Mastering the Art of Planning as a Founder

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“Planning is bringing the future into the present so that you can do something about it now.”

― Alan Lakein, author

When I do work with founders I often hear something in the lines of:
“But Stoyan I don’t have time to plan my time. I’m busy.. you know?” 

What is planning? Why do we need to take this area more seriously? 

Let’s take a look at the facts. According to different statistics – 90 – 95% of all startup companies close doors within the first few years of existence. Being an entrepreneur is not an easy ride. It’s actually pretty tough. A small number of people decide to take the ride and jump into this risky journey. And a small percentage of them succeed to actually build something of meaning. 

We like to glorify entrepreneurship, like it’s always fun. You dress fancy, you meet important people, you are your own boss. You connect the dots and make things happen. But this is just one side of the coin. 

In many ways being an entrepreneur and starting a new company is a lot more like – getting into the jungle. The jungle is abundant and filled with opportunities. But it is also very dangerous.
And your main task, especially when you are small and just starting up, is to survive and adapt. To secure shelter and food, long enough so one day you get the chance to thrive and rule. But you gotta love the process. Cause it might take you 5-7-10 years. 

And while developing a bias toward execution and getting things done is a must, it’s equally, if not more important to master the art of effective planning!

The ability to prioritise the results that matter most, and SAY NO to everything else.

Think about that jungle metaphor again. I’m sure you have seen one of these movies, where the characters got lost in the jungle and they climbed a tree nearby to figure out where are they, what’s the road ahead, and how should they proceed forward. 

That is planning. Planning is about strategy. It’s about seeing things from above, and maximizing your resources to achieve the results you are after. 

And if you are serious about your startup, you have to do it every single day!

Here are a few simple mindsets you can acquire to boost your productivity: 

1. Make planning a Habit 

The best way to improve your planning is to block time every day for doing it. Put it into your calendar, set an alarm and make it a habit! You need space to take the important decisions.

I usually block 30 minutes at the end of my working day. I first shortly measure my previous day:

  • Did my team and I manage to achieve our objectives?
  • What challenges did we encounter?
  • What can we do better?
  • And then I proceed with setting the priorities for the next day. 

As a startup founder it’s easy to get distracted. So it’s helpful, if you define your longer term objectives first. You can use tools like OKR-s or Goals Pyramid. Or simply set your Quarterly, Monthly, Weekly goals. (You can add to your Trello or KanbanFlow boards your longer term objectives). Once you are clear what your strategic objectives are, it’s easier to plan and prioritise where your day-to-day attention should go. 

2. Always Start with the Outcome in Mind

Before you start doing something, make sure you are clear what you are after. 

Do you ever have items on your to-do list like:

  • Do Sales
  • Blog 
  • Budget meeting etc? 

It’s a good starting point. But It’s not enough. It’s too general. And it’s a recipe for procrastination. What does “Do Sales” even mean? Step up your game! Get concrete and measurable. 

I recently had a chat with David Allen (author of Getting Things Done) at a speaker’s dinner in a conference in Austria. Here’s what he told me:

“Getting Things Done is about two things: What is the final outcome you are committed to achieve, and then what does ‘doing’ look like?”

It’s simple. You start with the end in mind, and build up an action plan backwards – your best-guess strategy to achieve that outcome. Yet so many founders get lost in doing activities, without a clearly defined purpose; working long hours, without weighing the different options and picking the ones with highest impact probability. If you get distracted, it’s ok – just ask yourself: “What’s the outcome I’m after?”.  

3. Practice Time-blocking

Very simple approach, but quite effective. You might have heard about the pomodoro technique or something alike. The idea is to block time in your calendar to produce a clearly defined outcome. And when the time comes, you switch off everything else and focus on that single objective. And once the time is off – you take a little break.

Ideally you will plan most of your day into time blocks. It’s kinda like – you are setting a meeting with yourself to work on that specific thing. And it’s super helpful. It’s so much easier to stay focused, once you have a measurable objective and a specific time constraint. You can start small and do 2 to 3 sessions 30 to 45 minutes a day. And just see how much you can achieve in such a short time.

These days I use time blocking a lot, while working on our upcoming book (cause there’s always something more fun than writing). But when I block 90 min (followed by 10 min breaks) and commit my productivity and focus increases. Give it a try! 

About the author:

Stoyan Yankov is a productivity & performance coach, professional speaker and a long-term mentor at Startup Wise Guys. Prior to that, Stoyan worked in film & video production, digital marketing and advertising. Today Stoyan is all about building people and building world-class teams! He is a co-founder & managing director at Samodiva Masterminds. Together with Cristobal Alonso (CEO, Startup Wise Guys) he has developed the #perform framework, a holistic methodology for team performance in startups. Currently both of them a co-writing a book based around the framework.

Btw, we have also had “5 Wise Minutes” with Stoyan, so you can deep dive into this one as well:

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