Difficult Emails

The Emails You Dread

In the previous lesson, we explored tone and voice. Now let’s build on that foundation. Some emails are hard to write. You procrastinate. You draft and redraft. You worry about how they’ll react.

• Delivering bad news
• Saying no to a request
• Responding to complaints
• Giving critical feedback
• Apologizing for mistakes

These emails matter. They test your professionalism. And they’re usually more stressful to delay than to send.

Principle: Direct + Empathetic

Difficult emails require two things that seem contradictory:

Be direct. Don’t bury bad news or pad it with fluff. People sense when you’re avoiding something.

Be empathetic. Acknowledge how your message might affect them. Show you understand their perspective.

Both. Not one or the other.

Delivering Bad News

The Structure

1. Brief context (1 sentence)
2. The bad news (direct, clear)
3. Acknowledgment of impact
4. What happens next
5. Offer to discuss

Example: Project Delay

Weak (buried bad news):

Hi team, I wanted to update you on the project. As you know, we’ve been working hard on the release and the team has put in incredible effort. There have been some challenges along the way, and after careful consideration of various factors and discussions with stakeholders, we’ve determined that the timeline needs to be adjusted. We’ll now be targeting Q3 instead of Q2.

Better (direct + empathetic):

Hi team,

I have difficult news: we need to push the launch from Q2 to Q3.

I know this is disappointing—the team has worked hard and I don’t take this decision lightly. The technical issues we uncovered last week create too much risk for a Q2 release.

Here’s the new plan:

• New target: August 15th
• Review meeting: Friday 2pm to discuss adjustments

Happy to discuss concerns one-on-one. This doesn’t diminish what the team has accomplished.

Example: Job Rejection

Weak (too vague):

Thank you for your interest in the position. After careful consideration, we have decided to move forward with other candidates whose experience more closely aligns with our current needs. We wish you well in your future endeavors.

Better:

Hi Sarah,

Thank you for interviewing for the Senior Developer role. I wanted to let you know we’ve decided to move forward with another candidate.

This was a close decision—your system design skills impressed us. Ultimately, we chose someone with more specific experience in real-time data pipelines.

I’d encourage you to apply for future roles. If it’s helpful, I’m happy to share more specific feedback.

Best of luck with your search.

Saying No

Saying no is hard. But unclear declines are worse—they leave people hoping or confused.

The Structure

1. Acknowledge the request
2. Clear decline
3. Brief reason (optional)
4. Alternative if available
5. Warm close

Example: Declining a Meeting

Weak (unclear):

Thanks for reaching out. My schedule is pretty packed right now but let me see if something opens up. I’ll try to get back to you.

Better:

Thanks for reaching out. I can’t take on new meetings this quarter—my schedule is at capacity.

A few alternatives:

• I’m happy to answer quick questions over email
• My colleague Sarah handles similar partnerships and might be available

Appreciate you thinking of me.

Example: Declining a Request

Weak (over-apologizing):

I’m so sorry, but I really can’t help with this right now. I feel terrible because I know 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’d be able to give it the attention it deserves, and I wouldn’t want to do a bad job. I’m so sorry again.

Quick check: Before moving on, can you recall the key concept we just covered? Try to explain it in your own words before continuing.

Better:

I can’t take this on right now—my current projects are consuming all my bandwidth.

Could we revisit in April? Or if urgent, Jake has done similar work and might be available.

Sorry I can’t help this time.

Responding to Complaints

When someone is upset, resist the urge to defend yourself immediately.

The Structure

1. Acknowledge their experience
2. Take responsibility (if appropriate)
3. Explain what happened (briefly)
4. State what you’ll do to fix it
5. Prevent future occurrences

Example: Customer Complaint

Weak (defensive):

I’m sorry you feel that way. The delay was actually due to circumstances beyond our control, and our policy clearly states that shipping times are estimates. If you had read the terms of service, you would have seen that we’re not responsible for carrier delays.

Better:

You’re right to be frustrated—waiting 3 weeks for a 5-day delivery is not acceptable.

I’ve looked into this: the package was held at a distribution center due to an address mismatch on our end. That’s our mistake.

Here’s what I’m doing:

• Expediting a replacement via overnight shipping
• Refunding your shipping cost
• Adding a $20 credit to your account

I’m sorry this happened. Please reach out directly if you have any other issues.

Giving Critical Feedback

Email isn’t ideal for detailed feedback—too easy to misread tone. But sometimes it’s necessary.

The Structure

1. Set a constructive frame
2. Specific observation (fact, not judgment)
3. Impact of the behavior
4. What you’d like to see instead
5. Offer to discuss

Example: Feedback on Work Quality

Weak (vague and harsh):

The report you sent wasn’t very good. It needs a lot of work. Please redo it and try harder next time.

Better:

Thanks for getting the report in by the deadline.

I noticed a few areas that need revision before we can share with stakeholders:

• The data in Table 3 doesn’t match the numbers in the summary (off by ~$200K)
• The executive summary is quite detailed—aim for 3-4 bullet points max
• The methodology section is missing

Can you have a revised version by Thursday? Happy to walk through these in more detail if helpful.

Apologizing Professionally

Good apologies have three parts:

1. Acknowledge – What happened and its impact
2. Take responsibility – No excuses or blame-shifting
3. Repair – What you’re doing to fix it

Example: Missed Deadline

Weak (excuse-laden):

I’m sorry I missed the deadline. Things have been really crazy and I had a bunch of other stuff going on. Plus I didn’t realize how much work it would take. I’ll try to get it to you soon.

Better:

I missed the Friday deadline for the analysis. I apologize—I should have flagged earlier that it was taking longer than expected.

The completed analysis will be in your inbox by Tuesday 9am. If that doesn’t work for your needs, let me know and I’ll prioritize it differently.

I’ll build in more buffer next time and communicate proactively if things slip.

Key Takeaways

• Difficult emails require both directness and empathy
• Don’t bury bad news—state it early and clearly
• Saying no: clear decline, brief reason, offer alternatives
• Responding to complaints: acknowledge first, defend second
• Apologies: acknowledge, take responsibility, repair
• When in doubt, be kind but clear

Next: follow-ups that get responses without being annoying.

Up next: In the next lesson, we’ll dive into Follow-Ups That Work.