[00:00:00.250] - Chris
In this episode of Great Practices, we're going to learn about some of the worst practices people have
done when it comes to managing their email. You may be guilty of one or two of these yourself. We'll also
uncover the four fundamentals of good email management, including having an easy to understand filing
system, utilizing a consistent process, using tasks and not your inbox to manage your day, and finally
understanding the power of the email tools that you've been given. Plus, we'll learn what Parades, Big
Bird and Sesame Street have to do with getting control of your email. So let's get right into this episode of
Great Practices with Debbie Kirtland.
[00:00:43.190] - Narrator
It's hard to say when something is a best practice, but it's much easier to know when something is a great
practice. And that's what this podcast is all about. Interviews with CMO and project management leaders
who through years of trial and error have discovered their own great Practices and are now sharing their
insights with you. Now sit back and enjoy the conversation as Chris Copp uncovers another great practice
in this episode.
[00:01:13.070] - Chris
So we'd like to welcome everyone to our episode of Great Practices today. And a number of years ago I
went to a training class with Debbie Kirtland, who's our guest today about Outlook. So I thought, what I'm
going to do, I'm going to learn a couple of tips and tricks, I'm going to add them to my skill set and I'm
going to be on my way. But I left that course with a new Outlook on Outlook. She has a unique way of
looking at Outlook and how to manage email in general. So you may say, well, what does this have to do
with the PMO? Well, here's the deal. Email is still a huge part of our day as PMO leaders, despite the fact
that there are other collaborative tools that's available, like Teams or Slack. Some experts say that on
average, a business user sends and receives 125 emails every single day.
[00:02:05.250] - Chris
It's 15 emails every hour.
[00:02:07.200] - Chris
That has the potential of taking us off track, going down rabbit holes that we'll never get out of, and
watching our inbox slowly overflow with messages demanding our attention. So how can this beast be
tamed? That's what we're going to talk with Debbie about in this episode getting control of your inbox so
you can focus on the more important things like running your PMO. And while she does specialize in
Outlook, the principles that she's going to be covering today apply to Apple, Mail, Gmail, and any other
email tool that you may be using. So welcome to Great Practices. Debbie, can you tell us a little bit about
who you are and what you do?
[00:02:47.220] - Debbie
Yes. Thanks Chris, for having me on the show today. I appreciate that. I work for a company called
Upskill and Win, and I'd like to tell you what we do is we bring order to the chaos today in the workplace.
And we do this by showing our clients how to create a simple and an easy to maintain system to manage
their day to day activities. Our main focus is time, email and information. And really, what makes us
different is that we come in and we utilize a tool that you already use. We're not bringing in any new
systems or new technology. You don't need new technology.
[00:03:28.690] - Chris
[00:03:29.160] - Debbie
You just need to understand what you have to create a system. And the best day is when we hear you
transform my work life. So taking our clients from overwhelmed to in control, that's what we do. That's our
[00:03:42.370] - Chris
That's fantastic. Yeah. I love that. Bringing order to chaos because there's plenty of chaos that needs to
have order brought to it, isn't there? There's no doubt about that. Now this may be a trick question to you,
maybe a little bit, because I know you're not necessarily in the PMO space directly, but I do know that you
work with a bunch of different companies and different types of groups. So what would your definition of a
PMO be? That's a question we like to ask everybody that comes on.
[00:04:11.720] - Debbie
All right. Well, I do believe that it's a group of people inside of an organization that actually set the
standards for project management. So they're kind of the overseers. They want to make sure that it's an
efficient process. Like I said, I think by their nature, they're very organized, process oriented, and so
they're all kind of people know.
[00:04:35.320] - Chris
That is exactly right. Good assessment of what a PMO does there. And you are right. That is the nature of
the beast is to be organized and have those processes that you clearly teach in your classes. So, Debbie,
this is called great practices. But what I want to start off with is I want to start off with some examples of
maybe some of the worst practices that you've seen when it comes to managing. And I'm using that word
loosely, email. So what are some of the horror stories that you may have seen over your career about
how people manage their email?
