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Cover letter workshop - WITness Success / Minnebar

23 Jul 2022 🔖 professional development salesforce
💬 EN

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Table of Contents

Below are notes from the cover letter workshop at the July 2022 WITness Success Salesforce community conference and the June 2022 Minnebar un-conference.

Love to protect voting rights in rural America?

Donate to fellow WITness Success speaker Cece Adams today!! Can the Salesforce Ohana help her reach her goal? I think so!!

Cece is running for a small, “down-ballot” local office in northern Illinois that has a big impact on access to the ballot box. She’s also prioritizing fully funding her local schools, building out workforce development programs, providing wage supports for essential workers caring for our elders, fixing roads, and encouraging public health.

Every $10 or so is another lawn sign she can get into a supporter’s yard!

(She didn’t ask me to do this, I just met her at the conference and think she’s really awesome.)


You’re already awesome – and sometimes that’s easier to realize when you tell someone else. Add some bedazzling with words and you’ll positively glitter.

Cover letters provide a special opportunity to feed two birds with one scone – in convincing someone else how qualified you are, you also convince yourself.

Bring a job posting that feels like a stretch and a willingness to share your transferable skills aloud.

We’ll do as many “cover letter makeovers” as we can, helping participants see their beautiful selves in the mirror of everyone else’s eyes.

We’ll rewrite insecurities like…

“I don’t know what I’ve done – most of my career has been in retail, folding shirts and standing at a cash register.”

…into power paragraphs like…

“Eight years of satisfying clients with tight turnaround times has taught me that process is important, but people are everything. I’m always organizing systems and documenting technology to make sure my ducks are in a row for busy seasons. But the secret sauce to staying on top of everything has been my communication skills – I take pride in my ability to ensure that anyone seeking help from me feels valuable and trusts that I see their needs.”

You’ve got this! I can’t wait for you to see just how much.

Notes from WITness Success version

Firstly, I’d like to thank every participant who took “collaborative workshop” seriously and served as impromptu guest panelists. Here are some fantastic ways everyone made this workshop delightful:

  • A participant already doing architectural work is aiming for an official “Salesforce Technical Architect” job title. She volunteered to let us work on writing her next cover letter together.
  • A participant pretty much photographically memorized the random “Salesforce Technical Architect” listing we pulled up on Indeed, always asking things like, “Scroll back up, what about that sentence that mentioned mentoring?”
  • After participants who are senior hiring managers and recruiters elaborated on the importance of tying one’s skillset to business value, all participants jumped on our volunteer with “Why?” questions that could make a toddler jealous. See “writing prep” below.

Very quickly, I felt like I was “mic tech” for a Circles of Success, not “presenter.” The experts were out in the room, and they were quite confident shining and sharing!

Far be it from me to get in the way, right?

My only regret, as “presenter,” is that I spent the last 60 seconds of the meeting writing instead of thanking you all for the ways you stepped up and made this session truly special. I hope you see this now.

We spent the first half of the session talking theory, and the second half putting it into practice (writing).

I heard afterwards that one value-add of the writing improvisation was the same thing that makes live-coding / live-admin-configuration demos fun:

  • You get to watch the person deemed “expert” enough to have a microphone make mistakes.
    • You get to hear the person at the keyboard mutter, “No, wait, that reads terribly” and hit backspace and apologize for writer’s block while under pressure to perform.
    • Feeling less alone in making mistakes can make “and persists anyway in trying to fix them” feel more doable.
  • Recruiters can provide the best advice in the world (“connect your history to the business’s needs!”), but gosh darnit, “implementing good advice” is hard for everyone, even with practice. It can be reassuring to see that.

That was exactly the “good kind of messiness” that I’d hoped for. And then it reached such fantastic heights when everyone contributed their wealth of experience. THANK YOU again to all for stepping up as a collaborative roundtable. It was humbling, destabilizing, and absolutely terrific!


