When I look back at the first three years of bootstrapping our startup NerdWallet, the lesson I wish I had figured out earlier is you can’t read your way out of a problem.
When we first launched our company and needed advice, our tendency was to grab a book and go off in the corner to figure out how to scale our operations, hire amazing talent or motivate employees, among other queries. While these books did provide great insight, we soon learned a half-hour conversation with an expert of mentor provided invaluable leadership information we couldn’t get in a book. Not only did this person offer firsthand experience and great words of wisdom but they also provided a connection.
Here are leadership lessons for entrepreneurs that we wish we would have known right off the bat.
Start leadership development early. Realize you are not always going to be in the weeds coding, marketing and doing it all. At some point, your organization will look to you for guidance. And this moment will happen sooner than you think.
When we started the company in 2010, management and leadership were not part of our thought process. But when we crossed the threshold from 10 employees to more than 20, communication started to become a problem. We needed to be more active about conveying our mission and how each person’s role fits with the rest of the team.
Misunderstandings can quickly snowball and hurt morale. You need to think about how not to be just players but coaches and then team managers.
Keep asking for help. For venture-backed companies, this is less of a concern: When you have investors, you have a board. You already have people who help you hire, identify the greatest challenges and give personal advice. For a bootstrapped company like ours, no one was going to give advice unless we asked for it.
It is important to be proactive. Get out of the building, start looking for an advisory board and ask as many people as possible about the challenges of scaling your business.
How to do that? For me, I found that scouring the connections of my LinkedIn contacts and getting an introduction was invaluable. When I cold-called people I hoped to learn from, my success rate was higher than 50 percent. When I was introduced via a mutual contact on LinkedIn, my success rate was 100 percent. Remember, you’re not pitching a product, you’re looking to leverage the expertise of others. People are generous with advice, if you ask.
Hand it over. As the company grows, so does your impulse to work longer hours and do more tasks. But you just end up watching the to-do list grow longer. To grow your business, you need to build in time to grow yourself. So the best investment you can make is to hire people you can trust to take things off your plate.
Find people who can lend a hand in making decisions. If you don’t delegate responsibility for making some decisions, you will become the bottleneck in scaling your operations.
Learn to ask questions. When working with direct reports, the most difficult thing to learn is to not tell them what to do but to help them see the light on their own. The key is to try as much as possible to speak in questions, not in statements. And that question shouldn’t be “why,” as in why don’t you do this or why didn’t you do that?
Instead, questions should be more along the lines of: What was your thought process? What was your goal? How did you come up with this list? What are the pros and cons of this?
Learn to end the question at the question mark. Leave it open ended, and don’t add, extrapolate or explain.
This is not intuitive -- your gut will want to just tell your employees what to do. If you do that, you’ll replace a lengthening to-do list with a lengthening line out your door of employees looking not to be told what to do.