THRIVE NEWSLETTER

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

Chloe Lim
Published Thu, Sep 14, 2023 · 05:10 PM

🚪 Knock, knock

Contrary to popular belief, check-ins with your manager don’t have to happen only in the middle or end of the year. More organisations are leaning towards more regular check-ins for the well-being of employees and employers. 

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

These sessions can also help employees re-align 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?

There’s such a thing as too many check-ins at work. Similar to larger meetings that run over time or lack a proper agenda, excessive check-ins can be counterproductive, aimless and leave everyone involved more confused than before.

We hope neither you or your boss say this to each other at your check-in.

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

Huifen* (not her real name), 25, a former teacher at a preschool enrichment centre, told Thrive that her ex-boss would have weekly check-ins with her. However, she felt that the ideas her boss suggested were impractical and vague, and did not have an impact on her work performance.  

“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 shared. “I felt many times that it wouldn’t have made a difference whether she checked in with me or not.” 

As for Beverly* (not her real name), 25, the partnerships manager at a Singapore-based non-profit organisation has quarterly check-ins with her boss. However, as her boss manages several other departments amid limited resources, she sometimes finds it difficult to get effective support.

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

📜 Checklist for your next check-in

So what happens when your current check-ins aren’t doing you any good? Or for some, how do you start a conversation with an ultra-busy boss to indicate that you might need more than just an end-of-year check-in? Here is what you could do:

  • Flag clear challenges and roadblocks: It’s important to identify the main difficulties you’ve experienced in your job thus far 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, you should address the issue respectfully. Be prepared to offer potential solutions to resolve the problems at hand. If your boss is still unable to check-in with you more frequently, ask for possible alternatives to get the support you need. For example, are there other senior staff or mentors that you could consult?

  • Prepare key questions for your boss: Develop a list of your burning questions or topics you’d like to discuss. This could include clarifications on certain projects, specific feedback, or guidance on how to better improve your performance and help your career prospects.

  • Address any instances of miscommunication if need be: This should not be looked over, especially when it comes to expectations on work deliverables. If there’s any time to fix this, it would be during the check-in. 

  • Make a list of your accomplishments and articulate your current progress: Don’t forget to (humbly) share what you’ve done well so far at your job as well. You might have work struggles, but they shouldn’t overshadow any worthy contributions you’ve made so far too. It’s important to be specific and highlight the impact of your work too.

  • Update on relevant timelines: If your projects have specific timelines or deadlines, make sure to update your boss on their status. Be sure to address any delays or changes to the schedule.

  • Collect feedback: If you’ve received feedback from colleagues or clients, consider sharing this feedback with your boss. It shows that you value input from others and are open to improvement as well. 

  • Review your overall goals and objectives: You and your boss can conclude the check-in by revisiting the wider goals and objectives for yourself and the team. 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 found out.

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

While it is important to report your progress, it’s also about seeking guidance, feedback, and building a strong working relationship with your boss. This means that active listening is extremely important during the check-in. 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. 

TL;DR

  • Check-ins don’t just have to be at the middle or the end of the year. Rather, they can be held more regularly to improve the well-being of employees and employers. 

  • Too many check-ins can end up wasting time, especially if they are badly planned. 👎

  • Remember to address key issues and raise any important questions you might have to your boss during your check-in. 

  • Don’t just rant about your problems. This isn’t a one-way communication street for you! 😤

  • Listen actively to any feedback your boss has for you and respond with follow-up questions on how you can improve further. 👍

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