Tough Conversations

The Hardest Part of My Job…

The hardest part of my job as a manager is having tough conversations. One might even say, this is the toughest part of life. Because no one likes to break up with someone else, or hurt another’s feelings, or even sit in awkward silence. In fact, I’m going to wager that most of us dread this kind of talk.

What’s a “Tough” Conversation?

A “tough” conversation can refer to the simplest of things — like giving creative feedback or calling someone out for being late — to the most complex — like giving a negative review or firing someone.

Those in-between conversations are all about accountability. These are the easiest to lose track of or forget because they seem so small… until accountability is lost and a big problem is introduced.

I think it boils down to those three types of tough conversations: feedback, accountability, and separating.  But the two book-ending categories of feedback and splitting up are probably the toughest conversations to initiate. I know from experience.

giving feedback cropped

How to Give Feedback (some good rules to follow)

Always have a tough conversation in person, face-to-face, or (if your team is remote) do a video call. It’s very important for you to see your team member and for them to see you. This will allow you to read their emotions, allowing you to identify and respect their feelings. It also allows you both to address concerns because you’ll both be able to see body language that might contradict a verbal agreement.

I recommend starting by asking permission to start a conversation. You want both parties to walk in with the available time and headspace. Try something like “I have some feedback, is now a good time?” to get permission to begin.

I also recommend sharing your intention upfront. We naturally make assumptions about people’s intentions and you will never know what they are unless you flat out explain them or ask about them. It removes the guesswork and makes things very clear.

Here are a couple of examples for starting a tough talk (after you have permission):

  • I have some difficult feedback to share; I need you to know that I’m coming from a place of love and respect…
  • What I’m about to share is a little difficult, so please bear with me as I explain where I’m coming from…
  • I know we can’t always control our emotions easily, but please try to hear what I’m about to say with an open mind…

Sometimes, stating the obvious is the best way to prepare someone to hear what you need to share.

And if you’re worried about micromanaging or being overbearing, check out our article about Dialing Down the Control Freak.

Not About Blame, But All About Moving Forward

We’re never really taught how to have a difficult conversation. Most of us learn from how our families interact with each other. Whatever their techniques in dealing with conflict and resolving problems are, they’re passed down from generation to generation.

While I’m sure there are folks out there who are naturally amazing at these conversations, most of us just don’t know how to do it, and so the end result is to blame, which puts the receiver on the defensive. A conversation like this is never productive.

Always approach a difficult conversation with the intention of making things better for both parties going forward. This is the single most important step in starting a tough conversation. This means that either you or the other party are taking responsibility and owning what happened, not assigning blame.

What’s the difference between responsibility and blame? Blame is assigning fault or wrongdoing to someone. Responsibility is assigning control over a task or job.

You both want to acknowledge what happened, how it affected everyone involved, and what you can do to prevent it from happening again in the future so that you can avoid being hurt again. This is assigning responsibility, not blame.

My high school teacher, Ms. Kozak, taught me this formula way back in the teenage years:

“When you do [insert action or words] it makes me feel [insert emotion words]; how can we make it better going forward?”

This is a fantastic way to show how an action that probably wasn’t intended to hurt you, actually did hurt you, and that you don’t want to be hurt anymore.

We can’t help the way we feel, but we can help how we respond to our feelings and what we do with them. You’re not blaming the person for doing it, you’re just sharing how it made you feel. Most of us don’t want to hurt each other, so we’ll work on a better solution for the next time this scenario comes up.

Catching Defensiveness and Redirecting It

Because we are so used to the blame game, many of us enter a difficult conversation already on the defensive. Sometimes we bring in another topic to sidetrack the conversation or derail it or shift the blame. Again, not very productive.

In this case, I would say, “I’m not trying to blame you, I’m trying to discuss what happened so we can move past it and learn how to avoid it in the future. We can tackle your other issue at another time, let’s revisit it tomorrow.”

When to Do it Face to Face

Always…almost. Most difficult conversations or feedback should be had face-to-face. Do this whenever you can, because it will be better for everyone involved.

Although writing an email or sending a letter may feel like a safer option, it can likely create more issues. A live conversation happening face-to-face allows both parties to be present and responsive, which is the most effective way to find a solution and avoid the problem going forward.

When to Do it in Writing

I believe that when you have a solid relationship in place, some lighter feedback can be given in writing, but everyone is different, so it’s important to assess what you know about the team member you’re communicating with. Here at Smack Happy Design, we’ve created user manuals for our team members that outline exactly how we each like to communicate. Now, we can refer to it anytime we need to share feedback.

Download the user manual template

View the completed user manual example

But you can take a dual approach as well. For example, when I’m working with a sensitive person, I give feedback in-person no matter the feedback type and then follow up with a summary in writing. This ensures that the initial impact of the feedback I’m sharing is taken how I meant it and we have a chance to discuss any lingering emotions. Writing carries no emotion or intention, so it is very easy for the reader to insert whatever feelings or insecurities they imagine, often projecting their own feelings into your words and changing the meaning entirely in the process.

4 Feedback Techniques

To help make sure you’re prepared going forward we created this handy list outlining four different feedback techniques. Download the tips.


Giving Feedback to a Teammate vs a Client

There are two common scenarios where you might be giving a client some feedback. One, you may think what they’re asking for is wrong and you want to suggest a better way. Or, two, perhaps you don’t like the way they’re treating you or the team, so you need to address something about the way you’re communicating with one another.

