The Introverted Entrepreneur, Pt. II: Temperament-Friendly Teamwork

In this second part of “The Introverted Entrepreneur,” we’re talking about embarking on the exercise of teambuilding and teamwork. Did you miss part 1 (on networking as an introverted entrepreneur)? No problem, it’s right here. Not sure what we’re doing? Start here.

As with this series’s first part, I feel compelled to start by dispelling a myth: introverts don’t hate people. An appreciation of solitude and occasional need for individual time has sown this nasty rumor, and I’m here to put it to rest.

Introverts (a) are capable of, and (b) truly enjoy, deep and purposeful relationships; this can be all the more true when these relationships are grounded in a common goal, interest, or objective. This means that once they find teammates and collaborators who they can work with well, they’ll be invaluable members of a team. We addressed a bit of the prospective synergy that introverts and extroverts can provide to one another in last week’s post; this week’s edition will allude to that as well.

How Do I Find These Folks?
In order to build substantive relationships that can not only fulfill you as a person, but also sustain the inception, growth, and development of a business, you have to find the people who would best fit your needs. This isn’t always the easiest, as we’ve already talked about. So I want to dedicate this portion of the post to other venues where these connections can be made.

First, my favorite, sending fan mail. I wrote with AND.CO earlier this year about the topic, and shared:

People love getting mail that isn’t bills, especially if those messages aren’t spam. After all, it’s always nice to know that your work is appreciated! So if you have a photographer that you follow on Instagram whose work always catches your eye, an artist whose work sparks something in you, or perhaps a blogger or columnist whose pieces resonate with you, send them a letter!

Now, it’s not a given that this piece of fan mail will yield an offer to work together. In fact, it’s pretty likely it won’t—but they do have the potential to start a relationship. Unlike the fan letters we used to send to heartthrobs as kids, these letters stand a stronger chance of standing out and making an impact. Relating on a professional and personal level could uncover commonalities that would be a natural fit for a joint project.

And ultimately, that’s the deeper purpose a collaboration is designed to fulfill. Whether the final product ends up being a podcast, joint article, shared promotion, co-taught class, or anything else you could choose to team up on, it’s about making the [entrepreneur] world feel a little less lonely. Even when we know the work we do is important, it can be hard to feel that way with little interaction or feedback. Consider collaboration as a way to keep your work fresh, original, challenging, and rewarding.

A preemptive note to this: fan mail should not be sent as flimsy pretext to ask for something. Trust me, the recipients can tell the difference. Genuine and earnest overtures of appreciation can get you somewhere; calculated openings for asks likely won’t.

Interested in the community of an online forum? Strategy or mastermind groups are possible and fruitful in spaces like Facebook, via Twitter using hashtags, and can even be conducted more intimately on platforms like Snapchat, MarcoPolo, Slack, or GroupMe. The key in these spaces is to watch (or “lurk”) as you enter, contribute knowledge where possible, and monitor the norms and expectations of a group space before making asks. Again, the asynchronous nature of those groups eases the burden of conversation, allowing introverts to take their time in contributing to a conversation or providing a response to a tough query. What’s more, an accessible archive (save Snapchat-based groups) means that you can come back to a topic or exchange later on- this isn’t always a comfortable thing to do in in-person conversations!

And finally, you can flex your connections with current friends and colleagues. While reaching out cold to folks might feel intimidating (a truth regardless of temperament, I want to make clear!), doing so with an assist from someone you already know can bear fruit in ways you might not have expected. For the last two years, I’ve hosted a blog series called The Defectors; as my existing connections run dry, I turned to previous contributors to help me find my next set of collaborators. These recommendations, coming from people who know me and who I trust, can strengthen “weak ties” (as in “I don’t know them, but I know of them”), remind me of strong ties I may have overlooked (“oh yeah, I could ask her!”), or create new links altogether (“this person sounds great, please connect us!”). This strategy, used on previous projects, led me to my current podcast hosts, a founding member of my current mastermind group, and several other frequent collaborators. Whose existing ties could lead you to the next great breakthrough for your business?

At the same time, it is essential to remember as an entrepreneur that your circle of friends and circle of professional connections don’t always intersect in a way that’s productive. What we’d hope would be a large intersecting area in a Venn diagram, might instead turn out to be only a sliver. That’s okay, often to be expected, and the best reason to employ several of these strategies together.

