John Weigelt is the National Technology Officer at Microsoft Canada where he works closely with the government, education officials, and health care communities to implement Microsoft’s strategic policies and technology efforts across the country. Prior to Microsoft, John worked for the Department of National Defence as the Senior Director of Architecture, Standards, and Engineering at the Treasury Board of Canada Secretariat.

Listen to this episode (or read the transcript below) to explore the strategies that John uses to convince large institutions to embrace change and adopt new ways of operating.

1 Who has been your most memorable or favorite boss?

The first boss I remember was when I was in the military after just graduating school and he was so calm and collected. Back when the Gulf War was happening there was a great partnership between the industry and the government and it was a very stressful environment and he was always calm, collected, and had an amazing ability to bring humour into the workplace.

2 When did you start to lead a team yourself?

I started out by leading a small group of people in computer security and it eventually grew to be a team of about 35 in the year 2k. I really learned the importance of letting go and learned that you don’t always have to put your stamp on everything to show up properly.

3 How do you ensure quality in a scenario where you aren’t providing the final stamp of approval?

It’s situational and completely depends on the scope of the work. I’ve had so many great opportunities to work with startups and innovators to work through really tough challenges and it’s essentially an art form to be able to balance everything and know what to ship when. Sometimes all it takes is having someone come in with the right experience to make those crucial decisions.

4 How do you successfully convince startups or innovators that they need to make a change?

Deloitte concluded that Canadian businesses want to maintain the status quo and we find ourselves having an extremely hard time trying to convince people to adopt new things. As much as we talk about digital transformation, technology, or innovation, it really comes down to the people because if they won’t change nothing will progress. I try to find a simple anecdote or metaphor that helps people understand the importance of embracing change and then try to give them concrete examples that relate to their business. I always try to deeply understand the business at hand so I can help Canadian businesses make informed decisions.  

5 Why is storytelling so important?

It’s all about identifying what’s in it for them. If you’re having a conversation as a leader or salesperson, it’s always extremely important to identify what drives the person. What motivates them? Are they motivated by self-fulfillment, financial gain, or maybe recognition? You have to identify what the particular things are that really jazz them up and then try to position your message in a way that speaks to those motivators.

6 What does it mean to build champions within an organization?

Champions always understand the organizational culture and they’ll understand any existing friction that exists within the organization so they can help others along their journey. Something I learned early on in the military was the importance of identifying a champion. It’s really important to get your bearings in any scenario and orient yourself by identifying your champion. Uneasiness within an organization will ultimately destroy the organization and identifying a champion early on will help with a more graceful transition especially if new leaders or initiatives come along.

7 Can you explain improv in the workplace?

Improvisation allows you to snowball on ideas which then allows you to be creative and open and it helps you open your mind to everybody’s concepts and everybody’s ideas. At Microsoft, we found that having diverse conversations really helps us create better solutions because we get to hear from the entire community and improv gives you the muscle and tools you need to be able to do that really well.

8 Are there any tips, tricks, or things that you would tell people on an individual level to help them understand that they need to change?

Change is hard and if you’re not familiar or comfortable with making changes on a regular basis or if you don’t frequently remind yourself to be open to change then you can get stuck in a rut. The first step is to get in the proper mindset. You have to be able to understand that change is continual. Secondly, you have to be bold and vulnerable by putting yourself out there by voicing new ideas or trying new things.  There’s also a lot of learning that has to happen along the way and learning will also help you embrace change. If you’re self-critical and seek feedback and input from others you will constantly be able to identify areas in which you can improve.

9 What role do you think AI will play in helping managers manage their teams?

There’s a lot of misperceptions out there around AI and AI taking over or displacing individuals when in reality, AI is going to complement and enhance human creativity. At the end of the day, leaders want to get the most out of their people. I think AI can complement the scorecards or metrics that fit into coaching and leadership. For example, AI may be able to recognize that during your weekly meeting, 90% of your team members are on mute so instead of interacting and being engaged, they’re emailing, and AI can help you identify which tools can help you provide a comfortable work environment where your employees don’t feel like big brother may be watching.

There are places where AI fits and it doesn’t replace or take over human interaction. We’re humans, we come into our work or social environments, and we form connections and AI can’t replace that.

10 What are some things that a company can do to ensure its leaders continue to improve?

Microsoft, we’ve shifted under Satya Nadella from a no-huddle culture to a learn it all culture so there’s a great deal of emphasis on learning but part of it is also about making sure that our people can do their best work. We want to make sure that we have an inclusive environment, and our goal is that our organization reflects the employees in our organization. We want to have this rich mosaic in the Canadian context or melting pot and we want to better represent the customers we serve because we believe that doing so really helps us create better products.

There is also a great deal of emphasis on the personal commitment that we make to learning and education, so we do have regular learning requirements around diversity and inclusion around dialogues across differences and then we have management excellence teams that come with quarterly learnings with group sessions with breakouts and a lot of interaction to talk about sharing skills and experiences.

11 Can you be a great leader and a pessimist?

I don’t think you can be a great leader and a pessimist. When leading teams, you need to be enthusiastic, and you need to be optimistic because you have to exude positivity. If you’re a pessimistic leader, you can never show that to your organization. Could you imagine being the leader in front of a troop that’s about to liberate a city and saying, I don’t think we’re going to be able to do it? You really have to be optimistic and say, hey gang, we’re going to be wildly successful, and then go forward with that and put in place the plans and the processes in order to support your mission. It’s important to never let your team see pessimism and you should always try your best to be optimistic and positive.

12 Do you have any resource recommendations or words of advice for managers or leaders that are looking to get better at their craft?

One of the things that I always try to remind myself to do is to listen or just be quiet. I tend to get vivacious or overly enthused and then I drown out other people’s opinions, which is a shame. As a leader, you need to be patient and we have to make listening a major priority so you can work on building the muscle that reinforces the idea of being patient and listening to your team. It’s also important to understand that there is never just one approach. There’s a time for coaching, a time for managing, a time for leading, and a time for discipline, and we have to understand which style applies to which situation while being flexible and accommodating.