5 Strategy Exercises For
STRATEGISTS
One of the biggest problems for strategists is that they don’t get enough
chances to practice the skillset of strategy. In this video I’ll share five strategy
exercises to help you improve your strategy skills.
But first let me tell you why practice is so important for strategy. A lack of
practice nearly got me kicked off the PlayStation pitch team at 2AM the night
before the biggest pitch of my life.
I had made it onto the final team who flew out to San Francisco to pitch
PlayStation, we had gone through the final run through of the pitch. The
nerves were getting to me and I was messing up my strategy slides.
The CEO and CCO came over to me and said they were going to cut me from
the team, because I hadn’t had enough practice pitching strategy to clients.
I was devastated, I told them that I would stay up all night and get this perfect.
I realized in that moment, we are expected to be perfect but we never practice
our craft.
They gave me a chance and I ended up making the team and we won the
pitch and I made some of the best work of my life.
Practice has not only helped me, running the Planning Dirty Academy for the
last 3 years I’ve noticed the strategists who practice are the ones who have
transitioned into world class strategists. A great example of that is an
Academy member who went from an account manager to a strategist, Tyler
Koke. He practiced retrofitting strategies for iconic campaigns, you can check
out his Ikea one here.
That is why I created a guide of ten exercises that every strategist should
practice. The following are five of those exercises you can practice either by
yourself or in a group. The five exercises Word Golf, Warhol’s Words, Ladder
Builders, Brief Surgery, and Opening Moves all test a different skill set needed
in strategy.
Word Golf
What is it?
Exercise where you’re trying to use as few words as possible to make a
strategy.
Why is it important to practice?
One of the most important skills for strategists is to be brief, we need to be
very conscious of how many words we use, as we are trying to keep the
attention of our audience. This exercise demands that you reduce the word
count without reducing the meaning.
What are the steps you take?
1. Reveal a paragraph that has been written, this could come from a deck or an email you have
2.
3.
4.
5.
written that week or you could take from my collection of paragraphs that need to be
shortened. You create PAR by working out how many words you used in the rewrite. E.g
when you rewrote the sentence it was 30 words instead of 50 words, that then becomes par.
You then put 30 seconds on the clock and the strategists have to rewrite the sentence with
the least words possible
At the end of 30 seconds the strategist responds back with their sentence and word count
You have to decide whether the sentence makes sense and then how many words above or
below PAR they are. E.g Someone with 27 words would be -3 points, 35 words would be +5
At the end of the 9 exercises, the person with the lowest score is the winner.
How long does it take?
Each round takes about 2 minutes (for 2 people). 9 holes of word golf will take
you about 20 minutes.
Hints?
You never need to write prepositions (I, WE, YOU), you never need to use the
word ‘just’
Example of the exercise
WORD GOLF - HOLE 1
WORD COUNT 43 - PAR 26
After the launch of Ticketmaster Connect back in December 2021, our ticket
trajectory was not met. We’re competing against a serious local ticket hawker
(SLTH) that only operates in local areas. SLTH currently does 400K Tickets/
Week while we do 15K Tickets/ Week.
ANSWER
Launching in December 2021, Ticketmaster Connect's ticket trajectory has not
been met, currently 15K Tickets/ Week. Competition, serious local ticket
hawkers (SLTH) does 400K Tickets/ Week.
So in this one, the count is 26 words so my score would be 0 as the PAR is 26.
Warhol’s Words
What is it?
This is a game to see who can make the most memorable strategy. The tool
you have at your hands is the ability to paint with words. There are two types
of words in the world, visual words which have an image attached to them
and verbal words which have no image attached.
This game needs to be played in groups of three or more.
Why is it important to practice?
Making a strategy that sticks in people's mind is essential to the job. One of
the best ways of doing that is using visual words, which paint pictures in
people’s braids.
What are the steps you take?
1. Come up with a list of one sentence strategy statements that you’re trying to get across. This
can come from you or you can use this list attached.
2. You then put 1 minute on the clock and the strategists have to rewrite the statement using
3.
4.
5.
6.
visual words or an analogy to make it more memorable
You give all the answers back to the leader and they read out the answers
The group then votes on which answer they think is the best one
Everyone vote is a point towards that strategists
The first strategist to 10 points wins
Hints?
Alliteration, analogies and picturing words
How long does it take?
