What does winning look like?

Honey Dacanay
Good Trouble
3 min readNov 8, 2022

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On how it feels like digital teams don’t win most of the time, and so we celebrate our victories, however small they may seem.

Background: Five years ago, Katy Lalonde, Katherine Benjamin and I pitched a talk to FWD50 because Ontario didn’t have a learning budget and we really wanted to attend this conference. Our approach was to offer three different perspectives about a particular digital government theme — Katy about product, Katherine about design and me about policy and governance. We have been returning every year since.

This year’s FWD50 presentation gave us an opportunity to unpack our respective teams’ wins and reflect on digital transformation writ large.

But first (and always!), celebrating our teams

While personally daunting to be onstage, it is a privileged position to take the spotlight and speak about our teams’ accomplishments. This post, like our presentation, is dedicated to them and, in equal measure, all those teams before them that have paved the way and made the good path (relatively) easier for them.

Team Verify, Ontario Digital Service

Photo of the Verify Ontario team on a video conference, dressed up for Hallowe’en as government decisions (go, stop, proceed with caution / course-correct)

Verify Ontario was built by a multi-disciplinary, cross-ministry team from the Ontario Digital Service, Ministry of Health and the I+IT org, as well as a team from MLSE.

The team did user research, developed and launched the Verify Ontario application in 40 days.

Team Agile Governance Pilot, Service Canada

Team photo at FWD50, from left to right: Aaron Jaffery, Honey Dacanay, Jordan Storozuk, Jane Lu, Gigi Chang, Lindsay Chan, Daphnée Nostrome

We were fortunate to have had many members of the policy team be there in person at the FWD50 conference. Members past and present in photo, left to right: Aaron Jaffery, Honey Dacanay, Jordan Storozuk, Jane Lu, Gigi Chang, Lindsay Chan, Daphnée Nostrome. Other members not in photo: Ashley Evans, Sarah Ingle, Dolly Theodore-Latchman, Wafa Bettaibi.

The team secured policy approval to test a large-scale agile governance approach to service delivery for digital teams

Team Mayor’s Office of the Chief Technology Officer, NYC

Members of the Mayor’s Office of the Chief Technology Officer, New York City, USA

Members of the team include the entire New York City Mayor’s Office of the Chief Technology Officer and the New York City Housing Authority. Special shout-out to Mayo Nissen, Elyse Voegeli and Rapi Castillo for their design and development work, and to the Mayor’s Office of Immigrant Affairs for translation support.

Applying experience design considerations, this team collectively distributed 10,000 internet-enabled tablets had been delivered to older adults living in New York City Housing Authority (NYCHA) developments

This year’s presentation

Katy, Katherine and I took turns presenting our respective case studies and answering three questions from each of our perspectives:

  1. What’s the win?
  2. Headlines (or approvals) don’t drive transformation. What’s the actual win?
  3. Thinking more broadly about digital transformation, what are the winning conditions for teams? Is winning even possible?

Special thanks goes to the Ontario Digital Service (our common starting point) for faithfully hosting a dry-run for our trio in the lead-up to our presentation each year.

Continuing to hope and create space for it

As topics go, this was by far the most challenging one we have had to consider. “Do digital teams ever really win?” was a top-of-mind question we asked ourselves and each other even as we planned and rehearsed our talk. Ultimately, we opted to share candid lessons learned — as our teams would have wanted — and celebrate with the quiet confidence of knowing that there is even more impactful work ahead.

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Honey Dacanay
Good Trouble

Professionally awkward. Digital government and public admin nerdery.