Skillful Thinking — 13 Habits to Help You Innovate

“If you have a golf ball sized consciousness, when you read a book you’ll have a golf ball sized understanding, when you look out, a golf ball sized awareness, and when you wake up in the morning a golf ball sized wakefulness. But if you could expand that consciousness, then you would read the book with more understanding, and when you look out, more awareness, and when you wake up more wakefulness — it’s consciousness.” — David Lynch

Thinking, it seems so fundamental and obvious. Everything we do requires thinking, but there are nuanced cognitive behaviors that affect how we think, process new ideas, and even manage our time.

These practices profoundly impact decision making, innovation, and one’s ability to lead products and people. Thinking is the most important skill you have. Honing this skill allows you to generate novel ideas, anticipate issues no one else sees, and gain a unique perspective on user problems.

So what does it mean to become a skillful thinker? Simply put, you have to do the kind of cognitive work that few are willing to do. It means doing things in a way that most others are not — and in some cases, it means unlearning current behaviors.

The difference between important and urgent

To develop skillful thinking, you need to make time for it. To make time for it, you need to change the way you work. Most of us spend the majority of our time in reactive mode: reading and replying to emails, attending meetings we are invited to, etc.

Many PMs spend most of their time responding to inbound feature requests, triaging bugs, putting out fires and blocking and tackling the next most pressing issue. To a large degree, this constitutes the bulk of their work, and things like achieving “inbox zero” are viewed as crowning achievements. But there is a price to pay for being on top of your email. Operating solely in reactive mode gives one a somewhat false sense of accomplishment.

Genuine accomplishment, whether that be devising a new operating model or innovating a product, comes from conversations, uninterrupted thinking, reading and writing.

Every day I write down the three most important things I need to get done. Between back to back meetings, this takes up almost all of my time. This approach allows me to address what I deem to be most important. But a by-product is that I am not as responsive as I would like to be when it comes to email and other inbound distractions. I do email on the train to work and in the evenings. First I answer email from my team, than my peers, than others at the company. I rarely get to all the internal emails. If you are external, forget it. I am not going to read your email.

I have deliberately sacrificed email responsiveness to give me the time I need to get stuff done. I have traded that which someone else may deem urgent for that which I feel is most important.

Don’t Box Me In

One of the biggest mistakes organizations make is to unilaterally timebox agenda topics. These are arbitrary time limits one puts on a topic of discussion. We do this because we believe it is better to get through every item on an agenda than to have a conclusive and well-understood outcome of fewer items.

How often have you heard “for the sake of time, let’s table this discussion and move on to the next agenda item”? We believe this is efficient, and we are achieving more in less time, but that is an illusion. The reality is that deferred discussions are rarely revisited and given the time they need. We are walking away from often important topics with no clear understanding of the subject matter, the outcomes or action items.

With that said, it is equally, if not more important, to come to meetings prepared. Ideally content related to the discussion has been distributed beforehand. If you are the author of this content there are few things more frustrating than being peppered by questions that are answered in the materials.

If materials have not been distributed in advance (sometimes there simply isn’t time), have a rule that all questions should be written down and addressed in a Q&A after the presentation.

Status meetings, such as daily standups, do benefit from a rigid, timeboxed format. But status meetings do not require skillful thinking. I would argue that for most status update meetings, a meeting is not needed. A status email would likely be more efficient in communicating relevant tactical information.

Complex and nuanced topics, where the attendees each have a varying degree of understanding, should be given whatever time is necessary. If that means carrying over agenda items, then so be it. I would rather have a firm understanding of a single topic than a superficial understanding of several.

13 Ways to Practice Skillful Thinking

1. Always be on the hunt for new ideas and other points of view

Deliberately force yourself to stay in a mode of curiosity and open inquiry. Ask lots of questions. Take notes throughout the day and come back to them later. Set aside time in your routine to review these ideas and thoughts, give them the space and time they need for contemplation.

I maintain a running list of product ideas. I revisit them frequently, revising them and expanding on them, and figuring out when, if and how they should be validated. These ideas are both my own, and those I’ve heard from others that interest me.

2. Know what you don’t know

The best way to learn is to admit what you don’t know. It takes some work to figure out what you don’t know. The best way to do this is to ask yourself how you would explain an idea or concept to someone else. If you find yourself stumbling, you likely don’t know the subject well. When this happens (and it should happen frequently), make a note of it, and later take the time to read and write about it so you can clarify your understanding or position, both for yourself and anyone who may ask you about it. This post is an example of that.

3. Appreciate ideas for their own sake

Plenty of people want to learn about things because their job necessitates it, or because they already know what they’re going to do with the knowledge. But if you want to have the kind of ideas that others don’t, you need to pursue new ideas for their own sake — for the intellectual gratification that comes with grasping complex ideas. If you want to innovate, have creative flow, you can’t follow someone else’s rule book.

Creativity and innovation do not happen in a vacuum. Every great intellectual, cultural, philosophical, and technical breakthrough was built upon previous knowledge and the work of others. Elon Musk didn’t invent the electric car. Isaac Newton didn’t create the Calculus in a vacuum. Perhaps our century’s most revered innovator, Steve Jobs, created not a single wholly original product: the Apple I wasn’t the first personal computer, the MacIntosh wasn’t the first windows-based UI, the iPod wasn’t the first MP3 Player, nor was the iPhone the first smartphone.

