An Introduction to Thinking Time

By Keith J. Cunningham

All my problems started out as a good idea. How about you?

I have an attic full of virtually unused exercise equipment. I purchased these

tread mills and elliptical training machines in the mistaken belief that if I just
owned the right gear, I could get in shape.

I sometimes get stuck and can’t find the answer to my problems. I can spend
hours fretting about and describing the problem (in glorious detail), yet remain
frustrated by a lack of clear solutions that will get me from “here” to “there”.

If you are like me and most people I know, you have also suffered from bad
assumptions, unchecked 2cd order consequences, failure to define the problem
that is, and a belief that finding the right answer is more important than finding
the right question.

Business and investing are intellectual sports and do not respond well to
emotional and glandular decision making processes. My experience is that the
key to getting rich and creating the sustainable success we desire is avoiding
stupid, emotional irrational decisions.

Don’t believe me? I’ll ask you the same question I’ve asked tens of thousands of
people in my presentations and business seminars around the world: How much
money would you have right now if you could unwind any three financial
decisions you have ever made (all good ideas at the time)?

This dollar amount is your “Dumb Tax”. I have a dumb tax and mine is in the tens
of millions. Years ago, after suffering a humiliatingly large dumb tax, I swore I
would never do that again. I set about creating a tool that minimizes my

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 seemingly unlimited ability to sabotage my results and hit unforced errors. This
same tool simultaneously maximizes my progress and results. Thinking Time.
Sadly, what most people call thinking is nothing more than rearranging
preexisting prejudices.

Twenty five years ago, when I first I sat down to “think”, I sat at my desk, pen and
paper in hand, and immediately took a nap. The afternoon naps continued until I
could design a “Thinking Time Process” that would enable me to differentiate the
story from the facts, check my assumptions and prejudices, think through the
“what ifs”, define the actual problem or obstacle that was blocking my progress
and create a question that would provide me access to alternative answers.
Today, I have over 650 questions I have created to support me in my bi-weekly
Thinking Time rituals.

At the heart of my Thinking Time Questions are five core themes:

1. Checking Assumptions: All those good ideas that turned out bad have one
thing in common…. Unexamined assumptions (which usually takes the form of
a really great story). Thinking Time gives me an opportunity to test the validity
of the assumptions I am making (or the story I am telling).

Here are a couple of my favorites to illustrate the significance of faulty

assumptions:
 Most people assumed that computers would do away with paper (yet
we use more paper today than ever before).

 Kodak assumed digital photography would never catch on (they

invented it).

 The Swiss invented the battery powered watch, assumed it was a bad
idea and failed to protect the idea with a patent.

One of my favorite questions is: What Don’t I See? What none of us see are
the assumptions we make about a problem or a situation. The reality is that
virtually all my Dumb Tax could have been avoided if I had just questioned a

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 couple of assumptions prior to pulling the trigger. Looking back with the
benefit of 20/20 hindsight, it is obvious that many of my original assumptions
were highly unrealistic, overly optimistic or just plain lazy…. And they were all
unquestioned.

2. 2cd Order Consequences: Nothing wrong with eating that Krispy Kreme or
investing in your brother-in-law’s “athletic sock that doubles as a pot-holder”
garage start-up business if you have thought through the possible 2cd order
consequences. I use a simple three part rule to help me think through 2cd
order consequences:

A. What is the upside? (We are usually experts at this one.)

B. What is the downside (what could go wrong)? (We rarely can do

this one by ourselves because we are irrationally emotional when the
decision making occurs.)

C. Can I live with the downside? (Only the pros bother to think about
this one, which is why their track record of dumb tax is so much
smaller than the rest of us mortals.)

3. The Core Problem: Problems and obstacles are typically identified as the gap
between where we are and the outcome we desire. Separating the “symptom
we see” from the “problem that is” is no easy task.

The symptom is what is visible, but it is rarely the real problem nor is it the
root cause of the problem. Sadly, we tend to gravitate towards fixing what is
visible (the symptom) and therefore make no progress on solving the real
problem or overcoming the obstacle that is blocking our progress to the
desired outcome. We build machines for the problem that isn’t.

Addressing the symptom makes us feel better in the moment because we

think: “At least I’m doing something”. But confusing activity with productivity
is a major saboteur of success. Being busy on the wrong thing is analogous to

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 running the wrong direction enthusiastically and is a complete waste of time
and effort.