How Do We Create The Best Version of A Working Environment?
As someone deeply interested in temperament and how it affects how we work and live, adages about lapses in communication being the cause of conflict (“10% of conflict is due to difference of opinion, and 90% is due to tone of voice”) resonate as incredibly true to me. And in my work as a facilitator with teams and organizations centering around conflict, I see several versions of this in practice. When we parse it out as a group, I typically narrow it down to two dynamics: tending toward being quiet versus tending to talk things out; and preferring solitary work versus working in a communal/open environment. Recognizing, of course, that there is nuance in these classifications, it nonetheless works to help participants understand the differences that often accompany temperament.

The exercise encourages participants to share their first assumptions about why their “opposites” behave as they do, and then the true motivations behind those actions are shared. The result? The next time someone doesn’t contribute as expected in a meeting, or opts to work with their door closed, someone who works differently has the context to push past their assumptions- recalling and therefore revealing the actual motivation for that action. “Francisca wasn’t not listening, she just needs a bit more time to think about what we posed in the meeting.” or “Jarvis isn’t mad that it’s so loud in here, he just needs the quiet to access his thoughts.”

I say all this to encourage you, as a business owner and in turn as a custodian of a budding working environment, to prioritize understanding the work style and work preferences of those who you work with. How flexible are you willing and able to be? What are your organizational expectations and, for that matter, dealbreakers? And in the work environment that you’re building, do people have the opportunity to know one another well enough to distinguish temperamental differences from quirks at best (and character flaws at worst)?

What Happens When Conflict Arises?
As I alluded to above, a better understanding of what communication styles might represent is essential when trying to mediate and resolve conflict. In fact, I recommend setting ground rules during “peacetime” for how conflict will be handled. These ground rules can be based in individual challenges, and serve as an aspirational way to improve our typical communication patterns.

For example, while I am incredibly slow to anger, I will sit on small annoyances…only to see them explode on my friends, coworkers, or loved ones after they accumulate. So a ground rule I would set for myself would be to tell a person when something is bothering me, in a timely fashion (24 hours or fewer). Someone who seeks to deflect blame toward others might set a goal of taking three breaths and examining the multiple sides in a conflict; an individual who struggles to engage in conflict at all might aim to reflect on feelings before sharing them with others. In all these cases, creating a strategy that allows improvement upon our occasionally unproductive instincts, can change the way we engage in these issues.

What about confronting the conflict itself? A good rule, irrespective of temperament, is to face as much of the situation face to face as possible, but allow any time that is needed to de-escalate or reflect on the issue at hand. This dual-pronged strategy prevents some of the ambiguity of tone that can come from asynchronous communication, but also allows each party the time and space to choose their words intentionally. It also addresses each “type”‘s challenges with care. While introverts can sometimes struggle to articulate their challenges in real time (especially during points of high stimulation), having the grace of “let me think about how to say that” can yield a more cogent argument when it comes to them. Similarly, while slowing down might be difficult for individuals who talk and think nearly simultaneously, the challenge to slow down and choose words more intentionally might prevent some of the hurt that can come from speaking extemporaneously.

Recognizing that the nature of entrepreneurial culture means that the people with whom you’re in conflict are likely both your colleagues and your friends, it can seem dismissive or trite to encourage a separation between personal issues and professional ones. But I promise you, it’s possible. Ad hominem (“to the man” in Latin) attacks, or ones directed toward a person rather than the issue or challenge at hand, can destroy key relationships. This means preparing to tackle a situation with an understanding of what’s really upsetting you or causing a problem. To be clear: this is not always easy to do. Drilling down into the issue with a “five whys” approach (starting with what you see as challenging, asking “why,” and being honest; after five “whys” the problem often looks very different) may help you gain some clarity on the root issue, and not just the symptoms that may finally be starting to flare up. Once you’re at the root cause, any healing remedies you elect to put in place – together – will have a better and more lasting chance of yielding a cure.

This guide is in so many ways a means of scratching the surface on this topic. What tips do you have that I should think about adding? What challenges might I have missed? Would love to hear from you!

Further Reading From Me: