Creating a Better Strategy

Uncategorized Oct 02, 2025
I've spent the last nine months publicly critiquing our sector. 

And I want to emphasize the word our

I have been working on the front lines of the movement to end homelessness for 15+ years.

I began my career working in our systems as an outreach worker and direct service provider.

I've spent the last nine years working on our systems, in leadership roles in city government, with one of our nation's largest CoCs, and as a consultant working with counties and philanthropic organizations throughout California.

Zooming in, I know every single day our movement is getting people housed, ending homelessness, and transforming lives. 

Zooming out, despite those efforts, I also know it's impossible to deny that the state of homelessness is getting worse. 

It's getting worse in terms of the numbers. 

Since I joined the movement to end homelessness in 2010 in San Jose, CA, overall homelessness in California has gone up 52%. Chronic homelessness has gone up 125%.   

It's also getting worse in terms of the perceptions. 

  

 It's easy and understandable to get disillusioned by all of this.

And to that end, you might think I'm just being an armchair critic. 

But if you knew me, you'd know I am actually a profound optimist.

I love our movement and all of the amazing people in it. 

And I still deeply believe with every ounce of my being that we can solve homelessness in the United States, on our terms.

The problem is - I sincerely fear we are running out of time, and if we're going to be successful, we have to change our approach, fast.

 

Being Honest with Ourselves

A couple of years ago I stumbled on an amazing book about strategy for social movements.

It's called Tools for Grassroots Activists, and it was created by the clothing company Patagonia, which has a whole philanthropic arm dedicated to helping environmentalists preserve and conserve natural places all across the world. 

While the context is different than our own, the insights cut across sectors, beginning with what the authors describe as the fundamental problem many social activists face:
  • “Leaders fail to appreciate the importance of developing a strategy, how tactics fit into a strategy, and the difference between the two.”

To put it bluntly, this happens because:

  • "Leaders simply don’t like to answer the hard questions. The questions like: Why are we doing these things? Will this really win our campaign? What is it going to take to influence the key decision makers we need? Often these questions challenge long-held assumptions, expose weaknesses in our campaigns, and force us to face the reality of what it will truly take to win the issue, not just work on the issue.

In this spirit, everything I have written over the last nine months has been a good faith effort to be honest about what is holding our sector back from being more effective.

To summarize:

  • It's less that our current strategy is failing and more that, as a movement, we do not have a unifying national strategy to begin with. 
  • The biggest reason we don't have a unifying national, sector-wide strategy is that for the last 45 years, since the dawn of the modern homelessness crisis, we have hopelessly fragmented the response, leaving every county, city, CoC, and service provider more or less to their own devices to figure out what to do. It is this structural fragmentation that fuels many of our biggest challenges.
  • Fragmentation fuels inter-governmental finger-pointing and disinvestment.
  • Fragmentation fuels the growth of large and uncoordinated systems of care.
  • Large and fragmented systems exacerbate chronic homelessness.
  • Fragmentation fuels the loss of institutional knowledge.
  • Fragmentation fuels and incentivizes short-term thinking.

In sum, as I shared last time, if you simply sat down and made a list of all the things you would NOT do if you wanted to try to solve homelessness, we are doing pretty much everything on that list. 

So, if we want to get serious about building and implementing a new strategy, what should we consider? 

 

First, a Confession

In 2020, after a decade in this work, I became a full-time "strategic planning" consultant.

One of the biggest motivators was that I had just had the incredible opportunity to be part of a team that, over a two-year period between 2017 and 2019, drove a 28% reduction in CoC-wide chronic homelessness and a 30% reduction in unsheltered homelessness in the city where I worked.

This reduction happened at a time when about 80% of CoCs in California saw increases in homelessness. It also occurred in a community that:

  • In 2017, had the 7th highest per capita rate of homelessness in the entire country
  • Had objectively one of the most expensive housing markets in the country, which only got worse every year we made progress
  • Faced multiple funding freezes and other resource cliffs during the first Trump administration

(Seeing this dramatic decline in the face of so many headwinds has given me an absolutely unshakeable belief that we - the homeless service sector - do not need external conditions to change in order to spark more progress as a field.)

Therefore, my dream became helping other communities drive similar impact.  

There was just one problem.

While we had undeniable strategic momentum during that time, our approach had never been formalized in a written plan. 

When I looked at all of the big "strategic planning" consulting firms, it seemed like helping a community "be strategic" meant charging $100,000+, spending a year doing interviews and focus groups, and then drafting a 100-page document with a dozen "strategies" and a hundred different action items.

You probably already see where this is going ... 

And don't worry, I'm going to send you a full post on the futility of "strategic plans." 

Instead, I've spent the last 5 years studying what goes into effective strategy while also trying to reverse engineer what has happened in the communities that have driven the most significant, rapid reductions in homelessness. 

