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  • Writer's pictureMolecular Ideas

Three Types of Successful Startup Leaders

Updated: Jan 27, 2022

Welcome to Molecular Ideas, and thank you for sharing your time with us! Today, we examine the three key archetypes and attributes of startup executives that are thrilling to work with and a privilege to work for. We also include a helpful matrix to guide your thinking.

Our Discussion at a Glance

  • Leadership style often boils down to two key factors: how we communicate with others, and the autonomy we provide them to do their jobs.

  • We have dubbed the three startup executive leadership styles as the Commander, the Jack-of-All-Trades, and the Dungeon Master. Understanding them may help you to better understand the pros and cons of your own communication and leadership style.

  • We identify five common benefits that all three of these leadership styles create (such as omitting 'second class citizen' status from the company culture) and pitfalls to avoid.

  • These leadership styles contrast those implied in our Whitepaper on Startup Fraud - that said, the only way to ensure long-term success is to remain reflective and vigilant.

The Other Side of the Coin

Recently, we deconstructed several case studies about fraud in the life science startup world following the conviction of former Theranos CEO, Elizabeth Holmes. Our whitepaper on startup fraud provides a thorough overview of the differences between successful startups and those that allow fraud to infect, metastasize, and persist within a company.

Image Source: Media from Wix

Fortunately, that's not every company. Startups catalyze economic growth in the form of preparing innovative technologies for commercialization and marketing. By leveraging short-term financial incentives (like grants, VC investment and other forms of funding) and long-term financial goals (like ringing the bell at NASDAQ), these companies take on large expenses and personal risks to bring technologies to market. Life science and medtech startups have the added constraints of long return horizons, brought on by the clinical burden of proof needed to satisfy complex regulatory constraints.

Building a business from nothing is never easy. There's too much to do and not enough resources to make it happen in ideal 'laboratory' conditions. Moreover, the people who join - your co-founders and employees - are gambling their livelihoods and reputations on your faith that an idea will work.

This is why leadership matters. Being able to establish a clear vision while cutting through the quagmire of conflicting challenges and responsibilities is a Herculean task. Being nice about it on a daily basis may seem aspirational at best.

That said, the best founders are never alone. They do not let themselves be alone. In addition to their co-founders and employees, they have a network of advisors to check their ideas, impulses, and iterations.

The best founders leverage experts to bring their idea to life | Image Source: Molecular Ideas

The question then becomes - with all of this faith in our idea, the market, and me, how can I bring out the best in these colleagues to help our business grow?

Another Leadership Style Article?

There are an abundance of resources on the internet about 'your leadership style' and what you can do to change it. The applicability of these other systems (some of which are backed by anecdotal evidence and others by years of academic research) can vary depending on the team you are being asked to lead, as well as the systems you have in place to monitor it.

Everything from 16 Personalities to the Harvard Business School 4 Leadership styles can help you provide insights into the type of leader you are (and want to be). Some speak to lofty goals and others have tangible personal steps to take to improve parts of your leadership style.

So, why is Molecular Ideas adding to the pile? There are two reasons.

I've found that it is difficult for founders and startup executives (myself included) to evaluate yourself constantly on more than a handful of fronts at once. The fast-paced environment of a startup is no excuse to be unprofessional; that said, the company cannot thrive if its executives do not have the mental RAM to see what is in front of them. This is why we're limiting ourselves to these two broad criteria around how you interact with teams: communication and autonomy. Further, many articles describe a given leadership style at the 30,000-foot level, but do not link the core attributes found in most startup leaders to their descriptions and fun titles. (Don't worry, I brought my own based on what I've seen in the field.)

Plus, startups are a bit different. Forgive me for stating the obvious, but when launching a startup, you are your own boss. Since it is up to you to build a team, you need to understand your own strengths and weaknesses to find those who can compliment or compensate for you. You create the systems - cultural, ethical, and technical - that define how you do business. That means your own leadership style is a reflection of how you view challenges, the people around you who can help with those challenges, and your perception of personal responsibility to solve things yourself.

Enter: Your Matrix

So, what are these criteria we're using to judge ourselves? We postulate that the two most important contributors to leadership style are communication and autonomy.

Since these are rather broad categories, we provide a little more detail below:

Communication: Defined here as your ability to balance clearly articulating a compelling vision or strategy with your ability to listen and solicit helpful ideas.

