Let's dispel a myth right at the start: Critical thinking doesn't involve being argumentative, disrespectful of leadership, or actually being critical. A quick Google search of "critical thinking" results in the following definition:
"The objective analysis and evaluation of an issue in order to form a judgment."
That's not the only definition available, but it seems to summarize the others fairly well. The idea here is to develop team members who aren't simply performing tasks as assigned, but who are also evaluating what's going on around them and offering new ideas or solutions to current issues.
As leaders, we shouldn't allow ourselves to feel threatened when a team member asks why we're doing something a certain way or if we've considered making a change. The fact that your team member is asking questions and offering ideas is a great sign. It shows how much this individual cares about your church and the people you're trying to serve.
With that myth out of the way, how do we develop critical thinking skills? Here are a few ideas:
#1 Read books together
Find books on ministry, leadership, church structure, time management, culture and society, and more. Select one book to read and discuss at staff meetings. Assign a few chapters to each staff member. Have them read those chapters ahead of the team, then develop and send out questions about those chapters ahead of the next staff meeting.
This provides each team member with the opportunity to lead the discussion and, by sending the questions out a few days in advance; everyone has a chance to think about the material before the meeting. You could cover a book per month or every other month, whatever works best for your team.
#2 Invite different viewpoints
When you're the point leader, most team members will tend to want to agree with you. They're looking to you for approval and affirmation. That means when you mention you're thinking about adding a new service on Sundays, they'll probably tell you that's a great idea (even if they're not so sure).
So, how do you handle that issue? Start off by saying you're thinking about adding a new service, but you're not sure yet and want their input. Then, if all you're hearing are all pros and no cons, bring one up to provoke a reaction. "Well, if we add another service we'll need to double our volunteer teams. What would it take to make that happen?"
Another way to handle it is to say, "Okay, this all sounds great but I don't want to do this without thinking through potential issues as well. What obstacles would we have to overcome to make this happen?"
Make sure they know it's okay to disagree behind closed doors. Once you've considered their input and made a decision, then it's time for everyone to support it once they leave the room. In the meantime, you want them to speak up if they disagree.
#3 Ask "why?"
Have you ever heard of the Five Whys? It's a simple technique to get someone to really think through a statement or opinion they've expressed.
Here's how it can work - Let's say you raise the idea of adding a couple's retreat in 2016:
Staff member: "We don't have the capacity to add another event this year."
Staff member: "Well, our volunteers are getting burned out."
Staff member: "Because the same volunteer leaders have served every weekend and several weeknights for the last three months."
Staff member: "Because we had several events in addition to services and our bench isn't very deep when it comes to volunteer leaders."
Staff member: "We don't have enough volunteers to cover each area, much less develop new leaders to move up."
Staff member: "We haven't focused on inviting more people to serve."
You: "So, we can't add another service because we haven't developed a strong volunteer culture. Okay, that helps us figure out what to work on next."
It can be a bit annoying when you're on the receiving end of this, but it really does help you to think critically and get to the root of the issue.
You need team members who'll go beyond getting stuff done. That's important, but you really see a team excel as they think critically, evaluate each situation, apply their faith, and work together to reach more people with the Gospel. Encourage your team to bring their ideas and questions to the table. You never know what great insights they'll offer unless you invite them to the conversation.