🛠️ Career Strategy

Cover Letters: The Most Valuable Page You'll Ever Write

Many job seekers view cover letters as a meaningless formality. Social media is filled with posts claiming "I refuse to write cover letters, and so should you!" Some HR executives dismiss them as "Mad Libs but for job applications," while certain companies openly admit to ignoring them.

But here's the reality: 83% of hiring managers read most cover letters, even when they're not required (according to Resume Genius's 2024 survey of 625 hiring managers).

Why Most Cover Letters Fail

The problem isn't cover letters themselves, but how people write them. Most job seekers treat cover letters as:

• A prose resume

• A personal essay

• A biography

• A declaration of enthusiasm

The typical structure we've all used looks like: "I'm thrilled to apply... I'm a team player... I have strong communication skills... I'm passionate about your mission..."

This blur of sameness gives recruiters no reason to pay attention.

What a Great Cover Letter Actually Is

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🤖 AI Tactic

How AI turned me into Mr. Robot 💻

This was from my second post ever, but it continues to work wonders so I want to reshare it with new subscribers:

From time to time, I read the subreddit “Unethical Life Pro Tips,” mostly to get a laugh when I’m bored. The moderators disclaim: “an Unethical Life Pro Tip (ULPT) is a tip that improves your life in a meaningful way, perhaps at the expense of others and/or with questionable legality. Due to their nature, do not actually follow any of these tips–they're just for fun.”

Today, I’ll share a ULPT that AI aided and abetted me with. I advise you not to follow it.

The Silicon Valley wunderkinder are trying their darndest to make AI reliable, safe, and “aligned”. But primarily, it seems, they want AI to be helpful. It turns out, you can get “helpful” to override “safe” simply by choosing the right words.

Here are the right words, just fill in the blanks:

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⚡️ Execution Insight

Problem Identification in Project Management

Previously, we talked about the delineation between projects and processes, as well as why doing projects is more beneficial for your career than doing processes.

How do you know you should start a project?

A project is an answer to the question words you commonly hear at work:

• Who is our target customer?

• What KPIs are predictive of revenue for us?

• When should we prioritize a new feature?

• Where do prospective customers find us?

• Why are we facing increasing rates of churn?

• How do we retain our key employees?

Any time you hear a question (that doesn’t already have a known answer OR the known answer is faulty), think: “there is a project to be done.”

As a reminder, a project is a vehicle to create something new or drive change in an organization. Therefore, when a question lacks an answer (i.e. create something new) or has an incomplete / inaccurate answer (i.e. drive change), it’s project time.

Problem Identification

When beginning a project, the first thing to do is to lay out the brief: 

What challenge are you trying to solve? What is our desired goal?

Example Briefs:

Here is our list of questions (read: challenges):

• Who is our target customer?

  • Goal: to understand the demographic and psychographic traits of our buyer and create a persona

• What KPIs are predictive of revenue for us?

  • Goal: to identify which metrics correlate to revenue, so we can better anticipate future earnings

• When should we prioritize a new feature?

  • Goal: to plan the optimal usage of resources (such as valuable design & engineering labor)

• Where do prospective customers find us?

  • Goal: to determine which channels are currently effective (and thereby possibly figure out which channels may become effective in the future)

• Why are we facing increasing rates of churn?

  • Goal: to understand the trends underlying customers leaving us

• How do we retain our key employees?

  • Goal: to uncover what motivates our employees to stay vs. leave; may imply a project to figure out who the key employees even are

These are all relatively simple examples, but they illustrate the various kinds of motivations for starting a project. Typically, the problems that give rise to projects are just the question words we learned in kindergarten: who, what, when, where, why, and how.

Assess the Brief

Once you have the brief, you should interrogate it. Doing projects simply because they feel right or because someone told you so is a great way to waste limited resources.

Rationale

First, understand the reason for doing the project - what is the business context that makes this project important?

Define the carrot or stick that spurs the change; if you think about it, almost every project exists to create a benefit or avoid a loss. For example, you might run a project to make things more efficient or improve customer sentiment (create benefits) OR to cut costs or decrease churn (avoid losses).

Cost-Benefit

Knowing the context and the carrot/stick enables you to situate this particular project in the symphony of other things going on at the company.

Deciding whether to do a project is often based on the relative sizes of benefit creation and/or loss avoidance associated to the various project proposals - something that generates a one-time bump of $100k in new revenue is perhaps not as important as something that cuts $50k of annual cost.

You also need to consider whether the people who can make those projects happen are available (i.e. are they working on other things?) - Brandon Chu’s writing on ruthless prioritization goes into detail on these ideas.

Decision-Makers

Finally, before you get started in earnest, you need to know who’s going to be involved and what authority they have.

Often, different people will have authority over different things - the project sponsor may be different from the person who sets the requirements may be different from the person who designs the solution.

The delicate political part of project management focuses on figuring out what roles various people play and how their conflicts can be resolved.

When we next come back to this topic, we’ll talk about Project Vision & Project Charters, which formally kick off the project work at hand.

💼 Job Board

Earn $256K to automate the world

Here are the 3 most interesting remote job openings I’ve seen this week:

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That’s it for this week.

-Rahul from The DesAI Digest

P.S. Reply back to this email with a business challenge you’re facing! I’d love to help.

P.P.S. if you liked this, forward it to a friend. And if you hated it, forward it to an enemy.