Slides (PDF)

There weren’t many slides, but I shared a few principles that help me write:

  1. “Business language” is magic. It turns insecurities into strengths & strengths into superpowers. It’s practiceable, too.
  2. Let friends help you write, and if you ever get to be on a hiring committee, do it – you get to see great writers’ cover letters. Everyone learns new skills through help & imitation. Copy-paste-edit from templates & friends’ help, just reflect on why it felt useful so that you learn.
  3. Including words from the job description can be surprisingly effective. Hiring managers are busy, tired people. Not only is mirroring a classic sales technique to build rapport, but when you save hiring committee members’ time by “reading their minds,” you build trust that you’re the kind of person who will be in touch with their needs and save them time once you’re hired.
  4. Be concise.
  5. Never use jargon – that’s for your resume. If you must highlight a strength like “Flow” because it’d make you a rockstar for the job, address the business value: “…building time-saving data entry interfaces for sales staff with Salesforce Flow…”
  6. Cover letters are like getting to impress people with a great answer to “So why did you apply for this job?” even when they haven’t invited you for an interview yet. They’re like a sneak-attack interview that you invite yourself to.
  7. Writer’s block? Ask yourself, “What makes you feel like a superhero?”
  8. Feeling too unconfident to answer that last question? Try this one: “What do you love about what you do?”
  9. Answer the last 2 questions out loud to a friend and have them take notes. They’ll probably only write down the good stuff, not all the fears & insecurities, and you’ll be amazed how awesome you are when you hear what they wrote down.


Powerful tips shared by session participants:

  • Describe your problem-solving skills. Don’t just say “Apex”. “I provided value” gets skipped sometimes, and it shouldn’t be.
  • Can you measure your problem-solving skill stories? Is there a number like “90%” or “10 times” that you can work into the story?
  • Annotate advertisements with “+” and “-“ or highlight in green / yellow / orange to indicate your confidence in each bit of the advertisement you read. Particularly add up the +’s / greens to give yourself confidence to apply.
    • Then, for each “+” / “green”, ask yourself, “So what?” By yourself, or with a partner asking you that, force yourself to articulate the “business solve” of each strength or accomplishment.
  • Cover letters show personality.
  • Work with a partner, or a few. (A comment from this session: “Why don’t we always do this in groups?!”) People can’t read the self-deprecation & fear & hesitancy in your mind, so what you get reflected back to you by working with a friend is the best parts of yourself.
    • (Note: Yes, feel free to do this in a Circle of Success or a User Group!)
  • Be explicit about how the job description has to do with you.
    • Especially if you are transferring skills.
  • Advice aimed at university admissions essays is very transferable to job searches, because it’s about selling your story.
  • Practice skills from your goal-job at your current job. (In this case, practice talking to your constituents about value.)
    • (Came from volunteer’s note that not having a background in “pre-sales” made it harder to articulate tentative value during architect interviews.)

Writing prep

Volunteer’s architect skills:

  • “I nailed the (architect role) technical (interview portions) so hard.”
  • Discovery to build pipelines & quality gates
  • Scale to a whole business / multiple businesses – “I’ve touched (almost) every cloud.”
  • “I often fix others’ stuff and teach them”

Questions that arose from fellow participants:

  • Q: "What's a pipeline? Biz value?"
  • A: "Development pipeline" (Sandboxes -> QA)
    • Q: "Oh, a development lifecycle! Cool. But ... Biz value?"
    • A: "Keep bad code out of prod"
      • Q: "What's bad code?"
      • A: "Outage / sales/service affected"
        • Q: "So what?"
        • A: "Revenue affected"
        • A: "Gartner Research has a $/hour for this you can cite by biz size"
  • Q: "What's a quality gate? Biz value?"
  • A: "Setting quality standards for technical design & and making sure they're being met. e.g. Pull request processes, did you follow code structure standards, did tests actually pass, etc."
    • Q: "Biz impact?"
    • Participant suggestion: "None, because I prevent things going down?" ;) ;) ;)
    • A: Hard to articulate the business impact of quality work, because I move on to new customers.
      • Q: "Do old clients ever call you for support?"
      • A: "No."
      • Participant suggestion: "I maintain consistency / do such good work that there's no 'second touch' / they don't reach back out to me."
  • Q: I saw "mentoring" in the job requirements. Let's make sure to throw in your training experience when we write?

Writing snippets

  • “Big data means big mistakes – so companies need the sharpest mind in the business for quality.”
    • (Struck out – never came up with a followup sentence about the volunteer that matched the bravado of that opening. Improv = mistakes!)
  • “When I’m doing my job excellently, you’ll never know I was there.”
    • (Credit: participant contribution)
    • (Participant followup contribution: Maybe start more powerfully – “I do my job excellently…“)
    • “I’m the best ghost you could ever have haunt your team.”
      • (Struck out as a followup sentence – too casual. Improv = mistakes!)
  • “An enthusiastic people-person with a sharp technical mind and deep architectural expertise, I unify quality standards across the organisation and break down silos to ensure successful cost-effective project execution on every critical mission.”

