Transform Catch-Up Meetings By Asking These Unconventional Questions

Cath up meeting informal gathering, virtual meetings

Meetings can be challenging to manage. Done right, they'll inspire your team, stimulate ideas, and keep your organization on course. Done wrong, they risk killing employee morale, causing confusion, or undermining your leadership. 

The stakes are especially acute in catch-up meetings with individual employees. A successful catch-up meeting can unlock a team member's potential, review progress, and bring critical issues to the surface.

But, despite your best intentions, catch-up meetings can just as easily fall flat. They can spawn awkward silences, come across as formulaic exercises or, at worst, infringe on busy schedules while gratuitously reinforcing workplace hierarchies.   

An experienced team leader knows that the key to effective catch-up meetings is to focus on more than simply asking "How are things going?".

Posing unconventional questions can improve the tenor of a catch-up meeting, form connections, elicit revealing responses from your team members, and cultivate engaging discussion about best practices, upcoming tasks, and recent events.

It also prompts valuable feedback, builds good relationships, improves the work environment, and enhances your team's job performance.

Here's an overview of how to use thought-provoking questions in catch-up meetings with your team members. 

The Role of Questions in Meetings

Questions play an essential role in any successful meeting with your team members. They create dialogue and generate new ideas. And they foster collaboration, which is the principal benefit of assembling your team in person or on video calls.

When team members voice complaints about too many meetings, it's usually because you fail to manage regular meetings effectively through well-crafted questioning. A meeting without questions becomes a lecture you could accomplish more efficiently by email or in a digital workspace.

Employees attending question-less meetings tune out or ask themselves, "Why do I need to be here?" It's a recipe for frustration and a squandered opportunity to set clear objectives and gain essential feedback. 

Moving Beyond the Basics

But all questions are not created equal, especially when posed in a catch-up meeting. Too often, catch-up meeting questions lead to small talk. Managers following the usual meeting agenda template ask bland questions like "How are you doing?" and employees respond in similar vagaries. The meeting cadence resembles a chance meeting between acquaintances at a cocktail party, lacking a clear agenda and key points. 

To take full advantage of a catch-up meeting, managers must instead craft creative, thought-provoking questions with a clear objective and agenda in mind. Ideally, every question should discuss relevant information, be it the substance of the employee's responses or how they're offered.

Questions should also be open-ended rather than inviting a yes/no or pre-defined answer.  If successful, by asking these questions in informal face-to-face interactions the manager will attain useful data and the employee will feel heard and respected.  

To that end, questions posed in a catch-up meeting should also account for interpersonal dynamics and the power asymmetry between a supervisor and a subordinate. A good question reinforces conditions that lead to open discussion and invites team members to give clear, truthful, candid responses. The questions you ask in your next meeting should validate team members and set them at ease, not make them feel uncomfortable, attacked, or pressured to give a certain answer. 

Unconventional Questions for Catch-Up Meetings


With those principles in mind, here are some suggestions for provocative, unconventional questions designed to go beyond the standard meeting agenda template of informal catch-up meetings.  

Questions to Understand Individual Perspectives

Skilful managers appreciate that team members' personal lives and individual perspectives can shape their approach to problem-solving, collaboration, and setting long-term goals Asking these questions in your next catch-up meeting can evoke answers that enrich that understanding. 

  • We're introducing [new product/service/workflow] soon. How do you think it will be received?

  • What do you think our customers think of us?

  • What's something new hires should know about working here that you didn't know when you started?  

  • Which internal processes work well/need improvement right now?

When asking questions, emphasise that there are no "wrong" answers in a catch-up meeting. Make clear you want the employee's feedback and trust its potential to support the team's mission. 

Questions to Elicit Creative Thinking

Your employees can be a near-limitless source of creative ideas and inspiration if you give them a chance to express themselves and show that you value their contributions. Pose these questions in a catch-up meeting to tap into that rich vein of creativity. 

  • What could our organisation be the best at?

  • Aside from increasing pay, what change would instantly make this a better place to work?

  • What should we be telling our customers more about?

  • What's the most obvious way the business/organisation wastes its resources?

Keep creativity-inspiring questions open-ended and light-hearted in a catch-up meeting. If they trigger laughter, you're on the right track. 

