April 22, 2025 • 12 mins
Reading employee emails? Surprise visits to "catch" them working? Our new episode breaks down why these surveillance tactics reveal more about your leadership gaps than employee performance. Listen for better alternatives.
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Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
John Broer (00:01):
That's right.
It's time for another episodeof "You Might Be a Bosshole If
we're finding that this isbecoming one of our more popular
types of segments on TheBosshole Chronicles.
So sit back and ask yourselfthe question am I spying on my
direct reports and if so, couldI be in the Bosshole Zone?
(00:24):
Let's check it out.
The Boss Hole Chronicles arebrought to you by Real Good
Ventures, the talentoptimization firm, helping
organizations diagnose theirmost critical people and
execution issues withworld-class analytics.
Make sure to check out all theresources in the show notes and
(00:44):
be sure to follow us and shareyour feedback.
Enjoy today's episode.
Sara Best (00:52):
Hi everybody, welcome back to "You Might Be a Boss
Hole, If a special episode ofthe Boss Hole Chronicles.
It's good to have you with ustoday.
Here's my trusted partner andfriend, John Broer, to tell us
what is our subject matter fortoday.
John Broer (01:09):
Well, Sara, this may seem hard to believe, but you
might be a Bosshole if you arespying on your direct reports.
Sara Best (01:19):
Spying on your direct reports.
John Broer (01:20):
Spying on your direct reports and let me-
there's a couple of differentfacets to this and I've heard,
I've I have not personallyexperienced it.
I know people that have.
I've had managers tell me thisand I just want to share it.
I think if you are doing this,you are absolutely in the Boss
hole Zone.
Let me give you a quick example.
There was an example justwithin the last few years and I
(01:42):
know about this example abusiness owner and the company
had about 60 to 70 peopleworking there and there was a
central office and then therewere people working out in the
field on operations and so forth, different projects and so
forth.
This business owner readeverybody's emails.
I mean, it was widely known andI don't think he kept it a
(02:04):
secret, but he was readingeverybody's emails and I
couldn't believe it.
And somebody who was workingthere I said well, doesn't that
bother you?
He said, well, obviously weknow about it and it's having
the desired intent.
Nobody is doing anythingpersonal on email.
But I was thinking, wouldn'tthe owner of a company really be
focused on bottom line andgrowing the business?
(02:27):
And maybe his thought was well,if people are wasting time on
personal emails, they'respending my money and that goes
to the bottom line.
But I thought that was crazy.
But it was a successfulbusiness.
But he was essentially spyingon them and reading their emails
.
So I don't know, if you werethere and you knew that, how
would that strike you?
Sara Best (02:47):
I would be frustrated .
I worked for a company once andI got a piece of mail and it
was delivered to me from HR andit was opened and it was
actually a personal thank younote and I was told the policy
is your mail is our mail.
So maybe this guy had that samephilosophy.
John Broer (03:06):
Are you serious?
Sara Best (03:07):
I'm totally serious, whoa, and it was unsettling.
I didn't ever expect that, andI can imagine, if I worked in
that company, I would definitelybe censoring.
I would not use my email foranything other than client
transactions, et cetera.
And I just want to stop for aminute, though, and say what
(03:30):
would have an owner needing todo that world that he would feel
it was necessary to do that.
John Broer (03:49):
I don't know.
I do know the business was asuccessful- I'm not going to say
what kind of business it was.
I know that they weresuccessful.
I know that they were growing.
I don't know if there was asense of paranoia or that.
You know what I pay you to dothis work and I don't want
anybody doing personal stuff oncompany time.
Sara Best (04:05):
Yeah.
John Broer (04:08):
I mean generally, that's going to come out anyway.
You're going to find out basedon, you know, maybe poor
performance or some issues.
But I just thought, wow, that'sa really interesting use of an
owner's time reviewingeverybody's email.
Sara Best (04:19):
Yeah, not the highest and best use of an owner's time
, if you ask me.
John Broer (04:22):
I wouldn't think so.
No, go ahead.
Sara Best (04:24):
Well, I bet you have another example.
John Broer (04:27):
I do.
I actually have two that arekind of related and these
actually came from managers, andI had a just because I spent so
much time in the field of, orin the space of, sales and
business development andcoaching managers and sales
teams and so forth.
I had one manager say yeah, youknow what I like to do.
