Have you ever been advised: “don’t overthink it”? I’ve been on the receiving end of this, and it always creates a little disturbance in The Force. I worry that:

• I’m uptight, or maybe that
• I’m a control freak, or even that
• I don’t know how to relax or have fun

 

And I mean, there are situations in which there would be a bit of truth to any of that.  But in general, I feel good about how tightly or loosely I hold things. So then what is it about this admonition that can have me second guessing myself so easily?

Especially given my general wariness about stifling discussion, it’s funny how often this one can get a moment with me, before I remember how much I value thoughtfulness, curiosity and intentionality. Usually, if someone curtails my or someone else’s exploration of curiosity – often not with outright dismissal, but with responses that ultimately have the same effect, for instance “it’s complex, more than what we have time to get into” or “I think we’re getting into the weeds here” – I’ll assume the intention of the inquiry just wasn’t clear enough, and try posing the question a different way. (Not suggesting complexity or weeds aren’t real and deserving of consideration, only that they can shut down other interests that may also have deserved consideration.)

The surprising difference it makes

“Don’t overthink it” is often advised in response to a suggestion of orderly planning, or anticipating needs, in a circumstance that is seen as inconsequential or routine. But the truth is, our experience of life is fully affected by our daily routines and unquestioned moments. As Adrienne Maree Brown says, “small is all”. 

Let’s think about intention for a moment. What do you hope for, from reading this article? Maybe to think about, or learn something useful, hopefully in an enjoyable way, and ideally in as little time as possible? 

Okay so what’s the difference between reading the article with a clear awareness of that intention, versus without? 

• Maybe you make notes, if you hope the reading is going to be useful in some way. 
• Maybe you abandon reading it, as you realize you’re not enjoying it, and search for a more enjoyable read on the topic. 
• Maybe you schedule more time to finish the reading, if it is long, but also useful and enjoyable. 

 

The thing is, just as intention is present in reading this article, intention is almost always present in all of our activity. It’s just not always “visible” or considered. Knowing what we hope for in any given situation – or undertaking, or conversation, or relationship – plays a big role in whether that hope will be realized. And yet there is a common way of thinking about this which assumes it only applies to momentous, major stuff – there’s no need to be mindfully intentional about the run of the mill, moment to moment minutia of life. Even those with mindfulness or meditation practices may relegate the practice to non-working time.

In workplaces, this might look like carefully crafted values statements, formal retrospectives on projects, and shared agreements for meetings, but… no intentional practices around informal, in-the-moment ideation or feedback. For instance: 

• subjective perspective may be treated as objective truth, with insufficient assessment or analysis. One person says “our presentation was boring”, and it triggers an actual plan to change the format of the next presentation, without much attempt to determine what the overall experience actually was for all who attended. 
• strong and articulate advocacy for innovative, popular, or compelling ideas may be insufficiently assessed. One person says “our sliding scale pricing is not as good as our competitor’s”, and plans are made to match the competitor’s sliding scale without examining implications or alternatives.

 

The more power – formal or informal – held by the person with the subjective perspective, the more likely it is that others will respond without sufficient assessment, but also, anyone can have this effect! Particularly in workplaces with some awareness but not great understanding of the concepts of team psychological safety (which I’ll very loosely define as the ability to share thoughts and opinions without fearing ridicule or reprisal), there may be some discomfort around raising critical questions.

Many easy ways to think better

In addition to this notion of “underthinking” I’m presenting, there are other notable hindrances to reliable, good quality thinking that turn up in our workplaces fairly commonly. 

In the Cynefin Framework, Dave Snowden talks about entrained thinking as “when people are blinded to new ways of thinking by the perspectives they acquired through past experience, training, and success”. Snowden says this is a particular hazard of the “simple” domain of work: the domain of routine and repeating, predictable action. The framework illustrates that what seems simple can quickly slip into chaos, partly due to this liability.

Another phenomenon in workplace collaboration is what’s often referred to as groupthink. Psychologist Irving Janis coined the term to refer to “a deterioration of mental efficiency, reality testing, and moral judgment that results from in-group pressures”. 

It can feel difficult to question something that everyone seems agreed on, so we may also indicate agreement even if we are questioning. But what if everyone else who seems to agree is doing the same thing?

I like to add this concept of “underthink”, for its presentation of an empty space to fill, rather than a full space to clear out. When teams or workplaces don’t carry their intentional creation of organizational culture all the way through the work structures, down to the routine moments, those routine moments may end up governed by whatever happens to be around: competition, confusion, coercion, resistance, interpersonal dynamics, assumptions, etc. In this way, “underthink” is driven more by absent conditions than by present ones. 

Take a look at the culture creation work your organization has done. How deep does it go? Wherever that is, that’s the place to start from, and see how you can extend those intentions further into the increments of how the work happens. Let’s look at an example. 

