Handling awkward emails

Awkward emails often convey bad news, handle complaints, decline offers, and resolve other difficult situations.

 

The emails you dread

In the previous lesson, we learned about choosing the right tone for emails . Now, let's build on that foundation. Some emails are so difficult to write that you procrastinate, rewrite them repeatedly, and worry about the recipient's reaction.

1. Delivering bad news
2. Say no to the request.
3. Responding to complaints
4. Provide constructive feedback.
5. Apologies for the mistake.

These emails are crucial. They test your professionalism. And often, delaying them is more stressful than sending them.

Principle: Directness + Empathy

Difficult emails require two seemingly contradictory things:

 

1. Be direct . Don't hide bad news or add clichés. People will sense when you're avoiding something.
2. Be empathetic . Acknowledge how your message might affect them. Show that you understand their point of view.

Ensure both factors are addressed, not just one.

Delivering bad news

Structure

1. Brief context (1 sentence)
2. Bad news (direct and clear)
3. Acknowledging the impact
4. What will happen next?
5. Suggestion for discussion

Example: The project is delayed.

Poor (slightly concealing bad news):

Hi everyone, I wanted to give you an update on the project. As you know, we've been working hard on the release and the team has put in their best effort. There have been some challenges along the way, and after careful consideration of various factors, as well as discussions with stakeholders, we've determined that we need to adjust the timeline. We will now be targeting Q3 instead of Q2.

 

Better (direct + empathetic):

Hi everyone,

I have bad news: We need to postpone the launch from Q2 to Q3.

I know this will be disappointing – the team has worked hard and it was very difficult to make this decision. The technical issues we discovered last week create too much risk for a Q2 release.

This is the new plan:

1. New target: August 15th
2. Review meeting: Friday, 2 p.m. to discuss adjustments.

I'm happy to discuss any concerns privately. This doesn't overshadow what the team has accomplished.

Example: Job rejection letter

Poor (too general):

Thank you for your interest in this position. After careful consideration, we have decided to select other candidates with more experience and a better fit for our current needs. We wish you success in your future endeavors.

Better:

Hi Sarah,

Thank you for interviewing for the Senior Programmer position. I would like to inform you that we have decided to continue searching for another candidate.

This is a difficult decision – your systems design skills have impressed us. However, we need someone with more specific experience in real-time data paths.

 

We would greatly appreciate your applications for other positions in the future. We look forward to sharing any further specific feedback.

Good luck with your job search.

Say no

Saying no is hard. But vague rejections are even worse—they leave people both hopeful and confused.

Structure

1. Confirm the request
2. Explicit refusal
3. Brief reason (optional)
4. Alternative options, if any.
5. End politely

Example: Declining a meeting

Poor (unclear):

Thank you for contacting me. My schedule is quite busy right now, but I'll see if I have any free time. I'll try to get back to you as soon as possible.

Better:

Thank you for contacting me. I am unable to take any more meetings this quarter – my schedule is already full.

Here are a few alternatives:

1. I'm happy to answer your questions quickly via email.
2. My colleague, Sarah, handles similar partnerships and may have some free time.

Thank you for thinking of me.

Example: Rejecting a request

Poor (excessive apology):

I'm so sorry, but I really can't help you right now. I feel terrible knowing how important this is to you and I really wish I could. It's just that with everything going on, I don't think I can give it enough attention, and I don't want to do a bad job. Again, I'm so sorry.

Better:

I can't take this job right now - current projects are taking up all my time and resources.

Could we reconsider in April? Or, if it's urgent, Jake has done similar work before and might have some free time.

 

I'm sorry, I can't help this time.

Complaint resolution

When someone is upset, refrain from immediately making excuses for yourself.

Structure

1. Acknowledge their experience.
2. Accept responsibility (if appropriate)
3. Briefly explain what happened.
4. Clearly state what you will do to fix it.
5. Prevent similar incidents from happening in the future.

