#692: My boss wants me to call the person who used to have my position…the person who was fired…and pump her for information.

Dear Captain,

About two years ago, I was hired to work at an awesome but small non-profit. I spent my first year in a low-end administrative position that quickly became mundane. However, after taking on additional projects and consistently showing my skill and desire for more intensive work, I received a huge promotion to a development position. I now answer directly to the CEO, and things are going pretty well. I just brought a new donor on board, and everyone is singing my praises.

However, a huge mess of awkwardness has arisen.

The woman who held the position before me had years of experience in writing and development. She had a VERY good salary (from what I hear) and was close friends with the CEO. However, her performance was less than stellar. In an entire year in the position, she never brought a donor on board and failed to document most of her contacts. Because of this, the organization asked her to resign early last year. Since I took over eight months ago, I have been trying to fill in the informational gaps. In some cases, I’ve had to start from scratch.

Now, this woman had a list of potentials she was trying to develop, and my CEO (still hung up on how “experienced” she was, IMO) wants me to pursue them. However, I do not know (because of the utter lack of documentation) what the other woman’s relationship to these entities were, and some of them appear to be real long-shots. So now the CEO is asking me to CALL THE TERMINATED EMPLOYEE and ask! I’m so uncomfortable with this request, you have no idea. When she worked here, I was just a low-level associate. Now I’m supposed to tell her that not only have I taken over her old job, I want access to her contacts, too?! It seems insulting. I’m thinking about telling my boss that I just can’t do it. It’s not just an affront to her pride, but also to mine. What do you suggest?


Too Appalled to Call

Dear Too Appalled:

In my opinion, you don’t need her at all. This supposed list she developed is a MacGuffin like the Glengarry Glenn Ross list of magical “leads” that your boss is fantasizing about, and the time you spend dealing with her could be better spent by you developing your own list and your own relationships with those potential donors. People who do any kind of philanthropy can handle the concept of staff turnover and getting communications like “Hi, I’ve recently taken over as Director of Development at Awesome.org, I’d love to invite you to a speaker’s series we are doing.” You are capable of doing your own strategizing, and good news, you’ll probably keep a phone/contact log in the file and/or enter the info into a database so that others can pick up your trail someday if necessary.

It’s possible she can’t talk to you – Ex-employee may be working in a development role for another organization, and want or need to keep whatever relationships she developed for herself and not want to open herself up to a conflict of interest. If the relationships with some of those potential donors are her personal relationships you don’t want to set up a situation where she poisons the well there for you. Right now, most likely your organization has at worst a neutral relationship with these places. This connected, “experienced” person telling her friends about how “those assholes fired me and hired ‘some kid,’ and then they made that kid call me and try to pump me for information about you because the boss was too much of a coward to call” is not going to get you in any doors.

If the boss wants to consult ex-employee, the boss should call her, and on the basis of their history and friendship the boss should ask and pay her to consult. “Ex-employee, can we pay you a consulting rate to document where you were with x, y, and z contracts for us?” or “Ex-employee, can we pay you a consulting fee to speak with Appalled and bring them up to speed on some of the prospects you were developing for us.” If she says “sure” instead of “AHAHA NO”, then boss can say “Ok, here is a consulting contract for a set amount of time with set deliverables,” which would recognize her value and give you and she a structure for your awkward day or two of working together. Deliverables could be something like documenting what contact she made with donors and when, and the contract can put something in writing about conflicts of interest and non-disclosure to protect your organization.

If boss will not pay, boss should not call. If the boss is too chickenshit to make the call, no call should be made. This leaves you in an awkward position, obviously, because ultimately the boss is the boss and they can put their foot down on this if they want to. Scripts for you:

  • “Boss, I think that request comes best from you, given your long relationship.”
  • “Boss, can you be the one to reach out to Ex Employee first/make the initial call? I think she’d take the request better if it came from you. If she agrees, I can follow up right away with the details.”
  • “Boss, are you able to offer her some pay for her time and a set of deliverables? That would make things less awkward for her, and give both of us some structure for working with her.”

Okay, say your boss orders you to call her or email her and you have to do it. Script: “Ex-Employee, this is Appalled from Awesome.org, how are you? Boss asked me to check in with you about Potential Donor List – would you be willing to give me a few minutes to run down the list and just briefly tell me where you left things with each person/org?

