They say the only certain things in life are death and taxes. If you want success in the FinTech world, that list changes to necessity of liquidity, strong relationships, navigating regulatory burdens, and establishing and maintaining consumer trust.

RateHub and the DMZ at Ryerson partnered up to host Canada 150: The Future of FinTech, and address these four issues.

The panel featured Jordan Wimmer, co-founder of Thrive Savings; Jamie Alexander, co-founder and CTO of Sensibill; Andre Salvi, managing director of BMO Partners; Alyssa Furtado, co-founder and CEO of RateHub; and Karney Li, VP of Engineering at Wealthsimple.

The room was curious as these people – all from very different walks of the “FinTech” life – came together to talk about how the financial services world is changing. There was much agreement on the panel, namely a bigger push for collaboration over ‘disruption’ and an honest conversation about what startups really need in order to entice big banks to partner with them.


“You need capital to survive a long sales cycle,” Alexander said in response to a question on the funding landscape in the FinTech world. “So you leverage as many government programs as possible, but you simply can’t live through two-year sales cycles without additional funding from VCs.”

This comment was in interesting contrast to Furtado, who said that RateHub has taken no major VC funding but used government programs to raise nearly $1M in cash and rebates through programs like IRAP or SR&ED.

There’s interests aligned between FinTechs, big banks, and regulators.

“We wanted to develop relationships with big banks from the start, but it was hard because the sales cycles were too long. We got involved with the [mortgage broker] community because we could call up smaller brokers and get a deal signed that day,” she says.

“Because of the necessity of needing to be profitable, we were forced to focus in on one vertical where we could make money,” Furtado continues. “Once we had profit, we could expand into other verticals like credit cards and savings accounts. Now, we are having conversations with big banks and working with some.”

Throwing another experience into the mix, Wimmer told the audience her story of founding Thrive, which is set to launch in the next few months.

“I was solving a pain for family and friends – no one had a savings plan,” Wimmer said. “Then I interviewed 500 potential users on their financial aspirations, goals, and to see what’s working. Once I had that data, we were able to chat with some of the banks up front to see how we could work together.”

Building relationships

When it comes to partnering with startups, Salvi does not mince words. As the managing director of BMO Partners, it’s his job to lead a cross functional, enterprise-wide team to leverage technology to generate new experiences for customers.

“Keeping data secure, in order to build trust with our customers, is our number one priority,” he said. “With that in mind, we look for best-of-breed partners that have longevity. We look for product, vision, liquidity, bench strength, management philosophy, and transparency in the process to see who we want to work with.”

The startups in the room agreed with this, but pushed back a bit to talk about some of the things they want to see from banks – namely, cross-functional teams and a revised contracting process.


“Where big banks have to adapt is in contracting,” said Alexander. “The big master service agreements (MSAs) that lawyers go through is expected for a large vendor – but it is difficult to take a startup through the same path. There are some areas, like confidentiality, that cannot be compromised. However, there are other areas to change for startups.”

“Teams at banks also have to be more cross-functional,” added Wimmer, talking about how many banks are business-line focused, whereas some FinTech companies require talking to multiple stakeholders at once. “For the bank deal we just closed, our internal champion put together a cross functional team from six business lines, then gave them the autonomy to make strategic decisions so we could work with them.”

Navigating regulatory burdens

If the banks and startups couldn’t quite agree on what was necessary to work with one another – a bank talking about longevity and a startup talking about ease of contracting – they could all agree on one thing: regulations need to be revisited.

Wimmer levelled with the audience, noting that regulations are expensive and confusing. At Thrive, they’ve focused on building an “A+ team of compliance and regulatory experts” to help them navigate, and in time, influence and shift, regulations.

Li agreed with Wimmer, but says Wealthsimple has a different approach to regulatory compliance. Instead of looking to achieve the specific wording of the regulation, they actively work with regulators to identify the intent of the regulation. If they are able to accomplish the intent, then they can show the regulators they are compliant, even if they didn’t follow every letter ‘to a t.’

“If you look into the market, there’s interests aligned between FinTech companies, big banks, and regulators,” says Salvi. “Both FinTech companies and big banks need to be able to test new models of service at a small scale without the regulatory burden, but regulators are figuring it out just the same as we [banks and FinTech firms] are.”

Establishing and maintaining consumer trust

The importance of regulation is to protect customers, but brand value also goes a long way to building consumer trust.

“My mother is afraid to use her credit card at the pay-at-the-pump gas stations,” joked Furtado. “I don’t think she’d be comfortable using a robo-advisor for her banking.”

“We have to take more ownership over our financial future.”

– Alyssa Furtado

The audience resonated with this, but then Alexander shared a story about the UK, a new market for Sensibill. He noted that many people don’t trust FinTech brands alone, Sensibill’s brand included. However, when you put a big bank name on the product or service that people trust, he says that consumers are more willing to use it, showing that it’s less about the technology and more about the trust factor.

