectations
Monthly or quarterly, depending on your organisation’s size and your own calendar constraints. 20-30 minutes per person. Informal. No agenda document. No action items tracker. This is a conversation, not a review.
For remote and hybrid organisations, a video call works fine. Don’t overthink the format. The value comes from the conversation itself, not from the medium.
Set expectations with the people you’re meeting, too. They’ll be nervous. Most individual contributors or team leads have never had a one-on-one with someone two levels above them, and their first instinct will be to treat it as a status update or — worse — a chance to lobby for a promotion. Neither is what you want.
Open with something like: “This isn’t a performance review or a status meeting. I’m trying to get a better sense of how things are going from your perspective — what’s working, what’s frustrating, what you’d change if you could. There are no wrong answers and nothing you say here goes back to your manager attributed to you.” That last part matters enormously. If people think their words will be quoted back to their boss, they’ll give you the same filtered information your direct reports already provide.
Questions That Actually Surface Useful Signal
“Do you have any concerns?” is a terrible skip-level question. It’s closed-ended, it puts people on the spot, and the default answer is always “no” or “nothing major.” You need questions that invite narrative, that give people permission to be honest without feeling like they’re complaining.
Good skip-level questions sound like ordinary conversation. “What’s taking up most of your time right now?” tells you where effort is actually going versus where leadership thinks it’s going. “What’s one thing that slows your team down that you think could be fixed?” surfaces process friction that managers often accept as normal. “If you had my job for a week, what’s the first thing you’d look at?” is surprisingly effective — it gives people permission to think at a strategic level and often produces insights about blind spots you didn’t know you had.
“What’s something you wish leadership understood better about your work?” is another strong opener. It frames the conversation as you seeking to learn, not them seeking to impress. And don’t be afraid of silence after you ask a question. Count to ten in your head if you have to. People need processing time, especially when they’re talking to someone senior. The person who fills silence first loses information — and in a skip-level, that person should not be you.
Avoid asking about their manager directly. “How’s your relationship with David?” puts them in an impossible position. If they have issues with David, they’re not going to tell David’s boss in a 25-minute meeting. You’ll learn about management problems indirectly through the patterns in what people tell you — and that indirect signal is more reliable anyway.
What to Do with What You Learn
This is the part that separates leaders who get value from skip-levels and leaders who create political disasters.
You will hear things that concern you. Someone will tell you the QA process is broken. Someone else will mention that the team hasn’t had a proper sprint retrospective in four months. A third person will hint that their manager plays favourites when assigning high-visibility projects.
Your instinct will be to fix it immediately. Resist that instinct.
If you act on a single data point from a single skip-level conversation, you create three problems. First, the person who told you feels exposed, even if you don’t name them — in a small team, it’s obvious where the information came from. Second, your middle manager feels surveilled and undermined. Third, everyone else in the organisation learns that skip-levels are a mechanism for escalation, which means people will start using them strategically to go around their managers, and the whole system becomes political.
Instead, look for patterns. If one person says the deployment process is frustrating, that’s an opinion. If four people across two teams independently mention deployment friction, that’s a pattern you can address without attributing it to any individual. Bring it up with your direct report as something you’ve “been hearing about from multiple sources” and ask them to investigate. That’s how skip-level intelligence translates into action without burning anyone.
Keep a private running log of themes. Over three or four rounds of skip-levels, you’ll start seeing recurring topics that don’t surface through any other channel. Those recurring themes are where the real organisational insight lives.
Skip-Levels Matter More When Your Team Is Distributed
In a co-located office, senior leaders absorb ambient information constantly. You overhear a frustrated conversation in the kitchen. You notice that one team’s area has gone quiet. You catch the mood in a hallway after an all-hands meeting. None of this is formal. All of it is valuable.
Remote and hybrid organisations strip out this ambient signal entirely. Your information channels narrow to Slack messages, structured meetings, and whatever your direct reports choose to tell you. The filtering effect that already exists gets amplified, sometimes dramatically.
