Anna Chif on McKinsey, AI, and Dialogue’s mental health product

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This episode features Anna Chif: Co-founder and Chief Strategy & Product Officer at Dialogue, Canada’s leading telehealth company. Dialogue provides progressive, premium and affordable virtual healthcare to Canadian businesses for their employees, accessible on mobile and online. This past summer they raised a $40M Series B Financing Round to expand to other markets including Europe.

Dialogue is growing rapidly and currently hiring for a ton of positions: you can visit their careers page here.

Previously, Anna had founded Anna Cuisine, which was a healthy meal delivery service. And before that, she was at McKinsey.

Topics discussed: transferable skills she developed at McKinsey, lessons she learned with her previous startup, the founding story of Dialogue, how they’re using AI, and the mental health product they recently launched.


Mo: I want to start at the beginning of your career. Right after you graduated from McGill, you went on to McKinsey. What are the top two to three skills you learned there that continue to serve you as Chief Strategy and Product Officer at Dialogue today?

Anna: I think the first thing I’ve learned is this idea of taking a very complex problem and deconstructing it into smaller bite-size pieces and solving one piece at a time to then get to the solution of the bigger and more complex problem. I think that’s applicable both in a startup but also in my life. Whenever I’m faced with something that sounds huge, I typically go, “Okay, what is the first step? How are we solving this? How are we structuring this? Then how do I go about solving it?” I think that’s definitely something I took from McKinsey.

Anna: The second point is around getting to the real insights of whatever information that you get. If we ask a question and we’re looking for an answer, I think it’s really important that we always ask ourselves, “Okay. So what? What does this mean for us?” If we’re looking at competitive landscape, for example, today and we’re learning something, “So what if somebody is reducing the price? What does this really mean for us? Is that because their product is not as good as ours or is that because there’s a competitive pressure in the market?” and depending on the answer, the way you react to it as different. I think pushing ourselves to always get to the last why is that important is also something that McKinsey has always focused on.

Anna: The last one is around surrounding ourselves and myself with really amazing, incredible people. McKinsey goes over and above in hiring outstanding talent. That is why the company has so much success. I mean, the first process we’ve ever put together at Dialogue, we were still just a few people, we didn’t have a name, and we had a hiring process that was structured and lengthy and selected for eight players. I think that our success today is a result of the high-quality team that we’ve put together.
Mo: Thank you. After that, you did go on to start this company and many students would like to start a business one day, but not right after graduation. For those students, how highly would you recommend consulting and why?

Anna: Yeah. Look, I mean, consulting worked for me and I wouldn’t change that experience ever. I learned a lot. It wasn’t an easy experience all the time; there was a lot of skills I had to develop. Working with outstanding people really pushes you to get better fast. That, to me, was really great because that’s something that still follows me today.

Anna: Now, the risk of working with outstanding people and being in a very prestigious position is to stay too long. I truly believe that you become what you do. If you stay there too long, the alternative of going back to starting from scratch and going from a very prestigious job to being on the phone, calling your first clients and no one wanting to buy from you is tough.

Anna: The longer you wait, the harder it becomes, so I would say for those entrepreneurs at heart who do decide to go to a consulting firm: Don’t stay there too long. Or keep yourself honest, that you need to get out and test something. You always have the option to go back, I think, but yeah, I think remaining true to that passion of starting a business is important.

Mo: Now, for a few years now for a few years after your time at McKinsey, before Dialogue, you built a company called Anna Cuisine. Can you think of any learnings from building Anna Cuisine that helped you avoid making similar mistakes at Dialogue?

Anna: Yeah, I mean, so many. That was my first real entrepreneurial experience and I mean, all my first instincts come from there, from hiring incredible people and also letting them go or firing.

Anna: I remember the first person I fired, it took me three weeks and I remember for two weeks, I lost sleep over it and I was so nervous. Then you realize that some people just don’t work out. Not everyone is fit for every job and you realize that sometimes it is an opportunity for the other person to move on and do something else, so that was one of the learnings for me, for sure. It’s something that you develop in your career.