20-40 minutes depending on how many strategists you have.
Example Of Exercises
Certain songs can become a positive emotional touchpoint for fans of their
favoured football club.
ANSWER
Every Club Has Their Perfect Pitch Songs
Songs are the 12th player of a team
Lead singers are you new lead strikers
Kicking Goals With Sound
Soccer Song Birds - Every club has their iconic song.
You would vote for the statement that best encapsulates the spirit of the
original statement
Exercises 2
The complement of alcohol and caffeine that is achieved in an Espresso
Martini creates the ideal state for consumers on a night out.
ANSWER
Shaken and stirred - the mix of caffeine and alcohol
Head racer, body chaser - the mix of caffeine and alcohol
Cocktail of moods
You would vote for the statement that best encapsulates the spirit of the
original statement
Ladder Builders
What is it?
An exercise where you put together the rungs of the benefit ladder.
Starting with the top rung (the emotional benefit) or bottom rung (product or
service) and you then have limited time to try and fill out as many ladder
rungs as possible.
Why is it important to practice? What skill does it help you improve?
Ladder Builders gets you comfortable with using the benefits ladder and helps
you to get comfortable with emotional benefits without the pressure of a real
brief.
Practicing ladders helps to show that there is not one answer to a benefit
ladder. The benefit ladder is used to help come up with the creative brief and
strategy on a page, consumer goal. It also helps you to create the messages
for the different levels of the comms framework.
What are the steps you take?
1. Start with either a product or service at the bottom of the ladder or a emotional benefit or
brand tagline at the top of the ladder.
2. Then it is the job of the strategists to come up with three different ladders filled out with the
3.
product or service, the features, functional benefits and emotional benefit for that product.
You have five minutes to write out as many benefit ladders as you can?
Pass the ladder to a partner and then give each other points on how many filled out ladders
you both create
Hints?
It is always easy with a definition of the rungs of the ladder and some
examples.
Product and service - Is anything that you could buy that would solve for the
problem at hand
Features - The distinctive attribute or description of the products, these
attributes help to solve a problem.
Functional Benefit - How it helps someone in that moment overcome a
specific problem. Ask yourself, why is this feature so important?
Emotional Benefit - The higher order desired state that comes from the
problem being solved in that moment, it is usually benefits and goals that sit
on a day to yearly basis. Ask yourself, why is solving this problem in the
moment so important?
If you are looking for more emotional benefits, you can download my 24
consumer goals cheat sheet which has a list of them.
How long does it take?
30 minutes
Example of exercise:
Bottom of the benefit ladder
Strawberries
Divorce Lawyer
Impressionist Painting
Headphones
Cup of Tea
Top Ladder Rung
Tranquility - Feeling relaxed
Individuality - Feeling unique, special or different
Material Gain - Avoiding the loss of money or material possessions
Understanding - Engaging in activities involving original thinking or novel or
interesting ideas
Belongingness - Avoiding feelings of social isolation or rejection
ANSWERS
For the first example let’s put strawberries as the bottom rung on the ladder.
Then work up from there.
Bottom Rung - Strawberries
Product/Service - Strawberries
Feature - Easy to transport
Functional Benefit - Perfect for a picnic
Emotional Benefit - Feelings of joy and well-being
Second ladder might be;
Product/Service - Strawberries
Features - Natural source of sweetness
Functional Benefit - Eat sweet foods that aren’t bad for me
Emotional Benefit - Feeling healthy
Third ladder might be;
Product/Service - Strawberries
Features - Pick strawberries from the farm
Functional Benefit - See that the food is all natural
Emotional Benefit - Connection With nature
Now let’s look at an example of when you start at the top rung;
Top Rung - Exploration - Satisfying one’s curiosity about meaningful
events (Exploration)
So we might land on Museums playing this role. So we would work out the
rungs in between for this.
Emotional Benefit - Satisfying one’s curiosity about meaningful events
(Exploration)
Functional Benefit - Understand how past events impact today
Features - Collection of artefacts that changed the course of history
Product/Service - Museums
Second product or service might be a Therapist
Emotional Benefit - Satisfying one’s curiosity about meaningful events
(Exploration)
Functional Benefit - Help you untangle what is going on deep in your head
Features - Trained professional in human psychology
Product/Service - Therapists
Third product or service might be a Podcast.
Emotional Benefit - Satisfying one’s curiosity about meaningful events
(Exploration)
Functional Benefit - Understand an issue from multiple perspective
Features - In-depth interviews with experts
