I’m the city’s community development director and I report to the city manager. My mid-sized city has a homelessness challenge that is growing. Exacerbating the problem, we are being sued because the city and state highway department took down a make-shift encampment of tents and cardboard shelters under a state highway overpass in the city.

As a response to the homelessness crisis, homeless advocates, with the support of faith-based groups, are urging the city council to fund and build a village of tiny homes under the overpass where the encampment was located.  A few city councilmembers are supportive and others on the council are noncommittal.  In response to the advocates, the city council did authorize a council subcommittee to explore appropriate city action.

The city manager is being very cautious. She worries that the tiny homes village is too big an investment; it’s an imperfect solution; it won’t solve the crisis; and therefore, the proposal is too risky. The city manager is also concerned about the city operating and maintaining the village if it is constructed.

I am energized about the possibility of ameliorating the homeless problem. We do have some potential resources. The city has collected a fair amount of affordable housing monies from developer fees and the state does own the land under the highway overpass. The city also owns some vacant lots. However, I am hesitant because I don’t have a lot of expertise in dealing with this kind of challenge and of course any significant response would be controversial. 

How do I figure out how to proceed?

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I congratulate you for trying to figure out this messy and volatile situation.  The homelessness crisis is a classic adaptive (not technical) challenge:

• It’s complex.
• There is no right or wrong solution.
• Uncertainty abounds.
• Any action is risky and will be criticized.

Why do you need to act?

You are dealing with a messy and complex issue with uncertain outcomes. In such a situation, we not only tend to be cautious, we also overthink the problem and opportunity.  We seek clarity amid the complexity.  However, the only way to get clarity is to do something. As Dan Rockwell suggests, “the path emerges as you move forward, not before.” Leadership Freak blog, “Making Decisions When the Path Is Uncertain and Confusing,” Jan 1, 2020.)

By taking action, you can achieve some clarity about what works, what doesn’t work, and how you can modify what you are doing in order to continue to move forward.

Action (not thinking) also helps you learn in the real world.  You can’t learn much about tiny homes before you go.  You can only learn as you go.

Furthermore, taking action also invites more action by yourself and others.  (Dan Rockwell, Leadership Freak blog, “7 Questions that Confront Paralysis,” Oct 4, 2014.)

To address the big adaptive challenges facing local government, we must innovate.  Developing a successful tiny homes project would certainly be an innovative response to the homelessness crisis.  Innovation requires action coupled with reflection.  We act, make some mistakes, reflect, and apply what we learn.  Innovation does not happen without learning from mistakes.

Finally, action reduces some of our fears.  We often do not take action because we fear that

• People won’t like us.
• We may fall on our face.
• Others won’t follow us.
• We don’t have the leadership skills to pull something off.
• We’ll get fired.

Most of these fears are unlikely to occur.  (See Career Compass No. 58: Overcoming Deep-Seated Fears.)  By acting, we often discover that our fears are overblown.  “Fear shrinks when you step into it.”  Dan Rockwell, Leadership Freak blog, “How to Overcome Overthinking and Get More Done,” Nov 26, 2019.)

How do you deal with so much uncertainty?

To address adaptive challenges like homelessness, local government action should mirror military strategy which requires clarity about direction (eliminate homelessness) and flexibility about how to get there.  If you decide to respond to the homelessness challenge, you must see the process as a journey and thus be open to the twists and turns of the journey.

In taking action, you want to get things “roughly right.”  It’s “ready, fire, aim.”  You want to fix things up as you go.  You cannot know everything before you go.  The key competency for 21^st century leaders is “FIO” (figure it out).  (See Career Compass No. 65: FIO.) 

Before acting, you must ask some questions that will produce imperfect information.  And then you must act.

What are some questions to ask before you act?

To decide if and when to act, leaders like you need to ask themselves and others certain questions:

1. How important is the issue to our organization and community?
2. Can I make a contribution to help address the problem?
3. Is this homelessness challenge aligned with my values and passion?  (See Career Compass No. 18: Taking Smart Risks.)
4. What are the costs of not acting?
5. Who else can I engage in order to move forward?
6. Given the lack of commitment to act by others, what are one or two steps forward that I can take with others without formal approval?
7. Even though some action may not solve the problem or be “perfect,” would some forward steps make the problem better?
8. What would my best self do? (See Dan Rockwell, Leadership Freak blog, “7 Questions That Confront Paralysis,” Oct 5, 2014.)
9. What do I fear?  How likely is that fear?
10. If I move forward, what is the possible harm?

What are some concrete ways for you to move forward?

