How-To

Embrace Risks, Execute with an Edge and Seek the Asymmetrical Upside

On Friday, October 17, 2025, Chancellor Kathleen Taylor at York University conferred on Eva Lau the degree of Doctor of Laws, honoris causa.

I purposely avoided hearing her practice so I could experience it on stage for the first time, just like everyone else in the audience.

It turned out to be the right call. By taking the risk of not previewing it, I gained an asymmetrical upside! Ironically, these are the lessons she shared. Frankly, I wish someone had told me these lessons when I was in my twenties.

Please read her remark when you have a moment:

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Dean Zwick, faculty, honoured guests, proud families, and—most importantly—the graduating class of 2025: thank you. It is a profound honour to stand before you today.

First, I want to thank the school for recognizing my work in entrepreneurship and innovation and granting me this extraordinary honour.

I also want to thank my mom and my late father, whose leap of faith to immigrate to Canada opened the doors for me and my sister to build our lives here.

To my daughters—you’ve been my biggest motivators. You are the reason I push forward, because I want you to know your potential is uncapped. You can chart your own paths and build your own successes.

And to my husband, Allen: thank you for your love, support, and affirmations. You mean the world to me, and you make me a better person every day.

And to the graduating class—congratulations! Today is a celebration of your hard work, your determination, and your costly Red Bull habits. It is my greatest joy to share a few words with you. Since we are all business school graduates, let’s get straight to business. I want to share with you a strategy—a framework, at least for me—on how to calculate risk, how to execute with an edge, and how to maximize the upside, to a point that it can be transformational. That’s right, I am putting our education to work here. No group project required!

Lesson 1: Embrace Risk—But Know Your Bottom Line

In school, we learned about Risk Management in Finance. Identify the risks. Quantify them. Mitigate them. Protect value. Very neat, very rational.

But in life, risk doesn’t come with a spreadsheet. In life, managing risk means asking: how much am I truly willing to lose? Unless you define that, you can never truly take a risk.

When people read about the success of Wattpad, the story can look deceptively simple. We built the product. Users loved it. The product went viral. And ta-da! It became one of the most iconic internet platforms in the world, serving over 100 million users worldwide, sharing over 1 million new stories in 50 languages every day. We even have TV and movie products around the world. When the company was acquired in 2021, it was one of the most significant tech exits in Canadian history.

But the “ta-da” moment was actually years of sweat, doubt, and very small numbers. At the start in 2006, Wattpad didn’t just have few users—we had so few that our total ad revenue was…two dollars. Not two million. Not two thousand. Not twenty. Just two. And Allen and Ivan, the two cofounders, had to split it. I think one bought a coffee… the other just got the receipt.

Our family’s finances? Let’s just say “tough” doesn’t quite capture it. We were running low on savings and even had to leverage our house to keep everything going. Allen and I had many long kitchen-table talks. In the end, we decided we were willing to risk everything—even selling the house—if that’s what it took. But we drew a firm line: we were willing to go down to zero, but we were not willing to go into the negatives.

That’s what embracing risk looks like for an entrepreneur. It’s not about avoiding loss. It’s about defining your boundaries and then giving it everything you’ve got. Try your hardest to stay clear of the bottom line.

And when mobile computing took off with the launch of iphones and android devices, all that persistence paid off. Wattpad became the world’s number one story-sharing app on all app stores.

We took the same approach when exploring new frontiers at Wattpad—first with AI, then with entertainment. In 2012—long before “ChatGPT” became a household name—we became one of the first companies to deploy AI at scale on a commercial platform. It was a bold move, and yes, a risky one. Then in 2016, we leapt into film and TV production—an entirely different world for us. Both were high-stakes bets, but because we had clearly defined what we were willing to invest and what we were prepared to lose, we could take those risks with confidence.

So my first lesson: embrace risk. Define your bottom line so you can move forward without fear. Knowing your worst-case scenario gives you the freedom to take that leap of faith. In your case, living in your parents’ basement could be the worst-case scenario. But hey, you already know them well enough. I think you will survive.

Lesson 2: Leverage Your Uniqueness

Once you’ve defined your risk boundaries, the next step is execution. And here’s the secret: the best execution comes from knowing what makes us unique and leaning into it.

