MY TOP

TEAMWORK TIPS
How You Can Become The Most Effective,
Appreciated, And Happiest Strategic Assistant
®

To Your Entrepreneur
By Nicole Pitcher
 For six years, I’ve worked side by side with Shannon Waller,
Entrepreneurial Team Strategist and creator and coach of The
Strategic Coach® Team Programs. She calls me her Strategic Partner,
and I, of course, want to live up to that role in the best way possible.

Over my time at Strategic Coach®, I’ve learned a lot about

entrepreneurs, entrepreneurial companies, and, most important, how
to support an entrepreneur or team leader to do their best work.

Not to say that the road has been perfectly smooth! Shannon and I
have worked hard to be true to who we are as individuals and how
each of us best gets results — which, as I’ll explain later, is very different
from each other.

This is true in most successful entrepreneur or team leader/Strategic

Assistant® relationships because the natural, instinctive strengths and
talents of an entrepreneur can be pretty much the polar opposite of
ours!

This can make things a bit tricky at times, but understand why your
relationship can be tricky (which I hope to help with in this guide) and
be willing to work at it together, and you’ll create the most rewarding,
effective, and fun teamwork you’ll ever experience.

My idea for this guide came from my hope that by sharing the
strategies I’ve learned, implement, and live by — and that strengthen
Shannon and my teamwork and results — it might be useful to other
Strategic Assistants in entrepreneurial companies who are likely
experiencing the same things I do in this role.

Great teamwork is the key to success for your entrepreneur and for
you, and I wish you all the best in creating yours together!

Nicole

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 My Top Teamwork Tips

PART 1
5 TIPS FOR MAKING THE MOST OF
YOUR ENTREPRENEURIAL TEAMWORK
Most successful entrepreneurs are creative doers who think fast, act fast,
and deal with any fallout, which will inevitably happen, when it happens.
A successful Strategic Assistant, on the other hand, is a thinker, a
planner, a designer, and a follower of systems they put in place to create
the greatest efficiency and productivity for both their entrepreneur or
team leader and themselves.

These are almost diametrically opposed working styles!

It’s interesting in our experience at Strategic Coach, working with

thousands of successful entrepreneurs in hundreds of different
industries, that when it comes to hiring a Strategic Assistant, a lot of
entrepreneurs look for and hire someone just like themselves. Their
thinking is that they’ll get along well and work well together. Fair
enough — but what actually happens is that nothing will get done and
chaos will ensue.

At Coach, we also know that every entrepreneur will do their best work
when they’re supported by a partner who has the complementary skills,
talents, and natural strengths necessary to do what the entrepreneur
themselves can’t or won’t do.

From my six years of working in this type of relationship with Shannon,

here are my top tried-and-true tips Strategic Assistants can use to
develop a working relationship that honors each of your strengths and
non-strengths with respect.

You’ll discover that this type of teamwork will always lead to greater
alignment, productivity, and results — minus the drama that will come
from a relationship where strengths and non-strengths are too similar or
badly mismatched.

TIP Ask direct questions — who, what, where, when,

#
1
why.
Those of us who will thrive in the Strategic Assistant role, by our very
nature need context to do our best work. This might not necessarily be

3
 something your entrepreneur needs themselves or will be able to offer
up. It’s up to you to ask.

You are the “who” your entrepreneur is counting on to take care of all
the “hows” they’re delegating — or should be delegating — to get the
best result.*

You need to know who, if anyone, is going to be involved with you on

the project, what the goal is, where the project or event will take place
(Are travel arrangements needed? Does a boardroom need to be booked
for a meeting?), when it’s due, and why it’s important.

The Strategic Coach tool we immediately reach for to understand the

“why” is The Impact Filter™, which I’ll talk more about in Tip #4 below.
Ask your entrepreneur or team leader for an Impact Filter on any
project, and you’ll have the best context to understand clearly what your
entrepreneur’s expectations are — no guesswork involved.

If you still have any uncertainties, I encourage you to communicate them

at this point. What would make you feel more confident moving forward
with this project? Is it a deadline, your entrepreneur’s help with a certain
area, and so on.

*Recommended reading for both you and your entrepreneur:

WhoNotHow by Dan Sullivan.

TIP Ask to sit in only at the start and end of

#
2
brainstorming meetings.
This has been a game changer for Shannon and me. In the past, I would
sit in brainstorming meetings with her and other team members who
were discussing brand-new projects or ideas.

