Great Leadership in Startups

Often times at a startup you may hear that positional titles don’t really matter. In fact many of the mentors who have truly “experienced it all” that I’ve met throughout my journey at Team Typed have likewise strongly cautioned against Chief Officers at the early stage.

My interpretation of such advice, which I now realize to be very appropriate, is that nominal leadership at a startup is unimportant, and perhaps even premature and an organizational risk, unless you’ve all really made it through the tunnel. 

Yet, in the corporate world distinct job titles that reflect clear roles and responsibilities, especially for manager-level positions, seem to be the basis of a well-functioning organization. Then is the cautionary tale against positional titles a mere result of startups being the mavericks they are, revolting against traditional frameworks?

Titles Don’t Define Leadership

Well, from my perspective, it’s not a discussion of why titles shouldn’t matter, but why titles don’t matter all that much. First, it’s really one of the very last things that you will be concerned about at an early-stage startup when everything is uncertain down the road. It’s much like how exponential growth in the value of stock options can be realized if and only if there is an exponential growth in the value of the startup itself.

What does matter is not whether you are the Chief Operating Officer, the Director of Business Operations, or the Head of Sales Ops, but an individual’s tangible contribution to the growth of a startup that we often conceive and define as leadership. It’s about the matter of leadership, not about what it should be called. To borrow from a rather extreme case, Elon Musk’s self-coronation as Techno King helps us realize that the C-titles that we feel “right” about were, at one point in history, made up titles too.

The Key Takeaway

So what’s the takeaway here? Should an early-stage startup be nominally void of a C-suite? Through the latter part of this blog, I want to try and articulate that the takeaway is that leadership at startup should transcend positional titles. Why? Because the leadership of every teammate at an early-stage startup, often small and fast-moving, is the defining basis of its success. As famously brought forth by Peter Thiel, the difference between 0 and 1 is ultimately the startup’s raison d’être.

Therefore I’d like to make my contribution to our general perception of leadership in a way that fosters both the mindset and the agenda that can help address what really matters, which is to approach leadership as a behavior. 

What is leadership? Is it a mindset? A tangible set of acquired skills? An innate talent? A “must” for MBA students and C-level executives? Even if we could just have one answer to the question, then what?

Leadership can be defined in a myriad of ways. However, as mentioned, I’d like to take the approach that treats leadership as a behavior in this particular blog. In this sense, the word ‘lead’ that constitutes the topical concept of ‘leadership’ may be, in my opinion, misleading.

This insight was primarily influenced by Peter Bensinger, Jr., also dubbed by American Lawyer as “The Most Wired Lawyer in America.” During my study at Yale, I was fortunate enough to take a course on leadership led by Peter, who delivered to me the perspective and the resulting discipline below.

How does defining leadership as a behavior differ from our traditional understanding of the subject? Behavior is an accumulation of actions and mannerisms performed by individuals, largely in interaction with others. In this vein, leadership can be deemed less of an axiom and more of a set of tangible actions that we carry out throughout our lives.

Positional Leadership vs Behavioral Leadership

Before I go any further, I have to emphasize the distinction between positional leadership and behavioral leadership. Positional leadership (e.g. CEO, professor, governor, etc.) is authoritarian by nature. It provides a certain level of assumed superiority through procedural transfer of power.

On the other hand, behavioral leadership, while still may be exercised by positional leaders, is voluntary and personal. In that vein, while positional leadership may be limited in terms of how many leaders there can be in a given relationship or organization, behavior leadership is not. There is no zero-sum calculus.

To return to the purpose of this blog–exploring leadership as a behavior–the conclusion that I want to deliver is this: leadership as a behavior is not only good, but to a certain extent necessary in any relational or organizational interactions (especially at a startup).

Leadership as a Behavior

Regardless of your position in any context, everyone should learn the skills of behavioral leadership, which include, but are not limited to, listening actively, taking on crucial conversations, making critical decisions and asking powerful questions. You may wonder what these skills really mean, and the purview here is merely to direct your interest in the subject. I provide below several fundamental behavioral leadership books that are part of a much expansive literature that will better explain the significance of the tangible skills and how to improve upon them.

  • “The Art of Active Listening: How to Double your Communication Skills in 30 Days,” by Josh Gibson and Fynn Walker.
  • “Power Questions: Build Relationships, Win New Business, and Influence Others,” by Andrew Sobel and Jerold Panas.
  • “Crucial Conversations: Tools for Talking When Stakes are High,” by Kerry Patterson et al.

In short, engaging leadership as a behavior is essentially improving upon your skills that can be applied to any interpersonal context. It is a rather macroscopic ‘how to better approach’ for your interactions with your partner, friend, boss, teacher, parents or colleagues. Thus the discussion is not necessarily whether a behavior is ‘good’ or ‘bad’. The conceptual approach in which I take on leadership here should defy such classification. Here, it is rather a discussion of ‘more’ or ‘less’.

In fact, there really isn’t such a thing as “too much attentive listening,” at least within logical boundaries. The more you engage with behavioral leadership, the better you invest in your interpersonal relationships for the good of those involved in your startup.

The discipline, which comes from approaching leadership as a behavior, that can be applied to any startup whose every teammate is indispensable is the following: embracing leadership as a behavior means becoming a better person and a better teammate of a startup.

Unless you decide that all of the above are not of any interest to you, I urge you to try the books listed above as a step towards uncovering the behavioral leadership that lies within you. In the behavioral sense, leaders are not born. These skills are to be consciously acquired, and more important is the awareness that these skills are in fact attainable by anyone.

Through this read, I hope that you can acquire the leadership behavior that will allow you to be a better teammate for your startup or, if you happen to be in a positional authority of leadership, a better leader. If you’re curious about other important elements within startups, feel free to take a quick read regarding Initial Stages for Branding Startups.