[00:05:10.790] - Debbie
Well, I think one of the first things that comes to my mind is that when you walk into someone's office and
you see that they're trying to manage their entire day out of their inbox. One of my favorite ones is that
they love to flag emails. They flag them. And I ask them sometimes I said, what are they in a parade?
Because they'll leave them flagged. They don't clear the flag. So that's not efficient. But also we'll see
they're putting things on their calendar that they need to do. They have paper list, they have posted notes
around. And I say immediately, aren't you overwhelmed? I'm overwhelmed. You're going to so many
places to see how to manage a task. So we try to help them create another system. The other thing is
filing that sounds like a simple thing. My boss used to say, everybody can file but you can retrieve. And
that was really true. And you would see them have a system in their Outlook or their email. They have a
system in their paper system, in their electronic documents that were totally different, not even based on
their job description. I mean, we used to call them orphans, you know, those little loose documents that
hang around everywhere and they don't have anywhere to go.
[00:06:38.090] - Debbie
You just put them anywhere. So even once I was working with a very high level executive at a
pharmaceutical company and we went to empty his deleted folder and he said, Stop, that's my filing
system. And I was like, oh, okay, you're falling in the trash. So filing is very important.
[00:06:55.270] - Chris
You're saying his deleted folder or his deleted folder was his filing system. That's where he kept on
[00:07:02.370] - Debbie
That's where he would go look for things. So you nearly need a good system. And the other thing is, when
you do that constantly, I always say, do you say, I know I put it somewhere a lot, right? And then you
proceed to go to so many places to find it. It is not there because the filing system is not good or you
involve other people. I love that. Now you're not only wasting your time, you're wasting the entire office
time. So that's the second thing I see. And the third thing that is really sometimes it just breaks my heart
to see somebody that has thousands and thousands of emails in their inbox and they possibly could even
be emails from the very first day they started their job. They're years old, not days old. And having an
overloaded inbox and trying to work from that clutter is not good. And they'll say, well, I can use search.
Well, if you've ever used search, it's not really the most efficient thing. You'll find your email. So that is
definitely highly inefficient and waste a lot of time.
[00:08:16.270] - Chris
Yeah. So it sounds like you've seen a lot then. I love that example. You said using those flags so much,
it's not a parade. And then I guess with all those posted notes, there's your confetti that's all over the
place as well, just kind of floating down, right? Yeah, I've seen it too. And candidly, I've been guilty of it.
What I've been guilty of is wasting other people's time when I can't find something and I know I've sent it
to somebody else and I'm like, can you send me back my own email that I know that I sent you? That's
terrible, right? That's terrible to do that. So I think we've all been guilty varying degrees of all of these sins
that you've just gone over there. Let's then talk about some great practices because you've got answers
to how to tackle these challenges. So what are your four fundamentals of email management to prevent
falling victim to these horror stories that you mentioned, what would these be?
[00:09:19.850] - Debbie
Well, the first thing you need is a good filing system, OK. You need to have a good process, and that
needs to be based on your personality and the way you think and work. You need an electronic task list.
Our work is coming through to us electronically now, and the paper cannot handle the volume that we get.
And you need to understand the tools that you have been given, how to use them to get the maximum,
the most bang for the buck out of what you already have.
[00:09:53.610] - Chris
Yeah. Okay, good. Let's dive into each one of these a little bit more then. Okay. So we're going to start off
with number one, which is a good filing system. So tell us about that. How can we get some great
practices out of this area?
[00:10:08.090] - Debbie
It really is easy to create a good filing system. I used to tell people, I said, did you ever watch Sesame
Street? And they kind of look at me funny and I say, when Big Bird says some of these things aren't like
the others. Some of these things don't belong. You were grouping like things together. And the way that
we show you how to build a filing system is based on that. We call them homes. We have big homes or
big broad categories is to take a look at your job description, take a look at what you're doing and build
that foundation. Match up to that. So sometimes it's maybe the hardest thing you do, but it's the thing that
pays off in the end that really saves you time. When I started a new company, I immediately built my filing
system based on my needs. And it's amazing how I can quickly lay my hands on anything that I need to
get to. And you can utilize that in your email system. You can utilize it in paper and you can do it with your
[00:11:16.850] - Chris
So you mentioned that example of a home. And I guess to further that analogy right there, what you're
basically saying is you get a home in every place, every room in that home, you're going to store
something differently. So something is going to be in your living room. You're not going to have your
Forks and knives in your living room. Those are clearly going to be in your kitchen. Right. So that's really
the concept there. It's just that everything should have its place in that filing system.
