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  • Robb Conlon

Adding on to your Application: Beyond Cover Letters

We all know the importance of a good cover letter.

Fill it with the right words and opportunities open up because ATS (Applicant Tracking Systems) eats keywords right up and will hopefully advance you to the next phase of the hiring process.

In the coming weeks we'll be bringing in a guest who has something incredible to add to your applications, but before we do, there's another type of add-on that's a bit more difficult to obtain unless you know the right way to go about it.


Maybe you've written one, maybe you've received one on an off chance like I have throughout my career for exceptional service to a client; or maybe you haven't ever received one and have no idea how to ask on how to get one.

We'll peel back a bit of that secret today.

First step: do a great job for someone.

It can be work, it can be volunteering, it can be cutting their grass. Depending on your career stage, any of these could be viable for you.

We'll take a recent example I had where I scored a rockin' letter of recommendation from a former manager of mine.


In late 2019 I was doing some contract work for a major HVAC company here in Wisconsin. I had a position in the internal procurement department. Basically I online shopped for powertools for air conditioning technicians all day and routed them to the right store branch to pick up.

Was I in love with the job?

To be honest, no, it wasn't really a fit and it put me back into a more front line position than I wanted to be in. There WERE however, really great colleagues that made work worthwhile to come to. (If any of you are reading this, I miss you folks!)

My supervisor at the time was a long time employee of the company named Jean.

Jean did her best to make me feel like a part of the team as a contractor and willingly gave generously of the sparse resources she had to offer to me to help me succeed.

I wanted to repay her by doing a great job at the position she had brought me in to.

A number of months passed, and I actually somewhat enjoyed the monotony of the job I was in. I mastered the processes and looked to take on a new role or at the very least new responsibilities in the upcoming year.

Well, that all went off track SUPER QUICKLY when COVID-19 became a thing.


Within 48 hours of the company announcing that it was facing tough times, my job was GONE.

So I had to act quickly to gain a benefit from my position there before I lost contact with folks. (Yes LinkedIn could have been used, but I believe asking for things like this is an in person kind of thing.)

As I was getting let go and saying my goodbyes, I asked a critical question of Jean.

"Jean, I'm sorry we had to part ways under these circumstances, can I ask you a pair of quick questions?"

This is the opener for you to start the conversation, and you need to follow the next part very carefully so you are not abusing your colleague/manager.

She replied that I could absolutely ask a quick question or two before I walked out the door.


I followed up with:

"Jean, have I done a good job for you and the department in my time here?"

This question is twofold, and what you ask next branches based on the other person's response.

Jean responded:

"Yeah. You did a great job for us, and I wish I could keep you on and I'm really sad to see you go. You'd do well in other positions here, be sure to keep an eye out for those."

This made my heart sing. And if you receive feedback like this, you've done a wonderful job.

A positive response like this, especially when parting ways, leads into the following ask; and this is where you'll find pay dirt hopefully.

I replied:

"Jean, I'm really glad I was able to make you happy and I'm sad I have to leave. Since you were happy with how I did, would you be willing to write a letter of recommendation for me to help me find a new position?"

And then you wait. Don't speak until the other person has spoken.

If you do this, you likely lose the opportunity.

(***IMPORTANT***: This is a sales technique, some people need 8 seconds or MORE to process what you've asked them and formulate an answer. Don't sink your chances of a letter by opening your mouth!)

I had an outstanding relationship with Jean and it paid off big time in a glowing recommendation letter.

Be sure to give your letter writer enough time to complete it for you; if they ask when you need it by, tell them 2-3 weeks, but if they have it done sooner, that works too.

Remember to thank your letter writer in person at the time of agreement, and via email or mail down the road when you receive the letter. (For things like this, a hand written card would go a LONG way.)


There's always a chance that you'll receive a non-affirmative to either of the above questions.

If you ask: "Have I done a good job here for you..." and the answer is anything less than GREAT, you need to stop the process.

Your goal is to grow your career and yourself from this interaction not make a fool of yourself. Have the following question ready for responses that aren't sunshine and rainbows.

"[Name], I was hoping to hear that I had done a great job, but it sounds like I wasn't doing so, could you give me a few areas that I can improve on for my next employer that prevented me from being a great employee to you?"

Be willing to listen and take things to heart, feedback is tough to receive.

If the second question is met with a "No, I won't/can't/dont want to/ am too busy to etc.", don't worry, you still have an easy out, regardless of the reasoning your colleague has given.

"[Name] I appreciate you letting me ask. I understand that putting your name on a document about me is a big thing, and I thank you for entertaining the idea."

And then drop it.

Pay your thanks to them for the prior opportunities to work with them, and as you're being walked out of the building, be the best person you can to all your old co-workers, you never know when one of them might have an opportunity for you.


This whole article is my personal experience, but I've found it a useful template in asking for a lot of things professionally, including ways to build this show bigger.

I hope that the knowledge and template presented here help you in getting a great Letter of Recommendation.

Success stories? Share them with us at


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