Leading teams in the digital age

Shannon Ross
Ontario Digital Service
4 min readMar 20, 2019

In the Ontario Digital Service, people are the heart and soul of our work. To deliver user-centred products and services, we need people on the team who reflect the diversity of this province and are passionate about making it easier to get things done with government.

- Sameer Vasta

In 2017, our colleague Sameer Vasta spoke with people both inside and outside our team (the Ontario Digital Service) and our organization (the Ontario Public Service). He asked them their thoughts on leadership in the digital age and distilled what he learned into eight guiding principles of digital leadership.

It’s been almost a year and a half since we shared the digital leadership principles, so we thought it would be good to ask the leaders at the Ontario Digital Service how they’re putting them into practice.

Ontario Digital Service digital leadership poster.

Anna Oussenko, from our talent team, and I asked the users. We spoke with leaders and senior managers to find out how they’ve been putting the principles of leadership into practice with their teams

This is a summary of what we heard.

Using the digital leadership principles

Obsessing about the user is at the core of what teams do. Remember that we’re also users, even though we don’t always think of ourselves this way.

  • Remind, restate and focus on the purpose of what you’re doing for the user.
  • Build empathy maps and ask: “how would you feel” to understand people’s emotional and personal needs.

Agile and iterative methodologies can be used in lots of fields. Digital isn’t just about tech and the internet.

  • Break things into small chunks.
  • If agile is new to your team, find a problem, ask which agile principle can help to address the problem, implement it and reflect on the results.
  • Use consistent touch points to help people problem-solve and communicate priorities.

Working out loud is part of being agile. Rather than working in the open as a way of reporting to management, it’s about getting input and advice from the team.

  • Use collaborative tools that give people the opportunity to make real-time edits and share the link so everyone can make suggestions.
  • When you use collaboration tools, try to keep conversations on public channels so the team can share information and get wisdom from everyone on the team easily.
  • Remember to consider the sensitivity level of the information that you’re sharing when you choose a method of communication.

Use the data in daily work. This is a challenge and an opportunity for improvement.

  • Ask: “what does the data say?”
  • Qualitative information is data too; it’s not just numbers.
  • Data about the team is important too. Ask people to use a pie chart to share their tasks and draw pieces that show what portion of their time each task requires.

Be prepared to fail is a mindset that means getting comfortable with discomfort. It’s important to recognize positive failure and opportunities for continuous learning.

  • Hold retrospectives and ask: “what could we have done better?”
  • Recognize how often people need touch points to stay on track.
  • Help people know that it’s okay to not be okay.

Challenge everything, but recognize that there’s a difference in challenging thinking, practices, people and rules.

  • Ask open-ended questions to challenge outdated practices.
  • Create a safe space to challenge practices.
  • Challenge convention and ask: “do we need to do it this way?”

Embrace the chaos of the way we work because, in government, change is frequent.

  • Have trust in people and give people the benefit of the doubt.
  • Recognize that people have different styles, needs and work in different ways.
  • Share updates with your team as they happen, have check-ins and share info with staff.

Be unreasonably aspirational in everything that you do. We all have the same goal — to make products and services simpler, better and faster for people to use.

  • Don’t be content with the way things are.
  • Make people feel safe to try, fail and pick themselves up again.
  • Seek constant improvement; set the bar high.

Share how you lead in the digital age

We hope that these ideas inspire you to lead in new ways.

You can download the digital leadership poster as a PDF, PNG or collection of individual images.

The poster was designed by Lucia Hsieh. If you do print it out and put it up in your office, please share photos with us!

Thank you to all the managers and leaders who took the time to share your leadership practices.

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