If you are anything like myself, whenever you face a challenge or simply want to find answers for complex questions, you look for advice. Whether it comes in the format of reading, listening, conversing or watching, you find people you admire, who supposedly know better than you, and you seek for their opinion.

I recently finished reading the book “A tribe of mentors” by Tim Ferris, where he asks the same 8 questions, to over 100 high-performing, successful individuals. I devoured the book and my green pocket-size Moleskine was filled with thoughts and ideas. However, in reading this book, I realised how much conflicting advice you can find about one single topic.

Some of my favourite questions in the book were “How has a failure, or apparent failure, set you up for later success?”, “In the last five years, what new belief, behaviour, or habit has most improved your life?”, and “What advice would you give to a smart, driven college student about to enter the real world?”. The answers were insightful and extremely practical. Each interviewee provided a very rational and well-thought explanation of why they were offering their specific advice. However, there was a lot of contrary advice.

While some people seemed to think about failure as the greatest source of learnings, others talked about over-romanticising failure as an excuse for poor preparation. Some talked about meditation, others spoke about getting out of their heads by spending time with family and so on and so forth…

Reading each of those advices I wrote down in capital letters across two pages of my notebook:

What action to take is relative to your unique situation.

That led me to 3 questions:

1- why do good/proven strategies fail?

2- how do I develop a winning strategy?

3- when should I dismiss advice, or proven strategies, and power through with my own ideas?

Below are my best-attempts to answers to these questions:

Why do good/proven strategies fail?

I often see smart, ambitious people directly applying techniques to solve problems from one situation to another, and watch them fail, or get suboptimal results. I for once, have done that multiple times.

In my academic endeavours, I was given the advice that in order to succeed I should pick research topics that were easily “researchable”, otherwise, I would find myself getting lower marks than my peers due to lack of existing literature to “back me up”. Following this advice, not only didn’t get me the marks I was hoping for but also resulted in a very frustrated MSc student producing mediocre papers. The worst part was how miserable I felt researching topics I had little interest in.

In work, I was told multiple times to climb a career ladder instead of dipping my toes into multiple industries moving laterally, only for it to prove to be a successful strategy for my chosen field.

In analysing my personal situation I have arrived at the following conclusion: the key to applying existing knowledge and proven techniques to your challenges is to use critical thinking. Getting advice is good, but you need to go a layer deep into the theory that explains why that approach worked. To solve your hubris, you must seek to know the strategy, your situation and yourself inside out, before committing to a plan.

Adopt a strategy that is coherent with your situation and your goal. And remember the world is changing at a fast-pace, strategies that were useful 10 years ago, might not be relevant anymore.

A cookie-cutter approach won’t deliver optimal results if you are trying to solve new problems. Equally, to reinvent the wheel to solve a problem that is already solved optimally is a waste of resources.

How do I develop a winning strategy?

If critical thinking and knowledge are the keys to unlocking a great strategy, awareness is where you must start. In order to critically assess any situation, firstly, you need to gather the most information you can, for a reasonable cost (time or resources).

For example, when I started to practice Yoga 7 years ago, my main goal was to become stronger and more flexible, both mentally and physically. I attended class 4 days a week and pushed myself to do the hardest poses. I observed those around me, I listened to the teacher’s instructions, watched countless youtube videos on tips to master each pose. What I failed to recognise was that nobody knew my body. Not even I knew my body!

In applying all those techniques relentlessly without first checking with my body, I got injured. I was out of the game for 3 months recovering from a back injury, the strength I hoped to gain was even further than before. It was only after that fall that I learned that – or more precisely, was forced – to recognise and accept exactly where my body was at was the key to figuring out which techniques and levers to pull and when to use them.

Once you develop a great sense of awareness of your situation, you can scenario-play with existing and proven strategies, and apply the ones that make most sense for your situation.

When should I (politely) dismiss advice, or proven strategies, and power through with my own ideas?

I am a big fan of crossing disciplinary boundaries when it comes to strategies and theories. Learning something from one field and applying to another can lead to innovation. I am an even bigger fan of people that develop their own strategies from the ground when they have realised that the techniques used by those before them, are doomed to fail.

It’s important to perform a thorough analysis of the situation in relation to the strategy. If you can come up with good reasons why the advice would not help you succeed, don’t settle for it just because someone said that is what you should do (even if they are super successful).

If the advice is given to you by your boss or someone more experience, chances are they have good reasons to believe you will be successful using their tactic. So don’t dismiss it too quickly either. Discuss your thought process, gather their feedback. You might realise that what you see is not the full picture or due to lack of experience that you might be missing an important piece of the puzzle.

Once you have this discussion, saying no to the strategy will be much easier, because at the end of the debate, the most rational point of view should emerge naturally, and the best strategy should win.

If the strategy is something you have learned from the best in your field, and perhaps it is considered the “best practice” amongst your peers, go through the same process with someone you trust and that is likely to know areas that are your blind spot (for example your team). The exercise of questioning the status quo is good for everyone involved! This will too help you back-up a decision to a customer, an investor, a manager or a loved one.

However, beware of compromise! Often groups can arrive at a “mixed” strategy, doing a little bit of the old a little bit of the new. Mixed strategies are typically doomed to fail as they lack coherence in their approach.

In my career, I have seen this happen multiple times. For example, I have been at companies that fail to deliver software when PMP project managers and Agile Product Owners conflicted, and a mixed approach for delivery was “created” to appease both sides. The issue is that both philosophies conflict at a fundamental level, creating confusion amongst the involved parties, messing workflows, making measuring leading indicators of success a nightmare, ultimately resulting in avoidable failure.

Ultimately, we live in a fast-paced world. We have more data than ever to understand scenarios. Change is a constant as technology evolves at a faster rate than ever and solutions get smarter and more sophisticated. Therefore, finding a balance between applying existing strategies to known problems and developing novel strategies for new problems is a skill that we all need to acquire. Otherwise, we will inevitably, fail!

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