Get Comfortable with Being Uncomfortable: 3 Lessons from a First-Time CEO

Brent Chudoba

July 13, 2020

Earlier this year I joined Biteable, the do-it-yourself video making platform, as CEO. It’s the first time I’ve been in the CEO role, and I was excited for the opportunity and challenge.

I knew that there was a lot to learn and that I’d need to be thoughtful about establishing credibility across the organization. Before I started, I reached out to several mentors, many of whom were founding CEOs, to pick their brains.

One of them has considerable experience as a “professional CEO,” or non-founder executive brought in to help founders scale. When we connected, she told me that sharing knowledge was something she was happy to do, but she always tried to learn something when offering up her limited time.

I’d sent several discussion topics in advance, but she asked that I answer a question before we started: “What are the three most important things you’ve learned or figured out in the past three years?”

Despite having to answer on the fly, I came up with three things that I know were useful to her—and they’ve been equally helpful lessons for me to apply in the future.

1. Your instincts are probably right. Timing probably isn’t.

When I’ve joined businesses, I’ve often spotted issues that seem obvious to address. Typically these are things like roles or entire functions that are missing when a company is run very lean.

Usual suspects are things like SalesOps, HR, recruiting, legal, FP&A, security/compliance. Often, there are other areas of needed improvement like upgrading tools and systems and prioritizing initiatives that take a long time to play out, but will inevitably be critical (e.g., internationalization, mobile).

Founders and startup leadership teams are scrappy, frugal and versatile. They know how to do more with less, which is an incredible advantage that kept them in business and got them to where they are.

When you join a company, it’s your job as the new person to help show them when it’s time to loosen the purse strings, and to trust your experience and instincts. But most importantly, it’s your job not to give up.

A CEO may not be ready to hire all the roles you know you’ll need, or upgrade all the systems that will become bottlenecks for you, or allocate resources for projects that you know are important to start. But that doesn’t give you permission to give up and say, “I told you so,” in a few quarters when your instincts prove to be right—it means you need to do the hard work to teach, pitch and convince.

You are new, so you aren’t going to be dragging everyone along with you. You can only bring them along, and that takes time and persistence. Remember, that’s why they hired you.

But you still need to earn it and prove it.

2. Wait until you’re uncomfortable waiting. Then wait a little longer. Then communicate and take action.

When you start a new role in a new organization, particularly in a leadership position, you have to earn respect.

You were brought in to up-level the team or apply your skills and experience to improve the company. Not everyone needs to like all of your eventual decisions, but you want them to respect the process of how you made them.

How you onboard and educate yourself will play a critical role in the respect you earn. At a startup or high-growth organization, there’s one time, and one time only, where the expectations on your output are low and the ability to learn, meet people and educate yourself is high: in your first several weeks at the company.

Use this time. Use all of it.

I’ve entered many organizations feeling high conviction about something, and then after several weeks of team interviews, customer conversations and leadership meetings, completely changed my mind. I’ve also had situations where I felt strongly about some change that needed to happen, did all my research, asked lots of questions and still felt strong, but with much more team buy-in once I made decisions since it was clear I sought out input.

When you join an organization, decide to wait to make any material decisions for a specified period of time until you’ve done the work needed to make great decisions. Maybe that’s a month, two months, three. Wait that full time.

For safe measure, make sure the time you wait is a little longer than feels comfortable to you (you should be beyond itching to take action by the time you are ready). Then, when it’s time to take action, get to work and make sure you are clear in your communications of how and why you made decisions.

3. People are the only enduring unlock

When you make a great hire, they don’t just fill a role; they take your organization to a higher level. If that hire is relatively senior, they are probably so much better than you in their position, that they become a multiplier for their entire department. Your time can shift to other important focus areas, and toward being proactive instead of reactive.

We all know that hiring is essential. We know that hiring decisions are the most important decisions you’ll make. We know these things, but we often don’t treat hiring like this.

Hiring managers should take on primary sourcing responsibilities for their roles; they should be deeply engaged in running a tight process, gathering feedback and closing candidates. They should seek diversity and candidates with opinions and experiences that will make the team better.

“When you make a great hire, they don’t just fill a role; they take your organization to a higher level.”

Top candidates should have the red carpet rolled out for them, but they should also hear the good and the not-so-good about your organization so they join with eyes wide open.

People should see their job in a hiring process to raise the bar, not to conduct an interview and provide feedback. There is a saying that “if a candidate is not a hell yes, they are a no.” Not every great hire needs to be perfect in every way, but they need to be a hell yes. Avoid letting a hell yes candidate slip away at nearly any cost.

I knew all these things three years ago, but what I learned is that you cannot ever lower your standards. You have to fight to keep the hiring bar high. And keeping a high hiring bar is as much about your process and effort as it is finding great candidates.

Hiring is hard work, and it should be. The results have more significant potential and enduring impacts than almost anything else you can do.