The Power of Deep Thinking

How to know when to give something more time and space before getting it out into the world.

Each of the last two weeks I have written a Messy Human post, then realized it needed more thought. As a result, I didn’t post. I’ve been debating whether this is due to some level of perfectionism, or whether these posts really did need more thought.

I struggle with the push pull of “action versus reflection.” I have a desire for both of those good things, yet they don’t always seem to peacefully co-exist.

In today’s fast-paced world, with high value placed on a bias for action, it can seem improbable that the best way forward is sometimes to let something simmer before rolling it out.

On the flip side, when you know something is complex, it can be difficult to give up on clarifying, perfecting, and polishing, even though there are declining marginal returns to your tweaks.

How do you know when to hit go, and when to give something more time and space for rich refinement?

When Deep Thinking Adds High Value

Deep thinking is a combination of reflective and analytical thought, which:

• creates awareness of what we think, feel, sense and know

• intentionally questions assumptions and beliefs

• seeks out new information and perspectives, and

• integrates it all to make our choices, outputs, and actions better

So when is this kind of thinking needed? Honestly, I’d say practicing it every day is a good way to shape your thoughts and actions for the better.

But what about the specific situations where the action-reflection polarity seems to be in conflict? Times such as when you have a big deadline at work, when an important choice is on the line, or when you need to bust out some bold moves.

In my mind, knowing when to make room for deep thought is all about understanding the value-add it brings and how much that value-add will counteract any potential negatives that could arise if you act too fast. Will that deep thought de-risk your results, significantly improve whatever you’re creating, and make your efforts more beneficial (to yourself or whomever else they are designed to benefit, like your customer or your spouse)?

Here are 3 signs that you could benefit from giving something deep thought:

1. You’re Stressed

2. You’re Doing Something for the First Time

3. You’re Doing Something Complex

Let’s dig deeper:

1. You’re stressed.

When you’re stressed it can seem that there is absolutely no time to slow down to consider things more deeply. You might have a big deadline, or a thousand balls in the air. You’re worried or rushed. Slowing down seems like the last thing you could possibly do.

This is exactly when stepping back to question your assumptions and beliefs will help you prioritize, see truth more clearly, take right action, and raise any red flags that might otherwise get left ignored. Stressed brains have been shown to make worse decisions in all kinds of research studies.

One of my most embarrassing moments at work was midway through a critically important presentation to a member of the C-Suite at a Fortune 500 company and her team of EVPs. After presenting the majority of a proposal for a new program, its contents, and roll-out schedule, I found myself presenting some problematic slides.

My new hire and I had gone back and forth for weeks on her portion of our proposal and the relevant slides. It took till two days before the big meeting just to get her slides to tell a coherent story. Then, when I finally understood what she was trying to say, her ideas didn’t jive with the business situation at hand. I asked for more changes, but the day of the presentation arrived and she hadn’t fixed much.

Frustrated, but in a rush, I didn’t have time to tell her the slides were out, and why. I also had nothing to replace them with. So, I left them in.

And I got reamed for it.

As soon as the top leaders saw her first slide, they called out the same issues I saw. And they began questioning my expertise. I knew immediately that in my exhausted stupor, I’d let my stress and sense of hurry lead me to do the wrong thing. Instead of being complacent, I should have yanked out my new hire’s flawed work and left our proposal slightly incomplete.

Unfortunately, the politics between our leaders were so thick they practically crackled in the air. At the first sign of weakness in my work, they all started trying to distance themselves from it, despite the fact that I’d already gotten prior buy in from each one of them.

This was the make-or-break moment where, as a team, they could agree on the final contents of the plan and the roll-out schedule, or they could stop us in our tracks. To save the bulk of our proposal, I had to immediately stop the presentation, apologize and eat crow about why the slides where there, and declare that section a work in progress merely hinting at what was to come. I promised to address the issues before our roll-out timeline. It should have been a victory lap for my team, but due to this misstep, the meeting barely got to consensus.

Would I have benefited from less last-minute polishing of the deck and more time spent thinking holistically about what we truly needed to include? Absolutely.

