Ultimatums delivered nicely

I’ve recently had to ask some people I like to get their asses in gear. It’s an interesting question how to be firm with people who are disappointing you, even though you want to maintain a good relationship with them.

Here are two tales about this. Consider what you would write to these folks, and what tone you would take.

The sick accountant

I use a medium-sized accounting firm to do my taxes. The taxes for 2021 were particularly challenging because I sold a house, bought a house in another state, used a temporary loan from retirement accounts to finance the purchase, and moved my business (which meant tracking all my income and expenses in two segments, divided into before I moved and after I moved).

On top of that, I asked the firm to give me a different accountant for 2021 taxes because I was dissatisfied with last year’s person, plus, the accounting firm was in the midst of a merger.

The person they assigned was very responsive. We were nearing the tax deadline and I needed to file an extension because I would not be able to pay attention while taking care of my dying father. She was extremely pleasant in dealing with all of that.

Now, of course, it’s time to actually file the return. And unfortunately, the accountant’s email keeps indicating that she will be back at a date that keeps slipping, three or four days at a time. The reason for the shifting dates for her availability is that she caught COVID and is recovering. I am sympathetic. And the deadline is not really urgent. But I want to complete my taxes, and “at some point in the future” is not really a date I can be happy with.

Rather than call her managers — who are people I don’t know in the merged firm — I wanted to create a message allow her to take charge of solving the problem. I wanted to be firm but sympathetic. Here’s what I came up with. (I’ve changed the names to protect the privacy of the company and the accountant).

Darla, thanks for your attention on this. I am sympathetic to your situation with COVID and hoping you will recover soon.

I have made the estimated tax payments as you requested.

I think it is best to set a deadline here, since I need to know when I can get this return completed. 

If you can complete the return and get it back to me by June 17, let’s do that.

If you cannot complete the return by then, please ask [your accounting firm] to make alternate arrangements with another accountant. I hope this is not necessary, I would prefer to continue working with you.

The client that can’t figure out how to pay me

I have a book editing and coaching client who is the CEO of a large research institution. I am working with him and his COO. He’s very busy, but our conversations have been productive.

They somehow managed to push through my first invoice, but there has been a problem with the next one, for $7,500, which is supposed to be paid before we can get started on a big part of the project. I’ve begun this work, but I would like to get this portion paid to go forward. They have generated a purchase order which shows that they have a commitment to pay me on this, but I can’t seem to get my invoices to stick in their system.

The COO proactively asked if I was getting paid properly, and when I said I wasn’t, referred me to a person in their accounting department and a senior financial person in their organization. Both responded quickly. Neither has caused anything to happen that shows a commitment to pay.

I don’t need to get paid instantly. I just need some indication that the machinery to pay me is moving.

Here’s what I wrote at the end of my most recent email about the project, after a bunch of more substantive stuff about the book.

Finally, it is an unfortunate truth that it is hard for me to remain motivated on this when there is no indication that my invoice is scheduled for payment, or even that it is in process somewhere in your payment system. I’ve made inquiries to the people you suggested and have no clarity on what is happening. If someone could move this forward, it would allow me to make some progress — provided I get some feedback from you on the [substantive book-related] topics above.

Unpleasant emails to pleasant people

I like my accountant. I like my CEO and COO client. I don’t want to throw a fit or be nasty to them. That’s partly because they haven’t behaved in a way that warrants anger from me, but also because I want to maintain good relationships.

That said, if I don’t get my taxes filed and my invoices paid, I’m going to be pretty unhappy.

How do you communicate in this situation?

  • Be cordial.
  • Be sympathetic.
  • Indicate what you need and what the deadlines are, in a straightforward way, and without equivocating.
  • Describe what you’ll do if they don’t meet your needs.
  • Close in a hopeful way.

In this situation, communication should, if possible, be a little witty or funny. Often, as in these two instances, the client is as much a victim of the system (or of illness) as you are. This approach takes the edge off. No one should be confused about what you are asking for, but a cordial approach makes it more likely that they will solve the problem, rather than seeing you as a pain in the ass.

It’s also important that in both of these situations, it’s clear that a solution is possible — and that it’s more likely to happen if you can nicely convince your contacts to make your needs a priority.

There is always time later in the process to get nasty, go over people’s heads, or create a stink on social media. Don’t start with the nuclear option, don’t even threaten it . . . at least not before you’ve tried stating your ultimatums nicely.

I’m curious. What do you do when nice people that you like aren’t doing what your business relationship requires? I’d love to hear your strategy.

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  1. These tips are probably the best to be found anywhere. Thanks.
    I hadn’t thought of these sorts of ultimatums. When I think “ultimatum,” I think of a toxic threat, like, “Either your mother goes or I go,” or “Either you sell that motorcycle you just bought or it’s over between us.”

  2. It helps me to take a step back to examine what the business relationship actually requires and monitor my tendency to conflate a requirement with a preference for what I want when I want it. Using your example, to impose a June deadline on a professional suffering from COVID (I assume it’s symptomatic) for a tax return due in October seems unreasonable to me and lacks empathy. But if I’m wrong about the October deadline, I withdraw the comment.

    1. Garza, I can understand how this looks without a little context. But the return was supposed to be filed in April, and it is now June. The accounting firm has multiple accountants, it’s not just this one person. And I don’t get my refund until the returns are filed. So while the official deadline is October, I think my expectation that this gets done more quickly is reasonable — it’s already more than a month late, from my perspective.

      1. You could be running into a professional culture oriented around regulatory deadlines. Absent a compelling reason to expedite your filing and remove it from the October queue, there could be a strong tendency for your accounting firm to default to the regulatory timetable. (I’m extrapolating from my experience as a lawyer, so am out on a limb a bit.) I don’t know whether your desire to obtain your tax refund is compelling (could be, depends on context), but the fact that “it’s already more than a month late” doesn’t seem compelling, especially because your unfortunate circumstances caused the miss in April. Then again, among some professionals, a client’s request, whether customary or not, is compelling per se, and I gather this is the level of client care you expect.

  3. I like to be very clear about what my expectations are to get the situation resolved. I also like to be clear about what outcome I am looking for. The challenge I have is controlling my emotions in asking for the above. I am working hard to be less “passionate” in my asking. Goals.

  4. Great emails, Josh!

    Here’s one of my stories: A potential client emailed me to ask if we could do a quick chat over Zoom about Wikipedia. His firm has several clients who want their own Wikipedia page, which is one of my specialities as a ghostwriter.

    What’s the problem?

    1. Every call does not need to be a video call.

    2. There’s no such thing as a 10-minute call.

    3. In my experience, 95% of these informational calls can be (swiftly and comprehensively) handled via email. To be sure, once we get to a certain point, I’m more than happy to do a call; in fact, I want to. But if I have to schedule calls with everyone who asks, I wouldn’t be happy, productive, or profitable.

    4. In the course of these “fishing” calls, I end up giving away advice that clients otherwise pay me for.

    So how did I respond? Here’s the reply I sent back:


    Many thanks for getting in touch. I’d be happy to help, especially since I’ve partnered with a variety of P.R. agencies, as both a white-labeled subcontractor and third-party consultant.

    I try to make the resources on my website comprehensive, so I generally charge for Wikipedia calls. For example, on my site, I outline my process, discuss price, and link to my white paper on the six rules of Wikipedia sourcing.

    I also offer all prospects a free, email-based consult, so if you have a client in mind, please let me know.

    All that said, it sounds like you want to chat, so if you have questions that I haven’t answered above, I’m happy to schedule a 20-minute call next week.

    Thanks again. I look forward to continuing the conversation.