You don’t have to mention that you are in her former job (she’ll get it) or apologize on behalf of your boss (she’ll get it). Keep feelings out of it and make a clean, direct request. If she says no, thank her very much for her time and let it drop. If she gets really sour, acknowledge her feelings – “I agree, this puts you in an awkward position, I am sorry” but don’t get sucked in to badmouthing the organization or your boss or a gossip session. If she will help you, be as quick and professional as possible and then, under your own steam, send her a personal thank you note and “endorse” her on LinkedIn for some skills or write her a brief recommendation there, like “Ex-Employee consulted for me briefly on some development strategies, she was gracious and professional throughout and her expertise was most valuable.” Fundraising is a small world, and even if she wasn’t a great fit for your organization at that time, you are likely to run into her again in your career. Treating her with as much dignity and decency as possible won’t hurt you professionally or stain your soul, and as the person who has the job now, you can afford to be magnanimous.




38 thoughts on “#692: My boss wants me to call the person who used to have my position…the person who was fired…and pump her for information.

  1. I would skip trying to toss the football back to Boss, and go right to the suggested direct contact script. I think that a good deal of the awkwardness comes from the expectation that Ex-employee can’t or won’t give the information. Well, that’s not really LW’s problem. I’d make the call, acknowledge the “yep, I’m doing your job now, boy you made it look so easy” kind of thing, and then report — honestly — to Boss the sad news that Ex-employee was no help. Boss just wasted LW’s time, but that’s not really LW’s problem. It could even be, as suggested, an opportunity to connect with others in the nonprofit development arena.

    My fear is that the first course of action the Captain suggests may make LW look like they are trying to get out of doing a task. Which may remind Boss of the employee who was terminated. So I say just make the silly call; be polite and as friendly as you can be; and get it over with.

    1. This is not a bad call at all, and is certainly the quickest way to get this done and over with. The Ex-Employee already knows how awkward boss can be and may not even be surprised.

    2. I’m inclined to agree with this. Doing fundraising for a small organization where you are a team of one and your boss is the CEO (and possibly with no fundraising experience) – you may be presented with a lot of silly questions or ideas. And being able to tease out which ones are actually good ideas, which ones you process quickly but are obvious dead ends, and which ones you push back on because they’re actually bad ideas. And my experience those bad ideas were usually more along the lines of “why can’t we just change the project midstream and not tell the donor?”

      There are Buzzfeed lists full of development eye roll moments (have you been asked to write a letter to Oprah yet?) that are honestly best to just power through and be done with. And the plus side – development is an inherently awkward profession. Asking for money is awkward! I’ve found that embracing the overall awkward reality of a lot of what we do has made the job much easier for me. While the whole “imagine everyone in their underwear” style of advice is a bit cliché, it really helped me – particularly with donor sponsored events. Putting the whole professional sphere in the context of “this is just weird” made my own awkwardness relax.

      1. “Doing fundraising for a small organization where you are a team of one and your boss is the CEO (and possibly with no fundraising experience) – you may be presented with a lot of silly questions or ideas. And being able to tease out which ones are actually good ideas, which ones you process quickly but are obvious dead ends, and which ones you push back on because they’re actually bad ideas.”

        This. So much this. You are about to learn so many skills to politely tell your boss that their idea is completely unworkable and generally terrible. I recommend developing your professional knowledge of fundraising ASAP so that you can position yourself as the expert as soon as possible. It’s particularly helpful if you can become The Database Expert. Because very few people want to think about data and queries and suppression lists, and practically no one wants to The Database Expert. So it’s a great way to be like “hey, that idea you have about changing everything two days before the direct mail lists are due? As much as that sounds AWESOME, we can’t do it. Because of the database, and how tricky it is! Next time, let’s talk this through a month or so ahead of time so that we can make sure we incorporate your Totally Awesome Idea into it, boss!” Managing up ftw!

        I also really recommend Kim Klein’s book, Fundraising For Social Change.

