Leadership is Messy

When I worked as a Chief of Staff for a provincial minister – every morning at 7:30 we had a stand up staff meeting in the office to pre-brief on news hitting the front page or back page, or on social.

We marvelled at how the media assumed that everything the government did was well calculated and deliberate. We would joke – wow if only we were that organized or had the levers to control so much – because public policy and political decision making. is a lot like sausage making. A mess of stuff – leftovers, fine spices all rolled into a neat form – somewhat coherent.

I share this little vignette because my leadership journey has been a combination of good mess and messy mess.

In hindsight, I was well trained for this disorderly environment into which my leadership evolved. Not because I had family members who could be role models because of their super senior professions – my daddy did not go past high school and he rose to middle management before her retired. Nor because my family invested lots of money into my leadership training. Rather because I was raised in a developing nation – Trinidad.

My mummy’s family came from northern China as indentured labourers when slavery was abolished, first to Martinique then to Guyana and Trinidad. My grandfather on my dad’s side, who I never knew, arrived in Trinidad after the Wuchang uprising and at the end of imperial rule in China. They were economic refugees and asylum seekers.

They settled in land of the creolized and assimilated Carib and Arawak peoples. An island that was colonized by the French, the Spanish and then the British. A beautiful tropical island, with beaches, rain forests AND water stoppages, regular electricity outages, food shortages and lots of political unrest.

I grew up in unpredictability where outside forces beyond anyones control were the norm.  I grew up in a messy place, despite my family’s orderly life. My mother has always been incredibly resourceful and creative. There was no problem that she could solve with some ingenuity, stitching, craft or help from a friend of a friend. She had been passed over for a university education because she was a daughter between two sons. I believe she compensated for that by taking jobs with the local airline and a travel agency which afforded her discounted travel far beyond the shores of that island. That “get-it-done” attitude and infinite curiosity is also part of my DNA.  So when eventually I did get the opportunity to study abroad, I attacked that life change with the same resourcefulness and positivity. There was no mess I could not organize to my advantage.

Little did I know that I had chosen to study in the land of “peace, order and good government”.  There was so much that was not familiar to me. I knew how to deal with the unexpected, not the stability of order. I knew how to weave through a random crowd, how to aggressively cut a line to get the best seats in the cinema. I had a lot of skills.

Those skills did not serve me well when I got to Canada. That cultural adjustment resulted in lots of code-switching. Learning the secret handshake of Canada took a good decade for me during and after university and well into when I began to start a family.

At first I was grateful and appreciative because there is definitely an upside to a tidy, clean, queue inducing society. I learnt the dress code, the language code, the when-to-speak code, the which side to walk on code, the who-gets-to-speak-first-in-a-meeting code. So many rules. When you come from a place where people talk over each other. Where laughter and a cunning remark is a welcome way to cut through a tense situation – You learn the hard way what is not welcomed. And I say the hard way because much of what I understood as strengths were not considered career advancing skills.

For the early part of my career as a practising architect I learnt the building code, the beauty of a CCDC contract and the rules of what keeps buildings up – I didn’t learn anything about how to enable the communities of shanties I had to drive by every morning as a young girl on my way to school, could be designed to lift people out of poverty. That was not the rule set I learnt. I was busy revelling in this new found order and superior environment. Gradually this became my new norm.

And as if that was not enough, I found myself even more curious about the order that makes cities – the systems within which buildings exist – how can even more “control” shape the way we live. I went further now this rabbit hole and completed a graduate degree in urban planning.

And it was when I shifted my career to urban planning that the complexity of leadership began to unfold for me because there is this thing called community and this thing called politics, and if you are attempting to try to harness interest from all levels of government, different industries, different geographies and economies to seek agreement on which way to go forward (which is a goal of planning) – a common way forward – this is no simple rote task.

It was in the development of the GGH Growth Plan in my role as the provincial Director of Partnerships and Consultation –responsible for designing a process to engage and bring along 30 municipalities, 11 transit operators, vested industries like developers, community activists and environmentalists, this wide range of interests all willing to take to the media to express their support or dissatisfaction – this was where I learnt that adaptive messy leadership could be a secret weapon.

There are many ways to lead a process to find agreement and paths to collaboration:

• Trying to lead from in-front requires you to be able to convince not just one or two people but hundreds to follow you (and if they don’t – well brute force is an option BUT –not always a winning proposition).
• You can lead from behind is also a lesser proposition – pushing from the back takes as much energy as pulling from the front, and it affords little transparency and can hamper you ability to see what is ahead.
• OR you can lead from the Middle it’s the most messy because you are working in the midst of everyone, trying to figure out what everyone is thinking and who they are aligned with and where is it they really want to go. Leading from the middle requires relationship building. YET it in my experience it can build some of the most lasting and loyal relationships able to carry you forward through even more difficult times. Its good messy/

I learnt about Leading from the middle from my mentor David Crombie – the former mayor of the city – federal MP and the most optimistic person I have ever met. He would always say don’t let a crisis go to waste – don’t let that destabilizing mess fool you – it is your greatest window of opportunity. A mess is an indication that all the known structures and systems are in disarray which means there is no better time to build something better and something new.

