What does successful planning look like?
How do you plan your way to success?
I know they say that you have to fail fast to learn quickly, but how do you see the bigger picture and strategize without any planning? How do you know how long something will take? I tend to get burned out and waste a lot of time without planning and I've learned to take a step back and plan a lot more thoroughly to get peace of mind.
But what does successful planning LOOK like? Step by step, how do you know you've planned enough? No one wants to stay in planning forever, but I've ended up planning way too little and never really getting anywhere other than learning some new web tools and spending money of technology services.
So as a result of this thread (You guys are all awesome, thank you for sharing your planning ideas and insights!) I'm going to tackle my planning like this:
Making decisions:
To decide on my options and get the best from a brainstorming session, I start by writing up a list of criteria for deciding on an ideal course of action.
Then I get to work both brainstorming and refining my criteria. The more refined the criteria, the better the brainstorming ideas get.
Planning actions steps:
I first start out by writing up the goals I'm after, and a list of main things that need to be true in order reach that goal. This is different from 'things that need to get done', because these are results criteria.
With those main 5-6 main blocks of criteria, I can start to work backwards from there coming up with the most simple course of action until I can come up with specific actions steps. I do this until I can't think of anything else at all, in one sitting, and I come back to this roadmap as I think of things and at least once a week.
When I have processes or actions steps that are super long, I can create a new google doc and link to them from this main roadmap. That way the roadmap it's self is easily digestible.
Finally, when it's time to start taking action I whip out my Wunderlist and start to drop items in there straight out of my roadmap actions list.
Final thoughts:
One of the other benefits to planning I've found recently is that if the goal seems scary or too large, the planning process seems to make it feel more tangible, more real, more possible, and because it's in a roadmap, it feels more like the goal is an inevitability. Also, it gets the mind saturated with the goal, energized, creates momentum...etc
Boom. Time to get to work!
I'm an extremely thorough planner. I create a document for pretty much everything I do that's more than a trivial task. Looking back through the documents I've created, there isn't much of a pattern. They all tend to take a different form and have different sections depending on the task at hand. But here are some commonalities:
I almost always include an "overview" section that describes what the document is for. It's usually just 3-4 sentences written for someone else… or really for future me who won't remember what this document is for. Here's one I'm working on now:
Another commonality is that I tend to divide any creative task into two parts: ideation and evaluation. Basically, creation is a process of coming up with ideas, then using some sort of evaluative technique to separate the good ideas from the bad ideas. Often I will explicitly have a sections titled "brainstorming" and a section titled "rubric" in my documents. For example, our rubric for creating new content series for IH includes these bullet points:
I think having rubrics by which to judge your ideas is crucial. The more constraints the better. I've found that, counterintuitively, Having more constraints actually helps you come up with more ideas.
As for long-term planning, I've got a giant "roadmap" table in a Google Doc that acts as a calendar of sorts. It's divided into sections, some of which span a few weeks, some of which span a few months. Each section explains what I hope to accomplish during that time, and the rows under each section list big tasks, and typically link to a document describing that task (e.g. implement meetups feature, reorganize the forum, implement Q&A feature, do an SEO overhaul, etc.)
I should say that there usually comes a point during planning where I'm all "planned out" and so antsy to start building that I just start. But I try to revisit my plans often as I build, and revise them based on future learnings. And I re-evaluate my roadmap table every Monday.
Hopefully having my setup as an example is helpful in some way! Keep in mind that many people are less organized than I am, and yet get more done, so take all of this with a grain of salt.
There's a ton of gold nuggets in here that I am really grateful you shared. A handful are things I noticed I organically started doing as well like the idea and rubric sections. Having a solid criteria to judge ideas against really is super effective as getting more creative. From what you shared, the tip on how you link other documents which have implementation details from within your project roadmap is really awesome. Also, the tip about revisiting your roadmap every Monday, and the 'overview' section.
I know people who seems to hardly plan at all and yet they produce massive results. Then again, I don't really know just how much they plan vs how much they say they plan. I'd like to know if there's a commonality among entrepreneurs in this area. When it comes to strategizing and planning, what steps do they take when it's not something they're building as a scratch-my-own-itch-golden-right-time-right-place type of thing. Maybe some people just know which areas to plan out which are essential and which ones are ok to put off.
It's counterintuitive, but the best answer is to work backwards from a clearly defined and achievable goal.
