when does following up with people about meetings or favors turn into being a pest?

A reader writes:

I have a question regarding two different scenarios I am dealing with that share a commonality: how often to follow up without being irritating.

The first scenario involves a company that I have been in touch with regarding consulting opportunities. This company does consulting projects with other companies in my industry, and my expertise would be beneficial to them. The company is run by “Tom,” who is a former colleague and friend of “Mary,” who is my best friend from high school. I reached out to Tom via LinkedIn messaging in late March after being introduced by Mary. A couple of weeks later, Tom replied, apologizing for the delay in response as things had been very hectic for him lately and he was behind on emails. He was interested in speaking to me further and asked if I had time to talk later that week. Unfortunately, I never got a notification from LinkedIn that he responded, so I didn’t see his reply until a week later. I took the conversation off LinkedIn and emailed him, this time apologizing for my delay in response, and gave him some potential time blocks that week when we could do a phone call.

I have not heard from him since. A couple of weeks ago, I sent him a short follow-up email reiteating my interest in working with him and giving him a few more time blocks for a chat. Still no response. Mary says that Tom has been very busy working on a side project with his colleague “Henry” and is probably still dealing with a backlog of emails but not to give up. Since it’s been two weeks since my last follow-up email, Mary is urging me to send Tom another follow-up, but I am concerned that this will irritate him and make him less inclined to work with me. How often is too often to follow up? Should I just move on at this point? I have other projects I’m working on so I’m not pinning all my hopes on Tom’s company, but the work they do really inspires me and I don’t want to lose out on participating just because the guy is overwhelmed with emails. What do you suggest?

On a similar note, I am planning to go back to school in the fall for a master’s (in a professional program) and I need to get two recommendation letters from former colleagues/managers. One colleague already has his letter written. The other colleague has verbally agreed to give me a recommendation letter but now as my application deadline looms, she is not responding to me when I reach out to her regarding the letter. I am fairly close to this colleague – she managed me for a while and then I got promoted and we continued to collaborate together at work and have stayed in touch since I left the company – so I would hope that if she is now feeling uncomfortable giving me the recommendation for some reason, she’d tell me. But she’s not responding at all. I’ve emailed her twice (one week apart) and I left her a voicemail this past Friday. She’s approaching the busy season at her workplace so this might be a similar situation to the first where she’s just backlogged, but I don’t know if I should keep following up and risk annoying her or if I should just go to one of my backup recommenders.

In both cases, I’m dealing with people who I know are extremely busy, and when I do follow up with them I try to make it as easy as possible to respond (multiple times where it would be good to contact me back, keeping emails and voicemails clear and concise (more concise than this email to you, for sure!) so as not to waste their time). At what point does being proactive/persistent turn into being a pest?

I think you can do between two and three messages without an answer, but then you need to move on.

If someone has never written you back to express interest in whatever you’re proposing, I wouldn’t send more than two messages. But when someone has expressed interest, three can be reasonable, depending on how you frame things.

In Tom’s case, you’ve emailed him twice since his last response to you. I’d wait two weeks from the last email you sent and then send a final message that basically gives him an out while still leaving the door open if he wants it. In other words, something like this: “I just wanted to check back one final time. I know from Mary that you’re very busy so I won’t keep emailing you — but if at some point your schedule does open up and you have time to talk, I’d love to (even if it’s weeks or months down the road). I can also adjust my schedule to whatever convenient for you. Just let me know if so — and if not, I totally understand. Good luck with everything you’re working on!”

One thing I want to highlight in that language is the “I’ll meet whenever’s convenient for you” element. Offering blocks of time can be considerate by cutting down on how much back and forth is needed, but sometimes when you’re dealing with someone super busy, and they’re giving you their time as a favor, it’s easier to get it if you just let them pick the time and adjust your schedule to make it work. Obviously that’s not always possible, but if you’re offering specific times and he’s not available during any of them, you’re more likely to get a no — or in this case, silence — than if you just let him tell you a time or two that he can do it.