Many of them would come up with a lot of new ideas at a fast pace,
without the need to think things through sequentially. I’m the exact
opposite. My natural tendency is to hear an idea and immediately start
envisioning what the next steps would be and any obstacles that may arise.

The others in the meeting would already be on their tenth idea while I
was still thinking through the first one, and I would leave the meeting
feeling overwhelmed, frustrated, or bored.

4
 My Top Teamwork Tips

With some thought, I realized that the most beneficial use of my

strengths in these types of brainstorming meetings is at the beginning
of the meeting when I help to set up the context and remind everyone
what we’re there to achieve (for example, a new workshop design by “x”
date), and toward the end of the meeting when I can prompt them to
make a decision and decide on next actions.

Now, I only schedule myself into the first five and last ten minutes of any
brainstorming meeting, and I use the in-between time that I gain on
tasks that make better use of my mental energy.

TIP Complete The Communication Builder exercise with

#
3 the person you’re supporting.
During my first few months at Strategic Coach, one of the first tools that
I completed with Shannon was The Communication Builder. It takes
just minutes to complete, and it’s actually fun to discuss with each other.

By the end of the exercise, you’ll have learned each other’s preferred
methods and times of communicating, as well as the least effective ways
to communicate with each other.

For example, Shannon and I discovered that neither of us is a morning

person, so we prefer to ease into our mornings with light conversation
over coffee or tea to get us fully energized for the day’s work.

I also learned that Shannon likes to give voicemail communication

but prefers not to receive voicemails, and Shannon learned that after 4
p.m. isn’t the best time to ask me to make a change of plans, as I will
have used up all of my spontaneous energy by this point. For example,
Shannon may decide that she’d like to reschedule a meeting on the
calendar for next week — much better to communicate that the next
morning!

TIP Accompany all new ideas with an Impact Filter.

#
4

As I mentioned earlier, one of the essential tools at Strategic Coach is

The Impact Filter, which is a great way to facilitate clear and direct
communication between team members. Entrepreneurs and team
leaders in our workshop programs are encouraged to capture all their
new ideas in the form of an Impact Filter, which will help them get clear
on the why of a project/idea and what will need to happen in order for it
to be successful.

5
 Dan Sullivan, founder of Strategic Coach and creator of The Strategic
Coach® Program, completes an Impact Filter before every meeting and
every project he’s involved in. Dan has told team members many times
that any of his ideas not accompanied by an Impact Filter should be
considered brainstorming, and no action needs to be taken until an
Impact Filter is done.

When the person you’re supporting tells you about a new idea/project
they’d like to get started on, don’t be afraid to ask for an Impact Filter.
This will help you to see the context behind their thinking and where
your natural strengths might be helpful in making it a reality.

This also works in reverse — when you have a new idea to communicate
to them, you’ll get not only them but yourself clear with an Impact Filter.

It’s best to send an Impact Filter ahead of any meeting scheduled

specifically to discuss the new idea. This gives the other person time
to reflect on it and prepare any questions they may have, which is
especially helpful when someone like me is involved in the idea! I need
time to digest, think, and come up with ideas on how I can help make it
work.

TIP TIP #5: Have a “partner, not employee” mentality/

#
5
mindset.
There are many titles given to people in supporting roles in a company —
Strategic Assistant, Executive Assistant, Administrator, Coordinator,
Scheduler.

Shannon refers to me as her Strategic Support Partner and was insistent

from day one of our working together that she was not looking for
someone she would have to manage, but instead someone who would
help manage her.

We’re both very aware of our individual strengths and non-strengths, and
communicate them openly with each other. We quickly realized what
each of us is good at and what we need in terms of support from each
other in order to achieve our goals, and we work to ensure that we both
stay on our side of the clearly delineated line. For example, I work with
our team on the “backstage” to prepare Shannon for delivering value to
clients on the “front stage.”

6
 My Top Teamwork Tips

How To Plan And Lead A Successful Strategic

Planning Meeting
I plan, organize, and run Shannon and my out-of-office Strategic
Planning Meetings every six to eight weeks. This two-hour lunch meeting
is my “baby” and is designed specifically to keep Shannon and me
aligned and on track over the long term, which can be difficult if you
don’t have a big-picture plan.

It’s a perfect example of my role in “managing” Shannon so she’s in the

best position to do her best work. For her, it’s a welcome opportunity to
take a break from always being in charge and enjoy having me lead the
way; for me, it means I get to shine at what I love to do.

