Headwind: Leadership Practice

The real conversation should not be your first attempt. Headwind is a rehearsal room for managers. Practice feedback, boundaries, saying no, missed expectations, pay and promotion decisions, restructures, and other conversations where the way you say it matters. REHEARSE REAL PUSHBACK Choose a scenario or bring a situation from work. Practice by voice or text with an AI counterpart who has a point of view, reacts to what you say, and does not simply agree. Try one approach, see how it lands, then take another run. GET A DEBRIEF GROUNDED IN YOUR WORDS After a rehearsal, Headwind shows the moments that worked and the moment that cost you. See the leadership behaviors you demonstrated, how much of the conversation you carried, where you softened the message, and examples drawn from your own words. The feedback does not force one perfect script. It helps you become clearer while keeping your own voice. PREPARE FOR THE CONVERSATION AHEAD Describe the person, the context, and what needs to change. Build a practical prep plan with: • A clear opening • A structure for the conversation • Likely pushback • Lines to use when it goes sideways • A goal you can hold onto under pressure KEEP CONTEXT FOR THE PEOPLE YOU WORK WITH Create a private space for each person you manage, work alongside, or report to. Your leadership coach remembers the details you choose to share, helps you think through your next move, and keeps prep and debriefs together. PRACTICE THE MOMENTS MANAGERS FACE • Give direct, specific feedback • Hold someone accountable after the first conversation • Set boundaries and say no without burning trust • Deliver difficult news about pay, promotion, scope, or change • Manage up and handle resistance • Prepare for performance reviews and one-to-ones REHEARSE YOUR NEXT JOB INTERVIEW Practice for the role you want, using the job description and an your CV to make the questions relevant to your experience. Rehearse by voice or text, from recruiter screens to final rounds. Work through questions one at a time with feedback and retries, or run a mock interview and get a debrief at the end. See where your answers were clear, where they needed stronger evidence, and what to try next—all in your own voice. BUILT FOR PRACTICE, NOT PERFORMANCE No audience. No need to get it right the first time. Take 2 is always there when you want to try again. Headwind provides leadership-skills coaching and communication practice. SUBSCRIPTIONS Headwind is free to download and use. The Free plan includes all features, subject to usage limits. Optional auto-renewable subscriptions provide higher limits. Terms of Use: https://tryheadwind.netlify.app/terms/ Privacy Policy: https://tryheadwind.netlify.app/privacy-policy/