When I began my journey as a venture capitalist a decade ago, I knew I couldn’t just be another investor. What set me apart was lived experience: I had scaled a product from a few thousand users to tens of millions. I understood the fear, the pivots, and the sleepless nights—not from theory, but firsthand.

Before Wattpad, I worked in a semiconductor company, managing a product line that was competing with a startup at the time, called Nvidia. AMD later acquired the company for US$ 4 billion. That experience gave me the technical and operational lenses very few investors had.

And then there were my learnings from some of the best investors in the world—people who backed Twitter, Coinbase, Google, and even OpenAI. I had the opportunity to learn directly from them since they were also Wattpad investors.

All of that shaped my unique edge as a venture capitalist at Two Small Fish. With a distinct investment thesis, we became one of the few deep-tech investors in Canada, backing founders tackling hard technology problems with novel innovations. Today, I’m proud to say Two Small Fish is not only among the top-performing VC funds globally, but also a firm that founders love working with—because we do things differently.

That’s the second lesson: know our uniqueness and use it. Don’t downplay it. Don’t hide it. It’s our superpower.

Lesson 3: Chase Asymmetrical Upside

The third lesson is about aiming high. Really high. Chase the Asymmetrical Upside.

Entrepreneurship and innovation are not about making something just 10-20% better. They are about creating something 100 times, 1000 times better. Something transformational.

If you only focus on small, incremental gains, you might survive—but you won’t thrive when the next wave of disruption comes. But if you go after opportunities with asymmetrical upside—where the potential payoff is massive compared to the risk—you position yourself for breakthroughs.

Take Wattpad again. If we had only wanted to build a small reading app for a niche audience, that would have been fine. But by dreaming bigger—by imagining an AI-powered global entertainment company—the outcome was transformational.

And this applies to your careers too. You won’t change industries—or the world—by playing it safe. You have to reach for opportunities that feel a little terrifying, a little out of your league.

I like to remind young entrepreneurs: I have never seen a basketball player aim for the bottom of the net. They always aim above it. That’s how slam dunks happen.

So my third lesson: don’t settle for small steps. Chase the opportunities that stretch you, the ones that scare you, the ones that could redefine everything.

So, Class of 2025, to sum these up, I encourage you to:

  • Embrace risk. Define your boundaries. Know how much you’re willing to lose, and let that clarity free you.
  • Leverage your uniqueness. Don’t try to be a knockoff of someone else. Your unique mix of experiences, skills, and quirks is your competitive edge.
  • Chase asymmetrical upside. Don’t aim for incremental change. Aim for the slam dunk.

Your journey will not be a straight line. There will be pauses, setbacks, and zigzags. But each twist is part of the story that prepares you for the next leap forward.

So step into your future with courage. Take the risk! The world doesn’t need another safe bet—it needs bold leaders, innovative thinkers, and dreamers who are willing to take the shot.

Congratulations once again, Class of 2025. The future is yours—go and dunk it.

Masterclass Series: The Rule of 3 and 10 — Lessons I Wish I Learned Earlier

One of the most powerful frameworks I’ve come across is the Rule of 3 and 10, coined by Hiroshi Mikitani-san, founder and CEO of Rakuten. The idea is simple: every time a company triples in size, everything breaks.

As Rakuten grew from a handful of people into a global business, Mikitani-san noticed a clear pattern. At each stage — 1 to 3 people, 3 to 10, 10 to 30, 30 to 100, 100 to 300, and beyond — what worked before suddenly stopped working. And by everything, it really does mean everything: payroll, meetings, communication, budgeting, sales, even the org chart. The challenge is that many leaders blow right through these milestones without realizing what’s happening until it’s already broken.

What I Wish I Knew

I’ve been part of many really fast-growing companies — first as an employee, and later as a co-founder in two of them. And I can tell you, this rule is 100% true.

At Wattpad, I didn’t fully internalize it until we were approaching 100 people. By then, we had already missed natural breaking points where we could have rebuilt earlier. That lag made scaling harder than it needed to be.

