The CEO who hired someone to argue with him

Oleksandr Matsiuk built feedback systems to challenge himself because nobody else would.

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Sep 20, 2026

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The CEO who hired someone to argue with him

Oleksandr Matsiuk built feedback systems to challenge himself because nobody else would.

In brief

Oleksandr Matsiuk built feedback systems to challenge himself because nobody else would. RiseGuide CEO Oleksandr Matsiuk hired a board member specifically to argue with him, recognising that fast growth can mask a leader's flaws and that honest feedback rarely reaches those at the top. Originally reported by Business…

The CEO feedback problem

Oleksandr Matsiuk, cofounder and CEO of RiseGuide, realised that as a leader he had no formal manager, performance reviews, or personal development plan. Growing a company created a problem: nobody was responsible for telling him how to improve.

Why honest feedback never arrives

At board meetings, Matsiuk would present ideas and hear only praise. If the business is growing, few people will say the approach could have been better. He wondered if he was living up to his potential and if the company was too.

“This could have been better.”

Building systems for feedback

Building systems for feedback

Matsiuk began designing feedback systems around himself, including direct reminders to employees that he wanted their honest opinions. When hiring, he looks for opinionated, independent thinkers who challenge him during interviews, not candidates who simply compliment the company.

Hiring a board member to argue

Matsiuk applied the same criteria when selecting a board member. He wanted someone who understood the business, knew him personally, and could spend time with the team. Most importantly, he needed someone who would not give up arguing until one of them proved their point.

The board member who pushed higher

About a year ago, Matsiuk proposed tripling growth and doubling the team. His board member asked, "Why do you think that's ambitious? Why can't you go higher?" and proposed targets roughly twice as high. His questions pushed Matsiuk far outside his comfort zone.

“Why do you think that's ambitious? Why can't you go higher?”

The lesson from aiming higher

Matsiuk's board member had experience with a similar business model and made arguments strong enough to change his mind. They raised their targets and eventually hit them. The experience taught him that you solve different problems when aiming to grow fourfold instead of twofold.

The big picture

RiseGuide CEO Oleksandr Matsiuk hired a board member specifically to argue with him, recognising that fast growth can mask a leader's flaws and that honest feedback rarely reaches those at the top.

Read the original on Business Insider

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Life is short. Keep it sweet. Respect others' opinions and be kind!

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