yet another email verbiage question!
December 31, 2018 11:07 AM   Subscribe

I have to write a somewhat complicated email to my boss. Please help me figure out how to word this without writing a novel.


I manage operations at a local arts business. This is a part-time job, but I have done so well in the position that my responsibilities have increased ten-fold from when I started two years ago. I have a client from my past life as a freelancer in a different industry, but the client doesn't really need me anymore so we are winding down our work together. The arts business has grown enough that I really could turn it into a full-time job, but of course if we do that, I want to be paid more, both to make up for the money I will no longer be getting from my client and also because if I'm going to be putting in more hours I deserve more compensation.


The bookkeeper at the arts business is straight-up incompetent. I have purposely not weighed in on this thus far as it's not really my place in the role I am in and I don't want to overstep with my boss, but I have been managing financial matters in all of the jobs I have held over the past ten years prior to now, and was also doing books for the client I am about to retire. However, the bookkeeper's inadequacy is now getting to the point where it is reflecting poorly on the business and has the potential to do really lasting damage long-term to our reputation and to our finances. The bookkeeper routinely makes errors with payroll and with billing, which according to other employees predates me at this company for years. The bookkeeper also recently got a full-time union job at a company that is her dream job, and she very clearly no longer has the time to keep up bookkeeping as her side hustle, so these errors are getting worse and worse. She is very defensive about this when called out on her errors. In the last two months, she has made some errors that are absolutely inexcusable - late paychecks resulting in one employee missing a mortgage payment, misplacing a customer's credit card information, charging another new customer's credit card three times in error, all while saying that the reason for the errors is because the paperwork she is being given is unclear and she's just been making assumptions about what the billing should be. I do not think the paperwork she has been given is unclear, but regardless, making assumptions about customer billing is just not acceptable from a bookkeeper; if something is unclear she should ask for clarification rather than charge $600 on a customer's credit card without confirming whether that is what she should do. She is hired by my boss as a freelance bookkeeper and she is unfamiliar with our company's operations, which is certainly not helping the situation. In addition to complaints from staff about incorrect paychecks, I have also been fielding a lot of complaints from unhappy customers about the billing mistakes.

My boss is a wonderful person but he has no head for business - this is one of the reasons why he hired me. I don't think he fully understands how bad this already was or how REALLY BAD it has gotten. As a financial professional and someone committed to the mission of this business, I feel it would be unconscionable for me to not put my hand up and say something to him at this point.


The easiest way to solve all of the problems I have listed above would be for my boss to discontinue his relationship with the incompetent bookkeeper and have me take over managing the books. I have experience as a bookkeeper, I understand the company's operations (since I manage them), I have relationships with most if not all of our customers, and I have an excellent rapport with the rest of the staff. Moreover, this would be an easy way to justify making me a full-time employee (managing the books and operations) and giving me a pay increase, as he could simply re-allocate the money he has been paying the bookkeeper to me.

My concern is how to present this to him kindly without making him freak out. Issues pertaining to money management make him nervous and I know that this is why he has stuck with this incompetent bookkeeper for so long; the idea of finding someone else to handle this literally makes him panic. When issues of employee performance have come up in the past he basically sticks his head in the sand; he is terrified of conflict.

I intended to have a conversation with him about making me full time anyway after the new year; the severity of the bookkeeper's mistakes as of late have in theory given me an easy way to start the conversation but in addition to not wanting to cause him to bury his head in the sand, I also do not want to make it seem like I am just gunning for the bookkeeper's job and that's the only reason why I am throwing her under the bus.

The business has grown enough in the past two years that it makes more sense for him to have an in-house bookkeeper/business manager. He has never written a budget. We are a business with gear and equipment that need to be replaced or maintained every now and again and anytime something breaks there is a scramble to get it fixed as cheaply as possible. We had a tornado earlier this year that leaked through our roof; a huge chunk of money went to those repairs. I have no sense of what he is paying in occupancy costs, or what kind of revenue he is getting from the services we provide and the tenants who use the offices downstairs. If I had a window into any of this, I could do what I have been doing professionally for a decade - working up a budget, helping with financial planning long-term, implementing systems to ensure payroll is accurate and customer billing occurs without error, and generally making sure that we are not spending more than we make. It would be very easy for me to take this on on top of the work I already do for this business - I would essentially be doing for the business what I have been doing for the client that I am about to retire. It literally would be replacing the 20 hours of bookkeeping work I do for my client with 20 hours of bookkeeping work for this business. I'd have a 40-hour/week job, I'd still be managing what I already manage, and my boss can continue to be the Idea Man that he really enjoys being.