Looking back, the stages feel something like this:

  • At 3 people, you’re a tight-knit unit where everyone knows everything.
  • At 10, you need to change how you communicate just to stay aligned.
  • At 30, the days of everyone reporting to the CEO are long gone — a first layer of leaders emerges.
  • At 100, there are layers of layers of leaders, and even well-designed systems need rethinking.
  • At 300, you’re running a completely different company than the one you started.
  • At 1,000, it feels like a mini-society with its own subcultures, bureaucracy, and politics — alignment becomes the hardest problem of all.

The Employee’s View

Before becoming an entrepreneur, I lived through this as an employee too. The breaking points are just as visible from the inside.

As companies scale, it gets harder to push things through. Meetings multiply, but decisions slow. Bystander problems appear — more people in the room, but fewer actually taking ownership. From the employee’s perspective, it feels frustrating and inefficient. But it’s not about capability; it’s about systems that no longer fit the size of the company.

Why This Matters

In the moment, it can feel like failure. But it isn’t. It’s simply that scale changes everything.

The good news: these challenges are solvable. Every growing company has faced them. The bad news: if you only react after things break, you’ll always be catching up instead of leading.

My Takeaway

If you’re building a fast-growing company, expect everything to break at 3, 10, 30, 100, 300, 1,000… and plan for it.

Don’t see it as failure. See it as evolution. Each breakdown is proof you’ve unlocked a new stage of growth. The chaos is part of the privilege — it means you’re building something worth scaling.

If I could go back and tell my younger CEO self one thing, it would be this: anticipate the breaks before they happen. Build a culture that embraces reinvention at every stage. You’ll save yourself and your team a lot of unnecessary pain — and you’ll enjoy the ride more.

P.S. The banner is using Ideogram Character to generate. It rocks!

P.P.S. If you enjoyed this blog post, please take a minute to like, comment, subscribe and share. Thank you for reading!

This blog is licensed under a Creative Commons Attribution 4.0 International License. You are free to copy, redistribute, remix, transform, and build upon the material for any purpose, even commercially, as long as appropriate credit is given.

Perhaps My Title Should Be…Yoda?

Yesterday was Star Wars Day — aka “May the Fourth be with you” — and it got me thinking, so I put together this blog post.

You might notice my title is “Operating Partner,” not “General Partner,” “Managing Partner,” or “Board Partner.” That’s intentional because I spend most of my time working directly with portfolio CEOs.

The Operating Partner role has its roots in private equity. Historically, Operating Partners are often former CEOs or COOs who use their experience to guide leadership teams, improve operational execution, and drive results, ultimately increasing the value of portfolio companies.

As far as I know, I’m the only former scale-up CEO in Canada who plays this role in an early-stage VC. At least, ChatGPT and Perplexity couldn’t find anyone else! Even in the U.S., this is very rare.

That said, I’ve always felt the “Operating Partner” title is a bit misleading. Unlike many private equity Operating Partners, I don’t step into full-time or part-time leadership roles within portfolio companies. I don’t give advice or directives either. Instead, I help CEOs solve their own problems rather than solving problems for them.

My single objective is to help portfolio CEOs improve the quality of their decisions by leveraging my experience.

Why? Most CEOs don’t need to be told what to do—they already know. Telling a CEO to grow their KPIs faster or hire great people is useless.

No CEO intentionally grows slower or hires bad people!

The real challenge for CEOs isn’t the what—it’s the how. This is where I come in, helping them navigate the how: strategic thinking, future-proofing, and decision-making that drive tangible progress, while staying alert to blind spots that could undermine success.

Hiring is an example. Many venture firms have talent partners who assist portfolio companies with recruitment. These partners, often from recruitment backgrounds, are excellent at sourcing candidates once roles are defined. However, they usually lack deep business context and may not fully understand the culture of the companies they’re supporting. This can result in untargeted candidates who don’t fit. I experienced this issue firsthand when I was a CEO.

That’s why I strongly favour internal recruiters who have an intimate understanding of the business and culture. Even so, recruiters typically get involved after roles are clearly defined. Before that, to design the organization, we need someone who has visibility into the broader perspective of the business. Only one person truly has it: the CEO. Besides, CEOS usually can’t ask their leaders about organizational design for obvious reasons.

That’s where I step in—well before recruiters are involved. I act as a sounding board for organizational design, considering not just immediate hiring needs but also how roles and teams will evolve over time. What level of talent should they hire now? When will this position need to level up? What downstream implications will these decisions have?