In the case of your former colleague who promised to write you a recommendation, you’ve emailed her twice and left a voicemail without getting any response, so at this point, you’ve hit the reasonable max of three follow-ups, and I’d assume it’s not happening and move on to a backup recommender. I think you did the appropriate amount of follow-up given that (a) she told you she would do this, (b) you know her well enough to press to a certain degree, and (c) she presumably knows that there’s a deadline. But at this point you’ve reminded her several times. She has the information, and whatever the reason for her non-response, it’s signaling to you that she’s not racing to get back to you. Since this is time-sensitive, move on to plan B.

{ 12 comments… read them below }

  1. Megs*

    I totally feel you on the late letter of recommendation thing – I delayed my law school application waiting for a letter when it would have been far wiser to have had a backup. Not that I’m ever planning on going back to school again, but if I were in any situation that needed letters, I’d absolutely lie to them about the deadline to give myself wiggle room. Even people who are the best can be the worst!

    1. Megs*

      And besides, it’s not really a lie to say “I need it by X” when the filing deadline is Y. I need it by X so I have it in advance of Y even if someone drops off the face of the planet without mentioning it to me.

    2. Kate H*

      Seriously! I applied to grad school over a year ago and one of my letters was really down to the wire. He wasn’t something I could replace either: my professor, my advisor, and head of the lab I was working in. Letters were due December 1, the week leading up was Thanksgiving break, the week before he was at a conference (along with myself and half our lab). To his credit, he got them all in on time but it was very nerve-wracking.

      Unfortunately, deadlines are basically all the same in our field so lying would probably be noticed but if I go another round I’m definitely asking they be done early.

  2. anon MBA*

    Ah, the dreaded grad school letter of recommendation. My old boss flaked out on me at the last minute, sending my blood pressure through the roof. I was able to get a hold of another old boss who said he would try to do it, but he was super busy that week. I ended up writing a letter about myself, sending it to him in a Word file, and told him he was welcome to use that if he wanted, or edit as he saw fit. I suspect he chose the former, and I’m confident that was the only way I got my recommendation in by the deadline!

    1. LD*

      This is what I was thinking to recommend. Sometimes it helps to give people a “template” to work from with the skills and behavior you think they can comment on and then let them work it into their own verbiage. Starting from scratch can be hard! So maybe the OP can send one final email with a template asking if her former manager can review that template letter of recommendation and feel free to add, delete, basically edit in any way she chooses.

      1. MissDisplaced*

        I completely agree about this! Write it yourself and send it to them, with a note that this is generally what the college is looking for, and they are welcome to change anything. It seems to help move things along.

    2. lonestarbrooklyn*

      I had to do this for a job rec from a busy friend/grad school classmate. We talked about the position on the phone, I asked her to make a few notes, sent her a thorough description of what they were looking for and how I would fit. then she made a just-barely-too-subtle hint that I should write it for her. When it was nearing deadline time and I asked her about it again she said “I’ll sign what you write.” So I had do do a last minute rec for myself, it was wierd.

  3. Scotty_Smalls*

    Somewhat related question: how long can you use a reference letter for? If I have two from 2014, could I use those or should I ask for them to updated. (I have others I can ask for letters as well.)

    1. Artemesia*

      Every reference situation I know for grad school requires the letters to be sent by the author; having one you can send yourself would not be acceptable most places.

      1. Megs*

        Even if you could send them yourself, 2014 seems too old to me – would it really speak to your qualifications if it’s missing 1-2 years of experience?

  4. Bend & Snap*

    In this context I HATE the “If I don’t hear from you by X I will Y” approach.

    I had this done to me twice, once when someone used my name to apply for a job without my permission (before I had even seen her message about the timeline), and once when someone was asking me for pro bono work.

    Super pushy and not in the spirit of asking a favor.

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