Sid Tobias, Director, Digital Standards Office for the Ministry of Advanced Education and Skills Training, joined Cascadia Report to share some perspectives from his impressive career and what the future of digital development and digital leadership looks like at the BC Government.

Sid describes himself as being passionate about evidence-based decision making based on data analytics, artificial intelligence, complexity theory and advanced modelling. He is driven by real problems that require urgent, no-fail, leadership. He has mentored several Agile DevOps Teams within the BC Government including BC Wildfire Predictive Services, MyRangeBC, Water and Invasive Species. He mentors new digital teams in concert with the BCDevExchange and teaches Digital Leadership to executives. Sid takes decision making seriously and focuses on loving the problem and investing heavily in creating the conditions for small, specialized teams to solve significant problems.

He has 25 years with Canadian Armed Forces working with Naval, Joint and Combined Forces. In his time with the Forces, he was a specialist Joint Interface Control Officer, Canadian Joint Tactical Data Link Coordinator, Coxswain of HMCS OTTAWA and Chairman of NATO Tactical Data Link. In 2011 he was awarded the Meritorious Service Medal by the Governor-General of Canada for his professionalism, technical expertise, and leadership for developing a new integrated data link in support of NORAD and the 2010 Olympics. He has been formally recognized for his work in leadership by NATO, ASIC, Hungary, Poland, Greece, and Canada.  He is quick to admit that none of his accomplishments would have been possible without exceptional mentorship, leadership, and the outstanding support of international teams.

Sid joined the BC Public Service in 2015 and has recently assumed a new position as Director of Digital Standards at the Ministry of Education, Skills and Training in September 2020. He has successfully handled a big change in the direction of his career. I was curious to discover how he found the transition from the Canadian Armed Forces to Provincial Government, and what he enjoys about his new role.

Sid Tobias

“The shift has been great. I love that I can bring my experiences and my failures into the job and work with phenomenally talented and passionate people around solutions that make a real difference for the public in British Columbia. Creating future leaders that can be effective under demanding and complex circumstances is what gets me up in the morning. It also is what sometimes keeps me up at night, wanting to ensure that we're supporting new leaders as well as upskilling seasoned leaders in new ways of working.

The Digital Framework for the BC Government is relatively new.  I had an incredible opportunity working with a forward-leaning team with Natural Resources to experiment with Agile, DevOps, User Research, and human-centred design in the days before we had this strategic guidance.  For many seasoned leaders, understanding the new ways of digital delivery are challenging.  It is a significant change from traditional software delivery.  It requires a new way of leading and a move from a command-and-control leadership model that is focused on output to a trust-based model that is focused on outcome.  The digital leader is not expected to be the specialist or authority but rather the coach that forms the team and encourages self-organization and cross functionality.  The tolerance for risk also is a marked difference.  Digital leaders encourage the team to experiment with solutions and learn from failure and even share the failure so other teams can benefit.

I've had the fortunate opportunity to join with a CIO that has remarkable foresight, Marlowe Stone. She is very supportive in integrating the Digital Framework and partner with other Ministries, institutions, and agencies like the BC DevExchange. It's okay to set strategic direction, but the hard part is to implement it.  One of the strengths of my military experience was an almost sacred opportunity in an after-action debrief where folks were honest with each other about their performance and expectations of others on the team. Many of the teams I work with now do a very similar activity.  The cycle of continuous improvement becomes deeply entangled with the success of the product they are building and stimulates individual growth and improvement.

My focus recently has been creating an exemplar of a product team that through setting the right conditions inspire a high performing team that is focused on a complex problem. Through the journey of this team, we can reflect on continuous improvement and generate mindful questions. What can we learn from the process as we're rolling it out? How can we learn utilizing the lessons and advice being generated by other Ministries and Governments? And how can we acquire and incorporate success in our own unique culture within Advanced Education, and Skills Training.”

A key part of Sid’s philosophy when it comes to work is the idea of coming to ‘love the problem’. I asked what that phrase meant to him in a practical sense, and what it could mean for his work with the BC Government.

