How To Hone An Executive Pain Letter Which Secures Interviews

Finding your next executive tenure can feel challenging at the best of times. You’ve heard it’s a ‘candidates market’, but it certainly doesn’t feel that way. You attend networking events, apply to jobs and send your personalised cover letter and CV to prospective employers, seemingly to no avail.

The truth is, it can be hard to stand out. You have the skills and expertise in abundance, but your job applications, cover letter and CV don’t get traction. Could it be because everyone’s doing the same thing? Tailored cover letters and CV’s are prerequisites these days, not the gold standard.

For executive roles, the vast majority of which go unadvertised, a pain letter could be your foot in the door. Here’s how to hone an executive pain letter.

What is an executive pain letter

Think of an executive pain letter as a cover letter with bite. First coined by Liz Ryan in 2013 (author, CEO of Human Workplace and former Fortune 500 HR SVP), pain letters have been causing a stir ever since, transforming the mundane cover letter into a purposeful statement of intent.

Whereas the cover letter generally amplifies the skills, experience and accomplishments on your CV, the pain letter put’s these into context in a compelling narrative. It identifies the hypothetical problem the hiring manager faces, and positions you as the solution, demonstrating your functional expertise and business acumen in the process. In short, it’s all about them – the hiring manager and his/her function – not you.

A well-honed pain letter helps you stand out from the myriad of applications and cover letters the hiring manager might receive. It grabs the Hiring Managers attention, demonstrates your understanding of their problem(s), and entices them to take action, whether a callback or shortlist for interview.

1) When you can identify the hiring manager

Executive pain letters work best when addressed to the hiring manager – your prospective boss and the individual with the highest authority (and stakes) in the hiring process. You want your pain letter to resonate with this individual and encourage them to take action. However, should your pain letter end up in the in-tray of another member of the hiring team, it is unlikely to have the same impact. If you can’t identify the hiring manager, consider sending a traditional cover letter. This will likely be better received by a member of Talent Acquisition (TA) or Human Resources (HR).

2) In conjunction with a targeted outreach campaign

Highly-targeted outreach campaigns and executive pain letters go hand-in-hand. In qualifying companies that made your shortlist, you would have researched their mission, values, offerings and achievements. Combined with your functional expertise, you should now be in a position to hypothesise as to the problem causing the hiring manager sleepless nights. However, if you are casting your net wide, it does not make sense to invest this level of time and effort. Send a tried-and-true cover letter rather than risk making an uninformed assumption as to the hiring manager’s pain.

3) When there is no job description

Executive pain letters deliver in the absence of a job description. Focused on the hiring manager’s pain, they demonstrating your problem-solving ability, functional expertise and commercial acumen. You are effectively pitching in a consultancy capacity, identifying a problem and proposing a solution (you). In contrast, cover letters are all about you. Without a job description with which to align your skills and accomplishments, you are effectively pitching blind. You have to hope the hiring manager is acutely aware of their pain and needs someone like you to resolve it.

3 must-haves for a successful executive pain letter

1) Hiring manager name and contact details

As mentioned previously, executive pain letters work best when addressed to the hiring manager. If you can’t identify the hiring manager, send a traditional cover letter and address it to HR.

As a bare minimum, you will need to know the hiring manager’s name, title and email address. Ideally, you will supplement this information with their LinkedIn profile, contact telephone number and postal address too. This is so you have the option to send your pain letter by post, and can follow up with the hiring manager several days later by telephone, email or LinkedIn InMail.

You can find prospective hiring managers on LinkedIn, the company’s website, publications (e.g. annual report, brochures, case studies, etc.) and they are sometimes named in job descriptions.

2) A viable pain hypothesis

An executive pain letter is nothing without a viable pain hypothesis. This is the hypothetical problem vexing the hiring manager; the problem you will solve by joining their team.

To discover the hiring manager’s pain, you’ll have to turn detective. Start with the job description or job advert, if available. Look at the bigger picture; why does the hiring manager need to employ someone to oversee the various responsibilities? What are they looking to achieve, and crucially, what problems is the hiring manager hoping to alleviate with this appointment?

Next, turn your attention to the company itself. You need to understand the company’s vision, mission and values, its past, present and future ambitions. Read annual reports, accounts, investor information, press releases, career pages, product/solution pages, blogs and social media posts to get a sense of how the company positions itself in the market. Now, compare this with how the company is depicted in industry publications, news articles, third-party blogs and even reviews left by current and former employees on sites like Glassdoor. Do the two align?