[00:11:43.490] - Debbie
Yeah. So for example, if you're working on projects, you have a big home called projects, and then
underneath that, you would have the names of your projects and you could even have more detail. I tell
you another critical thing with filing, and I see this all the time is work in progress. What you're working on
now and completed work. If you keep all of that in one big bunch, then you have to scroll through a lot of
information that you don't need. And so we teach you how to say, okay, this is completed projects. These
are the projects I'm working on now. Just simple little things like that.
[00:12:19.460] - Chris
Yeah. Do some spring cleaning on a house. That's basically what needs to be done there. So that's good.
All right. So good filing system, basically making sure that everything has a place to go that makes sense,
that you can find that. So that's number one. Number two, you talked about having a good process. So
talk a little bit more about what that is.
[00:12:40.300] - Debbie
Okay. Well, the first thing I do when I go into my email in the morning is my goal is to clean out my inbox.
Okay. That's my goal. I don't want things sending in the inbox. So in order to do that, I have to use the
features of the email client that I have been given. We used to explain those binders that you carried
around. You had a place for calendar, you had a place for contacts, for notes, for tasks. That's all usually
in everyone's email client today. So you look and you say, can these things go into those places? Then if
you have to, not everything works in those features. Sometimes you have to group things together, like
non critical reading or reports that you need to review. So we teach you how to build your folders. So in
the end of the day, you should be able to clear out that inbox. And then people would say to me, oh, I
can't put it away, because if I do, I will never get back to it. Well, that's where my third point is going to
come in. And that's going to be your task that will drive you back to do what you need to do.
[00:13:55.330] - Chris
Okay, well, let's go ahead and we'll get right into that. So basically, you've got that process, which is your
daily routine, that you know that you're going to be doing these things at these times, and this is how
you're going to do it. So that's number two. And number three then is I think you said utilizing tasks. Right.
To drive your day and not your inbox. So what does that look like?
[00:14:16.590] - Debbie
Right. And so everybody has access pretty much in the corporate world that we work in. They have
access to an electronic task list. If I have an action, then I am going to put that on my list to get me back
to that folder in order to do my work. One of the biggest benefits of an electronic task list is the ability to
sort and group and see things the way you want to see them. For example, I believe when I worked with
you, I thought I heard that you're kind of more of a project kind of a person. You kind of like to see your
things grouped in a different way, maybe by categories.
[00:14:57.620] - Chris
[00:14:58.320] - Debbie
I'm a due date girl. I like to see my things like what do I need to do today? And so when you begin to
create this electronic list, you have flexibility in the way that you see your work. Also, you're not going to
lose it. How many times have you lost a piece of paper that you couldn't find? That list is there? You're
not going to lose that list. You don't have to rewrite anything. You might change the dates, but you will
always have access to it. So there is a lot of power in that list. And one of the best things about that list is
think about when you go to your performance review at the end of the year, the quarter and you're having
to tell someone what you did for this year, you can now have a record of what you've done. You could
even print it out. And so there are so many benefits to trying to get first off, everything consolidated right
in one place and then having a list that you can use and work with based on the way you like to work.
[00:16:02.030] - Chris
And if I remember from your class, that was so many of us, our day is managed by what crisis or what
email just popped into our inbox and then we lose track of all the other things that had been going on the
day or the week before, basically. But this task list and organizing it that way just really help to prioritize
and let that drive your day and not being thrashed by these emails that is constantly coming in. So good
principle to apply there. And then finally, the fourth one is understand the tool that you're using. Now, I
know you specialize in Outlook, but what do you mean by understanding the tool that you're using?
[00:16:50.220] - Debbie
Well, I think we're all guilty of this. We get software. I'm thinking about Zoom. I need to really dig in and
learn more about that tool. But when you're given a tool to use, I guarantee you and even Microsoft has
quoted this less than 10% you use of the functionality of that tool that's there. And so understanding all of
the bells and whistles. And I have a funny story about that. I had a car for two years before I realized it
had an alarm system on it. So my son accidentally set it off. Now, I didn't know the features and benefits
of that card. So if you have this tool here to use every single day, it is worth understanding the shortcuts,
the tips, how to make it easy to use, and what it can do for you.
