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Typical Modern Meeting - Face-to-face or virtual?

“Expectation is the mother of all frustration.” – Antonio Banderas

Meeting requests are an amazing invention. Pioneered, and standardized, almost 20 years ago by companies like Microsoft (as part of Outlook/Exchange), Novell (Groupwise) and Lotus (now part of IBM Lotus Notes) this innovation had great promise to automate an essential, yet completely routine, aspect of modern life.

The ascendency of meeting request usage, also rides several trends:

  • In the 1990s, I had an Executive Assistant who scheduled my time, acted as a “gatekeeper” and also worked on many projects. She was a master tactician who managed to keep 3 or more Type A executives productively multi-tasking. In many ways, sadly, such personal assistance is being subsumed by..
  • Increasing computational power means that automation of routine tasks, personalized to the needs of individuals is much more of a reality,
  • The mobile revolution has made meetings much more multi-modal and virtual, but also means that most executives must be productive even while being mobile nomads, and
  • Calendars have migrated from paper – I switched about 20 years ago – to desktop computers using Outlook and the like, and now to the ubiquitous smartphone and tablet devices. Such mobile devices are both convenient for calendars, but also frustratingly fiddly places to enter complex meeting details.

Thus, enter the humble Meeting Request which has swelled in popularity. I received my first such request from an Outlook/Exchange user around 2000 and they remained rare until perhaps the last 5-10 years. Now they seem to be everywhere.

In homage to my friend and colleague, Jim Estill, the quintessential time management guru, I ought to be cheering this time saving invention.

And, yet my enthusiasm is sorely tinged by a frustrating implementation resulting in suboptimal user experience …

Top 10 Meeting Request FAILs:

  1. Trojan Horse: It has always seemed odd to me that a thiFrustrating Meeting Requestrd party inviting me to a meeting could embed their own meeting information in my calendar, and yet I am unable to edit this “foreign” request that has invaded my calendar.
  2. Split Personality: If Jennifer invites me, Randall,  to a meeting, then why does my meeting title say “Meeting with Randall” instead of “Meeting with Jennifer”? Computers are designed to automate routine tasks so there is absolutely no excuse for this one.
  3. No Annotation: I write comments in the notes fields of my calendar all the time. Why can’t I say, for example, “Joe is a bit dodgy” or “First met back in 2001″?
  4. Duplication: Many times I receive a meeting request for a meeting that I have already carefully crafted an entry in my own calendar. Again, computers are supposed to be smart enough to figure these things out and merge them in an intelligent way.
  5. Bad Versioning: Many times when meeting information is changed, such as time or venue, the update isn’t seamless. For example, it is common to have both the original and the updated version lingering in my calendar.
  6. No Scheduling: Meeting requests are often used as trial balloons in trying to schedule busy people into meetings. The endless rounds of “Accept”, “Maybe” or “Decline” responses can end up being quite frustrating, especially for many person meetings. These, often fruitless, interchanges underscore the fact that meeting requests don’t automate routine scheduling. Instead, people have to resort to tools like Doodle to vote on alternatives, and then manually schedule the winning result.
  7. Verbosity by having superfluous words in the limited real estate of the meeting subject line. E.g. pre-pending “Invitation:” or “Updated Invitation:” onto the front of a subject, effectively burying the important words. Many times they are put there to increase the impact and readability of the email subject line to ensure opening, but distract in the actual Calendar entry.
  8. Invitations from Google Enterprise Apps or GMail tend to be the most arcane and ugly. Originally, I chalked this up to Google Calendar‘s relative immaturity compared to Outlook, but the brutally long notes and long subject lines continue to stand out as worst in class, almost to the point that I dread getting invited by Google users.
  9. Lack of Anticipatory Computing: in an age where mobile devices know location, existing meetings and other personal habits, the trend to predictive intelligence could be incorporated into smarter meeting requests. For example, combining meeting requests with shared “Free/Busy” data could remove many manual scheduling steps.
  10. No Personalization: Like my contact list, I put a fair bit of thought into crafting a calendar that is both useful now, but also provides a detailed audit trail of my business interactions. To do this, I use conventions, categories and other techniques that, sadly, cannot be injected into these un-editable meeting requests that instead reflect the third party initiator’s preferences.

Do let me know in comments if I missed any major points.

