Embarking on a startup journey is like venturing into a wild jungle. As your startup evolves from Series B funding, the terrain becomes even more challenging, demanding leadership that can grow and adapt. This blog reveals relevant tools that set successful startup executives apart: 5 soft skills that transform ordinary leaders into dynamic trailblazers.

Imagine your startup as a mighty tree, growing rapidly as funding pours in. The branches stretch, the roots deepen, and the culture must thrive amidst growth. How? The answer lies in soft skills: discipline, time management, communication, optimism, and emotional intelligence. These skills become your survival kit, equipping you to lead your startup through the uncharted wilderness of the current macroeconomic climate, no matter the terrain ahead.

The art of managing emotions as a leader

The startup trajectory is one marked with challenges that can provoke a range of emotions on the path to success. Some of the common feelings startup executives encounter on their journey include hunger, loneliness, and exhaustion.

Emotions often mark the course, and managing them for the benefit of everyone in the startup is best done using soft skills. Developing strong soft skills can help you create a more effective, harmonious, and productive work environment, as well as increase your own job satisfaction and happiness. 

Soft skills are the personal qualities that enable you to work well with others and achieve your goals. They are essential for leaders in any work setting, but especially for those in startups. Each soft skill emerges as your tool to confront the unique challenges of startup leadership.

The startup landscape isn’t just about trouble; it’s also marked by excitement, happiness, and accomplishment. Passion-driven pursuits, milestone triumphs, and the exhilaration of thriving under pressure shape your leadership journey. By harnessing these positive emotions, you can fuel your startup’s momentum toward success.

Prepping your toolkit: 5 must-have soft skills for leaders

Startups usually introduce innovative ways to solve problems by creating a unique value proposition for their consumers. While innovating, every step taken can be a venture into the unknown. Something as adventurous, and even as risky, as being a startup leader, requires having a toolkit of soft skills ready for you to deploy.

While every startup is unique, there are leaders – lots of them – who’ve walked the startup path before you. The insights of startup executives or mentors who’ve mastered soft skills can help you chart your course. These skills become your superpowers, guiding your leadership through uncertain terrain. Discipline, as revealed by Paul Graham, propels executives through challenges, while time management, championed by Vijaye Raji, empowers efficient navigation. Emotional intelligence, communication, and optimism, as shown by Fineas Tatar, Adnan Khan, and Daniel Gilbert respectively, make a well-rounded leader.

1. Discipline

Imagine the startup jungle with dense vegetation, where every step is a challenge. It’s here that the soft skill of discipline comes into play. Paul Graham, the co-founder of Y Combinator, describes discipline as forging ahead despite the desire to retreat. Discipline, he explains, is what keeps leaders moving forward even in the face of adversity. Like seasoned explorers, startup executives cultivate this skill, setting clear goals and breaking them down into manageable steps. Discipline makes the difference between being lost and finding your way.

How do you handle difficult or unpleasant tasks? Do you procrastinate or avoid them, or do you tackle them head-on and finish them as soon as possible? Do you give up easily when things get tough or when you face obstacles, or do you persist and find ways to overcome them?

2. Time management

The startup jungle demands focusing and triaging your priorities. Time management ensures that every move is purposeful. To this end, Vijaye Raji, Statsig’s CEO, urges startup leaders to rely on tools and strategies. Raji suggests using calendars to track priorities, delegating tasks such as assigning roles, and avoiding distractions like prowling predators. It’s a survival technique that transforms chaos into rhythm.

Are you setting clear goals, carving pathways through the undergrowth of tasks? Are you allocating your resources wisely, or are you lost in the tangle? We recommend our blog post about calendar compartmentalization and how this strategic technique can help you navigate the wildest calendars.

3. Communication

Communication is your signal fire in the heart of this jungle, guiding others through the thick vegetation of ideas. Adnan Khan, co-founder of Viva, reveals that communication is the soft skill that every startup leader needs. And communication is more than just crafting messages; it’s about active listening, feedback, and adaptability. 

Startup leaders, are you stoking meaningful conversations, or are your words fading into the night? How do you express yourself and exchange information with others? Do you speak or write clearly, concisely, and coherently, or do you ramble, confuse, or bore them? Do you listen actively, ask relevant questions, and give constructive feedback, or do you interrupt, talk over, or ignore them? 

4. Optimism

In Latin American culture, a machete is an all-purpose tool that helps you navigate challenges in life, especially in the jungle. As a startup executive, the soft skill of optimism becomes your machete, cutting through the thickest of challenges. Harvard professor and author Daniel Gilbert shows us that optimism isn’t just a mindset; it’s a tool that cuts a route through adversity, fostering resilience and driving innovation.

Do you see opportunities rather than problems, or do you focus on limitations instead of possibilities? Do you boost motivation, creativity, resilience, and happiness in your team, or do you lower collective morale, drive, confidence, and satisfaction?

5. Emotional intelligence

In the heart of the startup jungle, where emotions roam like untamed beasts, Fineas Tatar, co-founder of Viva, introduces us to the emotional intelligence quotient (EQ), a compass guiding us through the chaos. EQ is what helps leaders step into others’ shoes, revealing an unseen path. EQ leads us to understand others better, fostering trust. Tatar explains that EQ isn’t just walking in others’ shoes, though; it’s the foundation for thriving in the toughest startup challenges, leading teams, and helping customers find solutions in this wild business jungle.

