CEO Chronicles #10: The three prongs of your strategy

We now know that the three questions that can change your life forever are –

Who Am I?
Where Do I Want To Go?
How Do I Get There?

In “Mission Possible!”, we explored the first question – Who Am I? We understood the need for and the components of a purpose.

In “Your Highway to Happiness” and “Without a Vision, You Are Blind”, we answered the second question – Where Do I Want To Go? We discussed the amazing power and clarity that comes from having a vision.

Now, we move to the next stage of the journey, by plotting and charting…

Your Career Strategy

As you developed your mission statement, you discovered your Why.

As you drafted your personal vision, you defined your Where.

Your career strategy (or roadmap) answers the question, “How Do I Get There?” and helps you design your What, decide your When, and determine your How.

A career strategy has three parts:

  1. Tangible and quantifiable goals and milestones
  2. Realistic timelines
  3. The resources you need and the actions that you will take

Together, these form…

The Three Prongs Of Your Strategy

First, let’s start with What – these are your tangible goals and milestones. They may be –

  • Long-term targets (I will be promoted to Senior Manager by June 2023), or
  • Medium-term goals (I will be chosen as Star Employee at least once in the next 18 months), or
  • Short-term milestones (I will be ranked as High Potential during the Annual Performance Appraisal).

These goals and milestones need to align with your mission and vision. Each of them needs to contribute to your purpose, to your destination.

Your What crystallises your aspirations into measurable and realistic targets.

Second, your When: once you have designed your What, you have to decide the timelines by When you will achieve your milestones.

So, you, a Marketing Executive today, are going to be Senior Manager by 2022? Great! That will be an amazing achievement!

When will you take the first step from Executive to Manager? June 2021? Yes, that is a practical timeline and gives you enough time to achieve at least two good annual reviews.

By when will you expand your region to two countries? December 2020? Yes, that is a necessary step! Managers are expected to handle at least three countries.

By when will you exceed your targets in the current region you are handling? By June 2020? Fantastic. That will make your GM – Marketing sit up and take notice.

Will you be able to add 15 customers to your business platform by December 2019 so that you can ensure that you exceed your target? Fantastic!

Your When makes your What real. It tests your determination and commitment. It moves you from dreaming to doing.

Finally, your How – this lists the resources you need to achieve your goals (and milestones).

What brought you to where you are today is NOT going to take you to where you want to be. You will constantly need to enhance yourself, your skills, your capabilities. Broadly, we need three main categories of resources to support our career goals

  • Experience and track record
  • Knowledge
  • Networks

You aspire to be a Senior Marketing Manager?

Experience – you will need to show a track record in acquiring and retaining customers. Your company will want to see you grow revenue, year on year. Also, your boss would like to see you keep receivables in check. Finally, you may want to obtain customer testimonials about your commitment and service.

Knowledge – you will need to be seen as an expert on your product range. It is critical to know how to cross-sell and up-sell, and maximise customer value. Also, you must know your customers well and develop customer strategies, both for existing and prospective customers. Furthermore, a strong grasp of regulatory and contractual issues is necessary.

Networks – you will need to develop your presence in the domain. Customers must know you, like you and trust you. Also, your range of relationships must span the customer organisation. Within your company, you must be seen as a troubleshooter, a provider of solutions, a ‘go-to person’. Simultaneously, your competitors should know you and recognise your value and capability. Finally, you should be seen in industry and public forums.

Your How makes your What achievable. It helps you acquire the resources and tools you need. It propels you forward. And finally, it measures your progress.

To give you a live example of a roadmap, let’s look at…

My ongoing journey with CEO Chronicles

Purpose – To share my accumulated experience and knowledge with aspiring professionals so that they may lead satisfying and meaningful careers and lives.

Vision – I will positively impact at least 5,000 aspiring professionals by December 2020, by writing and publishing at least 35 instalments of CEO Chronicles.


  • Reach 2,500 readers by December 2019; then, 3,750 readers by June 2020 and finally, 5,000 readers by December 2020.
  • Publish CEO Chronicles on LinkedIn, Facebook,, and Evaluate and publish on more platforms over time.
  • Publish in at least 5 relevant Groups now; expand to at least 20 Groups by June 2020.
  • Intersperse articles with short posts; engage with readers and lead them to the articles.
  • Build a ‘resource base’ of 20-25 professionals who will advise me on topics that they see as important and high-impact.
  • Read widely, on-line and off-line, to understand the issues that concern and hinder professionals in the journeys.
  • Constantly seek feedback on the articles and make them more relevant and readable.

I hope this clarifies the concepts of What, When and How?

And thus, we come to…

The End of The Beginning

Let’s quickly review where we began – what do we need to go about constructing a successful and happy corporate career?

We need purpose (our Why). Then, we need direction (our Where). Finally, we need strategy (our What, When and How).

What these will do for you is what they do for all successful people – align your daily actions with your long-term aspirations, encourage you to live a life of purpose, and fill you with a sense of achievement, satisfaction and fulfilment.

I have devised a simple template (a ‘cheat sheet’!) that helps you converge your mission, vision and strategy on one slide. If you would like to have this, please get in touch and I will send the same to you.

Venkatraman Sheshashayee

Venkatraman Sheshashayee (Shesh) is Managing Director of Radical Advice, a business transformation advisory based in Singapore. He has over 34 years of experience in manufacturing, shipping and offshore oil & gas. Shesh’s previous roles include CEO of Miclyn Express Offshore, CEO & ED of Jaya Holdings Limited and Managing Director of Greatship Global. In his new avatar, Shesh helps SMEs, start-ups and aspiring professionals achieve their potential.
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