As a startup scales, there is a real risk that leadership will lose connectivity to junior employees. Enter skip level 1:1 meetings. 

What is a Skip Level?

A skip level is where an executive meets routinely, in a 1:1 format, with an employee that is 2 or more levels their junior in the org. 

Why are they useful?

Skip levels are a great way for an executive team to maintain, and even strengthen, communication lines across the company as it scales. In addition, leaders can also use skip levels to keep a pulse on employee satisfaction, engagement, alignment, and progress at multiple tiers. Finally, they’re a great conduit for informal feedback on management layers outside of normal review cycles. 

Want to implement skip levels in your org? Or improve how you run yours? Guild members recently shared their suggested frequency, highest-leverage questions, and additional tips.

What’s the right frequency?

The average Guild member hosts skip levels 1:1s every 6 to 8 weeks with the most frequent members hosting at a monthly cadence and the least frequent at a quarterly cadence. 

Top Questions Guild Members Ask

  1. What would you rate your happiness at our company on a scale from 1 to 10?
  2. What blockers are you running into?
  3. Do you have any feedback for your manager that you don't feel comfortable giving her directly?
  4. What works well in your team right now? (i.e. systems, processes, technology, feedback, etc.)
  5. Are our company goals clear? Is it clear how your work connects to them?
  6. What needs improvement? What obstacles are making it hard to be successful? (i.e. technology, top-level support, more feedback, etc.) 
  7. What is one thing, as a team, we need to Start, Stop, Continue doing to be more successful?
  8. What do you need more (or less) of from your manager and yourself in order to be successful as a team and in your role?
  9. What’s the most annoying thing to you these days? (Great insight for what’s not working)
  10. What do you believe we're doing well as a team?Where are areas for improvement/growth?
  11. What are the most acute pain points? 
  12. Is your contribution to the company's mission and goals clear?
  13. Are you having fun?
  14. Are you happy?
  15. Who is kicking ass on the team?
  16. If you were me how would you handle X?
  17. What should I be thinking about which I'm not?
  18. What could I be doing better?

Engineering Specific

  1. Are there any systems you have concerns about?
  2. Any technical debt you'd like to see addressed?
  3. What tools or tech would help you accomplish ____?

Other tips from seasoned leaders

Create a Safe & Trusted Space: Establish with everyone that you’re their biggest cheerleader and invested in their career growth. This skip level space is safe and non-judgmental and they can expect honest answers from me at all times.

Share Prompt Questions Ahead of Time: Make sure to include your typical questions in the cal invite so they can prep ahead if they’d like to.

Convey the Why: I tell every skip level of mine before we start: "This meeting is a forcing function to ensure you always have time with me. We could use this time to just shoot the shit and connect personally, we could use it for feedback you might have, or we could use it for answering absolutely any questions you might have from a business perspective, like strategy, financials etc."

Be Cautious of Too Much Feedback Out of Cycle: While constant feedback can be helpful, I suggest relying on feedback cycles for manager reviews because it can be a tricky area to navigate and want to both be informed but also leave space for the manager & direct report to work through. I've found this is especially critical for a younger team (in terms of years of work experience).

Bonus: How to Run Skip Levels at Public Scale

We recently had Kimber Lockhart (One Medical's CTO) in to speak to the CTO Guild and she shared a few specific tips on skip levels. As they reached public scale, she shifted her skip-levels to a less regular cadence - roughly every 3-4 months. Eventually, she noted, your team size will reach a point where even rotating skip-levels can no longer scale. When this happens, the question becomes: how can leaders still cultivate 1:1 connectivity with everyone in the org?  

Enter “Coffee with Kimber” (or 1:8 meetings). Team members meet with Kimber in a group setting, with roughly eight team members at a time. The conversations have loose structure to them, creating a trusted space to talk about what’s going on in the organization, victories, losses, and open questions and concerns. These are similar in nature to an alternative structure many leaders embrace (“office hours”), but rather than being hosted on opt-in basis with no agenda, they retain the sacrosanct nature and loose structure of an effective 1:1 meeting. 

Rotating skip-levels and “Coffee with” enable leaders to continue to get signals and create a holistic picture of what’s going on across the organization.