If we’re talking about the latter, then I would use one of the methods listed above. If we’re talking about the former, here’s how I would handle it:

  • Address what they’re asking for and make sure you understand.
  • Think about what they want to achieve rather than how they want to achieve it.
  • Confirm what they want to achieve.
  • Now suggest your alternatives for getting the same results.
  • Make sure you acknowledge their idea and its merit, explain why your idea might be better.

Paraphrasing and rephrasing is a great way to achieve each of the steps. The client may or may not accept your idea in the end, but at least you tried!

client feedback cropped

How to Fire Someone (some good rules to follow)

The hardest thing I’ve ever had to do was let one of my employees go. Let’s first take a moment to acknowledge the fact that firing someone is hard. Really, really hard. You know it’s going to ruin their day, and as a result, it ruins your day.

The first time you have to fire someone, you’ll be nervous. I was sweating my butt off with nervousness the first time. But keep telling yourself, “you got this, you can do it.” The decision is rarely easy and neither is the delivery. But there are some things you can do to make the delivery go a little smoother.

When to Do it Face-to-Face

When you need to fire someone, separate, or part ways with a teammate, you absolutely must do it face-to-face. Just like giving feedback, this needs to be a live conversation where both parties can read the body language of the other. My heart was pounding so hard the first I did it, and that nervousness doesn’t ever really go away.

When to Do it in Writing

Please note that some states have laws around firing employees. Be sure to check the process in your region and consult your company policies. You might have to go through an improvement program or show (through documentation) that you tried to correct the issues before letting someone go. Consult an HR person or business attorney to do it the right way, and if they recommend conducting the firing (in whole or part) in writing, that’s the only time you should do so. Following the law is the easy part, the talk is the hard part!

How to Fire Someone For the First Time

First, take some deep breaths. Literally, just sit and breathe for a while. Remember why you’re letting this person go. Write those reasons down and read them to yourself a few times, because you’re going to need to stick to your guns.

People will respond in different ways, here are two of the most popular responses.

The Emotional Response

The employee may start crying. This is a reality to prepare yourself for in advance. This might be light tears or downright sobs. Next, they may start blaming and trying everything in their power to turn your decision around. They may even try to manipulate you.

This is where it’s really important to both be empathetic but also hold your ground. Keep remembering: you’re letting them go for a reason, but this is hard for them to hear.

I’ve experienced what it’s like keeping an employee after an emotional response. The employee promised to improve on the issues we were experiencing, but they continued to create the same issues and did not put in a good-faith effort to improve. Unfortunately, it became very awkward for both of us. This situation is not worth having to have a difficult conversation where you have to let them go for a second time.

Your response to an emotional response will vary based on what you know about the person you’re firing. You’ll need to read their body cues, which is why doing this face-to-face is so important. You shouldn’t feel compelled to apologize, but if you feel it’s appropriate to express disappointment or regret, then you can say something honest yet upbeat like “I wish this wasn’t the case, but I believe this is for the best.”

The Apathetic Response

As if its opposites day, the other most popular reaction you might receive is nothing at all. It could be easy as pie. They may not say anything and just accept their new fate. This often happens with employees who already see it coming and therefore understand why they’re being let go, so there is no surprise at all.

Letting a contractor go often results in an apathetic response and can be much easier than letting an employee go, depending on your agreement with the contractor. Again, from a legal standpoint, it’s important to double-check your agreement, document everything, and make sure you’re respecting the terms of your contract together.

Not About Emotions, Just Keep it Professional

When you do let someone go, even if you have a personal acquaintanceship with them, keep it professional. You want to balance between avoiding emotions while remaining kind and empathic.

Remember: this isn’t personal, you’re doing it for the business. You may really like them as a person, but friends don’t drive your business forward. State the situation and keep it really short and simple.

Here is an example of a language I’ve used before:

“Unfortunately, I have some bad news to share. [I’ve run the numbers and I have to cut back on expenses, which means I have to let you go. (insert your reason here)] I wish this wasn’t the case, but I believe this is for the best. I’m happy to give you a letter of recommendation, and I wish you the best with future endeavors.”

They may ask you why. They may ask for feedback. They may be in disbelief. Whatever the reaction, stick to your reason.

In fact, the moment you start giving feedback you dive into the rabbit hole. Avoid the rabbit hole! You might also want to use an example of a time in your past where you made a mistake and it changed your life. Here is a fictional example.

“I know it doesn’t seem like it now, but this can really jostle you to dig deep about your career. If I hadn’t have been let go from my corporate job, I wouldn’t have started this agency that I now love so much.”

Ways this can be good for their career:

  1. Helps to get clear on their goals. Thinking about what they’ve lost, and what they want out of their next career move.
  2. Reminds them of their own resources they can tap into – like their ability to believe in themselves.
  3. It is a relief to not have to settle back into the job that wasn’t the best fit for the day after day.
  4. Emphasizes the fact that they are in control of their self-image. It is their choice now to decide to move forward and not feel bad about themselves.
  5. Allows them the time to research and decide what is next, revamp their resume, and choose the job positions they truly feel excited about and apply.

Examples like this may help them see that this isn’t just an end, but also the beginning of the next chapter in their life.

In Conclusion

Having a difficult conversation with a teammate can be tough, but when you come prepared and practice compassion and empathy, you’ll build a stronger relationship over time.

Always ask if its a good time for feedback, set your intentions first, avoid blame, leave the emotions out of it, and follow up later on with something unrelated to reaffirm the fact that even though it may feel personal, that (in fact) your decision to let them go is not personal at all.

4 Feedback Techniques

To help make sure you’re prepared going forward we created this handy list outlining four different feedback techniques.


1 Comment

  1. FINN Construction on June 25, 2019 at 6:54 am

    Good article. Professionalism should not be involved with emotional feelings.

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