Here are the Communication sub-criteria in the matrix below:

a) Strategic Thinking - How well does the founder/executive navigate complexity and link disparate areas together to form an actionable plan in pursuit of a given goal?

b) Articulation - How clearly does the founder/executive communicate their ideas (verbally and in writing) to different audiences?

c) Active Listening - How often does the founder/executive ask for insight from colleagues and how well do they pause to consider the full statement and meaning of what they're saying?

Autonomy: Defined here as your ability to balance how much and what you choose to take on versus empower others to take on when faced with a challenge.

Here are the Autonomy sub-criteria in the matrix below:

a) Subject Matter Expertise - How well-versed is the founder/executive in the nuances of a given technical field (science, regulatory, financial, legal, etc.)?

b) Independence - How often does the founder/executive empower colleagues to handle programs, projects, and problems independently?

c) Decision Making - How well does the founder/executive make decisions in light of controversy or ambiguity?

Let's Meet Our Contestants

Before we go further, there is no one best style of leadership for a startup, nor is their one superior metric for startup success (though you might not want to mention that to your investors). The idea behind this is to figure out your style of leadership using these three distinct paradigms. All successful leaders should have these traits in abundance - which ones you possess over others is critical to understanding how you work with others and build a team. They Finally, all values here are are relative. Thus, they are meant to illustrate differences between these distinct styles rather than reflect objective statistics.

Style #1: The Commander

Overview: The Commander is closest to the stereotypical entrepreneur on this list. The distinction between this and the wheeling-and-dealing protagonists we see in popular media is their ability to listen. They take all the insight they feel is needed, then call the play. They lead from the front and aren't afraid to get their hands dirty (even if it's someone else's expertise). Their greatest strength is their ability to inspire and declare a bold plan - whether the waters are clear or murky. This helps them navigate complexity through authority, but can limit the autonomy of their colleagues. Commanders tend to learn best when they pair colleagues the leader trusts to check them and clear structure.

Style #2: The Jack-of-All-Trades

Overview: Your classic entrepreneur whose expertise is a mile wide and an inch deep. These leaders tend to focus on learning everything they can about a given field so that they can have informed discussions with their subject matter expert colleagues. This helps them be superb communicators and strategic thinkers given their passion for learning the language of many different areas. While they may have technical specialization in one field, the Jack-of-All-Trades balance the opinions of others before making decisions. However, this broad expertise can create crises of confidence when challenges in multiple, conflicting areas arise. Jacks-of-All-Trades learn best when empowered to make decisions after opinions are brought to the table.

Style #3: The Dungeon Master

As we've previously discussed, this style of startup leadership is rare, but exceptionally valuable. Dungeon Masters (also the narrative leader in world-famous storytelling & role-playing game, Dungeons & Dragons) in this context are patient leaders who specialize in maximizing individual team member autonomy. When confronted with a challenge, or in day-to-day operations, these leaders may appear 'hands-off'. In reality, they are trusting their colleagues to identify challenges rather than seeking them out. More often than not, they inform themselves by asking questions, moderating discussions, and opening the floor for solutions rather than charging ahead with their own ideas. Encountering this style is rare because it requires a team that is both skilled and trusting of each other. It's typically seen amongst more experienced entrepreneurs or those who have worked together before. While the fast-paced environment of startups does not allow for a business to be run by consensus, this leadership style lends itself well to acting based upon informed decisions.

Five Commonalities Across Successful Startup Leaders

What makes these leaders successful is not only the unique specialties of these styles, but also the commonalities in culture that they create.

1) They Understand Their Resources

Leaders recognize the unique value that every team member has to offer and tailors their requests to their abilities. Above all, they remember that VCs fund teams, not (only) ideas.

2) They Ask Questions of Everyone

While each of these three leadership styles differ in how they solicit and process information before coming t0 a conclusion, they all focus on ask questions of everyone. These can be regarding day-to-day status updates or being sure to solicit different perspectives when confronted with a significant organizational challenge.