By addressing these questions early, I help ensure hiring decisions are aligned with the company’s long-term strategy and culture.

Of course, hiring is just one area where I provide support. Design future-proof stock option plans? Manage internal and external communication challenges? Interact with strategic conglomerates? Navigate inbound acquisition offers? Resolve leadership dysfunction? Handle unreasonable investors? Make board meetings more effective? Fend off super aggressive competitors or internet giants?

And yes, one of the most frequent requests I get is: “Can you help me with my pitch deck?”

Bring them on!

I’ve faced these challenges firsthand multiple times, and when CEOs bring them to me, I’m ready to share my war scars.

At the minimum, I help narrow the options from “I don’t know how” to a set of multiple choices. I don’t make decisions for CEOs; I help them make better ones. They are ultimately responsible for their decisions, and I see my role as a guide, not a decision-maker.

Being the CEO of a fast-scaling company is an enormous challenge that people should not underestimate—the level of experience, capacity, intensity, and mental strength that one needs to cope with. That’s why it is the loneliest job. Empathy is not enough. The best help I ever got was from a more experienced CEO than me at the time — someone who had walked the road ahead — and now it’s my turn to pay it forward. It is payback time for me.

The more I think about it, the less “Operating Partner” seems to fit. I don’t step into the spotlight or take over operations. My role is more like Yoda—helping Skywalker fight the battles while staying behind the scenes.

So perhaps my title shouldn’t be Operating Partner after all. Maybe it should just be… Yoda.

May the Force be with you!

P.S. If you enjoyed this blog post, please take a minute to like, comment, subscribe and share. Thank you for reading!

This blog is licensed under a Creative Commons Attribution 4.0 International License. You are free to copy, redistribute, remix, transform, and build upon the material for any purpose, even commercially, as long as appropriate credit is given.

Masterclass Series: Use This Framework to Move Fast and Make High-Quality Decisions

In many companies, the bottleneck isn’t necessarily in the execution of decisions. The real bottleneck is the excessive time people waste making decisions.

When I was Wattpad’s CEO, everyone in the company knew I had a simple 2×2 framework to empower the whole team to make fast, high-quality decisions – all by themselves!

The essence of this framework comes down to two questions:

• Is this decision reversible?

• Is this decision consequential?

These two factors create four types of decisions:

1. Reversible and inconsequential

2. Reversible and consequential

3. Irreversible and inconsequential

4. Irreversible and consequential

Examples of Each Type

1. Reversible and Inconsequential

This actually makes up the bulk of decisions in a company:

• Internal Slack messages? Delete them if you don’t like them.

• Marketing team’s benign social media copy? Remove the post if it doesn’t work.

• Small typo like the one in the above image? Yes, I purposely left the typo there. I look sloppy, but I could silently replace it with a better one when I have time.

• Small bugs in the product? If a bug fix causes other problems, revert the changes.

The list goes on. The trick is to empower each person in the company to make these decisions independently. I reinforced the same message to the Wattpad team over and over again:

From the most junior interns to the most senior leaders—you’re empowered to make the call all by yourself.

No boss to ask. No approval process. Just do it!

The company moves fast when most decisions don’t require a meeting!

2. Irreversible and Inconsequential

Here’s an example:

At one point, we ran out of space at Wattpad’s Toronto HQ and needed overflow space. We found a small office—just a few hundred square feet with a couple of meeting rooms—in the building right next door. The location was perfect, but the space itself? Just okay.

The problem was the lease—it was relatively long. Once we signed, we couldn’t back out. That limited our flexibility (irreversible), but we knew that if we needed more room, we could always find another expansion space. The cost was small in the grand scheme of things (inconsequential).

Given our growth, there was little downside to signing the lease. So we moved fast, signed the deal, and moved on to the next item on the to-do list.

For this type of decision, you can still move fast. Just be careful—double-check the lease for any hidden “gotchas.” It’s not about if we sign or not. We will sign, but we just want to make sure the bases are covered before we do.

You’d be surprised how much time people waste on indecision. Just make the call and do the due diligence!

3. Reversible and Consequential

A perfect example? A big product release.