Finally, consider reaching out to your extended network to see whether anyone has an affiliation with the organisation. Could they put you in touch with a current or former employee who could give you the lowdown on the organisational landscape, or better still, a referral? Just be sure to reach out confidentially. Chances are you don’t want your job search to be widely publicised.

With this information, you can pen a viable pain hypothesis which will form the very foundation of your pain letter. More on how to structure and write you pain letter in the following paragraphs.

3) A CV tailored to your pain letter

Ensure that your CV reinforces the topics you broached in your executive pain letter. Your CV summary, placed near the top of your CV, should be written in a similar tone to that of your pain letter. It serves as your sales pitch, highlighting your relevant achievements and experience while providing further insight into your problem-solving capabilities in your area of expertise.

You CV should be sent as an attachment alongside your pain letter, or better still, printed and popped in an envelope accompanying your executive pain letter.

How to structure your executive pain letter

Time to put pen to paper. Ensure your executive pain letter contains these five essential sections:

1) Hook

Your hook is designed to grab the hiring managers attention and encourage them to continue reading. It is a timely (< 6 months old) event or accomplishment relating to the organisation or hiring manager. Ideally, it’s an outcome which you suspect the hiring manager may have had a hand in delivering, for example, a successful medical trial or the launch of a new product or service. Better still, it could be a personal achievement, for example, the publication of a new research paper or being invited to speak at an event. If you cannot find a suitable hook, forfeit this section.

2) Pain Hypothesis

Next, introduce your pain hypothesis, but do so with caution. Unless you have it on good authority (press releases, industry publications or trusted members of your network), you should not assume for certain this is your hiring managers pain. Doing so can give the impression of overconfidence, or worse, incompetence. Word it in such a way that you are suggesting, not asserting, and keep the evaluation high-level; this is not an exercise in demonstrating your investigative skills. You want the hiring manager to focus on their pain, not how you became privy to the information.

3) Story

This is where you elaborate on how you’ve successfully resolved a similar pain previously, supported by tangible results. You can afford to sound more confident here, but don’t brag. Use it as the bridge to introduce related experience and accomplishments which further cement you as a though-leader in the field. If you have a job description to hand, consider the use of bullet points to showcase how your wider experience and transferable skills align. Though not directly related to the hiring manager’s pain, they will strengthen the business case for your consideration.

4) Pre-close

The pre-close is your opportunity to reinstate your intention to resolve the hiring managers pain by bringing your wealth of skills and experience, not to mention your emotional intelligence, to the team. It encapsulates what you can do for his or her function or department, and that of the boarder organisation, given the opportunity. It is also the opportune moment to reflect on why you are interested in helping this company specifically, whether because of it’s mission and values, its product portfolio, company culture or reputation in the marketplace.

5) Close

Bring your executive pain letter to a close with a call-to-action (CTA) informing the hiring manager what you would like them to do next. Ideally, this will be some form of a direct response, for example, continued dialogue by telephone or email to discuss the resolution of the hiring managers pain, or perhaps consideration for shortlist for a role the hiring manager is advertising.

One final consideration: email Vs snail mail

We’ve covered what an executive pain letter is and how to go about researching and writing it, but how should you send it? You’ve got two choices: email or snail (postal) mail.

Sending via email

Emails are quick and easy to send providing you have the hiring manager’s email address. You can track when they’ve been opened (though read-receipts can be infuriating) and easily send a follow-up. However, emails are two-a-penny and frequently overused medium; the hiring manager is probably inundated by emails, and that’s if your email even makes it past their SPAM filter.

Sending via snail (postal) mail

Sending physical mail might seem dated, but it gets results. In comparison to opening an email, opening mail is an event in itself. And if it is a handwritten note, the event is even more memorable (providing it is legible and spell checked). You can track it with recorded delivery too. Providing you have the company address, the only downside is the postage costs and delivery time.

Which to choose? The choice is yours, but if you really want to make an impression, put a stamp on it.

So there you have it. Remember, your pain letter won’t win you the job in its own right, but it can open the door. A door that might have remained closed should you have sent a regular cover letter.

For more job-search advice tailored to senior managers and executives in the life sciences…

• Read How to Balance Your Executive Job Search while Employed.

* Fraser Dove International is a talent consultancy operating exclusively across the life sciences industry. While our roots lie in executive search, we provide more than the traditional recruitment services. Uniquely placed within the market, we have been providing cutting-edge talent solutions and insight to organisations at all stages of their journey – from start-up to established leaders – since 2013.