Given the power of networked computing to automate, why is there such a lack of excellence and progress in this particular area?

In fairness, I believe that part of the problem lies in the interplay between competition and the vagaries of formal industry standards. That said, this should be no excuse.

It is admirable that, unlike word processing formats, the various pioneers started to develop standards call iCalendar (and later vCalendar) around 1997 to standardize file formats (like .ical and .ics) and email server interactions. I do know the Microsoft attempted to extend the functionality with some very useful things around that time. But, for some reason, a great idea got off to a good start, but seems frozen at an almost Beta level of functionality.

To conclude, please read this post, not as a gripe, but instead as a call to action to developers to help take the humble meeting request to the next level of user experience. Any takers?


A mere 25 years ago, the Fall of the Berlin Wall rent the “Iron Curtain” asunder, a re-ordering of western civilization possibly unparallelled since the fall of the Roman Empire.

25 years and 15 days ago, almost by happenstance, I drove the Berlin Corridor, travelled via Freidrichstraße Station behind the Berlin Wall and witnessed an exhausted and bankrupt regime about to collapse.

Today the world has joined Berlin in celebrating this momentous anniversary. This photo shows balloons lighting the old route of the Berlin Wall.

Schmitsdorf FOTW25 Balloons 2014

Photo by Sebastian Schmidtdorf

In 2014, we should be celebrating a distant historical memory. However, the sabre rattling by Vladimir Putin who illegally annexed Crimea, has (not so) covert troops actively de-stabilizing eastern Ukraine and causing existential jitters in the other former East Block countries, leads many commentators to be concerned that the Cold War didn’t end in 1989.

In 2009, for the 20th anniversary of these events, I published the following to describe my own experiences in the surreal world that 1989 Berlin represented:

       Die Berliner Mauer – 20 Years After the End of History


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Angel of the Year Award: Yuri Navarro, Jérôme Nycz, Randall Howard, Michelle Scarborough

At the NACO Summit in Québec City, it was truly humbling to receive the Canadian Angel of the Year Award. I see this partly as a calling to be an ambassador to continue to help raise the Angel bar in Canada in the coming years. I wish to thank all those kind colleagues who, unbeknownst to me, wrote letters of nomination. Also, this is all based on the remarkable people at GTAN and in the Waterloo and Canadian ecosystem generally.

In response to the award, and recognizing the opportunity to build on current success, I shared the following observations and future challenges at the closing Keynote on Friday 3 October, 2014.


Closing Keynote NACO Summit, Québec City Friday 2 October, 2014

Bonjours, mesdames et messieurs. Good morning, ladies and Gentlemen.

I hope that Yuri was aware of what he was unleashing by inviting me to share perspectives and future challenges of Angel investing in Canada! Not unlike a startup running on “fumes”, Canada’s angel sector reminds me of the quip from cartoonist Bill Hoest: “I just need enough money to tide me over until I need more”. I’ll start by looking back to help us paint a future directional context.

As Angel investors, we’ve watched a powerful people-driven engine, coming from nowhere, to become a key enabler of Canada’s future prosperity. As Angels, we fuel innovation companies with our capital and mentorship, ultimately creating some of the highest value jobs for 21st century Canada. What’s not to like about that?

Let’s turn the clock back about 5 years. In 2009, the global economy endured the infamous credit crunch, perhaps the worst economic correction since the Great Depression. I observed this to be the final nail in the coffin for a large number of Canadian venture capital firms, for years struggling to generate viable returns. The seeming extinction of venture capital A-rounds and the bleak landscape for young, emerging companies, compelled me, as a seasoned tech investor, to get involved with the founders at Golden Triangle AngelNet (GTAN) in Waterloo-Guelph-Wellington-Stratford area. In a pattern surely repeated across Canada, Angel Groups from a slow start quietly and persistently worked to fill the funding gap through a labour-intensive “syndication” of Angel capital, with other groups and with government co-investment. In Ontario, this meant repurposing MaRS IAF from its origins as a VC on-ramp to co-investment in Angel rounds, lobbying that ultimately led to the Feddev “Investing in Business Innovation” (IBI) program, and BDC convertible notes.

A typical syndication for a top tier investee company might entail half a million dollars of Angel money being spun into $1.5 million or more. I used to describe this approach as providing “half the money of a VC A round for 10 times the effort”. At the time, I imagined this to be a strategy for a short term “bridge” of Canada’s innovation ecosystem to a more sustainable future. How did this market correction turn out for Canadian Angels?

NACO stats show a remarkable growth in total Angel investment. Between 2012 and 2013 alone, Canadian Angel group direct investments grew a stellar 120% from $40 million to $89 million. Of course, this doesn’t capture the aforementioned co-investment leverage that Angel investors attract nor does it cover investments outside of NACO members. All of us rightfully deserve to be proud of such collective impact.

But is it enough? Both from my own international investing and available statistics, it would appear that Canada’s Angel ecosystem is ahead of Europe on the maturity curve. I would estimate Canada has a 3-5 year head start on Europe. On the other hand, our American friends are definitely well ahead in maturity, deal dollars and information gathering. Angel Capital Association (ACA) data shows almost $25 billion of total US angel investment in 2013. To be at this level, on a per capita GDP basis, Canada would need about $2.8 billion of annual Angel investment. Even counting all the leverage, Canadian angel investment needs to grow 5 to 10 times over the coming years just to achieve parity with the US.

In Waterloo, home of Perimeter Institute, we tend to love Quantum Mechanics metaphors. Thus, propelling today’s critical mass through a quantum leap is a mission all of us need to work on collectively and individually, whether as angels, angel groups, NACO, governments, venture capitalists, sponsors, in fact, each and every ecosystem participant.

So, I will conclude by identifying just five of the gaps that we collectively need to fill:

  1. Scaling: Recently, my friend Steve Currie, VP Strategy at Communitech, observed “Canada is great at starting companies, but not so good at growing them beyond the 5 year horizon.” This means less job creation but also smaller exits. In a study of 183 recent high tech exits versus 2300 comparable US exits, the average US valuation was US$384 million versus US$100 million for the Canadian companies. I don’t know about you, but I find it simply tragic to leave so much value on the table. Angels have a huge role both in mentoring management skills around scaling, but also pivotal to financing that scaling. And, bigger exits, will in a virtuous circle, drive more Angel investment.
  2. Giving Back: We need more of our successful serial entrepreneurs to become (super) angels and continue to start new ventures. In the Silicon Valley, Paypal alone had 14 serial entrepreneurs like Peter Thiel and Max Levchin whose experience and wealth helped build legends like LinkedIn, YouTube, Tesla, Kiva and Yelp. While we do have a few super angels, we have yet to spawn someone like Ron Conway whose 600 investments include Google, Facebook and Twitter. Canada needs more titans like Mike Volker and Jim Estill.
  3. Deal Discipline: Great companies grow and scale partly because of external motivations. In the 1990’s the hottest companies all wanted to do an IPO and that involved a playbook of enhanced management, systems and processes that also helped the companies scale into better organizations. VCs also played a part, but today, this role often falls onto Angel investors, hence requiring a more “institutional” approach versus becoming just another retail asset class.
  4. Co-investment: Government funding has been critical to our success and it is key that funding increasingly backs Angel choices rather than governments having to choose winners. That said, there is plenty of room for more. For example, our Feddev IBI program in Ontario provides a 50% match while the almost identical “Double Equity” program in Austria does a 100% match to angels. And, the Angel Tax Credit, so common internationally, in parts of the US and in BC, would provide a much-needed boost to overall Angel resources.
  5. Operational Innovation: Currently, most angel groups run as nonprofits using largely committed volunteer deal structuring and with little automation of the process. A big reason for this is Securities Regulations, especially in Ontario, that put a chill on innovations that might trigger an expensive regulatory burden. While there is some hope that the proposed Equity Crowd Funding rules might provide the clarity for such innovations, there is also the risk that this is a force that further pushes deals into a retail mode when what we need instead is more institutional discipline.

With these key points in mind, and assuming the right environment, I have no doubt that greater innovation in business models will fuel growth of a larger and more sustainable Canadian angel landscape. All of us can play our part. To dial up our game, will be an aggressive, yet I believe achievable challenge. And, we need even better measurement so we can regularly monitor, and report back to ecosystem participants, our progress.

