How to Draw Out Challenges Weighing On Your Team

Posted in executive director / staff team / staff meeting

How to Draw Out Challenges Weighing On Your Team

A typical staff meeting can feel very productive, have a great conversation, but still not reveal the stressors a team is facing. The reluctance to speak up can vary with reasons from being unsure if a topic is appropriate, to feeling it won’t matter. But is does matter because a healthy staff team matters.

Rather than hoping the team will find a way to articulate underlying concerns about the job, use these questions to draw out the information in the safety of a collective conversation.

At the start of a staff meeting use these three simple questions before jumping into any other conversations. The questions focus on both the positive and the negative. Some team members will jump right in and tell you what’s failing. That’s great. But for those who aren’t brave enough to speak up, this provides a positive easy-out answer, but it still gets them thinking.

Start Question #1 – What’s the best news you’ve had since the last meeting?

This question gives the meeting a positive jumpstart. It also helps to understand the areas where a co-worker is feeling especially proud. While it is always nice to celebrate and support the wins of the team, it is even better to learn which win felt especially important to someone.

Start Question #2 – Right now, what’s working and/or not working for you?

This question helps the team take a tentative step into verbalizing an area where they are having troubles. Coupling it with the ‘what’s working’ piece, provides a way for someone to express concerns without feeling like they are being too negative, because they can pair it with something positive.

Start Question #3 – What are your expectations for the meeting?

Now we’re getting a little deeper into each person’s work environment. The first two questions primed the thought process and got people talking. While the responses for this question will focus more directly on the agenda for a meeting, they will allow an opportunity for a supervisor to get one step further into identifying areas of concern for the team.

Proceed through the rest of the meeting and just before the end, ask another set of three questions. With the details of the meeting fresh in everyone’s minds, this last set of questions can help to draw out challenges.

End Question #1 – Given everything we’ve discussed at the meeting, and everything that’s currently on your desk to administer, what is the biggest challenge you are facing right now?

I rely heavily on this question to draw out the red flag concerns. Because it happens so close to the end of the meeting, I still have the full team at the meeting if a group discussion is needed, and it gives me an opportunity to make immediate changes to work loads, or other matters, that are causing problems for my team. That helps my team leave a meeting feeling heard and go into the weeks ahead with less stress.

End Question #2 – What do you need to overcome this challenge?

This question is the set-up for the next question. The answer will usually identify the big and small fixes that a member of the team needs.

End Question #3 – What do you need from others (team, partners, supervisor) to succeed in the days ahead?

This question is an opportunity for co-workers to speak up and support each other. A strong team will usually recognize a co-worker’s need and offer support.

I’ve used these questions to catch challenges that might otherwise derail my team. I have been genuinely surprised by some of the answers but so grateful for the opportunity to address problems, make corrections right on the spot, and stop burn-out before it gets out of hand.

I wrap the meeting right after these end questions and always check that the meeting met the expectations identified right at the start. If something didn’t get addressed, its handled before everyone leaves.

If the wrap up comments are negative, then I know I have more follow up work to do and need to do a better job at future meetings. If the responses are positive, then I feel reassured my team is leaving the meeting a little less stressed than when they entered.

I have had a lot of success with these questions, and they have been part of my team meetings for years. It isn’t necessary to formally add them to a staff meeting agenda in order to take them for a test run. When I first started, I told my team I had a few question to ask them, and then jumped in. I hope you will give them a go at your next team meeting.

If you try out these questions, I’d love to hear how it worked for you. Please use the handy little form on the right side of the page to let me know.


Hi, I'm Christie Saas, former board member, current Executive Director, and non-profit volunteer. I remember well, those early years when I lacked the training, the confidence, and the work-life balance to focus on becoming the best non-profit leader I could be.

Fast-forward past many bumps in the road, lessons learned, and you’ll find me still in the trenches, but a little wiser, a little calmer, and a whole lot happier. I love my work and I want to help you love yours too.

I created so non-profit leaders never need to feel alone. I’m here to help. If you’re a brand-new non-profit leader, or a little more seasoned, someone who’s looking to make a meaningful contribution and still have time for a full life away from the job, you’re in the right place.

© Christie Saas 2023 All Rights Reserved

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