Sunday Reads #102: Conflicts, Confrontation, and the Art of the Cold Email

Plus, an astonishing graph on career growth.

Hope you and yours are keeping safe (and sane).

I'm back again with the most thought-provoking articles I've read in the week. (in case you missed last week’s newsletter, you can find it here. And check out the compilation of my best articles, if you haven’t: The best of Jitha.me).

This week, we first talk about difficult conversations. As someone who doesn’t do well with conflict (me), how can I still ensure that I achieve the right outcomes?

Next, the art of the cold email. What do you do when you need to reach out to someone you don’t know?

And last, some link love. What’s new in the world of AI and robotics (of course), and a graph on career growth that amazed me (not in a good way).

Here's the deal - Dive as deep as you want. Read my thoughts first. If you find them intriguing, read the main article. If you want to learn more, check out the related articles and books.

[PS. If you like what you see, do forward to your friends. They can sign up with the button below.]


1. How to have difficult conversations when you don’t like conflict.

I hate conflict. It makes me very uncomfortable.

I've been reading (and experimenting with) ways to get more comfortable with conflict, so that my aversion to confrontation doesn't get in the way of important things.

This HBR article has five great tips on having difficult conversations. (It was sent to me by my wife - talk about giant hints).

Begin from a place of curiosity and respect, and stop worrying about being liked.

Lean into the conversation with an open attitude and a genuine desire to learn. Start from a place of curiosity and respect — for both yourself and the other person.

Genuine respect and vulnerability typically produce more of the same: mutual respect and shared vulnerability.

Focus on what you’re hearing, not what you’re saying.

People who shy away from conflict often spend a huge amount of time mentally rewording their thoughts.

You don’t actually need to talk that much during a difficult conversation. Instead, focus on listening, reflecting, and observing.

Be direct.

Address uncomfortable situations head-on by getting right to the point.

Don’t put it off.

Expect a positive outcome.

You’ll struggle to follow this advice if you continue to go into a conflict telling yourself, “This is going to be a disaster.” Instead, tell yourself, “This will result in an improved relationship.”

Hope you find the article useful. I did!

Further Reads.

One of the best books on the subject of confrontation and difficult conversations, is Crucial Conversations. You can read my summary of the book here. If you like it, check out the book on Amazon.

Listening is a critical skill in difficult conversations. So simple to explain, so hard to do. Another great HBR article on this - What Great Listeners Actually Do.

Good listeners are like trampolines. They are someone you can bounce ideas off of — and rather than absorbing your ideas and energy, they amplify, energize, and clarify your thinking.


2. The Art of the Cold Email.

Speaking of uncomfortable things, cold emails are right up there.

When I started a consumer internet company back in 2013, I didn't have strong networks in the space. All my previous experience was in strategy consulting, advising old-school companies.

So, when my co-founder and I needed to get marketing companies on our platform, we had no choice but to build connects from scratch.

Enter the Cold Email (and the warm email too - more on that below).

It's hard and awkward to write to someone you don't know, asking them for something you want.

But if you do it right, it can work! By the end of my startup's first year, we had deals with some of the most established FMCG majors in India. As well as India's largest loyalty platform.

As I think back on what worked and didn't work then, there were a few important learnings.

Lesson 1: Before sending a cold email, first try to send a warm one.

First, always try to get a "warm introduction" to the target. Check who your common contacts are on LinkedIn, and see who can connect you.

Cold emails do work. But warm emails make it a LOT easier!

My co-founder and I were lucky enough to have second degree connects to some of our key targets, and this helped us get a few of our earliest deals.

But what do you do if you don't have any warm connect to the people you want to reach?

Lesson 2: Make a list of targets. A LARGE list.

For cold emails to work, you have to send a LOT of them.

Many of your targets will filter out. So, having just a Plan A ("Elon Musk is the perfect person for me to speak with, I don't need anyone else.") is not enough. You need to think broader about the kinds of people who can help you, and reach out to them all.

(And who knows, one of them may introduce you to Elon Musk!)

Lesson 3: Be clear, succinct, and useful.

Do you like receiving long-winded emails, with the key message lost in all the detail?

Neither do I. And neither does this person you're reaching out to, who doesn't know you.

Be clear: what is it that you want? Make sure you spell it out.

Be succinct: for the first outreach, make it 5 lines max. No more. This is who I am, this is what I want, and this is why it's useful to you.

Be useful: this may be the most important of the three. Most people are nice and happy to help. But don't depend on the better angels of their nature. Tell them what's in it for them.

Lesson 4: Be persistent (but don't be a pain).

A key insight on cold emails is:

Someone you've mailed before is much more likely to reply to your next email, versus someone you're mailing for the first time.

The person you emailed a couple of times in the last month did not reply to your previous emails. But she may still reply to your next one (if only out of curiosity, having seen your name pop up 3 times in her inbox).

So, don't give up too easily.

But don't be a pain. Be thoughtful. Give them time to respond. A/B test different language, value propositions, etc.

Lesson 5: Make it easy to say Yes.

What do you need? If what you're looking for is a $20M deal signed in 2 weeks, your cold email campaign will fail. Don't even bother.

Make your ask easy to fulfill. In the first two emails, you might ask for a meeting (or Zoom call). If that fails, ask for quick answers to your key questions over email. And the fourth time, ask them a question they can reply to in one line.

This lesson is also applicable when making a deal (i.e., after your cold email campaign gets you the leads you need). You're much more likely to get a no-regrets pilot than a 3 year contract.

There's a great thread from Amy Cheetham, on how she used cold emails to break into investment banking. Bookmark it - some useful tips in there!


3. The World of Artificial Intelligence and Robotics.

Last week, I shared a bunch of articles on GPT-3, the latest language generator AI from OpenAI (it’s awesome).

Well, the folks in robotics aren't too far behind. Boston Dynamics' robot is now a gymnast!

When you combine this with GPT-3 and its flair for poetry, we're shortly going to see the world's first quotable gymnast.


4. The graph that surprised me the most this week.

This is a chart showing the birth year of newly-hired CEOs of Fortune 500 / S&P 500 companies.

Avg. birth year of newly appointed CEO in 2005 = 1959

Avg. birth year of newly appointed CEO in 2019 = 1960 (!)

So what’s the best predictor of becoming a CEO of America’s most successful modern institutions? Being a baby boomer?

More on why this is the case, in The Boomer Blockade by Paul Millerd.

I'd love to see such an analysis for India and Asia as well.


That's it for this week! Hope you liked the articles. Drop me a line (just hit reply or leave a comment through the button below) and let me know what you think.

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See you next week!

Jitha