Confront challenging problems with creative solutions.


Make the best possible decisions in order to achieve objectives.


  • Assignment 1 // Read Matthew 22:15-22 and answer questions.

  • Assignment 2 // Watch “Dan Heath: Being Decisive” and answer questions; read book Decisive by Chip and Dan Heath.

  • Assignment 3 // Read “Widen Your Options” and answer questions.

  • Assignment 4 // Read “Reality Test Your Assumptions” and answer questions.

  • Assignment 5 // Read “Attain Distance Before Deciding” and answer questions.

  • Assignment 6 // Read “Prepare to Be Wrong” and answer questions.


Matthew 22:15-17 (ESV)

Then the Pharisees went and plotted how to entangle him [Jesus] in his words. And they sent their disciples to him, along with the Herodians, saying, “Teacher, we know that you are true and teach the way of God truthfully, and you do not care about anyone's opinion, for you are not swayed by appearances. Tell us, then, what you think. Is it lawful to pay taxes to Caesar, or not?”

There’s a little background needed to truly understand what is going on in this story. The Pharisees are a hyper-legalistic religious group. They don’t like Jesus because he teaches that following the letter of the law is less important than doing things with the right heart. They’re always trying to trip-up and trap Jesus.

Here they ask him if the Jews should pay taxes to Rome. Now, the Roman Empire was an occupying force. It was like the British Empire in America in 1776, only worse. So if Jesus says “Yes, pay taxes to Caesar,” the Jewish people will hate him because he supports the rulers who are subjugating them. But if he says "No, don’t pay taxes to Caesar," he risks bringing the wrath of the Roman Empire down on his head. Quite the quandary, isn’t it?

However, Jesus offers an imminently wise and incredibly subversive answer.

Matthew 22:15-17 (ESV)

But Jesus, aware of their malice, said, “Why put me to the test, you hypocrites? Show me the coin for the tax.” And they brought him a denarius. And Jesus said to them, “Whose likeness and inscription is this?”

They said, “Caesar's.”

Then he said to them, “Therefore render to Caesar the things that are Caesar's, and to God the things that are God's.” When they heard it, they marveled. And they left him and went away.

Often this passage of Scripture gets taught as an admonition to pay your taxes. That’s probably a good lesson to take from this, but there’s something more important going on here.

In the Roman world, there was nothing that was not subject to the rule and reign of Caesar. Nothing was outside of his purview, nothing beyond his reach. He was even worshipped as a god.

Jesus, with the simple turn of a phrase, establishes that there are things over which Caesar has no control, that there is a greater king and another kingdom where God, not Caesar, reigns.

Jesus refuses to choose simply “Yes or no.” Instead of being backed into a corner he manages to avoid the wrath of both the Jews and the Romans while at the same time declaring God’s power.


  1. When is a time you felt stuck between two bad options? What did you do and how did things turn out? Looking back, is there something you would have or could have done differently to achieve a better result?


In their book, Decisive , Chip and Dan Heath describe a four-part process for better decision making: WRAP.

  • W iden your options

  • R eality-test your assumptions

  • A ttain distance before deciding

  • P repare to be wrong

WRAP gives us a framework for approaching problems that are particularly sticky. You don’t want to use it every time you need to make a decision, but when a decision provides a big opportunity, has the potential to go really wrong, or is just plain difficult to figure out, WRAP will increase our chances of making a better decision and limit the downside when we make the wrong decision.


  1. What is one difficult problem or decision you are facing right now that you would like to analyze further? Ideally, this would be some kind of leadership or strategy decision, but it could also be a personal decision.


Widen Your Options

The first step in the WRAP process is to widen your options. It’s easy to get stuck doing things the way we’ve always done them or to limit our options to simply “yes or no.”

Widening your options is what Jesus did so successfully in the passage we read above. When faced with a simple yes/no question, “Should we pay taxes to Caesar?” he refused to get backed into a corner. He found another option.

Let’s say you are considering asking your coaches to host a monthly huddle for their leaders, so you make a pro/con list:


  • Team building

  • Effective information-sharing

  • Accountability

  • Training

  • Leadership development


  • Time demands on leaders.