Often, we skip over things because if it's a problem then it’s difficult, and we want to fix it quickly. If we embrace the problem what we're doing is getting more human about it and its root cause. If you feel that you've got a solution, implement it quickly and then move on to the next one you don’t gain a lot from the experience because you don't want to learn about it. You shut it down and move on to the next thing.  What keeps me up at night isn’t failure…it is failing for the same reasons or watching others fail for the same reasons.  We need to share our failures and our problems to learn from them and see the adjacent possibilities for success.

You need to ask some hard questions like, what's the root cause? Are all the problems I've seen related to something else? Sometimes it takes a life-shaking experience to say, ‘let's take our time here, even though it's uncomfortable. Let's take some time to make sure we're happy that we've got things resolved and watch it closely to ensure that we are understanding new problems that a solution can bring.

Seeing some of our Agile DevOps Teams react within a week and have guidance websites up in response to COVID for example. I don't think we could have done that before, without that new approach to looking at the problem. The teams then shared open-source code and components making it easier for the next team to replicate the success”.

As someone with a distinguished career, I asked Sid about some of his career highlights to date, and what he attributed his current position and success to.  He mentioned how it takes a significant ‘life-shaking’ event to fundamentally shake the foundations of the way we think and the way we lead, I asked which moment triggered this realisation for him.

“Shortly after being deployed in the Persian Gulf in 2002, we had a friendly fire incident of an American F16 dropping a 500-pound iron bomb on our troops' position in Afghanistan. I was responsible for the technology to fuse the situational awareness in an operations room on a destroyer, for the theatre that I was in. I could see through relays the position of the jet, and I could see in other systems, the position of the army units. But our Canadian Army units and the jet could not see each other.  The pilot interpreted a night firing exercise as a threat and applied a weapon to their perceived target. It is always bad when you lose people in a conflict, there's no question about it. But it's worse when it happens between allies, especially close allies, with Canada and the US. The truth is we had not trained very much in large scale joint and coalition operations at that point.  Nor did we have the technologies and procedures to support it.

What drove it home deeper for me was when I received an advanced medal for Southwest Asia. The families of those folks that died because of the incident at Tarnak Farm were receiving it posthumously…many of the families were young. And so, I said, ‘we've got to be able to do this better. What's the cause of the problem? Why aren't we better able to be interoperable?”

The public is expecting that when we go to war together as allies, we don't drop bombs on each other. So, I spent the next decade diving into that problem.  I worked incessantly and dove deeply into the problem.  I completed a Graduate course in Knowledge Management and Masters focused on discovering the root cause and developing solutions with small teams of specialists.  I was writing my thesis and assignments at 35,000 feet over the Atlantic whilst working as a Head of Delegation for NATO and later as a NATO Chairman for Tactical Data Link. I didn't love the problem, the story behind it was heart-wrenching, but I had to find out what we could do to change things, so it did not happen again. It simply was not good enough to hope for success.  I am very grateful for the trust my leadership empowered me with.  When I said I needed to experiment, they supported me.  When I admitted I failed, they asked me to share why and how can we not fail again. Eventually we started to get it right.”

Sid Tobias at the NATO Data Link Congress in Greece

It’s a sobering tale that can serve to remind us how lucky we are, whatever problems we are facing in our lives and careers. Sid’s dedication to tackling the problem head-on and ensuring that he addressed not only the unfortunate result but the root cause to prevent it from happening again, marks him out as a truly remarkable person.

“What I found is that the Canadian army was probably more interoperable with the American army at the time than it was with the Navy or our Air Force, and the same was true of the Navy. Joint Interoperability was introduced to make things work together and integrate Special Ops with the traditional three. It was an exciting time, but the challenge made it worse, especially as the tempo was increasing in both Afghanistan and other operations.  The complexity and speed of the roll-out of new technology in support of these operations was unprecedented and the separation between new technology and old was causing significant challenges in maintaining situational awareness.