This has profound implications for the FinTech world, which might be a reason behind FinTech’s shift from disruption to collaboration. Customer experience might help you win at customer retention and long-term brand building, but even the most innovative FinTech company might be reliant, in the early days, on the consumer trust and scale that comes with a big bank.

The future of FinTech

Far from being too much of a love-fest, the panelists had interesting visions for the future of FinTech in the next five to 10 years.

“We are moving from the internet of things to the ‘internet of me,’” says Wimmer, talking about her view that tech products will become hyper-personalized.

Salvi and Furtado agreed, noting that tech will generate new user capabilities and lead to more educated users, respectively.

“We have to take more ownership over our financial future,” explained Furtado. “As companies respond, this means more transparency and accessibility – making banking exist primarily on our computers.”

Far from becoming an AI-filled, human-less void of technology, however, the FinTech space will always have and need people, says Furtado.

“We have to embrace new technology, but understand its limitations and have an exit strategy. As capabilities increase, we can empower high-knowledge individuals to focus on advice, with technology removing barriers, obstacles, and friction.”

Read the original article on BetaKit and follow me on LinkedIn

Build a more effective diversity strategy

By 2017, the majority of all Fortune 500 companies have a stated focus on diversity and inclusion. In the tech world alone, PinterestSlackApple, and others have released their diversity numbers.

But these numbers aren’t improving year over year for many. In some companies, this issue has led to a laser priority on increasing numbers with a focus on only one identity.

In the business world, these two pieces of advice – prioritize increasing your key metrics and focus on one thing – are pillars of a successful strategy. Otherwise, too much gets in the way and the team does not know where it’s headed.

With diversity, however, this can be a recipe for failure.

Humans are inherently, well, diverse. That’s what brings innovation, new ideas, access to new markets, and better consumer understanding. Trying to increase diversity by focusing on only one identity might offer some vanity metrics, but in the long run does not tackle the underlying issues that caused the lack of diversity in the first place.

A quick disclaimer

When I say “diversity,” I am using the phrase to refer to both inherent and acquired diversity. This definition truly does include all people, and it becomes incumbent on an organization to recognize and promote the “diversity” in every one of their employees.

Why do single-identity diversity strategies fail?

Put simply: no human has only one identity.

Regardless of how good a person we think we are, humans love to feel included and like we are “in the know.” A strategy that is focused solely on one identity means that anyone who does not share that identity will not be included. A couple studies, notably from Harvard Business Review, found this is big problem.

Trying to increase diversity by focusing on only one identity might offer some vanity metrics, but in the long run does not tackle the underlying issues that caused the lack of diversity in the first place.

Does your company have a single-identity diversity strategy? Don’t worry! There’s something you can do

If you find yourself in a company that cares about diversity and inclusion but is focused on only one identity – women, for instance – there are things you can do to help ensure that you’re still making real progress.

1. Allow “scope-creep”

For those of you lucky enough to not know what scope-creep is, it’s when you planned to do only ABC but then ABCDE happens because life took over. Usually, this is a bad thing.

This time, scope-creep can be a tool to make your diversity strategy more powerful without watering down the message.

Taking a look at “women,” you’ll notice there are many different ways a “woman” can exist in the world. She might be lesbian, bi, trans, or straight. She might have a disability or be able-bodied. She might be white, black, Asian, of Indigenous heritage, or any other racial/ethnic background.

If the initial scope is “woman,” the “creep” is the intersecting levels of identity – sexuality, race, ability, etc.

When looking at strategies and initiatives to be inclusive of “women,” ask how the initiatives will be inclusive of all types of women. If a specific initiative either does not help or inadvertently harms another type of woman, then the “women” strategy cannot be accomplished to its fullest potential and might benefit from iteration and editing, which we’ll get into in the next two tips.

When you include other types of women in the strategy, you naturally build initiatives that are helpful for members of other communities even though you don’t have a “focus” on them. For instance, if an initiative is good for a woman with Indigenous heritage, it will likely be at least somewhat good for all people with Indigenous heritage. It offers you a starting point to build on later.

2. Have both “problem” and “solution” interviews

I’ve been lucky to work with over 100 companies on their diversity and inclusion initiatives, and in that time I’ve seen a common thread:

  1. A diversity committee is founded and supported by an executive champion.
  2. That committee, often filled with members from diverse communities, talks amongst themselves and may do surveys or interviews with other employees to see how they feel and what they believe a solution might be to make their organization more diverse and inclusive.
  3. Then, taking all the feedback they gather and their own brainstorming, the committee comes up with a solution, presents it to the executive, gets buy-in, and moves on to talk about roll-out plan.

This sounds great, except for one thing: no one checked with employees if they actually want the solution.

Since the interview/survey process is bound to have some communication challenges, it’s highly possible that the committee could get all the right information but then put the pieces together in a way that does not resonate with those it intends to support.

In these cases, the committee did a good job of “problem interviews,” which are asking people how they feel about a given problem and what they think the solution should be (whether actual interviews, surveys, or another feedback method).

Where they missed the mark, however, is the “solution interview,” which is the process of going back to the original interviewees and showing them your solution, asking for feedback and buy-in before announcing its roll-out.

