On Leadership at Tech Startups

Qualifier: My experiences and perspectives are probably heavily influenced by a narrow view I have into the world involving mostly tech startups and knowledge workforces, coupled with my personal experiences. I am not the most well-educated in leadership and coaching theory, so my language is likely flawed at times, but I hope I get some sentiments across as intended. As with almost everything I’m interested in, I treat learning about leadership academically.

First, here are some books and resources I’ve digested that have influenced my perspectives. I will be updating this list as I continue to learn and grow.

1. Hit Refresh by Satya Nadella: Satya’s strategy to reinventing Microsoft by developing a culture that energizes the workforce by leading with empathy.
2. Crossing the Chasm by Geoffrey A. Moore: Might seem odd for this high-tech product marketing book to be on this list, but there are some really good points about strong leadership through clear communication and well-defined strategy, and spreading positivity and empowering employees.
3. Simon Sinek.
4. The Culture Map by Erin Meyer: Fantastic resource to understanding communication and perspectives different people hold that might be a result of their culture. I use this to avoid harboring the discomfort and instead acknowledge it and try and adapt my communication style.
5. Sapiens by Yuval Noah Harari: It might seem odd for this book to be on this list, but understanding the history of cooperation in societies and how leadership styles have evolved as societies have evolved has been eye-opening.

I’ve worked at two technology startups now and have heard from colleagues and friends who have shared experiences working at others; there have been some really great learnings for me from these experiences but I want to try and articulate what I see as common leadership missteps.

Leading from the head rather than the heart

When you lead from the head, communication tends to come across as impersonal, uncaring and untrustworthy. When you communicate from the heart, I want to go into battle for you. Satya’s story in Hit Refresh is a great example of this, where he is asked what he would first do if he saw a crying baby alone on a street. The head says to call 911, but the heart says to just pick up the baby. I don’t believe there’s a magic formula to think from the heart, and I’ve seen leaders under stress think from the head with higher frequency. I am working on catching myself in leadership moments where I think from the head and consciously taking a minute to switch. In moments where I am alone and working with things as opposed to people, I let my head have at it.

Business viewed as a zero-sum game

Most often, one company does not have to fail for another to succeed. In addition, sure it’s great to celebrate your achievements, but there’s no need to put down others’ work to make yours look better - doing so spreads negativity in the work environment. Satya mentions something in Hit Refresh (section about building partnerships) that speaks to this as well, where Microsoft had to learn to cooperate with Amazon in areas where they weren’t direct competitors to maximize mutual success and increase the size of the market. Tesla’s open sourcing of patents or Volvo’s decision let all manufacturers use the 3-point seat belt patent for free are great examples to remind us that at the end of the day, the faster we solve the world’s problems with technology, the better of all of society will be. Regardless of who did it.

No clear vision/purpose and no effort to build a specific culture

To be clear, this is answering the question “Why do you do what you do?” - Simon Sinek at TED. The bizarre part about this is that tech startups seem to claim one of two rationalizations for this deliberate decision: to not have enough time for it unlike bigger companies, or fear of the “commitment” this might imply when they must be willing to be flexible and agile as a small company. Let’s break that down. With regards to the amount of time needed, yes, it is a time consuming exercise to define a vision, values and ideal culture and communicate it all effectively. However, startups are the places that need this the most - employees are often overworked, underpaid and underappreciated under the constraints of delivering with a limited runway. One could argue that a purpose to rally around is crucial in propagating positive energy in exactly this kind of environment. The commitment argument is a misunderstanding of what these are - neither one’s purpose for existing nor the types of behavior one want to encourage of the workforce are likely to change. The only thing I can see possibly changing drastically is a mission statement, and so what if it does?

Inversed prioritization of stakeholders

I think something we forget all too easily is that society is every company’s biggest stakeholder. That might not seem obvious right away, but sitting with this for a moment should reveal that any company could not even exist without the cooperation of society (see Sapiens by Yuval Noah Harari). I’ve seen numerous examples of companies treating employees much better than applying candidates or former employees, and often this comes down to a power dynamic. Some examples of this are poorly run interview processes (not respecting candidates’ time, rescinding offers without justification, automated rejection emails after interviews with multiple people, ghosting) and poor termination practices (terminating employment earlier than notice period, not giving a proper send-off, constructive dismissal to avoid paying severance). I am convinced that the order of priority in stakeholders, and thus the care taken while communicating, should be (1) general public, including former employees and candidates (2) current employees (3) clients/customers and (4) investors/board. Unfortunately, this is reversed way too often, not acknowledged, and rationalized with claims of “best for the business”. The reason for the proposed ordering is that investors, clients and employees who know you best and are with you for the long haul, know you, trust you, and communicating effectively becomes easier the better you know someone. The reason many companies which have strong social missions do very well is for this reason, they understand everyday that they exist primarily to serve society, and they develop a long-term thinking mindset. I recognize that this section is probably the worst articulated, since it touches on several pieces; the best reference I’ve found to resonate with what I’m trying to communicate is Simon Sinek’s take on having the “Courage To Lead”.