Leadership Skills

4 Reasons Why Founders Should Experience Different Roles in Their Company

4 Reasons Why Founders Should Experience Different Roles in Their Company
Image credit: Bernie Zimmermann | Flickr
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Rotating through leadership roles within your company can be a challenging experience, especially because it’s often forced upon you. But experiencing different roles is practical, too: If you’re building a company, at various points you’ll either be the first to fill a role or temporarily have to take over a department.

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Since we started InsightSquared in 2011, I’ve served as head of sales and head of customer service, and currently I'm the acting head of marketing. Some things I did right, and some things I could have done better, but I’ve become a better CEO and leader as a result. Here are four reasons why I think all founders should embrace the unexpected (but fairly inevitable) challenge of management rotation:

1. You'll establish a common language.

My cofounder, Bryan Stevenson, once told me that, “The most frequent cause of failure in software projects is the miscommunication of requirements between the business customer and the software developer.” By extension, a big challenge for tech companies is communication between the business and tech sides. It can be tricky to convey "the why" and "the what" you want to build, as people from different disciplines tend to speak very different languages.

I remember cobbling together a prototype of the product I hoped to form our company around (full disclosure: I am not a trained software engineer). That original prototype was a very, very distant cousin to the product we sell today, but by building it myself (i.e., painfully taking months to do what a more skilled person could have done in days), I was able to quickly establish a common language with Bryan. My prototype saved him from the risky and time-consuming process of extracting specifications and let him focus instead on launching our product.

2. You'll have more empathy.

I was head of customer service at our company. By that, I mean I was our first customer service rep. I handled customer onboarding and answered late-night questions. Hearing from customers directly on a daily basis, I gained a better understanding of the problems they wanted to solve. I also learned first-hand that customer service is a hard job, with multiple objectives: creating customer happiness, funneling feedback to product and engineering teams and working with sales to make sure you’re bringing on the right customers.

It’s easy to judge people from afar and wonder, “Why aren’t they doing their jobs better?” But when you’re thrust into a role and it’s suddenly your responsibility, you have no choice but to learn and understand the challenges, and you become more empathetic as a result.

Related: Growing Your Business: Strategic Leadership Skills for the Long Game

3. You'll be a better peer and manager. 

One of the challenges of being both a member and manager of the executive team is being a generalist among specialists. The lack of subject-matter expertise makes it more difficult to provide feedback, act as a peer and challenge experienced leaders.

I was once our company’s head of sales, both as the first sales rep, and later as leader of the team. Due to that past experience, I am a better thought partner to Steve McKenzie, our vice president of sales. I’m also able to challenge Steve in a way that wouldn’t have been possible had I not earned my stripes.

By rotating through various leadership roles and learning the nuts and bolts behind each position, you learn how to provide better service to the other leaders in your company and develop mutually supportive relationships.

4. You'll learn how to problem-solve.

Rotating through various roles in your company is hard, and you’re not going to be perfect at it. But the upside is that you’ll get really good at breaking down problems.

As I moved around different roles, I was reminded that problem-solving is a universal need. I realized I could use the same problem-solving tool kit I had already used to fund-raise or repair my motorcycle, then apply that to figuring out my head of marketing position. The reason? Problem-solving is really just about dissecting the issue in question into its smallest possible components, understanding the mechanics and challenging the assumptions. Taking an analytical approach has allowed me to be more successful in each new role, and even allows me to transfer lessons from one discipline to another.

At the end of the day, I think it comes down to this: if you’re not a seasoned CEO, you should probably do a job before you hire someone else to do it. You’ll stand a better chance of hiring the right person and you’ll become a better peer and manager. Ben Horowitz put it well in his book, The Hard Thing About Hard Things: “There are no shortcuts to knowledge, especially knowledge gained from personal experience. Following conventional wisdom and relying on shortcuts can be worse than knowing nothing at all.”

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