Want the Attention of C-Level Executives? Try This.

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.

(Originally published on my blog page at clarelemortimer.com.)


Using Communication to Influence and Inspire

When you speak, do you just want to be heard, or do you actually want to influence others? Communication is a basic component of our everyday lives. However, some people simply communicate better than others. This goes beyond just grammar and knowledge; it’s something deeper.

Learning to communicate effectively can impact every aspect of life, including social status. One basic human instinct is to strive for inclusion and acceptance. We also have a natural desire to increase our social status, thus being a influential members of our companies, industries, and society as a whole.

Language and communication are more complicated than meets the eye. When we speak or otherwise relay a message, people’s brains are left to process that information. We can somewhat influence how that information is perceived based on how we present it.

Communicating Your “Why”

Great leaders have a unique way of thinking, acting and communicating. Simon Sinek calls this the “Golden Circle.” Most everyone knows what they do and how they do it, but influential leaders instead focus on something else: Why they do what they do. From Apple to the Wright Brothers, the most inspirational leaders start with the “why.” The “what” and “how” of their message and actions are secondary to their motivation.

For example, did you notice my introduction? I didn’t simply state a summary of my main points like someone would do for a news article or college paper. I told you why you should care about this aspect of communication. That’s the difference. It’s not about the straight facts. It’s about presenting those facts in a way that resonates with your audience.

The average person will care more about numbers and statistics if they’re first inspired by something related to those facts. Whether we like it or not, sometimes our gut feeling overpowers rational thought. If we’re choosing between two very similar products at similar prices, the differentiating factor will be something we can’t explain. It’s the “why.” We’re drawn to people and companies who value the same things we do. Because of the way our brain’s limbic system is wired, our feelings of trust and loyalty drive behavior more than facts and figures do.

Using Communication to Advance Your Career

A company’s employees don’t stay for the paycheck. They stay because it feels right; there is a sense of community. Similarly, there’s a reason for in-person interviews during the hiring process. Sometimes even the best candidate on paper can be overlooked if another candidate makes a better case for why they believe they’re best for the company or organization.

The way we speak and present ourselves can impact our careers when interviewing, trying to get clients, seeking information, applying for promotion, etc. This is why communication has such a powerful effect on every aspect of our lives.

Beyond Business

Communication is vital for business, but it’s also an intrinsic part of our world as a whole.

One of the most influential leaders in history was Martin Luther King, Jr. He wasn’t the only civil rights activist of his time, but he became the most well-known because of how he inspired others. He didn’t just talk about his concrete plan for creating sustainable racial equality. He told people what he believed — what he dreamed of. His audience was comprised of people who held similar beliefs, regardless of skin color or heritage. They used his influence to make his mission their own.

Effective communication leads to higher social status, which can change lives around the world. A  case in Bangladesh indicated that a woman rising in social status can bring down rates of domestic violence. Increased status wasn’t achieved by simply giving resources to the women. It was done through communication. Women who developed social ties and confidence increased their status in society, leading to a significant decline in spousal abuse.

When trying to be an influential, inspired leader in our own lives, we can look to other leaders and adopt their best practices. We can learn to communicate our message in a way that makes people stop and genuinely listen. You never know what your influence may inspire.


Originally published on my professional website blog at clarelemortimer.com.

Networking and Communicating Effectively

In the professional realm, networking has become an inevitable necessity. The truth is, most people aren’t networking in the most efficient way possible.

Idea Networking

In William Duggan’s book, The Seventh Sense, he outlines the strategy for “idea networking.” This isn’t simply meeting dozens of people and hoping a few conversations pan out.

With idea networking, you target one specific influential person in your field. Contact the person through phone, email, or in person. You want to avoid talking about yourself and what you’re looking for (a new job, etc.). Instead, you want to focus on a specific idea.

Is there something in your field that especially excites you? Formulate an intriguing question around that topic. You want the question to be specific enough that an expert in your industry would be interested in the conversation, yet general enough that there’s room for the conversation to take different directions.

When you get a chance to connect with one influential person in your field, it can open doors for future meetings. Duggan recommends ending the conversation by asking for a few other people who would be interested in discussing your question. From there, you repeat the cycle.


Your experience and professional skills are important assets, but your ideas and ability to communicate speak volumes about you as an asset in the workplace. To put your best foot forward, you need to communicate effectively.

NPR host Terry Gross offers some great communication advice. Although her on-air interviews may be different than conversations you’ll have with your professional connections, the tips translate well.

Firstly, “Tell me about yourself,” is the best icebreaker….

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