(04:47):
We have people, we have a veryconfined territory I mean it's
just within our area code orwhatever it is.
All of my people are in closeproximity, but out in the field.
He said I like to go out andjust show up and when they're on
appointment and just show upand surprise them and say, hey,
(05:08):
I'm going to be working with youtoday, I do remember saying,
okay, well, so how does, howdoes that work out?
He goes well, I mean, they'reon their toes and uh, uh,
they've all kind of got used toit that I'll just show up.
I'm thinking once again why doyou feel the need to do that?
Sara Best (05:23):
Um, well, that seems more about him yeah what he
needs and not at all attentiveto how people work best and how
to support people workingeffectively.
I think about the stats youoften share, John, about change
challengers.
John Broer (05:39):
Uh-huh.
Sara Best (05:39):
But 62.8% of the population?
Or is it the other way around68.2, 62.8%?
John Broer (05:46):
Change challengers is around 64%.
Sara Best (05:49):
64% of the population in that category.
Those are people that need alittle runway and planning.
They need to be aware of what'scoming next.
Surprises like that, thingsthat completely shift the focus
or the schedule or, you know,move the deck chairs all of a
sudden, they shut people down,they make their work ineffective
(06:09):
, they kind of make peoplefreeze up.
So it's like a gotcha momentand, yeah, I just don't think
that's healthy.
John Broer (06:14):
And see, this is why I wanted to talk about this,
because I think this is Bosshole behavior, that, ultimately,
now this person, that example,that last example and I think
you know you made this pointbefore we hit record.
Maybe they're just saying, hey,I want to make myself available
, I want to be out there withyou, I'm going to show up, I
know your itinerary for the day.
I'm here to help.
(06:35):
That could very well be theirintent.
Sara Best (06:38):
Okay, then note to self.
John Broer (06:39):
Okay.
Sara Best (06:40):
How about just say would that be helpful?
Yeah, I'd like to offer thissupport.
Would you find that valuable?
Could I?
Could I come in you know shadowwith you?
Or if I, you know, I'd like to,I'd really like to spend time.
What would be a good week.
What would be a good day.
John Broer (06:54):
And, and not only that, but like, since the
manager is going to show up, howcan, how can you use me, a
salesperson or a clientrepresentative if I know that
I'm going to have a manager withme, that can change the whole
tone or approach or strategy toa call.
But if you just pop in, I meanthat totally blows that out of
the water.
So I love that perspective.
Now the other one this guy wasdefinitely a Boss hole.
(07:18):
He said, and kind of proudly hesaid, well, I got, I got people
all over the country.
And he said, and I'll okay.
Now, part of this I'm thinking,was he just full of crap?
I mean, this could be BS.
But he said I, he would show upin their city, which means he
either had to drive there or hehad to fly there on a Monday or
Tuesday.
Because he added the itineraryand said I'm with you this week,
(07:38):
I'm going to be spending thenext couple of days with you.
And I do know, I do know inthat case he was trying to trap
them, he was trying to catchthem, sort of padding their
itinerary and, you know, really,maybe communicating this is my
itinerary, but I'm going toreally, you know, see if this is
what he's doing, this person orthe salesperson or
representative is doing duringthe week and I'm thinking, okay,
(07:59):
that's just sick and that issmoke from.
That's smoke from a differentfire.
You've got other issues and then, when it comes to all of this,
Sara and we talk about trust somuch on the podcast and in our
work.
This does not help to buildtrust in any way.
Any of these scenarios.
And I'm thinking, if you feellike you have to trick or trap
(08:21):
or spy on your direct reports,there are other problems or
issues at play that need yourattention first.
Does that make sense?
Sara Best (08:29):
It makes total sense to me, John.
I would offer that one of thethings that's likely missing in
that scenario is a skill set.
Missing in that scenario is askill set, a leader skill set,
where questions are asked,appropriate questions, data is
shared back and forth and directfeedback is provided.
Candor is part of theconversation.
(09:11):
So this whole mysterious likeI'm going to show up and get you
Right if the target is close inrange or it's not- you know,
your performance is hitting themarker.
It isn't, and I'm going to bethe kind of person that supports
even if you're not hitting thetarget.
We're going to investigate why.
So, communication, leadership,trust, autonomy, those kinds of
(09:32):
things are absent in this littletactic.