I think it would be best for me to have an in-person conversation with the boss about this; we are due for a check in soon anyway now that it's the new year. However, I'd like to send him an email prior to this conversation to give him a head's up that I would like to talk about this. Do I tell him everything I just told you guys (minus the commentary about his tendency to panic about money and staffing issues, obviously)? If so, how do I do so concisely? Or, should I just introduce the topic via email and then write up a proposal to present to him during the meeting I am asking for with him? Or both - should I write up the proposal and email it to him while asking for the conversation? Or will that be overstepping and make him freak out?

The last mitigating factor is that if he is unable to make me a full time employee in this way or in another capacity, I will not be able to stay in this job in a part-time capacity for longer than one more year. I need full-time work and I don't want to go back to freelancing. My health insurance premium under Obamacare just increased by $150 per month, which was unexpected and is making me very anxious. I don't like living paycheck-to-paycheck.

However, this part-time operations job at this business is the best job I have ever had; my boss is wonderful and not a micro-manager, I love the staff and I love our customers (even when they give me agita), and I have done a lot to improve the business's operational processes (including marketing) already; I have gotten tremendous feedback from everyone including my boss about how I have elevated the place to look and run very professionally as opposed to a disorganized dysfunctional small-town small business. I think I could continue to do great things to keep this business successful long-term, but I will only be able to do so if I get paid more than I have been. And honestly, me taking over the books would be the easiest way to justify paying me more.

Any advice as to how I should present this to my boss would be much appreciated. I am bad with concise written correspondence (as this post aptly demonstrates) so specific email verbiage would be especially appreciated. I am not looking for advice that only consists of telling me to run away from this job altogether; that is a last-resort option that I will only deploy if this email and conversation with my boss fails and I would prefer not getting piled-on with advice that doesn't help me with this specific email and conversation that I need to have with my boss. (I'm sorry to be so preemptively dismissive as I don't want to be a high-maintenance member of this community, but I've seen many similar pile-ons in AskMe before and I'd like to head the unhelpful stuff off at the pass if possible.)

Thanks in advance - and happy new year!
posted by thereemix to Work & Money (11 answers total)
I would avoid putting any of the details about the bookkeeper in writing, either in an email or a proposal. It's just better discussed in person, I think. In a proposal, you can outline the job you'd like to have and your qualifications for it/the case based on your accomplishments in the job so far. When you email to ask for a meeting, it can be something as simple as "I'd like to meet to talk about taking on more responsibilities at XYZ" or "I'd like to talk about my future at XYZ." You can talk about your concerns about the bookkeeper in person, tactfully, but focus on the case for yourself more than the case against her.
posted by pinochiette at 11:27 AM on December 31, 2018 [8 favorites]

Hi Boss,

It seems like we are overdue for a check in. When are you available to meet?


I believe that you should save everything for your in-person conversation.
posted by The Architect at 11:28 AM on December 31, 2018 [19 favorites]

I wouldn’t put this in an email at all since you already have a check-in coming up.

However, I would prepare for that discussion by writing it out— you have a great start here, and your sense that you need to edit this down to the essentials is spot on.

To include:
1) present what you can do for them; sell it as a benefit
2) reiterate your love of working there

Don’t include:
1) you can’t suggest your boss fire someone, you just can’t. Let them get there on their own. Present bookkeeping as part of your skill set, and present the benefits of centralizing all functions to one role, but you can’t call someone incompetent, or decide for your boss what to do about staffing.
2) personal reasons for needing more money. Everyone needs more money, you deserve it because of the work you do.