        1. I so adored this, as a professional Database Expert. And truly, civilians are utterly clueless.

          The worst thing about your first bizarre boss request is the sinking feeling it won’t be the last. The path to Bossdom should be “awesome handling of employees and their skills” but this so rarely happens because it is a rare and amazing ability.

          However, if one has it, one is going to do very well. So it’s also an opportunity to Boss, on the road to becoming one of those rare and valuable creatures.

    3. I Nth this. Just make the call. Yeah, it’s kinda awkward to call someone who was shown the door. Yeah, probably boss should do it (though I can think of several good reasons why not, one being that this is the sort of thing they should have asked her for in exchange for any severance) but clearly s/he won’t.

      On the flip side, I think there’s plenty of reasons NOT to feel awkward. So you have her old job. So? Someone was going to. She’s not a deposed ruler of a country, and maybe she was not doing well there because it was long past time for her to find something she liked better but the golden handcuffs kept her around. She could be happier than ever where she is now and thinking that being pushed out was the best thing ever to happen to her.

      Or maybe she’s bitter and angry. But none of this is your fault and we all leave behind gigs. I think most professionals shrug and make a token effort to be helpful when folks from the past contact them. I have done so even when I was so happy not to be at the old place anymore because I knew that the person asking was in a place I’d been in, trying to just get the job done. I answered questions for their sake, not for the boss or the company I didn’t care about anymore.

      She might shrug you off and it might be perfectly deserved if they treated her badly. But that’s not about you. You’d just a person asking another person for a little help.

  2. Hey LW, I’ve been in Ex-Employee’s position before (the being asked to leave and then pumped for information position, albeit in a different field and for different reasons) and I just wanted to offer a bit of perspective. The kindest thing you can do is not contact her. However, if you absolutely have to, keeping things as task-driven and professional as possible like the Captain suggests will keep the pain to a minimum. A thank you note or LinkedIn endorsement if help is given is a brief time commitment on your part but will probably be a HUGE gesture to, and much appreciated by, Ex-Employee. The most painful thing for me was being pumped for info and then never spoken to or acknowledged again by the person, even though we ran in the same circles. It made me feel used and gross.

    1. A trick I’ve learned is to address a thank-you card before you talk to the person, talk to them, write it up right after the conversation is done, and drop it in the post later that day. That way it’s easy to remember and the timing is relevant. I think something similar with emails or linkedin messages might work.

  3. Not that this helps, but I hate chickenshit bosses. I currently work for one. And I worked for *her* chickenshit boss before that. Can’t (won’t, really) make a single decision. Ever. Absolute nightmare. it’s a work culture thing, I get it – but they shouldn’t be working in management if they can’t actually MANAGE anything.

    1. I read a line somewhere about people being promoted to their level of incompetence…

    2. Agreed. I’ve worked for boss that have made me be the bad guy (to other employees), delivery bad news, or do their dirty work. It’s cowardly. I can’t respect those kinds of managers.

  4. As someone also in fundraising – I strongly recommend the Captain’s advise. I would also add that prospecting lists are kind of a dime a dozen. If your boss isn’t interested in investing consulting dollars in the fired employee, there are subscription websites like Foundation Directory that are great for building prospect lists. And then the time honored tradition of just looking at the donor lists of organizations similar to yours and reaching out to their donors.

    The chance that there’s anything on that prospect list so amazing it’s worth crawling over glass to get, I would put the odds at really low. However, I will also say that as someone who’s done fundraising for a while, I’ve had more than enough CEO/Director bosses who think that some huge donor is just a single phone call or perfect letter of inquiry away. So while it’s worth pushing back a little on reaching out to this old employee, ultimately be prepared to make that awkward call and be as professional as possible is a good general professional development for this field. Being able to go on that silly goose chase in an efficient manner, get the results for your boss (which are often “I tried xyz and there are no funds”), and move on to real work is good practice.

    1. Quite. And what makes the difference is having an amazing proposition to put to the donor. Simply identifying contacts and starting/restarting a conversation with them is not going to yield the dividends the boss thinks it is.

      1. It’s definitely a whole process, and there’s definitely no magic list that’s suddenly going to bring with it lots of easy money. In one job I had, there was a foundation donor that was brought on primarily because of a relationship that the program officer had with my predecessor. That foundation became my white whale of “never going to happen”. But then there were other organizations that my predecessor had never been successful with, but when I started it was a case of right time, right people, right project and they were some of my easier donors.

