3. Own your one-on-one. Your boss may be big on team-wide collaboration, which puts that much more pressure on you to initiate one-on-one time when necessary. “Start by seeing yourself as the owner of one-on-one meetings with your manager,” encourages Rachel Ernst, Reflektive‘s VP of Employee Success. “This process includes everything from setting the appropriate cadence of one-on-ones to preparing an agenda and leading the conversation.” Aim for weekly private meetings with your boss so that the dynamic becomes less formal over time, making you more comfortable when it’s time to start hard conversations.