Select Page

Somewhere in a big office, there is a senior executive with meetings lined up, a full agenda and at least 5 new emails in their inbox. If you want to get this person’s attention, you need to stand out.

One way to do this is by sending a pain letter.

Writing a Pain Letter

When done properly, a pain letter can be an effective way to get your foot in the door with an executive. Traditionally, a pain letter would be delivered by snail mail. However, that isn’t always the case today.

Millennials and Gen Z overwhelmingly rely on digital communications. Because executives now span 3 different generations, delivering a pain letter through email or social media (such as a LinkedIn message) is also an option. In fact, it wouldn’t hurt to follow up with a phone call, message or email if you send the original letter via mail. This is especially true if the executive hasn’t replied to your pain letter within a week or so.

The goal is to make a manager stop what they’re doing for a few minutes to read your letter. If what you write piques their interest, it could be the window to great opportunities.

  1. To start, you address the recipient properly, then congratulate them on a recent company accomplishment. This shows that you’ve kept up with their news and appreciate the work they do.
  2. Next is where you work in your “pain hypothesis,” something within the company that could use improvement, therefore a pain point for a company’s executive team. This part takes a great deal of research. If your pain point isn’t relevant, they’ll assume you don’t understand the company at all.
  3. If you’ve tackled a similar problem in your career, briefly explain it. Use statistics, if possible.
  4. The letter should always end with a call to action, such as asking the manager to schedule a phone call or chat via email.
  5. Be sure to include your name and contact information, as well.

If you can’t find a blatant “pain point,” you still have options. For example, do you see a huge opportunity for the company that they aren’t taking advantage of?

Depending on the medium you use to send your pain letter, you could also possibly attach your resume, essentially making the pain letter the equivalent of a cover letter.

The letter works by forcing executives to see you as a problem solver, not just a job seeker. There is a chance your pain letter won’t be effective, but there’s also the chance that you’ll receive a phone call or email.

When to Send a Pain Letter

Because it is such a time investment requiring much research, you want to reserve pain letters for strategic use, such as when you are targeting a handful of companies for a “dream job.” Sending a plethora of poorly written pain letters won’t get you anywhere.

Sending a pain letter is a very specific tactic, but it is useful for getting you in the right mindset. It puts you in a position to think like the executive so you can highlight the things they actually care about.

Pitfalls of Pain Letters

Although pain letters have their benefits, sending a poorly executed pain letter could be worse than sending nothing at all.

I recommend that you avoid sending a pain letter if you’re not an expert in the topic you’re suggesting to an executive. The point is to provide a solution or provide the executive with ground-breaking research they may otherwise not know about. If you’re not adding value to the conversation, you’re just wasting everyone’s time.

You should also be conscious of the letter content itself, including your focal point. If the issue you’re addressing is too broad, it won’t have the power you’re aiming for. Your tone is another incredibly vital part of the letter. If you come across as arrogant or “salesy,” the executive could react unfavorably. If there are any typos in the letter, that is a red flag for any executives who appreciate attention to detail and professionalism.

Here are a couple disaster stories of poorly-written pain letters:

“I get versions of these regularly from cold-calling vendors and occasionally from job applicants, and they are always–*without exception*–based on incorrect and unsubstantiated assumptions of the job position/our company/the industry. They basically telegraph I AM CLUELESS AND DIDN’T DO MY RESEARCH and they are processed accordingly.”

“I think they might have a place, but only if you already work for/with the organization and are keenly aware first-hand of a particular problem… I’m aware of a couple of positions that were created based off someone saying, ‘Look, XYZ is a disaster, here are my ideas to fix it, please put me in charge of doing that.’”

When thinking of writing a pain letter, proceed with caution, but don’t let the potential pitfalls scare you away. Any busy executive aims to have employees that solve problems effectively. If you have the experience to prove that you’re an asset to the management team, don’t sit on that information. Make it known.