Accidental Entrepreneur: 8 Basics for Beating Mid-Career Blues and Thrive at Work

  1. Be a Driver: Don’t wait for upper management to drive you, rather you become the driver of the projects and place your team members in a position to be successful. Work with marketing and understand the customer request, work with the architects to understand the architecture and then work with the delivery or manufacturing people to understand what it means by delivering the product. It is you who owns the delivery, be a driver.
  2. Learn the Business: Many people just focus on their own deliverables and don’t spend time understanding the business. By business what I mean is that they forget the end product and spend time just focusing on the narrow area they work in. This can be very detrimental to the team and yourself by not understanding the business. At the end of the day, business pays for the bill. Learning the business helps make decisions which are right for the business rather than just the team.
  3. Know the pros and cons of decisions: Every decision one makes during the project has positive and negative impact on the project and company. Understanding those and articulating that to the team members and/or upper management, helps one make decisions with data. I love Excel sheets with pros and cons written down for easy understanding and for us to revisit, in case we made the wrong decision.
  4. Keep up with Technology: Mainly in larger companies, once a person becomes a middle manager, they become the process masters or paper pushers without learning the technology trends. This can be a disaster for people who want to move up in the ladder or someone else younger who is attuned with the market and technology. Without keeping up with the technology trend, basically you are digging your own grave and you become very easily redundant in the organization.
  5. Build Good Rapport: Building relationships with the executive management team as well as the key team members is part of the role of the job. Everyone goes through some challenges and it is important to have good allies who can help during that time. By building a good rapport with the key decision makers and contributors, you will be able overcome unexpected challenges. Spend time building your network!
  6. Customer Knowledge: There are two aspects to customer knowledge. First one is the customer market and solutions which they are expecting from your company and the second one is the key people such as technical architects (Technology buyers), purchasers (Economical buyers) and executives (Decision Makers). When there are issues with product execution, these relationships will help navigate through the challenges by providing priorities.
  7. Detail Planning and Macro level focus: Normally middle managers get into detail of the execution/project planning, they forget to step back and understand the current overall progress or lack thereof until it is too late. I tend to take time every few weeks to evaluate the project progress and sit down with relevant parties to analyze the impacts. This is very important for timely execution and highlighting any major misses early.
  8. Continue to Sell Yourself: Being in the middle management is very tough from stress, since you are representing the commitment of others, and amount of work to coordinate all the activities. Most of the time, you are the bearer of the bad news to the upper management and you get to talk to them during those challenging times only. It is important to sell yourself during the good times too. I try to meet with executive management in regular cadence and report the progress as well as continue to send weekly reports with both accomplishments and challenges. No one but you is there to sell you.



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Ruban Kanapathippillai

Ruban Kanapathippillai

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