To take a few steps forward with others (which will hopefully lead to more steps forward), you need to decide what you can do within your sphere of influence.  For instance, you could:

• Identify a few staff from the Community Development Department, and other departments such as the Community Services and Police Departments, who would like to work with you to explore solutions to the homelessness challenge.
• Invite a few volunteers to join your work team from the faith-based community, homeless advocacy and support organizations, and business and neighborhood groups.
• Use your work team to conduct a series of one-to-one conversations with homeless folks on the streets (to get a better sense of their reality and what they desire), as well as other stakeholder groups, such as business and neighborhood representatives and police.
• Visit other tiny home projects and identify best practices and lessons learned.
• Identify other exemplary responses to the homelessness crisis, such as the use of trailers to provide transitional housing for the homeless.
• Explore with local nonprofit organizations which agencies could operate and maintain any tiny home village as well as provide supportive services.
• Identify potential sites for the village, especially those that are publicly owned.
• Find funding, such as affordable housing fees from developers.
• Figure out a “minimally viable product” to test out the tiny homes village concept.
• With ideas from all stakeholders, draft a pilot project proposal with a budget for a pod of 5-7 tiny homes in order to test the viability of a full-fledged village.
• Keep the city manager and the council subcommittee advised of your research.
• Present to the subcommittee the proposal with the participation of all the stakeholders.
• Deal with any reluctance by asking the council subcommittee members “What are several steps forward that you would be willing to try?” and then take the steps forward.

In taking these small actions, you want to use the big picture (i.e., end homelessness in my community) to evaluate options for actions ((i.e., develop tiny homes village).  You want to do something that advances the big picture solution.  (Dan Rockwell, Leadership Freak blog, “Making Decisions When the Path Is Uncertain and Confusing,” Jan 21, 2020.)

Think big, act small.

What about patience?

Previously, I have noted that patience is a leadership virtue.  (See Career Compass No. 75: Patience Is a Leadership Virtue.)  A leader does need to let events unfold and issues ripen.  However, while waiting for positive conditions to emerge, a leader can still use the time to do something such as the actions identified above.  For instance, you can engage city staff and outside stakeholders in conversation about the homelessness challenge.  You are not trying to avoid action.  Authentic conversations lead you to action.

Be patient and take a step or two forward.

How do you deal with your discomfort?

You are going to feel discomfort in taking action.  You don’t know the reactions of the city manager, councilmembers, and other stakeholders.  You also don’t know with any certainty the outcomes of your beta test of the tiny homes pod project.

Remember, discomfort is good.  You cannot learn or grow without getting uncomfortable.  You want to be uncomfortable without feeling overwhelmed or distressed.

The “sweet spot” of learning and growth is when you have a 50-70% chance of success.  If you have a 90% chance of success, it is too easy and you don’t learn much or grow.  If you only have a 40% chance of success, it is too difficult and you may feel great distress and withdraw.

If the endeavor is in your sweet spot, you are more likely to be fully engaged and energized and champion the project across the finish line.

What are tips to take action amid uncertainty?

In a messy world, you need to act and take a few steps forward.  Because of the uncertainty, you must take some risks.  There is no pay off without taking risks.

Here are some suggestions for taking “smart risks” in moving forward:

1. Do something if it is aligned with your values and passion

If a challenge is not aligned with your values and passion, don’t take the risk.  Since you seem to be committed to social justice, you might be willing to act.

2. Connect with others

To create a state of readiness for any proposed solution, you need to create relationship and connection with others.  Relationship must precede problem-solving.  Stake-holders are more likely to be open to your ideas and leadership if you have built a relationship with them.

3. Communicate with confidence

You must talk with confidence even without 100% certainty.  Even if you are uncertain about the outcome of taking action, you cannot demonstrate uncertainty or anxiety.  If you show anxiety, you will transmit it to team members or other stakeholders.

Before communicating, take a deep breath and figure out what internal or external stakeholders need to know.  Ask yourself about their interests, concerns, fears, and questions.  The quicker you respond to their questions and concerns, the quicker you can calm their fears.  Once you have responded to their concerns, you can talk about next steps and encourage stakeholders to join you on the journey.

Even if things do not progress exactly as you envision, “people will be more forgiving if they feel like they are part of the process.” (Nancy Duarte as quoted by Allison Shapira, “How to Reassure Your Team When the News Is Scary,” hbr.org, March 5, 2020.)

4. Actively seek out others who also want to do something positive

As you connect with stakeholders, seek out potential partners.  Finding partners inside and outside the organization allows you to generate diverse ideas, amalgamate resources, and build political support.  Partnering with others also spreads the risk.  It is difficult for opponents to attack you if they must also attack your partners (such as clergy or business leaders).