Sonos’ poorly executed product release is a great case study. (See my blog post Masterclass Series: Complete Redesign That Actually Works for all the details.)

When done properly, product releases can be very consequential but still reversible. At Wattpad, we released high-risk software all the time—but always with a way to roll back if things didn’t work.

We knew how to press the undo button!

For these kinds of decisions, move fast and make the call—but monitor the outcome and always be ready to press undo.

Important: How to Increase the Quality of These Decisions

For both Irreversible and Inconsequential decisions and Reversible and Consequential decisions, always ask:

Is there any way to make this decision more reversible or less consequential?

If you can tweak the decision to minimize fallout—no matter how small—do it. It will save time and stress down the road.

4. Irreversible and Consequential

Many of these are leadership-team-level or CEO-level decisions.

They’re rare but also the hardest to make. They require a lot of context, consideration, and, sometimes, choosing between two bad options. Occasionally, you get a good one and choose between a few great choices.

The ultimate example for me?

Whether to take the company public, maintain the status quo and keep going, or accept an acquisition offer.

You all know the decision I made.

Sometimes, knowing which quadrant a decision falls into is an art. But imagine if we didn’t have this framework—slow decision-making would have ground the company to a halt.

The key to moving fast isn’t just execution—it’s deciding fast, too.

P.S. If you enjoyed this blog post, please take a minute to like, comment, subscribe and share. Thank you for reading!

This blog is licensed under a Creative Commons Attribution 4.0 International License. You are free to copy, redistribute, remix, transform, and build upon the material for any purpose, even commercially, as long as appropriate credit is given.


How to make meetings suck less

About a year ago I read an article about Jeff Bezos’ approach to meetings at Amazon that really resonated with me. Specifically, there were three things that make meetings more effective and efficient that really stood out to me.

  1. The Two-Pizza Team Rule – According to Jeff Bezos, Amazon tries to “create teams that are no larger than can be fed by two pizzas”
  2. No PowerPoint – “No PowerPoints are used inside of Amazon,” Bezos proudly declares. “Somebody for the meeting has prepared a six-page…narratively structured memo. It has real sentences, and topic sentences, and verbs, and nouns–it’s not just bullet points.”
  3. Start with Silence – “We read those memos, silently, during the meeting,” says Bezos. “It’s like a study hall. Everybody sits around the table, and we read silently, for usually about half an hour, however long it takes us to read the document. And then we discuss it.”

Like Bezos, I’m a big believer in small group meetings. Based on my experience, it’s too difficult to have a conversation that’s relevant to most if there are more than eight people in the room.

I don’t necessarily 100% agree with no PowerPoint, though. Yes, there are times when having a narrative works better, but in some cases, bullet points can be more effective. One can’t replace the other. Use the right tool at the right time for the right people.

What I found really interesting is the study hall format. Since learning about, I’ve tried it out in multiple meetings by allocating the first 5-10 minutes (not 30 minutes as Bezos suggests) so everyone can go through the document or deck and add their questions and comments in advance of the discussion. Here’s what I observed:

The Pros

  • It ensures everyone has read the materials and the context is fresh in people’s mind (and yes, I know meeting organizers can always send materials in advance as pre-reading, but people still have to carve out time in their schedule to get it done. This is especially difficult for people who attend lots of back-to-back meetings).
  • It provides dedicated time for pre-reading that is already built into the meeting (similar to the point above)
  • It helps reduce the amount of context switching so the quality of the conversation goes up noticeably because the context is so fresh in everyone’s mind.
  • The quality of the questions improves because people don’t have to multi-task in the meeting, i.e. listen, read, absorb AND ask at the same time.

The Cons

  • It means less time to talk, especially when meetings are only 30 minutes long (but IMO, we get this time back in a way because we might have wasted those 5-10 minutes getting attendees up to speed anyway).

As you can tell, I become a fan of the study hall format, and while I recognize it doesn’t work for every type of meeting, it’s helpful when teams need to be on the same page with specific background information. That’s when spending 5-10 minutes to make sure everyone is “in the zone” is well worth it.

Incorporating the Study Hall format to your next meeting gives you time: Time for understanding; Time for extended reflection; Time for focused thinking; All of which leads to better and more effective meetings.