        I would also suggest to the OP, if it’s possible, to find/participate with some kind of fundraising group/forum. Especially when you’re in a small organization, it can be invaluable to have those relationships. Particularly given how the nature of fundraising can be a be competitive, finding those balances between supporting and sharing with your colleagues (while keeping other issues more guarded) is really helpful.

      2. Misread “proposition” as “preposition.” Thought, well, “before” works very well!

  5. I think the Captain’s scripts, especially for the Boss, are right on. If the boss is not willing to pay his ex-employee or even call her himself, then obviously that magical list is not that important to him.

    I think that bouncing the ball back to your Boss is also a good gauge for how things will pan out with this mess. If he really does not get that this is not a good idea and has not thought about how it could blow up (her poisoning the well, for example – I have seen that happen), then he will certainly not have your back during any of it. This gives you information so you know to be as careful as possible and make it clear that these orders are from the Boss, not you. [I actually make a point of telling my employee to blame me for things if people are giving her a hard time, because “you know I can’t argue with the boss!”]

    Your boss never should have tried to put you in this position, LW. I wish you luck!

  6. LW, your boss is an ass. For one, your predecessor left early LAST year and he first now wants the leads she had?? This is a conversation that should’ve taken place way back when she was transitioning out of the role, not over a year later. For two, he seems to me to be of the mindset that people who work in the non-profit arena are sooooo dedicated to the cause that they’re willing to give their time and ideas for free.

    I like the idea of pushing back on the boss. Especially floating the idea that he should be prepared to pay Predecessor for her time, especially since it’s been so long since she left. Your boss sucks and I’m so sorry!

  7. Le Sigh. I, too work in fundraising, and this fallacy is as common as the CALL OPRAH! SHE HAS MONEY! fallacy.

    First, go YOU! You brought a new donor on board in eight months! That is fantastic!

    I’d follow the Captain’s advice. I sincerely doubt this person had anyone ready to sign on as a major donor given her work record.

    How much development experience does your boss have? I’ve seen this a lot throughout my career–the head of an org who doesn’t know much about fundraising tries to run the fundraising effort and uses their own assumptions as gospel truth. It doesn’t tend to go well. And honestly, I’m wondering why your boss didn’t meet with her and touch base about where she was in this project while she was working for your org.

    It sounds like these are people who are known to your organization and that it’s been eight months (or more) since anything has been done with them. So I’d actually just start fresh with them (if they have some sort of existing relationship with your organization). You’re still fairly new and it’s not unheard of to contact people to introduce yourself and update them on what the organization’s been doing.

    Otherwise, ITA with the idea that if your boss wants to pump her for info they should hire her as a consultant. Your boss should absoloutely be the one to call her if they insist on this, though YMMV on how easily you can push back. I’ve worked for impossible people before so I get it.

    1. There’s nothing quite like the first “Dear Oprah*” letter you get to write….honestly though, this is also so common in the fundraising world. So having a “I am the new Development Professional here to introduce myself” line that works for you can last you well into your second year if necessary. But yeah…for the most part, none of us have prospecting lists so amazing that if they ended up in the hands of anyone else it’d be a gold mine.

      I will say, while your Dear Oprah letter/phone call may go absolutely no where – it’s not horrible practice. Having a boss who brow beat me into calling person after person where we had no logical shot, I did gain amazing phone skills and an ability to be able to set meetings with some pretty high level people (though not Oprah). Realizing you’re unafraid of making the call “Yes, I’d like to set a meeting with the Ambassador for this month” can be kind of fun.

      *insert the name of any famous type person with lots of money and vaguely connected to the interests of your organization

      1. “for the most part, none of us have prospecting lists so amazing that if they ended up in the hands of anyone else it’d be a gold mine.”

        This too. Prospects aren’t good or bad because they have All The Moneys OMGZ. They’re good prospects because they care about your organization, someone has a personal relationship with them, and they are willing to give money to SOMEONE (e.g. don’t bother with people who don’t give money at all, to anyone, ever). So I agree with the other advice in this thread about building that relationship. You can just reach out and being like “hey! I’m the new development person here! I’d love to grab lunch with you sometime to get to know you, hear about your passion for and let you know about the stuff we’ve got going on this Spring.”