Sustainable forward progress (a.k.a. “Kicking the Can”) is only possible by

identifying exactly where I am, exactly where the can is and exactly where the
goal line is in relation to me and the can.

When we get a headache (the symptom), the typical response is to alleviate

the pain by taking an aspirin instead of figuring out the “root cause” activity
causing the headache and stopping the ‘hammer to the head’ activity which is
causing the headache to begin with. This process of problem identification
often requires peer input, brutal honesty and is frankly the most difficult part
of the Thinking Time process.

If you feel it is necessary, you can take the time to try to figure out what is
causing you to hit yourself in the head with a hammer. If this takes longer
than about 15 minutes, you need to move on. After all the psychoanalysis,
you will need to make a decision to stop the hammering regardless of why
you are doing it. All the understanding in the world does not change the fact
that if something needs to change, then the decision to change it is KEY to the
change.

4. The Unasked Question: A problem is simply an unanswered question. If

there is no possible solution, it is not a problem but rather a predicament.
(A Predicament is a state of environment--e.g. the price of oil, being 64
years old or a tornado… Nothing you can do about it.)

When we get stuck and don’t know what to do, we think the reason is
because we can’t find the right answer. My experience is that finding the
"right" answer is rarely what keeps us stuck. What keeps us stuck is bad or
inferior questions. Changing the question is what gives you choices and
opens your mind to possibilities never previously considered.

The mistake we make is that most of our questions are tactical and revolve

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 around what we should do next to address the symptom (which pill to take).
As a result, we gravitate towards building a machine first instead of
identifying the core underlying problem and then building the machine to
solve that specific problem. Weigh too much? The question we erroneously
ask is whether we should buy a jump rope, a diet book or a treadmill? Not
enough sales? The question we erroneously ask is what marketing initiative
should we start, or how many new sales people should we hire or which
search engine optimization expert should we retain to increase sales? These
are bad questions. They are all tactical questions which require tactical
answers.

A better set of questions would be: Why am I five pounds overweight

(really)? What could I do to gain five more pounds? Why aren't my sales
2X bigger than they are today (really)? What could happen to cause a
potential customer to not buy from me? What risk or friction is the target
market perceiving that is causing them to ignore me? What must happen
to cause a customer to buy from me? What must happen to keep a
customer coming back?

Here it is on a bumper sticker: Having the right answer is the definition

of being smart. Having the right question is genius. Why? Because the
answers keep on changing. The only constant in business is change. The
answers I have now were answers created in a different environment
at a different time when I didn’t know as much as I do today. For me to
remain relevant in today’s environment, I need to re-ask the question
and search for new possibilities.

Hint: A great question starts with: “How might I….?” The power of this
question three-fold:

A. It reframes the problem as a question. Restating the problem

will not give you insight on the answer (“I am poor” does not
shed any light on getting rich… and neither does “Why am I
poor?” Asking a “How might I…?” question makes the problem

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 solvable.

B. It forces you to think in terms of possibilities and options.

Thinking Time is about generating ideas. I will sort through and
rank the ideas and find the best options/choices after my
Thinking Time is finished. The best way to have a great idea is
to generate a lot of ideas and then to pick the best one.

C. It forces me to think in terms of what I must break versus what

needs to be fixed. A common mistake we make is to assume
that the problem is a situation that needs repaired, duct-taped
or fixed. My experience is that often the machine that I have
built is not the machine I need. Putting wings on a bicycle does
not make it airworthy.

Great questions always have two common characteristics:

A. A great question simplifies the problem and makes it solvable.

B. A great question will expand the number of possibilities

available to solve the problem or improve the situation.

5. The Machine: Based on the Problem identified, the question now is: What is
the machine (solution) that must be built/modified to produce an output
which will move you towards the desired outcome? All machines require
three things:

A. A strategy and roadmap to overcome the obstacle that is preventing you

from getting from here to there. Strategies require prioritization.
Prioritization requires resource allocation. Failure to take into account the
resources required to build and operate the machine is a prescription for
failure.

