I’m the CEO of a self-improvement app, and I hired someone on my board to argue with me

This as-told-to essay is based on a conversation with Oleksandr “Alex” Matsiuk, cofounder and CEO of RiseGuide, an expert-powered microlearning app.

The company has grown to 110 employees across 12 countries since its founding in 2024.

The essay has been edited for length and clarity.

Becoming the CEO of a fast-growing company created a problem I hadn’t anticipated: Nobody was responsible for telling me how to improve.

I decided that if honest feedback wasn’t reaching me naturally, I needed to build a system that would deliver it.

That included hiring outspoken employees and bringing someone onto my board specifically to argue with me.

As CEO, I don’t have a formal manager, performance reviews, or a personal development plan.

My performance is largely judged by the company’s performance, but that isn’t always the right approach.

A CEO can be doing something wrong or have plenty of room for improvement.

If the business is growing, few people will say, “This could have been better.” At board meetings, I would present an idea and hear, “Everything is clear.

Keep doing a great job.” That frustrated me.

I might have been outperforming the competition, but was I living up to my potential?

Was the company living up to its potential?

Feedback is essential for any professional’s growth, and CEOs have flaws, perhaps even more than other people.

I began designing feedback systems around myself, including direct reminders to employees that I wanted their honest opinions.

When hiring, I look for opinionated, independent thinkers.

There isn’t one interview question that identifies them.

We often approach people who aren’t actively looking for jobs.

The best candidates know their value, so they interview me as much as I interview them.

One creative producer, for example, questioned me for 45 minutes.

When I mentioned our beautiful office and its view, she said, “Show me.” I picked up my laptop and gave her a tour.

I thought: If she made me do that during an interview, imagine what she’ll do when we work together.

Another candidate came in deeply prepared and challenged our brand strategy rather than simply complimenting us.

I applied similar criteria when selecting a board member.

I wanted someone who understood our business model, knew me personally, and could spend time with our team.

I can be passionate when I strongly believe in something, and people sometimes stop arguing with me.

I needed someone who wouldn’t give up until one of us proved our point.

The person I selected challenged me before he even joined the board.

He asked why I needed him, why he needed the role, and what would happen when we disagreed.

That was how I knew he was the right match.

About a year ago, I was setting targets for our next six-month season.

I proposed what I considered ambitious goals: tripling the company’s growth and doubling the team.

My board member asked, “Why do you think that’s ambitious?

Why can’t you go higher?” He proposed a target roughly twice as high as my original one.

Then he kept pressing: What were the obstacles?

His questions pushed me far outside my comfort zone.

When I commit to a target, I intend to achieve it, so reaching for the stars isn’t easy for me.

He had experience with a similar company and business model.

He knew the bigger goal was possible and made arguments strong enough to change my mind.

We raised our targets and eventually hit them.

The experience taught me that you solve different problems when you aim to grow fourfold instead of twofold.

You may never consider the steps needed for fourfold growth unless you first set it as the goal.

My advice to other CEOs is to create systems that challenge your outputs, not just measure your company’s eventual outcomes.

Someone should be able to tell you that a Slack message was poorly written, your goals weren’t ambitious enough, or a person you hired wasn’t competent enough.

If you encourage tough feedback, embrace it, and don’t treat it as a threat to your authority.

Better outputs eventually lead to better outcomes.

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