  • Inability to find a time/location that works for everyone

  • Different leaders have different training needs

Well, it looks like the pros outweigh the cons, so you do it, right? Maybe, but what if there are better options? Is a monthly meeting really the most effective team builder? What if they did a fun outing for team building once a quarter? And could accountability and information-sharing happen even more effectively in a brief weekly conference call? And what if you developed online video training modules for your leaders and then made individualized recommendations on which modules to complete, based on where a leader needs to grow?

Here are a few tips for helping you widen your options.

Avoid a Narrow Frame

Force yourself to consider additional options. Think through what other solutions there might be to the decision or problem you are facing. There are two techniques that can help you brainstorm additional possibilities.

Be aware of the opportunity cost . If you’re trying to decide whether or not to take a vacation, consider what else you could do with the $1000 you’d spend and the vacation time you’d use. If you’re trying to decide whether or not to start monthly huddles, consider what else your coaches are (or could be) doing with leaders that they won’t be able to do if you have the huddles.

Run the Vanishing Options Test . Assume that you cannot make the choice you are considering, what would you do then? If you could not have monthly coaching huddles, how would you ask coaches to invest in leaders?


Rather than considering ideas one at a time, test out several ideas at once. There’s nothing stopping you from developing one online training module that you think would benefit your leaders, asking one of your coaches to plan a team-building activity for their leaders, and asking another of your coaches to try out a weekly or monthly conference call with their leaders.

You might do that and decide that the conference call doesn’t work but that the team-building activity and training do, and so you land with doing one team-building activity and one business meeting per quarter. So you’re at almost-monthly get togethers, but you were actually able to do training and team-building more effectively while saving everyone from that third meeting per quarter.


What about when you’re struggling to come up with new ideas? You don’t know if you should implement a monthly huddle, but you’re not sure what else to do to accomplish your objectives.

Try to find someone else who has faced a similar problem.

Start locally. If there are other directors in your ministry, see what they’re doing. Is this a problem they’ve already solved? Or if they’re still struggling, are there things they’ve tried that didn’t work that will save you from making the same mistakes?

If looking locally doesn’t seem to generate helpful ideas, begin looking regionally. Are there directors in other ministries who have faced a similar problem? Their teams might be structured differently, so their solutions may or may not fit, but they might have some great ideas or practices that you can adapt. You might also look to directors in the same ministry at other churches. Again, those churches will have different visions and priorities, but there will certainly be some crossover between what another church is trying to do with kids’ ministry and what Eastside is trying to do with kids’ ministry.

And finally, if neither local nor regional outreach seems to generate solutions, look globally. Are there leaders in business or non-profits who have tried to solve a similar problem? Have the Boy Scouts figured out how to effectively communicate, build teams, and train their volunteers? Have corporations with large numbers of remote employees figured out how to keep everyone engaged?


  1. What are some alternative options to the ones you are currently considering for the decision from Assignment 2, Question 1?

  2. How can you implement multitrack testing of 2-4 of those options?

  3. Before you begin testing, who is someone you can reach out to for some coaching?


Reality-Test Your Assumptions

The questions in Assignments 2 and 3 were designed to help you widen your perspective and consider other options. The remaining assignments assume that you have found one of these options especially promising. Ideally, you would complete the remainder of this module after having gotten an outside perspective on your ideas and having had the time to do some multitrack testing to see which option seems to be the most successful. However, if you do not have time to begin actually implementing this process, you can simply select one option to move forward with for the sake of this exercise.

We all like our own ideas. You can have an idea pop into your head during a meeting, propose it, and be given three solid reasons why it won’t work. There’s a decent chance you’d still be thinking to yourself, “But it could work if we just did x, y, and z…”

You only had that idea 90 seconds ago. You spent no time developing it, and yet you feel defensive and protective of your idea. And maybe it is a great idea, or maybe not. If we want to figure that out, we need to find a way to be a bit more objective, to reality-test our assumptions.

Consider the Opposite

Consider the reasons your idea could be wrong.

Why might it be a terrible idea to have monthly coaching huddles? It takes up time leaders could spend investing in their team or group members. No one likes meetings. It’s going to be nearly impossible to schedule a time that works for everyone.

