Skip-level work anniversary conversations

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

If you’re a manager of managers, work anniversaries provide a great context for having skip-level conversations with employees more than one level under you.

For employees who don’t get to speak with you one-on-one, this can be the highlight of their work anniversary. The more levels removed you are, the truer this is.

It’s also great for you. One of the awkward truths of management is that as you climb higher in the organization, you have less firsthand frontline knowledge even as you become responsible for more and bigger decisions. By coming up with a system for regularly connecting with lower-level employees, you’ll make more informed decisions.

You’ll also be perceived better. You’ll build a reputation as a leader who cares about what employees think and who actually knows what’s going on. When you make a big decision, you’ll be able to use frontline language and give frontline examples to back it up. And because of this, frontline employees will be more likely to give you the benefit of the doubt if they don’t fully understand a decision or understand the reasoning behind it.

The above two paragraphs are true about skip-level meetings no matter how you do them, but one powerful thing about using work anniversaries as the catalyst for a skip-level meeting is that it makes it far less threatening for both the employee and their direct manager. If you set up skip-level meetings out of the blue, even if it’s merely out of curiosity on your part, it will trigger anxiety for many employees and those employee’s direct managers. That just isn’t helpful.

A convenient thing about work anniversary skip-level meetings is that the urgency and extra value of a specific date makes it more likely for them to actually happen. It makes it easier to schedule well ahead of time, easier to keep the meeting scheduled, and easier to not repeatedly schedule over it.

One more thing to note is that you don’t have to have one of these meetings with every employee for every work anniversary. You might be tempted to try if you were recently promoted and feel bad that you’re not connected to the front line like you used to be, but the more indirect reports you have, the more impractical that gets. So perhaps meet with everyone hitting five years instead, or everyone hitting ten years. Just figure out how many people you can realistically talk to per year and pick the work anniversary milestones that will get you to that number.

Once you have them scheduled, what do you actually do in the meetings? You may have your own approach, and the internet abounds with ideas, but next up are a couple of ideas that work well.

The getting-to-know-them approach

If you’re going to be talking with employees you really don’t interact with or don’t know at all, a natural format is to use the time to get to know them.

Here are some especially interesting open-ended questions that will reveal a lot about what’s going on in your organization and gently nudge the employee toward constructive answers:

  • What parts of your job do you enjoy most?

  • What parts of your job do you do best?

  • What was your biggest accomplishment at work in the past year?

  • What are you looking forward to in your job over the next year?

  • Are you being challenged? What challenges would you like to take on?

  • Is anything getting in the way of sharing your opinions and ideas at work?

  • Is there a skill you’d like to learn or training you’d like to get?

  • Is there anything you need to help you do your work better?

The quick-fifteen-minute-but-still-powerful approach

Not every leader will be interested in the details to be learned from the approach above, and that’s okay. If you want to go straight to the most important content at the fastest pace, center the conversation around this single question:

  • If you had a magic wand and could change one thing about our department (or division or whatever you call what you’re in charge of), what would you change?

After you get the answer, gently probe into the backstory and find out why the employee responded that way. You may well learn as much about the employee as you do about your department.

Then use one of the following options to conclude the conversation:

  • Suggest a next step the employee can take to make progress toward making it happen. This will often be making a connection, saying something like “You know, they think about that a lot in marketing. You’ll want to talk to Pat. Let me get you their number.”

  • Suggest a next step the employee can take to research the details behind their request. For example, if they think your organization should start recycling paper clips, have them calculate how much the organization spends on paper clips each year and find out what a paper clip recycling program would cost. The idea here is that if their idea doesn’t make sense, they figure out that it doesn’t make sense without your having to say no. This avoids you being the meanie—and figuring it out on their own will teach them to think about things from other angles, which is more valuable than just having someone in authority tell them it’s not going to happen. And if their idea is a good one, the employee gains confidence and insight into the business while the department benefits from their work.

  • Simply empathize with them. Acknowledge that you can see how things would be much better if what they imagined were the case. Sometimes people just need to feel heard.

Notice that committing to doing something about their request wasn’t one of the options above. You’re busy and a lot of people work for you. If you truly can and will do something, then you can commit to it, but don’t feel pressured to. Actively and sympathetically listening to their perspective is more than enough and more than most employees get from most leaders. Then if you do do something, you can always pleasantly surprise them later!

Whatever approach you use, do this

Be curious. Stay curious and positive no matter what they say. Listen. Listen a lot.

Try not to say anything other than to ask questions—this is not a time for you to share your thoughts, it’s a time to listen to theirs.

You already know what you think and sharing it one-on-one with a low-level employee is a poor use of your time. But you don’t know what they think and finding that out is an excellent use of your time!

Tailor your questions to steer the conversation toward topics that interest you, but remember it’s not helpful for you to answer your own questions. If an employee says something you disagree with, don’t argue or explain why they’re wrong. Definitely don’t try to “constructively” share what you think. Instead, ask more questions about why they think that way and try to really see things from their perspective.

Even if they ask you what you think, don’t take the bait. Tell them that what you think is that it’s good for you to learn from others and redirect them back to talking about what they think.

You’ll be amazed at what you’ll learn!

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CEOs and work anniversaries

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Why great work anniversaries are so hard