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November 4, 2025 23 mins

You had the tough conversation. You thought you were clear. But nothing changed.

Now what?

Most leadership advice stops at "have the conversation" and never tells you what to do when the issue repeats. In this episode, leadership consultant Colby Morris walks you through exactly how to handle the second conversation—and why it's often more important than the first.


What You'll Learn:

  • Why the first conversation probably didn't work (and how to avoid the same mistake)
  • The two bad paths leaders take when issues persist (and the real cost of avoidance)
  • When to have the second conversation (and why timing is non-negotiable)
  • The "recap method" that creates accountability while protecting you as a leader
  • How to shift your language from coaching to accountability without losing respect
  • When to escalate to HR or start a PIP (the two-strike framework)
  • Step-by-step guide to preparing for and conducting the second conversation


Key Statistics:

  • Every avoided conversation costs organizations $7,500 and 7 lost workdays
  • 53% of employees handle toxic situations by ignoring them
  • 70% of employees feel disengaged when poor performance goes unchallenged
  • 25% of managers postpone difficult conversations for a year or longer
  • Low performers without accountability cause a 30% decrease in team productivity

Perfect for middle managers, directors, and team leaders who need practical guidance on accountability conversations that actually work.


Related Episodes:

  • Episode 31: How to Have Tough Conversations with Employees 
  • Episode 26: Difficult Conversations for New Leaders


Connect with Colby Morris

Website: nxtstepadvisors.com 

LinkedIn: linkedin.com/in/colbymorris

Email: Colby@NXTStepAdvisors.com

Services: Executive Coaching | Leadership Training | Keynote Speaking | Tough Conversations Workshop

Enjoyed this episode?

  • Subscribe to The Things Leaders Do on Apple Podcasts or Spotify
  • Leave a 5-star review
  • Share with a leader who's avoiding a tough conversation right now

Remember: Keep having the hard conversations instead of avoiding them. Keep being clear about expectations and consequences. And keep giving your people a real chance to succeed before you move to termination. Because those are the things that leaders do.

#ToughConversations #LeadershipAccountability #PeopleFirstLeadership #MiddleManagement #PerformanceManagement #DifficultConversations #LeadershipDevelopment #HRLeadership


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Transcript

Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
SPEAKER_00 (00:00):
People first leadership.
Actionable strategies, realresults.
This is Things Leaders Do withColby Morris.
Okay.

SPEAKER_01 (00:12):
So you had the tough conversation.
You thought you were clear.
I mean you addressed the issue,you laid out the expectations,
you felt like you handled itwell.
But then nothing changed.
The same behavior showed upagain.
The same mistake was repeated.
The same problem is stillsitting there on your desk.

(00:34):
And now you're wondering, do Ihave the same conversation
again?
Do I go straight to HR?
Did I fill as a leader?
What am I supposed to do whenthe first tough conversation
didn't work?
Well, here's what I want you tohear today.
The second conversation is oftenmore important than the first.

(00:56):
And how you handle it determineswhether you're actually leading
or just hoping problems go awayon their own.
Hey leaders, this is ColbyMorris, and this is the Things
Leaders Do podcast.
I'm all about giving youpractical strategies that make
you a better leader faster.
These episodes are short, 15 tosay 23 minutes, so you can

(01:21):
listen on your commute and thenput something into practice the
moment you hit the office.
No fluff, no theory, just realtools you can use right now.
Today we're talking about whathappens after the tough
conversation doesn't work.
Because most leadership advicestops at have the conversation,

(01:41):
but never tells you what to dowhen nothing changes.
All right, so let's start withwhy the first conversation
probably didn't work in thefirst place.
Because understanding this helpsyou not make that same mistake
twice.
I see this happen in two waysusually, and it usually depends

(02:02):
on how long you've been leading.
See, new leaders tend to kind ofbrush around the topic without
actually delivering the message.
They just dance around it.
They hint at it like a LaCroixtaste.
They say things like, hey, Inoticed that sometimes the

(02:23):
reports are a little late.
Yeah.
What they really need to say is,hey, your reports have been late
three times in the last twoweeks, and that really creates
problems for the entire team andthat needs to stop.
They think they had theconversation because they
mentioned it.
But the employee walks awaythinking it was just a casual

(02:45):
observation, not a serious issuethat needs to change.
Look, I've done this myselfearly on.
You think you're being nice, butyou're actually just being
unclear.
On the flip side, moreexperienced leaders sometimes go
the opposite direction.
They mention the issue once andfigure that because the boss

(03:07):
brought it up, the person wouldjust understand that it's been
addressed.
Like, well, I've said something,so they know it's important.
Here's the thing.
Just because you mentionedsomething doesn't mean the
message was, you know, actuallydelivered.
Both of these approaches failbecause there's no clarity.

