Accidental Entrepreneur: 15 steps to reach the C-level in your career journey

  1. Articulating Vision Vs Mission: Great leaders have a way of describing the Vision of the company clearly and connect all the activities + projects which come under the mission to connect to the vision. For example, the good leaders whom I have worked with would take any of the tactical questions and respond with the vision of the company along with why it is important for the short term as well as long terms.
  2. Build Strong Diverse Leadership Team: I discussed many times the importance of a diverse team from experiences and backgrounds. This is mainly important for the leadership team. Diverse team can help a leader get through unforeseen issues and new issues with their experiences. Some Silicon Valley companies fail due to only having people with very similar backgrounds and thinking processes.
  3. Simple but Effective Management Techniques: As a person grows and goes up the management chain, he or she learns what works and what doesn’t work. It’s important to learn from them and start building a list of actions/processes which can motivate people to get the best results out of the extended team. One of my CEOs had a simple slide with a ladder chart articulating the importance of each function in the company/team and articulating which steps are we at each company. That gave us a clear and concise message to the management team.
  4. Fairness in Every decision made: Leaders are tasked with important and difficult decisions to make the company successful. Good leaders have clear ideas of the needs of the company and when they have to make decisions, they execute with fairness and clarity. Any appearance of nepotism and privilege would kill the morale of the team which in turn would make the company dysfunctional. Be fair and able to justify those decisions in simple terms rather than with detailed nuance explanations.
  5. Don’t get Bogged down with Details: Learning to understand the most important aspect of the project and company while others in the team focus on the details help a leader sail the ship through hardships and unexpected events. Practicing this in early career by identifying what is key and what needs my attention would help build up the leadership mentality.
  6. Learn to Delegate: Delegation is very difficult for junior leaders and perfectionists who think they can do everything by themselves. I tell two points to executives that not being delegate means you have hired the wrong person to drive and solve the problem and not delegating will not help scale the company. Both trust and scale are key for success of the company and success of the leader.
  7. Strong Multi-functional Knowledge: As a person moves up the ladder, they are expected to understand and make decisions in financial, customer, product and people areas. I used to attend various management classes in all of these areas to learn and convey my messages in impactful ways. Good leaders can articulate all of these areas at a high level and make good decisions.
  8. Ask for data for Complaints and Complements: There would be people in passing who would complain about others in the team or you may hear compliments about someone. I used to react immediately and call on the person without understanding the situation. Later, I learned from a good leader to ask two questions, first for detailed information on the complaint and second one is whether they have discussed the item directly with the person whom they are talking about. By asking these two questions and making people think through the answers normally discourage people from complaining without data and trying to put others down. I have seen these remove team frictions, productivity and morale.
  9. Build Customer Knowledge and Relationship: The difference between a good leader and great leader is building customer relationships. It’s easy to have ideas, moderately difficult to build a product, but convincing some customers to buy the product is the toughest of all. Bringing customer knowledge to the table while discussing the projects from customer point of view for different use cases and markets differentiate an effective leader.
  10. Connect with Industry experts and influencers: Many managers who come up from a technology background, including me, think that we can solve the problem ourselves or by working within the team. By reaching out to industry experts and influencers, one would get a completely different perspective about what others are doing in the competitive landscape. These people can be your advocate for finding a leadership job somewhere else, in case you hit a wall/ceiling at your current company.
  1. Have Advocates Know Your Strength: End of the day it’s all about selling your potential and capabilities. Many modest people have issues selling themselves and “bragging” about their accomplishments. In addition to building continued trust with the current management chain, it is good to have people who would advocate for you with solid data and conviction. Spend time cultivating advocates who believe in you.
  2. Look Beyond Your Own Responsibilities: For company success, many things have to go right. Hiring the right resources to execute on the main areas and supporting them with additional information such as finance, marketing and legal areas would help reduce the burden on those managers and you bring value to the company. Learn to connect with people with backgrounds in various areas and articulate it to the team.
  3. Willingness to Volunteer for New Opportunities/Task: Some people complain that I am not selected for a special project or given a chance to prove their capabilities. From what I have seen is that everyone is there for themselves and when one puts himself or herself out there to help others and alleviate their stress, others will start to notice you. This worked for me many times and that is how I got to be cofounders of those companies by others noticing my willingness to step up and help when help is needed without being asked.
  4. Don’t Create Permanent Foes: It is easier to look at someone’s actions and think that the person is doing it for malicious reasons or purpose. I tend to first put myself in their shoes and find logical, not emotional, reasons for the action. In case I find out the action was taken for the wrong reason, I would argue and fight to change. Once I pass that situation, I tend to forget and forgive by not creating permanent negative opinions. This is key when you need help in the future as well as for the health of the overall relationship.
  5. Getting MBA vs Practical Experiences: This is a hot topic among up and coming managers and leaders. I have a strong opinion that practical in-field experience is a lot more important than getting another degree. I learned all my management, interpersonal and team building talents by doing those while learning + adjusting.. My recommendation to people is to supplement those experiences with very specific courses which would provide additional tools and processes to implement on the job. MBA alone itself is not going to help you move up the ladder.



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Ruban Kanapathippillai

Ruban Kanapathippillai

Entrepreneur, Founder of multiple successful startups, Mentor/coach, Angel investor (Sandhill Angels) and Positive thinker