John Broer (09:35):
Oh yeah, for sure, for sure.
And again, I know we like toassume positive intent, but
let's face it, we've talkedabout this for over almost five
years now in the Bossh oleChronicles and we just know that
there are managers out therethat do not have positive intent
and they're assuming the wrongthing.
So you know, I remember whenTodd Dewitt, Dr.
Todd Dewitt was on the programand he talked about you know, it
(09:58):
used to be when everybodyworked in the same office we
would manage by observation.
I could see if you were workingand in reality people could
still be screwing around and notworking.
But in reality now, becausepeople are dispersed, it's like
we have to measure based onperformance, and so that changes
the whole metric to your pointautonomy, trust and being really
(10:18):
clear on what we're measuring.
But if you feel the need totrap your people or spy on them,
something else is wrong and youmay be really really sort of
mired in the Boss hole zone andyou want to get out.
You absolutely want to get out.
Sara Best (10:35):
You do, and if there's other similar kind of
off- the- wall sort of tactics,I think one clue for a leader or
manager if they have anyquestion mark in their mind
about an approach or somethingthey'd like to do in response to
a challenge or performanceissue, run it by a trusted
colleague for input before yougo ahead and pull the trigger on
(10:56):
that little approach.
John Broer (10:58):
Yeah.
Sara Best (10:58):
Because I think you could save yourself a lot of
time and effort and agony, andalso for the employee.
John Broer (11:06):
I totally agree and I think that's great advice.
So well, thanks for letting mebring this up again.
I never experienced it.
Fortunately I did not have- mymanagers were courteous enough
that when they wanted to travelwith me and do some joint calls,
it was very well thought out.
We had a great strategy.
Nobody just showed up on mydoorstep, but I hope that's few
(11:26):
and far between, but greatadvice, Sara, thank you.
Sara Best (11:29):
Thank you, John.
I guess we'll see you next timeon "You Might Be a Boss Hole If
.
John Broer (11:37):
Thanks very much for checking out this episode of
the Bossh ole Chronicles.
It was so good to have you here, and if you have your own Bossh
ole story that you want to sharewith the Bossh ole
Transformation Nation, justreach out.
You can email us atmystory@thebossholechronicles.
com.
Again,mystory@thebossholechronicles.
com, we'll see you next time.
That's right.
It's time for another episodeof "You Might Be a Bosshole If
we're finding that this isbecoming one of our more popular
types of segments on TheBosshole Chronicles.
So sit back and ask yourselfthe question am I spying on my
direct reports and if so, couldI be in the Bosshole Zone?
(00:24):
Let's check it out.
The Boss Hole Chronicles arebrought to you by Real Good
Ventures, the talentoptimization firm, helping
organizations diagnose theirmost critical people and
execution issues withworld-class analytics.
Make sure to check out all theresources in the show notes and
(00:44):
be sure to follow us and shareyour feedback.
Enjoy today's episode.
Sara Best (00:52):
Hi everybody, welcome back to "You Might Be a Boss
Hole, If a special episode ofthe Boss Hole Chronicles.
It's good to have you with ustoday.
Here's my trusted partner andfriend, John Broer, to tell us
what is our subject matter fortoday.
John Broer (01:09):
Well, Sara, this may seem hard to believe, but you
might be a Bosshole if you arespying on your direct reports.
Sara Best (01:19):
Spying on your direct reports.
John Broer (01:20):
Spying on your direct reports and let me-
there's a couple of differentfacets to this and I've heard,
I've I have not personallyexperienced it.
I know people that have.
I've had managers tell me thisand I just want to share it.
I think if you are doing this,you are absolutely in the Boss
hole Zone.
Let me give you a quick example.
There was an example justwithin the last few years and I
(01:42):
know about this example abusiness owner and the company
had about 60 to 70 peopleworking there and there was a
central office and then therewere people working out in the
field on operations and so forth, different projects and so
forth.
This business owner readeverybody's emails.
I mean, it was widely known andI don't think he kept it a
(02:04):
secret, but he was readingeverybody's emails and I
couldn't believe it.
And somebody who was workingthere I said well, doesn't that
bother you?
He said, well, obviously weknow about it and it's having
the desired intent.
Nobody is doing anythingpersonal on email.
But I was thinking, wouldn'tthe owner of a company really be
focused on bottom line andgrowing the business?