(03:27):
No clarity about what needs tochange, why it matters, what
happens if it doesn't change.
So if you're sitting herethinking, I had the conversation
and nothing changed, askyourself honestly, okay,
honestly, did you actuallydeliver the message?
Or did you dance around it andhope they'd figure it out?

(03:51):
Because if the message wasn'tclear the first time, the second
conversation is your chance toget it right.
And you need to get it right.
When the first conversationdoesn't work, I see leaders go
down one of two really badpaths.
And I bet you've seen this too,or maybe you've done it

(04:12):
yourself.
Path one is they go straight totermination or a pip, you know,
a performance improvement plan.
They skip the secondconversation entirely.
They go straight to HR and saysomething like, I want to start
the process and let this persongo.
Or we need to put them on aperformance improvement plan.

(04:34):
And look, sometimes that isnecessary.
I get it.
But a lot of times, it'spremature.
You're going nuclear when therewere steps you could still take,
or steps you still could havetaken.
Okay, you're jumping to thefinal option without giving the
person a real chance to coursecorrect.

(04:55):
And then pass two, they justavoid it completely.
This is actually way morecommon, and the numbers back
this up.
53% of employees handle toxicsituations by just ignoring
them.
That includes managers.
We avoid the second conversationbecause we either don't like

(05:20):
conflict, maybe nobody evertaught you how to deal with it
in a healthy way.
So we just, you know, hope itgets better.
We convince ourselves maybe itwas just a one-time thing.
Maybe they'll figure it out ontheir own.
Maybe it'll just magicallyresolve itself if we give it

(05:40):
time.
But here's what the researchshows: every conversation
failure, every time we avoidhaving the conversation we need
to have, costs an organization$7,500 and more than seven lost
work days.
Hey, that's per conversation.

(06:01):
So when you're avoiding thatsecond conversation, you're not
saving yourself discomfort.
You're actually costing yourorganization real money and real
time.
And meanwhile, the behaviorcontinues.
The problem gets worse.
And here's the part that killsme.

(06:21):
The rest of your team iswatching.
Nearly 70% of employees feeldisengaged when they watch
someone underperform and seenothing happening about it.
They're thinking, why am Ibusting my butt when that person
isn't even trying and gets awaywith it?
That's the message you'resending when you avoid the

(06:41):
conversation.
You're not being nice.
You're being unfair to everyoneelse on your team.
Don't take either of thesepaths.
Okay.
There's a better way, and we'regoing to walk through it.
So here's the rule, and this isnon-negotiable.

(07:03):
When the issue repeatsimmediately after coaching, it
must be addressed right away.
Not, you know, not next week,not when it's you know more
convenient, not when you finallywork up the courage.
Immediately.
Because when you let it slide,even just once, you are sending

(07:27):
a message.
And that message is what wetalked about wasn't actually
that important.
I didn't really mean it.
Here's a stat that's going toblow your mind.
25% of managers have postponedchallenging discussions for a
year or longer.
A year.

(07:48):
Think about the damage that doesto performance, to team morale,
to your credibility as a leader.
Don't be that person.
Now, sometimes the repeat can bean accident.
People make mistakes.
They're human.
I've made plenty of mistakesmyself, God knows.

(08:10):
But sometimes, and you need tobe aware of this, it can be
someone testing you.
They want to see if you'reactually going to hold them
accountable, or if you're justblowing smoke.
This happens all the time.
Especially if you're new toleadership or new to the team.

(08:30):
People will push boundaries tosee what the real boundaries
actually are.
And it's not always malicious.
Sometimes you're just figuringout, you know, what kind of
leader you are.
So the second time the issueshows up, you address it.
No exceptions, no waiting, nohoping it goes away.

(08:52):
Here's what's interesting.
The second conversation isactually easier than the first
one in a lot of ways.
Because now you have a pattern.
You're not making assumptions,you're not wondering if it's a
one-time thing.
You know it's an issue becauseit happened again.
You have evidence.

(09:13):
And remember this.
When low performers stick aroundwithout any accountability,
research from Harvard BusinessReview shows it leads to a 30%
decrease in team productivity.
30% decrease in teamproductivity.

(09:40):
Your high performers startwondering why they're working so
hard.
Your middle performers startthinking, well, maybe they can
coast too.
That clarity, that pattern makesthe second conversation more
straightforward.
Okay, you're not guessinganymore.
You know what needs to happen.

(10:02):
All right, so let's talk aboutwhat actually changes in the
second conversation.
First, your tone doesn't change.
Okay, if you're a people firstleader, you're still respectful.
You're still calm.
You don't raise your voice.
That doesn't change just becausethis is the second time.

