Sideways… on ONWARD!

I just finished reading Josh O’Kane’s “Sideways,” which offers an in-depth look at the efforts for Google-offshoot Sidewalk Labs’ attempts to create a city in an underdeveloped area on Toronto’s lakefront.

The story resonates with me for two reasons: (1) I live (and was living) in Toronto as this unfolded, and (2) I was, at the time, teaching a Schulich MBA course that looked at managing stakeholders.

NOTE: If you are also in Toronto, and missed this, you are not alone. When I bought my copy, the person at the cash register exclaimed, “What? Google tried to buy a city?!”

It was fun to see familiar names among the cast listed. Some had local celebrity status, and other connections were closer: I have had the good fortune of spending time with Valerie Fox. Not mentioned in the book, but close the action was my friend Steve Trumper who was the counsel to CreateTO. He was generous enough with his time to offer a guest lecture to my MBA class that included some of the late-process collateral that shared big ideas (e.g. subterranean garbage collection) and was criticized by being short on details.

Revisiting some of that time of local history, here are a few lessons that I will feature:

Aligning interests:

Working with partners involves a gentle dance of learning and sharing. We can sometimes get a sense that other parties are not forthcoming with their interests, objectives, or agendas. This is worth noting. Lack of clarity might mean they are hiding something but could easily mean that they are not clear themselves. Transparency around opaqueness does not become clear. The latter state is one to avoid by clarifying priorities internally.

As another notable observation, the feeling of not being able to be straight with fellow collaborators should give time for reflection and discussion. The question, “Why do we have to be less-than-direct/secretive about what we are trying to do?” would be a great way to start an important conversation. The future is a very uncertain place, but we may be able to agree to proceed in a similar direction.

Playing roles:

Situations like the Sidewalk/Quayside drama highlight the different roles involved and the constraints that come with playing those roles.

·         Waterfront Toronto, a government agency, served three levels of Government, municipal, provincial, and federal. This can bring frustrating bureaucracy.

·         Sidewalk Labs was a subsidiary of Google/Alphabet. This will bring an orientation to money in two ways: an assumption that money buys friends and that, in the end, we will make a good return on our various investments and up-front costs. Some wheels need grease. Frames and guardrails can benefit from being tested.

·         Advocates, academics, and critics played a role. This brings a philosophical rigidity and tries to impose an idealistic moral compass. This can clarify some fundamental distinctions to which all can agree.

NOTE: The role of “community” or “people who live in Toronto and will deal with the aftermath” are harder to cast because, as evidence from my bookstore interaction, many have their own lives going on and can’t be expected to invest the time required to understand what is going on. This is neither a criticism nor a call for greater civic involvement. It is an acknowledgement of the role.

It is easy to criticize any of these roles, but that criticism is best positioned as “too much of a good thing” (or “not enough” in the case of the civic involvement.) Bureaucracy can bring legitimacy. Competitive practices can test boundaries. Philosophical purity can clarify important distinctions. Trying to eliminate any of those roles is not a realistic approach to how such projects actually work in setting up a sustained success.

Framing and retelling:

Josh O’Kane reveals a guiding principle of Dan Doctoroff’s as being that something is only a failure if you allow yourself to frame it that way. “Failure” can take different forms, but any reflective look at a situation that did not work out the way we wanted can offer opportunities to learn.

If the reflective questioning starts with, “Why was none of this our fault?” the opportunity to learn is much diminished because we get back to assaulting some of the roles that we cast above.

As I get older, I develop a great appreciation of history. This may be because more and more of it I am experiencing firsthand. Things of great potential and impact often require engaging with others who play different roles and may make our lives a bit more difficult. Framing those difficulties as constraints to work within rather than annoyances that they should just drop, follows that belief that innovation and wisdom are a function of adhering to constraints that would eventually diminish our overall impact (or get in the way of us being allowed to even start!).