a cold outreach workshop

“cold emailing is hard”

“how do I add value?”

“how do I craft a good cold email?”

When people overhear me talking about my 80% reply ( not just opened ) rate on cold emails, these are some of the common responses I would get. Recommendations on cold outreach is one of the most common requests I hear.

Why should you care about cold outreach?

Everyone now has digital ID’s of sorts, whether that’s social media or email addresses. Most of this is public information, and democratizes access to people we probably would have struggled to connect with in the past. Well-thought-out cold outreach gives you access to world-renown artists, entrepreneurs, journalists, investors, you name it. It’s especially useful that now most of our communication is moving digitally. Industry leaders like Brianne Kimmel, GP of Worklife Ventures, are even encouraging people to send that cold email you’ve been thinking about now.

Brianne Kimmel on Twitter

Career advice: if you’ve ever thought about cold emailing someone, do it. We’re all bored and here to help ☺️

So how do you get started?

That’s exactly what I covered in my cold outreach workshop on Zoom this past Monday for San Diego State’s Finance & Investment Society. Below is a detailed outline of my presentation (slide & the video recording are included at the bottom).

Here’s what people had to say about the workshop & their results:

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There are essentially five components of successful cold outreach.

• PURPOSE
• PERSPECTIVE
• PROCESS
• PREP
• FOLLOW THROUGH

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purpose

the purpose of your cold outreach will determine your medium, tone, level of personalization, and call to action. from my experience, it usually falls into a few different buckets: 1)pure admiration 2) career advice 3) specific asks about career opportunities. I usually stick to email for the first one, because it’s a longer, more formal medium – and twitter/linkedin for the second two.

I stick to roughly three mediums for outreach (listed in order of my favorite medium)

1. email – it’s pretty normal nowadays for people to be chained to their inboxes, so writing a thoughtful cold email has almost always gotten me a response.
   • er on the more formal side here. I usually avoid “mr.” / “ms.” as those are a bit too formal for me, but I would recommend letter formatting. try to stick to one or two paragraphs at most, make sure your signature has links to your personal website/linkedin.
2. twitter – people’s professional & personal lives blend a lot. I’ve had great success developing relationships by sharing sector-specific memes, music recommendations, quick appreciative notes. much less formal than email.
   • my tone typically is a lot less formal here, more of a friendly reach out than a structured one. I would advise referring to one of their past tweets & responding back and forth publicly before dm’ing.
3. linkedin – i have a love/hate relationship with linkedin. it’s great to find mutual connections for possible warm intros but it’s just so sales-y (good & personal outreach stands out here though)
   • add a note when connecting, which gives you 300 characters to explain yourself (much shorter message)
   • I usually don’t accept invites to connect without a note if we haven’t met in person, and most professionals share this stance.

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perspective

one thing that needs to be established before you begin your cold outreach process is a change in perspective.

someone asked me during our workshop, “how can I add value to this successful person’s life?” which is a question I often asked myself. when I began to write and then be on the receiving side of these outreach emails/texts/dms – I began to understand.

every blog post someone writes takes hours or even days to compose, sometimes years to come to the realizations and techniques arrived at in these pieces. then they post it. and wait.

for some, writing is therapeutic, a way of learning for themselves. for some, writing is personal branding, a way of posturing themselves. for some, writing is helping, a way of serving others at scale with information.

for all, writing is time-intensive.

giving specific feedback on something someone spent a lot of time developing & writing is adding value.

Being appreciative is a value add.

Some other notes on the subject of perspective:

people…

• generally like to help others, especially students
• appreciate intellectual curiosity
• like getting appreciative emails – think of your own mailbox with so many spam emails
• are afraid of “FOMO,” missing an intro to amazing talent / future star
• do their jobs everyday, so talking to someone that’s really interested helps them respark their passion & learn new perspectives

with that framework in mind, let’s move into the how to do cold outreach!

