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At first, cover letters were great. They did the trick. But right now, they might just be the reason why no one has you called you yet.

That path is now a black hole. Employers no longer bother to look at cover letters, and new technology puts the last nail on this coffin.

What was once a warm interactive human process has been left to ruthless and talent-repelling systems with keyword-sorting mechanisms that squeeze all the life out of your resume or cover letter.

Enter pain letters, now your only ticket out of this black hole. The traditional cover letter would focus on you, but the pain letter does the exact opposite, and right now, it’s a more powerful way to stop your potential boss in their tracks and get them to think about your words.

But not every pain letter does that. That’s why I want us to learn how to how to write a pain letter to a hiring manager – the kind that will deliver that coveted feedback.

To begin with, see to it that you have the right answers to the following questions.

Do I Know My Potential Employer Well Enough?

Writing to potential employer

Forget about the template tricks. It doesn’t work here. Pain letters are as unique as the business themselves.

Set aside enough time to learn as much as you can about your potential employer. That’s not negotiable by the way. Know their history, what they do, who they serve, and imagine what sort of challenges they could be facing and what solutions (if any) you have in place for that, and so on.

Who Has Problems I Can Solve?

Business pains! Lots of businesses have them, and they are as varied and diverse as the businesses themselves. Now, of the potential employers you plan to reach out to, figure out who seems to have the business pain you can solve well.

Let’s assume you are a digital marketing specialist. A business that’s trying hard to crack the digital space could be your best target.

Search online platforms for their presence. Evaluate their performances. Identify the gaps in their strategies, particularly those eating into their performance. Make a list, then reach out with the solutions.

Have I Shown Them My Value?  

Ask yourself, “What issues can my skills solve?” For instance, as a digital marketing specialist, your skills could be helpful to a business that’s trying to turn itself into a brand, find a target market online, or turn around their struggling marketing campaigns on social media.

But that’s not all a terrific digital marketing specialist could do. Think of brand awareness, search engine optimization, keeping up to date with new trends in tech, etc. Elsewhere, these could be business pains.

Now, when you pen down that writing letter, don’t dwell on your skills. Instead, let your potential employer know that you recognize their pains and want to solve them.

The Three Major Steps To Writing A Perfect Pain Letter

Before doing anything else, first, get the name of the person you’ll be sending the letter to. Usually, that could be the Human Resource (HR) director or the Chief Marketing Officer (CFO) – for the positioned mentioned earlier.

Keep off those in higher positions, like the company CEO, unless it’s a small business or you are going after the same job.

CEOs tend to have thorough personal assistants who filter out what gets to their desk. That pain letter has a greater chance of landing back to the bin of “less important matters” and may never be retrieved again.

That said, here are the steps on how to write a pain point letter for a job.

Step 1: The Introduction


First impressions actually matters. Your intro will be you meeting your potential employer for the first time. What you want at this point is to pique their interest and attention, and here’s how to do that.

Start off your letter with a news item, event, or activity from the past that involves the company. It could be a new technology they adopted, a feat, awards they have won, something interesting the CEO said at a major event.

Acknowledge and express approval of it.  Here’s an example of a hook:

Dear Gareth,

I recently learned of your recognition by Forbes as the Next Billion-Dollar Startup in 2019, and I agree that is a well-deserved feat, given your consistent stellar performance in mobile app development. Hats off to you and your team for showing the rest of the startups that it can be done.

Step 2: The Body

Have your catchy intro lead into the pain point. Think of those things keeping the CFO or CEO hot and bothered. That list may be long, but one pain point is enough since you want your message to be less sentimental.

Don’t wade into the pain point in your pain letter; point it out and hold your peace. Here’s an example:

With your newly found status, there must be so many eyes set on you now, and I can imagine how managing your brand online presents new challenges. Every decision carries more weight than before and has to be well thought-out.

Then follow this up with a dragon-slaying narrative. Make it about that sigh of relief your boss or team breathed when you hacked a similar pain. It could be something like this:

Not too long ago, when I ran digital marketing operations for Bluebox Solutions, I oversaw the growth of its digital platforms from hundreds to millions of users. As the brand and company status grew, I worked alongside the executives in seeing to it that their stellar performance online remained consistent and only changed for the better.

Step 3: The Conclusion

Make your last words short and punchy – one or two sentences should be enough. It could sound this way:

If you plan to maintain your brand consistency and award-winning performance or refine the digital training programs for your employees, I’d love to discuss these further when it’s convenient. Good Luck.

Drew Sturrock

One more thing: Be brief as you can. Studies say the average attention span for adults is now way shorter than that of a goldfish. A recruiter could toss way your pain letter after 5 seconds if all you are talking about is yourself. Resist this urge completely.

Final Thoughts

Let’s face it. The old world as we knew it is gone. Recruiters see things differently now. Jobs have evolved. Technology is here with us, determined to disrupt everything on its way. Not doing anything about this will be the beginning of your severe woes. Act now! Hunt that job in a new way. Walk this new path and explore its many potentials.