Upshots: Telling Your Best Story with Courtney Kaplan

If it doesn't already come naturally, communicating about your work can feel uncomfortable and downright cringey. But like it or not, it's part of the job. What you need is a method and a motivator, and fortunately Courtney Kaplan returns to Upshots to be just that! In this episode, Courtney offers a structured approach to not just build cold case studies but real stories that connect with hearts and minds. You'll also gain practical tips for gathering testimonials and overcoming the discomfort of self-promotion. This episode is brimming with actionable advice to help you effectively represent yourself in any professional setting!

"Own your part of it, own the strengths of the conversations you brought to the solution, and be bold and braggy. If you have a hard time being bold and braggy, you can turn up the volume to 11 and you're still probably only hitting a five or six." - Courtney Kaplan

Free PDF guide @ https://bit.ly/upshotskaplan2

Connect with Courtney on LinkedIn or check out her courses, worksheets, and coaching offerings at iconicleadershipcoaching.com. 

Follow Unserious in your podcast app, at unserious.com, and on Instagram and Threads at @unserious.fun.

Episode Transcript

Speaker 2 (00:19):
This is Unserious, using right away.
Our guest today is CourtneyKaplan, coach, writer and
founder at Iconic LeadershipCoaching, helping people
reinvent themselves and createlives that matter.
Welcome back again, Courtney.
What are we learning abouttoday?

Speaker 1 (00:34):
I'm so happy to be here with you, micah.
Today we are learning aboutcommunicating about yourself.

Speaker 2 (00:39):
You mean the shadow job that we have in addition to
our regular job.

Speaker 1 (00:43):
That's beautifully said, because I think it's true.
It's quite true.
You know, these days, not manyof us stay in one job, so we
need to be able to representourselves in our work over time.
So how do you own your storyand talk to your successes?
Easily?
This is also for folks who areworking hard and getting good

(01:06):
results.
But you might be seeing otherpeople getting promoted, other
people getting recognized.
It's easy to get frustratedwith that, but the truth is you
probably need to turn the volumeup and communicate more about
yourself.
You know, like you said, it'sthe job you have in addition to
your job.

Speaker 2 (01:25):
Yeah, yeah.
So, promotions aside, where aresome other areas where this
could be really helpful?

Speaker 1 (01:30):
Interviews.
Obviously these days you may belooking for a new job
unexpectedly.
A lot of change going on inorganizations, even in a reorg.
In your job you may have a newmanager or a new team and they
need to know who you are andwhat you've done.
We mentioned performancereviews, family reunions,
conferences, like all of that.

Speaker 2 (01:53):
So what have you been doing this summer?

Speaker 1 (01:56):
That's right, and I think that many of us believe
that our work would just speakfor itself.
We do good work and we'll berecognized, but it's just not
how that works.

Speaker 2 (02:07):
Yeah, I've.
This is something I'vestruggled with my whole career
as somebody who is kind of likea quality over personality type
of person.

Speaker 1 (02:16):
Yeah, and hey I'll also add most of us are busy
doing the work, doing our job,but we don't have time to pull
together material or think aboutthe storytelling, about what
we've just done.
But because of that, I do thinkthat we should be comfortable
telling our stories and sharingwhat I call our greatest hits,
so just coming together withthree to five stories or case

(02:38):
studies that really shine andquickly illustrate what you've
done.

Speaker 2 (02:43):
Yeah, so like kind of what you might see on an agency
website.

Speaker 1 (02:46):
That's right, and I often see people calling them
case studies, and the way I liketo approach it more is a story.
You're actually trying toconnect with another human being
, helping them to understand whoyou are, what your talents are
and what you've done with thatwork.
So a story gets to the heart ofthe emotional content that you
want to convey.

Speaker 2 (03:07):
Let's dig into that.
Tell us a story about telling astory.

Speaker 1 (03:13):
So I like to approach this kind of like a hero's
journey.
So you're going to think of arecent project and you're going
to give that some context.
Who was involved?
What were you trying to achieve?
Then go into some of theextremes.
What was the most high stakesabout the project?
What was the gnarliest part ofthe problem?
What went horribly wrong?

(03:33):
What were your grievances?
Allow that emotion of why didyou care about this specific
project?
And then, lastly, you're goingto land it by saying what you
did to help turn it around ordeliver, and what was the
measurable outcome of your work.
How did it land?

Speaker 2 (03:51):
You say what did you do, what was your outcome?
I noticed a lot of people tellthese stories in terms of we
yeah, I get it, we all do thingswith teams and with others.

Speaker 1 (04:03):
but to own your story , you really have to say what I
did and how your talents andyour effort fit into the overall
success of the project orprogram.
If you can't articulate that,I'd be curious to hear what
you're doing all day with theteam, right Like you may not
have a role in that, in thatproject.
So I think it's safe to saythat there are things that

(04:26):
needed to get done that only youcould have done or seen, or
disasters only you could haveprevented, and you need to own
those.