        1. ugh, that was supposed to say “hear about your passion for [your mission] and let you know…”

    2. That’s what I thought. I don’t know jack about fundraising, but either her list was really not going very well at all, or it was made up. Either way, I doubt there are secret hot prospects the ex-employee knew about that they can take advantage of.

  8. If you decide to talk to your boss and pushback against this, what about telling him (her?) that this phone call could backfire? Something, “Hey boss, Ex-Employee may still have relationships with the donors. I’m worried that if Ex-Employee is offended by my phone call, that could reflect badly on us and these donors may actually decide not to give us funds.”

  9. This may be blatantly dishonest, but what are the chances LW could get away with just -saying- they made the call and that it went nowhere? That’s likely to be the outcome anyway (especially if Boss isn’t offering to pay for the hassle or do it himself), so this could possibly save Ex-Employee any potential insult or hard feelings about the company.
    This is probably a terrible idea.

    1. Since the LW mentions the CEO and the Ex-Employee were close personal friends before her leaving, I wouldn’t risk it in case they’re still friends and the CEO decides to bring up the call with Ex-Employee, who then replies “what call?”. Too many ways for it to backfire.

  10. Another fundraising professional here. Donors give to your organization based on the relationship that they have with your organization. You’re going to steward and build those relationships from now on, regardless of the history. It’ll be a bonus if you can find out the prior relationship but if that’s not practical, you can also start from scratch with each prospect, and do your best to build a great relationship with them.

    I would certainly not tell your boss that you can’t bring yourself to call the ex-employee. Fundraising is a relationship business and, as eightysixed says above, there are bound to be awkward moments and conversations. Think of this call as relationship-skills practice: it may not be the last difficult phone call you make as a fundraiser. Good luck, LW!

  11. I’ve done these goose chases before. You put in a simple, courteous call – a “hey, I know this is sort of weird given the history, but Boss wanted me to ask you about your list. Let me know if that’s an issue with you.” Give her an out yourself, quietly accept it, move on. Tell Boss it just didn’t work and there’s not much use of the list anyway.

    I personally wouldn’t try to escape doing it by throwing the work back to my boss, but I’ve had that backfire before. It depends on how reasonable a manager is to the idea of an employee giving a soft no. In my experience, not very.

  12. Different sort of position and knowledge to pass on, but I was laid off with no notice, warning, or severance pay once. (They specifically told me later I could say I was laid off, not fired.) My successor called me with questions, and I helped her at first, then told her these were my last answers. Told her boss that he could call the way they laid me off “standard” if he wanted, but couldn’t have it both ways — I wasn’t also going to train my replacement for free. It was a pity, I’d really wanted in my time there to make it easier on the next person, but… no.

    All this to say, if you make that call, and if it makes her mad, I doubt she’ll be mad at YOU.

    1. Yeah, it will be fairly obvious you were not the person to decide this call should happen.

  13. Holy smokes, bosses. I had a boss who wanted me to call the company that LAID ME OFF and pump them for information. Awkward. Something happens to people when they get into positions of authority. LW, you have my sympathies.

  14. I haven’t been in this situation, but I actually kind of feel like if I was fired, I’d be happier to speak to my replacement (just trying to do a job, in the end) than to my former boss who fired me. If I had a bad relationship with a former boss or if things ended in a strained way, I’d probably find it more uncomfortable and painful to get a phone call or email from them than from someone more neutral I don’t have a negative history with.

    How much I’d help would probably depend how much effort it took me, or whether the information was still useful to me, but even if it annoyed me to be asked or if I said I couldn’t help much, I don’t think I’d particularly blame the person asking, or find it as awkward as having the same conversation with someone who fired me.

  15. Development person here, and honestly, I wouldn’t think of the list as “her contacts.” You don’t know if they’re her contacts! You’re calling or emailing because you have this list in the files, and you want to make sure you’re not telling these folks anything they already know about the organization before you reach out. She’s well within her rights to say “sorry, can’t help you,” but then you’re no worse off than you were before, and you can tell Boss you tried.

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