The Meeting You’re Called Into After Vacation

A staff member asks for a meeting, and you don't know which way it's going to go. Neither did I.
· September 9, 2026 ·4 min read

A valued staff member asked me for a meeting soon after vacation. It wasn't unusual for him to ask to meet, but the tone was different this time. I felt it mattered before he said a word.

I didn't know which way it was going to go. Was it a concern with a colleague? A new idea he wanted to share? Or did he need to sort a problem out with me? People often come back from time away with a reflection, and I sensed something in the air before we sat down.

After a little small talk, he came to the point. He had to give his notice. He'd been offered a role with another organization - more money, less work, better prospects. He had to make the decision for his family. I told him I was happy for him. Grateful for the time we'd had. Excited for what was in store for him. All of that was true.

And underneath it, as a leader, I also felt real tension and fear. I didn't know what came next for our team. Who was going to manage the role. I wondered how fast I'd need to move. I felt real pride in him for finding the right next step and also a sense of personal loss. Both in the same conversation. I think back and wonder what I could have done differently.

When you face internal change you second-guess how you set up succession. Is it possible to prepare well enough that you're not left scrambling? If you're a good leader, you know you need to think it through ahead of time and prepare for it - to avoid the surprise.

Paying attention ahead of time starts with one habit, and there's a specific moment it works best: the return from a break.

When people come back from vacation they may have taken some time to reconsider their future. They finally got a real break, maybe for the first time in a while, and somewhere in it they asked themselves a question they don't usually have time for: do I want to keep spending my time here? Some come back refreshed and re-committed. Others come back counting down. Miss that window and you may find out which one it was in a meeting you didn't see coming.

The move is to sit down with your staff and ask, regularly and directly about how they feel about their fit for the future. Not "just wanted to check in, how are things going" - I've written before about why that opener does the opposite of what it intends. Be prepared and say what this conversation is about, and why, before you ask these important questions.

There's a name for this in HR circles: stay interview questions. Three of them can save you a lot of time later.

Where do you want to grow? Ask if they sense a place where they are stuck, or better yet, see if they hold hope to build a new skill for the team. If you see a potential leader in the mix, consider how you are preparing them for the role - it's not by happenstance and hope.

Where do you see yourself right now? It's always a good idea to take stock of where people are feeling they currently stand, then ask them about the future. What is their intent going forward? Offer your take and ask: Would you like to hear what I see in you?

What can I do to help? A staff member who is feeling unsettled is looking for the next steps. Simply asking "What do you need to take the next step?" is the kind of support that's simple, appreciated, and often overlooked by leaders (might be our fear of finding out they are looking elsewhere). Be the resourceful leader that your team relies on. It doesn't even have to be budget. It can be as simple as advice, a timely article or an introduction.

If they have ready answers to your questions, you may have just found out something important about planning your next season with them.

If they don't know, that's not a bad answer. That's the job.

I still would have lost my guy. Better money, less work, a decision for his family - that was the right choice for him, and I meant it when I said I was glad. But sometimes the decision to leave is less about the money and more about the opportunity.

If you want to keep your best people, open that conversation right after the next vacation. That's when they're already asking themselves these questions, so you're supporting the process instead of reacting to it. Ask, and you hear what might be coming before it becomes a decision. Skip it, and you might be on the receiving end of a meeting invite you'd rather not manage right now.

If you don't know where you're developing right now, or you're not sure your own people could answer that question either, the Leadership Check-In is a fast way to find out.

En route, but aren't we all.

Want to know how your leadership is actually landing? Start the Leadership Check-In - free, twenty minutes.
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