You’re about to have your first round of 1:1s in 2026. Most managers will ask the same “small talk” questions:
“How were the holidays?”
“Ready to get back into it?”
“Any New Year’s resolutions?”
And those are good, personable “warm up” questions to get back in the swing of things. But they won’t really discover anything or allow you to move forward with your team.
Here’s the one question that will change how your team thinks about 2026:
“What’s the one thing that, if it happened this year, would make you say ‘this was a great year at work’?”
Then shut up and let them think.
Asking this question does three things:
- It surfaces what actually matters to them. Not what they think you want to hear. Not the corporate-approved career development language. What they actually care about.
- It gives you a target. Now you know what success looks like from their perspective. You can work toward that, check in on it, and actually help them get there.
- It shows you’re invested. Most managers never ask. By asking—and then following through—you’re already different from 90% of the bosses they’ve had.
If you know the answer to this question, it’s much easier to align work that they will be excited about this year.
You’ll have people on your team that won’t know how to answer that question — that’s ok!
The point is to figure out who already knows how to answer this question. Those are the people that are thinking ahead, have goals, and are thinking more strategically about what they’re trying to accomplish at your firm and in their career.
What about the people that don’t know? That’s ok at this point, because you can step in and ask questions to help guide them toward an answer. Not sure what to ask? Try these:
Do you want to get more visibility?
This typically means more time spent with other teams, senior leadership, or in a wider audience (company town hall, internal face-to-face team meeting, etc.). Many people shy away from speaking opportunities, but if you know that’s a goal for them, you can help coach them up in small steps. First a team presentation, then a presentation to a larger team, then a small part in a visible briefing, etc.
Are you looking for a leadership position?
Some people will earnestly answer yes, but a decent percentage will answer yes because they’re looking for more compensation. That group thinks “managers must make more” (which isn’t always the case), so they’re looking for whatever they can to make more money. There’s nothing wrong with wanting to make more, but that should be a byproduct of being really good at leading a team to a winning outcome.
In either case, this lets you pivot to find them leadership opportunities throughout the year and see how they respond.
Did you want to spend more time with customers?
There’s lots of ways to spend more time with customers, even for the pure introverts on your team. There’s customer surveys, web site customer usage data, and overall feedback that people can look at to understand your customer better. You could send them to an industry conference to work a booth for a day, helping them understand the type of questions that are asked to the marketing team.
One warning: If you ask this question and then never bring it up again, you’ll lose trust faster than if you never asked. Write down their answer. Revisit it in on the quarter boundaries (March, June, and September).
If you can help them make it real, you’ll have gone a long way to distinguishing yourself as a manager because so few people put in this level of effort.
See you next week!
-Frank
