Management Tips | June 30, 2020

10 Check In Questions to Keep Your Team On Track Between Meetings

image representing 10 Check In Questions to Keep Your Team On Track Between Meetings

A growing company - or the sudden absence of an office - can make it difficult for a manager to keep a steady pulse on the health and performance of their team. Daily Stand-ups and status updates can tell the story during meetings but a good manager needs a process to collect and manage team sentiment between meetings.

At Strety, we call this process 'Check Ins'. Check-ins are recurring single-prompt questions managers and team leads ask to increase engagement and gain proactive insights. The right mix of questions will help surface issues and gauge the real-time health of their team between team and 1:1 meetings, effectively filling in all a manager's blind spots.

In their book Nine Lies About Work, Marcus Buckingham & Ashley Goodall say  “A team with low check-in frequency is a team with low intelligence. Data reveals checking in with your team members once a month (during meetings) is literally worse than useless. While team leaders who check-in once a week see a 13% increase in team engagement, those in check-in once a month see a 5 percent decrease in engagement. There’s also a 2.7x increase in retention that accompanies frequent conversations. As if team members are saying “I’d rather you not waste my time if all we’re going to do is talk in generalities”.

Check-ins are not one-sided.  You have to give to receive. The engagement boost only happens when team members regularly check in AND regularly get a reply. Buckingham & Goodall elevate this sentiment:  

“Checking in with each person on a team - listening, course correcting, adjusting, coaching, advising, paying attention to the intersection of the person and the real-world work - is not what you do in addition to the work of leading. This is the work of leading” 

The more frequent and predictable your check ins, the more real time attention you’ll be able to give to your team’s work, leading to more engagement and higher performance from your team. What we’re saying is: It Starts with You! 

Implementing Check Ins

We use check ins to keep our teams engaged and our managers informed; each one serving as its own asynchronous, one-question meeting.  Buckingham and Goodall simplify their approach by recommending managers start by asking each team member two simple questions each week:

  • What are your priorities this week
  • How can I help

It’s less about a perfectly posed question and more about consistency, and these two check ins are a great place to start. They’re simple and they put the focus on the actual work your team is doing. This allows managers to know where they can have the most impact right now.

Don’t expect your questions to be uncovering gold right away. You’ll have to find what works best for you and your team. Test, learn, iterate, repeat. Here are a few things to think about as you roll-out check ins:

  • Cadence: How often do you want to ask certain questions
  • Day of the week: Ask the check in when you’ll get the best answer
  • Public/Private: Do you want answers to be shared with the entire team or only with you

At Strety, our check ins are a healthy balance of daily, weekly, and monthly work and non-work related prompts. We’ve set up questions that ensure we have a holistic view of how our people are doing while also reinforcing our company’s values & culture. Here are some examples of questions we’ve had success with to help you get going:

Suggested Questions to Ask Your Team

Daily Check Ins

1. What are you working on today?

Ask in the morning, make public. This should be a short bulleted or numbered list of the key tasks each team member is working on today.  Not only does this show you what your team is prioritizing but it helps break down the barriers between departments. In providing visibility into what everyone else is working on, you allow each team member to see how their work contributes to the overall organizational effort

Daily check in

2. How was your day?

Ask in the afternoon, private or public. Perfect for new hires or people in new roles.  A great opportunity for your team members to reflect on hyper-specifics from their day and for a manager to provide a little hands-off guidance. It’s also a cross-referencing point with ‘What are you working on today?”

Weekly Check Ins

3. How are you feeling coming into this week?

Ask Monday morning. Can be open-ended or 1-10 scale. This is about understanding everyone’s headspace. Are they coming into the week refreshed and recharged or are they carrying stress? 

If the latter, it’s a great opportunity for you to help lighten their load and set the pace for a better week. Especially important for distributed team leaders since you don’t have that Monday morning visual like you would in the office.  

4. What challenges are you facing?

Ask this midweek.  Allows you to get ahead of any issue and to provide real-time course correction while the actual work is being done. Really push to get a response here. Maybe it isn’t directly related to the work they’re doing but to their work process; i.e. having trouble staying focused while working from home. You need to know these things, too!

5. What wins did you have this week?

Ask on Friday afternoon. Gives you an opportunity to recognize their work - especially the day-to-day things you may not be fully on top of. Also allows you to see where your team is placing value; what do they see as a win versus what you may see as a win? Take note of the types of work each member of your team is proud of.

6. How did you feel this week?

Ask on Friday afternoon.  This forces your direct report to slow down, reflect, and learn from the work they’ve accomplished. Seeing self-growth is empowering. We are BIG TIME believers in this practice.  It also gives you an opportunity to offer advice, guidance or reassurance at the end of a week reducing the likelihood any unnecessary stress gets carried into the next week

Strety Users: When a Check in response requires further discussion, easily add it to any upcoming meeting agenda

Weekly check in


Monthly Check Ins

7. What part of your role are you most passionate about? Feels the most draining?

This check in will give you quality insights to how your direct report feels about their work.  Does their purpose match up with the team and organizations?  Knowing what tasks sap the energy from their day is equally as vital.  

In collecting answers to these questions each month - rather than 1x/year during annual performance reviews - you’ll have the data points you need to really understand what’s motivating, driving, and/or hindering performance, helping them feel more fulfilled and perform higher year round.

8. Have you been inspired or extra motivated by anything or anyone recently?

Weekly or monthly prompt that encourages peer recognition.  Can also bring organization-wide visibility to silo’d work. Sources of inspiration and motivation can also come from outside work, i.e family, friends, communities, philanthropy.  We strongly encourage you to work this check in into your routine.

Culture Building Check Ins

9. What did you do this weekend?

We ask this every Monday morning. This is an opportunity to learn about the person behind the role. I can’t tell you how many cool things I’ve learned about my co-workers from their weekend updates; some are excellent cooks, some read A LOT, some can run 10 miles.  In the long run, this is the stuff that truly matters when building a cohesive team.  Sharing may not come natural to everyone, so lead by example and encourage everyone to share a few photos!

Culture building check in

10. If you were to recommend one ___ what would it be?

  • movie/youtube video to watch
  • album or podcast to listen to
  • book or blog to read 
  • Restaurant to eat at
  • Recipe to try 

People love sharing what they’re into! These more fun questions will help your team get to know one another and could build relationships between team members through common interests or shared experiences they’d perhaps never have found out otherwise. 


How someone is feeling and how they’re performing are almost always intrinsically connected, and having a consistent pulse on both sides of a person at all times, not just during meetings, is a vital part of your role.

Use these questions - or come up with you own - and you’ll be well on your way to better understanding your team, increasing engagement, and achieving better business outcomes.


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