Sorry, Not Sorry. Why Do We Apologize So Badly?

Writing bad news in business feels almost as unpleasant as reading it. But if we keep our reader(s) in mind, and follow some simple organizational rules, your reader(s) might respond better than you think. I’ve offered several tips for crafting successful negative messages in this blog. In our follow-up, let’s critique some awful examples of poorly written (and executed) negative messages. Alas, so many exist! We’ve also found an A- grade message to hold up, too.

Sears CEO, Eddie Lambert

Sears announced its new round of layoffs in February. The retailer tends to frequently layoff staff around this time of year, Business Insider states, and shares this sample from an internal email:

“This activity is necessary to create a more nimble operating structure capable of driving the company’s strategic transformation forward,” Lampert wrote in the email. “We highly value all of our associates and do not take these decisions lightly.”

My critique for Mr. Lambert:

  • Replace your weak verb ‘is’ with a more active one like ‘remains,’ ‘feels,’ or even ‘becomes’ for a kinder, more executive tone.
  • Remove your camouflaged verb ‘transformation’ to avoid a jargon-y or promotional/vague tone. (The real verb ‘transform’ might help the message, but remember: those who lost their jobs won’t feel transformed.)
  • Avoid the redundant, repetitive, and ubiquitous statement of not taking these decisions (another camouflaged verb) lightly.  You’ll sound more sincere (and more sorry) if you share your real feelings more candidly. Ask yourself: How do I feel? Whatever comes next provides precious fodder for better word choice.

HCSC Spokesman, Mark Spencer

When Chicago-based health insurer Health Care Service Corporation announced a large IT layoff , employees responded very badly to the idea their role would get outsourced. Part of the issue likely lay in the poor choice of tone and wording. Check this sample from Business Insider:

“We are transitioning to a blended operating model in which basic operational tasks are handled by strategic business partners, and critical strategy and design work is performed by HCSC employees,” the statement said. “The new model uses more flexible and agile ways of working with new tools, allows us to invest in developing new capabilities and innovation, and reduces complexity related to years of maintaining legacy systems.”


“We do not make decisions about our workforce lightly, and we are committed to ensuring employees are supported throughout their transitions,” said Spencer. Employees will get severance and “transition” services, he said.

My critique for Mr. Spencer:

  • Use contractions for a warmer, kinder tone—you’re letting people go.
  • Remove passive voice to help create a more sincere, engaging tone. (E.G. We’re switching to a blended operating model in which business partners handle basic operational tasks and HCSC employees perform critical strategy and design.) Even this edit sounds a bit vague, but hopefully less so without the passive voice.
  • Avoid vague, jargon-y phrases—you’ll only confuse your already upset reader. What does “the new model uses more flexible and agile ways of working with new tools,…” etc. mean? I’m lost. Use plainer, clearer language to sound more executive.
  • Try capping your sentences at 20 vs. 34 words to help retain your reader(s).
  • Embrace more unique language to sound truly sorry. (See earlier note on “not taking decisions lightly.”)

Ev Williams, CEO of Medium

Kudos to CEO Ev Williams, premier of the blogging platform Medium. In this message, the Twitter co-founder follows many of the best practices we suggest by:

  • Using a conversational, likable and approachable tone
  • Sounding sincere and heartfelt on how the layoffs make him feel
  • Stating some of the essential elements of the bad news (the layoff of 50 teammates) right up top (i.e. sentence two)
  • Offering helpful specifics
  • Pre-empting many of the core questions the reader might have

 My critique for Mr. Williams:

  • Bring up all bottom-line info to your launch paragraph. You deftly tell us you’re letting go 50 employees in your opening sentences. In the later paragraphs, almost at the end, we learn more pivotal details on who specifically goes (i.e. shutting the New York and DC offices, some executives go, most product development and engineer folks stay). Keep all the pivotal stuff high to avoid panicking your reader.


  • Keep the message shorter. While Mr. Williams (or his writer) writes very well, the message remains long. Several paragraphs on his early hopes and visions for Medium feel redundant— or worse, indulgent—given we wade through several paragraphs to learn specifically who leaves the ship. Remain brief. You can always offer more specifics in a company-wide meeting.


  • Avoid fluff before the specifics on the lay-off strategy to maintain that early direct, executive-sounding approach. It takes four sentences of vague, wordy messaging before we learn who goes in those later paragraphs. I’ve line edited in red to show the redundancies (and to remove false subjects, weak verbs, and the vague ‘it.’) If the CEO really wants some buffer, compress to: We realize this new, more focused strategy, remains less proven—but we know it takes time (and trying some different skills) to get things right. (Even this edit still sounds vague, admittedly. Removing looks best!)

It is too soon to say exactly what this will look like. This strategy is more focused but also less proven. It will require time to get it right, as well as some different skills. Which is why we are taking these steps today and saying goodbye to many talented people. To stay efficient, we are shutting our offices in New York and Washington D.C. (though some people will continue to work remotely from those locales). And we will be parting ways with some of our executives who were brought on to scale these teams. The vast majority of the product development and engineering teams will remain, both to support the Medium you love and to bring it to the next level.

  • Remove passive voice where possible, especially in bad news messages, to avoid sounding weak or evasive. E.G. .. We’ll part ways with some executives we brought on to help scale these teams.

Read more Hanging Rock Media blogs here. 


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