5.  Demonstrate humility

Heroic leadership does not solve adaptive problems in the messy world of local government.  Hero leaders assert that they have all the answers, they know the one path forward, and they seek “buy-in” for their ideas.  People don’t gravitate towards heroic and arrogant leaders.  Rather, humble leaders attract support for their ideas because they demonstrate their values, acknowledge that they don’t have all the answers, seek out even better ideas, invite others to join, and follow as well as lead.  (See Career Compass No. 76: Humble Leaders Get Results.)

6. Incorporate the ideas of non-experts

As community development director, you are an expert.  Non-experts do not have your expert assumptions.  Instead of an “expert’s mind” (which is a closed mind), they have a “beginner’s mind” (which is an open mind).  Diverse ideas from non-experts will lead to creative solutions.  (See Career Compass No. 72: How Do We Generate Creative Ideas?)

7. Get everyone’s “fingerprints” on the proposed action

Given the lack of commitment by some of the councilmembers and the city manager as well as the outright opponents, you must engage everyone in authentic conversations and identify their hopes, concerns, fears, and ideas.  Then you need to demonstrate that you have responded to their ideas and concerns (even though you may not agree with those perspectives or solve all the problems that have been raised.)  With everyone’s “fingerprints” on the pilot project, your idea morphs for the better and becomes “our idea.”

8. Conduct a “pre-mortem”

To minimize obstacles and missteps that may block your efforts, conduct a “pre-mortem.”  Don’t just jump into action.  Before you start the project, gather all your internal and external partners and ask the group to imagine that the project is 18 months down the road and a lot of things have gone wrong.  Your team then writes down all the negative things on a white board after which your group reengineers the project work plan so that it minimizes the anticipated obstacles or missteps.

9. Propose a “minimally viable project”

Instead of proposing to build a whole village of tiny homes for homeless people, make a little bet and seek to experiment with a “minimally viable project.”  (See Peter Sims, Little Bets: How Breakthrough Ideas Emerge from Small Discoveries, 2011.)  In your case, test out a pod of 5-7 tiny homes or trailers with a shared restroom and showers with supervision and supportive services provided by a nonprofit agency experienced in serving homeless clients.  You can learn from this beta test, fix up problems as they occur, learn as you go, and eventually develop a winnable village solution.

10. Debrief along the way and be flexible

Assuming you get approval to undertake a pilot project, understand that it gets particularly “messy in the middle.”  Because change projects and other innovative solutions may stall, you must as a leader be open to pivoting. 

To learn as you go and make adjustments, debrief with your partners your ongoing efforts:

• What is working well?
• What is not working well?
• What are we learning?
• What adjustments do we need to make?

Change for the better is a journey.  You must be open to the twists and turns of the adventure.  Again, you must be clear about the desired end result yet flexible about how to get there.

Amid the adversity and messiness in the middle, you must sustain the effort.  As Winston Churchill advised, “It is the courage to continue that counts.”

11. Celebrate progress

Since any change project of significance may take a lot to time, your motivation as a leader and the motivation of others may wane over time.  Therefore, leaders must demonstrate progress.  As you achieve certain milestones (i.e., commitment of the land for the pilot project), celebrate progress with followers.  (See Theresa Amabile and Steven Kramer, The Progress Principle: Using Small Wins to Ignite Joy, Engagement, and Creativity at Work, 2011.)

12. Get coaching

Informal coaching from savvy peers inside and outside the organization can advise you on how to navigate the uncertainty and messiness of your enterprise.  Every 21^st century leader requires coaching.  (Go to ICMA’s “CoachConnect” registry of one-to-one coaches available to all local government professionals.)

All the big challenges are messy.

All the big challenges facing local governments are adaptive in nature.  They include responding to homelessness, traffic congestion, pandemics, the opioid crisis, gangs, unaffordable health care, the move toward technology-enhanced service delivery, community divisiveness, the demands of our changing demographics, and climate protection.

Even though these adaptive challenges are urgent and demand action, it is unclear how to act. . .but leaders must act anyway.  To paraphrase Tom Peters, great leaders have a “bias for action.”  (See Tom Peters and Robert Waterman, Search for Excellence—Lessons From America’s Best Run Companies, 1984.)  They do something to move forward, fix things up, and learn as they go.

Amid all the uncertainty and angst, great leaders are compelled to act and do something.

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Sponsored by the ICMA Coaching Program, ICMA Career Compass is a monthly column from ICMA focused on career issues for local government professional staff. Dr. Frank Benest is ICMA's liaison for Next Generation Initiatives and resides in Palo Alto, California. If you have a career question you would like addressed in a future Career Compass, e-mail careers@icma.org or contact Frank directly at frank@frankbenest.com. Read past columns at icma.org/careercompass.

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