What do Michael Jordan , Michael Scott , and Jordan MICHAEL Ostroff in 2016 have in common?
It’s not the Michael thing…and it’s not that all three are allergic to delegating. (Although two of us definitely were. And it’s not the guy with six rings…)
Instead, it’s about getting out of the day-to-day and into a real CEO role.
Michael Jordan stopped trying to play every position and trusted Kukoc or Kerr or someone else to take SOME of the game-winning shots.
Michael Scott… tried to play every position and somehow also made it everyone else’s problem. And 2016 me…well he ALSO tried to play every position and ended up making it a problem.
So here are 5 tips that actually work, in real firms, with real humans (and real chaos) to get you out of the day to day grind and into running a business you can be proud of while living a life that’s even better!
Tip 1: Stop calling it “helping.” It’s stealing.
When you jump in to “help” with intake, fix a paralegal mistake, rewrite a client email, or “just review this one thing”… you’re not helping.
You’re stealing:
their opportunity to get better their confidence time from your actual job and sanity from Future You It feels noble. It’s not. It’s you being the firm’s emotional support animal.
CEO shift: If you touch it twice, it needs a system or a person who isn’t you.
If you keep grabbing the same category of “little fires,” your job is not to keep getting faster at putting out fires.
Your job is to stop the arson without a Dwight Shrute fire drill needed.
Tip 2: Run a meeting that makes you unnecessary
This is THE biggest CEO move that builds a rhythm and keeps the firm moving without you needing to be the human GPS. I have my meetings on Monday, you can too (or pick another day).
The meeting should do three things:
Scoreboard : What numbers matter this week? (Leads, consults, signed, cases moving, cash collected, whatever you track.)
Bottlenecks : What is stuck? Who owns it? What’s the next step?
Commitments : What is each person doing by Friday?
If your meeting is “updates around the room” and vibes, you don’t have a meeting. You have a podcast no one wants to listen to. This should be more Nick Fury getting the Avengers together to fight Loki/Thanos/existential dread…
CEO shift: You’re building operating cadence, not hosting group therapy.
(Although honestly, some weeks it’s both.)
And yes, at some point you do not even need to run the meeting, but for now you’re in charge!
Tip 3: Decide your new job description (and quit your old one)
Most law firm owners try to become the CEO while still doing:
lawyer work intake HR marketing “tech support” and occasional janitor duties because “someone left dishes in the sink again.”
That’s not a CEO role. That’s a season of Survivor: Office Edition (side note…I would 100% watch this show).
The practical play: write a one-page “CEO job description” with 3–5 responsibilities. 5 MAX.
For example:
Revenue strategy (marketing + sales conversion) Leadership (hiring, coaching, accountability) Financial oversight (cash, profitability, runway) Operations oversight (systems, KPIs, bottlenecks) Networking with 5+ a year referral sources Then compare it to your actual week.
If your calendar says your #1 responsibility is “random Slack replies,” we have identified the problem.
CEO shift: You can’t climb into the CEO seat while still holding the employee handbook and the mop.
Tip 4: Create one “No-Interruption Block” per day
If you want to be a CEO, you need time to think. I know. Wild concept.
Most law firm owners have a calendar that looks like a toddler on Red Bull did their scheduling.
Start with one protected block per day:
60–90 minutes same time if possible phone on Do Not Disturb team knows to only interrupt in a REAL emergency (and they know what those are) And just so we’re clear, “the client is mad” is not an emergency. Sometimes it’s just Tuesday.
What you do in that block:
review KPIs write/refine a system work on hiring improve consult conversion plan the next quarter think like a person with a business, not a business with a person
CEO shift: Your work will expand to fill the space you don’t protect…to protect it
Tip 5: Delegate outcomes, not tasks
This is the one that changes everything.
Most owners delegate like this: “Can you do this thing?” or worse “do this thing!”
And then they keep hovering because they didn’t delegate the outcome, the standard, or the finish line.
Try this instead:
Outcome : “By Friday, we have X done.” Definition of done : “It includes A, B, C.” Autonomy : “If you hit a decision, here’s the rule for choosing.” Check-in : “Update me Thursday at 2.” That’s CEO delegation.
That’s how you stop being the bottleneck. Also, if you are already doing virtual meetings, let AI help you delegate.
I cannot stress enough how good LLMs are at filling in some of the gaps you didn’t think about when delegating AND making sure the other person understands what you are trying to have them do. Google will do this live during your meetings. Just ask Gemini to take what you just told them and identify the holes and turn it into a clean SOP then have the person review that and ask questions.
And yes, the first few times will be messy. That’s normal. Batman didn’t build the Batcave in a weekend. (Also he had Alfred, which is kind of the whole point of this newsletter.)
CEO shift: If you delegate a task, you get a task back. If you delegate an outcome, you get a leader.