The road forward isn’t just about traditional business. Because Angel investors’ motivations uniquely straddle the ever-blurring boundary between “passion capital” and Wall Street-style finance, Angel investing will increasingly be a great exemplar of Social Innovation. To me, the culture of collegiality and sharing resembles my experiences in nation-building around charitable foundations.

The last five years have witnessed an unprecedented expansion of Canadian Angel investing and we are poised for even more remarkable growth in the next five. In the words of the incomparable Alan Turing,

“We can only see a short distance ahead, but we can see plenty there that needs to be done”.

Now, let’s get to work …

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Last year, I signed up for a wonderfully ambitious initiative spearheaded by our Governor General, His Excellency David Johnston. I was invited to join a Group of Seven who will serve as catalysts to rolling out David Johnson’s vision of a Smart and Caring Nation built by a set of Smart and Caring Communities, ultimately aimed to be a major national initiative to commemorate Canada’s 150th birthday, or sesquicentennial, in 2017.

I was very much honoured to be asked and, although it is a dauntingly large not to mention a somewhat unspecified, goal, as a proud Canadian who knows first hand David Johnston’s unique ability to lead and motivate, I quickly agreed to this call. I’ll share more about this initiative in order to seek your input. Since no small group can be representative of our huge and diverse nation, it is important the we engage in much dialogue from Canadians of all ages and demographic profile, in order to achieve maximum impact and relevance.

As a way to start that conversation, I’d like to share some of my perspectives on Smart and Caring 2017.

David Johnston’s Smart and Caring Vision:

This whole project starts with a great foundation in our Governor General’s Smart and Caring vision for Canada. And here is why his singular leadership is so critical to this initiative.

David Johnston has a long track record of motivation. Back in 2006, as President of Unviersity of Waterloo, he challenged the already ambitious and successful business, community and government leaders in Waterloo Region to reach even higher. Issued in November 2006, his Ten Goals to Make Waterloo Region Canada’s Knowledge Capital are a blueprint that inspired and motivated real change and continue to have an impact today.

Similarly, on 1 October 2010 at his installation speech as Governor General in the Senate Chambers in Ottawa, David Johnston laid out his vision for nation building in Canada, challenging us to build  a Smart and Caring Nation:

“We are a Smart and Caring Nation.
A nation where all Canadians can grow their talents to the maximum.
A nation where all Canadians can succeed and contribute.
But there is much work to be done to fully achieve our vision of a Smart and Caring Nation. I believe it is essentialTo support families and children,
To reinforce learning and innovation, and
To encourage philanthropy and volunteerism.” 

To build on that vision as we near the sesquicentennial of Canada as a country in 2017, His Excellency has challenged Community Foundations of Canada and the growing network of 191 grass roots Community Foundations across our country. He wants them to lead a groundswell movement, in each and every community and nationally, for Smart and Caring 2017.

Canada – A History of Evolutionary Nation Building:

With that vision as inspiration, and as a passionately proud Canadian, here is my perspective on Canada as a nation. We were not formed by revolution, as is the case in many other countries like the USA or France. True to our character, our particular style of nation-hood opted instead for  evolution at a slow almost glacial pace. You might almost say that Canada pioneered nation building by committee. Specifically, a series of  meetings commencing with the Charlottetown Conference, 150 years ago in 1864, led  to Confederation on 1 July 1867.

I would argue that, as a nation, we were more defined by what we were not — ie. no tea parties or revolutions to overthrow a king. Instead, via peaceful change we enjoyed a tabula rasa upon which to architect a unique nation in those lands north of the growing United States of America. The process was slow. We remained essentially a colony with large parts of the country feeling more British than Canadian for many years. Consider how long it took us to have a non-British Governor General (Vincent Massey, 1952), our own flag (1965, replacing the Union Jack) or our own constitution (repatriated from Westminster in 1982).

Until the late 20th century, innumerable British colonial vestiges remained. Many people argue that Canadian heroism and sacrifices for the motherland in World War I, just 100 years ago, started the modern trend of a strengthening Canadian identity both internally and as a nation on the global stage.

Gof7 WAG 2013-06-06 19.57.00Shortly after WWI, an influential group of painters, the original Group of Seven artists, created a truly Canadian vision of our country through direct contact with nature and our awe-inspiring landscape. Their work was notably distinct from the prevailing British styles of Turner, Constable and later British or European artistic styles.

