When I launched RiseGuide, a self-improvement platform letting people become their best by learning from the best, I wanted to offer a beneficial alternative to doomscrolling. We aggregated thousands of hours of expert knowledge into short, interactive, and practical daily lessons. Now, more than 500,000 users are putting their screen time toward something genuinely useful.
But realizing my vision hasn’t always been easy, especially as CEO. You need feedback to build confidence, identify issues, learn, and improve. But these are all things that are difficult to get as a CEO. You don’t have a formal manager to provide performance reviews, personal development plans, or one-on-ones, so you have to find alternative ways to evaluate how you’re doing and where you can improve.
These are the three practices that helped me scale my startup.
1. Hire employees who challenge you
Affinity bias unconsciously draws us towards candidates who think, communicate, and work as we do. That can lead to groupthink and create teams where everyone offers the same input. During the hiring process, I consciously trained myself to look out for two varieties of what I call “special” hires.
The first attribute I looked for in candidates was high standards that they stick by. People with the confidence to turn the tables and essentially interview me. Kate, RiseGuide’s senior creative producer, is the perfect example. During our first meeting, she asked me a lot of questions, and she crowned it by insisting I show her around the office after I’d casually mentioned the view. I used to be wary of people who refused to let me lead, but I’ve come to realize that true stars choose their employer and naturally take charge.
I also looked for people who thought differently from me. Sometimes, the right hire is someone who is your opposite and brings an entirely different perspective. Take my CMO, Stas. While I prefer to come up with the big ideas, he figures out how to execute them. He comes to every meeting with an agenda, and I’ve never seen him lose his cool.
What makes these hires so valuable is that they never stop challenging you. There’s always somebody in the room who is going to question your thinking or offer a different approach, which provides constant feedback and ensures you reach the best decision.
2. Give everyone an opportunity to share
It’s important that you not rely only on senior management to offer insight into your performance. After all, your leadership impacts the entire organization, yet it can be tough for those lower down to share their frustrations.
I decided to run an organization retro, a team-wide meeting where everyone had permission to share their honest thoughts. This led to people raising many issues that had never occurred to me. The team had a clear picture of our goals for the week, but no real sense of what we were trying to accomplish beyond that. I also had a habit of sharing information in meetings, over lunches, or during water-cooler conversations and expecting it to spread to the 70% of our team members who work remotely. Before having this meeting, I believed we were all on the same page. But I found out that some people expressed feeling uninformed or left out.
The point that stuck out most was that we weren’t celebrating wins. I’m not someone who dwells on triumphs. I view them as the natural result of hard work, but I came to realize that not everyone thinks like me.
It’s important to note that feedback is valuable only if you act on it. In addition to the meeting, I started writing two long-form updates each week that I sent to the entire team, covering strategy, performance, hiring, and the wider market. Now, everyone is clear on where the company is heading over the next five years.
We also started celebrating. Big or small, we now give credit for achievements and reward hard work with fun, informal activities, whether that be Zoom wine tasting sessions or team-wide quizzes.
3. Encourage boardroom conflict
Six months after the retro, RiseGuide was in a strong position, and the internal feedback reflected that. However, board meetings had become a formality. I would share stats and be told everything looks great. No one asked questions or raised issues. Without that feedback, I felt there was a risk of complacency creeping in. So I set out to find someone who would challenge me even when times were good.
After plenty of thought about the person I wanted on board, I came up with the following criteria, which have since led me to many perfect board hires. I want someone who:
- has enough experience that I would genuinely respect their input, even when it goes against mine,
- is an independent thinker, and won’t go with the crowd or follow the leader when they disagree,
- speaks up and argues until the end, not because of a personal stake but because they care, and
- disagrees only when they believe it’s necessary, not simply to show they can.
It is important to give them the means to get to know you as a leader. Two of my board members, for instance, now join our weekly, monthly, and informal meetings, and they’re in our main Slack channels. They know what’s going on and feel the atmosphere within the team, so they can provide feedback based on more than a slideshow of metrics.
The benefit of building opposition
Many founders avoid friction because they believe it will slow them down and undermine their authority. And it does, but I don’t think that’s a negative. Growing as a leader isn’t about staying comfortable. It’s about keeping yourself accountable to do what’s best for your company—and that requires your best people challenging and questioning you in the process.