Example: Customer complaint

Poor (defensive):

I'm sorry you feel that way. The delays are indeed due to circumstances beyond our control, and our policy states that shipping times are only estimates. If you've read the terms of service, you'll see that we are not responsible for delays caused by the shipping carrier.

Better:

We understand your frustration – waiting three weeks for an order that normally takes five days to deliver is unacceptable.

I have reviewed this issue: The package was held up at the distribution center due to an address mismatch on our part. This was our fault.

Here's what I'm doing:

1. Send replacement products quickly.
2. Refund shipping fee
3. Add $20 to your account.

I am very sorry that this has happened. Please contact me directly if you have any other issues.

Provide constructive feedback.

Email isn't the ideal way to give detailed feedback—it's easy to misinterpret the tone. But sometimes it's necessary.

Structure

1. Establish a constructive framework.
2. Specific observation (facts, not judgments)
3. Impact of behavior
4. What you want to see instead
5. Suggestion for discussion

Example: Feedback on job quality

Poor (vague and harsh):

The report you submitted wasn't very good. It needs a lot of improvement. Please redo it and try harder next time.

Better:

Thank you for submitting the report on time.

I've noticed a few things that need editing before we can share it with stakeholders:

1. The data in Table 3 does not match the figures in the summary (a difference of approximately $200,000).
2. The summary for the executive board is too detailed - it should only have a maximum of 3-4 bullet points.
3. The methodological section is missing.

 

Can you finalize the revisions before Thursday? I'd be happy to discuss the details further if needed.

Apologize professionally.

A good apology consists of three parts:

1. Acknowledgment – ​​What happened and its impact
2. Take responsibility – No excuses or blame.
3. Troubleshooting – What are you doing to fix it?

Example: Missed the deadline

Poor (full of excuses):

I apologize for missing the deadline. Things have been really busy and I have a lot of other things to do. Also, I didn't realize it would take so long. I will try to send it to you as soon as possible.

Better:

I missed the Friday deadline for the analysis. I apologize – I should have let you know earlier that the work was taking longer than expected.

The complete analysis will be sent to your inbox before 9 AM on Tuesday. If that time doesn't suit your needs, please let me know and I will prioritize processing it in an alternative way.

Next time, I will allow extra time and proactively contact you if any problems arise.

Key points to remember

1. Awkward emails require both honesty and empathy.
2. Don't hide bad news - speak clearly and don't beat around the bush.
3. Say no: Clearly refuse, give a brief reason, and suggest alternatives.
4. Responding to a complaint: Admit first, defend later.
5. Apology: Acknowledgment, taking responsibility, rectification.
6. When in doubt, be polite but clear.

1. Question 1:

   How should you respond to a complaint email?

   1. A. Protect yourself immediately.
   2. B. Acknowledge their frustration, address the issue, and explain the next steps.
   3. C. Ignore them and hope they calm down.
   4. D. Respond in an angry tone like them.

   EXPLAIN:

   An effective complaint response should first acknowledge the person's experience, then address the actual problem and suggest a solution.

2. Question 2:

   What should you include when refusing a request?

   1. A. Just say no without explaining.
   2. B. A lengthy apology and numerous excuses.
   3. C. A clear refusal, a brief reason, and an alternative plan if possible.
   4. D. Completely ignore emails.

   EXPLAIN:

   Effective refusals should be clear (not ambiguous), concise (not overly explanatory), and helpful (suggesting alternatives when possible).

3. Question 3:

   What is the best way to deliver bad news via email?

   1. A. Hide the bad news at the end so they read the good news first.
   2. B. Be direct but empathetic – state clearly but acknowledge the impact.
   3. C. Using a lot of technical jargon to lessen the discomfort.
   4. D. Send it by the end of Friday so they have time to think.

   EXPLAIN:

   Bad news should be stated clearly and promptly. Hiding bad news creates the impression of manipulation. Combining honesty with empathy shows respect for the reader.

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