Friday, August 19, 2022

Evaluating a Company to Join, Culture: Senior Leadership

Choosing a company to join can be a worthy challenge.  Fortunately for all of us, Wendy Zhao has kindly agreed to collaborate on this next part!  Welcome Wendy!

While the Culture of a company may be codified in its mission and values, it is expressed through its people.  The people in a company obviously literally make up the company and two groups have an outsized impact on the experience of the culture: Senior Leadership & Your Manager. With this piece we are going to share how to evaluate Senior Leadership.

Senior leadership, the people with the Cs in front of their title, are directly responsible for the culture of an organization. These individuals set the rules for the company, hire / promote / fire, decide how the organizational structure evolves, determine compensation, and communicate the stories that carry the company’s culture and identity to employees, customers & investors. All sins of a company are sins of senior leadership, so it is worth understanding who you are signing up to work for. 

In the dynamic & ever changing environment like a startup, here are a few critical cultural components to look for in a leadership team:


The most important trait of a leadership team is cohesiveness.  With Cohesiveness, the company can flouris; without it, the rest of the company will be locked in a forever war of working long, frustrating hours with little getting done. By contrast, a leadership team that works well together and is aligned on the company’s mission will allow complex, integrated work to proceed smoothly.  They will be able to engage in healthy conflict to arrive at mutual commitment, hold the company accountable and ultimately deliver results. This is perhaps the best internal predictor of forward progress.


Startups are, by definition, trying to do something new while working with limited resources. They should be constantly forming hypotheses, testing ideas, evaluating feedback, learning the right lessons: iterating their way to understanding their customer, business & product.  You want a leadership team with the level of grit and resourcefulness to find the cheapest AND quickest way of doing something without compromising quality. Instead of hiring a costly consultant, ask a friend-of a friend-of a friend with subject matter expertise for a favor.  This way of getting things done is crucial in the early days and the spirit should never quite leave; however, it may be a shock if you are used to a more formal, process driven environment.  Your interview process is a good indicator here, how did it feel in terms of speed vs. polish/formality.  If you liked the speed, good. If you were put off by the lack of polish, you might have trouble once you work there.

Emotional intelligence

A CEO with strong EQ will surround themselves with a similar leadership team to create a superior culture in which individuals thrive, grow and develop while solving the aforementioned complex/impossible-seeming problems. Brilliant jerks exist, but are neither necessary nor sufficient for success as so much of what we do to build businesses is based on empathetic human-to-human relationships. A leader who lacks self awareness, cannot read the room, adjust tone or messaging based on who he/she is talking to, understand how his/her actions affect others, or how to recognize & manage emotions will typically not succeed in the long run and make everyone’s life miserable in the process.  


Look for leaders who have presence, who are intrinsically motivated by the mission and in turn exude a special kind of energy that is able to motivate others. As an employee, you’re generally being asked to sacrifice today for greater upside later while working long hours for many years to get there. Leadership teams who can make you feel the mission in your very being & continuously reinforce it are the ones to stay with.

Other qualities like prior experience and track record, subject matter expertise, and personal network, are important and can be instrumental in the success of the business, but not necessarily the culture within the organization.

While it may be impossible to vet all of this during an interview process, notice signs that indicate what the startup’s culture, mission alignment, and people are like - Do you interview with the senior leadership team? Do they address your questions and respect your diligence? Are they attentive and do you feel positive energy during the interview? Is there a thoughtful interview process in place? Can they explain what success looks like for your role? 

Once you’ve determined a senior leadership team you can trust, there is an even more important person you need to evaluate, your manager.  Next time!

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