How to Prepare for a Skip-Level

Throughout my time in organizations of different sizes and cultures, one of my favorite hobbies has always been to take note of the things I see going well. Albeit an overused term, I call these findings “best practices” – and am passionate about capturing them and sharing them. Many best practices I’ve found relate to communication in some way or another, usually in ways that involve and engage employees. One communication touchpoint that deserves attention is a concept called a skip-level.

Skip-levels are when an employee is given an opportunity to connect with their manager’s manager – hence: skipping a level. There are a variety of reasons for holding a skip-level meeting and a variety of ways to run them. Here’s what I’ve seen and learned so far…

How to Prepare for a Skip-Level When You’re the One Running It

As with ensuring the success of any endeavor, determine your goal before doing anything else. Are you trying to build relationships, get feedback, or perhaps get exposure to your talent pipeline? Answering these questions will make the planning easier.

Now that you’ve determined your goal, what tone do you want to set? Skip-levels can be done as one-on-ones or in small groups. They can be done in an office with a closed door, in a meeting room – or as an offsite. You’ll want to think about consistency; so if you’re in a large organization, small groups might be the most efficient option for you.

Next, you’ll want to think about messaging. This is where empathy will come into play, because your invitees might have anxiety about meeting with you without their manager present – especially depending on the politics in your organization. If the plan is for it to be informal, tell them that. If you’d like them to come with anything prepared (even questions or feedback), giving them a heads-up will increase their likelihood to participate in the kind of discussion you’d like to have with them.

Nice touches: provide a meal, snacks or coffee – depending on the time of day. Focus on your body language and facial expression to project a safe and warm environment. Start with an icebreaker or personalized small talk. Give them an opportunity to share more about their role, but also their background. Do your best to reciprocate (if not go first) with anything you ask them – so it’s truly a dialogue. And then finally, think about what last impression you want them to leave with at the end. If they bring up anything that requires follow-up, treat that importantly and with urgency – so they feel heard.

How to Prepare for a Skip-Level When You’re the Attendee

If you’ve been invited to attend a skip-level, focus on the possible benefits that could come from it instead of worrying about it – or worse – declining the invite. Prioritize this over other meetings (your boss will back you) in your calendar. A skip-level is a unique opportunity to show leadership who you are, unfiltered by anyone else. Think about your brand and how you want to be seen, especially if career growth is a goal of yours.

Even if the skip-level has been marketed as informal, with no prep needed – do your own preparing anyway. Think about what projects you’re working on that you want to highlight, or any skills you have that they might not be aware of. Having things like this in your proverbial back pocket will ensure you’re articulate in the moment, rather than regretful later of something you wish you’d shared when you had the chance.

Finally, don’t overlook the prep work behind asking good questions. In many professional settings, in fact, asking a good question can make you stand out more than sharing what you already know. Examples of good questions could include asking about the strategy behind something high-level you’ve seen going on, or about what future trends they predict in your industry, etc. If you’re feeling unsure, solicit advice from your manager – as this person’s direct report, they’ll likely have some insight to share about the things on their mind or that they value.

Basics for Everyone

The usual suspects: be on time and dress professionally. Turn off technology and give your full attention. But let’s not forget some before and after items that often get overlooked…

If you are invited via meeting request, make sure to respond to it! You’d be surprised how many people don’t know the impact of hitting “accept” vs “accept and send a response” when using Microsoft Outlook. If you don’t click the one that says “send a response,” the organizer can’t see if you accepted or declined – and it makes it look like you’ve ignored the invite. This especially matters in group settings where food is being ordered ahead of time, but a smart rule of thumb is to just always send a response to meeting requests in any setting.

Meeting organizers: craft a clear subject line to the meeting, use the body of the meeting to outline what the attendee can expect / how to prepare – and send it with at least a few days notice (if not more), so they can plan for it in their schedule.

Last but not least, the post-meeting follow-up. If you were the attendee, a classy thank you can go a long way – and allow you to reinforce what you appreciated. For the meeting organizer, I already suggested treating follow-up items with care – but also keep in mind whatever your original goal was. If you were hoping to come across as an approachable leader that values your people, find a way to show that afterwards. Could be via email – or could even be in how you interact afterwards in-person.

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For all of us, always keep in mind the power of positive reinforcement. We live in an age where people are quick to complain and have many channels to do so. The flip side to that, and a true silver lining, is that genuine appreciation stands out more than it ever did. If you really appreciate how someone interacted with you, tell them and be specific about what you appreciated. It will make them more likely to keep that behavior up, and will make you stand out.

What would you add to these skip-level best practices? Feel free to chime in, in the comments.