Closing the feedback loop with solution interviews is crucial because it:

  • Ensures that the solution will have more adoption; if everyone is signing off on the solution, then you can leverage that commitment during roll-out
  • Helps make sure the strategy didn’t accidentally miss something that could harm both adoption and impact

This is also a prime opportunity to include allies in the conversation.

By re-crafting a version of your strategy with neutral language, you are armed with different ways to discuss the initiatives depending on your audience – helping get buy-in from skeptics and ensuring that your allies can help you in the conversation.

Get the problems from their perspective as well, and run the solutions by them. Including them in the conversation helps get increased buy-in organization-wide, reduces resentment around feeling “excluded,” and offers your allies more information on the process so they can support you.

3. Create two “versions” of your strategy – and then use the second

When it comes to diversity strategy, it’s easy to get lost in the passion of it all. That’s not a bad thing; diversity committees are people who deeply care about the challenges that a given community faces (and, much of the time, they are members of that community). A company should applaud this passion and effort.

By allowing “scope-creep” to consider other identities and conducting both problem and solution interviews, you are likely to have a very robust strategy. However, when a strategy is only written for the community it directly aims to include, it can read as exclusionary even when it doesn’t intend to be.

After your strategy, written with a focus for the communit(y/ies) at hand, is created, go back and edit it to make the language as generic as possible without removing the intended effects.

Have maternity leave suggested in your “women” strategy? Make it parental leave.

Have “more women’s bathrooms” included? Recommend single-stall bathrooms in the building, if that’s feasible, or ask for gender neutral bathroom options.

By re-crafting your strategy with neutral language, you are armed with different ways to discuss the initiatives depending on your audience – helping get buy-in from skeptics and ensuring that your allies can help you in the conversation.

Tying it all together

“Scope-creep,” problem/solution interviews, and creating two versions of your strategy all strengthen one another, helping you get a strategy that is more holistic even as your company has an explicit focus on one identity.

It will require some extra effort, self-reflection, and bridge-building, but the result is far more lasting and impactful.

Having an anchor to your diversity strategy can help you prioritize some of your efforts and get the initiatives underway, while a holistic approach keeps everyone in mind. As successes and quick wins start coming in, you can push further into expanding more “anchors” of your diversity strategy or push executives to focus on intersectionality from the top-down.

Either way, you’re able to target underlying barriers and values, creating a stronger, healthier culture where everyone is able to do their best work.

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A place like the MaRS Discovery District in Toronto is no stranger to hosting events that throw the word “innovation” around like it’s a football. That’s not always a bad thing – sometimes you have to repeat something a hundred times before it sinks in – but it can feel less impactful when it seems like everyone is talking, but not doing much else.

The Urban Design Camp, hosted by MaRS in partnership with Uber, IBI Group, the Toronto Transit Commission (TTC), and others, aims to change that narrative.

The two-day camp is focused on bringing service providers, private sector actors, and public sector stakeholders into the room “with a goal to produce testable options to roll out in the near future.”

The kickoff was keynoted by Raquel Urtasun, the head of advanced technologies at Uber and an associate professor at the University of Toronto, and Josh Colle, a Toronto city councillor and chair of the TTC, both addressed the need for connectedness, albeit in different ways.

Where Urtasun focused on technology, Colle focused on process and learning from history. As it turns out, all are crucial to one another.

Canadian talent

“I chose to call Toronto my home, and did not want to move to the States,” recalled Urtasun.

In the not-too-distant past, this would have meant her career in artificial intelligence was all but over.

Toronto is a pioneering city of artificial intelligence in the world, but “the talent kept leaving – often for the USA.”

While the University of Toronto took on its own initiatives to combat brain drain of researchers who studied advanced technologies, Urtasun took a more practical approach, founding the Vector Institute for artificial intelligence. This, she says, gives a new home to AI research in the heart of Toronto, helping to ensure its survival.

More than just survive, however, Uber and Google came knocking on Toronto’s door because of its burgeoning AI scene. Uber has chosen Toronto as a core geographic hub of its artificial experiments, in no small part due to our history as AI founders, but also to our current, increasingly successful, efforts to reclaim the amazing talent we had.


Google is trying to enter Toronto in a big way, through its urban-focused subsidiary Sidewalk Labs, to take over a 12-acre stretch of land on the waterfront to build a connected city.

All of this can be accomplished through Toronto’s growing talent networks. People often say that a company, or city, is only as good as its people. If this is true, then Toronto is on a strong trajectory in both the private and public sector.

Studies about the relative wages and cost of living in Toronto versus Silicon Valley — and the obvious political elephant in the room — have caused more and more intelligent minds to see Canada, and Toronto, as a viable and strong career option.

When this happens, a natural pull effect occurs; smart people want to work with other smart people. So if smart people come to Toronto, you know what comes next – more smart people. For those smart people already in Toronto, their choice to defy current tides and stay here instead of moving to the US is one more pull for the brightest global minds to come, and stay, in Toronto.