How do you relate to others’ emotions? Do you recognize and understand how they feel, or do you ignore or dismiss them? Do you show compassion and support, or do you criticize or judge them? Do you adjust your communication and behavior according to their emotional state, or do you treat them the same regardless of how they feel?

Leadership soft skills gone wrong: WeWork

How are soft skills relevant to WeWork’s tale? 

WeWork—a co-working space giant once valued at $47 billion, is now a cautionary tale. Its fall in 2019, triggered by a failed IPO attempt, was a spectacle of leadership gone wrong. It has become the center of attention once again in 2023, as news outlets expressed a “substantial doubt” that WeWork will be able to stay in business. 

Blame for the IPO fail fell on founder and former CEO, Adam Neumann, whose leadership style portrayed the image of a visionary yet unrealistic explorer. Neumann’s approach was one that navigated dangerous paths, leading to mismanagement, self-dealing, and erratic behavior. 

His company ventured off-course, slipping into the darkness of what has been called a toxic, cult-like work culture where the wild revelry of excessive drinking, partying, and harassment reigned.

The perils of miscommunication

A soft skill that Neumann failed to demonstrate was communication, the skill of conveying information and ideas effectively and efficiently. Communication is vital for startup executives, who have to interact with various audiences and stakeholders in different situations and contexts. Neumann’s communication, however, was often misleading, inconsistent, and inappropriate. 

He made false or exaggerated claims about his company’s performance, vision, and mission. Also communicated poorly with his team and investors, often changing plans or expectations without explanation or consultation. 

Neumman has been said to communicate through alcohol-based relationships, such as serving shots of tequila during job interviews or hosting alcohol-fueled events that resulted in harassment.

Little to no EQ

As colleagues and coworkers have stated, Neumann lacked EQ, or emotional intelligence, the ability to understand and manage your own emotions and those of others. EQ is especially important for startup leaders, as they have to deal with heavy stress and a range of intense feelings, both their own and those of team members. 

However, Neumann’s EQ was low, as he showed little EQ or compassion for his employees or customers. After laying off 7% of WeWork’s employees because they needed to cut costs, he hired the artist Darryl McDaniels of hip-hop group Run-DMC to play a set while Neumann drank tequila. 

He also showed little self-awareness or self-regulation of his emotions, often acting impulsively or irrationally, as can be seen in the WeCrashed TV series. 

Self-assessment: How do you know if your leadership soft skills are good enough?

No startup executive wants to become the next cautionary tale. To reach their goals and grow their companies, startup executives need to understand their strongest and weakest soft skills. Working intentionally and continuously in these areas will help you become a stronger leader. 

We created this assessment to help you evaluate your own leadership soft skills and discover areas you need to master. This guide can help you understand your strengths and weaknesses as a startup leader. We recommend you bookmark this and evaluate yourself throughout the week in your 1:1s, board meetings, team meetings, and even customer calls. 

The following questions are open-ended, meaning they require more than a yes or no answer, and are designed to help you reflect on your skills and behaviors to identify areas for improvement. There might be nuances to each question and answer; you might not even have the same answer for every stakeholder or situation. Leaders may react differently with investors than they would with subordinates. 

We strongly recommend you respond authentically, as these soft skills can make or break your leadership – and your business.

Discipline:

• Do you have a strategy to stay motivated and focused when doing repetitive or mundane tasks that are crucial for your startup’s progress?
• Do you have an effective accountability system set in place to make sure you are staying disciplined? 
• Do you intentionally set time aside for deep, focused work so you can tackle your priorities? Do you prioritize this time or do you continuously defer it?

Time management:

• Do you have a strategy to handle your calendar appointments?
• How do you cope with unforeseen time demands or urgent tasks? Do you find a way to also go through important tasks that aren’t urgent?
• Have you been delegating tasks to appropriate team members so you can focus on what matters most to the growth of your company?

Communication:

• When delegating tasks for the next board meeting, do you clearly explain the desired outcome so your team knows exactly what you need from them? Are you available to answer their questions?
• Do you listen to your colleagues or direct reports and seriously consider their ideas and suggestions even if they’re not the same as your own?
• Are you familiar with the concept of active listening?

Optimism:

• Do you have a strategy to deal with rejection from investors, customers, and recruits and keep morale up despite this?
• Do you believe that optimism is important in doing business and keeping strong business relationships? If so, how is this reflected in your decision-making?
• How often do you verbally appreciate the strengths and talents of your direct reports? Do you only let them know when you’ve noticed their weaknesses and flaws?

Emotional intelligence:

• Do you manage your emotions during high-pressure situations to prevent them from negatively impacting your decision-making as a startup executive?
• If you asked your team, would they say they feel understood in their emotions? Why or why not?
• How did you react the last time a team member made a mistake? Was your reaction compassionate or did you criticize and judge them? What can you do differently next time?

You can also ask a team member or colleague to answer these statements for you, to get an external perspective on your leadership soft skills.

By embracing the power of soft skills, you transcend the ordinary, emerging as a visionary leader. Learn how to be disciplined, a great time manager, an effective communicator, an optimist, and emotionally intelligent. Handle the startup jungle with skill, turning problems into wins, and becoming a strong leader in a world that loves growth and innovation. This is where your leadership journey starts. 

Dive into our leadership section for more knowledge and insights on what it means to be a world-class leader in startups today.

We also recommend finding mentors, advisors, and colleagues with experience in these matters so they can provide counsel.