Your iteration rate is the key to finding product-market fit for your app

For any entrepreneur launching an app finding product-market fit is a lot like finding the Golden Ticket; it’s rare, but when it happens it’s life-changing.

Unlike an enterprise business, when you build a consumer app your end-user can’t easily tell you what they want (vs. enterprise apps that are focused on solving a known problem or a pain point for clients). Think about it this way: Before the iPhone launched, no consumer research would point out the need for a touchscreen, keyboardless device. Before Snapchat, no consumer would say they wanted the ability to send ephemeral messages.

Consumers aren’t able to tell you what they want; this makes consumer products a shot in the dark. There is no guarantee if or when product-market fit can be found. It’s usually a long journey of continuous iteration.

And ongoing iteration is what gets you to product-market fit. Each iteration gives you one extra at-bat. Hitting a home run is easy if you can strike out 10o times instead of 3. Y Combinator’s Sam Altman said it best in this tweet:

Screen Shot 2019-04-01 at 4.14.45 PM

Finding product-market fit is hard. Look at how many consumer products Facebook and Google shut down even with their massive resources (remember FB Paper, FB Groups app, Google+ app?) Massive resources can help, but it’s not the most critical.

In the early days of Wattpad, despite only having a handful of employees, every day the product looked a bit different. We implemented new concepts in the morning, checked in the afternoon, measured overnight and killed it the next morning if it didn’t work out. That’s how we found product-market fit in many things. And that’s how we left our competitors in the dust.

Although finding product-market fit is freaking hard, it is also very fun and rewarding once you have figured it out.

Keep on iterating!

Embrace tension to move even faster

As a startup scales, it’s natural for tension to creep up among different teams who are working on disparate objectives. Either of these conversations sound familiar?

“Showing users more ads can help generate more revenue, but it could also hurt engagement. Do we optimize for revenue or engagement?”

“We have a limited budget. If we spend it on A, B, and C we won’t be able to pay for X, Y, Z. What should we choose?”

The best way entrepreneurs can embrace and then ease tension among their teams is to establish a set of principles. Principles can help teams avoid indecision and move fast.

In the example above about serving ads at the expense of user engagement for instance, if the team has previously established that ad experiments can’t impact engagement by more than X%, it becomes easier for them to test different combinations of ads to drive the most revenue without negatively impacting engagement.

Establishing principles streamlines decision making, eliminates unnecessary meetings and propels the company forward. Everyone knows what to do and understands how much (or how little) leeway the team has.

Of course, there will be times when you may not have a principle to fall back on. That’s when the teams representing the conflicting priorities need to escalate the matter further and involve an arbitrator. Most times decisions are reversible and having an arbitrator can resolve issues quickly. In the world of startups, a quick decision always trumps a slow decision (or worse, no decision at all).  

Tension is natural and a sign your company is growing. But as your business grows and becomes more complex, decisions aren’t as straightforward as they used to. Creating a set of ground rules that inform your team’s priorities and outcomes can help avoid unnecessary confusion and conflict.

5 tips for better meetings people will actually want to attend

Over the years I’ve attended thousands of meetings. The best ones respected my time and input. They kept me engaged – and often excited – throughout the meeting.  And the worst ones … well, I’m pretty sure we’ve all attended at least a few terrible meetings and know what that’s like.

Having seen the good and the bad, I wanted to share some simple tips that anyone, at any level, can implement for more effective meetings.

Go beyond the agenda
Yes, circulating a clear agenda prior to the meeting is important, but also consider explicitly spelling out the objective and the outcome of the meeting. It gives participants the right context to prepare for and be fully engaged during the meeting (or decline the meeting if they can’t help meet the objectives/outcomes).

Nominate a facilitator
This person makes sure the agenda is followed and desired outcomes are met. They empower all participants to contribute and get the group back on track if the conversation goes awry. Facilitating meetings is a special skill and not everyone is good at it but if you find the right person, you are practically guaranteed a great meeting. Keep in mind that the meeting organizer doesn’t have to be the facilitator.

Limit participants
Keep meetings participants to 4-7 people maximum. In my experience this really is the sweet spot. Beyond 8 participants, the introverts in the group tend to shy away from voicing their opinions (a good facilitator, though, can help draw out their perspectives and ensure introverts have a voice).

