What holistic thinkers do differently from the rest

Every now and then at Google, I get to work with people who have a knack for saying things that make me go:

"Wow. How come I didn't consider that?"

I used to think it was just because they were smart. Or experienced. Or both.

But over the years, I've realized it's something different.

They've simply trained themselves to think holistically.

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Holistic thinking, defined

What is holistic thinking, exactly?

Here's a confession: I'm not sure how to define it properly!

But just as that famous Supreme Court quote goes? I know it when I see it.

Because when I work with top performers, I almost always notice the following patterns:

• They challenge assumptions
• They ask questions that aren't obvious
• They consider subtle yet important trade-off's

And so over the years? I took a lot of notes.

I wanted to capture the types of things they think about – so I could steal with pride myself.

And here is what I've observed:

1. They think beyond their own org.
2. They account for context.
3. They look ahead. Far ahead.
4. They consider incentives.
5. They challenge assumptions.
6. They focus on the meta-message.
7. They think about opportunity cost.

#1 They think beyond their own org.

Holistic thinkers are trained to see the big picture. They are rarely satisfied with only checking their own team's boxes.

Instead, they ask questions like:

• How does this affect other cross-functional teams?
• How does this fit into company- or org-wide objectives?
• Can I execute in a way that benefits other teams as well?

As an example: imagine that we're considering whether or not to build a new product feature, which is supposed to drive new user growth.

❌ Simplistic thinking:

• "Building this new product feature will help us grow users, which is good, so we should do it."

✅ Holistic thinking:

• "Our org-wide strategy is to eventually monetise premium users; are the types of users we acquire here right for our overarching strategy?"
• "At least 2 other teams have similar user growth objectives, yet we're all going about it separately. Is there a chance to pool resources and create more leverage?"

#2 They account for context.

Holistic thinkers always think about context when making decisions.

For example, imagine that we've decided to kick off a new business planning process, and we're planning to take the proposal to our stakeholders.

❌ Simplistic thinking:

• "This is a well-thought-out process that will instill operational rigour, so we should start socializing it right away."

✅ Holistic thinking:

• "This month is extremely busy and stressful for the team due to quota pressures. There is little mindspace for anything else. If we simply dump this on people, it will not get the buy-in that we want."
• "People have gone through multiple process changes and there is a sense of fatigue and distrust. What can I do to assuage those fears? How can I find allies or champions?"

Or, consider this situation: you're pitching a business case to your stakeholders, but you're struggling to get buy-in.

❌ Simplistic thinking:

• "They just don't get it. I need to pitch harder and bring more datapoints to convince them."

✅ Holistic thinking:

• "What context might we be missing? e.g. Have we been perceived to under-deliver in the past? Have decision principles changed to favor initiatives that carry less risk? Are there competing priorities we're not aware of?"

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#3 They look ahead. Far ahead.

In the early days of my career, I would usually tackle problems by optimizing for efficiency.

And so I would get the job done quickly. But it would also lead to things like:

• Setting up processes that wouldn't scale in the future
• Conducting analyses in a way that couldn't be replicated
• Ignoring maintenance debt that might creep up in the future

As time went on, I started noticing what top performers did.

It turns out, they rarely jumped at the most obvious or fastest solution. Instead, they approached problem-solving with long horizons.

They would then ask questions like:

• "How can we set things up in a highly scalable manner?"
• "What risks are we creating in the future by ignoring edge cases?"
• "Can we contribute to institutional knowledge by building robust documentation?"

Here's an example. Imagine that you've been asked to pull some data to help validate a hypothesis.

❌ Simplistic thinking:

• "This is easy. I'll just write a script, pull the data, send it over, and move on."

✅ Holistic thinking:

• "I can foresee this being a recurring need, given the underlying business question. Instead of doing a one-off pull, would it be worth setting up an automated dashboard instead?"
• "I believe other teams may have similar questions in the future. Can I keep them in the loop and include more dimensions in my analysis, thereby addressing their future needs?"
• "The data is complicated and people might have ongoing questions. Besides creating good documentation, can I set up a live walkthrough session for them, thereby saving myself time in the future?"

Holistic thinkers always think ahead. And their solutions tend to stand the test of time.

#4 They consider incentives.

Holistic thinkers are highly cognizant of incentives.

So instead of getting frustrated or even offended when things don't go their way? They're able to take a dispassionate view and unpack the motivations at play.

