Put me in, coach - or Put the coach in?: Operating vs. Advising
What is the difference between advising and operating? Until this year I thought it was Leverage vs. Ownership respectively - but no longer.
If you’re weighing these paths, the real tradeoff to interrogate is: Do you get more fulfillment from working in a team 🧑🤝🧑 or individually 🧑? If you choose that properly for yourself, your work is more personally rewarding and more likely effective of course. In my case, a standing team is more rewarding and more naturally available in an operator context. But through a fortunate set of recent projects, I've seen both Leverage and Ownership is possible in either operating or advising modes, it's a false choice I realized one can design to avoid.
Ownership in advising: Deliverables that can tie to immediate, regular outcomes drive this feeling (over, say recurring hours on the weekly top priority, or a major capstone result)
Leverage in operating: Because you own the problem regardless, solutions that have leverage (e.g. a broader solve, or less time to solve next time) should always be the goal.
🧑: What I mean by “leverage” is the thing I love most about being a consulting advisor, both with a large firm (Booz Allen) and as a sole proprietor of an LLC. You come in at a crucial point, and for short bursts of time - either a couple hours a week or as many hours as you can in a set period. You work to add something critical that takes things to the next level or stage.
🧑🤝🧑: And while “ownership” is technically available in advisory - e.g. when you get a share of upside, hit the engagement's goal - being an operator you own the problem and the solution. You wake up with it as your main mission, accounting for it every day with action. Checking in on your investment is nice, but it’s like passive income. Great for a portfolio, but definitionally not life’s work.
🍕: Ownership in advisory is not about getting credit, equity stakes or a billing level that says you’re vital. It’s more about ensuring what you are consulting about has outcomes immediately built in. Even meetings, and especially incrementally-valuable deliverables. Help close a hire, a deal, hit a weekly number. Your client / advisee may or may not take the next major step successfully no matter how you’ve empowered them, but framing the work and the value as what happens in the moment (alongside a final business or equity outcome) makes a better engagement for everyone. With advisor equity being more commonly granted over a vesting schedule these days, it's also more aligned anyway.
🚑: When family health crises prevented me from doing more than some fractional work for most of 2024, I was fortunate that my work with a couple folks (like Mike Meaney, PhD and Lisa Luedde - and others who know who you are) showed me that you can have ownership of an outcome even when you don’t get to ship everything yourself. Unlike a time-bound consulting arrangement, these engagements and the nature of their goals would force me to think of what could be done (or failing that, decided) in every single interaction to move the ball forward. This is a discipline to carry forward, and mimics a rule I adopted in operating for ensuring every meeting has a goal outcome asserted from the outset.
🧢: I’ve coached my kid’s baseball team for a few years - definitionally, I'm not on the team. We coaches think we’re helping them develop skills, master a rule, but really we’re teaching them how to love learning something that they can do without us coaches, but they can’t do without the others on their team. With the basics understood, we realized very quickly that the kids do best and enjoy it most when we get them helping each other. We now create practice schedules and provide roles on the team so that this happens not just organically, but automatically in the process of having a great experience and outcome.
Go Dragons!
⛏️ vs 🤖: Similarly, in reflecting on my recent operating roles - and to a lesser extent in AI-related advisory - it’s amazing how much leverage can be gained in strategies to add and calibrate for that by design. E.g., summarize user feedback and tie it to your roadmap automatically in a tool. Or just track the multiple of time it takes digging for it (vs simply reviewing it) when the process is manual. Reinforcement Learning with Human Feedback (or RLHF) isn't just for robots or an GenAI buzzword - visible work product and living documentation has helped human agents for much longer.
Or lastly, think (I do almost every day) about following the first, most shocking principle a long-retired mentor gave me: Never make yourself indispensable. Whether advising or operating, that’s leverage AND ownership.