(02:27):
And maybe his thought was well,if people are wasting time on
personal emails, they'respending my money and that goes
to the bottom line.
But I thought that was crazy.
But it was a successfulbusiness.
But he was essentially spyingon them and reading their emails
.
So I don't know, if you werethere and you knew that, how
would that strike you?
Sara Best (02:47):
I would be frustrated .
I worked for a company once andI got a piece of mail and it
was delivered to me from HR andit was opened and it was
actually a personal thank younote and I was told the policy
is your mail is our mail.
So maybe this guy had that samephilosophy.
John Broer (03:06):
Are you serious?
Sara Best (03:07):
I'm totally serious, whoa, and it was unsettling.
I didn't ever expect that, andI can imagine, if I worked in
that company, I would definitelybe censoring.
I would not use my email foranything other than client
transactions, et cetera.
And I just want to stop for aminute, though, and say what
(03:30):
would have an owner needing todo that world that he would feel
it was necessary to do that.
John Broer (03:49):
I don't know.
I do know the business was asuccessful- I'm not going to say
what kind of business it was.
I know that they weresuccessful.
I know that they were growing.
I don't know if there was asense of paranoia or that.
You know what I pay you to dothis work and I don't want
anybody doing personal stuff oncompany time.
Sara Best (04:05):
Yeah.
John Broer (04:08):
I mean generally, that's going to come out anyway.
You're going to find out basedon, you know, maybe poor
performance or some issues.
But I just thought, wow, that'sa really interesting use of an
owner's time reviewingeverybody's email.
Sara Best (04:19):
Yeah, not the highest and best use of an owner's time
, if you ask me.
John Broer (04:22):
I wouldn't think so.
No, go ahead.
Sara Best (04:24):
Well, I bet you have another example.
John Broer (04:27):
I do.
I actually have two that arekind of related and these
actually came from managers, andI had a just because I spent so
much time in the field of, orin the space of, sales and
business development andcoaching managers and sales
teams and so forth.
I had one manager say yeah, youknow what I like to do.
(04:47):
We have people, we have a veryconfined territory I mean it's
just within our area code orwhatever it is.
All of my people are in closeproximity, but out in the field.
He said I like to go out andjust show up and when they're on
appointment and just show upand surprise them and say, hey,
(05:08):
I'm going to be working with youtoday, I do remember saying,
okay, well, so how does, howdoes that work out?
He goes well, I mean, they'reon their toes and uh, uh,
they've all kind of got used toit that I'll just show up.
I'm thinking once again why doyou feel the need to do that?
Sara Best (05:23):
Um, well, that seems more about him yeah what he
needs and not at all attentiveto how people work best and how
to support people workingeffectively.
I think about the stats youoften share, John, about change
challengers.
John Broer (05:39):
Uh-huh.
Sara Best (05:39):
But 62.8% of the population?
Or is it the other way around68.2, 62.8%?
John Broer (05:46):
Change challengers is around 64%.
Sara Best (05:49):
64% of the population in that category.
Those are people that need alittle runway and planning.
They need to be aware of what'scoming next.
Surprises like that, thingsthat completely shift the focus
or the schedule or, you know,move the deck chairs all of a
sudden, they shut people down,they make their work ineffective
(06:09):
, they kind of make peoplefreeze up.
So it's like a gotcha momentand, yeah, I just don't think
that's healthy.
John Broer (06:14):
And see, this is why I wanted to talk about this,
because I think this is Bosshole behavior, that, ultimately,
now this person, that example,that last example and I think
you know you made this pointbefore we hit record.
Maybe they're just saying, hey,I want to make myself available
, I want to be out there withyou, I'm going to show up, I
know your itinerary for the day.
I'm here to help.
(06:35):
That could very well be theirintent.
Sara Best (06:38):
Okay, then note to self.
John Broer (06:39):
Okay.
Sara Best (06:40):
How about just say would that be helpful?
Yeah, I'd like to offer thissupport.
Would you find that valuable?
Could I?
Could I come in you know shadowwith you?
Or if I, you know, I'd like to,I'd really like to spend time.
What would be a good week.
What would be a good day.
John Broer (06:54):
And, and not only that, but like, since the
manager is going to show up, howcan, how can you use me, a
salesperson or a clientrepresentative if I know that
I'm going to have a manager withme, that can change the whole
tone or approach or strategy toa call.