Product/Service - Podcast
Creative Brief Rewind
What is it?
Share advertising campaigns that you admire and then try and write the
creative brief for that specific spot.
Why is it important to practice?
It’s important to practice writing the key documents of a strategist without the
pressure of a real client.
This also helps you see what the different briefs would look like for great work
and how they differ from the current briefs that you are writing.
What are the steps you take?
1. Find a campaign or advertising spot that you like
2. Play the spot for the strategists
3. Give them the format that you want them to respond in e.g your companies creative brief
4.
5.
formula or Get/Who/To/By
Give them 5 minutes to work out what is their favourite
Discuss as a team which one was your favourite response
Hints?
If you want an easier version of this, then you can also give the strategists the
PR release too as the client will talk about what the goals and problems of the
campaign.
If you are struggling for great campaigns to use, check out the Cannes Lion
Winners
If you need a refresher on how creative briefs are written you can check out
the free mini course that I have on writing creative briefs.
How long does it take?
10 minutes per campaign that you analyze.
If you want an example of this exercise check out my videos on creative brief
rewinds for Cheetos, Extra Gum and Hinge
5 Step Brief Surgery
What is it?
Share client briefs and see how strategists would go about diagnosing the
brief and get the strategist to write down what is missing from the brief.
Why is it important to practice?
This improves your response time on looking at a client brief and working out
the gaps that you have and information that you need from a client.
What are the steps you take?
1.
2.
3.
4.
Give the team a client brief
Give them 5 minutes to dissect the brief
Get participants to report back what was missing from the brief.
Extra points for how they would ask for that information.
Hints?
It’s important that you have a structure for the output that you’re creating. For
example, having a strategy on a page as your final output makes it easier to
understand what information is missing from the brief.
If you do not have a company template for how to write a strategy on a page
then you can look at the video on the nested Strategy On A Page document
here.
If you want more examples of client briefs to practice on, you can sign up to
the Planning Dirty Academy.
How long does it take?
10 minutes per client brief
Opening Five Moves
What is it?
Give strategists hypothetical situations and then get them to tell you the first
five moves that they would make after receiving that information.
Why is it important to practice?
This helps to get younger strategists who are used to taking orders to now
start to flex their muscles in making decisions.
Role playing common scenarios that strategists find themselves in is
important practice to help them navigate those situations in future.
If you are doing this in a group you often find that they will get more
information about how others would approach that same problem which can
be beneficial for other strategists in the room.
What are the steps you take?
1. You share the hypothetical situation with the strategists
2. Then ask them to write down the first five moves that they would make when they hear this
3.
4.
information?
You would give them 5 minutes to write their responses
The team would then share how they would respond to this information
Hints?
When you are writing out the hypothetical situation, make sure to give a
timeframe and a budget that they have to work with.
Think about all the common questions that you get asked as a strategy leader
and then respond to that.
You are not expecting them to do the work but expecting them to show you
their process.
The important thing is that everyone writes down their answers but when it
comes to the sharing section you want to hear from the more senior members
of the team as they have the most experience and junior strategists can learn
from them.
If you need more hypothetical situations, I have a bunch of them in a 10
strategy exercise guide that you can use.
How long does it take?
15 minutes.
This is depending on how many people you have in the group.
What is Strategic Planning?
In simple terms, strategic planning is the process of setting
objectives and developing a plan to achieve them. Having a
good strategic plan helps your employees understand their
responsibilities. So, they know how their contributions aid in
the company’s achievements. Ultimately, this facilitates the
alignment of their efforts with the organization’s vision and
objectives.
10 Strategic Planning Team Building
Activities for Your Employees
Here are some amazing activities to develop the strategic
planning skills of your employees.
#1. Brain Mapping
Brain Mapping is a team building activity that encourages
collaboration between team members while creating
effective solutions.
Time: 30 minutes – 1 hour
Materials: Computer, Whiteboard/Paper, and Markers
Participants: 2-10 people
Instructions

