Five Sure Signs that the Leadership in Ending Homelessness has Gone Awry

I’ve been thinking a lot about leadership in the pursuit of ending homelessness lately.

Part of it stems from helping a few communities update their 10 Year Plans to End Homelessness. In some instances, this has been a pure joy – an inspiration to me and my team. In other instances, it has been a train wreck – a reminder that at times local leaders go out of their way to prevent success rather than encourage it.

Part of it stems from working with a handful of communities to get coordinated access and common assessment systems into place. In some instances leaders have sown the seeds for this to happen for years. In other instances, the experience has demonstrated that a lack of leadership reinforces a service approach quite distant from proven practice.

Part of it stems from rolling out our new Team Leader Boot Camp. In some instances, I have experienced “leaderfull” communities, brimming with pride and a shared commitment to invest in leaders that can help programs succeed. In other instances, I have seen people declared the leader of a program because they were the least of all potential evils, or wouldn’t rock the boat, or because of tenure, not talent.

Part of it stems from engaging with elected officials across the entire continuum of ideology. In some instances I have experienced leaders wanting to learn and engage in dialogue about practice and ideas. In other instances I have experienced leaders more interested in their narrow worldview and sound of their own voice that I can only (desperately; bewilderedly) wonder if what they say reflects the populace that put them in office.

So, I have been thinking about the common attributes when leadership isn’t working the way one like want it to when it comes to ending homelessness. Here are the five sure signs that I have come up with based upon what I have seen the most.

1. Excuses Trump Solutions

The royalty of naysayers, these folks use all of their air time in meetings or in media to talk about why things do not or cannot work rather than engaging in constructive conversation about how to solve issues. Finger pointing is common too, which is even more divisive. I’d have to say a certain amount of defensiveness is also the norm, as if generating ideas to address the excuses is somehow a personal insult to their leadership.

2. Delusions of Grandeur

Too often I have found these folks to be remarkably well trained and polished in messaging without the complimentary investment in substance. Perhaps you have also heard over-the-top overtures of how confident a leader is in her/his own ideas or plan or goals even when the idea, plan or goal doesn’t pass the smell test. It never seems to propel a community forward (or end well) when the grandiose concepts put forth defy objective reasoning. I find a smidgen of ego-tripping happens with these delusions too where the leader heaps praise upon themselves for the idea, plan or goal without acknowledging all the others involved in generating the idea, plan or goal. A cult of personality ensues.

3. Bullying Into Submission

The bully is prone to use anger and aggression to get their way, masking their own insecurities, or as an explicit strategy to challenge feelings of being threatened or scared. Might is not right. Every person in a community may not get behind the ideas of a leader (without followers, though, there is no leader) but using position-power (“I’m the Boss, so do what I say”) to force people to perform in a certain way without providing a transparent rationale, reasoned discussion, and evidence is a sign of weakness, not strength.

4. Controlling

The person hell-bent on controlling everything through themselves – every decision big and small; every press release or public announcement; every staffing decision; etc. would seem to simply have a passion for micro-managing. But, I have found many of these otherwise fine individuals have a huge fear of failure and cannot accept the mistakes of others, even if those mistakes are essential for growth. The controlling person also pushes other potential leaders that they work with out of the spotlight, as the potential leaders see no future state where they too can make decisions. At the same time, they may wonder why others around them are incompetent, why there aren’t enough good leaders to work with or choose from. They don’t realize that their controlling behavior makes them blind to the human resource assets around them.

5. President of the Local Chapter of Workaholics

These folks measure everyone else’s efforts and commitment against the pattern of their own behavior, and their behavior if you really dissect it, is being busy most waking hours, most days – but actually accomplishing little. Booking “routine” meetings with these folks is like handling the logistics of landing a fighter jet on an aircraft. They let people feel like they are in the inner circle when they extend the invitation to lunch or a meeting to others and use it as a display of power. How busy someone is cannot be misunderstood as being effective. Leadership is not measured by the number of hours worked in a day. People only have so much bandwidth to work with, and extending it to pursuits beyond the most important work of ending homelessness is a waste.

Consider these action items to get the ball rolling towards remedying shortcomings in leadership:

Peer to Peer Chat

When leaders have others that they would perceive as equals, the conversation about how to change leadership tactics can be more persuasive than people that report to the leader, which the leader may be more dismissive of or misinterpret as something other than genuine concerns about successful leadership


The best leaders often have access to mentors throughout their careers that can provide an important, non-threatening touchdown point. A variety of mentors across different professional disciplines and years of experience can be very enlightening.


Sometimes confused with mentorship, this is about working in a secure, confidential manner with another professional to hone leadership skills, and create a personalized plan to build upon strengths and address deficits in leadership capabilities. It can happen completely behind the scenes, and these days can also happen remotely, drawing upon some of the best coaching minds in communities hundreds of miles away.


Leader-specific training is a worthwhile investment for all leaders regardless of their years of experience or skill set. Who doesn’t want another tool to use for their work leading others? Training also creates a networking opportunity to tap into other leaders and their experience. Sometimes the experience of training is also about sharing wisdom and experience with others.

Access to Information

Providing a good written (short) briefing on the most salient evidence and facts for a leader to become aware of in their work to end homelessness or strategies in leadership (or whatever the relevant topic) may expose them to ideas in a way that no conversation is capable of doing.

About Iain De Jong

Leader. Edutainer. Coach. Consultant. Professor. Researcher. Blogger. Do-gooder. Potty mouth. Positive disruptor. Relentless advocate for social justice. Comedian. Dad. Minimalist. Recovering musician. Canadian citizen. International jetsetter. Living life in jeans and a t-shirt. Trying really hard to end homelessness in developed countries around the world, expand harm reduction practices, make housing happen, and reform the justice system. Driven by change, fuelled by passion. Winner of a shit ton of prestigious awards, none of which matter unless change happens in how we think about vulnerability, marginality, and inclusion.

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