Questions to Promote Team Bonding

As a manager, you strive to build cohesive teams of individuals who excel at their job duties, respect each other, and take pride in their collective effort. Here are some questions to ask teams in catch-up meetings that promote those goals.

  • Which of your coworkers impresses you most?

  • What are our team's biggest strengths?

  • If our team had a slogan, what would it be?

  • What support could our team most use right now?

Keep team bonding questions positive, even if you hope to elicit constructive criticism or discuss potential issues and concerns. You're far more likely to create candid conversation in a catch-up meeting if ask someone to praise their team members rather than to critique them. 

Questions to Gauge Job Satisfaction and Motivation


A common agenda item of a catch-up meeting is discussion of your subordinate's job satisfaction and motivation to succeed. Ask these questions your next meeting to reveal how your teams feel about their work duties and career progress. 

  • What's your ideal job or specific project?

  • How can I support your development or work goals?

  • What do you find most satisfying/challenging about your job?

  • Who's career/job progression — inside or outside the organisation — do you admire?

Remember that not all subordinates necessarily want a career in your industry, so answering these questions in a one-on-one catch-up meeting can feel fraught. If possible, reassure them you support their progress, regardless of their future career path. Employees feel valued and perform at peak level when they believe you take genuine interest in their well-being, success, and long-term goals, wherever they lie. 

Questions to Uncover Hidden Challenges

Catch-up meetings can also reveal vital information about your team's concerns and difficulties. Ask these questions in one-on-one meetings to learn about hidden challenges and how to address issues before they progress. 

  • What's something that you find unusual or difficult to understand about the organisation?

  • What challenges have you encountered that seem avoidable but beyond your control?

  • Which area appears most in need of improvement?

  • What project/initiative/product line would you change or do away with, if you could?

You can never know where questions about hidden challenges might lead until you've asked them. But they can yield most insightful and pressing responses you hear in a catch-up meeting. 

Implementing Unconventional Questions in a Catch-up Meeting

As mentioned, asking unconventional questions takes attention to the dynamics of a catch-up meeting. It can catch your subordinates off-guard and put them on the defensive if you dive straight in or seem wedded to a strict agenda.

To ensure your employee receives unconventional questions with an open mind and responds to them with candour, consider prefacing the conversation with a little context. Discuss why you've chosen to depart from the usual talking points and standard catch-up meeting agenda template. Openness encourages team members to relax and piques their interest in what the meeting agenda has in store. 

In asking unconventional questions, remember that you stand a good chance of your direct reports giving feedback containing real substance and more detail than usual. Spurring your team to speak freely in meetings, after all, is the point of the exercise.

How you discuss feedback from a team member in catch-up meetings matters. Receive feedback in a non-judgmental manner. Answer questions posed back to you with as much frankness as possible. Demonstrate your engagement with your employee's point of view and emotional state by asking follow-up questions that maintain a positive meeting cadence, maintaining eye contact, and giving your undivided attention throughout the meeting.

If the catch-up meeting spawns action items or open questions, get on the same page with your team member about how to address the most important points as the final step in the meeting.

By weaving unconventional questions into your regular catch-up meetings, you can transform previously staid and formulaic conversations into an open discussion that boosts the morale, progress, and job satisfaction of your whole team. In the process, you can gain valuable insight into your organization, including its assets, challenges, action items, and best practices. 

Employee scheduling and Time-tracking software!
Employee scheduling and Time-tracking software!
  • Easy Employee scheduling
  • Clear time-tracking
  • Simple absence management
Try for free Request a demo

Revolutionize Your Catch Up Meetings with Shiftbase

Transitioning to the art of thought-provoking questions in your catch-up meetings is a step towards more productive conversations and unlocking your team's potential. To further amplify this efficiency, consider integrating a powerful workforce management tool like Shiftbase into your operations. Shiftbase offers intuitive employee scheduling, comprehensive time tracking, and streamlined absence management to further transform your work environment. Whether it's creating balanced work schedules, tracking hours, or managing leaves, Shiftbase provides solutions to efficiently handle these tasks, giving you more time to focus on engaging with your team in your catch-up meetings.

Ready to revolutionize your workforce management? Try Shiftbase for free for 14 days and experience the difference yourself.

Topic: Communication / Catch-up Meeting