Goodest Dog Stuff

The company I’m making up for this example, Goodest Dog Stuff, has had terrific success since launching their original product, the Goodest Dog Harness, and have since introduced a whole line of Goodest Dog products based on their reputation for innovative features. As the number of people working on Goodest Dog has been rapidly and consistently growing, the founders have given a lot of thought to teamwork and employee experience. They established a set of values to guide planning and operations. The values are regularly referred to in internal communication, and are prominently featured in public facing communication too. One of these values is collaboration. 

With its identity rooted in innovation, and its constant introduction of new team members, Goodest Dog Stuff started to experience minor but consistent conflict and fewer completed decisions in meetings. Leadership decided to introduce what they called “shared agreements”, which some on the team had known elsewhere as “ground rules” or “participation guidelines”. These agreements would guide how Goodest Dog people would communicate and work together in meetings. They brought their values through these agreements, and one of the agreements informed by the collaboration value was “Everyone’s ideas are heard.” It didn’t take long before everyone had shared agreement that the meetings were even more chaotic.

Why do you think this happened?

There may have been a variety of reasons, of course, but I’m going to feature the one that’s aligned with my focus in this article. I’ll even quote myself to set it up:  

“…the culture creation work your organization has done. How deep does it go? Wherever that is, that’s the place to start from, and see how you can extend those intentions further into the increments of how the work happens.” 

Goodest Dog Stuff can definitely bring this great start – values, shared agreements – further into the increments of how the work actually happens. 

Were you thinking about what happens after “everyone’s voice has been heard”? You guessed it! At Goodest Dog Stuff, the agreement was quickly refined to add “and considered.”

But, cue “sad trombone”, this amendment was also not enough to keep them out of trouble.  Goodest Dog Stuff still hadn’t given thought to what “and considered” would consist of. A round of comments followed by voting? Comparison against targets or indicators set in the strategic plan? A bespoke assessment each time, guided by a group determination of “how should we assess these ideas?” 

They determined they actually had three different types of meetings happening regularly, and the purpose of one of them didn’t require collaboration at all. In another of the meeting types, they realized that many of the choices and decisions they’d been struggling with were part of the formal accountabilities of specific roles in the company. Hearing everyone’s voice was valuable input to decision-making, but wasn’t, itself, the decision-making. Establishing that clarity with everyone – the right expectations – made those meetings much smoother. In the third meeting type, they adopted a consent-based model. In all of their meetings, Goodest Dog Stuff began a practice of intentionally surfacing unspoken objections before concluding decision-making processes. At last, meetings returned to the dynamic and generative occasions they had been.

But the future was still not rosy for Goodest Dog Stuff, because ***lots of work happens outside of meetings***. Goodest Dog Stuff had always sought out high energy, creative, expressive, innovative team members. These people did not save this mode for meetings, it was always on. If two people happened to be heading out on their lunch break at the same time, the odds that they’d come back later, wide-eyed and delighted, with “the solution” or a “breakthrough” were pretty good. In this way, Goodest Dog Stuff was essentially always working on two roadmaps: the intentional one, supported by the structures and processes they’d learned added value; and the roadmap of spontaneous ideas that hadn’t been subjected to the same assessments. When some on the team noticed this and mentioned it, they were dismissed with objections like “this is literally how innovation works” or “we need to be nimble/agile/adaptive to compete in this market, and this is what that looks like”. 

See the many forms “don’t overthink it” can take?  

You might imagine an easy response to those worried about stifling innovation: clearly you can have ~both~ spontaneous ideation ~and~ quick and efficient evaluation of those ideas. But to be fair, it’s usually easier to think that way when reading an article, and less so when on the receiving end of being called “bureaucratic”, or “overdesigned”. 

How to spot and prevent underthinking

Unlike the Goodest Dog Stuff example, in which innovation was understood to be strategically important, more susceptible to underthinking are moments and activities whose strategic importance is harder to see. 

You can use a sort of reverse engineering to look for these instances. What’s a bump or trouble your team has encountered? I advocate Five Whys a lot as an approach to root cause analysis, and I’m going to again here. And don’t forget, five is not carved in stone – it may take more or fewer rounds to see what happened. If you arrive at anything that’s based on assumption (“we assumed they’d read the report”), that’s a hot clue! In general, keep an eye out for things overlooked, unquestioned, unconsidered. The nice thing about this approach for this purpose is that it is based in curiosity, which is the very quality we are talking about nurturing!

This is the kind of opportunity you can look for to create culture that encourages questions. Ultimately it takes more than structures like retrospectives to embed and uphold curiosity, thoughtfulness and intention into your organization’s values. A map is not the land it describes, although it can be great to have one when you’re lost. To have ready access to curiosity in the moment, the best way to start may be simply to ask, “What might we be underthinking about?”

If you think you might be able to improve the quality of thinking in your organization by structuring more intention and curiosity into planning and collaborating, we’d love to hear from you!