Part of considering the opposite is to invite disconfirming opinions. You need to make sure that you create an environment where disagreement is welcomed. If a team member disagrees with your perspective, does he or she feel free to speak up, or have you created an environment where it’s not ok to disagree with you? Have you brought people onto your team who think differently than you so that you actually get disagreement?

Of course, once you’ve found a disagreement, you have to work through it. One way to do this is to ask, “What would have to be true for this option to be the right answer?”

So if you’re considering monthly huddles, one of the things that would have to be true is that there is a meeting time and location that works for most of the leaders assigned to each coach. Another thing that would have to be true is that you have enough content (trainings, decisions that need to be discussed, feedback that needs to be received, etc.) to make the meeting worthwhile. If either of those things aren’t true, then a monthly huddle likely isn’t the right answer.

Another way of considering the opposite is to ask disconfirming questions. Ask questions that might undermine or disconfirm a statement or assumption. The best disconfirming questions are direct and specific. If you’re interviewing for a job and you ask, “What’s the work-life balance like in this organization?” you’ll likely get told that it’s good. But if you ask how many times in the last week the interviewer was home in time to eat dinner with his or her family, you’ll get a truer picture of what life is like at that company.

However, one time when you want to ask open-ended questions rather than direct and specific ones is when there is a power imbalance in the relationship. If you’re someone’s boss and you ask, “How do you like the way I just reorganized our team?” it’s tough for your employee to say, “I actually don’t like it very much!” Your question implies that you’re fishing for a compliment. However, if you say, “I’d like your feedback on our team’s reorganization, both what is working well and what has been a challenge,” you’re a lot more likely to get an honest (and thus useful) answer.

And finally, when considering the opposite, consider making a deliberate mistake. Take something that’s accepted wisdom. Maybe you “know” that people are busy and don’t want to attend team-building activities. And then do the opposite. Plan a team-building activity anyway and see what happens. If no one comes or they’re not enthusiastic, then you were right, and there’s very little lost from a single failed activity. But if it’s a smashing success, you’ve now found a new way to appreciate your team and keep them engaged.

Zoom Out

Zooming out involves making an honest evaluation of your idea based on actual experiences. Let’s say you’re considering going back to school to get a PhD so you can make more money. Have you looked at any data that shows how much more money people in your field make if they have a PhD? The difference might be negligible, and you may never recoup the money spent on your education.

There may be other personal or professional reasons to get a PhD, but if the decision is financially driven, pay attention to the data. You trust the data when picking a restaurant: if a restaurant has 500 Yelp reviews and is two stars, you’re probably not going to go there. If you trust the data when picking a $10 meal, why would you ignore it when making major life decisions?

It can be difficult to find hard data on things like the effectiveness of monthly coaching huddles. But you can find an expert to talk to. Note than an expert in this case is simply someone who has already tried what you want to try. Ask the expert what his or her experience was. If you talk to three experts and it worked well for all of them, chances are it will work well for you. If it failed for all of them, it will probably fail for you, too.

Zoom In

At the same time that you’re zooming out, you also need to zoom in to examine the specific situation or decision to see if there are any characteristics that make your situation different from the data.

You’re considering a monthly coaching huddle, and all three experts tell you that their attempts have failed because leaders just weren’t committed to coming. But what if a lot of your leaders are stay-at-home moms whose kids are in school and several of them have mentioned to you that they’re lonely and need to get out of the house more?

Now you have a data point, not just a gut feeling, that tells you that there’s something that might be objectively different about your situation when compared to the experts.

Note that it’s difficult to “zoom in” if you’re not in the trenches. If you’re a director in the small group ministry who hasn’t led a group in years or doesn’t engage with leaders directly because only your coaches do that, you’ll likely miss the detail and nuance required to zoom in. The fact that a leader is a stay-at-home mom is a pretty small data point. Your coaches may have never mentioned that to you. If you hadn’t interacted with the leaders directly, you probably would have missed it.


To ooch is to try an idea out before fully committing. Often leaders and organizations try to figure out what the best solution to a problem is and then commit. But what if you could get real-world data before committing?