B. People to design, build and run the machine. People do not operate in a
vacuum… they operate within a culture. They must possess the core
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 competence and technical chops to do the job. (I always know if the job is
bigger than the person if I hear more about the problems than I do the
opportunities.) “A Players” are mandatory throughout the organization.

C. Consistent and intense execution with dashboards, processes, best

practices, standards and metrics to measure the critical drivers, monitor
the progress, reward the success or coach the misses. Measurement
allows you to see what improvements (or corrections) are required to the
machine to enhance the outputs and thereby, accelerate the progress. The
machine can always be tweaked and refined, but these refinements are
dictated by the measurements. Measurement and correction are THE keys
to sustainability and a culture of accountability.

The machine is where the “Paprika Effect” is most likely to arise and is why
business success is so elusive and complex. Suppose you were baking an
apple pie. You had exactly the right recipe, the apples were the exact kind
Grandma used and were perfectly ripe, the dough was flawless, the sugar
precisely measured, the pie tin perfectly proportioned and appropriately
greased, the oven was working, pre-heated and the temperature setting
was accurate, the timer was true… but somehow a teaspoon of Paprika
was inadvertently added to the mix. Despite everything else being perfect,
this one small slip would cause the entire pie to be inedible. The same is
true for business. One small issue can derail the entire process. Finding the
Paprika Effect requires careful thinking and close observation.

Over the last 25 years or so, I have practiced “Thinking Time”, which is 30-60
minutes of uninterrupted concentration about a question I have developed. The
questions are designed to help me think about a problem or situation where I am
stuck or have somehow been hindered in making progress or where I am overly
optimistic or certain (usually a sign that I might be about to do something stupid).

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 My Thinking Time is highly ritualized. I have a Thinking Chair (the only time I sit in
it is when I am doing my Thinking Time)…. I have a Thinking Pen and Thinking
Paper Tablet (I only use them when I am in Thinking Time).

The rituals you will create will undoubtedly be different from mine, but the
following is how I do my Thinking Time:

1. I prepare a question (s) I want to focus on. The question(s) will almost
always center on one of the five core themes I addressed above. Often I
have created 3-5 questions that all center on a common thread or
concern. Sometimes, I change only one or two words in a question to see
if I can get a different insight into the issue I am thinking about. For
example, the original question might be: “Who is my target market?” I
might change this to: “Who was my target market?” I might change this to:
“Who is my competition’s target market?” I might change this to: “If I was
starting again today, what market would I target?”

2. I clear my calendar for at least 60 minutes, which will enable me to think

for at least 30 minutes and evaluate/sort the solutions and ideas I
identified for about 30 additional minutes. If the problem is thorny, I will
think for closer to 45 minutes.

3. For most of my questions, one thinking session is insufficient, but trying to

concentrate for more than about 45 minutes is the limit of my capacity to
concentrate. I will usually present myself with the same question over
multiple sessions (two or three is not uncommon) before I get an elegant
answer that is worthy execution. I often have a thinking session about the
execution (machine) after I have a solution or options/choices. (Hint: An
“option” is an idea. A “choice” is executable.)

4. I close my door, turn off the phones and eliminate all noise and visual
distractions. I typically think with my left hand (I am right handed) on my
forehead which limits my ability to start looking around my office and
breaking my concentration.

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 5. I set a timer on my computer that will alert me when my Thinking Time
has expired (which keeps me from fidgeting and looking at my watch).

6. I sit in my chair (which does not face my computer)… question, pen and
Big Chief Tablet in hand (I always think on paper and never the computer…
too many distractions and temptations).

7. I sip my water, scratch what itches, clear my throat and get my body
perfectly still. I have found over the years that my body will derail my
thinking and break my concentration. To optimize the thinking process, I
must lose touch with my body so that my train of concentration is totally
uninterrupted. During my Thinking Time, I am totally motionless except for
my right hand, which is recording my thoughts.

8. On my Thinking Tablet, there is always an empty dot (“.”). It will look like
this:
Question: How would I run my business if 100% of my future
customers were by referral only?
 ABC
 XYZ

The instant I write down an answer, I always create a new dot (“.”). My
mind sees an empty (“.”) and assumes there must be at least one more
idea.