Forget the update
Don’t use a meeting to provide or ask for updates. Save it for email, or better still a collaborative Google Doc. Share these updates in advance of the meeting as pre-reading material so you can focus the discussion on healthy debates and decision making.

Save 10
Use the last 10 minutes of the meeting to recap the discussion. This is crucial. You’ve just spent the last hour having a productive discussion, it would be a shame for it to fall apart in the follow-up. Make note of the essence of the discussion, key decisions made and actions to take. Be sure to share these notes with all attendees and other stakeholders who couldn’t join.

Slight tweaks to the way organize your meetings can have a profound impact. Know of any other hacks to make meetings more effective?  Let me know in the comments.

A Fast and Easy Way to Ask for Introductions

At some point in your career, someone you know will a) ask for an introduction to someone else in your network, or b) offer to make an introduction to someone they feel you should know.

Email introductions can be a double-edged sword. On one hand, obviously, they can be incredibly useful. On the other hand, they can suck up a lot of time if not done properly.

The very worst email introductions automatically assume that the connection being made is appropriate and beneficial for the involved parties. But the truth is, unless you’ve explicitly asked in advance, this is just an assumption.

Here’s an example of an email I recently received:

Hey Allen,

I would like to introduce you to Cindy Lou (cc’ed). Cindy Lou is an expert in X, which you will find useful. I’m sure you would enjoy the meeting. I’ll let you two find the best time to meet next week!

Cheers,
Horton

The problem is, while Cindy Lou might be an expert in X, I don’t really care about X; it’s just not my thing. Naturally, I don’t want to spend even more time feigning interest in X. And I definitely don’t want to waste Cindy Lou’s time either. The other problem: Despite what Horton thinks, I’m mostly out of the office next month, so I can’t find a time to meet without a lot of calendar shuffling.

I used to accept blind introductions (and subsequent meetings) like these out of politeness. It was an ineffective use of my time – and theirs. Even when I dared to say no, I had to spend time crafting a firm yet polite email to decline the opportunity. Drafting the email didn’t take up nearly as much time as a meeting would, but it still took time out of my day that could be better spent on other challenges. Eventually, it became too much.

Nowadays, when people ask me to connect them with someone in my network, I make sure I have a double opt-in. This means I’ve asked for—and received—the permission of both parties before I send a note. Here’s what it looks like:

Pavel would like me to connect him with John.

I’ll ask Pavel to send me a new, well-written email with the request (Pavel should NOT include our previous conversation i.e., the original request). It could look something like this.

Hey Allen,

As discussed, it would be great if you could introduce me to John. Here is a summary of my ask: <insert awesome summary here>

Thanks in advance for your help.

Live long and prosper,
Pavel

Then, I would add a sentence or two before forwarding the note to John (without including Pavel). My addition would provide further context and could be something along the lines of: “I don’t know Pavel well, and I haven’t tried his products, but the elevator pitch sounds relevant to you” or “Pavel is brilliant and working on a super interesting project you might be interested in.” This context setting is important, but should only take 30 seconds of your time.

If John agrees to the introduction, then I add Pavel to the thread. If he says no, I’ll let Pavel know that as well.

Double opt-in email introductions work well for a number of reasons.

  1. The onus is on the person requesting the introduction to write an awesome email detailing why the connection is valuable. It’s not the facilitator’s responsibility to make the case.
  2. It avoids putting people in an awkward position of accepting a connection or meeting when there is zero interest in the product/service/pitch.
  3. It encourages frank dialogue. If a person wants to decline an introduction, chances are he/she is more likely to provide a candid reason in a private one-on-one email with a trusted connection. It allows the facilitator to filter the information appropriately while still providing a truthful explanation to the requester.
  4. It allows for brevity without sounding cold. Since the facilitator has established relationships with both parties, a to-the-point email doesn’t come off as arrogant or rude.

One more thing—please don’t write the email as though it came from me. Each person has a unique writing style and voice, and I have mine, too. You won’t be able to capture my voice exactly.

I make lots of introductions, and I am more than happy to do so. It’s great for community building. I hope the double opt-in method helps make introductions faster and a better experience for everyone!