All this brings more people together, building our talent ecosystem in ways we can only dream of right now.

Canadian technology

“The TTC was founded almost 100 years ago to bring private bus services, streetcar lines, and other transportation providers under one roof,” explained Colle. “This is what is happening now with 21st century technology in the mobility and transportation industries.”

Far more than just offering choice, consumers want integration, says Colle. They want to merge their commutes with ‘multi-modal transport,’ a fancy way of saying you walk, take the train, take the streetcar, and maybe even take an Uber in the same commute.


Learning from the operational shifts of the past can give a pathway to the technological changes for the future. When the TTC was developed, it brought disparate systems under one organization. While it’s no longer necessary to make all transit options operate under one company, technology can be the “one roof” that provides a seamless user experience in the mobility sector through integrations of payment systems, operations systems, and back-end technologies.

Beyond just making business and pleasure commutes more seamless, however, technology such as artificial intelligence and self-driving cars increases access to mobility for the elderly, people with disabilities, and young people – all vulnerable populations that have limited mobility when compared to their middle-aged, able-bodied, working peers.

When these vulnerable populations are more mobile, it raises the quality of life for everyone, as primary caregivers also have more access to mobility and face a lesser burden of care as their loved ones become more independent.

True to the motto of doing well by doing good, technology has an opportunity to take the consolidating benefits seen from the last century one step further: into building a more inclusive society.

Canada’s time

There’s much debate about whether Canada has hit an inflection point in our growth on the global scale – and if we have, what the right next step is.

Some say that Canada is too small a market, and that we still need the United States. Others suggest that our success is temporary, based on inflated demand from global turmoil and Canada’s relative peace.

While both of these reasons are valid thoughts and there’s evidence to suggest both, the speakers at this event provided a different thought: so what?

IBI Group presented a lightning talk on the move to connected cities, and used New York City as an example of the great work they are doing.

But here’s the kicker: New York City was a test project.

With a city as big as New York City, it’s nearly impossible to create brand new solutions that will immediately scale across the whole town. However, testing a small dynamic in a city that size can offer huge insight into, for instance, an entire city solution for a city the size of Toronto.

Looking at the solutions themselves – connected cities and technology facilitating smooth operations and broader inclusion – it does not matter if the wave that gets us this technology is only temporary.

Once it’s there, we reap the benefits for a long time to come, because the infrastructure being built today is made with the future in mind — a mindset that was present, but ill-informed, during our last major infrastructure development period during the early-mid 20th century.

Of course, if we don’t continue to focus on guiding that scale properly, we will end up right back in the same position we are today, in 50 years. However, even with a temporary wave to get us these changes, a cooling of political climate will not take away the massive global headway we gain by building scalable, integrated infrastructure.

Article photos credit: Alex Foster-Roman

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I’ve had the privilege of hiring a few teams in my professional life, and I can honestly say I am so proud of the work they do.

I typically lead sales and customer success teams, meaning our metrics are clear – money. It makes progress easy to track once the team is already there, but the interview process is really where the smallest error can lead to huge ramifications – and an unsuccessful team.

In my previous experience working as an HR consultant, I frequently heard recruiters talk about the need for culture fit and role fit. It’s an interesting topic that took the recruiting world by storm, but it has its flaws. Especially as companies aimed to diversify their organization – both in terms of explicit diversity (one’s gender, race, sexuality, ability, etc.) and implicit diversity (one’s life experiences, schooling, or geographic background outside of ethnicity), the notion of “culture fit” can be damaging. For more on what “culture fit” interviews can do to your diversity efforts, check out this great piece in Forbes on the subject.

So what’s a recruiter to do? If asking about culture is off the table (and asking about diversity can make candidates and companies alike cringe), how can a company assess whether a candidate is going to fit in with the organization?

In my experience, this line of questioning helps to assess role fit, organizational fit, and increase diversity. Try it out:

Ask how a candidate understands and lives your values, not culture fit

Let’s say your company has a value of creating a supportive team environment. This has been distilled through “culture” – the amalgamation of all employees’ personalities, wants, and social desires – to mean that you have team hangouts after work on Fridays.

In an interview, then, you don’t want to ask questions that will assess whether this candidate will happily join the Friday parties, but instead questions that will ascertain whether this person believes in a supportive team environment or if they prefer an environment of everybody-for-themselves.

When candidates are able to be more human in the interview, you can more easily assess whether they will be a good fit

This is not to say that you have to be best friends and super supportive of one another all the time to build a successful company – a lone-wolf approach to performance can draw out immense creativity – but if you want to get employees that live your values, you should ask about the values themselves, not the culture derived from them.

Try questions like these (and feel free to adjust for your company):

  • One of our values here is to build a supportive team environment. How do you understand that statement and what does it mean for you?
  • We have a corporate value here of transparency and brutal honesty. Can you tell me about a time you received critical, but necessary, feedback, and how you acted upon it? What about a time you had to deliver that critical, but necessary, feedback?
  • Our core value is clients come first. While we have decent working hours usually, sometimes we get late calls from panicked clients. Have you ever had to pass up a personal night out to serve an emergency client need? Tell me about it.