4. Know what you don’t need to know

It’s equally important to identify what you don’t need to know or to deliberately limit your depth of understanding and be comfortable with it. Limiting your scope of understanding is particularly important as it relates to product, engineering and company information. There is simply too much of it to gain a substantial and non-superficial understanding of everything. If you try, you will fall into something similar to the “inbox zero” trap. All you will have time for is consuming information, leaving no time for creating ideas and driving results.

This is especially important for product leaders and necessitates empowering your team with sometimes little or no supervision. If you manage a Product Group or an entire Product Area, it is impractical to attempt to understand every detail and doing so is not how you can add the most value. In fact subjecting your team to frequent and detailed inquiry may leave them feeling untrusted and demotivated. Let your team become the experts, and spend your time coaching them for growth and how to navigate the best path forward.

5. Be willing to entertain opinions and ideas that others dismiss

There are ideas that others toss away because they don’t want to work with them. Nearly every seemingly bad idea can be useful in at least one of three ways: 1) understanding the underlying principle of it; 2) understanding what other ideas might be connected to it; and 3) gaining a deeper understanding of what doesn’t work. There is fertile ground in disassembling and re-assembling ideas to cultivate new ways of thinking and understanding the best path forward.

6. Write… a lot

One of the best ways to clarify and cultivate thoughts is to write. Just sit and write. Put pen to paper (or fingers to keyboard) and get your thoughts and ideas out. Push yourself to explore the depths of your mind. Some of these ideas will spark and set you on a journey of creation.

The purpose of writing is to explore, organize and clarify ideas. These ideas are rooted in a tangled web of thoughts and ideas that mostly originated outside of yourself. From something someone said, from a book you read, or a painting you saw. Or a long meandering late night conversation you had with a friend.

7. Read… a lot

Don’t limit yourself to books relevant to your profession, read about things that interest you. Don’t know what those are? See the next section.

8. Diversify your Interests

I love technology, but the reason I left San Francisco is that all anyone ever talks about is start-ups and tech. I also love art, literature, film, philosophy, architecture, industrial design, music, fashion, theater… the list goes on. The people I spend my time with are nerds, which to me is just a euphemism for someone deeply passionate and knowledgeable about something. I love to learn from them. I feed off of their excitement and passion, and it ignites my interests.

9. Be willing to do the work of making connections between things that seem disconnected

True intelligence and creativity come from being able to connect things that others haven’t thought to connect. And the great thing is that connections are there between pretty much any two ideas. It’s just that some of those connections are interesting and useful, while others are not. But the only way to determine this is to think about them.

A useful exercise for PMs to practice regularly is to consider your product as a user would. Forget about internal politics, org structure, experiments, MVPs, etc., and consider the product as a user would. We have discrete work-streams and teams for practical reasons, but in doing so we run the risk of “shipping our org chart,” which is to say, losing sight of how a user will experience our product because we are biased to the internal workings of our organization. In imagining yourself as a user, ask yourself if the experience truly is viable. Or, for the sake of our own internal rational, have we crippled the experience by delivering an incomplete product.

Product Management is an art as much as a science, and we have to force ourselves to think critically as a user would. The user doesn’t give a shit if we are trying to prove a hypothesis. They don’t care that we had to cut corners due to dependencies or someone’s vacation schedule.

10. Ask a lot of questions — even to the point of annoying people

There are few better ways to gather ideas and gain insight than by asking questions. Some people are receptive to this, and some people are not. You obviously don’t want to seem as if you don’t care about others’ time or about making progress, but you do want to push others to address your questions and push yourself to find out as much information as you can.

11. Be slow to action

These days, people demand quick action. People want to be quick to market, early adopters, etc. That’s fine, but that’s where you will have to be willing to act like no one else. You have to resist the trend to act quickly, especially when it seems like the action is merely reactive, as opposed to coming from a place of new and exciting ideas. I’m not saying there’s no virtue in quick action, it’s just that many people act quickly, but not thoughtfully — you don’t need to be another one, especially when you could be cultivating a better way of thinking.

12. Set aside time for just thinking

Turn off your phone and any other distractions and just think. Allow thoughts to happen. When one ignites, start writing things down. You may soon find yourself in the “flow,” with connections and ideas arriving with absolute clarity. Even a quick walk around the block can reset your brain, allowing you to return to your work with fresh thinking,

13. Set aside time for not thinking

Learn to meditate. This practice is perhaps the single most impactful thing one can do to open up creative pathways. All of us are cognitively burdened, and meditation as a daily practice is like rebooting your consciousness, allowing new synaptic pathways to form and new patterns to emerge that were hidden from view. Meditation expands your consciousness. Meditation is about centering one’s consciousness in the moment and freeing your mind of intrusive thoughts that take you out of the present tense. Meditation does not have to mean sitting cross-legged in silence. Activities such as listening to music, dancing, vigorous exercise, playing an instrument, or riding a motorcycle can also bring you to a similar state of consciousness.