How to have difficult conversations

by Rajiv Jayarajah
Business Growth Coach
HOW TO HAVEDIFFICULT CONVERSATIONS
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Having that difficult conversation can be the one thing many of us dread at work.
In fact, a survey of 2,000 workers found, *57% of respondents said they would do
almost anything to avoid a difficult conversation; and 52% said that they would rather
put up with a negative situation at work than having to talk about it.
(*Chartered Management Institute, July 2015).
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The Elephant in the room,
the hard chat, the “I will
deal with that later”.

3
Here are my TOP 7 TIPS for getting
through difficult conversations, keeping
your relationships intact and achieving
positive outcomes from them.
Due to this, many people fear them and ultimately avoid conducting
them, which can mean the situation continues to worsen.
Moreover, as a leader, it is often expected that
you know how to have these confronting conversations.
So what if you have never done this before?
Where do you begin and how do you make sure it is done
in a respectful and timely manner?
Throughout my career, I have had to have difficult conversations regarding poor
performance, inappropriate and negative behaviour and redundancies.
These discussions have the potential to become emotional and unpredictable and
may leave you vulnerable and open to criticism.

Neal Creative ©
1. SAVE THE
SURPRISES FOR
BIRTHDAY PARTIES

Don’t invite them for “a coffee and a chat”, leaving them
blindsided once the session has commenced.
In my corporate life, I was once asked by my manager to have a
coffee catch up. I turned up, and my manager and HR also
turned up and went on to explain that due to a restructure my
role would be changing, and my team size and accountabilities
were increasing.
As Benjamin Franklin
famously said,
“honesty is the best
policy”.
A far more appropriate approach would have been to explain
the meeting purpose upfront, give me time to prepare myself
mentally and then have a far more constructive discussion
around the change in the situation.
5
Let the person in question
know from the outset
the purpose of the meeting.

Neal Creative ©
2. YOUR PLACE
OR MINE?

For example, sitting in your
office, behind your desk, or
in the open-plan kitchen,
may not be conducive to
open and honest rapport.
Conversely, taking someone
to public, noisy café to “have
the conversation away from
work” probably won’t work.
Plus the free cappuccino
may not make up for
the difficult chat.
Instead, opt for a private
meeting room which is
booked in advance.
Also book the meeting room
for longer than required, so
that the person receiving the
news has time to digest
things in private.
If you think the meeting
may become emotional,
be prepared with tissues
and water.
xxxxx
Depending on what you need to
communicate, you want to ensure the
environment and timings are right.
7

Neal Creative ©
3. TIMING IS
EVERYTHING

TIMING IS CRITICAL.
If you notice something is not going
well then be upfront and call it early.
For example, “I saw you missed the last two deadlines. Let’s get together tomorrow
and work through this. ” This will be far more effective than sharing this thought nine
months later at the end of year performance review.
By acting quickly, you are giving your team member the best chance at correcting
performance and getting back on track.
Also have the conversation as soon as possible.
Don’t schedule the meeting for later in the week and let people
stress about the conversation.
Ideally, have these conversations first thing in the morning and then if required
give your team member time to reflect and digest what has been discussed.
Your role as a leader is to leverage timely feedback
to drive improved performance, not punish people
!

Neal Creative ©
4. WHEN YOU
ASSUME…

Before you meet with
your team member,
establish exactly why
the meeting is
occurring and what you
expect the meeting
outcome to be.
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Depending on the
complexity of the
conversation, discuss
the approach with
your manager and an
HR rep.
Do your research
beforehand and ensure
your facts are correct.
Don’t assume anything
and never let yours (or
other’s) opinions cloud
the situation.
By not assuming, this
will enable you to
answer your team
members questions
rather than “I will get
back to you on that
one” or “we need to
continue this at a
later date”.
These are not an ideal
responses if your team
member is upset or
anxious.
If it is a fact-finding
meeting, be impartial
and open to all manner
of information your
staff member gives
you.
…YOU MAKE AN ASS OUT OF
YOU AND ME…

Neal Creative ©
5. SMALL TALK
SUCKS

…and don’t evade a difficult conversation by spending
the first 10 minutes making small talk.
Lay it bare and remain sensitive
and compassionate,
acknowledging that they are
probably feeling anxious.
Save the
small talk
for your
backyard BBQ
Once you have provided
context on the issue, it is
important not to rush your
team member’s response or
their understanding.
Give them time to digest the
matter.
Remember you have had
more time to deliberate on this
issue and now it is their turn.
Let them ask questions.
Let them have their say.
Work through their problems
and concerns with them.
Try and make it as
constructive an exchange as
possible.
You want to preserve the
relationship.

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Some meetings may become emotional which can be challenging.
That is, make sure you go
into the conversation with a
clear mindset and with your
emotions in check.
GIVE YOURSELF A CHECK-UP FROM THE NECK UP
Always allow them their dignity and due respect
but keep the meeting on track.
Acknowledge emotions such as sarcasm, defensiveness,
anger. Allow your team member to work through this,
however, never respond in the same way.

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Don’t have the meeting and then
pretend it never happened
Never intentionally avoid that
person.
A friend once worked for a CEO who
had to make several senior staff
redundant.
Once it happened, they then avoided
them for the remaining four weeks
they were in the company.
They felt humiliated, isolated, and
took it very personally.
If there needs to be a follow-up conversation, make sure
it occurs
If you need to check in on your team members
welfare, make sure you do
If they need to provide anything to you, make sure
they do so
It is about achieving the predetermined outcomes and
rectifying the issue that existed.

“
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These are just a few insights into
how to manage difficult conversations
and to achieve positive outcomes from them.
Website our website to learn more
www.bareinc.com.au

“
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ABOUT THE AUTHOR:
Rajiv Jayarajah is the Founder of Bare Inc., a consulting and professional
coaching firm specialising in creating clarity for business owners and
leaders so that they can achieve their goals faster.
It’s easy to connect. Find me on
LinkedIn | Instagram | @bare_coach | www.bareinc.com.au

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