A candidate’s answer to these questions will signify a lot about how they see the world. First, you’ll get a gut reaction to the value itself, and second, you’ll get their beliefs on how that value should be lived. It doesn’t mean they should be crossed off the list if they don’t think Friday parties are a way to build supportive environments, though; these answers are just a way to get a more clear picture of the candidate in relation to all their other qualifications.

Ask questions that will determine if a candidate’s “managed” style fits with their would-be manager’s “management” style

Assuming for a second that your managers all have a management style congruous with your values (and, like culture has many iterations, there are multiple ways to “manage” someone that aligns with company values), figuring out if someone likes to be managed in the way your managers like to manage is crucial to bringing out the best in everyone.

If a manager’s style is laid back with only occasional touch points, then you’ll want to make sure your candidate is self motivated, ready to act, and able to make decisions with little oversight. Other companies are more hover-based management (valid when dealing with sensitive information, for instance). Regardless, you’ll want to make sure you’re bringing on people who thrive under whatever approach you use.

Try these questions:

  • What kind of management style do you work best under?
  • Do you prefer a manager who tells you precisely what to do for core steps (not every step along the way, of course) or a manager who tells you the end goal and then leaves you alone?
  • If you had an emergency client request that had to be dealt with but your manager was not available to help or give you feedback, what kind of steps would you take to solve the problem?

Speaking to scenarios that might happen in your organization and getting a better understanding of what the candidate feels is a good management style for them will be helpful in assessing whether a candidate is going to do their best work in your organization.

This is also where thought diversity can really make itself known. When a candidate tells you about how they work best – preferably with examples to match – they are painting a full picture of their background and their previous experiences. There’s no right or wrong way to answer these questions, either, so you can offer an up-front disclosure that you are just trying to get to know them, which helps bring their authentic selves into the room.

Clarify your understanding of candidate answers using direct needs from the job

Let’s say you’re in a conversation, and after you describe a bit about the role, the candidate responds that they are excited for the role. That they are hard working and will happily bring that work ethic to your organization if given the chance.

You’re excited – it’s great to feel heard by this candidate and get a positive response. But not so fast. Any good candidate can memorize a script of “I’m excited and hard working.”

Push a bit further. Try these questions:

  • I love that you said you’re a hard worker. We need that here. Just to clarify my understanding, when you say you’re a hard worker I hear that you are willing to do (insert difficult aspect of the job here). Does that sound right to you or did I misunderstand?
  • When you said you were excited for the role, can you explain a bit more about which part excited you the most? Do you have any reservations about taking this role?
  • I like the experience you shared with me about needing to complete (a similar task to what this job requires) – how would you have improved your outcome from that task, knowing what you know now?

When a candidate tells you about how they work best – preferably with examples to match – they are painting a full picture of their background and their previous experiences

How they respond to these questions will really help you understand if they are a good fit for you, for your needs, and for right now. You may need someone to stay late for the role on a regular basis – it doesn’t matter how brilliant someone is if they demand their evenings free 100% of the time. If that’s the case, they just won’t fit in your organization.

Bringing in diversity of thought comes in naturally at this stage, as different roles will require different beliefs and views on what a generic term like “hard working” really means. For sales, hard working might mean pounding the phones even when you’re tired. For customer success, it might mean being willing to travel across town to say hi to a client. For product, it might mean asking for 10 more customer interviews and then completing them… even ahead of huge time crunch.

It’s all about finding who is right:

  • For the role
  • For the team they’d be joining
  • For the company as a whole

It’s the recruiter’s job to figure all this out (with help from the teams themselves, of course). Asking these questions will help bring the candidate into the process, making the interview more of a conversation than a question-and-answer session.

When candidates are able to be more human in the interview, you can more easily assess whether they will be a good fit or whether they belong elsewhere in your organization/not in your organization at all.

Check out the original article and follow me on LinkedIn

Don’t ask about diversity – ask these questions instead

If you identify with a minority community or consider yourself an ally, you probably know this story.

You recruit with a company that raves about how much it cares about diversity and inclusion. When you start the job you get a distinct feeling that, while the company might mean well, they aren’t as inclusive as they bill themselves to be.

During your next job search, you promise yourself, you’re going to identify whether a company is inclusive before you join, not hoping it is after the fact.

The issue is that as diversity and inclusion increases in profile, it becomes at once a huge corporate priority and a business line with (occasionally) not much behind it.

Inquiring minds who want to learn about a company’s approach to diversity and inclusion might not feel comfortable asking the question directly – or that asking directly won’t reveal the true answer. Perhaps you’re joining a young startup or small business that maybe hasn’t had the time to think about diversity and inclusion. It doesn’t mean they aren’t great places to work, but it does stop you from getting that answer by directly asking about diversity and inclusion.

Try these five questions instead:

What is the feedback culture of the company like?

By asking this question, you are hopefully uncovering how the organization, and its employees, respond when challenged, called out, or given constructive advice.