Importance? In our day-to-day, Shannon is focused on the day at hand

— her scheduled back-to-back meetings, calls, and workshops. Though
I’m also focused on what has to happen daily, the bigger picture of what
lies ahead is always on my radar. The Strategic Planning Meetings give
Shannon the chance to sit back, relax, and allow me to be in charge as
we both get a refresher on what lies ahead for us over the long term.

Biggest difference they make? Our weekly in-office meetings only allow
time to work on short-term projects and clean up messes. But the
Strategic Planning Meetings give us an opportunity to:
• Celebrate our progress since the last meeting.
• Get aligned on upcoming projects.
• See what needs to get done to accomplish the goals we’ve set.
• Plan for the future.
• Focus on the big picture.

Ideal outcome? Uninterrupted, we connect on and prioritize our goals

and strategic projects, and figure out key actions.

Worst result if we don’t meet? We get out of alignment on priorities,

actions, and upcoming projects. Lack of communication leads to
breakdowns in our working relationship and unrealistic expectations.

Best result if we do? We feel confident, organized, and prepared for all of
our upcoming projects. We communicate and work through any messes
or challenges.

7
 Our success criteria for the meeting?
• Start with a Positive Focus® — each of us identifies our own top
achievements since the last meeting.
• Review our Strategic Projects list and debrief on a few completed
projects.
• Bring two copies of the agenda, the previous Strategic Projects list, the
upcoming Strategic Projects list, and needed Coach tools (e.g., The
Strategy Circle®).
• Review upcoming Strategic Projects and decide on results, who needs
to be involved, and action steps to complete.
• Keep an ongoing to-do list throughout the meeting for both of us
(photocopy for Shannon after meeting).
• Before meeting, ask Shannon if there are any new tools she’d like us to
complete together (e.g., The Communication Builder is great for your
first meeting).
• Between meetings, keep an ongoing list/folder of ideas to discuss and
tools we want to work on next time.
• Schedule meetings in both our calendars six months to a year in
advance.

PART 2
5 TIME MANAGEMENT TIPS DESIGNED
FOR ENTREPRENEURS AND THEIR
TEAMS
TIP
#
1 Start your week off with a review of the week ahead.
The best thing you can be is prepared for this meeting. The more
prepared you are, the more you’ll get done, and the more actionable
steps will result. Progress!

These are some of the steps you can take to make this happen:
• Print any relevant reports, schedules, and anything else that’s needed
ahead of the meeting.

• If possible, try to come in a few minutes earlier than your entrepreneur

or team leader so you can get settled and check for any new changes
or urgent requests that might have come in over the weekend.

8
 My Top Teamwork Tips

• Review any outstanding or urgent emails or correspondence. Ask how

you can help these along.

• Once you’ve gone through everything that requires an action, make a

prioritized to-do list with your entrepreneur.

Protect this key meeting! Should vacations, commitments, or travel fall

on a particular Monday, be sure to schedule the Tuesday as soon as
you can.

TIP Keep a current short-term and long-term view of the

#
2 calendar at all times.
Your entrepreneur or team leader is likely focused on the most current
and pressing commitments on their calendar. They’ll rely on your
planning ability to help them prioritize and get focused on what lies
ahead at the appropriate time.

• Stay well informed of any calendar changes that may affect the
immediate future, and tell your entrepreneur immediately. They may
have their time and attention focused on an important meeting or
client call that’s coming up, so if it needs to be canceled or rearranged,
let them know as soon as possible so they can shift their attention
elsewhere.

• Frequently review the next month or so ahead so you’re confident

about what’s coming up. Your entrepreneur or team leader may need
help with prompts about upcoming deadlines, travel, and so on.
Keeping a longer-range view on their calendar, you’ll also have some
time to pull together anything they may need ahead of time without
an urgent rush.

• Spend a day or two each month looking at the year ahead (the next 12
months). This is a good time to double-check that there haven’t been
any changes to the calendar. For example, your entrepreneur may have
added a vacation without looping back to you, or a new event/trip may
have been added.

When you need to make changes to commitments that are scheduled

this far in advance, it can be complicated if it involves other hard-to-
schedule people. The sooner you can work out the changes, the better.

9
 For example, I work with Dan Sullivan and Babs Smith’s Strategic
Assistant to schedule a year out anything that involves Shannon, Babs,
and Dan.

TIP
#
3 Plan your Free Days™ as far in advance as possible.

At Strategic Coach, our entrepreneurs learn a new time management

system specifically designed for entrepreneurs. It has three different
types of days: Free Days™, Focus Days™, and Buffer Days™. Free Days —
the time away from work that most entrepreneurs think they can’t take
— are the foundation. After all, how productive can you be when your
brain is overworked and tired, and as a result, has lost any ability to think
clearly and creatively?

