Effective Confrontation Emails


When working with contractors or freelancers there are bound to be some confrontation emails coming. Working with freelancers is different from managing regular workers in an office. How you send those confrontation emails to resolve issues is also very different.

Communication issues are common, largely because email tends to be relied upon when dealing with remote workers. It might be that they are some distance away, or even in another country, and perhaps don’t have the same working hours as you. So while email is fine for day-to-day communication, the situation gets a bit more complicated if a problem arises. That’s when you find yourself having to send one of those awkward confrontation emails asking what’s going on, or why they haven’t met your deadline.

Emails are easily misconstrued, misread and the content can be very easily misunderstood. When it’s a confrontation emails, every word can be taken to heart by the recipient so it’s an area which needs to be handled with care.

We all know what happens when hasty confrontation emails are fired off to people in anger – it never works out well! So if you need to speak to a contractor and email is your main communication tool, make sure you use these five steps to help you write in a way which starts a conversation rather than ignites a confrontation.

Five Steps for Crafting an Awkward Email

1.  Use Very Straightforward Language

With a situation like this, you are trying to avoid making things worse. Start a conversation in your confrontation emails about where there might be a problem, and then see if you can find a solution. Make your email really straightforward and be very specific about what the issues are.

Avoid humor or being overly familiar when you write confrontation emails as this can come across as false. You want to find out what is causing the problems so lay out what has happened,  and ask them to let you know why the issues have occurred and how you can help them resolve them.

It may be that there are personal circumstances going on which have caused them to miss your deadline. As they are remote from you there won’t be that rapport and personal interaction which you get with colleagues next to you in an office. Tread carefully, certainly initially, until you have the whole story.

It’s important not to judge in confrontation emails. Just explain the issue in a very straightforward way and try to move it to a phone call or meeting where possible as problems are always best dealt with using more direct human interaction where you can have a decent conversation.

Keep your confrontation emails short and to the point. Don’t assign blame or comment on reasons why you think this happened. Just explain the issue, which might be a missed deadline, or below quality work, and say you’d like to discuss it further. If you need some help and guidance to improve your writing, check out Writing Populist and Boomessays.

2.  Start Confrontation Emails with Praise

People respond well to praise and don’t like being told off. It can often feel like all their great work goes unnoticed whereas one minor setback gets picked up instantly. This is not a great way for people to end up feeling, particularly if they work far away as they will end up feeling resentful.

So, you could open your confrontation emails with something like, “You have always been very diligent in meeting all of our deadlines up to now, which we really appreciate. We were concerned about you when you missed the last one. Is there anything we can do to help?”

“It needs to be genuine and not come across as patronising so choose the wording carefully and take your time – the aim is to craft an email which expresses concern and a wish to resolve things, not blame and anger”, – explains George Crow, a Communication Manager at Revieweal and Huffingtonpost writer.

3.  Explain the Issues Without Assigning Blame

It’s really important not to blame a contractor or freelancer in confrontation emails, particularly before you know all the facts. Just explain what happened and say you like to discuss the issue with them to find a way to move forward.

If you start talking about how what they did has disappointed you and caused lots of problems for you and why didn’t they call you to let you know, it becomes a blame game and an argument which will only leave both parties feeling resentful.

Take a step back from what happened and just explain your concerns without expressing your own thoughts or opinions. If appropriate, that can come later on, for example, if they don’t take the issue seriously.

Once you have drafted your confrontation emails, get someone else to read through them each time to make sure they are not coming across in a harsh or negative way. Or you can try using the Assignment help online email editing tool which was recommended with some others in this HuffPost article.

4.  Don’t Write in Anger and Always Offer to Talk

When something happens, particularly if the other person isn’t there to immediately talk to, anger and resentment can build up and it is all too easy to fire off confrontation emails in anger and in haste.

We have no doubt all been on the receiving end of confrontation emails like that from a manager. When people are working remotely and not side by side in an office, it can be even worse. They can’t say, “Oh, he is a nice person normally, he will be fine when he calms down.” The recipient might never have met the sender in this type of situation.

Always wait before you send confrontation emails. Craft them carefully, following the points above. Another important aspect to any email about a potentially confrontational issue is to always suggest a talk. Otherwise, there is the danger of emails flying back and forth but no actual progress being made.

Make sure your subject line isn’t too aggressive either – make it generic and not something intimidating like – re: the mistakes you’ve been making, or re: there is a real problem here. Try Lets go and Learn, which features a blog for email subject ideas if you are stuck. Or you could have a look at Uktopwriters for even more writing tips and hints.

End your email with an offer to jump on a call or catch up on Skype to talk it all through. Whenever possible, suggest meeting for a coffee to discuss a way forward to make everyone’s lives easier.

5.  Have a Plan in Place for the Response

The other thing to bear in mind when you do press send is what kind of response you want to get from the other person, if you get one at all. It’s good to have a plan in place for what to do next, so if they don’t reply to your confrontation emails or take up the offer of a call within a few days, what happens?

Think about what course of action would be appropriate if they come back to you in an aggressive manner, or if they decide to go over your head to complain about what you have said. These and more are real possibilities.

Make sure that confrontation emails don’t turn work into an email war zone with rude replies going back and forth. That won’t be good for anyone. If they are a freelancer or contractor, depending what type of agreement you have made with them, you should also be prepared for what happens if they just walk away from the work.

When to Consider Not Using Email 

If you are confronting someone, email really should only be the last resort and should always include the opportunity to have a call to talk it through.

If someone has acted out of character then try reaching out to them by telephone or video conference. It might be that something very personal has happened which you don’t know about and they wouldn’t want to share with you on email.

Bradley Crisman, a Recruiting Professional and Internal Communication Manager at Dissertation service comments: “They may have missed submitting your work that week because they have been in hospital, or looking after a sick relative, for example. Always bear in mind that a remote worker has their own life too and it might not be anything to do with you that has created the problem.”

Certainly don’t use confrontation emails for major decisions like if you are planning to let someone go. They can be used to send a reminder message, if they’ve ignored phone messages and are still failing to perform. Life-changing decisions like losing a project, however, should always be done face-to-face, however uncomfortable that may be.

Summary and Conclusion

Communicating with contractors and freelancers via email does need more care and thought than perhaps firing off to a colleague in the room next to you, who can then run in and ask you questions. Remember that contractors and freelancers might never have met you, don’t know your humor or style and will take your confrontation email at face value.

Whenever you need to raise a potentially confrontational or negative issue, always try to do it by phone first, but if that doesn’t work, use the five tips and the tools outlined here to make sure your email hits the right note and helps to get the relationship back on track.


Freddie Tubbs


Freddie Tubbs is a internal communications manager at Resumention. He is a senior writer and editor at Academadvisor blog and is a columnist at the Atlantic andOxessays blog.



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