Diversity and inclusion, bluntly, can be messy and personal. An offensive comment or derogatory remark is not fixed by a “business strategy,” but by individuals standing up for themselves, allies supporting them, and management reinforcing the learning. All of this is predicated on people and their ability to take feedback.

If I can’t offer innocuous feedback to my colleague about how to approach a client or suggest they use a cool code workaround I discovered, I highly doubt I could approach them about changing potentially life-long held beliefs that are, however unintentional, discriminatory in nature.

Bonus points: asking this question will show that you are open to learning, a big plus for organizations.

How transparent would you say the company is when it comes to internal workings, strategic decisions, and corporate vision?

This question speaks directly to top-down communication, a crucial factor for creating an inclusive environment, but asks it from the perspective of the individual.

If the interviewer hymns-and-haws, offering a half-baked answer about how the company has a strong vision and everyone really supports it, you might have a problem on your hands where creating inclusive environments is concerned. Without clear and transparent communication funnels from the top down, employees get the message mixed. Good people are then not armed with the corporate messages they need to create a healthy culture on their team, and other folks who don’t care are not reminded of the vision and culture they chose to support by joining the company.

If the CEO can barely tell me why we are in business and where the company is going, there could be an even bigger challenge trying to get the CEO to talk about very personal, high EQ subjects like diversity and inclusion. If I can’t ask my manager a question about my work and get a clear answer or an honest “I don’t know, let’s figure it out together,” I’m even more concerned.

Note: You’ll want to cross reference this answer across a few folks at different levels – the SVP might feel the organization is super transparent while the new junior dev might say otherwise.

An offensive comment or derogatory remark is not fixed by a “business strategy,” but by individuals standing up for themselves, allies supporting them, and management reinforcing the learning.

If I have an issue – from needing a new mouse to wanting to talk over my benefits – how would I do that?

You may want to save this for a later stage (perhaps even after you get the offer), but it speaks to the processes in place for a company when things go wrong.

Every organization can be fantastic when business is good and compliments fly; it’s the bad times when biases seep through and facades fade away. If you ask about these simple accommodation processes and there are none in place or it is very ad-hoc, it could be a red flag because it signals the organization may not have thought about nuances and personal issues – the ones that need to be talked about when someone is concerned they are facing discrimination at work.

By offering a more innocuous example and a range of issues that are not connected (a new mouse would usually be IT, benefits would be HR), you get a better understanding of whether the process is ad-hoc or well defined. Sometimes you also figure out whether the individual knows the process at all, a good indication of the communications process at the organization.

What do you love about your job and what do you hate about the company?

Asking such a blunt question may not be your style, but bear with me for a moment. When you ask this, you learn more about the person you are talking to – sometimes even more than you’d learn by being friends with them.

What people choose to highlight as things they love or hate can tell a lot about the individual and how the organization trains your thinking. Also pay attention to body language – their lips might be saying they love how nice everyone is but their body language might be indicating that they are uncomfortable or seeking an innocuous answer to avoid the question.

This might just be their demeanour if they are not used to being asked this question, but it could suggest that honesty is either not fully allowed, not valued, or the real answer might scare you away – a big problem when you’re assessing whether you’ll be welcomed in that culture.


What do you think is the greatest risk that the company is facing in the next 3-5 years?

Asking this question actually has two additional benefits beyond a proxy for diversity and inclusion: it shows them that you know how to think mid-long term and it shows them that you are concerned about the organization as a whole, not just your pay and benefits. Both are great for an organization because they need folks who can see the big picture at all levels of the organization.

On the diversity and inclusion front, asking about risks prompts a sense of personal awareness in the interviewer that will be crucial to you understanding their honesty in the other questions you asked. It shows that the individual you’re speaking to (or all of them throughout the process) are able to see some of the big picture as well.

When your colleagues are able to think long term with a big picture mentality, you will avoid the issue that, should you join and bring up an issue that arises, your concern is belittled. A big picture thinker will understand the broader ramifications of a seemingly simple incident, but they will also be able to help calm additional anxieties you might be feeling since they will likely have other experiences to draw on. 


These five questions are not a magic bullet by any means, but they will help dig into the corporate culture a bit more, helping you make an honest assessment for yourself whether you’ll be able to do your best work at the company in question.

If you’re involved in making your organization more inclusive, ask yourself these questions and see what your answers are – it could help you identify challenges in your own culture.

Do you have other questions that you think a great proxy for assessing whether a working environment is inclusive?

Follow Stefan on Twitter @stefanpalios


Never before in a panel have I seen so many dichotomies pop up.

BrainStation hosted a panel in Toronto on FinTech featuring some very bright minds, including EQ Bank’s Dan Dickinson, President’s Choice Financial’s Phil Gene, BMO’s Peter Poon, and Scotiabank’s Kevin Stewart, and the stories were great but also filled with warnings, additional thoughts, and add-ons.

