How to Start a Conversation
You’re Dreading
by PETER BREGMAN
Comments (53) | July 7, 2014
I anticipated that the conversation would be
difficult.
Shari* and I had worked together for many
years, and I knew she was expecting me to hire
her to run a leadership program for one of my
clients, Ganta, a high-tech company. But I
didn’t think Shari was the right fit for Ganta or,
frankly, for the role of running the leadership
training. In fact, I had become increasingly
critical of her recent performance, though I
hadn’t mentioned anything to her about it yet.
That was my first mistake. I should have said
something before it got to this point.
So why didn’t I? I’d love to claim that it was
because I liked her, and I didn’t want to hurt
her feelings. Or because I hoped things would
get better without my intervention.
And while those things were true, there was a
deeper truth: I was afraid of the cringe moment.
Do you know that uneasy moment – right as
you’re saying something that feels risky, but
before the person responds? That’s the cringe
moment.
In other words, I delayed speaking with Shari
because I was afraid of how I would feel giving
her the negative feedback : awkward,
uncomfortable, and maybe even unreasonable.
But I couldn’t avoid it anymore. And because I
had waited so long, the conversation promised
to be even more awkward and uncomfortable.
And now that she was getting a more extreme
message with no warning, I would feel – and
appear – even more unreasonable. The cringe
quotient had gone up.
The day of the difficult conversation, I felt
anxious as Shari came into my office. We
shared a few pleasantries and then I began. I
told her that I knew she wanted to run the
leadership program at Ganta. I talked to her
about the complexities and challenges of the
leadership program and of Ganta in general.
And I spoke with her about my frustrations with
her recent performance. She asked me
questions and I offered explanations and
examples.
I did such a good job avoiding the cringe
moment that, 30 minutes into the conversation,
I still had not clearly communicated to Shari
whether I was firing her or hiring her. My
build-up was equally appropriate as context for
either.
Finally, she did it for me. “So,” she asked, “Are
you saying that you don’t want me to lead this
program or you do?”
Now that I’m aware of it, I see my own behavior
in leaders everywhere. Standing in front of the
room, one senior VP slowly constructed a case
to close a business. But he never got to his
conclusion as people began debating
unimportant details related to his argument
before they even knew where he was headed.
In another case, a CEO sat in a meeting of
department heads with the intention of telling
them she was creating a new position to which
they would all report. But she lost them as she
spent the first 20 minutes giving context to a
decision she hadn’t yet announced. As one
person later told me, “All of the context was
lost on me as I was trying to guess what she
was getting at. It was a complete waste of
time.”
The intellectual reason we build a case, or give
context, to a difficult decision before
announcing it is because we want to convey
that the decision is well-thought out, rational,
and an inevitable conclusion to the facts. But
since the listeners don’t know what decision is
being made, they have no context for the
context and it all feels meaningless.
The emotional reason we give such long
introductions to hard decisions is because we
are procrastinating. We’re delaying the cringe
feeling.
But this delay is counterproductive; it only
stretches and deepens the discomfort of
everyone involved.
The solution is simple and straightforward:
Lead with the punchline.
What should I have said to Shari? “Thanks for
coming in, Shari. I am not going to have you
run the leadership program with Ganta, and I’d
like you to understand why . . . ”
The senior VP should have started by saying, “I
have come to the conclusion that we should
close XXX business.”
And the CEO should have opened her meeting
with the department heads by declaring “I have
created a new Senior Vice President role,
reporting to me, who will oversee this part of
the business.”
After those openings, people will be interested
in hearing the rest. Or, they may surprise you
with instant agreement and there may be little
more to discuss.
Here’s what I’ve come to realize: I almost
always overestimate how difficult it is for the
other person to hear what I have to say. People
are resilient. I’m usually more uncomfortable
delivering a difficult message than the other
person is receiving it.
Next time you have a conversation you’re
dreading, lead with the part you’re dreading.
Get to the conclusion in the first sentence.
Cringe fast and cringe early. It’s a simple move
that few of us make consistently because it
requires emotional courage. At least the first
time.
But the more you do it, the easier and more
natural it becomes. Being direct and upfront
does not mean being callous or unnecessarily
harsh. In fact, it’s the opposite; done with care,
being direct is far more considerate.
And it doesn’t just reduce angst, it saves time
as well. Shari wasn’t happy about not running
the program at Ganta, but she understood why
and accepted the decision quickly. Much more
quickly than it took me to introduce it to her.
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