Startup Success Depends On Your Leadership Skills

Being a leader doesn’t come with a how-to guide, but a couple of key tactics can go a long way.

Photo: AJ Shankar is the founder and CEO of legal tech startup Everlaw; Source: Courtesy Photo
Photo: AJ Shankar, founder and CEO of legal tech startup Everlaw; Source: Courtesy Photo

A business often starts when one person sees something that can be done better. They think to themselves: “It seems silly that there’s no roller skating rink in town” or “Why is there no efficient way for lawyers to review documents?”

Then you find yourself creating a company to do exactly that – to bring whatever expertise you have to the table and solve a perceived problem. The challenge comes when you realize that your company’s success is largely dependent not on your sales skills, accounting prowess, or programming aptitude, but on your leadership skills.

The hardest part of running a business is being a leader.

At a large company, leadership precipitates from the explicit personnel hierarchy. You know exactly whom you’re supposed to manage and their responsibilities. At a startup, that leadership role is much more nuanced. The setting is more intimate: people are as much friends as they are co-workers, so strict power lines feel uncomfortable. Moreover, each employee wears many hats; there is often no clear delineation of roles.

Small teams grow fluidly. If there is a hierarchy, you’re making it up as you go; there is no massive org chart to fill out. Since this hierarchy is not explicit, leadership roles feel more arbitrary.

These nuances make startups fun—and a much better fit for many than a rigid work environment. However, they also require extra attention. So, how can you approach these challenges?

Here are five tactics that I use to be a more effective leader:


  1. Gather employee feedback.

    I use tools like 3sixty and 15five so employees can easily share suggestions and struggles, both identifiable and anonymously. These tools help improve team morale and expose many wonderful suggestions for how to improve the business. It is especially helpful in giving everyone an equal say, regardless of their seniority or gender.

  2. Have one-on-one meetings.

    I meet with one team member a day, cycling through the entire company every few weeks, with an open-door policy so anyone can request a one-on-one at any time. These free-wheeling conversations give me insight into individual issues and help me develop a stronger relationship with each person. This is a luxury you can only have at a small company, so don’t forget to take advantage of it!

  3. Create a culture of transparency.

    Our business and development teams participate in each others roadmap meetings, so everyone can be part of setting the direction for each group. All planning documents and meeting notes are shared company-wide, and team meetings are open-door.

    Transparency removes the capriciousness from high-level decisions by exposing underlying factors that went into making them. It also helps team members become more thoughtful about topics outside their own domain.

    For example, a salesperson can learn more of a particular feature’s capabilities by chatting with the developer who created it, which can help her sell it more convincingly the next time she does a demo.

  4. Don’t pull rank.

    If I’m making a tough decision, I argue its facets, but I try to subject my arguments to the same level of scrutiny as I would anyone else’s. I rely on my team members to point out flaws and help me arrive at the best decision. I’ve changed my mind on many big issues as a result, always with better outcomes.

    The best idea—not office politics—wins. Everyone on the team knows that their voice matters. This kind of policy doesn’t scale well to large companies, so take advantage of it while you’re small!

  5. Be humble.

    The best leaders can admit they’re wrong, and the best leadership is by example. This is an easy one for many founders: as their company’s first employees, they’ve taken out the trash and assembled furniture. Just keep that ethos alive and those hands dirty!

Being a leader doesn’t come with a how-to guide, but a couple of key tactics can go a long way. Try these five ideas for being a stronger leader to your team, and let me know how it goes!


This article has been edited and condensed.

AJ Shankar is the founder and CEO of legal tech startup Everlaw, where he is building the world’s most advanced litigation platform. Everlaw serves 8 of the top 10 class action law firms and was named an ediscovery “Vendor to Watch” by Gartner. AJ has a Ph.D. in Computer Science from UC Berkeley and an A.B. in Applied Mathematics and Computer Science from Harvard University. Connect with @ajshankar and with @everlaw on Twitter.


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