On one hand, banks are walled off oligopolies; on the other, they are massive data centres with troves of information that the public can benefit from. The panel touched on helping the customer succeed, but there were big concerns around the negative effects of automation on lower-level banking jobs. The banking system is notorious for its cushy-with-the-competition mentality, but at the same time there are genuine efforts being made to partner with new FinTech companies.

Within the conversation, some nuggets emerged that helped tell the story of FinTech, its goals, and some of the subtleties to watch for as you navigate the financial world of the future.

The history and tensions of FinTech

Dickinson kicked off the panel with his understanding of the origins of modern FinTech, noting that it goes back to the release of the iPhone in 2007, and the financial crisis of 2008. The iPhone solidified the mobile world, meaning that there was “huge demand for life to happen in your pocket,” he says.

This kick-started the world of app development and mobile-first development, but the financial crisis a year later created a new opportunity for would-be newcomers to the financial services industry.

Not only was the technology reaching a stage where it could be commercialized at scale, for the first time in modern history, banks had fundamentally shattered both trust with their consumers and the image of stability, two core pillars of their success since the beginning of financial services.

fintech panel

The tension between technology and financial services began almost immediately. Open source technology, made famous by Google Android and others, became the defining feature of the tech industry. The banking world, by contrast, was seen as a “walled garden” where only certain people were allowed in.

The openness factor played well for FinTech startups who could, now that consumer trust in big banks had been hurt, swoop in and acquire customer loyalty through more efficient customer experiences and user-centric service and support. Banks took note of this, but struggled to create brand new services while still ensuring that their current businesses don’t fail in the process.

This is where “open banking,” as described by Poon, comes into play.

Open banking is the idea that a bank, or any financial institution, cannot afford to lose consumer trust again the way they did in 2008. So instead of rampantly experimenting with consumer dollars, FIs can innovate on their customer experience to match those of nimble startups. With a focus on customer experience, big FIs start to play in the same mindset as FinTech startups and can achieve similar successes.

Asking the right questions for innovation

Another challenge for big FIs interacting with innovation, technology, and the startup ecosystem, is the question of whether to ‘buy or build.’

Dickinson and Gene, however, think that’s the wrong question to be asking.

A valid concern coming out of the FinTech world is emerging technologies and their effect on employment.

What big FIs should really be thinking of is, “what core competencies can we not afford to outsource?” says Gene. Once you’ve answered this, the options actually extend far beyond ‘buy versus build’ into buying, building, buying-then-customizing, investing, partnering, and incubating.

EQ Bank, for instance, is a small bank with limited budget, meaning that both “buy” and purely “build” are not really on the table, says Dickinson. However, what EQ does instead is build infrastructure that enables integrations with FinTech companies. Then they invest in companies building the technologies their customers need.

“We focus on an ‘execute what the customer wants’ mentality,” says Dickinson. “which means that investments and partnerships are good strategies for us.”

BMO feels the same way, says Gene, explaining that BMO has three FinTech incubators, including one in Toronto.

“Using our incubators, we can invest or incubate and provide mentorship, but partnership is always on the table if it makes our customer experience better,” said Gene.

The people behind it all

A valid concern coming out of the FinTech world is emerging technologies and their effect on employment. While the panel was happy to talk about automation and AI’s ability to “bring the bank to you, where you are,” says Stewart, the fear still remains that full automation could cost tens of thousands of jobs – not only at the banks themselves, but also in ancillary services like real estate, as branch networks shrink or close down entirely.

Granted, one cannot look to financial services to solve the challenges of every industry, but banks in Canada have a large part to play as the five major banks control the vast majority of assets and deposits in the country.

Coon and Stewart, the “big bank” folks on the panel, agreed that the concern is massive.

“We don’t want to tout the power of technology on the same day the news is running a story that we laid off thousands of branch workers,” said Stewart.

What they are doing instead is training people. Stewart says that Scotiabank offers retraining for their branch staff on technologies. Coon explained that BMO has a “we need people” policy towards its operations, meaning that the bank will first look to move their people to other areas and offer training or support before it looks to letting people go.

Continuing to the future of FinTech, the panel had one word: magic.

Payments would be done biometrically for a frictionless payment experience. Branches would no longer exist. Through AI and mobile banking, though, a “branch” could be ‘wherever you are, however you need.’ Customers can always talk to someone, using digital and video to connect with the right person for the question, which is sorted and assigned through machine learning.

It sounded utopian, but the technology is not far from existence if it’s not here already. The question remains, though: will this technology be used to make banking more human, or less?

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It’s always funny to me when founders of companies “get real” with you during panels. These are smart people, to be sure, sharing how they overcame multiple challenges, their insights on the world, and their company journey. Many, however, can fall into the trap of universalization – the idea that because it was their path, it must be “the” path.

Thankfully, the latest event in Venture for Canada’s Scale Up series, hosted with BDC Capital, didn’t have that issue.

Moderated by Ben Bergen of the Canadian Council of Innovators, the panel was at once unassuming yet forceful in the impassioned beliefs of the three founders on the panel. None, however, claimed their way was the right way – merely the path they took based on their own circumstances and beliefs.