Good luck!
posted by kapers at 11:31 AM on December 31, 2018 [4 favorites]

What you have here isn’t wAY too much detail for an email. What about:

Hi Boss,
During our check-in, I wanted to talk about the potential for increasing my responsibilities within org. One thing I’ve been considering is whether it makes sense for Org to have me pick up more of the bookkeeping work, as I have more than 10 years of background in this through my other roles. I’m happy to give you more context on why I’m thinking about ways to expand my role here, and why I’m specifically thinking about the bookkeeping function, during our check-in.
posted by samthemander at 11:32 AM on December 31, 2018 [5 favorites]

I wanted to add, if there are issues with the bookkeeper that the boss needs to know about, that’s totally fine to bring it up— just not as part of why you should be promoted.

You can work around this during the discussion by saying what you’d bring to bookkeeping: I’d use X process rather than Y process we use now, because Z. (It’s more efficient and eliminates some of the mistakes we currently experience, etc.)
posted by kapers at 11:37 AM on December 31, 2018

I recently had to deliver similar news although in my case I was suggesting hiring a new bookkeeper, and my boss had already stated a few times that he knew he needed to make a change.

I agree that this is better done in person. In person, I would emphasize:

1. That the 'side gig' nature of the relationship is making issues hard to address
2. That angry clients are a reputational and financial risk
3. That the payroll issues may lead to retention issues, as well, depending on your knowledge of your boss's level of caring, causing real hardship to staff
posted by warriorqueen at 11:55 AM on December 31, 2018

Payroll issues can lead to more than retention problems; they can lead to shut-down-the-company lawsuits. A company that is knowingly negligent about payroll can find itself on the hook for extensive costs and criminal liability. Likewise, accidentally charging someone's credit card (and later fixing it) can be excused, but a pattern that can prove negligence - like failing to fix whatever caused the accident in the first place - can put both the bookkeeper and the employer on the wrong side of several laws.

"Oops we charged that person three times" is a nuisance. "...And we didn't change our process so that it won't happen again," is opening the door for a company-ending lawsuit, possible with criminal charges attached.
posted by ErisLordFreedom at 12:47 PM on December 31, 2018 [4 favorites]

I would definitely put together a printed proposal for him, just because if he's someone who gets really nervous/anxious around money stuff, he probably won't retain as much of the conversation as he otherwise would. Having it in black and white that he can hold in his hands will give him something to refer back to as he thinks it over.
posted by Eyebrows McGee at 7:39 PM on December 31, 2018 [2 favorites]

You say your boss is terrified of conflict, can’t/won’t performance manage, and has no head for business. So, do not scare him by saying the bookkeeper is terrible and needs to be fired. That’ll push all his avoidant buttons and make him worried and embarrassed.

Instead, just tell him the good parts. That the business is big and successful enough that it’s time to bring book-keeping in-house: that will be more efficient and more effective. It’ll enable better customer management, things will run more smoothly, and there will be proper budgets which will make his life easier. Tell him that you would like to go full-time and handle it all for him, because you love the organization, and that will free him up from worrying about that stuff so he can look after the big picture. Tell him that if he says yes, you’d be happy to speak with the bookkeeper yourself, and make sure she leaves happy and that the transition goes smoothly. Frame it as a natural evolution of roles and something that will be practically invisible to him.

If he seems receptive, tell him you’ll send him a formal proposal that he can review and approve. If he doesn’t seem receptive, you can say that you might need to leave otherwise: that you love the organization but are wanting a full-time position. That part is risky unless you’re sure you would actually leave, but your point in saying it would be to trigger his disinclination to need to find a new person to replace you. Because you say he doesn’t like that part of the job. So basically you’d be saying ‘I will solve all your problems if you let me’ with the implicit, careful, delicate threat of ‘otherwise you will have to solve them yourself.’

But don’t trash-talk the bookkeeper. That’s the opposite of what you should do. It will just upset him. You want him to associate you with success and harmony and ease, not with pain and tension.

Good luck. I think you’re in a good position to make this happen, and it sounds like it could work out very well for all of you :)
posted by Susan PG at 12:01 AM on January 1, 2019 [6 favorites]

Some of this depends on your relationship with your boss, how much trust there is between you, and how much you've had difficult or vulnerable of "off the record" sorts of conversations before. Of course, email is definitely on the record, so I agree that you shouldn't say anything specific about the current freelance bookkeeper in your email.