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process

start with a google spreadsheet with the following columns:

names / linkedins / twitters / emails / cities / positions/ companies / blogs / notes 

*take special care to make note of mutual interests

gather interesting people’s names from these sources:

• alumni directories
• linkedin advanced search [your college] + [dream job]
• crunchbase advanced search ( 1 week free trials )
• twitter “clusters” of professionals who interact with each other a decent amount

then, pick the medium where they are most accessible/active & start drafting your message. your message should be human: short, concise, purposeful. my typical message consists of the following:

• how you found them
• your background
• what you appreciate about them 
• call to action / value add

please watch my recorded workshop or go through my slides for multiple thorough examples 🙂 (linked at bottom of the article)

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prep

there are a couple things I recommend you do in preparation for an intro call.

first – ask whomever you’re emailing with after confirming a date and time if they’d mind you sending them a calendar invite (the answer is always yes but it’s polite to ask before sending). the subject should be “[your name] @ company <> [their name] @ company]. the location should be “[your name] to call [their name] at [their number]” (or vice versa if they didn’t give you their contact information. the notes/description should include your intro email so they have context for the call. this is especially useful if your call is more than a couple days away.

second – conduct deeper research on whomever you’re speaking with. it will help you prepare questions & you might dig up additional mutual interests or connections.

third – prepare your personal blurb. mine usually goes a bit like this: “My name is Paige Doherty. I’m a senior at SDSU with a love of systems and a passion for venture capital. I spent the last 10 months as a growth equity analyst at TVC Capital(a SD-based B2B SaaS growth equity firm) and prior to that I was a software intern lead at Northrop Grumman for three years.” make sure you have a good 10-15 second elevator pitch prepared so you can explain your background on the call.

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the call

some notes for the call itself:

start with small talk. sports, travel, weather. (for these times, I’d recommend a simple ” hope you’re staying safe in these crazy times” & possibly a funny anecdote about your time at home – cooking, joe exotic, something you saw in their tweets etc)

when you want to transition to the rest of the call, wait for a natural pause in the conversation to say ” hey [their name], I just wanted to say how much I appreciate your time today & I want to be respectful of it. with that being said, I would love to hear about you and your journey, then I can share a bit of my background & passions, then if we have time, I’d love to ask you some questions.”

I’d recommend doing this in a gentle tone, as it can come off ~a bit much~ if done assertively. say the sentence like you’re meandering through a field, not like you’re late to a meeting & fast walking through the streets of New York.

I learned this technique at TVC, and it’s super useful for structuring intro calls, as people know what to expect from the get-go. People are usually impressed by your organization, and by giving them the “rules” of the conversation, you allow them to relax because they aren’t building those constraints in their head. I learned that establishing the “rules” of a meeting is really important from Priya Parker’s “The Art of Gathering,” which I’d highly recommend to help build your sense of empathy in meetings.

by having them talk about their background first, you’ll be able to hear their story from their perspective (which is awesome!), and more time to mull over questions you’d like to ask them. at the end of the call, make sure you have some questions to ask!

the last thing you should always say is thank you. (if you watch the video from the workshop, I drop a major question that I always ask at the end of phone calls as well).

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follow through

the first thing after getting off the call, write them a quick thank you email. include an anecdote from your call that made you smile/reminded you of something else, something new you learned about them, and that you appreciated their time.

I’d recommend having a blurb & resume on hand & updated for easy sending if they’d like to introduce you to someone.

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I hope you enjoyed this dive into my cold outreach process and that you’re all staying safe in these crazy times. I appreciate this time that we’ve (asynchronously) gotten to spend together. Thanks for reading/watching & I hope it helps!

If you’d like to stay updated, I’d love if you subscribed to my blog and/or followed me on twitter!

Paige Doherty on Twitter

if you make tiny angel investments, does that make you a cherub investor…asking for a friend

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slides & zoom recording

a cold outreach master class

a cold outreach workshop by paige doherty

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