My specialization was the Tactical Data Link - you have probably seen movies where they are tracking targets on a radar screen. I became a specialist Joint Interface Control Officer (JICO), trained by the US Joint Forces Command. The role of a JICO was to set up and manage a theatre using the Tactical Data Link umbrella that involves satellites, radio communications, and secure networks. There was a constant change in positions and units that ensured the dynamic network was always challenging.  When it all came together it was a game-changer - it evaporated the fog of war.  My father cleared mines in WWII on a wooden minesweeper for D-Day and he often talked about the ‘fog of war’. He said how on a good day you could see 12 miles while on a bad one you could barely see your hand in front of your face.  Now, you have a system of systems that enable you to see thousands of miles.

Whilst I was gaining more experience as a JICO and doing graduate studies I was nominated Chairman at NATO for Data Link, and then was the Joint Interface Control Officer for the 2010 Olympics, setting up the tactical network there. And of course, the immersion of new technology with, the legacy was a requirement to fuse both of those kinds of worlds. We were able to do some things and experiment with them iteratively over about three years in the operations zone to see how well they worked and then provide that feed into NORAD to aid decision-making and consequence management.  We did it with small teams of very talented folks and instead of having a Canadian Navy cell, we mixed it up bringing the best US and Canadian folks together iteratively improving and communicating success and failures”.

The next step in the journey would be a transition from a decorated career military service to the public service with the BC government. Preparing for that transition was no easy task, but he approached it with his typical professionalism, dedication, and a willingness to adapt.

“As part of my work in Knowledge Management, I focused on team learning and collaboration, being able to talk to other people doing the same thing, being able to honestly share failures. A lot of people are good at sharing their successes or not so good about sharing their failures. Honesty was perhaps the thing that bound likeminded practitioners together.  By facilitating some boundary conditions around smart passionate people, the conditions for good ideas and capabilities to collide is like magic”

I joined the public service about five years ago. I left the military on a Friday and I started on Monday. It was the biggest culture shock I had in my entire life. I left the military as Chief of a destroyer and joined as a transformational specialist to assist a very large project. I then went on to work in close cooperation with the BC DevExchange Lab in nurturing talent.”

Sid speaks with real vigour and pride when the conversation switches to the subject of instruction and training. He is passionate about his role ‘teaching digital leadership’ and is keen to point out that they are making a tangible impact on how teams from the BC Government tackles problems.

“We've trained almost around 200 public servant leaders in a new way of thinking about problem-solving. And all of that's been rewarding to my recent appointment as the Director of Digital Standards, Advanced Education and Skills Training. It's been a path that converged on all the things that I don't necessarily love doing. But I see the necessity to work harder to communicate and listen to emerging challenges.  I learn from others every day and incorporate the success and failures in the course.  I invite Product Owners with powerful stories to share with the course.”

Sid Teaching Digital Leadership Virtually

With the initial honeymoon period now firmly out of the way and the ‘culture shock’ behind him, I asked Sid how he had been able to apply his experience in the Navy to his career with the BC government. What synergies had he been able to find, and how has his approach to leadership changed over time.

“…I don't remember giving a single order in the military, aside from being on a parade square. It was more working with smaller teams and doing everything I could to let them solve the problem. I learned early on that it was better to ship the problem than the solution. If you can leave the solution open, then smart folks can own the solution for themselves.  This is a lesson I am still learning. It is hard to keep your hands off when the team may be at risk of failure, but you have to let them work it out for themselves.

If you're the type of leader that put a lot of constraints on delegation, there's not much opportunity for innovation. Nobody is coming up with the new way of doing things or seeing things in a new light that might add some real value to solving the problem. Part of it is the ability to transfer what I don't do and be happy with moving from a command and control-based governance structure to a trust-based structure. In my opinion, you're not a very effective leader if your number one job at some point in your career isn't to create better leaders.”

It’s no small task that Sid has set himself, but I wouldn’t bet against him succeeding in his mission. While training the teams is one of his passions in his new role, Sid makes no secret of the fact that executive coaching is more challenging. I asked him how the work fits the broader scope of the Ministry of Advanced Education and Skills Training, and how he has approached it.

