Five Operating Rules to Live By

6 min read
Five Operating Rules to Live By

If I had to distill 25 years of consulting, running companies, and figuring out how to get the results I want in life into five sayings, these are the five.


1) You manage what you measure

You pay attention to what you instrument. If you do not track product development speed or sales close rate, you are guessing. The act of measuring turns a fuzzy goal into a scoreboard that guides daily choices. In one large study of public companies, firms that leaned into data‑driven decision making were about 5–6% more productive than peers, even after controlling for other investments. That is not a small bump—that is a compounding edge. SSRN

Start with outcomes and work backward. If you want growth, pick two leading indicators that actually predict it—say, opportunity‑to‑win by segment and budget deviation in delivery. Track them in one place. Review them every week. Change one thing at a time so you can see cause and effect.

A caution: measurements can bite if you pick the wrong proxy. Goodhart’s law says that when a measure becomes the target, it can stop being a good measure. Translation: if you reward activity counts, you will get activity, not results. So tie the metric to the outcome you truly care about, and keep the set small. Two or three numbers beat a dozen vanity metrics. PMC

How to put this to work this week

  • Sales: Track opportunity‑to‑win by segment and the top three loss reasons. Run one experiment to reduce the most common loss reason every week.
  • Product: Track cycle time from first commit to production and flag any pull request stuck longer than two days.
  • Customer success: Track customer satisfaction and adoption with a simple red/amber/green health score. Pull three “amber” accounts forward each week.
  • Company level: Set objectives and key results (OKRs) with three to five measurable key results per team. Keep them visible; review progress weekly. Rework

2) Progress over perfection

Perfect plans do not ship; small steps do. Waiting for the flawless answer turns into months of drift. Shipping the smallest useful version lets you learn in the real world and improve. Facebook made this part of its operating system years ago—“done is better than perfect”—and described it in Mark Zuckerberg’s investor letter about “The Hacker Way.” That ethos is not about being sloppy; it is about short feedback loops and constant iteration. WIRED

You see this any time a team is stuck in meeting mode. People raise real concerns—edge cases, missing data, dependencies—but the list becomes a reason to stall. We recently rolled out an updated customer success approach at PS Ignite. It was not the final form we wanted. We shipped a minimum viable product (MVP) anyway. We learned more in the first two weeks than in the prior two months of talk, and the second iteration fixed half the rough edges we were worried about.

Speed matters in tough situations too. Bain’s turnaround work describes teams that accelerate learning loops and refuse to get bogged down by excessive precision; “adequate approximations will do.” That line captures the spirit here. Decide, test, observe, adjust. Repeat. Bain

How to put this to work this week

  • Define the minimum viable product (MVP) for the change you keep debating.
  • Time‑box it to two weeks. Publish “good enough” acceptance criteria before you start.
  • Schedule a 48‑hour post‑launch review: one metric, three observations, one change.
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3) Would you rather be rich or right?

Most blow‑ups are not about facts. They are about pride. I have wasted hours trying to win an argument that, even if I won it, would cost me the outcome I wanted. When you feel the heat rise, pause and ask: What outcome do we want in 90 days? Write it at the top of the thread.

The negotiation research calls this principled negotiation: separate the people from the problem; focus on interests, not positions; use objective criteria; look for options that satisfy both sides. Do that, and you will stop keeping score on the argument and start optimizing for the result. Pon at Harvard

A common example: a customer is behind schedule. Some of it is on them; some is on you. You can spend a week proving exactly who missed what. Or you can invest targeted services to get them to success and protect the account. You might swallow a short‑term loss to keep a referenceable customer and the expansion revenue that follows. Put numbers to it: sacrifice $10,000 this month to protect $150,000 next year and a logo you can cite in every deck. That math is simple.

How to put this to work this week

  • In any tense thread, post the 90‑day outcome and ask everyone to react to that.
  • Offer two concrete fixes that achieve it. Avoid blame language. Be specific on scope.
  • In proposals, add an “interests” sentence: “You want shorter time‑to‑value; we want a successful reference. This plan does both.”

4) Talk is cheap, whiskey costs money

Ideas and slide decks are free. Results cost time, focus, and budget. Do not reward the plan. Reward the outcome. If your partner program throws great events and yields zero pipeline, that is not a win. If your implementation process has 500 steps and most projects still miss their date, the checklist is not helping.

Harvard Business Review put a fine point on this years ago: splitting “strategy” and “execution” into separate worlds creates a gap where good ideas go to die. The actual work is linking the choices you make to the actions people take every day. So redesign your incentives to reinforce that link. Harvard Business Review

Where to move incentives

  • Alliances and partners: Shift from “meetings held” to sourced and influenced pipeline and closed‑won.
  • Implementation: Shift from “tasks completed” to on‑time, on‑budget go‑lives and time‑to‑first‑value.
  • Marketing: Shift from form fills to sales‑accepted pipeline and opportunity conversion.
  • Engineering: Shift from tickets closed to cycle time and incidents per release.

If a metric does not predict the outcome you care about, stop staring at it. If a plan does not change behavior, stop praising it.


5) Belt and suspenders

For critical work, assume things fail and design multiple independent catches. Your goal is not perfection. Your goal is that one miss never becomes a catastrophe.

Safety training is built on this idea. The California Department of Justice lists six basic firearm safety rules: treat every firearm as loaded; keep it pointed in the safest direction; keep your finger off the trigger; know your target and beyond; know how your firearm operates; store it safely. Each rule is a layer. If one fails, the others still prevent harm. The point is redundancy. California DOJ

Aerospace takes redundancy to the extreme. The Space Shuttle’s avionics used a five‑computer central processing complex with voting logic so that one failure did not doom a mission. They did not rely on a single perfect component; they assumed failure and built for it. That mindset applies well beyond rockets. NASA Technical Reports Server

Where to add a second catch

  • Project delivery: If one step keeps getting missed, add two checks: a scoping checklist item and a pre‑flight gate in quality assurance.
  • Data protection: Keep both cloud and local backups and test restores monthly.
  • Finance: Require two‑person approvals for sensitive payments plus an automated alert at a defined threshold.
  • On‑call: Cross‑train so no single absence cripples your response.

If a one percent failure hurts too much, design your system so it takes two independent misses to cause damage.


Wrap‑up

Measure what matters. Implement small and keep learning. Trade pride for outcomes. Reward results, not rhetoric. Add belt‑and‑suspenders where failure is expensive.

I hope you found this helpful. Drop your comments or questions below and sign up for my weekly newsletter.


  • You manage what you measure. Pick two outcome‑linked metrics, make a public scoreboard, review weekly. Firms that institutionalize data‑driven decisions see 5–6% higher productivity. SSRN
  • Progress over perfection. Ship a minimum viable product in two weeks, then adjust. Facebook’s “done is better than perfect” culture codified this years ago; it works because short feedback loops beat long debates. WIRED
  • Would you rather be rich, or be right? Ask, “What outcome do we want in 90 days?” and apply principled negotiation—focus on interests, not positions—to get there. Pon at Harvard
  • Talk is cheap, whiskey costs money. Move incentives from activity metrics to real results; strategy‑execution splits kill good ideas. Harvard Business Review
  • Belt and suspenders. Add redundancy for critical steps—think firearm safety’s layered rules or Shuttle‑style voting computers—so a single miss does not become a crisis. California DOJ+1
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