Why a CEO Hired a Board Member to Argue With Him

Oleksandr Matsiuk, cofounder and CEO of RiseGuide, a microlearning app, faced an unexpected challenge: no one was responsible for telling him how to improve. As CEO, he lacked a formal manager, performance reviews, or a personal development plan. His performance was judged by the company’s success, but that didn’t sit right with him. “If the business is growing, few people will say, ‘This could have been better,'” Matsiuk said. At board meetings, he’d present ideas and hear, “Everything is clear. Keep doing a great job.” That frustrated him. He wondered if he and the company were living up to their potential. So Matsiuk built a feedback system around himself. He hired opinionated, independent thinkers who weren’t afraid to challenge him. During interviews, he watched how candidates behaved. One creative producer questioned him for 45 minutes and even asked for a tour of the office. Another challenged the brand strategy instead of complimenting it. “If she made me do that during an interview, imagine what she’ll do when we work together,” he thought. He applied the same criteria to his board. He wanted someone who understood the business model, knew him personally, and could spend time with the team. The person he chose challenged him before even joining, asking why he needed him and what would happen when they disagreed.

About a year ago, Matsiuk proposed tripling growth and doubling the team for the next six-month season. His board member asked, “Why do you think that’s ambitious? Why can’t you go higher?” He suggested a target twice as high and kept pressing on obstacles and bottlenecks. Though it pushed Matsiuk outside his comfort zone, he eventually agreed. They hit the higher target. “You solve different problems when you aim to grow fourfold instead of twofold,” Matsiuk said. His advice to other CEOs: create systems that challenge your outputs, not just measure outcomes. Someone should be able to tell you a Slack message was poorly written or your goals weren’t ambitious enough. Embrace tough feedback—it’s not a threat to your authority. Better outputs lead to better outcomes.