9. The thinking and writing starts. This is a creative process and is not
intended to be filtered or judged. If I hit a blank or gap in which nothing is
flowing, I will silently re-ask myself the question I am asking that day. I will
usually start by silently asking myself, “What else could it be?” or “What
could I do that would make this problem worse?” or “How would my
competition solve this problem?” or “If I got fired and a new CEO took
over, what decision would they make?” “What would Warren Buffett do?”

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 10. I am looking for ideas and possibilities, not perfection and absolutes. I
attempt to avoid judging my ideas (which I have found is almost
impossible for me), but nevertheless, it is my goal. The more judgment I
have about an idea during the actual Thinking Time process, the less
creative and more prejudiced I tend to be. I let one idea spark another
tangential idea and follow that train of thought as far as it wants to take
me.

11. When my Thinking Time is successful, I am always startled when my alarm

goes off. I can’t believe how quickly the time has passed. I will always take
at least 15 minutes to read what I have written and cull out the good ideas
(usually no more than three). These ideas can then become the basis for a
future Thinking Time question or might need to marinate for a few days
until they ripen. Remarkably, the better ideas fall into a pattern known as
the “third-third”. The last 1/3 of my ideas on a given day tend to be the
most robust. The first third are typically the obvious ideas. The second
third are variations on the first third. The third-third is frequently where
the juice is.

12. Culling my ideas while they are fresh is crucial. I have a separate file in
which I keep my good thoughts, insights and distinctions. If any of these
ideas are worthy of future consideration or possible action, then “calendar
time” must be scheduled. Without calendar time, it stays on my “To Do”
list and never gets implemented or addressed. (A pretty handy tool I use
for “To Do” lists is to find the items that keep getting transferred from list
to list throughout the year and do a Thinking Time on this specific “To Do”
to figure out what needs to happen to get traction.)

13. It is rare for me to have fewer than two or more than three Thinking Time
Sessions in a week.

Fundamentally, Thinking Time is about five core themes:

1. Check your assumptions

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 2. Think through the “what if” and 2cd order consequences.

3. Identify the real problem or obstacle blocking your progress.

4. Create a better question which will give you insight and perspective.

5. Design and operate the machine required to deliver the results.

Smaller dumb taxes, better possibilities and accelerated progress are the result of
better questions, thirty minutes sitting quietly in a chair, a pen and paper… Not a
shabby return for such a low cost investment.

KJC
The following are Sample Questions from my Thinking Time Question File:

1. How did this get to be a problem to begin with?

2. What could I do to improve my situation or make the situation better?

3. If I could ____________ really, really well, I could solve this problem?

4. What have been the impediments or constraints that have hindered me?
(Skills, Desire, Resources, Time, Discipline, Environment, Commitment)

5. Do we have any special or leveragable relationships or alliances in our

customer list or network of contacts and associates which could influence
groups of potential buyers?

6. Competitively, why do customers buy from us? Why isn’t this strength
sufficient to cause more potential buyers to stop doing business with our
competition and to start doing business with us?

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 7. What are the specific concerns, fears or friction points that must be
addressed or mitigated to cause a potential customer to start doing
business with us? What is the frictionless, compelling reason for them to
switch to us?

8. What is the one thing that would be the difference that makes the
difference for each segment of the market and would cause this segment
to buy from us? What is the difference that makes the difference to the
unsold buyer? How does the unsold buyer define “Success”?

9. What are the additional resources (money, manpower, skill-sets,

marketing, expertise) we will need to acquire to successfully get traction
with this market segment? Does our organization chart have some
holes/upgrades that need to be filled in light of this new strategic growth
initiative?

10. What are the core activities which must be prioritized to insure the
success of this growth initiative? What are the non-core activities which
need to be eliminated or deprioritized?

11. How (specifically) does the unsold buyer define “Success”?

12. What do I already know that I should be doing but I am not executing on a
consistent basis? Where is my shovel and why am I not using it?

13. What am I executing on that used to work but is not the right strategy in
this environment? What do I need to stop doing and what do I need to
start doing?

14. What are 5 things that I can do immediately to improve my situation.

What can I consistently do to improve my situation? What am I doing, but
not consistently, which would improve my situation?

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 15. What must be monitored, measured and changed to ensure the relevance
and continuity of my business, product, success proposition, culture and
brand? When I look back several years, what has changed (either
internally or externally in the environment) that is impacting my results?
What changes do I need to make to my business to ensure my continued
relevance to my customers?