If there is a good amount of trust and honesty, you might be able to write something like, "I know you get anxious about finances [and conflict] sometimes, so I just wanted to give you a heads up that our upcoming check-in is likely to involve some of those topics. Don't worry--I think it will definitely be worth it in the long run."

There would have to be an unusual amount of trust and space for frankness to say something like, "For the good of the business, you need to fire x." I do think it's reasonable and probably even necessary to bring up some of your concerns about the freelance bookkeeper--and you could maybe even say something like, "If you decide to look for someone else, I have relevant skills, etc." and lay out the logic you outline here.

edited to add: Other people have made great points about the legal risks, I'm focusing on the interpersonal stuff/communication stuff because that's more in my wheelhouse.
posted by overglow at 8:45 AM on January 1, 2019

There are two totally separate persuasive objectives going on here.
1. "I'd like you to get rid of your incompetent current bookkeeper."
2. "I'd like you to expand my responsibilities and bring me on full time by adding bookkeeping to my job."

Sticking with #2 will be best, I think. It'll allow you to focus entirely on your strengths and why doing this would be great for the organization.

In general, think of this as a job interview for a job you don't yet have -- focus on your strengths, why you'd be a great hire, and what you can contribute to the organization. I'd suggest framing it as "The organization has grown to the point where it needs more," vs. "She is incompetent," -- the first allows you to pitch your strengths, while the second gets you bogged down in negative stuff that isn't really about you. If your boss turns the conversation to the current bookkeeper -- "But what about Bookkeeper Jane? I can't fire her!" -- you can just turn it back to your job interview -- "I do think that as the org has grown, our finance needs have grown too. In my experience with other clients, I've seen this transition before, and I think that the X, Y, Z I can offer will help us get to the next level of success."

You should decide for yourself how frank you want to be about the fact that you may leave if he doesn't find a way to make you full-time; sometimes that can be a very good think to say so long as you put a positive spin on it ("I'd like to be able to stay," vs. "I'm threatening to leave"). Don't bring this up (even indirectly) unless you're willing to follow through on leaving and have good prospects for doing so.

For the email, I agree with pinochiette -- that email language is just about perfect. For the meeting itself, you might want to prepare (1) a draft job description for your new proposed position, and (2) some talking points.


As you know, I've been taking on more & more responsibilities here. I love this place, I love this job, and I really want to make it into a full-time position that I can stick around in for the long term. I have a proposal for expanding my role in a way that I think will benefit [arts org], and I'd like to know what you think about it.

The proposal: I'd like to continue with my current duties, while adding 20 hours/week to take responsibility for bookkeeping and finance, making my role full-time. This would mean bringing bookkeeping duties in-house, which would make the organization as a whole more efficient and effective.

Here's why I think this will benefit [arts org]:
- I can see that over the past X years, as [arts org] has grown, the finances have gotten more complex and more high-stakes. I truly believe that it would be to the benefit of the organization to have an in-house bookkeeper who is closely involved in operations and able to respond fast to the org's needs.
- Specifically, I believe that existing duties X, Y, and Z would benefit in [these specific ways].
- I also believe that, as we've grown, it's become more important that we do currently ignored tasks A, B, and C.
- Being available full-time would mean that I'd be more responsive and available for urgent financial tasks.
- I believe I've done good work that has helped the org succeed in XYZ ways. Making my role full-time will provide stability for the org over the long term.

Here's my experience & what I can offer:
- as you may know, I have about 10 years of experience in bookkeeping and financial management. I'd be happy to put you in touch with [other clients] for a reference if you'd like.
- I have specific experience in payroll, bookkeeping, payables, receivables, budgeting, general financial management, etc. My work has helped my clients become more stable and profitable, and I believe I could do the same for [arts org].
- I believe my experience managing the org gives me insight into the org's financial needs in XYZ ways.

Options for wrapping up:
- Do you have any questions?
- What are your initial thoughts?
- Is there any other information you'd like me to gather that would be useful as you consider this proposal?
- I've drafted a job description for what I believe this new role would look like. Can you take a look and we'll talk it over next week at our regular meeting?
posted by ourobouros at 8:56 AM on January 1, 2019 [2 favorites]

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