[00:17:47.770] - Chris
Yeah, and you're right. I think we just get right into our comfort zone. We know just enough to get our job
done. And then it's going to take a little bit of effort to learn a little more. We have to kind of do things a
little bit differently. But it is worth it as far as just really digging down into that tool that you're using. There
so great practices, so good filing system, having a good process, utilizing tasks to drive your day and
understanding the tool that you're using. It doesn't matter what system you're on, that's going to work for
any of those. Now, Debbie, is there any other great practices when it comes to email management for our
PMO listeners that you'd want to share with us today?
[00:18:30.710] - Debbie
Well, I think just like in life, anything that works well, you usually have discipline around it. You have a
routine around it. And when you get into that routine of how you want to manage your time and
information and emails, your day goes better. So I would say being organized is really about just knowing
what your process is and sticking to it, having reasonable expectations in our world today, I think because
we live in this fast paced world where people want instant answers, is that you can do a lot by helping set
expectations about how you communicate. And so that we're not frantic right all the time. Usually when
you answer an email too quickly, it's probably not a good idea. So just learning your routine and sticking
with it will help you, I think, manage everything well.
[00:19:33.410] - Chris
Yeah, and you are right. It's just like I learned a lesson many years ago myself. It may have been like ten
minutes before the end of the day and you get this blazing email that comes in. You feel like you just got
to respond right then and there, and you start hammering it out. And then the day ends, like in about ten
or 15 minutes and just wait until the next morning to send that email, let it sit overnight, then look at it in
the morning with fresh eyes. And every time I've done that, it's really basically waiting ten or 15 minutes.
But I've rewritten that email to be a much better email because of just having that patience and just not
firing it off at that point in time because it just came in. So that is really good advice. What are your
thoughts on? I hear some people, they say, well, I only only check my email at eleven in the morning and
four in the afternoon. Is that feasible? Is that reasonable?
[00:20:37.580] - Chris
What are your thoughts on that?
[00:20:39.040] - Debbie
Well, and here again, it's about setting the expectations. I have a business coach that I work with, and I
know that when I send an email to him that I'll get an answer at 04:00 in the afternoon or after, he doesn't
respond to emails all day long. Okay. And I've had clients who say, especially at an executive level, don't
send me an email. If it's really a crisis, pick up the phone and let me know. So helping people understand
the expectation of the answer of email. So, yes, I would say that sometimes comes from your leadership
team or your company culture of how that gets handled.
[00:21:26.750] - Chris
Right. Okay, so that's good. And I heard the example, too. It's just like I've got to respond every minute on
the minute. But then it's like, well, what if you're taking a flight somewhere, you're not going to be in the
office, you're not going to be replying for three to 4 hours and everything is fine and it works out just fine.
So just like you're saying, it's just kind of a good habit to get into there. What are your thoughts on C?
Seeing everybody on everything. What do you think?
[00:22:05.390] - Debbie
Well, that's a big issue when I'm working with people, especially coaching when you're working with
someone one on one. And the manager says, I've told them not to do this and they CC me on everything.
Normally that's when we set a rule, we have a folder called CC and all of them go in there because he
says if it's really an issue, I'm going to hear about it because he just wastes his time to do that. So when
you CC someone, just be sure that they either want to get CC's on that or that it's necessary that they get
it or reply all that's. Another. Sometimes you don't have to reply all and say, thanks. There's some email
etiquette that we didn't even get into today, that we have ideas about how you can help have some email
rules. But yeah. So reply and CC are sometimes big issues in the workplace.
[00:23:02.290] - Chris
Yeah. We could probably cut half of the emails we received down by not getting the thanks emails that's
been CC to everybody.
[00:23:10.710] - Debbie
[00:23:12.630] - Chris
Well, these have been some great points that we covered this episode here. I appreciate you being on
today. Now you've got a little bit of maybe a new journey ahead of you, maybe a new business you're
starting. And I'm using that word loosely because you've been doing this for a while. So you want to kind
of tell us a little bit about what you got going on and how people can get in touch with you.