16. What are 5 things my competition is doing that are causing customers to
choose them and not me? What are three things my competition does
better than I do? What are 5 differentiators that are the difference that
makes the difference in my business? How are these five things different
from the competition and how much does the consumer really care?

17. Where am I not paying close enough attention and therefore settling for
average instead of demanding excellence?

18. What assumptions am I making that gives me what I see? What if what I
am thinking is wrong... then what might be true? What if what I thought
was true was actually dead wrong and the opposite was true? What part
of what I believe is true is actually a story or an opinion? What are the
consequences if what I am assuming to be true is in fact wrong?

19. How do my customers, clients and target market define success...

specifically? Where is the mismatch between what I currently offer and
what they really want? What must I change to give the customer certainty
that if they buy it, they will get the solution they are seeking?

20. What obstacles or problems are we trying to solve? What are the guiding
principles or boundaries to our possible solutions? What are the few big
things we need to align and get right in order to be successful with this
strategy? What do we need to stop doing?

21. Where am I spending money that doesn't produce a return? Where can I
stop spending money that isn’t producing a return? When I carefully

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 analyze my business’ expenses, are there some costs that can be whacked
or reduced because they are feeding my ego and not my net worth?

22. If I could devote 100% of my time to just one customer, who (specifically)
would it be? What do they "look" like? What are the 5 biggest
problems/pains/issues they have? Where are they frustrated? What can I
do for them that no one else is doing? How do they define success? Why
should they choose me? How do they define success? What internal
processes must we excel at to deliver this definition of success?

23. What is impossible to do today, but if it could be done, would

fundamentally change my business?

24. What should be getting done that is not getting done because I am doing
the minor and not the major things? What should I be doing which would
add more value? What am I currently doing that could be done by
someone else? Who can I add to my team or what can I outsource that
would free up my time to start doing the most important things? What can
I (and only I) do? If I only had someone on my team who could _______, I
double the size of my business.

25. Who is my target market? How do they define success? What do they
think is important? If I deliver it to them, will they buy? How is this
different from my competitors? What internal processes must I excel at to
deliver on this Success Proposition? Is my compensation structure and
culture aligned with executing and rewarding these internal processes so
that I can deliver those outcomes?

26. Where are we compromising by looking for door marked “WOW!” What
shortcuts are we attempting to take that are not really shortcuts but
rather mirages of greed, laziness or impatience? What skills do I need to
master to attain the success I want?

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 27. What are the 2cd and 3rd order consequences of some of my current
initiatives? What are the risks of what I am currently doing? If things don’t
turn out as planned or take longer than I estimated, what is my Plan B and
can I live with the consequences? Am I currently executing on any projects
in which I am counting on luck and good timing instead of sustainable skills
and tools?

28. What skills do I need to learn to help me run my business? Where am I

confusing activity and sweat with productivity? What am I currently doing
that should be outsourced or leveraged to someone else (even part time)
which would then free me up to do more of the critical value add
activities? What critical projects are languishing because I simply don’t
have the time to allocate to them and get them off the ground? How can I
reallocate my calendar and reprioritize my time to find an additional 60
minutes per day to work on high value projects?

29. Where have I allowed “our process” and way of doing things to become
calcified? Where do we need to change our processes to be more
customer oriented? Where could I give my employees some autonomy
and discretion so they would engage in their work at a deeper level?
Where am I letting the need to do it my way get in the way of meeting my
employee’s needs and my customer’s expectations?

30. Where has my business changed since I first started? What processes or
systems do we have that no longer support our flexibility? Where is my
business lacking in flexibility? Is it with my employees? Or my customers?
What exceptions should I be making to show my customers and
employees the love?

31. Where can I create leverage? Where are the growth opportunities that I
have been postponing because they require extra effort or are outside my
comfort zone? What are some of my problems that require a new
solution? If I had a Board of Directors, where do I need to pick up my game
to deserve the “raise” I am seeking?

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 32. What should I be working on to make the progress I want? How do I do
that?

33. What should I do more of? What must I do less of? What am I promising
to start doing? What am I committed to stop doing?

Keith J. Cunningham is regarded as one of the world’s foremost business teachers. He

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and then manage it for success. Keith will teach you the critical skills needed to
effectively assess business and investment opportunities.

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