Each participant should come up with ideas on how to
solve a problem or reach a goal in the company. For
example, how can a company increase customer satisfaction?

The team should then map out all these ideas and
create strategies to make them happen.

Participants can draw the solutions on paper/
whiteboard, or use computers for more detailed plans.

Once the mapping is completed, they can discuss their
plans with others, and come up with the best solution.
Debrief
During the debrief, you should identify any areas of
improvement for the team and recognize their successes.
Encourage creativity to help foster collaboration between
team members.
#2. Fish Bowl
The objective of this exercise is to encourage open dialogue
between team members while creating innovative strategies.
Time: 30 minutes – 1 hour
Materials: Fish Bowl/ Container, Paper, and Markers
Participants: 4-8 people
Instructions

Each participant should put their ideas into the fish
bowl or container.

The facilitator should ask each participant to take
turns and explain their ideas.

Next, the facilitator can draw the solutions on
paper/whiteboard, or use computers for more detailed
plans.

After each idea is discussed, the team should come up
with a collective solution that benefits everyone.
Debrief
During the debrief, identify any areas of improvement and
recognize effective collaboration between team members.
Encourage feedback to create a safe environment for open
dialogue.
#3. Collaborative Goal Setting
This activity encourages employees to set goals for the
organization and develop plans to achieve them.
Time: 45 minutes
Materials: Post-it notes, Markers, and Whiteboard
Participants: 4-6 people
Instructions

Divide the participants into smaller teams.

Give each team a goal or initiative to focus on. For
example: “Develop strategies for increasing customer
engagement”.

Each team should brainstorm potential strategies for
achieving that goal. Then, they can analyze the merits and
demerits of each strategy, and decide on the best ones.

Finally, let them present their strategies to the other
groups.
Debrief
In the debrief, discuss how the team worked together to
develop goals and strategies, as well as any new ideas or
perspectives that arose during the activity. Celebrate
successes and brainstorm solutions for potential challenges
encountered.
#4. Elimination Match
In this exercise, the participants should use their strategic
planning skills to complete some tasks before the opposing
team.
Time: 30 minutes – 1 hour
Materials: Set of cards with individual tasks related to
strategic planning
Participants: 2 teams of 4-5 people each.
Instructions

Divide the participants into two teams of equal size.

Each team will receive a set of cards that represents a
specific task related to strategic planning. They can be
creating a budget, developing a marketing plan, identifying
potential risks, etc. As the facilitator, you should provide
further instructions to the teams such as the specific
requirements for each task or any time limits.

Now, the teams must try to finish the tasks as quickly
as possible. After completing a task, they must place the
respective card on the table. The first team that completes
all the tasks will win the game.
Debrief
Discuss how teams used strategic planning skills to identify
opportunities, create plans, and manage risks to complete
the tasks quickly. Furthermore, participants should evaluate
what strategies could have been employed differently in
order to improve their performance.
#5. Futures Wheel
The goal of this activity is to help team members explore
potential strategies for different scenarios.
Time: 20-30 minutes
Materials: Large poster board or whiteboard, markers
Participants: 6-10 people
Instructions

Ask the group to identify a goal they would like to
achieve in the future.

Each group member lists out 3-5 different steps
necessary to reach that goal.

Now, each group can draw a circle in the center of the
poster board or whiteboard and label it with their goal. Also,
they can draw a series of circles around the first one and
label them with each step necessary to reach that goal.

Then, they can discuss potential strategies that could
be implemented at each step to make progress toward the
end goal.
Debrief
As a facilitator, it’s important to ensure everyone
understands the goal and the steps necessary to reach it.
During the debrief, you should check in with each group
member to make sure they understand how their individual
strategies contribute to the larger plan.
#6. Lost at Sea Survival Game
This activity encourages employees to strategize and work
together to survive in an imaginary “lost at sea” scenario.
Time: 45-60 minutes
Materials: Imaginary items such as a fishing net, a flare gun,
a water container, etc.
Participants: 6-10 people
Instructions

Divide the participants into teams with an equal
number of members in each.