Anna: The second one is the benefits of just hustling and being creative about things. I remember at some point we were looking for a central kitchen to assemble the food and then deliver out of it. I was like, “Where do I find a central kitchen?” Nothing really available online.

Anna: One day, I was driving in my car and I saw a truck that had some catering brand on it. I was like, “Well, surely if they’re doing catering, there’s got to be a space they’re working out of, so maybe I can ask them.” I followed that truck up until where they went. Then I walked in and I was like, “Hey, can I speak to …?” I can’t remember who I asked; maybe the president or maybe… I don’t remember. I was like, “I need to speak with someone.” I ended up speaking to the president of that catering company and I got a central kitchen out of that, so that was great. I just think that sometimes following our gut in some of these things that sound weird or crazy can actually lead to so many benefits.

Anna: Then the last one is I read this amazing book called The Lean Startup, which I really recommend to all entrepreneurs. It helped me not… The idea behind Anna Cuisine was to launch restaurants that were healthy, delicious, and mostly automated. Before doing that and having read that book, I actually decided to start deliver food and actually see do people even like it and so on. This notion of iterating on an idea and on a process is the third thing that I think was a really big learning.

Mo: Okay. Now, I want to move on to the founding story of Dialogue. First of all, why did you found Dialogue?

Anna: Yeah, I mean, when I think back to the beginning of dialogue, I really think about it as an alignment of stars. Diagram was getting started, telehealth fit within their model. My cofounder, Cherif back then was interested in doing something else. I mean, he was getting, he had a startup in the health, that tech space. Then he was looking at other things.

Anna: At the beginning, I was just giving a hand until I realized that this was it. At the same time, I was taking care of a family member who was in palliative care. I remember how hard it was for her to receive care. When we had questions, there was no advice provided on the phone by her doctor and when she needed to get seen, we had to bring her to the emergency room, which was extremely inconvenient.
Anna: I think that was the motivator to me personally back then, but I think today it’s still something that still motivates me. We have hundreds and hundreds and hundreds of patients every day. Sometimes I think about it, I’m like, “Some of these people wouldn’t have had an alternative otherwise.” I think that’s still to me, personally, what gets me up and going every single day.

Mo: Could you quickly describe Dialogue for people who don’t know about it?

Anna: Yeah. Dialogue is a telemedicine platform. In most basic terms, what it is, it’s an application that allows for an individual to consult a medical professional via an app within minutes. Those professionals are nurses, nurse practitioners, doctors. Somebody starts, goes onto the app, completes a quick questionnaire. It’s actually an AI-based questionnaire, so we remove this notion of human bias as part of the diagnosis.

Anna: Then patients see the right resources. Somebody who comes in and, let’s say, has pain somewhere, will see a doctor. A new mom will come in for breastfeeding advice, she’ll see a nurse. The patient basically gets redirected to the right next step. Then we always follow-up on all medical issues to make sure that we close the loop.

Anna: For people that we can treat virtually, let’s say, we do need to look into your ear or listen to your lungs, well, we have a team in place that will redirect these patients and help them find an appointment in a clinic or provide kind of advice on which emergency room to go to that has the least wait times.
Anna: In a nutshell, that’s a service. That’s a service that’s available only to employers and as offered by leading employers as a benefit to their employees and their family members.

Mo: Now, earlier you talked about Diagram. Could you quickly describe a Diagram Ventures and what role they played in helping Dialogue?

Anna: Yeah, Diagram is a venture creator. What that means is that they would often have an idea, MVP it, or iterate on it and then assemble a team around it and that team actually takes that idea and deploys it or they start with theme and there’s a team that’s assembled and then they help kind of bring that idea to market.