Note: I’m not crazy about this sentence, but I want to point out its structure:

  • Candidate strength (“people”)
  • Candidate strength (“technically sharp”)
  • Candidate experience (“architecture”)
  • Candidate business contribution (“unify quality standards”)
  • Language-mirroring from the advertisement (“across the organization” – ad’s 1st bullet said, “Manage and implement the technical architectural blueprint, coding standards, leveraging the IT capabilities across the organisation.”)
  • Redundant rephrasing of the language-mirroring to make it feel less copy-paste (“break down silos”)
  • Business impact + language-mirroring from the advertisement (ad’s 2nd bullet said, “Liaise with key stakeholders to determine and prioritise business requirements, transforming business requirements in technical requirements, and working with cross functional teams to ensure successful cost-effective project execution“)
  • Redundant rephrasing of the language-mirroring to make it feel less copy-paste (“on every critical mission”)

Do your paragraphs have to be composed this way? No! Does it always make for engaging, expressive writing? Also no! But when you have writer’s block, mixing and matching phrases from the advertisement with your own words can be a nice way to give yourself a template to start writing something onto the page that connects you to the job description and to the business’s needs.

  • [insert quote from ex-boss or recommendation]
    • (Credit: participant contribution)
    • Volunteer: “A friend said: ‘Just hire her already’”
    • Participant suggestion: Ask friends to write you notes or LinkedIn recommendations so you have a nice big quote-bank.
  • “Give me the opportunity to show you how passionate I am about [technical] architecture “
    • Participant contribution
  • “Mentorship is my passion. When junior members of staff thrive, the business thrives. Through my work and the Intro to Salesforce course I teach, I have empowered others inside and outside of my organization. I would love the opportunity to explain to you how I teach the junior staff on my practices.”
    • (Ad started, “We are looking for a Salesforce Technical Architect to drive, mentor and implement salesforce solutions across various industries and niches.” First experience bullet said, “Extensive hands-on technical consulting and solution implementation experience, including with one or more common enterprise software solutions (e.g. CRM, ERP), demonstrating positions of increasing responsibility and management/mentoring of more junior technical resources; experience with Waterfall and/or Agile implementation methodologies.”)
    • Mentioning experience by name (teaching formal courses) was a participant contribution.
    • (Credit: participant contribution for “I would love the opportunity … practices”).
    • Volunteer showed a lot of pride in work about getting an entire team on board with quality, so I thought tying in some “passion” words to “people” words (“thrive”) and “business-need” words (again, a generic “thrive” – participants probably would’ve rightly called me out on not “so-what?”-ing myself enough and being specific about a business goal met, oops!) might be a nice way to grab a reader’s attention – word choices I call “exclamation point vocabulary.”

Notes from Minnebar version

Volunteer 1

  • Disability accommodations needed
  • Diversity-embracing, non-prejudiced company needed
  • Most jobs in participant’s field are not where participant lives now


Once you see a job, Google tourist info about it and find something that seems cool to you, and leverage that to make yourself sound serious about being willing to move there:

“I’ve been a barbecue fan for years and can’t believe that such a great match for my skillset came up in Nashville. This could be a great opportunity to _____, and I’m enthusiastic to make such a move.”


I’m way out of my league on this one. I don’t face a lot of prejudice.

But a project management professor once told me that he favors leading with your perceived vulnerabilities and making it obvious how people can help you – that in his experience, more people want to help you than hurt you when you expose your vulnerabilities.

His favorite example was telling the story of how one time, he invited a presenter to speak in an environment that she perceived to be potentially biased, and she said to him, “Let me check with Jane – Jane’s my partner – about whether we’re going to be in town that week” to make it clear that she was a lesbian, and to give him a chance to wiggle out of the invitation right away if he sensed that he couldn’t ensure her a good experience speaking in his environment.

I CANNOT tell you whether to be out or in the closet about a vulnerability. I’m not even close to qualified to help you make that safety decision.

But if you do decide to be out, I think that a cover letter can be a great place to lead with strong “take me as I am or go away” energy.

So, for example, you could dig through the company’s tweets during Black History Month or Pride Month, or dig through their published platitudes about diversity in their mission statement or on their HR web page, and find some words to fire back at them and basically scream, “WALK AWAY AND DON’T WASTE OUR TIME IF YOU DON’T MEAN THIS.”

“‘Blah blah blah thing that the company said and hopefully meant blah blah blah’ – this is exactly the kind of company culture I’m thrilled to be a part of and carry forward with my technical and personal leadership.”