Instead of telling all of your coaches that they now need to lead monthly huddles and announcing to all of your leaders this is the new regime, what if you simply asked one coach to lead a monthly huddle with their leaders for six months? Then you could evaluate whether or not it is a good idea. Plus, if it is a good idea, you can make some tweaks to make it better before rolling it out on a large scale.

By ooching , you’re able to test an idea out to see how well it will work before you put a huge amount of resources behind it. In this scenario, if coaching huddles don’t work out, you’re not left with a bunch of leaders that didn’t want to do them who are frustrated that you tried to make them and some leaders who did want the huddles who are frustrated that they didn’t go well.


  1. What can you do to force yourself to consider the opposite in the aforementioned decision?

  2. What does zooming out tell you about the decision you are making? (You may need to consult an expert or look up some data.) What about zooming in?

  3. How can you ooch your proposed solution so that you have an idea of its effectiveness before committing to it?


Attain Distance Before Deciding

Often, when you’re going through the decision-making process, there’s an option or a decision that clearly becomes the right one. There’s no question. However, when that doesn’t happen, when you’re left with two or more good options, it can be helpful to attain distance before deciding. We’ll sometimes find ourselves waffling on a daily or even an hourly basis between multiple decisions.

Overcome Short-Term Emotion

The way we feel about a decision in the moment can be our worst enemy. We make decisions in the grip of fear, anger, lust, pride, or anxiety, and those emotions usually result from what’s happening right now, in the moment. But the thing that would be best right now, in the moment, isn’t always the best thing overall. If it were, then putting a three-week European vacation on a credit card would be a good idea.

One way of overcoming short term emotion is by using the 10/10/10 method. Ask yourself how you will feel about this decision in 10 minutes, 10 months, and 10 years. How we feel in the moment tends to dominate in our decision making, but if we can figure out how a decision will make us feel in 10 months or 10 years, we can gain perspective. That doesn’t mean that the now feelings aren’t important or that the later feelings are more important, but it’s helpful to make sure you’re thinking through both.

The Status-Quo Bias and Loss Aversion

We like things the way they are. In fact, we’re so comfortable with the unknown that we will make bad decisions in order to avoid the unknown. It’s why some recently released inmates reoffend simply so they can go back to prison. It’s why companies go bankrupt rather than adapting to meet a changing marketplace. And it’s why we insist on doing things the way we’ve always done them. In order to make good decisions, we must overcome our fear of change.

Related to the status-quo bias is our aversion to loss. We have far more fear of losing what we already have (what we’re familiar with) than we have hope of gaining something new. And this leads us to make decisions to preserve what we have, even if those decisions ultimately do more harm than good.

This is why people people pay for extended warranty coverage. The actual value of an extended warranty is a fraction of what it costs. Products aren’t likely to break during year two of ownership, but people are afraid of their new TV giving out on them two weeks after the warranty expires.

We need to overcome our fear of the unknown and our overvaluing of what we already have in order to accurately assess our circumstances and make the best possible decision.

Let’s say that in order to implement monthly coaching huddles, you need to do away with larger quarterly leadership gatherings. Those larger gatherings are helpful, but you know there’s something more you could achieve. Our natural tendency is to keep doing those gatherings because “If it ain’t broke, don’t fix it.” We’re hesitant to risk something that’s nominally working in order to pursue something that has great potential but is unproven. However, if we want to make real progress, we have to be willing to embrace the unknown.

What Would Someone Else Do?

One key way of overcoming short-term emotion, status-quo bias, and loss aversion is to consider what someone else would do in your situation.

Imagine that a friend was facing the same decision you are facing and came to you for advice. What would you tell him or her to do? That’s probably the thing you should do yourself.

Alternatively, ask yourself, “If I quit today, what would my successor do?” If it’s clear what the next person to take over your role would do, then that’s probably the thing you should do. If a new director would kill the quarterly meetings in favor of monthly coaching huddles, then you should, too.

Honor Your Core Priorities

What is important to you? What is important to your organization? If you want to make the best decisions, decisions based not on the excitement of the moment or the fear of loss, then you need to know what is truly important.