Anna: The way they do that is, obviously, capital is one. Just like a normal VC, they would invest. What’s really interesting is that their seed investment is there’s a set amount, but it’s deployed based on your ability to attain certain milestones, so it keeps you accountable and moving with a good pace.

Anna: They also provide resources, so we had help on strategy, on recruitment, and also all other kind of resources. We had their CFO who helped us with our very first financial models before we even had a team internally. Their head of talent recruited probably the first 70 employees. There’s the resource component.

Anna: Then the last one is opening doors, opening doors with insurers within companies, and so on. We could test our product with their help in getting to some clients.

Mo: Okay. So at the time of this recording, it’s the end of November, but in October, so just about a month ago on World Mental Health Day, you launched phase two of your mental health program. Could you talk about that a little bit?

Anna: Yep. In addition to having the primary care telemedicine, we launched a specialized mental health program. The reason we started even thinking about it in the first place is that a lot of our clients started coming up to us and saying, “Hey, our employees are using the service. They love Dialogue. We have this additional problem where our disability claims are going up, primarily driven by mental health issues. We’re offering yoga during lunchtime and all sorts of other flexible arrangements, but our mental health issues are not going down. What can you guys do?”

Anna: Back then, we started researching what truly reduces and drives improvements in mental health. We’ve built a program following the best practices that we found through research across the world. What it is is the program starts with a screening of all employees. Then for those employees who need mental health support, they have a multidisciplinary team that follows them up until remission or until symptom improvement. That could be doctors, psychotherapists, nurses, whatever the right mix of people are. They all communicate to adapt treatment in order to accelerate improvement for that patient.

Anna: If you think about the public system today, often you have to search for your own psychologist, you have to search for your own doctor, they rarely talk to each other. This is all about having a close-knit team that follows the employee, but also an assigned case manager who follows up with a patient every single week to know how they’re doing.

Anna: We remove this notion of willpower, so we’re not counting on someone’s willpower when they have depression. We’re going to follow-up every single week. We’re almost like an accountability partner, we’re a friend on the other side that really cares, and that’s very, very positive in terms of bringing someone to remission quickly.

Anna: That’s the mental health program. We launched it with a few clients for the first year and now the program is available to any employer.

Mo: Okay. Earlier you mentioned AI and recently, you announced you’ll be expanding your AI-powered clinical decision support technology internationally. Can you tell us more about that?

Anna: Yeah, absolutely. We acquired, well, over a year ago now a tool that allows for a smart triage in diagnosis. That tool was built by four emergency physicians based on over 16,000 peer-reviewed articles. The goal is to remove bias when triage is done. If you think about doctors making a diagnosis, there’s actually better or improved percentage of a doctor making the right diagnosis if they’re in a better mood, if they’re less hungry.

Anna: If you can imagine diagnosis today, there is some human bias, so the way that our intake or our triage is set up is to remove that bias. Sometimes we ask questions that can cover very rare conditions that maybe don’t come top of mine but so that way when the patient gets to the doctor, they actually have a summary of what was said during that triage and potential recommendations.

Anna: This also allows our nurses to dispatch the person to the right next steps, so somebody who needs breastfeeding advice, as I was mentioning earlier, doesn’t need to see a doctor, but they need to see a nurse who has worked with parents or with mothers in the past who can help. That’s the first one.
Anna: I mean, our tool is used in the CHUM, that’s the largest emergency room in Quebec. We do have plans yet expanding this tool international. There’s a lot of interest in it across the world and I know that we’ll be growing with that in the future.

Mo: The last topic I want to touch on is education. You mentioned reading and loving The Lean Startup. Can you think of some other examples of ways in which you continue to invest in your own education?
Anna: I mean, working in Dialogue is a great education, but, no, I think above that, I love reading, I love books. There’s actually an app that truly changed my life and it’s called Audible. It’s basically audiobooks and you can fast-forward it and listen to it fast. I am very auditive, so I actually registered a lot of information by listening. When I go for a run, I listen to books, when I go for a walk or walk over to work, I listen to books, and that has really been something that has been a big plus since discovering that app over a year and a half ago. I was able to, I don’t know, maybe 30, 50 books, and that’s not a pace I was able to keep up when I was just reading physical books. I think that’s the main one. You can cover so many topics and there’s so many books in that app, so that’s definitely one.

