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<img src="/icons/warning_gray.svg" alt="/icons/warning_gray.svg" width="40px" /> Disclaimers
- All of the habits, methods, and practices I recommend here are recommendations. They’re things I’ve seen work for other people, but they may not work for you. So if any point you think any of this is too prescriptive, know that it may be! You are the CEO/CXO/founder of your company, you’re a leader, you’re an adult, and I believe you can figure out habits and practices that help you achieve your goals. What I teach here are merely things I’ve seen work in a lot of cases, and I hope you’ll give them a try as an experiment to see if they work for you, too.
- Most of the mental models and ideas in this doc came from someone else. Where I can, I’ve done my best to provide attribution.
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Getting the Most Out of Coaching
Five Levels of Evaluating Coaching
Measuring ROI
Baseline Habits
- Preparing for Coaching Sessions: While you can use the time with me however you want, I find a huge different in the quality of the time I spend with clients when they set aside 15-60 minutes on their calendar before our call to prepare for the session.
- On Time & Present: Show up to our sessions with the same amount of professionalism as if you were coming to my office. (e.g. Limit walking sessions due to bad service, noise, etc.; Do your best to be on time OR let people know as soon as you realize you’ll be late). For more, read Matt Mochary’s On Time and Present.
- Planning & Prioritization: Everyone has different routines around planning and prioritization, and it’s significantly harder for folks with ADHD. It matters less what your routine looks like and more that you have one at all. You need to make sure you know what the most important things are for the company and for your week so you can communicate with your team about what’s important so they can make decisions about how to prioritize their time.
- 1:1 Meetings with Direct Reports: A lot of people hate 1:1s, but I’m convinced that’s because most of them are run very poorly. Let’s talk about whether you’re holding 1:1s, how you’re running them, and go over my preferred methodology. See M 2. One-on-Ones (1:1s). Doing one-on-ones well, should allow you to hold less frequent one-on-ones with increased output, alignment, and autonomy for your direct reports.
- Tracking Individual Performance: Many of coaching sessions end up centering around underperforming team members. There’s a ton of nuance here, but one of the most important habits for any manager is to make sure you’re keeping a weekly log of your direct reports’ performance so you can have at least a somewhat objective sense of each person’s performance over time. Doing this will also have the added benefit of forcing you to think about what it means for each person to be below expectations, meeting, exceeding, and so on. See:
- Running Great Meetings: Andy Grove called meetings the managerial medium. An hour long 4 person meeting with people being paid $150K / year costs ~$290 before benefits and taxes. Leading by example by making sure meetings have clear owners and agendas is an easy way to make sure your team isn’t getting bogged down in meetings that could have been emails. See Run Efficient Meetings That Don’t Suck.
Trusted Advisors & Contractors
Below is a shortlist of advisors and contractors I wholeheartedly recommend working with, should you find yourself in need of a specialist. This is by no means a complete list of people I’m willing to introduce you to, but instead is a list of my most recommended folks.
Legal
Michael Brown, Fenwick. [email protected]
- I worked with Michael at Holloway. He was fantastic.
- He now works with several of my clients and two of my closest friends’ companies.