A 20-minute video call every six weeks with someone two levels down gives you back a fraction of the informal signal that used to come from walking the floor. It’s not a perfect substitute, but it’s the best replacement available. And frankly, many distributed organisations would function meaningfully better if every director and above committed to 2-3 skip-level conversations per month. The investment is small — maybe 90 minutes of calendar time — and the information return is disproportionately high.
Scaling Skip-Levels Without Losing Your Calendar
The obvious objection: “I have 200 people in my organisation. I can’t skip-level with all of them.”
Correct. You don’t need to. Pick 3-5 people per quarter on a rotating basis. Vary the teams you draw from each round. Over four quarters, you’ll have spoken with 12-20 people across your organisation — enough to build a meaningfully richer picture than you’d get from dashboards, engagement surveys, and town halls combined.
Selection matters. Don’t only talk to high performers or vocal people. Include the quiet mid-performer on the infrastructure team who’s been in the company for four years. They often have the deepest institutional knowledge and the sharpest observations about what’s changed for the worse. Mix tenure levels, mix teams, mix seniority within the skip-level range. You’re sampling, and a biased sample produces biased conclusions.
Some leaders use a randomised system — literally pulling names from a list. Others ask their direct reports to nominate people (though this introduces its own bias, since managers may nominate people they’re confident will say positive things). My preference is a rotating schedule that you control, with occasional ad-hoc additions when something specific is happening in a particular team. Keep it semi-structured but not rigid.
Common Mistakes and How to Avoid Them
Turning skip-levels into status updates. If you’re hearing project timelines and deliverable lists, the conversation has gone off track. Gently redirect: “I can get project updates from the dashboard. What I can’t get from a dashboard is your honest take on how things are going.”
Going too long between sessions. If you do skip-levels once a year, they feel like a big deal — formal, high-stakes, unnatural. Quarterly or monthly cadence normalises them. They become just another conversation, which is when people start being genuinely honest.
Failing to close the loop. If multiple skip-level conversations surface a common theme and you take action on it, let people know — without attribution — that their input contributed to the change. “Based on feedback from across the organisation, we’re restructuring how we handle deployments” tells people their input mattered. If they never see any result from their candour, they’ll stop being candid.
Using skip-levels to gather evidence against a manager. If you suspect a manager is underperforming, address that through proper performance management channels. Skip-levels are a sensing mechanism, not an investigation tool. The moment people perceive them as investigations, the whole programme collapses.
Starting Tomorrow
You don’t need a programme, a framework, or a rollout plan. You need to tell your direct reports what you’re doing and why. Then pick three people across your organisation, send them a 20-minute calendar invite with a note that says, “No agenda — just want to hear how things are going from your perspective.” Hold the conversations. Take notes afterwards (never during — it changes the dynamic). Look for patterns across conversations. Act on patterns, never on individual disclosures.
The information you’ll get from six skip-level conversations per quarter will reshape how you understand your own organisation. You’ll spot retention risks before they become resignations. You’ll catch process dysfunction before it becomes a crisis. You’ll build relationships with people two levels down who’ll remember that their senior leader took 20 minutes to ask how they were doing and actually listened to the answer.
That matters more than most leaders realise. The executives who manage effectively across levels aren’t the ones with the best dashboards or the most detailed weekly reports. They’re the ones who maintain direct human connections throughout their organisation — who know what’s actually happening because they took the time to ask the people doing the work, rather than relying exclusively on the people managing the work.
Skip-levels are how you stay connected as your span of control grows. If you’re building a team or already running one, and you’re not doing skip-levels yet, start this month. The barrier to entry is zero. The potential upside is enormous. And your operating effectiveness as a senior leader depends on having information that your formal reporting lines alone cannot provide.
For further reading on structuring skip-level meetings, The Engineering Manager’s guide covers the mechanics well, and Fellow.app’s skip-level resource has useful question templates you can adapt to your context.
Ben is a full-time data leadership professional and a part-time blogger.
When he’s not writing articles for Data Driven Daily, Ben is a Head of Data Strategy at a large financial institution.
He has over 14 years’ experience in Banking and Financial Services, during which he has led large data engineering and business intelligence teams, managed cloud migration programs, and spearheaded regulatory change initiatives.