Workbook

Manager Essentials:
Having Difficult
Conversations
Does the idea of confrontation, conflict, or constructive criticism
send you running in the other direction? It’s a natural reaction.
According to Harvard Business Review, 37% of managers said
they’re uncomfortable giving direct feedback about their employees’
performance if they think the employee is likely to respond negatively.
But ignoring sticky situations doesn’t make them go away. In fact,
by avoiding difficult topics, we actually give them more power.
“I’ve learned that we tend to build these conversations up in our
minds. They take on an outsize role in our thoughts, causing us to
ruminate and stress outside of work,” writes Udemy instructor and
communication coach Andrea Wedell.
Learning to navigate difficult conversations is a critical skill for
managers. After all, it’s one key to helping employees grow and
improve. And it all starts with remembering that conversations go two
ways. When you bring a coaching mindset, listen actively, and ask for
the other person’s interpretation and takeaways, you ensure that both
parties feel seen and heard.
This workbook will help you develop the confidence and clarity you
need to handle difficult conversations.
5 ways to prepare
for difficult conversations
Getting comfortable with difficult conversations is critical to your success as a
manager. There’s also a bonus to developing this skill: It can help you in other
areas of your life. Once you learn these tactics, you can apply them in many
situations. Follow these prompts to plan and prepare for difficult conversations.

1.
Understand when a difficult
conversation is needed
How do you know when it’s time to have a difficult conversation? One
clear sign is if you spend a lot of time thinking about an issue or recurring
theme, especially if you are thinking about it repeatedly outside of work.
Recognizing this phenomenon when it occurs is a skill in and of itself.

Is there a topic (or topics) you need to discuss with someone on your team,
but you’ve been putting it off because you consider it difficult? If this isn’t
currently the case, can you think back to a time when it was?

Consider how much time and energy you are focusing on this
challenging situation. How could you be using those resource instead?

Manager Essentials: Having Difficult Conversations 2

2.
Work through anxiety or fears
The reason we consider some conversations “difficult” is because they bring
up fear or anxiety. Knowing that your feelings are common can help remove
some of the apprehension. These prompts will help you recognize and
reframe common fears and worries.

Consider why this particular conversation is a trigger for you.

Is it because of the person you need to speak to, the reaction you
anticipate, the subject matter of the conversation, or something else?

Challenge your fear by questioning it. Answer these questions:

• Is the fear keeping you from having the conversation?

• Are you imagining outcomes of the conversation based on fear or anxiety?
Is that fear helping you prepare or holding you back?
• Do you feel unsure about what you want to say?
• Does your mind race to “what if” scenarios? How likely is it that those
outcomes will actually come to be?
• Are you convincing yourself you can’t handle the conversation?
Is that true?

Manager Essentials: Having Difficult Conversations 3

3.
Know the person you’re talking to
If you want to increase the chances that the other person will hear what
you have to say, it’s important to think about who they are. Don’t just focus
on what you want to tell them — consider their position and perspective.
When you understand their specific needs and priorities, you can frame
your message more effectively.

Who is the person you need to have a difficult conversation with?

What are their needs and priorities?

Consider how you can frame your message in terms most likely to resonate
with this person. For example, if they care about career advancement,
can you connect the conversation to that goal?

Manager Essentials: Having Difficult Conversations 4

4.
Practice assertiveness
Assertiveness is a communication style that’s especially helpful during
difficult conversations. It involves a balance of speaking clearly while
delivering your message in a way the other person can hear. But it might
take a little practice to feel comfortable being assertive, especially if
your default communication style is more passive (people-pleasing)
or aggressive (blunt and direct). These prompts will help you practice
communicating assertively.

Distill your message down to the bottom line. What do you want to say in clear
and concise terms?

Being assertive means staying rooted in facts. What evidence and examples
do you have to support your message?

Manager Essentials: Having Difficult Conversations 5

5.
Deliver the message effectively
When it comes time to have the conversation, it’s not just about the words
you use, but your body language and tone of voice. You’re much more likely
to deliver your message effectively when you focus on all of these elements.

Write out what you would like to say during the conversation, including your
bottom line message and any evidence or examples you want to mention.

Practice saying your message out loud until you feel comfortable, confident,
and grounded. Consider your body language and tone of voice to ensure
you’re clear and firm.

Manager Essentials: Having Difficult Conversations 6

Help other leaders
develop critical
communication skills
It takes practice to get comfortable with the skills we’ve covered
in this workbook, but the effort is worth it. “When we make the
commitment to engage in these difficult conversations, we have
the ability to move forward, both in the specific situation and in
our careers in general,” says communication coach and Udemy
instructor Andrea Wedell.
Because conversations are a two-way street, you might find it
helpful to imagine different outcomes and how you’d respond. For
example, if your team member is silent, you can give them time
to process before asking if they understood your message. Or if
someone gets upset, that’s a good sign that it’s time to take a break
and return to the conversation later. Don’t be afraid to talk to other
managers and learn how they would handle different scenarios.
Want to help your team and other leaders in your organization
develop confidence with critical communication skills? Learn how
Udemy Business can support your leadership training needs.

Manager Essentials: Having Difficult Conversations 7

About Udemy Business
Udemy’s mission is to improve lives through learning by providing flexible,
effective skill development to empower organizations and individuals.
Udemy Business enables employers to offer on-demand learning for all
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we equip companies with the tools to build a future-ready workforce,
increase employee engagement, and achieve critical business outcomes.
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