I’ve often found that U.S.-based F-1 international students struggle to find a company that will hire them under OPT, because those companies know they don’t “sponsor” people for H1-B visas (due to legal costs, etc.), and that’s literally all a given hiring manager has ever heard. The hiring manager has no idea that OPT can be up to 2.5 years of free-of-charge work permission … which is longer than a lot of U.S. citizens stay at their first job, anyway!

I suggest using a cover letter to educate and to correct misunderstandings, right in the first sentence/paragraph. For an international student, that might be something like:

“I am looking forward to putting the 2.5 years of employment authorization (at no cost to the employer, with almost nonexistent paperwork!) that graduating from a U.S. university entitles me to into service of a company that rescues lost dogs. As a former teenage dog trainer, programming your web site is a dream come true.”

Volunteer 2

  • American Sign Language (“ASL”) interpreter.
  • People always find that interesting but have no idea what that means they did.
  • It’s tough to quickly summarize the huge range of things done in 6 years.
  • Currently learning coding adequate to apply to junior software developer jobs.

I Googled “junior developer jobs” and clicked the second one that showed up. A “benefit” in the listing was, “chance to talk about sports daily” (it was for a sports-related company).

  • “Actually, I talk about sports daily!” the interpreter beamed.

PERFECT – we can run with that.

Don’t boil the ocean

  • Don’t try to summarize all transferable skills gained in 6 years.
  • Let some of the skills be pleasant surprises making you a rockstar your new colleagues love, and that you get to tell stories about picking up as in interpreter.
  • For a cover letter, pick one or two transferable skills that seem relevant to any given job listing.

Sports = ASL = teamwork

Here’s an example of picking just one aspect of the interpreting background and pairing it with the the sports job description:

“I do talk about sports every day – and I can communicate it to a diverse range of people, to boot! ASL interpreting isn’t just about bridging communications gaps between signers and vocal speakers. The subject matter is infinitely varied in context and sensitivity as well – everything from artistic expression at the theater, to life-critical issues at the hospital, to putting things in words that small children can understand at school. I bring comfort and confidence to people all throughout a collaborative process, and it shows in the teamwork I do to bring great software products to market.”

Instant accessibility experience

A hiring manager from the State of Minnesota who was in the audience pointed out that normally, the value of always thinking of accessibility has to be continuously trained into people whose only career experience is in software development.

This manager thought our interpreter would instantly be recognized as bringing things to the table that are needed at the state as they focus on refactoring for accessibility and building accessibility into more projects from the get-go, and encouraged the interpreter to put their “accessibility” foot forward in cover letters.

Volunteer 3

  • Liberal arts degree
  • Customer service career history
  • Administrative assistant career history
  • Currently learning coding adequate to apply to junior software developer jobs.

Your “transferable skills” are probably a little more obvious to you than the ASL interpreter’s – people already have some preconceived notions about what great “customer service” or “administrative assistance” feels like when they’ve received it, so while you totally should pick stories from your whole career (but again, don’t boil the ocean – cherry-pick and tailor to individual job descriptions), obvious stories to fall back on are ones that play into experiences everyone assumes you delivered in those jobs:

  • Communicating calmly under pressure
  • Multi-tasking
  • Making sure people who actually have to use/do a thing feel empowered to actually use/do it
  • Teamwork

Volunteer 4

  • “I think I’m allergic to the word ‘I.’ I use so much ‘we’ language – I’m really shy about taking credit for my work when everything I’ve done has been a collaboration with other people.”

Considerate = good

Firstly, that’s fantastic. Lean into it – you can say “we” more than you say “I” as long as there’s some sort of “I” in there. It makes you look like the considerate, generous team player it sounds like you are. People are going to be excited to work with you when they see that.

Get interviewed

A fellow attendee said, “See if you can get someone to interview you and draw stories out about you, probing for details about how you personally supported some of the team successes you’re proud of being a part of.

Great idea!

Grab a friend and ask them to be both interviewer and notetaker (so you can just relax and answer – or get a second friend to take notes).

The wonderful thing about letting other people filter you onto paper is that they can’t hear the self-doubt in your brain. They can only hear the words that come out of your mouth. The notes they take will suprise you with how great you look, after they’ve forced you to say nice things about yourself out loud.

Two prompts I like are:

  1. Giving: What tasks and moments in your work have made you feel like a bit of a rockstar, or a superhero, or delightfully clever, or satisfactorily effective?
  2. Taking: What tasks and moments in your work have made you happy about having the job you are/were in? What kinds of things can make a day a good one?
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