Career Conversations Good Bosses Have With Their Employees Regularly

Look, I get it, nobody is perfect, and even the best managers struggle to be “on” all the time when it comes to being the best boss ever.

But one of the easiest ways to instantly improve your relationship with your own direct reports (and your overall team morale) is through communication—simple, I know.

But trust me, as someone on the other end of this communication (or lack thereof), making an effort can be the difference between a hard-working and engaged superstar and someone who’s just collecting a paycheck.

You can improve your own communication by having these seven conversations with your direct reports every week, month, and  quarter:

Every week;

Whether you have formal check-ins or informal meetings throughout the week with your employees, make sure you’re asking the following:

1. “How Are You?”

This should probably fall under the “every day” category, but for the sake of reality and busy schedules let’s say you do this at least once a week.

Make sure you’re not just asking your employees how they’re doing but actually expressing interest in their reponse. This means reading between the lines and understanding when something bigger is simmering below the surface of their answer. It means asking follow-up questions if something feels off (or even just when something feels important to the person, like a good friend visiting for the weekend). And it means getting to know what else is going on in their life that may or may not be affecting their work.

2. “How Can I Help?”

Delegating and knowing when to step aside are parts of being a good boss, but that doesn’t mean you leave your employees in the dust to fend for themselves. Make sure you’re checking in to see if they need assistance or even just an ear to bounce something off of—especially since they may be afraid to ask for it.

This goes double for any manager who’s always in meetings or sits far away from their team. Whether you mean it or not, this lack of a presence can translate into “I don’t care” or “I don’t have time for your problems.”

Just asking this question can help make sure that’s not the message your team is getting.

Every month;

Once a month (at least), you should be addressing these important topics to ensure your direct reports are on the right track:

3. “This Is What I Want You to Prioritize…”

Goals shift, strategies change, and its likely when they do your employees will struggle to know what to focus their energies on. When this happens, don’t just explain why it’s happening but also how it’ll affect each individual and whether they need to reorganize their schedule, responsibilities, or priorities.

4. “This Is the Area Where I’d Like to See Growth in the Next Month…”

Giving feedback on an ongoing basis is crucialfor your employees to continue growing and producing great work. If you’re doing it weekly or even daily that’s awesome, but it’s perfectly fine to take time once a month to go over any recurring issues or larger mistakes they may be making. Just make sure to follow up any feedback with clear improvement metrics and a timeline so it feels achievable.

Also, note, this is a great time to give positive feedback, too!

5. “What Can I Do to Help You Reach Your Goals?”

The best managers know that they can be your biggest advocate, but also your biggest blocker. So by asking this question, you can ensure you’re not accidentally standing in the way.

Every quarter;

These questions are about your employees’ trajectories—if you address these quarterly, you’re more likely to retain high performers and build a stronger, happier team.

6. “What Are Your Long-Term Goals?”

Get a sense of where they want to be in three months, six months, a year from now. You may be surprised to find they want to pick up projects that you really need done. Or, you may discover a hidden passion you didn’t know they had. Or, you might realize their recent mediocre performance is due to working on things they aren’t excited about. Understanding all this will help you hone in on their strengths and encourage them to produce their best work.

7. “What Skills Would You Like to Build/Continue to Build?”

Similar to above, this narrows down what they are and aren’t comfortable with within their skill set. This can help you figure out what training they may need or what assignments they need to take on to improve.

While it looks like this is set in stone, there’s no hard or fast rule for how frequently you have these conversations. Maybe you want to give feedback more often, or you think it’s key to review long-term goals once a month—that’s cool, too.

Just make sure you’re actually having these discussions. Trust me, they’ll make your job easier and your team that much more successful.

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