So, if you find yourself in a high-speed, high-stress moment, carve out some quiet time for yourself:

• Step away from the work

• Turn inwards and listen to your thoughts, notice your feelings, let red flags fully come into your awareness, question your assumptions and beliefs

• Give yourself the time to do something else, like take a walk, wash the dishes, or sleep, before coming back to the work or making any decisions

• Make choices from a place of quiet, calm and power, not hurry, stress, or fear

2. You’re Doing Something for the First Time

When you’re doing something for the first time, it’s a lot easier to make mistakes than when you know the path well. This is precisely the time to slow down so that you can seek out more perspectives or even run a test.

I can’t believe how much I’ve been able to learn from pilot testing risky new initiatives.

For instance, at a time when I was evaluating a handful of new data tools that could each generate unique new insights for the business that my strategy team supported, there were lots of contenders excited at the prospect of setting up a major deal with us. We reviewed plenty of impressive demos from technology companies offering us the moon.

But it wasn’t until we’d tested the most promising handful of tools that we were able to evaluate which ones really had fresh new information to offer, were actionable for our business stakeholders, and which connected directly to the strategic pillars of our voice of the customer program.

It was surprising to discover that among so many super cool technologies, each of which seemed promising, the majority led us nowhere due to small discrepancies between how they seemed to work and how they really functioned.

Disappointing? Yes, but by spending a few weeks or a few months (and often zero dollars) to test each of them out, measure results, and rate each one according to our prioritization criteria, we saved millions of dollars and years of effort in rolling out the wrong stuff.

Instead, we found two solid tools that were well worth their hefty price tags. Better yet? One of them helped our business stakeholders seek out customer perspectives in ways that a) decreased their costs when launching new products and b) lowered their inventory investment risks. Perspective seeking has measurable business value.

If you’re going to take the time to seek out new perspectives or test something out, here are a few tips to make it count:

• Understand and document your goals. Perspective seeking is a great way to find out what those goals need to be.

• Have lots of conversations. Keep them casual. Ask about needs, issues, and request advice (not feedback) about your own ideas.

• Map out the stakeholder groups affected by anything you’re doing, then make sure you’ve received input or feedback from representatives of each group. Give the time and space necessary to actively listen, honestly integrate feedback, and act on it.

• Ideate and brainstorm ways to test new things in small ways. There are no wrong answers in brainstorming and tests don’t have to be a big deal. I happen to know that even at a behemoth like Nike, they’ve tested out new services using a handful of free tools that were manually operated on the backend by a pilot test team.

• Know how to measure your test results against your declared goals. Develop non-subjective evaluation criteria for anything you test that doesn’t come with it’s own clear metrics.

• Have a prioritization or evaluation framework that maps results and goals to a clear set of decision-making criteria. Know when something is worth acting on by mapping out specifics about “how we’ll know” in advance.

3. You’re Doing Something Complex

Mark Twain was famously attributed the quote “I didn’t have time to write a short letter, so I wrote a long one instead.” Boy, do I feel that.

It takes time to distill complex ideas and problems into clear and simple messages and action plans. When you know you’re doing something that’s not straightforward, check in with yourself to see if you might benefit from giving the work time to simmer.

As I was about to hit “publish” on my last two Messy Human posts, I did this self check-in and had to be honest: I could be clearer. I could be simpler. I could distill the ideas further and make them more refined for the benefit of both myself and my reader.

With a sigh, I didn’t hit publish. Instead, I let the work sit, gave it some thought, had conversations about the work with people whose perspectives I value, and considered what it was I really wanted to say. I’m still working on both those posts.

As I do, I see frameworks emerging that will make the writing and my points much clearer and more useful. I’m determined to bring these frameworks to bear, if I can.

If you, like me, find yourself wrangling with murky ideas or complicated projects, consider the following questions before you jump from thought into action:

• Is this concept as simple as I could make it? Have I edited out all unnecessary words, paragraphs, stories, asides, or other thought junk?

• Is the plan as “straight to the finish” as it could be, or have I allowed some meandering or added steps to pad the work?

• If I look ahead to my target goal state and worked backwards to identify my critical path to getting there, would all my planned steps really be needed?

• Are there a lot of angles to this idea? When I play around with these angles, looking for the various ways they fit together that tell a story, do I see a framework starting to emerge? Maybe some pillars or themes?

In the age of fast-action, it’s still valuable to leverage the power of Deep Thought from time to time… or every day. It doesn’t always slow you down. Often enough, it’s a method of slowing down to speed up. Use it wisely and you’ll soon see the results bearing fruit.

Here’s to your deep thought, and mine.

Best,

Marisol