Canada’s Centennial in 1967 marked a major inflection point for Canada. We had come through two world wars with a strong sense of national identity, supported by the burgeoning post war economy. Canada proudly led on the world stage with the likes UN Peacekeeping, Expo ’67 in Montréal and the uber cool federalist Prime Minister Pierre Elliot Trudeau.

Set right in the middle of the swinging 1960’s, our centennial celebrations in 1967 were a wonderful time to be alive. Besides Expo ’67 and the quaint historical “centennial” costumes people wore, today we are left with innumerable Centennial arenas, parkways, libraries, etc. These major investments in infrastructure are present with us today. I recall that time with pride and fondness.

CFC Smart and Caring Project:

Because the 21st Century seems so different than the previous, what kind of movement should honour Canada’s 150th birthday. It is a complex question, but I believe that if we can mobilize almost all communities across Canada into activities and projects inspired by the “Smart and Caring” mantra, like a national pot luck dinner we would effectively crowdsource some of national, and even, international significance.

Once again, we have a unique opportunity to make positive changes while setting a positive example for the world.

It is important to understand that, because each and every community is unique, communities must have the freedom to launch initiatives that directly suits their unique needs.  Nonetheless, with diverse initiatives considered collectively, I believe that, taken as a whole we can shape and inspire the Canada of the future.  We have so many advantages and the time is right to embark of nation building for the 21st century.

I would further hope that we would see collective action and partnership, both at the community level and national level, to increase the impact and effectiveness of the Smart and Caring 2017 initiatives. We must speak to and be meaningful to all Canadians:

  • young and old
  • recent immigrants or multi-generational Canadians
  • from east to west to the most northern reaches
  • Aboriginal, English, French or any other heritage

Because no group, no matter how large, can be sufficiently inclusive, that is why it is absolutely imperative that we, who have been honoured to help make this happen, hear from as many Canadians as possible.

Please weigh in here with comments or find other ways to get involved. And, I hope to provide more updates and opportunities to engage, participate, shape and drive Canada’s 150th birthday celebrations – Smart and Caring 2017.
Please start by sharing your thoughts on what Smart and Caring 2017  means to you.

A J Casson – The White Village




Ice Storms Highlight Canada’s Obsolete Infrastructure

January 1, 2014

As we enter 2014, well into the 21st Century, one lesson for me from the year just past was that Canada seems to be hobbled with 19th century infrastructure. Let me explain.

During 2013, my home in Ontario was subject to not one, but two, different ice storms – in April and December. Both brought down large chunks of trees and

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Business Strategy

“How ya gonna keep ‘em away from harm?” – The Sequel

November 22, 2012

Almost four and a half years ago, I penned what some called the obituary of Blackberry (see “How You Gonna Keep ‘Em Down on the Farm”). My intentions in writing that missive were, in fact, quite the opposite.  Back in 2008, a year after the first iPhone, Blackberry didn’t appear to be heeding the threat of major market disruption, let

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Business Strategy

Tech Terroir

October 29, 2012

In the world of wine, the concept of terroir describes a centuries long process in which the climate, soil, grape varieties and dedicated vintners, symbiotically develop a unique “sense of place” for a wine region. A favourite of mine, the garrulous  and quintessential Californian vintner, Randall Grahm, while trying to establish the old World notion of terroir in California postulates that it

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{Book Review}: The Innovator’s Dilemma

September 2, 2012
Book: The Innovator's DIlemma
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The Bun Reunion “AfterMath”

August 17, 2012

After welcoming people to the 050th Reunion of the ‘Bun and other 1970’s computing at University of Waterloo in mid-August 2012, I’ve gathered together a photo album, the brief presentation from the Gala and the many comments received outside of the earlier blog post.

Before the Gala, almost 100 photos were gathered which have grown to almost 250 contributed by various attendees.

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Business Strategy

Have Lean Startups Helped Us Scale Larger Technology Companies?

August 4, 2012

Building larger technology companies is critical for our future economic well being, yet somehow we seem to pay more attention to the seed and startup phase. This post and a subsequent missive, Wisdom from Recent Waterloo Technology Acquisitions, aim to analyze some recipes for building technology businesses to scale first from the perspective of recent companies and then specifically through the lens of local acquisitions.

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