5 questions to ask yourself before you ask someone to write you a letter of recommendation

most of us have written or requested a letter of recommendation before. for some, this started when we were applying to college. for others, your experience with recommendation letters began when you were trying to get a job. or applying for an award. or seeking membership into an organization. or trying to get out of trouble. or getting a new place. or joining a board of directors. the list could go on and on. 

the point is that recommendation letters have many uses. and a lot of times, they can be just the thing that sets you apart from other candidates. but they have to be executed correctly. 

i’ve noticed a lot of professionals, young and old, are going about recommendation letters all wrong. and in some of those cases, their negligence or ill-preparedness has prevented them from getting that job, apartment, or scholarship. 

and don’t get me wrong, you can still have an amazing recommendation letter and not get selected for reasons beyond your control. but the recommendation letter is within your control. and it all starts with who you choose to write it.

here’s a list of questions you should ask yourself before you request a recommendation letter from someone. because a lot of ya’ll out here tweaking, low key.

5). What is my relationship with the person I want to write my recommendation?

is this a former teacher? coworker? manager? mentor? basically, how do you know this person? and is the capacity in which you know them appropriate for writing you a letter of recommendation? you need to be able to answer this question before you reach out. don’t pick someone solely because they’re “accomplished.” because that same person could have literally no investment in you as a person and could care less whether you win or lose at life. and that brings me to my next point…

4). Why is this particular person best suited to recommend me?

you can’t be out here asking anyone for a recommendation letter because you think ya’ll cool. is this person relevant to the purpose you need the recommendation letter in the first place? as in, can they speak to the skills and qualifications necessary for the organization, award, or job you’re applying to? generally speaking, a former teacher would be better suited than a current coworker if you’re applying to grad school. and a previous landlord may be more beneficial than a former teacher if you’re trying to land a new apartment. it really just all depends on why you need the letter.

and if you do nothing else, make sure this person can actually put a nice letter together. the worse thing you can do is have someone speak about your character and capability when they’re incapable of proofreading their letter before submitting it. tacky. 

3). How can I make the process of recommending me easy for them?

a recommendation letter isn’t something you [should] throw together. and for some, it can be a little stressful trying to collect their thoughts and write a succinct letter that outlines your relevant traits. you can help mitigate this by making the process of recommending you as seamless as possible. this means you will give them as much advance notice as possible about your desire to have them write you a letter, you will remind them periodically about your letter (if the time between when you requested it and when you need it is significant), you will give them all context for the letter in the upfront (like what is it for, when is it due, who it needs to be addressed to and where it needs to be sent), and you will include your resume for them. and speaking of which, another question you need to ask yourself is…

2). Have I updated my resume?

assuming that the person you asked to write your letter of recommendation agrees to do so, one of the first things they’ll ask for is your resume. and at that point we know that you don’t follow instructions because the aforementioned point indicated you should have already sent them your resume. don’t be that person. 

resumes are a great point of reference for who you are, professionally speaking. and they show the recommender the traits and skills you value about yourself, which can help them to embellish your letter and ensure that it’s consistent with information you’ve already shared. because the goal should always be to present you in the best possible light, ya know?

1). Am I qualified for what I’m applying to?

i’m all for speaking things as though they were and going after what you feel you deserve in life. really, I am. but we also have to be practical here. don’t be out here wasting people’s time. you do a disservice to both yourself and the person you want to recommend you when you ask them to recommend you for a job, award or organization that is beyond the scope of what you’re able to do, the work you’ve done or the person you are.