In my case, Shannon lives by this Entrepreneurial Time System® and has

all three types of days in her schedule. Free Days are a must for her to
rejuvenate and refresh, so we schedule those first.

If you’re supporting someone with a busy calendar, it’s in their best

interests to put their Free Days in the calendar for the next year
(entrepreneurs are taught this concept quickly upon joining Strategic
Coach). Once you have an idea of when they’re taking Free Days, look at
scheduling your own.

Discuss with your entrepreneur what times of year would be best for you
to take longer vacations (1 or 2 weeks). Here are some things to consider:

• Often, it makes sense for you to try to align your scheduled time off
with theirs, as it may be a slower time for your business.

• Sometimes, they would rather you take time off when they’re in
the office so there’s always one of you around to deal with urgent
correspondence.

• Another great time to take your Free Days may be when they’re away
on business travel and out of the office for an extended time.

• Occasionally, you’ll need to take time off that isn’t ideal (for example,
your sister’s destination wedding, an important medical appointment,
etc.). If you know far enough in advance about these, you can put back-
ups and support in place for your absence.

10
 My Top Teamwork Tips

We all have to take unexpected Free Days due to illness, emergencies,

delayed travel, weather, and so on. When you have some time with your
entrepreneur or team leader, discuss back-ups you can put in place now
for these types of Free Days.

Perhaps you have a buddy at the office who can fill in as support when
you aren’t there, or you can share access to important information with
your entrepreneur or team leader and show them how to find it when
you’re away.

TIP
#
4 Space out Focus activities.

The Entrepreneurial Time System also includes Focus Days, where the
entrepreneur has scheduled and protected time to focus only on their
top three money-making activities.

Your entrepreneur may have back-to-back meetings or calls on their

Focus Days, and a long to-do list that results from each of these Focus
activities. The best way to support them is to make sure they have space
between each activity.

The benefits of a little flex time in between meetings, calls, or activities

are many: built-in time in case of any delays (travel, a call goes longer
than expected); they have time to run to the restroom, refill their
coffee, or grab lunch; you have the chance to communicate anything
important/urgent that may have popped up; and they have time to
“download” the follow-up to you.

I try to schedule 15 to 30 minutes of follow-up time for Shannon after

each call/meeting/Focus activity (depending on the event). During this
time, we’ll connect, she’ll give me a list of next actions while everything
is still fresh in her mind, and I can help make sure they get done. If I
happen to be unavailable during this follow-up time, Shannon will write
out the to-do’s in an email or put them into one of our shared Trello
Boards, an online project management tool we love.

TIP Schedule an end-of-week wrap-up with your

#
5 entrepreneur/team leader.
These are some of my key to-do’s for a Friday that you can try out with
your entrepreneur:

11
 • If possible, meet to review what went well over the week (we use a
much-loved Strategic Coach tool called The Positive Focus), what
didn’t get finished and is still outstanding, and any new items/ideas
that either of you have to communicate to the other. We also take a
quick glance at next week.

• Spend some time printing anything you may need for your Monday
meeting (see page 8) so you’re ready to go.

• This is the time to ask your entrepreneur about any new ideas or
changes that may have bubbled up over the week so you have time to
digest and think about them over the weekend.

Make sure that you communicate an understanding that you won’t be

expected to act on these new ideas right away (i.e., Friday end-of-day!).
If you’re like me, most of your last-minute problem-solving energy was
used up by Wednesday, or at least by lunch on Friday, so you will resist
any drastic changes at that moment — but you can listen and take it in,
and come back rested and ready to take action on Monday.

PART 3
HOW TO MAKE THE BEST USE OF
YOUR FOCUS AND BUFFER TIME.
I’ve talked about Free and Focus Days, but there’s a crucial third day
in The Entrepreneurial Time System — the Buffer Day™. This is time to
conquer clean-ups, new learning, and any delegations.

For Strategic Assistants, a whole day to “Buffer” is probably highly unlikely.

But that doesn’t mean you can’t benefit from this time management
strategy by scheduling time periods during the day to Buffer!

When your entrepreneur or team leader

focuses, you Buffer; when they Buffer, you get
Focus Time.
• Mondays and Fridays are great Buffer Days for your entrepreneur, so
they’re likely your best Focus Time. That leaves the remaining three days
of the week to schedule the Buffer Time that will work best for you.

