Pre(r)amble

I have interesting and very talented members in my team that I have the pleasure to mentor, coach and work with. Some of them are at a career point where they should be reaching to the next level, and when they come for advice about it, one of the first things I say is - Get some facetime with your Skip Level.

This is important in many promotions, especially at Staff and Principal level. At that level, the person is in direct or indirect working path with the skip level. Having the context and confidence of the people’s skill makes it easy for the Skip Level to agree and nominate for promotion.

When my team members finally started to heed to my advice, they asked me “what should I talk about?”. I felt embarassed I couldn’t give a coherent answer. After all, I am pretty good with my skip-level meetings and having a great relationship with my boss’s boss. The inability to communicate it coherently made me realize that I do this as an instinct rather than it being a skill I developed. (Reading more on Trait vs Skill is interesting on it’s own). So I decided to write about it with the main aim to help people in the future.

Even without promotions involved, Skip Level 1:1s are important for transparent culture and to gain context of the team health. There are miriads of articles that discuss about the Skip Level 1:1 from the perspective of the Leader. But a good 1:1, even with your direct manager, are the ones where you go in prepared. I believe Skip Levels are doubly so. Going in prepared will show agency and will be respectful of your Skip-Level leader’s time (see their calendar to empathize how bad it can be).

General Themes for the Skip Level 1:1s

An important theme for a skip level call (also for any form of communication) is to think about this from your Skip’s POV and not from what your current role entiles.

Your Skip might be worried about how to improve organizational agility, throughput, AI adoption, increasing product revenue, stabilizing an incident ridden system or the current market condition. Talking about this just from your current scope wouldn’t be helpful. If you are aiming for next level position, having enough context to operate cross-domain is an expectation anyways. Being able to confidently discuss about product directions or how competitor is moving is expected as well.

Using 1:1s to gather feedback is pretty usual but if you ask your Skip on what feedback she has for you to improve, the generic answer you’re always going to get is to talk to your manager as they work with you on a day to day basis and that Skip doesn’t have enough context. But there is still value to gathering feedback. I would frame the question more on, “For me to achieve next level, do you see any areas where I can invest more in?”, “What "

Another important thing to talk about is what pain can you reduce for your leader. What problem they are trying to solve. See if you can help with solving it. If you get a small “homework” as part of this question, ensure you are definitely following up on it. There is no better way to increase your sphere of influence than actively being able to help your skip level leadership.

Sharing Ideas / Asking Requests

If you remember the episode in The Office where Darryl proposes to Jo Bennett, the CEO on improving a delivery technique and gets promoted to work from the office immediately. Or when Jim talks with David Wallace to become a Manager and make Michael lead the entire North East region. Those are same great examples of using Skip level 1:1s. BUT just like the Jim situation where both Michael and Jim end up in a terrible spot of being Co-Managers, align with your direct manager on these things. A good manager will support you and help you refine such ideas before you can present it. In short, use the meeting to show case good strategies and ideas that can help solve not just your problem but can help the organization as a whole. If you can showcase you are productive to have impact at your skip level, then you are showing you are ready for the next level. Whether you use the meeting to be like Jim or Darryl is in your hands!

This amazing post by Joel on how he presented to Bill Gates is a great read In this post, you can read how the whole room is astonished that Bill Gates only sweared four times during the meeting. Leaders many times cannot go into the weed of the problem to understand if this is the right decision. So instead they ask a bunch of questions to poke holes on the idea. If you are able to pass this test, then the signal is that you have done your work to back this idea. If you are not able to answer the questions, that’s a signal in and itself.

So be prepared for these types of questions if you are presenting ideas or asking questions.

Growth Conversation

Remember, in most companies, more scope or promotions, if you don’t ask for it, you don’t get it! So talking in this direction is actually good. Being direct that you are working towards career growth is good as well. Obvious mistake would be to come at it in a demanding manner but more of an interest in opportunity to work on bigger problems and having wider impact.

There is a good chance you might not meet your skip at a frequent interval. There are times you could meet them once a month, if they are a skip 2 levels above, you could probably meet them once a quarter. If you are targetting a promotion, these people have very high say in that decision and there could be more wins accumulated for you in the 1-3 month gap. Half the reason to join is to showcase your wins to your skip level leader, but how can you do it without it being like a brag on yourself? Try to share it more as an information that can help the executive. Rather than it being a “I did this last week”, try to present it as “Do you remember the problem we discussed in our last meeting, I tried to solve it by doing X, we have been able to achieve Y amount of result from it”

Preparation

Being well prepared for your Skip level 1:1 is very important.

  • Have atleast 3 good questions you have prepared
  • If you have a request to ask or sharing a bigger idea for the organisation
    • Try to be aligned with your manager on the ask
    • Be very prepared to answer the questions they will have. Play mental chess on the questions they might ask and how you are prepared to answer them
    • Remember they will be coming into it without context, Try to provide them context they need

Generic Questions

  • What can I do to make your job easier?
  • What can I do to make our business unit successful?
  • What is the most urgent problem you are solving right now? How can I help with it?
  • I am working towards a promotion, What feedback would you give for me to be successful with it?
  • What do you think we need to do better as an organization?

Conclusion

In conclusion, I think this article can be evolved more. I’d love to come back to this and add more information as I gather more context. Remember to have fun, be open, and create a good connection with your boss’s boss and good luck!