As an example:

❌ Simplistic thinking:

• "I have a fantastic proposal for a new process, and if I pitch hard enough, people will eventually see the light and agree to adopt it."

✅ Holistic thinking:

• "I have a fantastic proposal, but I anticipate some pushback because of mixed incentives."
• "I know A works on high-velocity deals, and this new process will be perceived to slow them down. What can I do to address those concerns?"
• "I also know that B was a huge proponent of the old process, and this new proposal may appear to be negating her past efforts. How do I address those concerns?"

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#5 They challenge assumptions.

I've previously written about the importance of first-principles thinking, and how it is critical for earning trust at work.

Because the thing is this: you can only make good decisions if you start out with the right assumptions.

And holistic thinkers rarely take assumptions for granted. They're trained to make sure their logic chain is tight, every step of the way.

So, as an example:

❌ Simplistic thinking:

• "Investing $xxxK to build this product feature is projected to bring 5% more new users, which is an incredible CAC (customer acquisition cost). Therefore, we should do it."

✅ Holistic thinking:

• "Why is growing users the right objective for us? Why is that the best use of resources right now?"
• "We're assuming 5% uplift based on past experimental results, but what needs to be true for us to make that extrapolation? Is it apples to apples?"
• "What benchmarks are we using to assess our CAC? Why wouldn't we apply stricter or looser thresholds? What does it imply about our growth strategy?"

#6 They focus on the meta-message.

It took me a while to learn this – but we signal a lot more than we think at work.

For example:

• What we think is happening: We send out an email to explain a new process, and include a lot of details in order to be helpful.
• What is actually being signaled: "This is a very complex new process, which is why it requires so much explanation."

Or, consider another example:

• What we think is happening: We ask somebody to take the lead on an important workstream, and they fail to deliver. We step in at the last second and take care of it, since it's faster for us to do so.
• What is actually being signaled to the other person: "Seems like my role wasn't that critical after all. I was right in not prioritizing this since someone else owns it."

In fact, let's compare the following three scenarios, where technically the same message is being delivered – but just executed differently:

1. You receive a ping from your manager: "Hey, the numbers on this slide look a bit off – could you double check quickly? Thanks."
2. Your manager sends you a long email listing out 5 instances where the numbers on a slide appear to be inaccurate.
3. Your manager sets up a meeting with you, and uses the entire time to validate the sources and assumptions for all the numbers on a specific slide.

Regardless of what your manager actually intended to achieve, you've probably translated the "signals" into the following "stories" respectively:

1. "My manager is comfortable with my work; they just want to double-check to be sure."
2. "My manager does not have full trust in me and wants to be extremely prescriptive. Otherwise, they wouldn't have taken the time to write such a long email."
3. "I'm confused: is my manager so distrustful that they have to babysit me like this? Or is it that they simply need to represent my work in very high-stakes forums (and cannot risk any errors)?"

In other words: doing the right thing isn't good enough. Holistic thinking requires you to nail the "meta-message" as well.

(Related read: how to avoid self-sabotage from unintentional signaling.)

#7 They think about opportunity cost.

It's easy to evaluate a decision on its own. It's much harder to also evaluate the implied opportunity cost and ask things like:

• "Is this the best use of time / effort / resources across the board?"
• "By choosing to do this, what am I deprioritizing by implication?"

So, for example:

❌ Simplistic thinking:

• "Our product is still buggy and imperfect. Let's invest more resources into getting it to an error-free state."

✅ Holistic thinking:

• "There is a cost associated with improving the product. Is there an 80/20 solution that we're comfortable with? What features are more critical than others to fix?"
• "Which product issues have a direct impact on our sales process? And which bugs can we afford to take a risk on? What decision principles are we using?"
• "Where else could we invest the time and effort instead, should we choose not to optimize further?"

It's easy to be a perfectionist and demand high standards for everything.

It's also natural to simply focus on optimizing "your own thing" and tune out everything else.

But we live in a world with trade-off's. And holistic thinkers are trained to always think about counterfactuals.

For more on this...

Holistic thinking is tiring. It feels like you're creating more work and complexity for yourself.

Sometimes, it might even feel like you're thinking about things "beyond your pay grade."

That's why it's hard. But that's also why it's incredibly valuable.

P.S. To read more about operating principles for high performers, check out the following:

• How top performers make others better 
• What having a strong point of view really means
• Why extreme ownership is the key to success