Reflections on Achieving Your Goals: How to Develop and Sell a Strategy

Strategic planning is the holy grail of leadership. Or is it?

Let’s talk about mental models for strategic planning (e.g. 3 year plans, business strategies) and also how to best communicate the outcomes – the famous ‘evangelizing’.

Strategic planning is all about setting the right priorities to have the biggest impact on desired outcomes. Strategic planning is setting the goal post, tactical execution is actually getting there (it took me about 10 years of my professional career to truly get that – I can be a slow learner).

Strategic planning is – or should be – true working backwards. The question should not be “what can I do next” but “where do I need to be 3 years from now”. With that, it always starts with getting clarity on the end state, the goals and the big problems to solve.

Where do you need to be in 3 years?

What are the goals (even better: what is THE goal)?

Identify the goals that you need to achieve. How can you measure whether you make progress against those goals?

Understand why they matter and how they might be correlated (positively or negatively) to each other.

What have you learned? What are your fundamental insights?

Goals are great metrics for progress, but there might also be big fundamental or structural issues that need to be solved, but are not immediately apparent from looking at the goals.

It’s good practice to reflect on what you have learned since the last strategic planning. Did new key problems or constraints present themselves that can have material impact on your ability to achieve the goals? Did new opportunities present themselves that weren’t obvious the last time?

Think backwards, not forward!

Don’t constrain yourself by what you know and have (e.g. current capabilities, existing funding, roadmaps and team structures).

Define where you need to be. Figure out how to get there in the next step.

“If all you have is a hammer, everything looks like a nail.” – Forget that you have a hammer for a moment, think about what you need to do and only then about what tool you might have to acquire.

What are your big levers?

Now that you know your goals, problems and opportunities – how can you have the most impact on those? What are your biggest levers?


Make a list of all the things (the means to an end) that will help you to move towards the end state you want to achieve in 3 years.

Again, don’t limit yourself by current structure or what tech pieces you have. Think about what you need to move the goal, solve the problem or seize the opportunity.

Force yourself (!) to not just think about thinks you ‘could do’ but focus on what actually, truly, directly moves the priorities you defined previously.


Obviously, you cannot do everything you came up with in your brainstorming. You need to decide what to do first, what to focus on. No peanut-buttering.

What are the few things that will have outsized impact on your ability to achieve the desired end state?

Identify the biggest levers. Look at the outcome/impact, but also the cost/feasibility (i.e. what’s the Return of Investment, the ROI, of an idea). Make a sorted list of your biggest levers, their impact and their cost. Once you have that list you and your leadership can draw the line wherever you think the right ROI tradeoff is for investments.

Solidify your case

Get data. Make sure your initial assumptions are correct and the ROI story holds water.

Understand more details and make sure the idea is still feasible.

Start making a worry list or risk tracker (i.e. what could go wrong?) and burn it down. This process will not end until your final project will be shipped. Having a risk tracker or worry list is generally a good practice to avoid surprises.

Sell your story!

By now, you have put a LOT of thinking into your proposal. Be mindful that no one else has any comparable context or level of detail. You will need to catch up readers quickly and completely.

The best way to do that is to re-create your thought process for them in your story telling. Here’s a story flow that works.

Start with the goals

What do you want to achieve? What are your measurable priorities?

Why do they matter? Why these and not others?

Proper framing

What is the environment you are operating in? What have you learned (e.g. problems, opportunities)?

What assumptions about the future are you making that further inform your plans and thinking? What constraints do you need to work with?

What multipliers can you leverage?


Why did you pick the things you picked? What did you identify as the biggest levers and why (ROI)?

What did you push below the line and why (that’s a great appendix to have, especially when leaders are looking for additional projects to fund)? What are the most painful tradeoffs and what would it take to bring them back in?

This part is the ‘money piece’, you either get decision makers on board because they can follow your reasoning or you lose them because they cannot re-create what prioritization and tradeoffs you made.

Get tactical

Start giving a preview of how you will deploy your levers.

This is where reality kicks in.

From your current state, what are the next steps? What are rough timelines on how you would go about solving your problems as well as building and deploying your solutions?

What are the big questions you need to answers? Is there anything you need from leadership (play this card carefully and deliberately)?

Go do it!

You have a plan. You have approval. Go Execute!


Did you like this article? Want to read more?

I will keep posting articles here and I have them lined up way into summer 2020. However if you want to get it all in one comprehensive, structured, and grammar-checked (!) view, check out our new book:


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