Mo: Please, make some recommendations. What were some of the books that really had an impact on you, whether they’re fiction or nonfiction?

Anna: Yeah, okay. So many books. Some of the recent ones, one is a book called Getting Things Done, it’s a methodology on being productive and capturing everything that you want to do, both present but also future and potential. He calls it “someday maybe opportunities,” but all those things as entrepreneurs you want to solve so many problems. He actually has a methodology to not forget any of that and it’s great because following that methodology makes you 10X more efficient. That’s one.

Anna: Another one for people who do go into tech entrepreneurship is a book called Inspired by Marty Cagan. It’s around product management. It’s about the method of product management, but I think it’s a lot around product development, how to iterate and test ideas, so that’s a really good one.
Anna: Let’s say a third one just so that I get to three at least. There’s a book called Atomic Habits; it’s probably the best book I’ve read around setting habits and sticking to them. It’s much more around working on your identity and how to decide what you’re doing and setting very, very small, regular goals rather than setting big objectives such as, “I want to run a marathon,” and then you get to that point and then you’re done. Atomic Habits by James Clear is a third one.

Mo: The first and third one, I think everyone will totally understand. For the second one, can you describe what a product manager might do at Dialogue?

Anna: Yeah, a product manager, think about it as a mini CEO within a company. It’s somebody who is accountable for the success of a product. Think about it at Dialogue, for example. Let’s talk about a product manager for the mental health program. Well, your job is to think about the PnL: How much revenue am I able to generate with this product? That means working with a sales team, making sure there is enough training material to train that sales team, preparing the materials and so on and going into sales pitches.

Anna: Then it’s all about executions and costs. From an operational standpoint, what is it? How do we measure it? It’s also looking at competition and defining what are we doing, what are we not doing. It’s about positioning it when we speak about it in the market or to clients, but also in conferences.
Anna: It’s really someone who thinks about every single function and how that product will be supported by every single function and making sure that the efforts are coordinated and then also working closely with the tech team in order to make sure that there is a clear plan, there is a roadmap for that product, it evolves, and that there’s enough technical resources that are working on it, what does the roadmap and timeline look like.

Anna: It’s a very broad and complex role, but I know that there’s a lot, a lot of really brilliant students and also very brilliant professionals who choose to go into that direction just because of the nature, the wide scope, and the complexity of the role.

Mo: Any asks for the audience? Are you hiring or is there anything else you would want to ask people to do?

Anna: Yeah, I’m definitely hiring and definitely interested in having brilliant McGill students who are curious and want to give us a call or look up what we have. Sometimes, students just reach out and say, “Hey, is there anything? Here’s my profile.” Definitely, there’s a lot of ex-McGillians here or I guess… Yeah, ex-McGillians. That’s definitely one.

Anna: The other one is if anyone listening has friends or family working in HR or in finance or leading some companies in Canada who have the wellbeing of their employees at heart, speak to them about Dialogue, speak to them about our primary care service and about our mental health service because I think it’s a service that’s really loved by employees.

Mo: Where can people find out more about Dialogue?

Anna: and we’re Dialogue Technologies on LinkedIn, on Facebook. Yeah, on all the social medias.

Mo: Thanks for being on the show.

Anna: Thank you.

Visit Dialogue’s career page at
Mo Akif

Mo Akif

The Editor-in-Chief of the McGill Dobson Chronicles. Never having started a lemonade stand as a child and tired of reading blog posts about entrepreneurship without actually doing anything, he was on the verge of giving up and joining a pyramid scheme. Luckily the McGill Dobson Centre decided to adopt him, allowing him to get a closer look at what it takes to build something valuable.