Crombie was also very deft at creating an open and seemingly chaotic tent for many. When he led the Toronto’s Bid for the 2008 Olympic Games we had a 100 plus person Board. I remember as staff we were totally afraid of the chaos that this would create. And it did BUT it also created and energy of massive connections, gatherings that strengthened the size of the City’s support to build momentum needed to get all three levels of government on Board. And some would ask why would any City want the bedlam of hosting a summer games. Well Crombie’s intent was not the summer games it was all a means to an end – it was the destabilizer to regenerate the waterfront. Cleverly he convinced three levels of government that win or lose they should all equally invest in the revitalization of Toronto’s waterfront. I had the privilege of leading the Bid book development of Venues, and Facilities (media village and Athletes Village) so I had a ring side seat to what it looks like when there is aligned mission and inter governmental cooperation. When people get along.  That folks is why we have the amazing waterfront we have today. That complete commotion got us that investment, the Bid got Vancouver the 2010 Olympic Games and it laid the ground – literally for the 2015  PanAm Games and legacy housing in Corktown.

I saw this play out in the mid 2000s when the public demand to have congestion and sprawl addressed (especially in the 905 areas) came to fever pitch. This crisis meant that there was a door opening to find more sustainable ways of growing – more density, smaller development footprint, stronger protection of natural lands and the ability to improve productivity and trade. If ever there was an opportunity for a step change, there it was.

In the “room where it happened” Mayor Hazel McCallion, Mayor Rob MacIsaac, Chair Bill Fisch, Gordon Chong, Deputy Mayor Case Ootes, Executive Director Deb Crandall, CEO Peter Gilgan, Commissioner Mike Murray and a few more – many of who you many never have heard of, were leaders with diverse interests, who found a path through collaboration, respectful debate, careful wordsmithing and intense negotiation to deliver  a policy and plan that held back sprawl for two decades. AND because they were each vested in this vision, it made the work even more enduring – surviving one change in government.

Make no mistake while I was responsible for setting out a clear and rational process for this crowd, grounded in facts and analysis, the creation of the actual vision could not be a prescription – it was much messier. Hallway conversations, group challenge exercises that went awry, we went through three facilitators, there were members of the public who tried to storm some of the gridlock meetings. BUT to be in the belly of the beast it was one of the many instances that I realised that data driven decision making alone is not enough. Rational structured logic is not enough. What does matter is far more organic and unpredictable – relationships. Being able to relate.

You can take a course; you can read infinite number of management books by leadership gurus BUT how you relate to others is what matters …… reaching individuals at a human level through patience and a commitment is what makes the difference between talk and action.  In the development of the Greater Golden Horseshoe Growth Plan and in the development – of the complementary regional transportation plan; The Big Move, conflicting interests, individualism and myopic views, moved to curiosity first BEFORE judgement.

Identifying mutual benefit can turn chaos into coherent action. It is important to understand that leadership in not about holding power. It is the ability to empower others to act and ideally act collaboratively.

These insights led me – during the pandemic – to leave a prominent career being a strategic lead for planning a multi-billion dollar infrastructure build– to head up a small not for profit, CivicAction. At CivicAction, as CEO I am responsible for building vici-minded rising leaders – with the capability to change our cities for the better –  Our organization is teaching a robust and diverse pipeline of leaders how to relate – and not just to people like themselves – but to difference – to people with more privilege than themselves, to people with less access and wealth, to people from different professions, different levels of government, different lived experience – access to the depth and breadth of the diversity of the country we are.

For two decades CivicAction has been bringing grass-tops and grassroots together to address the many crisis we are facing – We are issue agnostic. We have mobilized on arts and culture and founded Luminato.  Newcomer settlement founded Toronto Region Immigrant Council (TRIEC) ; Energy conservation with Race to Reduce challenge; transit investment (Your 32 campaign); mental health – Minds Matter program in partnership with Bell – youth employment (HireNext/Escalator/YouthConnect) – anti sex trafficking (Under the Influence campaign)– and today housing affordability.  In each case the model is clear

• Take a regional perspective that recognizes many issues cross municipal boundaries.
• Tackle both the economic and social issues facing the region together.
• Convene all sectors of civil society around the same table with leaders from the business community, the non-profit sectors, labour, and government.
• Be strictly non-partisan in all we do.
• Stay open and welcoming to anyone interested in getting involved.
• Commit to action—not reports just sitting on a shelf.

We mess Around. Doodle with ideas, test each other, respectfully and know how to create the safe spaces that nurture the trust needed to speed and scale the solutions to solve for wicked problems.

This is my story – and it is still evolving – I am not done yet. I still face challenges.  But that young woman armed with resilience and curiosity is still here with you today. A little grayer, a little rounder and occasionally a little wiser.  Each person will have to chart your own story – but  remember

• embrace the ambiguity for the opportunity that it is
• embrace change – even though it can be messy, tricky and  complicated

BECAUSE when we do this – that is when you know we are truly ALIVE!