Meetings | April 14, 2020

Questions to Ask for Magic One-on-One Meetings

image representing Questions to Ask for Magic One-on-One Meetings

One-on-one (1:1) meetings are an opportunity to discuss real-time performance, your career development opportunities, and to receive feedback and coaching from your manager.  It’s also a way for you and your boss to build or strengthen your professional relationship.  

Your one on one is one of the few moments where you, the direct report, are the main subject of the meeting.  The responsibility to bring relevant issues to the table and to make these an effective use of your time rests squarely on your shoulders. If you remain passive and allow your boss to drive the agenda, it’s unlikely all your needs will be met.

“So, what do you want to talk about?” is the last thing you ever want to be asked during a one on one meeting. If you’re not invested in yourself and your performance, how can you expect your manager to be? If there was ever a time to selfishly prepare, it’s for your 1:1s…

Own the Agenda

To hammer this home: Effective 1:1s happen when you determine what you want to discuss. This is your one-on-one. Own the agenda! Throughout your week and between meetings, write down topics for discussion as they come to you. Potential topics include:

  • Career development
  • Personal growth and self improvement
  • Suggestions for team improvement
  • Communicating your contributions
  • Aligning priorities
  • Personal issues that could impact work performance
  • Interpersonal issues with coworkers (the good and bad)

By the time your next 1:1 rolls around you should have a formidable list of topics to choose from. From there you should prioritize your list, create an agenda, and share it with your manager a couple days before meeting; giving your manager an opportunity to prepare and add their own topics.

Strety Users: Our meeting agendas are collaborative. Leverage the agenda as an active list of topic ideas. This gives your manager an opportunity to offer guidance and advance the conversation within the comment thread, leading to more dialed-in discussion during the actual meeting.


12 Questions to Ask Your Manager

So now you have a rough outline of what to do - what about actionables? I don’t want to provide you a list of uninspired suggestions or contextless questions to ask your manager; you can find those anywhere. I’d like to share with you a list of malleable starting points, with context, that you can bank-up and pull-out whenever you need more from your 1:1s…

Team & Organizational Alignment

1. What’s holding our team back from accomplishing [x] ?

Identify the main problem or bottleneck in your team’s performance and get a better sense as to what management thinks will help overcome it.  Gaining insight to how management looks to solve performance issues is valuable knowledge for you to possess.

2. What is one thing I can do to help improve our team’s performance?

The exhibits your commitment to the team or organizational effort and can segue into a discussion about your own skill set.

3. What’s one thing you think we should stop doing?

Knowing which processes or projects that are failing to produce is valuable intel. You can re-prioritize your workload and/or see it as an opportunity to help improve inefficiencies.

4. What factors led to us deciding [x]?

You may not feel comfortable or be in a position to dig too deep as to why certain decisions are made but if you disagree with a decision or want to better understand why your team went a certain direction, it’s important to ask your superior.  Conversely, maybe you simply want insights to what goes into a decision making process within positions you aspire to be in one day. Both are perfectly valid and insightful reasons to ask for more.

Professional Growth

5. Do you have any recommendations for how I can improve [x] ?

This question is about you and specific skill development. Managers have experience and connections and this is your opportunity to leverage those resources. Ask for recommendations for educational courses, training programs, reading material, or to make introductions to people in their network that can offer additional insights. 

6. What do you see as gaps in my skill set?

Learning where you have holes - or perceived holes - is critical knowledge for you to possess.  You can either acquire the skill or, if it’s only a perceived gap, begin to more visibly show it off. Don’t run from this question. Ask it. Learn from it. Grow because of it! 

7. How do you see my role evolving over the next 12 months?

You have your own ideas for what you want to accomplish - find out where your manager sees you going. Are your visions for you in alignment? If not, you have a lot to talk about in your next 1:1…

8. What can I be doing now to put me in a position to be [x] in [y] time?

Talk to your manager about where you want to go professionally. This does not have to be specific to the opportunities available within your current organization. These are your long-term professional goals. Have them help you lay out the steps, short and long term, to achieve your goals. DO NOT let your annual review be the only time you talk about your career aspirations.

Strety Users:  Make this a recurring meeting agenda item so that this remains at the forefront of your 1:1 Meetings.  Use action items to hold you and your manager accountable for any to-dos (make a professional introduction, sign up for a training  course, etc) that come from your discussion.

Building Professional Rapport

9. What do you want to know about my work?

Have empathy for your managers. It’s difficult for managers, especially first-time managers and managers of larger teams, to track the daily activity of each of their direct reports.  In asking this question, you’re being proactive in helping them fill-in their blind spots while giving you the opportunity to expound on work - progress & successes - that could be going unnoticed. Managers will appreciate this.

10. How would you like to receive information/deliverables from me?

Every organization has a process and structure for how information is disseminated, but each manager likely has their own personal preference for how they receive info, feedback, updates, or questions. Learn their style. Adapting your deliverables to fit their personal preferences will make their job a little easier and is a simple yet effective way to build rapport.

11. What wins do you need?

1:1s are a two-way street. Don’t shy away about asking your manager about their job. Their focus affects you directly or indirectly.  Learning what a manager’s priorities are is another valuable insight. It can also help you frame your work around larger team or organizational objectives.

12, If I need something, what’s the best way to ask for your input?

All managers manage and provide feedback differently. Learning how and where they feel most comfortable providing support - over email, in person, screen share - will increase the likelihood you get the help you need

We're Here to Help

Whether you can use these questions verbatim or if they need some refinement to fit your situation, I hope you leave this post seeing your one-on-one meeting as a huge opportunity...not just another meeting. 

Remember: You’re in control of this one!. Be mindful and take your preparation seriously and you’ll leave each meeting better than when you entered it… if only we could say that about all our meetings :)



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