This simple hack makes email introductions more effective

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, they can be incredibly useful in connecting directly with an elusive executive. On the other hand, they can suck up a lot of time (and lead to bruised egos) if not done with tact.

The very worst email introductions automatically assume that the connection being made is appropriate and beneficial for 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 can’t find a time to meet without a lot of calendar shuffling.

I used to accept blind introductions (and subsequent meetings) like these in the past 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 strategy or operational challenges. Eventually, it became too much.

Nowadays, when it comes to email introductions, I try to model the behavior I want to see. 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 Uhura.

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 will be great if you can introduce me to Uhura. 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 Uhura (without including Pavel). My addition would provide further context and could be something along the lines of: “I don’t know Uhura well and I haven’t tried her products, but the elevator pitch sounds relevant to you” or “Uhura 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 Uhura agrees to the introduction, then I add Pavel to the thread. If she 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

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!

The End of 8-Hour Days

Both my parents used to work for a bank. For them, the work day started at nine in the morning and ended at 5:00 pm sharp. Day in and day out, this was their routine. They never understood the concept of flexible hours. They questioned why I would bring “work” home. On the other hand, they were always amused that I never needed to take time off work to see the doctor or get the car fixed during office hours.

“Am I expected to work an 8-hour day?” I get this question from employees from time to time, but I believe this is the wrong question to ask. Employees are expected to get their work done, deliver on OKRs and contribute to a positive workplace culture. For the most part, I don’t (and neither should their direct manager) care where or how the work gets done. Of course, it goes without saying (but I’ll still say it), flexible work hours should never impact collaboration or attendance at critical meetings.

Startups are fast-paced, ever-changing environments filled with bright employees. They’re solving complex and fascinating problems and it’s all very exciting. Being a disruptor and part of a paradigm shift is thrilling and the work itself should compel employees to give 100%. Offering flexible hours instills trust in your team and gives employees a sense of ownership to execute on projects in the way that works for them.

That’s not to say there will be no instances when burning the midnight oil for a specific project or tight deadline is required. Make no mistake, there will be times when a critical security issue needs to be addressed after-hours or a client has an urgent need on the weekend. But there should also be opportunities to take it easy and spend a few weeks out of the country or deal with a family or health issue. It’s about flexibility.

Most startups offer flexible hours, and it makes sense. After all, tech is a creative industry unlike working at a bank or factory. As people head back to work after their relaxing summer vacations, my advice to founders and startup execs? Measure productivity by outcomes and results, not timecards.

Your Next Summer Challenge: A Digital Detox

I love gadgets. They surround me everywhere – in the office, in the car, at home. I’m always connected … except when I go completely off the grid.

Twice a year I unplug for 2-3 weeks. I turn off my data. I don’t reply to email. I stay off social media. I take a break from being an entrepreneur and focus on being a husband and a dad.

It’s during these weeks when I’m unplugged that I have an opportunity to reflect on the past challenges and think about future opportunities. Going off the grid gives me a sense of clarity and enables a freedom of thinking I can’t achieve when I’m constantly pulled in multiple digital directions.

Case in point: I recently spent three weeks in Asia with my family. While I’ve traveled throughout the region extensively for work, this was the first time I could experience cities like Taipei and Shanghai as a tourist. I got to enjoy a ride on the fastest train in the world, eat the most delicious food, and shop like the locals do. I observed, indulged and enjoyed without the need to constantly check my devices. And while I was technically off-the-grid and not working, my offline experiences provided me with inspirations I will take back to the office.   

Building a business is hard. Entrepreneurs have infinite to-do lists. They are constantly pushing ahead through one challenge to seize the next opportunity. While the line between work and personal life is becoming more blurry (especially when you’re scaling a startup), it’s critical that entrepreneurs carve time out of their hectic schedules and go offline. A digital detox – even for a short period of time – yields tremendous business and personal benefits.  

If you still have a summer vacation planned,  I challenge you to use your time to explore, discover and connect IRL.

The Evolution of an Entrepreneur

Years ago, a summer job gave me one of the most valuable lessons in entrepreneurship.

I needed tuition money for university so I got a job at a factory printing t-shirts. I witnessed firsthand how the owner juggled multiple and often diverse tasks in order to operate a successful business. Looking back, I was naive to think that a t-shirt printing company was just about printing t-shirts.

If you look at the journey of an entrepreneur, it all starts with an idea. But an idea is just that – a thought. Without execution, an idea is as good as yesterday’s newspaper. Only when execution follows an idea, can you determine if there’s product-market fit. If you achieve product-market fit – congratulations, that’s a major accomplishment! You can start a company to further iterate on the idea and cement your place in the market. But once you start a company, you have to turn it into a business.

I’ve personally gone through this journey three times. My first business failed, I sold the second one, and the third has become one of Canada’s most successful startups. My experiences failing and succeeding as an entrepreneur reinforced the lesson I learned that summer many years ago: As an entrepreneur, the best product you can build is yourself.

You will wear many hats throughout the entrepreneur journey. As your company grows, you play different roles in the company and you can expect to change ‘jobs’ every few months. Each new job requires a different skill set. You may start as the product designer, but soon you’ll lead a team as a manager, and then eventually you transition into a leadership role.  I have yet to meet a single person who, at the launch of their company, has every required skill. So welcome continuous learning and crave self-improvement.

Taking the time to build yourself as a well-rounded entrepreneur will pay dividends.