Skip-Level 1-on-1s: The Underrated Practice for Stronger Engineering Teams
And how to make them your secret weapon for sustaining alignment
As engineering teams grow, even small communication gaps can quickly morph into major morale or retention problems. When you’re a tight-knit group of ten, knowledge and feedback flow almost automatically.
But as soon as you hit twenty or more engineers, even small misunderstandings can quietly balloon into major morale or retention problems. That’s where skip-level 1-on-1s come in. While they’re often overlooked or introduced too late, skip-level meetings can become your secret weapon for sustaining alignment, trust, and engagement as your company scales.
What Are Skip-Level 1-on-1s
A “skip-level 1-on-1” is a periodic conversation between a senior leader - Director, VP, or CTO - and the direct reports of their own direct reports. Essentially, you’re “skipping” one level of management to speak directly with their reports. The value of these chats becomes especially clear during rapid growth, when even your best managers struggle to relay every piece of information accurately and in a timely manner.
When teams expand, it’s not just the engineering headcount that grows. You introduce new managers, shift responsibilities, and roll out new products at a faster pace. Despite everyone’s best intentions, information silos and communication gaps inevitably form. A skip-level 1-on-1 ensures that you hear about these issues - big or small - directly from the people feeling the impact on the ground. This is vital when you want to maintain a pulse on your culture, retain your best people, and keep your roadmap aligned.
The problem is that many organizations adopt skip-level 1-on-1s reactively, only after a major issue forces them to do so. By this moment, you might already suffer from disjointed strategy, or seeing key projects stall. In contrast, leaders who recognize the power of skip-level meetings early and weave them into their growth strategy are far more likely to maintain a healthy culture, empower first-time managers, and catch potential problems before they escalate.
Benefits of Skip-Level Meetings
Here are some key benefits od skip-level-1-on-1s:
Open-Door Policy: Myth vs. Reality
Many leaders often say: “My door is always open” (or “feel free to schedule a call with me any time” in a remote environment). But in practice, many people hesitate to do this uninvited. They might worry about stepping on their manager’s toes or fear being labeled as complainers. A skip-level 1-on-1 reduces this barrier, offering a safe and structured space for employees to talk candidly about challenges, frustrations, and opportunities.
Direct Insight into Team Health
While your first-line managers can (and should) give you status updates, hearing from the team directly brings context and details you might otherwise miss. It’s one thing to see metrics in a dashboard or read a manager’s summary; it’s another to hear an engineer describe how a process is slowing their progress or creating friction.
Career Growth and Retention
Everyone on your team wants to know that leadership cares about their career trajectory. Regular skip-level conversations give you an opportunity to remind them of organizational goals, highlight pathways for growth, and gather feedback on how well those pathways are working. When people feel heard and see tangible follow-through, they’re more likely to stay and remain motivated.
Feedback on Your Management Layer
Skip-levels provide constructive feedback on how your managers are doing. You’ll rarely make decisions based on a single conversation, of course. But over multiple sessions with different team members, you might identify patterns - perhaps one manager consistently excels at building engagement, while another struggles to communicate project goals. This insight is incredibly valuable for mentoring and developing your leaders and managers.
Visibility into Bigger Picture
Senior leaders have broader context, from product strategy to organizational priorities. Skip-level sessions enable Individual Contributors to ask high-level questions about company direction, or to confirm whether their work aligns with bigger goals.
Stepping on Managers’ Toes? Here’s How to Avoid It
It’s natural for frontline managers to worry that skip-level 1-on-1s could undermine their role. The best way to prevent this is by establishing boundaries. Let everyone know that day-to-day decisions remain with the immediate manager. Your role is to listen, help surface issues, and offer support. If a concern arises about a manager’s behavior or leadership style, handle it discreetly. Ideally, by encouraging open communication between both parties.
Introducing Skip-Level 1-on-1s
Introducing skip-level meetings for the first time requires clear communication and a careful approach:
Start with Your Direct Reports
Explain the purpose to your frontline managers: you’re not trying to bypass them or undermine their authority. Emphasize that skip-levels are a feedback loop, not a tool for micromanagement and putting blame on anyone.
Be Transparent with the Team
When inviting someone to a skip-level meeting, clarify why it’s happening and what to expect. Let them know their feedback will remain confidential, except for broad themes you might need to share with managers to fix issues.
Pick a Reasonable Cadence
Quarterly skip-levels often strike a good balance. Too frequent, and you risk overshadowing your managers. Too infrequent, and you may miss urgent problems.
Follow Through
If you learn about systemic issues, work with your managers to address them. Then circle back to the team member who raised the concern so they know their voice was heard.
How To Run Effective Skip-Level 1-on-1s
A good skip-level 1-on-1 is typically 30 minutes to 1 hour. You want structure, but you also want to create space for organic conversation.
Use this template to guide the discussion:
Check-In
“How are things going for you personally?”
“Anything fun or interesting happening outside of work you’d like to share?”
Well-Being and Motivation
“How do you feel about your current workload and responsibilities?”
“On a scale of 1-10, how supported do you feel by your manager and the team?”
Career and Growth
“What skills are you planning to develop in the next 6-12 months?”
“Are you happy with where you are now in your career?”
“Is there any training or mentorship you’d find helpful?”
Company Strategy and Feedback
“Is there anything about our broader strategy you find confusing or concerning?”
“If you could change one thing to make our team or product more effective, what would it be?”
Open-Ended Questions
“Is there anything else you’d like me to know that we haven’t covered?”
“Any questions for me, whether about the team, the product, or the company direction?”
Rating morale at the end of the conversation is a valuable practice as it allows you to track the metric over time and compare it with the perception of your managers
Wrapping Up
Whether your organization is adding its first batch of new engineers or you’ve already grown into a larger operation, skip-level 1-on-1s are a powerful way to keep everyone grounded and engaged. They offer a direct line to real feedback, help you catch issues early, and reinforce a culture of trust—especially in times of rapid growth.
If you haven’t tried them yet, this is the perfect time to start. Introduce them carefully, keep the cadence reasonable, and be transparent with both your managers and their teams.
The result? Fewer blind spots, stronger retention, and a healthier engineering culture that stands resilient no matter how fast you’re growing.