The EA guide to how work anniversaries help with skip-level one-on-ones

by Rick Joi
Rick Joi is the founder of The Workiversary Group and author of the award‑winning book, Inspiring Work Anniversaries.

This is valuable for any executive who manages managers, but the value keeps increasing more and more the larger the number of employees in the organization under your executive.

Skip-level one-on-ones are really valuable

The idea of a skip-level one-on-one is that it provides an executive the opportunity to gain a better understanding of what’s really happening in the organization on the front-line.

There are a few common reasons why useful information might not reach an executive. In an unhelpfully-political organization, each level of management may be trying to put forward a rosy picture intended to make each individual look good. In a performance-oriented or efficiency-oriented organization, managers may just work hard to instill a can-do attitude for working around challenges rather than “complaining” about them, since the manager can’t do anything about the challenges, which inhibits information about systemic challenges reaching the executives who could launch the change initiatives which would lead to big improvements. And lastly, there’s just old-fashioned whisper-down-the-lane where details get inadvertently changed or omitted as they pass through multiple layers of management.

How work anniversaries solve the common tactical problems

While skip-level one-on-ones can solve a clear and nearly universal problem, there are tactical obstacles that lead many organizations to not have any sort of formal process for skip-level meetings. Luckily, work anniversaries can play a big role in overcoming these obstacles:

  • Who to talk to since there’s not enough time to talk to everyone? Employees often make up stories where there are none, especially when it comes to the actions of executives. If an executive starts talking to selected employees and no one can make sense of who is selected or why, it’s not uncommon for a story that they’re preparing layoffs to be suggested.  If, on the other hand, it’s well known that the conversation is to commemorate a milestone work anniversary, then the problem is neatly solved.

  • How to prevent employees from feeling like they’re “going to the principal”? This isn’t true of everyone, but there are a lot of employees who are filled with anxiety when asked to speak to someone in a position of power. They are reminded of having to speak to the principal when they were at school and it representing being in trouble. They can be assured that “it’s just to talk”, but the anxiety will still be there. However, substitute in a message that the executive “wants to commemorate their work anniversary by thanking them in person and checking in on how things are going”, and, while the most anxious among us will always be anxious, a lot more people will be comfortable with the meeting.

  • How to stop the meetings from being canceled? Executives always have a lot going on. Their job is not to figure out how to juggle all the balls, but to figure out which ones to drop. Skip-level meetings can be those balls if there’s no obvious urgency to the meeting. But, the wonder of work anniversary skip-level meetings is that they have built in urgency. The meeting is clearly most valuable on the day of the work anniversary and much more valuable close to the work anniversary than far away. And, canceling it altogether will clearly do some damage. And so, with the extra value of commemorating a work anniversary, many more skip-level meetings will actually happen.

The format of the meeting

There are multiple formats for the skip-level one-on-ones.

The most time consuming, but also path to the closest connection, is for the pair to breakfast or lunch. If you go down this path, I would highly recommend aiming for choosing which milestone anniversaries to include such that you’re aiming for no more than one per month. That is, if you declare that the executive is going to meet with every employee hitting a work anniversary evenly divisible by 10 (10, 20, 30, etc.), then you’ll want to make sure that that’s only going to be about ten employees in any given year. More than that, and most executives will find it to be too much of a drain on their time.

A path on the other end of the spectrum that allows for the executive to meet with more employees is to schedule 15-minute meetings in the executive’s office or as a video call. The most common 15-minute format is to do a “magic wand” meeting. For this type of meeting, the executive simply asks the question, “if you had a magic wand, what one thing would you change about the organization?” These conversations are both brief and surprisingly insightful.

Final thoughts

Your executive will probably immediately have a preference, or geography may limit your options. All of the formats are good. What matters most is that the executive enjoys it and thus is more likely to stick with it.

One more idea to be aware of is, if your executive is conflicted about how many people they’d like to meet with and how much time that would take, then you can suggest that you put in a program where it’s split up among the executive’s senior team. This is of course more work for you, but it’s also a bigger impact where many more executives will get wisdom from the front line, and their group discussions will be greatly enriched.

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The EA guide to organization-wide work anniversary acknowledgement

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The EA guide to work anniversary breakfasts