Speaker 2 (04:35):
Yeah, If you can't tell that story, I wonder too if
you might just be too deep inthe details.
And if you're too deep in thedetails, it's important to see
the big picture of the project,right.

Speaker 1 (04:43):
Absolutely, absolutely.
To be able to step back andremember that not everyone
understands the intricacies ofyour B2B internal software tool
and tell a bigger story.

Speaker 2 (04:56):
Okay, let me see if I get this straight.
Hero's journey.
We set the stage.
Who's there?
What's the problem?
What's the call to thisadventure?
What are you trying to do?
And then turn up the contrastby pulling out those extremes,
Like we were?
We were climbing the mountainand then the bear came.

Speaker 1 (05:14):
That's right.
Get those disasters in there,yep.

Speaker 2 (05:17):
What else went wrong?
And then, what steps did youtake to transform the situation
and turn it around?
And then, what's did you taketo transform the situation and
turn it around?
And then what's the proof thatyou did it?
That's right.

Speaker 1 (05:26):
And I think one of the things to consider is I
understand not every projectthat we work on has that clear,
measurable outcome and in thosecases, can you gather some
testimonials from folks that youworked with or feedback from
your manager or client customerreviews?
Anything that helps illustratethe quality of the work that you

(05:47):
did can be really useful.

Speaker 2 (05:58):
For people that are nervous to communicate about
themselves, this could be alittle bit like a minefield.
What should we be watching outfor as we tread into the
territory?
Yeah, right.

Speaker 1 (06:08):
I think that for many people it's uncomfortable to
brag, so claiming or owning whatyou've done and then having the
confidence to talk about thatcould be a very new experience
for you.
So I think that's a good way tostart.
One way around this is topractice it out loud.
So your dog is a fan of yours.
Practice with your cat.

(06:29):
Practice with someone who'sgoing to support you in kind of
getting this story nailed andget you more comfortable with
saying it.
Practice is a big piece of itand I know it's easy to
understate and say I helped or Icontributed or I was part of.
But, like I said earlier, ownyour part of it, own the
strengths of the conversationsyou brought to the solution and

(06:51):
be bold and braggy.
And I guarantee you, if youhave a hard time being bold and
braggy, you can turn up thevolume to 11 and you're probably
only hitting a five or six.

Speaker 2 (07:03):
I love that, but we don't want to go so far that we
end up you don't want to end upon the LinkedIn lunatics
subreddit.

Speaker 1 (07:09):
That's right.

Speaker 2 (07:11):
How I closed the biggest deal of my career at my
grandma's funeral.
I assume there's an expert modeto all this.
What are some pro tips?

Speaker 1 (07:22):
I think it's easy to think that all of us should have
six to 10 outstanding successes, but people also laid off or
projects get canceled or reorgsmake the last year, 18 months,

(07:50):
of your work irrelevant.
How do you position that?
It's okay, it happens, but makethat into an exciting story?
I think it's important toremember that our good judgment
comes from having bad judgment,so it's okay to have made
mistakes, as long as you'velearned from those mistakes.

Speaker 2 (08:06):
That's a great outlook.

Speaker 1 (08:08):
Lastly, if this is just too hard, can you ask for
help?
Just get somebody with a littlebit more distance who might
have the time to see your storymore clearly and you might be
really impressed of what they'reable to come up with after
working with you and seeing youin action.

Speaker 2 (08:24):
When you say somebody with distance and with writing
abilities.
It actually makes me thinkabout ChatGPT and kind of as a
little exercise I took I thinkit's about 196 pages of
performance appraisals from aneight-year career of mine I
popped it into ChatGPT and Iasked it to find three to five
themes about my own developmentso I could get a better sense of

(08:45):
my own story.

Speaker 1 (08:46):
I love that idea and I think the key there is that
you put in a lot of informationfor it to work with, right yeah.
So you're really saying here'sall the information.
Synthesize the top three tofive qualities that are coming
up in this feedback.

Speaker 2 (09:02):
Yeah Well, listeners, go ahead and give that a shot.
Let us know how it worked out.
Email us at hello atunseriouscom.
Courtney, thank you so much forthis today.
My pleasure.
Always fun to be with you,Micah, Thanks so much.
Courtney walks the talk andcommunicates about herself.
You can keep up with her aticonicleadershipcoachingcom.

(09:23):
Sign up for the newsletter,schedule a free introductory
chat as well, and in the shownotes we'll have a link to the
PDF cheat sheet that accompaniesevery Upshots episode.
This podcast is brought to youby Unserious Group.
We're a communications andstrategic consulting practice
that helps companies and leadersnavigate their rapidly changing
workplace by lowering thestakes and working more
efficiently, playfully andcreatively.

(09:43):
At Unserious, we make work play.