Ask the teams to envision themselves lost at sea and
present them with a set of imaginary items. Some examples
of items include a fishing net, a flare gun, a water
container, etc.

Give each team a few minutes to plan how they would
use their resources in order to survive until help arrives.

After the allotted time, have each team present their
strategies to the other teams.
Debrief
During the debrief, it’s important to discuss how the teams
collaborated and which strategies worked best. Encourage
team members to share their thoughts on what they
learned from this activity.
#7. Mock Trade Game
In this exercise, employees should participate in a trade to
understand the effects of supply and demand on pricing.
Time: 30-45 minutes
Materials: Fake “money” (Monopoly money), and Items to
trade like pencils, paper clips,etc.
Participants: 4-6 people
Instructions

Divide the participants into groups of two, and
provide each group with some fake money. Ask them to
decide on an item that they will trade and set a price for it.

Have the groups take turns trading items at their
agreed-upon prices, allowing them to make profits or losses
based on their decisions.

After trading has finished, have them compare profits
and losses.
Debrief
During the debrief, it’s important to discuss how each group
was able to maximize their profits or minimize their losses.
It is also beneficial to ask the participants what strategies
they found most effective in order to gain insights into
future trading decisions.
#8. Strategic Terms
The objective of this activity is to help participants
understand and apply common terms in strategic planning.
Time: 15 minutes
Materials: Index cards with terms related to strategic
planning, timer
Participants: At least 4 members per group
Instructions

Divide the participants into groups. Then, split each
group into two sub-groups.

Give each sub-group a set of index cards with terms
related to strategic planning such as “Goals”, “Risks”, and
“Rewards”.

Each sub-group will then take turns drawing one card
at a time and explaining how it relates to strategic
planning. For example, when a sub-group draws the “Risks”
card, they must explain how taking risks can help an
organization succeed but also carries a certain amount of
uncertainty.

At the end of the game, the sub-group with the most
creative explanations for each term is declared the winner!
Debrief
During the debrief, participants should reflect on how their
groups worked together to come up with creative
explanations for each card and gain new insights into
strategic planning. Additionally, discuss successes and ways
to apply what was learned in real-world scenarios.
#9. SWOT Analysis
The objective of this activity is to help employees identify
internal strengths and weaknesses, as well as external
opportunities and threats.
Time: 45-60 minutes
Materials: Whiteboard or paper, markers
Participants: 6-10 people
Instructions

Ask the group to identify an area in which they need
to implement change or improvement.

Have each group member list out their own strengths
and weaknesses related to the topic. Also, they should
identify any external opportunities or threats that could
impact their success.

Ask the group to brainstorm potential strategies based
on their strengths and weaknesses, as well as any external
opportunities or threats.

Then, they can discuss the risks and benefits associated
with each strategy, and make an informed decision.
Debrief
During the debrief, it’s important to ensure that everyone
understands how their individual insights contributed to the
strategic planning process. You should also encourage group
members to share any additional ideas or questions they
may have.
#10. The Strategy Grid
This activity is to help teams focus on actionable items while
creating an effective plan for achieving results.
Time: 30 minutes-1 hour
Materials: Paper and Markers
Participants: 4-8 people
Instructions

The facilitator should draw the grid on paper or
whiteboard, with columns and rows representing the goals,
objectives, strategies, tactics, and timelines needed to
achieve success.

Team members should then brainstorm and come up
with different ideas for each section of the grid.

Encourage discussions and ask questions to ensure
everyone understands the objective of the activity.

After all the sections are filled out on the grid, the
teammates should discuss the best strategies and tactics to
achieve each goal.

Once finished, debrief as a team, highlighting successes
and areas for improvement from the activity.
Debrief
As a facilitator, remind the team that communication and
collaboration are key to achieving success. Also, encourage
the team members to be open and honest in their feedback
on what worked well during the activity as it will help
them in future planning sessions.