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 My Top Teamwork Tips

In my case, Tuesdays and Wednesdays are usually the days that Shannon
is doing client-facing activities, so they’re when I schedule Buffer Time or
uninterrupted Focus Time at my desk.

• Certain times of the day might be best. Figure out what will best work
for you, and schedule and protect that time for working on your Buffer
activities.

For me, as well as a few other Strategic Assistants at Strategic Coach,

9 to 9:30 a.m., 1 to 1:30 p.m., and 4:30 to 5 p.m. are usually protected
Buffer Time.

• When it comes to Focus Time, the best time to take it is generally

when your entrepreneur or team leader is on a Focus Day™, traveling
for work, or on vacation.

As with Buffer Time, this will likely be portions of the day when you can
shut yourself away to work on detailed, time-consuming tasks or larger
projects that can normally be difficult to make any headway on.

You could send an email to your co-workers and/or place a Focusing

sign on your door or desk to let others know you’ll be focusing from 9:30
to 11:30 a.m., for example, but that you’re open to calls and requests
after that. Emergencies notwithstanding, you’d be surprised how well
this works. People can be very respectful of your time when they’re
nudged. You just have to put it out there!

As satisfying and important as Free Days and Buffer Time can be, Focus
Days are essential. I know that it can sometimes be difficult to wrap your
mind around defining your Focus activities if you think of them in terms
of your top three money-making activities. Yes, your entrepreneur/team
leader is more directly responsible for bringing money into the company,
but your work that supports them is of great value.

Even entrepreneurs can be unsure of their top three money-making

activities until we coach them to think about it this way: If someone
took away all of your work activities, what is the first one you’d say
was most crucial, then the second and third? Your Focus activities are
not only important in and of themselves, they’re important to your
growth and satisfaction with what you do. They benefit everyone — your
entrepreneur, the business, and, most important, you.

13
 Some of Nicole’s Buffer Time activities:
Clean-ups:
• Putting away files and paperwork into the appropriate places and
shredding old information or paperwork that is no longer needed.

• Replying to non-urgent email requests, deleting old email messages

for Shannon and me, or organizing them into the appropriate folders.

• Updating Trello Boards with information needed; for example, adding

due dates to projects or notes from a client call.

• Reviewing the calendar for upcoming projects as well as long-term

projects and making a prioritized to-do list.

• Requesting transcripts of calls and recordings from online resources

(Rev.com) to be used for future marketing and design projects.

New learning:
• Researching improvements and new ideas to better our work flow and
communication. For example, logging in to the Gallup organization
website to download the new 34 CliftonStrengths® report, or watching
a tutorial about how to fully utilize Trello for project management.

• Downloading the latest software update for a computer program.

• Completing a Strategic Coach strategizing tool like an Impact Filter

on a new idea I’d like to communicate to the team or an Experience
Transformer® on a project or process I think has room for improvement.

• Business travel days.

Delegations:
• Connecting with other team members to check in on current projects
I’m responsible for managing and move them along.

14
 My Top Teamwork Tips

Some of Nicole’s Focus Time activities:

• Printing and presenting weekly/daily calendars and reports to Shannon.

• Scheduling meetings, travel, and workshops as needed.

• Planning, organizing, and leading the Strategic Planning Meetings

Shannon and I have every six to eight weeks.

• Coordinating Onsite Workshops coached by Shannon and our other

Team Coaches for our entrepreneurial clients and their teams, usually
at their office.

• Supporting Shannon at Onsite Workshops by tracking to-do’s, taking

notes, building relationships with clients, and sending detailed
follow-up notes to their teams.

• Tracking expenses, collecting receipts, completing AMEX monthly

allocations, and creating expense invoices.

• Prompting Shannon and our design colleague Cathy about upcoming

design project deadlines and communicating progress to our team.

• Managing Shannon’s commitments, due dates, and to-do lists,

ensuring that she has the time and resources she needs to complete
them and honor her commitments.

• Organizing and executing various internal team-building programs at

Coach, including quarterly book clubs with Dan and an annual One-
Year Planner challenge.

I know that the tips and ideas I’ve shared with you in this guide
might be a different way of doing things, but I have confidence
that if you (and your entrepreneur or team leader) start with even
one or two that you’re excited about trying, you’ll notice a marked
improvement in how you work together.

It takes time, and it takes work, but the increase in productivity and
results — and the rewards you both come away with — more than
make up for the effort invested in the beginning.

Here’s to your teamwork success!

15
“Great teamwork is the top
multiplier of results in any
entrepreneurial business.”
DAN SULLIVAN

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Strategic Coach :
®

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www.strategiccoach.com

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