But if you just pop in, I meanthat totally blows that out of
the water.
So I love that perspective.
Now the other one this guy wasdefinitely a Boss hole.
(07:18):
He said, and kind of proudly hesaid, well, I got, I got people
all over the country.
And he said, and I'll okay.
Now, part of this I'm thinking,was he just full of crap?
I mean, this could be BS.
But he said I, he would show upin their city, which means he
either had to drive there or hehad to fly there on a Monday or
Tuesday.
Because he added the itineraryand said I'm with you this week,
(07:38):
I'm going to be spending thenext couple of days with you.
And I do know, I do know inthat case he was trying to trap
them, he was trying to catchthem, sort of padding their
itinerary and, you know, really,maybe communicating this is my
itinerary, but I'm going toreally, you know, see if this is
what he's doing, this person orthe salesperson or
representative is doing duringthe week and I'm thinking, okay,
(07:59):
that's just sick and that issmoke from.
That's smoke from a differentfire.
You've got other issues and then, when it comes to all of this,
Sara and we talk about trust somuch on the podcast and in our
work.
This does not help to buildtrust in any way.
Any of these scenarios.
And I'm thinking, if you feellike you have to trick or trap
(08:21):
or spy on your direct reports,there are other problems or
issues at play that need yourattention first.
Does that make sense?
Sara Best (08:29):
It makes total sense to me, John.
I would offer that one of thethings that's likely missing in
that scenario is a skill set.
Missing in that scenario is askill set, a leader skill set,
where questions are asked,appropriate questions, data is
shared back and forth and directfeedback is provided.
Candor is part of theconversation.
(09:11):
So this whole mysterious likeI'm going to show up and get you
Right if the target is close inrange or it's not- you know,
your performance is hitting themarker.
It isn't, and I'm going to bethe kind of person that supports
even if you're not hitting thetarget.
We're going to investigate why.
So, communication, leadership,trust, autonomy, those kinds of
(09:32):
things are absent in this littletactic.
John Broer (09:35):
Oh yeah, for sure, for sure.
And again, I know we like toassume positive intent, but
let's face it, we've talkedabout this for over almost five
years now in the Bossh oleChronicles and we just know that
there are managers out therethat do not have positive intent
and they're assuming the wrongthing.
So you know, I remember whenTodd Dewitt, Dr.
Todd Dewitt was on the programand he talked about you know, it
(09:58):
used to be when everybodyworked in the same office we
would manage by observation.
I could see if you were workingand in reality people could
still be screwing around and notworking.
But in reality now, becausepeople are dispersed, it's like
we have to measure based onperformance, and so that changes
the whole metric to your pointautonomy, trust and being really
(10:18):
clear on what we're measuring.
But if you feel the need totrap your people or spy on them,
something else is wrong and youmay be really really sort of
mired in the Boss hole zone andyou want to get out.
You absolutely want to get out.
Sara Best (10:35):
You do, and if there's other similar kind of
off- the- wall sort of tactics,I think one clue for a leader or
manager if they have anyquestion mark in their mind
about an approach or somethingthey'd like to do in response to
a challenge or performanceissue, run it by a trusted
colleague for input before yougo ahead and pull the trigger on
(10:56):
that little approach.
John Broer (10:58):
Yeah.
Sara Best (10:58):
Because I think you could save yourself a lot of
time and effort and agony, andalso for the employee.
John Broer (11:06):
I totally agree and I think that's great advice.
So well, thanks for letting mebring this up again.
I never experienced it.
Fortunately I did not have- mymanagers were courteous enough
that when they wanted to travelwith me and do some joint calls,
it was very well thought out.
We had a great strategy.
Nobody just showed up on mydoorstep, but I hope that's few
(11:26):
and far between, but greatadvice, Sara, thank you.
Sara Best (11:29):
Thank you, John.
I guess we'll see you next timeon "You Might Be a Boss Hole If
.
John Broer (11:37):
Thanks very much for checking out this episode of
the Bossh ole Chronicles.
It was so good to have you here, and if you have your own Bossh
ole story that you want to sharewith the Bossh ole
Transformation Nation, justreach out.
You can email us atmystory@thebossholechronicles.
com.
Again,mystory@thebossholechronicles.
com, we'll see you next time.
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