(10:23):
In fact, the tone that you hearme using right now, that's the
tone I use like 24/7.
If I'm coaching someone, if I'mcorrecting someone, whatever it
is, this is the tone I use.
I don't get upset, even if I amupset.
I don't, I don't put that in myvoice or my tone.

(10:43):
Okay.
But your language absolutelymust change.
The second conversation needs tomove toward forward action and
concrete consequences.
It needs to sound different fromthe first one.
Okay.

(11:03):
Now, you do need to ask whatcaused something, right?
So give them a bump to justexplain what has happened, you
know?
Hey, this happened again.
What's, you know, what happened?
Can you help me understand whyyou're missing this deadline,
that kind of thing?
If they don't really have agreat reason, I didn't say

(11:27):
excuse, a great reason, then youkind of bump it up a little bit
and you say something like,Look, this happened again 10
days after our last conversationabout it.
Okay, we specifically discussedthat your reports needed to be
on time.
And here we are two weeks laterwith another late report.

(11:48):
Okay, this does have or couldhave an impact on your future
here, and I need you tounderstand that.
See the difference?
It's still respectful, but it isdirect.
It connects the dots betweentheir behavior and the
consequences.
It removes that ambiguity.

(12:09):
The first conversation mightfeel more coaching heavy.
Okay.
The second conversation feelsmore accountability heavy, and
that's appropriate.
Now, here's the approach I usefor the second conversation, and
I think this is reallyeffective.
I start by asking them to recap.

(12:31):
I'll say something like, Can yourecap for me what we discussed
last time you were in hereregarding this situation?
What did we ultimately decidewas the issue and how did we
address it?
And then I just let them talk.
I want them to own thisconversation.
Here's why this works.

(12:52):
As a people first leader, I'vehad multiple conversations and
coaching with this person,especially in our one-on-ones.
So this isn't like coming out ofnowhere.
They know and they can speak toit.
When they recap it for me, it'san acknowledgement that we've
already addressed this.
It's not a surprise to anyone atthis point.

(13:15):
They know it, I know it.
And whatever this conversationleads to is the next step.
This approach also protects you,by the way, okay, because if
they can't recap theconversation or they act
surprised, that tells you thatthe first conversation wasn't
clear enough.

(13:36):
And that's valuable information.
And it's on you.
You have to own that.
Because if you aren'tcommunicating clearly the first
time, it's not their fault.
You have to make sure theyunderstand.
Okay.
But most of the time, they knowexactly what you're talking

(13:58):
about.
And that makes theaccountability piece much
easier.
So let's talk about when you doneed to escalate beyond just the
two of you.
Because at some point you mightneed to involve HR or start the
formal process.
Here's my framework.

(14:18):
I involve HR when I've coachedsomeone at least twice,
depending on how serious theissue is.
Now, if it's severe enough, likea major policy violation or
something that puts the companyat risk or creates a hostile
work environment, it couldeither be immediate termination

(14:39):
or a final warning right out ofthe gate.
Those situations absolutelyexist, and you need to know your
company's policies and involveHR immediately when those
happen.
Don't try to handle those onyour own.
But for most performance issues,the you know, the everyday stuff
like missed deadlines, qualityproblems, attitude issues, after

(15:01):
I've addressed it twice, itbecomes like a two-strike
situation.
We're at a point where somethingmore formal needs to happen.
HR usually needs to be involvedin a pip anyway, because there's
legality around the language andthe process.
You want to make sure you'reprotected and the employee is
treated fairly.

(15:21):
Okay, don't skip this step.
But here's my standard.
And this is how I know when it'stime to move.
When I know that I know that Iknow that they know it's time to
escalate.
Colby, what does that mean?
It means we've talked, we'vediscussed it multiple times.

(15:44):
I've been clear.
They've acknowledged it.
There's no ambiguity left, zero.
At that point, if the behaviorcontinues, it's not about me,
you know, giving up on them.
It's about acknowledging thatthis person just isn't a fit for
this role or this team.
And that's okay.

(16:05):
Hey, not everyone is a fiteverywhere.
But as a leader, you have theresponsibility to the rest of
your team and to theorganization to address
performance issues.
You can't let one person's poorperformance drag down everyone
else indefinitely.
I don't ever want to feel like Igave up on someone.

(16:27):
That's just, that's just not whoI am.
I want to be able to say tomyself, to them, to HR, to my
boss, that we exhausted all ofour options.
We coached, we documented, wegave them every opportunity to
course correct.
We were clear aboutexpectations, we were clear

(16:48):
about consequences.
And at this point, the decisionis clear.
And you know what?
They know that too.
It makes it easier to have whatmight be that final conversation
when it's time because they knowat this point that they haven't
made it, they didn't cut it.

