When it’s time for a check-in with your boss

LET’S face it, check-ins with your manager aren’t the most thrilling thing to look forward to. For an overthinker like me, check-ins can be quite anxiety-inducing, especially if my boss calls me into one unexpectedly and I can’t figure out why.

But instead of viewing them as a source of pressure, check-ins can actually help you make progress in your career if you play your cards right.

Knock, knock

Contrary to popular belief, check-ins with your manager don’t have to happen only in the middle or at the end of the year.

More organisations are leaning towards regular check-ins for the well-being of employees and employers.

These one-on-one sessions are useful for managers to gain insight into the way employees work, helping them understand their thought processes and what kinds of projects are best for them.

They can also help employees realign their priorities if they go off track, and address any instances of miscommunication by giving timely feedback before complications develop.

Here are some signs that a check-in could be in order:

• Lack of clarity in expectations of one’s overall job scope or specific aspects of work, often leading to poor performance or frequent miscommunication.
• Shifting priorities or workload demands that need to be discussed in order to smoothen workflows and agree on broader goals.
• Changes in personal circumstances that could affect your work (such as health issues or major family matters).

Overkill? A waste of time?

That being said, too many check-ins can be counterproductive, in the same way long, agenda-less meetings tend to be.

Some Gen Zs actually feel that check-ins can be a waste of time for both supervisors and staff, especially if communication between the parties is unclear or unconstructive.

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For Huifen (not her real name), 25, her boss at a preschool enrichment centre she used to teach at would do weekly check-ins with her. But she felt the ideas her boss suggested were impractical and vague, and did not help her perform better at her job.

“I didn’t feel like her weekly feedback improved my lesson plans in any way, or could have made any longstanding change to the work I was doing,” she said. “I felt many times that it wouldn’t have made a difference whether she checked in with me or not.”

Partnerships manager Beverly (not her real name), 25, said she has quarterly check-ins with her boss, but sometimes finds it difficult to get effective support as her boss manages several other departments amid limited resources.

“I’ve found that our check-ins are not helpful because my boss tends to prioritise more pressing needs of the overall company over my department, due to her limited bandwidth,” she said. “Her feedback was too general for me to work with at times.”

A checklist

So what do you do if your check-ins aren’t helping you? Or if you’re at the other end of this, how do you start a conversation with an ultra-busy boss to let him or her know you need more than the once-a-year performance assessment? Here’s what you could do:

• Flag clear challenges and roadblocks: It’s important to identify the main difficulties you’re experiencing in your work, and explain why you need help and more support or clarity from your supervisor. For example, if you feel that your boss’ current approach in managing you isn’t helpful, raise the issue respectfully. Also, enter the conversation prepared with potential solutions to resolve the problems at hand. If your boss is unable to check in with you more frequently, request alternatives to get the support you need. Are there other senior staff or mentors that you could consult, or online resources that can provide what you are seeking?
• Prepare key questions for your boss: Make a list of your burning questions or topics you’d like to discuss. This could include clarifications on certain projects, specific feedback, or an appeal for guidance on how to improve your performance and career prospects.
• Address any instances of miscommunication if needed: Don’t overlook this, especially when it comes to expectations on work deliverables; this is your best opportunity to fix these. 
• Make a list of your accomplishments and articulate them: Don’t forget to keep track of what you’ve achieved. You might have work struggles, but they shouldn’t overshadow any worthy contributions you’ve made so far. It’s important to be specific and highlight the impact of your work.
• Provide updates on your progress on projects: Even if your projects don’t have specific timelines or deadlines, make sure to update your boss on their status. Do also address any delays or changes you’ve had to make to the agreed-upon plan.
• Collect feedback: If you’ve received feedback from colleagues or clients, consider sharing these with your boss. It shows that you value input from others and are open to improvement.
• Review your overall goals and objectives: You and your boss can conclude the check-in by revisiting the wider goals and objectives both you and your team as a whole have set. Ensure you have a clear, final understanding of what you’re working on and what you’re trying to achieve.

Fundamentally, a check-in with your boss is a two-way communication opportunity. Being clear about what you need can reap benefits, as Beverly learnt.

“Recently, I told my boss that I would like more specific support, direction and feedback for my department, and she has done (this) more these days, which I appreciate,” she said.

While it is important to report your progress, a good check-in also can involve seeking guidance and feedback, and building a strong working relationship with your boss. 

By the way, active listening is extremely important during your chat.

Your one-on-one time isn’t just to rant about your problems at work, but also to listen to feedback, co-create ideas and ask any follow-up questions to improve your work.

This article first appeared in the Thrive newsletter. Thrive is The Business Times’ young audience initiative. Subscribe to Thrive at bt.sg/thrive. Do also follow Thrive on Instagram and TikTok.