[00:23:34.920] - Debbie
Sure. Yeah. I work for a company called DJ Consultants for about 21 years. And this company actually
was the company where we developed all this training and process and coaching. But the owner of the
company of DJ Consultants decided that it was time for her to retire. But she wanted us to keep going
with the things that meant something to her. And so she asked that we start a new company. And so we
started a company called Upskill and Win. And I have a business partner, Rebecca Kelly. And so together
we are going to continue providing the same great training and coaching that we've always done that
used to be with DJ Consultants. So you can reach us if you want to go to our website,
www.upskillnwin.com. You can email us at [email protected], or you can call me at 678-493-8913
and thank you, Chris, for having us here today. Thank you so much.
[00:24:40.340] - Chris
Yeah, it's been my pleasure. And again, I took your course. It's been a number of years ago, but it has
transformed the way, especially the use of tasks and the proper use of flagging. I'm not in a parade, but I
have learned how to categorize and make things where I can just retrieve anything anytime I need it
because I think, like you said, anybody can file, but not everybody can retrieve. And it is definitely a two
step process to go through that. So I appreciate all your help in that.
[00:25:15.650] - Debbie
And you just said the one thing that we always want to hear, I say obviously in the class or teaching and
say if I ever see you again, what I would love to hear from you is that you are still using the things that we
taught you when I worked with you. So, yeah, thank you. That's what always makes our day.
[00:25:36.040] - Chris
Well, I appreciate that very much as well. All right, Debbie, thanks for coming on today, and we will talk to
[00:25:42.630] - Debbie
All right. Bye.
[00:25:49.490] - Chris
Well, that was another great conversation on great practices and this time with Debbie Kirtland of Upscale
and Win. And here's some of the great practices that I gleaned from today's episode. First of all, she
talked about how important it was to have a good filing system. This was the example of Big Bird and
Sesame Street where one of these things is not like the other. So you want to make sure that you've got
your filing system set up where you can categorize and put whatever it is that's coming in to your email
into the proper places and not just being able to file it, but more importantly, being able to retrieve it later.
Next, she said it was important to have a good daily routine to do certain things with your email. So it
could be that first thing in the morning is when you check your email and then maybe you don't look at it
until the end of the day again. Or she gave the example of somebody that wasn't going to reply to emails
until after 04:00. So each situation is different but come up with a process that works for you and stick to
[00:26:55.370] - Chris
Third, she talked about utilizing tasks to drive your day and not so much your inbox and not even
necessarily your calendar because it is so easy to get knocked off track by the latest flaming email that
comes in and then the rest of your day is gone. So being able to use these tasks and categorize them,
she does it by due date. I know that I do it by category and then you can pull those tasks onto the
calendar and just drive it from there. But really, what is driving your day is your task list and not your
inbox. And then finally, deeply understand the tool that you're using. Maybe it's Outlook, maybe it's Apple
mail, maybe it's Gmail. Whatever it is, are you maybe only using 10% of the capability that it offers? She
had that example I liked about the car that she had for two years. Didn't even know it had an alarm until
her son set it off. So it's easy to do. Look up some online tutorials, get a book or two. You'll be amazed at
how much more you can do if you utilize those tools properly. And the final thing I really appreciated that
she just said is look, it's going to take discipline, routine and setting expectations.
[00:28:12.530] - Chris
Let people know that if it's an emergency, email is not the way to contact you, call you and then for the
others what's your SLA is it 2 hours to respond to an email, 8 hours next day. Whatever it is, make sure
that people know about that and then stick to your own expectations, setting and finally quit. C seeing
everyone with thanks. We all appreciate that reminder don't we? So again we appreciate Debbie being on
today and sharing some of these great practices with us and I know she would love to hear from you by
visiting her [email protected]. Do you have a great practice that you want to share? Well we
encourage you to jump onto the Pmoleader.com, click on community and then great practices and scroll
down to the bottom. You're going to see a form there where you can submit your name and idea and
someone will get back to you shortly. Thanks again for listening to this episode and keep putting great
practices in the practice.