It's similar to how much easier it is to solve a maze with a single exit if you start at the exit. If you start at the destination, you can avoid lots of dead ends (and wasted time/effort) along the way.
@amyhoy's book "just fucking ship" is full of techniques and tools for planning your work so you can actually finish it.
Here's a super visual mini lesson we included in our holiday bundle last year, literal flowcharts and how-tos for how we plan and teach planning to our biz students!
https://www.dropbox.com/s/x1rqj39tlqfxm66/2 Crash Course - Making Your Backwards Plan.pdf?dl=0
I never quite understood how to plan backwards like that - thanks! That's a big help in getting my head around it. I'll give it a try with my current roadmap.
I also tried the Getting Things Done project planning process but found myself super disorganized. My brain seems to like starting with an end goal and then road mapping my way there. So I think this backwards planning concept will be helpful.
Two of my favorite quotes on planning just to mix it up:
Dwight Eisenhower said "plans are useless but planning is essential" and Mike Tyson said "everybody's got a plan until they get punched in the face"
Very cool quotes, but they aren't useful. Like I said, I've wasted a lot of time and it seems the one thing I've learned is that SOME level of planning IS necessary... even if things don't go as planned. I spent some time away from working hard as I was frustrated and wondering "what am I missing?" and found inspiration in a rather dark place - I was watching Hunting Hitler and saw how if this dude actually managed to escape (if he did), the stuff they found suggests they had been planning their "exit" as much as 15 years in advance. Underground tunnels, safe havens via infiltration and indoctrination of vulnerable communities in south America, partnerships with small countries to gather resources, essential skills...... They knew to become expert tunnel builders, and they had maps of nearly every large city in the world that documented the smallest details. There's no 'fail fast and learn' in their case, and while they, thankfully, did not win, they managed to make a massive horrendous impact to advance their cause. While I don't plan to take over the world, there's a lesson to learn there and for me it's that there is merit to planning, and there is merit to knowing the territory. The question for me is, when it comes to starting a small business, what does successful planning LOOK like?
Well I think what you say kinda reinforces the quotes meaning exactly. Some level of planning is necessary even though life is messy and things aren't going to go according to plan. You're wondering what are some exact tactics and strategies which have a higher than average chance of success to give you at least a fighting chance...
Well, two recommendations.
Whether you are in B2B or B2C, give the book Lean B2B a read. Incredibly practical book that focuses on courses of action to take when starting a B2B business. So you can find tactics and strategies in there.
Secondly, my thesis on maximising the chance of success boils down to systematically reducing uncertainty by gathering information en masse across as many relevant domains as possible, as deeply as possible. You can't plan for what you don't know, but if you cast your net of knowledge and understanding wide enough you will be able to plan in such a way that there are less unforseen things you didn't plan for. So the algorithm is simple really... Do the best job at planning that you can figure out how to do, continue to study every domain you can, execute and revise as you go and update your plans based on new information.
Does that make sense?
Be like a toddler. Ask a lot of questions.
The most important thing I learnt in law school is the following: "Robin, the answer does not matter. Asking the right questions matter"
My mantra for planning is simply to be like a toddler: Ask a lot of questions. Toddlers ask hundreds of questions and that's how they grow. Embrace being of inquisitive nature.
Different questions, at different stages.
For those who do not have a product yet:
Develop yourself: Do you try to learn from other mistakes (IndieHackers is great for that)? Do you know the areas you are not good at and are you doing something for it? (communication, execution, analysing business ideas, or even general business skills, or simply overcoming your fears of starting?)
Test and fail: Do you test your assumptions and ideas to the market? Did you find the right product? Is there a right value proposition? Is it the right way to distribute and market your product? Are you talking enough to customers or are you just biased? Is the pricing correct?
For those who have a product and sales and want to scale (my current stage):
My issue is over planning to paralysis.
I would hallucinate that you may be overcomplicating things. This is something I was afraid of happening and something that I was doing, and then I realized that brainstorming isn't the same as planning, or road mapping - per-say. I started to write up the elaborate sales process, and was even tempted to buy a book on it, but I'm not planning a sales organization nor do I need one. So I though, "how can I do this in the simplest way possible?" And from that I chose 1 extremely simple path, and planned around that until I could come up with the specific action steps around it. I could simplify my roadmap and plan even more. Instead of using a CRM I could probably just use a spreadsheet. Cheaper and probably faster since almost everyone knows how to use one!
you right
you right
p.s - your name is the shit lol
dude I was so surprised it wasn't taken! #winning!