Should I, Shouldn’t I

“Truly successful decision making relies on a balance between deliberate and instinctive thinking.”

~ Malcolm Gladwell

Should I, Shouldn’t I

By Simon Tyler

When faced with a complex decision we all have a conscious or unconscious habitual pathway to get to the choice. Every now and then a special decision shows up that no matter how much more data or opinion is garnered, the choice still remains uncertain and in the balance.

Whether you are a strident, pull-no-punches decider or a cautious wait-for-consensus diplomat I’m sure you will still have met occasions when you get stuck. This stuck place can become irritating (you with yourself!), you may even start an escalating haranguing (of yourself) as you struggle to see clearly what to do.

Over my years as a coach, in my learning, my observations and my work with clients I have offered a number of decision-assistance techniques, beyond the obvious research and peripheral inquiries. Here’s a few for you to begin with:

Live-With-It – in effect move in with the option for one day. For example I often encourage clients who are contemplating a career move to print a business card with their new title/company and carry it and look at it often during the day. Engage (where it is confidentially appropriate) in conversations about the new role, look at publications/magazines/websites related to the new option. Take as many sensory options as you can during the day (e.g. visual = the card, auditory = the conversations, kinaesthetic = different new role clothes).

Coin-Toss – if it’s a ‘this or that’ decision and you have spent a sufficient amount of time cogitating and the answer remains unclear, toss a coin and go with the outcome (if you catch yourself going for best out of three or five, then you might not yet be ready!).

Put-It-Down – you might simply not be ready, in forcing yourself to make a decision you might be forcing the pace when it is simply not the right time. Put the decision down for a defined time period (e.g. one week) and exercise mindfulness strength by letting go of thoughts about it as it comes up in the intervening period.

Ten-Mates – first distill your choice into as brief a paragraph as possible, then make a list of 10 mates (e.g. 3 work colleagues, 3 family members, 3 social friends and 1 odd ball such as your doctor or dentist or parish priest). Now contact all 10 (by whichever communication channel works best) and position your decision paragraph, and that you are inviting them to intuitively react to your choice, and of course alleviate any pressure they may feel under by absolving them from any implications of a wrong choice!

Advantage-Disadvantage – this two column list is one of the most popular do-it-yourself decision techniques. I like it as it can shift your frame of reference and can be a channel for further creative thought. You’ll know what basic questions to use with this technique, keep the list going for a few days (as once started your quiet creative subconscious will continue to work on it).

And then my favorite, the ‘Should I, Shouldn’t I’ filter questions. This is a shortcut questioning route into your intuition. The answer to each may be at first obvious and distinct but I encourage you to ponder each for a few minutes, and perhaps write a paragraph for each to help explore your answer:

– Easiest
– Simplest
– Most frightening
– Most exciting
– Bravest
– Boldest
– Heaviest
– Most colorful
– Tastiest
– Loudest

Some of the questions may seem odd, but go ahead and write your response, it will quite probably trigger your deeper and, up till now, quieter thoughts about the entire decision.

Good luck and keep it simple.

Coaching Call to Action

What’s your favorite decision making technique? In what ways does it work for you and in what ways does it not work so well? Please take a moment to share in the comments section below.


Simon Tyler is one of the world’s leading business coaches. His work simplifies the lives of business leaders and owners. He is an incisive consultant, inspirational writer, provocative public speaker and master facilitator. To learn more about Simon, visit

Photo credit