3) There are No 'Second-Class Citizens'

All three of these leadership styles not only recognize and request insight from their colleagues, but ensure that decisions are made using objective criteria over bias. Some startup founders/executives who lack expertise in a given area tend to dismiss those who represent these schools of thought. As a result, the company culture gives rise to two types of colleagues - one whose opinions are not questions and one whose opinions are heavily discounted. This cascades into corporate decision making at every level of the startup, which can have dire consequences and even give rise to potentially fraudulent outcomes.

4) They are Able to Pivot Efficiently and Together

When challenges arise, these leaders solicit multiple opinions to ensure that viable options rise to the surface and are explored. While discussions take time (the most expensive resource in a startup), they are critical in assuring that team members understand the logic of a strategic direction. While they may not agree, it limits the potential risk of divergent, inefficient efforts from arising.

5) They are Able to Disagree and Still Move Forward

These three leadership styles encourage discourse, which can give rise to conflict. With that said, the individuals who gave rise to these distinct leadership styles all leveraged a combination of open discourse and leadership to guide open discussions. While not every discussion can end with consensus, they know how to help colleagues feel heard, satisfy competing interests, and limit 'behind the scenes' conflict.

Five Common Pitfalls for New Startup Leaders

These three leadership styles take time and practice to cultivate. New startup leaders often struggle with at least one of these five challenges while attempting to cultivate their teams.

1) Failure to Set Common Expectations

One of the most significant challenges for new startups (and in particular, new startup leaders) is the failure to set common expectations. This extends through everything from working hours to personal monetary contributions to the company to choices of strategic importance. This does not necessarily mean 'laying down the law' when you're hiring a new colleague or vetting a co-founder. Rather, it means systematically evaluating how current and future challenges impact the person across the table.

2) Selectively Leveraging Perspectives (Creating Second-Class Citizens)

Failing to acknowledge others comes in many forms. It could take the form of not praising someone's hard work, failing to recognize the personal sacrifice(s) they made to make that output happen, and/or not appropriately leveraging their perspectives.

There is no doubt that there needs to be one person responsible for making decisions in a fast-paced, high-risk startup world. Decentralizing decision-making can be dangerous without trust and common principles to bind disparate efforts together. That said, selectively soliciting opinions is the ultimate 'turn-off' for even the most zealous employee. The moment people feel as though they are not contributing value is the moment they stop contributing.

3) Siloed Teams

Transparency is the connective tissue by which a startup functions. While subject matter experts should be left to cook in their own kitchens, understanding how their dish fits in the scheme of the overall 'meal' (startup strategy) is fundamental to success. No challenge is entirely isolated from other domains of technical, legal, or strategic expertise.

4) Well-Intentioned Dishonesty

As strange as it sounds, the reality is that many new startup executives (mostly when they're pre-incorporation) make promises to stakeholders that they may not be able to keep. For the most part, these are commitments to have access to certain resources or re-evaluate equity positions after a given amount of time. They may also take the form of tangible or intangible benefits that activate 'when we hit our next milestone in around six months.' As we've said before, there are no facts about the future. When plans are delayed, it becomes unclear as to who is entitled to what. This gives rise to conflict, confusion, and cynicism amongst colleagues. Solving for this involves planning ahead for multiple contingencies and strong negotiating on both sides.

5) Misalignment to Goals

All of these challenges speak to the same underlying outcome - misalignment to goals. When people start working disparately or even actively against each other, it does not matter if your idea's market value is a billion dollars. Depending on the tone and tenor of the conversation, it can be helpful to step back and redefine outcomes after understanding individual's challenges.

Identifying Your Leadership Style

Hopefully, this piece has been helpful for you as a reflective exercise into the startup leader that you are (and can be). To some extent, the demands of a startup demand that your style adapts to the needs of the moment. Hopefully can use this to figure out your tendencies and the strengths and weaknesses that come with it.

Once again, there are many different resources on the internet. My advice is to read as much as possible, request feedback often, and leverage your advisors to gain objectivity and insight into situations.

Bonus: Leadership Matrix PowerPoint (Download)

Before we go. we've included a PowerPoint template below that you can use to gauge yourself, along with the definitions from above and some questions for self-reflection.

Molecular Ideas - Leadership Style Matrix (Jan 2022)
Download PPTX • 140KB

Lead on.

That’s all for today! Thanks for spending your time with us. Please share this article, and sign up to leave your thoughts, ideas, and opinions in the comments. Your feedback is always welcome and helps Molecular Ideas grow!

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