That's what I want to begin sharing with you today. 

 

Accelerating Momentum

There are two books that have profoundly shaped my view on strategy.

The first is the one I mentioned earlier, Tools for Grassroots Activists

The second is Good to Great (this article offers a great summary). 

This classic business book by Jim Collins is the best thing I've read that approximates what it has actually felt like to be part of some of these high-performing, strategic teams. 

Good to Great originally looked at private sector companies that consistently outperformed the S&P500 (i.e., they sustained long-term, above average returns). 

Jim's research has found that many of our typical explanations of high-performance are incorrect. Change doesn't:

  • Happen in a single moment
  • Come from fear, threats, or crisis
  • Depend on money, financial incentives, or new investments.
  • Rely on a revolutionary new program or technology.
  • In fact, it doesn't rely on a revolution at all.

Instead, success comes from sustained, compounding momentum, or as Jim calls it - "The Flywheel Effect." Over a long enough period of time, with the following three components, anything becomes possible:

  • Disciplined people
  • Disciplined thought
  • Disciplined action 

Every time I revisit these books, I get something new out of them. And this time around, it's the order of those three components. 

I think this full anecdote is worth a read:

  • You are a bus driver. The bus, your company, is at a standstill, and it’s your job to get it going. You have to decide where you're going, how you're going to get there, and who's going with you.
  • Most people assume that great bus drivers (read: business leaders) immediately start the journey by announcing to the people on the bus where they're going—by setting a new direction or by articulating a fresh corporate vision.  
  • In fact, leaders of companies that go from good to great start not with “where” but with “who.” They start by getting the right people on the bus, the wrong people off the bus, and the right people in the right seats. And they stick with that discipline—first the people, then the direction—no matter how dire the circumstances. 
  • Take David Maxwell’s bus ride. When he became CEO of Fannie Mae in 1981, the company was losing $1 million every business day, with $56 billion worth of mortgage loans underwater. The board desperately wanted to know what Maxwell was going to do to rescue the company.  
  • Maxwell responded to the “what” question the same way that all good-to-great leaders do: He told them, That’s the wrong first question. To decide where to drive the bus before you have the right people on the bus, and the wrong people off the bus, is absolutely the wrong approach.  
  • Maxwell told his management team that there would only be seats on the bus for A-level people who were willing to put out A-plus effort. He interviewed every member of the team. He told them all the same thing: It was going to be a tough ride, a very demanding trip. If they didn’t want to go, fine; just say so. Now’s the time to get off the bus, he said. No questions asked, no recriminations.
  • In all, 14 of 26 executives got off the bus. They were replaced by some of the best, smartest, and hardest-working executives in the world of finance.  
  • With the right people on the bus, in the right seats, Maxwell then turned his full attention to the “what” question. He and his team took Fannie Mae from losing $1 million a day at the start of his tenure to earning $4 million a day at the end.
  • Even after Maxwell left in 1991, his great team continued to drive the flywheel—turn upon turn—and Fannie Mae generated cumulative stock returns nearly eight times better than the general market from 1984 to 1999.   

While it's fun and energizing to be aligned and driving action, at least speaking from my own experience of being on teams that did turn around systems of care, it really was a team. At some point, the right group of people, almost by magic, seems to come together, and things just start changing. 

And if I really had to reduce down to a certain quality or mindset, it's simply a dedicated group of core leaders who are willing to look beyond the way things have always been done, who are hungry to borrow and draw inspiration from others, and who are committed to creating a culture of ongoing learning, innovation, and excellence.

That’s it.

Adopting this mindset, slowly at first, but faster and more significantly over time, fuels unstoppable alignment, focus, and acceleration.

 

Do You Want to Do Something Amazing Together?

I have one more quick confession, and then we'll wrap this up. 

These newsletters and other content I put out, it's all a labor of love for our movement.

But, at the end of last year, I wasn't planning to do any of this. In fact, I came incredibly close to fully walking away from our movement altogether. 

I don't think I have to tell anyone reading this that our work is extremely challenging, and it's so hard to maintain hope and optimism when things just keep getting worse, year after year, now decade after decade. 

But then something unexpected happened. 

A new presidential administration took over in January and the writing was immediately on the wall for what that meant for the state of homelessness in this country. 

And now, aside from the initial idealism I had when I started doing outreach all those years ago as an AmeriCorps VISTA, I don't think I've ever been as fired up about ensuring the future of our movement. 

So here's the ask. I am looking for all of the homelessness Change Makers across this country who know we - the homeless service sector - can do a better job responding to this crisis and know that we don't need external conditions to change to transform the effectiveness of our movement.

If you feel that, I hope you'll join me and spread the word. 

- Andrew

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