(17:09):
And that's how you approach itwith integrity.
That's how you sleep at nightknowing you did the right thing.
All right.
So let's get really practical.
If you need to have the secondtough conversation this week,
here's exactly what you do, stepby step.

(17:30):
First, schedule it quickly.
Look, don't wait.
Stop waiting.
Okay, that thing you're thinkingabout, stop waiting.
Don't let days pass while youwork up your nerve.
Okay, as soon as you see thebehavior repeat, get it on the
calendar.
Same day if possible.
Next day at the latest.

(17:50):
The longer you wait, the weirderit gets and the less effective
it becomes.
Second, prepare your language.
Look, write it down.
Okay, don't wing it.
Write down things like what wasdiscussed in the first
conversation, what you bothagreed would change, what

(18:12):
actually happened since then,and be specific.
You know, give dates andexamples.
What needs to happen goingforward, what the consequences
are if it doesn't.
Okay, be specific.
Use concrete examples, no vaguelanguage like sometimes or
often, say three times in thelast two weeks, or on Tuesday

(18:36):
and Thursday.
And then third, start with therecap.
Can you recap for me what wediscussed last time about this
and let them talk?
Let them own it.
Don't fill the silence.
Just wait and let them talk.
And then fourth, acknowledge thereality.

(18:59):
We had that conversation, youknow, six days ago, and this
issue has happened again.
That tells me something needs tochange, either in how you're
approaching this or whether thisrole is the right fit for you.
You're connecting the dots forthem.
You're making it clear that thisis serious.

(19:23):
Fifth, let me be clear aboutnext steps.
Here's what needs to happen fromthis point forward.
Here's what success looks like.
And here's what happens if thiscontinues.
No ambiguity, no sugar clothing,just clarity.
And then sixth, documenteverything.

(19:46):
Okay, this is crucial.
Send a follow-up emailsummarizing the conversation.
Okay, keep notes in a file, dateeverything.
If this ends up going to HR or apip, you need documentation that
shows you addressed it multipletimes.
Okay, protect yourself and befair to the employee.

(20:08):
And here's the emotional partthat nobody talks about.
This can be hard.
Okay, even when you know it'snecessary, even when you've done
everything right, sometimes it'sstill hard to have these
conversations.
It doesn't feel great.
But you know what's harder?

(20:28):
Letting the behavior continueand watching your team lose
respect for you.
Letting poor performance dragdown everyone else who's working
their butt off.
Avoiding the conversation untilyou feel like you have no choice
but to fire someone withoutwarning because you never
actually address the issueproperly.

(20:49):
The second conversation is anact of leadership.
Yes, it can be uncomfortable,but it's necessary.
And your team, the ones who aredoing the right thing, they're
counting on you to have it.
So here's what I want you to dothis week.
If you have an issue that didn'tresolve after the first

(21:10):
conversation, don't avoid it.
Don't go straight to HR anddon't skip the second
conversation.
Have the conversation.
Do it right.
Use the recap method, be clearabout consequences, document
everything, and give the persona real chance to turn it around.

(21:31):
That's fair.
That's leadership.
And if you're listening to thisthinking, man, I wish I'd done
this differently with someone inthe past, that's okay.
You can't go back and fix that.
But you can do it right the nexttime.
Learn from it and move forward.

(21:52):
Leaders, if your organizationneeds help building leadership
skills around toughconversations, conflict
resolution, or people-firstaccountability, I'd love to
help.
I work with leaders and teamsthrough keynote speaking,
executive coaching, andleadership training to build
people-first cultures that drivereal results.
You can connect with me onLinkedIn or my webpage, and

(22:15):
those are both in the shownotes.
And hey, if this episoderesonated with you, would you do
me a favor?
Subscribe to the show whereveryou listen to podcasts, and
please leave a review.
And share this episode withanother leader who's wrestling
with how to handle a toughsituation.
Maybe they're avoiding aconversation right now.

(22:37):
Send this to them.
Let them know they're not aloneand finding this stuff hard.
That's how we grow thiscommunity, and that's how we get
the word out to make a biggerimpact in the workplace.
And remember, keep having toughconversations instead of
avoiding them.
Keep being clear aboutexpectations and consequences.

(22:58):
And keep giving your people areal chance to succeed before
you move to termination.
And you know why?
Because those are the thingsthat leaders do.

SPEAKER_00 (23:13):
Thank you for listening to Things Leaders Do.
If you're looking for more tipson how to be a better leader, be
sure to subscribe to the podcastand listen to next week's
episode.
Until next time, keep working onbeing a better leader by doing
the things that leaders do.
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