The panel, featuring Bianca Lopes, founder of BioConnect; Steven Uster, CEO of FundThrough; and Heather Payne, founder of Ladies Learning Code and HackerYou, was focused on scaling up. The founders touched on the more human and business process elements, giving the audience a thought-provoking discussion with practical ideas.

Scaling yourself

“Being a founder can be lonely at times,” lamented Uster. “You can’t share every decision you have to make with your team…you can’t share the anxieties of it all.”

Far from complaining without a solution, however, he suggested all entrepreneurs find three types of non-overlapping mentors. Business mentors for overall process and founder-related questions, industry-specific mentors to ‘talk shop,’ and personal mentors to act as your “confidential personal board of advisors.” The combination of the three will allow you to grow, to learn, and to vent; a powerful mix when you are building a company.

Payne agreed with the idea of needing mentors, but shied away from the idea that a mentor must be hyper-successful and more experienced. Payne said she has a hard time relating to the advice of some mentors who are “light years ahead” of where she is right now in her business.

bdc scaling panel

While she does maintain many relationships with wildly successful entrepreneurs, counting Hubba founder Ben Zifkin among them, Payne finds the advice of folks who are “six months to a year” ahead of her helpful because they will have just gone through similar challenges, and the solution is fresh in their minds.

When it came to the crutch of personal growth, Lopes says it’s based in self-awareness. “I knew we were a scale-up when I didn’t have to do everything,” she recalls. “But knowing where to act versus when to step back came from a realization of my limitations. It can be scary [to identify your own shortcomings], but it’s necessary for business growth.” Payne chimed in on this point, noting that the most painful aspect of growing HackerYou was declining other creative endeavors as she focused on what HackerYou needed.

“You have to be okay with letting interesting things fall to the side as you focus on your business.”

Scaling a business

Moving away from the founder mindset of hustle and disrupt, a scale-up requires a focus on process and protocol. It’s necessary to “play way above your weight,” says Lopes.

“We had a situation with a potentially huge client who was asking for very specific and detailed information. I had it all in my head, but we had to protocol and document it all in order to inspire confidence in that client.”

This type of challenge is why it remains crucial for anyone in a growing company to recognize that they cannot – and should not – be making every possible decision. This is painful, says Lopes, when you are concerned that a staff member might have a limitation in a certain area but you cannot step in every time to fix the problem. Instead, as a leader, it becomes your job to continually be aware of your strengths and limitations, stepping in, and stepping back accordingly. You also have to keep an eye for the strengths and limitations of your staff, moving them around as needed or as they suggest themselves in order to best achieve your required outcomes.

Similar to a mindset of process and protocol, Payne noted that-scale ups cannot be penny-pinchers, but instead realize that spending is necessary for growth. She used to question every dollar that went out in the early days of HackerYou, but now she now is far more relaxed with necessary business spending in categories rather than approving specific individual expenses line by line.

Further, she doesn’t even touch all the business decisions anymore. Payne said that another part of growing isn’t just letting the reins a bit more loose on the money, it’s trusting someone else to spend parts of that money without you even knowing – and that’s okay.

Scaling the ecosystem

“You can be successful in any geography,” said Uster. “But in order to make a real impact you have to look beyond Canada.”

This statement, however, does not mean that starting and scaling in Canada is not a good idea.

Our costs of living are lower and our population is comparatively more educated on average than the United States. Given changes in the US, UK, and Europe, our immigration system could be taking in the brightest talent in the world.

But a few things are missing.

We need a mentality of buying Canadian, says Lopes. Buying Canadian does not mean shunning the rest of the world, nor does it mean Canadian companies can’t go international, but it’s nearly impossible for Canadian companies to grow into global powerhouses without support from Canadian customers.

“Founders must be vulnerable, able to ask for help, and be willing to give up on other things in order to focus on the growth of their business.”

From a regulatory perspective, Uster suggests a “passport” system and standardized regulations in industries like financial services or education. That way, a company can become properly regulated in one region, using their “passport” to help them expedite the process in other regions where they want to do business. As regulatory burdens can cost hundreds of thousands of dollars to set up in each region, a standardization process will automatically make the process far more competitive for startups and more attractive for investors.

When it comes to talent, the conversation abounds with talk of bringing in skilled immigrants – and the government is responding. However, this is only one pillar of three that are necessary to build an ecosystem, say Payne and Lopes.

You have to bring in skilled immigrants, surely, but you also have to train and grow the talent already here, and focus on retention. This ensures that our current bout of international luck doesn’t dry up the moment another country becomes more immigrant-friendly, stealing both immigrants to Canada and Canadians themselves.

Scaling founders

When it comes to founders of companies, “they believe they can do anything,” says Lopes. “That belief helps us put up with the crap so we can come out the other side alive. But we are not infallible.”

Founders must be vulnerable, able to ask for help, and be willing to give up on other things in order to focus on the growth of their business.

When it works, it’s brilliant. When it fails, it’s a great learning experience. Without self-awareness and acknowledging your own limitations, however, the rest of it doesn’t matter.

Photo via Twitter

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