When you’re offered a prestigious job, you’ll be excited and your first instinct will be to take it. But inevitably that job will come with more stress and longer hours. So are you the kind of person who values career advancement? Or is balance and time for family and friends more important to you? There isn’t necessarily a right answer, but there is an answer that honors your core priorities.

So when you’re trying to decide how to best invest in your leaders, ask yourself what are the priorities of your team and the larger organization (in this case, Eastside). One of Eastside’s priorities is leadership development, so as you’re looking at your array of options, one thing to consider is how effective each option will be at developing your people as leaders. If a monthly huddle with their coach seems like the thing best suited to develop leaders, then that is a strong argument for moving forward with that option.


  1. What do you need to do to ensure you do not make this decision based on short-term emotion?

  2. How do your core priorities and the core priorities of your ministry, team, or organization inform this decision?


Prepare to be Wrong

For all of our planning and processes, sometimes we’re simply wrong. Something happens that we didn’t anticipate, or people respond in an unexpected way. The decision that we made didn’t turn out how we had planned.

We need to be ready for that possibility, and we need to remember that we can be wrong in two directions.

Assume you decided to implement monthly coaching huddles, and you expect 50% of your leaders to come. You’ve figured out that you need one coach for every eight leaders who will participate in a huddle.

Obviously, you could be wrong in that only 20% of your leaders come, and your idea is a failure. Or you could be wrong and have 90% of your leaders come. Your idea is a smashing success, but you are now way, way short on coaches.

Bookend the Future

When you’re making a decision, don’t consider only what you think the most likely outcome will be. Consider what the worst possible and best possible outcomes could be.(1)

In the case of implementing monthly coaching huddles, the worst possible outcome is that your leaders don’t participate and maybe you even lose a small percentage of them out of frustration. The best possible outcome is that 90% of your leaders participate, and the community and development that comes out of the huddles causes your leadership base to grow by 50% within the first year.

The first thing to consider is where you currently are on that spectrum to see how much potential upside or downside there is to your decision.

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If your current model is much closer to the left side of this spectrum, then you have a small downside but lots of upside. There’s little reason not to move forward.

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On the other hand, if your current model is already producing some pretty good results and you’re much closer to the right side of this spectrum, then you would need a compelling reason to move forward, because if you’re successful your gains will be minimal, but if you’re not successful, your losses could be huge.

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In order to arrive at your bookends (best/worst possible outcomes), it’s helpful to run both a premortem as well as a preparade.

In a premortem, assume that you’ve made your decision and it has failed. Spend some time brainstorming the likely reasons that it failed. These are the potential problems you’ll want to figure out before moving forward with your decision.

Also spend some time thinking through the effect of your failure. This becomes your bottom bookend.

In a preparade, you assume the opposite: you’ve made your decision and it has been wildly successful. Spend some time brainstorming the likely reasons that it was so successful. These are things you want to make sure you do during the implementation of your idea.

And again, spend some time thinking through the effect of your success. This becomes your top bookend, the positive result you’ll need to prepare for so that you don’t find yourself with lots of leaders wanting huddles and not enough coaches to lead them.

Margin of Error

One way of ensuring that our decision doesn’t blow up in our faces is to build in a margin of error. It’s natural to see the expected outcome of our decision through rose-colored glasses.

Let’s say that some of our coaches decide to quit six months into the one-year commitment we asked them for. Now, we had said that our coaches could each handle eight leaders, but if that’s the max, it might be better to recruit enough coaches for each coach to have only six leaders; that way we have some empty slots to assign leaders to in the event a coach unexpectedly quits.

Note that building in this margin of error also helps prepare us for the possibility that a larger than expected number of leaders decides to engage with coaching or that our leadership ranks grow quickly because of the new opportunity for development.

Set Realistic Expectations

In our excitement, we often sell our ideas with great gusto, painting a picture of the outcomes as if we’re going to hit our upper bookend. This, of course, leads to disappointment all around. Even a successful idea can feel like a failure if expectations are set too high.

It’s important to make sure that those both above you and below you on the org chart have been given a dose of reality. So when you’re selling the coaching huddle idea, it’s okay to paint a picture of the opportunity, but you also want to make sure that your department head as well as your coaches understand the bottom bookend, what the result could be if things don’t go as you hope.

Set a Tripwire

As we discussed above when looking at the status quo bias and loss aversion, inertia is a powerful thing. We tend to keep doing what we’ve been doing because we’re comfortable, because it’s easier, and because we’re afraid of change. We need figure out a way to wave a big red flag and warning lights when things aren’t headed in the right direction.

We need to set tripwires, something that causes us to notice when something isn’t going as well as it needs to. For our coaching huddle experiment, there are a couple of different tripwires we could set.

One tripwire could be that if we don’t have 40% engagement from our leaders within the first six months, then we need to re-evaluate our decision. At that point we can decide whether to tweak the huddles or scrap them entirely.

Alternatively, let’s say we hit the upper end of our bookends out of the gate. For the first three months we average 80% engagement from our leaders. That’s great, and even if that’s due to initial excitement and we drop back a bit to maybe 65%, that’s still pretty good and definitely a win.

But what if we keep slipping? Let’s say we drop to 50% engagement. Still not terrible, but we’re clearly not headed in the right direction. If we’re seven, eight, nine months in, by then we have inertia. We’ve started a program. It seemed to work well, so we put it on autopilot, and we need something to snap us out of it.

In the midst of our success, we should establish a tripwire, so we say, “Things are going well now, but if we drop below 60% engagement, we need to stop and consider why and how to move forward.”

Now, we might never hit that tripwire, or we might hit it two or three years in. The decision was clearly a good one; it worked for years. But if it’s slipping, we need to evaluate how to best salvage or scrap it before it collapses on its own and causes collateral damage.

Pattern Recognition Tripwires

Most tripwires are based on a hard facts. That’s their advantage. They force us to pay attention because a clear line that we established has been crossed.

But there are other tripwires that rely more on gut feeling. When you’re dealing with someone who is experienced, at the root of that gut feeling is likely a real problem (or opportunity).

One hospital figured out how to intervene before a patient became critical by setting six tripwires that would trigger a rapid response team. Five of them were metrics based (heart rate, blood pressure, etc.), but the sixth was when the nurse was worried about a patient. In the first 18 months, the hospital’s number of code calls (when a patient dies and needs to be revived) dropped by 71%. This system saved an estimated 33 lives.

Nurses see hundreds, even thousands of patients a year. Over time, they get a feel for when something is not right. Even if the specific numbers don’t indicate anything, they can tell something is wrong that more in-depth testing or analysis would reveal.

In our huddle example, you want to empower your coaches to give feedback on how

the huddles are going. And if it’s generally positive, but then there are a couple of months where some of your coaches start mentioning that their leaders seem disinterested or less enthusiastic about the huddles than they used to be, then you need to sit up and pay attention. That’s a tripwire.

Of course, pattern-recognition tripwires work for opportunities as well as problems. Maybe your coaches notice that the leaders are more engaged when you bring in a guest speaker or when you provide dinner or when you tell stories. If you’ve empowered them to look for both problems and opportunities and truly listen when they bring those to you, you’ll greatly increase your odds of success.

(1) It’s actually a bit misleading to say worst/best possible outcomes. The worst possible outcome of implementing coaching huddles is that your leaders all quit in frustration, and the best possible outcome is that you triple the number of leaders you have in three months. You’re really looking to figure out the best and worst outcomes that are at least a little bit likely. If you’re 99% sure something isn’t going to happen (tripling/losing all of your leaders as a result of huddles), then it’s don’t worry about those possibilities in your analysis.


  1. Assume your decision has failed. What caused its failure, and what’s the worst possible outcome?

  2. Assume the results of your decision are as good as they could possibly be. What do you need to do to prepare for your success?

  3. How do these possibilities (the potential upside and the potential downside) shape your thinking as to whether or not your decision is the right one?

  4. What tripwires do you need to set in order to ensure you change direction if things are not going well with your decision? What tripwires do you need to set to ensure you capitalize on opportunity if they are?


Assuming the problem or decision you analyzed is truly a significant one, there are probably one or more aspects of the WRAP analysis you performed in this module that could benefit from some additional work. Set aside some time to invest in this step. You may also want to read Decisive to explore these concepts further.

LEADERSHIP TAKEAWAYS (to be completed during group discussion)