“It's easier to train agile teams than executives sometimes. I've been with senior government executives, talking about complexity theory and why you wouldn't use a process that was meant for manufacturing, for a complex emerging problem like user research or COVID. Leaders want tangible milestones that measure output. It gives them a sense of controlling risks and resources.  Investing trust in a team to adapt to the changes in technology, feedback and the unknown requires deeply questioning how we think about a problem.

All executives want to do a good job and ensure sound decision-making around the expenditure of public funds, particularly around IT. Sometimes it’s uncomfortable for them to assume too much risk. Agile development and failing fast flies against the face of the traditional project management approach of having everything laid out and agreed to as a plan. They are used to having a risk matrix and seeing the problem and documenting it without trying it first and maybe failing. So, we're seeing a different approach and we have had some incredible leadership and inspirational examples at all levels.”

There’s no doubting that old habits die hard. Challenging the established way of doing things in and encouraging innovation in leadership is just one more challenge along Sid’s path. I asked why he sees the shift to Agile methodology as so crucial going forward.

“If you have your plan made up and signed off two years before you go to production or release, and it was designed two years before that, you're eventually delivering yesterday's technology today. You don't want to do that; you want to be flexible enough to ship something a bit more enduring through iterations. You can't predict how people's expectations may change, so while your requirements were gathered two years ago, you must keep up with the research needed to put out a product that is valuable and useful now and - through continuous improvement and delivery - the future.

The other mindset is an engineering philosophy; you develop a product, it has a life cycle, and it goes away. What we're seeing now in the field of Agile, DevOps, and human-centred design, is something that's closely linked and that's a continuous integration and continuous delivery. You need the product team to enhance what you've already invested in and keep it relevant. That way you're staying up to date for privacy concerns and security bugs. A lot of the product teams that I’ve worked with can develop an MVP rapidly and roll it out iteratively. There's no big bang. Within a year or so, they're moving onto their next product whilst still maintaining the continuity of the initial product they put out there.”

Many of our readers will no doubt be familiar with this process, and it is heartening to learn that the BC government is moving to embrace modern methods in software development. I asked Sid if he could explain a bit more about what it looked like in action.

“I tried an experiment while I was at the Lab working for the Information Innovation and Technology Division for the Ministry of Natural Resources. I was able to put together an all-government team to start off with the Lab, they were able to rapidly put out an MVP for BC Wildfire Predictive Services and then move on to new things.

I was looking for opportunities to give the teams an experimental sprint - two weeks where you identify a problem that matters to you and come up with a solution. The only caveat is you've got to describe what it is, what you expect the outcomes going to be, and you've got to have something tangible to demonstrate it in two weeks. The team embraced things like integrating artificial intelligence to wildfire prediction and forecasting and modelling. It was staggering what they were able to achieve within two weeks because they were passionate about it.

One of the architectures that have been amazing for me is collaborative architecture through a medium like GitHub. Teams collaborate with other developers before they post and come up with their notion and then be able to share it, it's almost like an academic or scientific review of publishing in a journal.

The sense of community between teams ensuring collaborative code is coming to the fore. You know you’ve got something good if you have a lot of requests to share your code. Whether it's an opportunity for developers, leaders, or developers who would become leaders … developing those skill sets and being comfortable with allowing folks to try is the basis of getting better.”

During our brief Zoom call, Sid spoke with a composed assuredness of someone that has lived a life full of challenges but who always looks for the positives and possibilities. It appears that learning to love the problem has enabled him and the teams he has led to achieving some incredible things.

Before I let him go, I asked for three key takeaways from his journey so far.

1. Never pass a fault, if you notice it then it is your responsibility to fix it.

2. Build teams and set the conditions for them to be cross functional and self-organizing.

3. Invest in building new leaders that will surpass you in ability.

You can find out more about the Ministry of Advanced Education and Skills Training here: