Leading Through the Messy Middle: Three Keys in Crisis

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There are some of us who love to start things, and others who love to finish things.

Starting things is super fun and exciting, especially for creative folks like myself. We get to try all sorts of creative ideas and the process itself is stimulating. The future is unknown and the possibilities seem endless!

Finishing things can feel great too. All that hard work is finally coming to a close and you can see the end in sight. There is great satisfaction in closing the books, checking off that final box, and celebrating the outcome.

Between the start and finish, it’s often not so fun.

The start is usually quick, the finish is also relatively short, but that middle? It goes on foreveeeeeeeeeerrrrrrrr…

The Messy Middle

There are so many points where it would be easier to give up. In the middle it can also feel like the valley. You can’t see out of it and you’re not even sure you’ll make it to the end. You may not even know what the end looks like any more.

This is certainly true these days in the midst of crisis. Every day the news bring out more new information that we currently did not know. There are constant changes in the journey. It is hard to envision a future when the present keeps changing.

This is the Messy Middle. It’s being in a place where you’re fast past the beginning and the end is nowhere in sight. Whether it’s:

  • Slogging through mountains of reports and paperwork trying to analyze what’s going on and figuring out the future

  • Trying to remain financially viable and the market continues to be volatile

  • Healing from a painful relationship or situation and going through a long process of grieving

  • Trying to keep the team together when it’s fracturing and going in different directions

The Messy Middle is exhausting. Leaders are exhausted. Followers are exhausted. Resources are strained. Morale slips.

Four States of the Messy Middle

Teams in the Messy Middle can be in one of four states:

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  1. Moving Backwards Team. The Moving Backwards Team is in a terrible state. Not only is it not making progress, but it is actually devolving back to an even worse state! This may be a team that faces tremendous conflict that splinters the group or is facing toxic elements.

  2. Mired Team. The Mired Team is stuck. Whether it’s because people don’t want to change or follow the leader, there is too much challenge or trauma that has sucked the morale out of people, or the path is so unclear that all there is, is confusion, this team is truly stuck and unable to move forward.

  3. Maintenance Team. The Maintenance Team is moving, but at a very slow pace. It plods along, getting the minimum done to keep things going. Sometimes this is due to survival, and Maintenance state should actually be celebrated. However, long-term the team needs to move beyond maintenance because the external rate of change is so tremendous.

  4. Momentum Team. The team is moving forward in a positive way. Over time it creates a sense of momentum to head towards the ultimate goal. Morale improves and mission work becomes more effective.

There are many nuances of leading through the Messy Middle, and today I want to point out three that help teams develop a sense of momentum.

1. Set expectations.

People who think they are stepping onto a cruise ship have very different expectations than those boarding a battleship. Does your team expect this pathway to be more of a cruise ship experience or a battleship experience?

One of the challenges of the COVID19 crisis is that many of us were really on cruise ships. Not that leading was a walk in the park, but by and large it was business as usual and we dealt with the challenges in a more predictable environment.

Now we are in a time of crisis where our cruise ship has instantly been transformed to a battleship. The waters are turbulent, there are foes and fears all around, and some of us even question the possibility of survival.

Setting expectations is an important task to help people mentally weather the challenges.

The point of starting a project is usually the exciting moment. We anticipate the path of what needs to be done and feel like it will be like this.

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For those of us who are more optimistic (my husband tells me I am one of these people), we may even think it’s like this:

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A short hop and skip, and we are done! The pathway has been pleasant, the experience enriching, the results amazing. Cue the music, balloons and butterflies!

(My husband is an engineer and has the opposite approach. He thinks of every potential thing that can go wrong. He says, “This will take me two hours,” and ten minutes later he comes back and says, “I’m done.”)

Optimistic leaders anticipate that things will go smoothly and any kind of challenge can easily be swept up and tidied.

Sadly, this cruise ship mentality doesn’t stand the test of reality. When we look at what really happens, it looks more like this.

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In fact, that might actually be an overly optimistic view. The reality is it looks more like this.

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Yup, that is definitely a better expression of what is going on these days.

As leaders, we need to set expectations. We don’t pull punches that it’s going to be tough and difficult. But we also don’t leave people in the dumps. We provide the hope to point them to a better future. We journey through this together.

I recently learned of the difference between containment and collusion. Those of you familiar with the psychology field may have known about it for ages, but I learned this in recent times and have found it immensely helpful in leading during crisis.

  • Containment is allowing people to express their turbulent state, validating their feelings, and giving them hope of a better future. It’s letting people know that they are not alone, and that we will journey through the uncertainty together.

  • Collusion is agreeing with a person and leaving them in a negative state or, worse yet, adding to the negativity. 

John 16:33 is a great example of containment.

“I have told you these things, so that in me you may have peace. In this world you will have trouble. But take heart! I have overcome the world.”

Jesus acknowledged the trouble and hardship that His disciples would be facing, but gave them the hope to persevere. As leaders, we set the expectation for people that the journey will not be easy, there will be setbacks, but we will learn and grow together and emerge on the other side stronger in faith and maturity.

2. Balance momentum and morale

Morale is a very tricky thing in the Messy Middle. Very likely, it goes down the longer the Middle drags on. The Israelites were no doubt excited to leave Egypt. But once the Messy Middle hit, the complaint committees started in full force. Moses had his hands full trying to keep momentum going. Fortunately, he had God on his side. If there’s one way complaint committees get shut down, spontaneous fire to burn people up (Num 11:1), severe plague (Num 11:33), and leprosy (Num 12:10) do the trick.

We don’t quite have access to such techniques, but as leaders we need to simultaneously monitor momentum and morale.

The faster the momentum, the lower the morale goes. People do not do well when things move too quickly. Changes take time to absorb.

However, if we move too far on the other side, with elevating morale to the highest standard, momentum gets compromised. It takes a lot of time to keep people happy. Constant processing or having people involved in every decision for ownership is extremely time-consuming.

The job of the leader is to find the tricky balance point… keep morale high enough for momentum to be had, but don’t let the momentum go too fast so that morale falls through the floor.

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The sweet spot varies depending on the organization. For organizations with charismatic and trusted leaders, the momentum can happen at a quick pace if people are used to top-down leadership. Morale remains high because people trust the leadership. However, if momentum continues at an insane pace, morale starts going down because people get burned out.

Organizations where people do not trust the leadership or where there are many complex factors that cause discouragement, even if the pace is at medium speed, morale immediately goes down.

But there’s a twist. Add crisis to the situation, and you can take everything I just said and throw it out the window.

Why? When you are in crisis mode, you need to move quickly.

The very nature of crisis is urgent. If you wait or respond too slowly, the patient bleeds out and dies.

If you refer to the handy dandy diagram above, when momentum is too high (on the right side of the diagram), morale takes a hit. People are likely reeling from the crisis itself, and then whatever directions the organization takes are different than the usual patterns. This introduces more change, which increases the perception of pace, which them makes morale go down further.

In this case, leaders must engage in triage efforts. There are many posts on crisis leadership on these topics so I won’t go into detail here. A few ways we can support the team members is by encouraging them to focus their faith on God rather than circumstances, communicating openly and often, and building community efforts so people do not feel alone. Leaders must make courageous timely decisions, communicate with clarity, and cast vision for a hopeful future. Involving as many people as possible in the short time that is available for decision-making also helps the team weather the challenges. (See the DARING Tree for a helpful tool that clarifies to people where they fall on the decision making process.)

3. Take “win” snack breaks

The journey through the Messy Middle is long and arduous. Over time our people can suffer from dehydration and hunger. 

As a leader, sometimes we can get fixated on the feast at the end. We can’t wait to get there and accomplish that goal so that we can have a ten-course banquet and huge celebration!

If that is our approach, our people may all pass out or even die along the way before they make it to dinner time.

One way to move people into a Momentum Team is by celebrating the little wins all along the journey. These are little “snack breaks” so that people can be replenished before they hit the big feast.

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One thing that boosts morale and helps people gain a sense of well-being is the feeling that they are making progress.  In “The Power of Small Wins,” the authors discovered what they call “the progress principles: Of all the things that can boost emotions, motivation, and perceptions during a workday, the single most important is making progress in meaningful work.”

When people experience setbacks, they get discouraged. Seeing progress helps workers stay motivated and happy.

Personally, I am not too great at celebrating. My celebration of something accomplished is getting to start something else and immediately diving into the next project. Fortunately, I married a man who is more fun-loving who has taught me to celebrate the little things in life. He is a professor who hates grading, so he grades x-number of papers and then rewards himself with a break and plays video games or does another fun activity. This helps him get through his mountain of papers.

Likewise, we can bring these small feelings of accomplishment and satisfaction to our teams. We can celebrate little points of progress, even in the midst of a crisis. If we are bad at this as leaders, we can recruit those who enjoy it (which I am going to do as soon as I go back to work next week!). An office I worked for had a designated “Party Queen.” She was amazing at thinking up ways to keep people encouraged and planning our staff lunches and parties. The morale was high on that team because we worked at being healthy and celebrating.

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Please share below ways that your team has tried to navigate the messy middle, especially in this state of crisis. What has helped your team stay encouraged and effective?

Angela Lin Yee

This article was written by Angela Lin Yee, Organizational effectiveness consultant and founder of Terraform Leadership Consulting.

Business and nonprofit leaders want to increase their results and crush their goals, but don’t always know the best next step to take.

In my blog, I share principles and tips so that leaders can develop thriving, productive, and effective organizations.

https://www.terraformleader.com
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