A phase-by-phase plan for establishing a baseline, aligning priorities and ownership, and putting an operating rhythm in place. Written for CEOs, owners, and operating executives who want the business to run better, not just a better plan on paper.
How to use this playbook
Most operating problems aren’t solved by a single big decision. They’re solved by getting a clear view of the business, agreeing on a short list of what matters, and then building the habits that keep everyone working on it. Ninety days is long enough to do that properly and short enough to keep the urgency.
This playbook is written for CEOs, owners, new operating executives, and private equity or board sponsors who want to improve how a business runs. It works for a new leader in their first quarter, a management team that knows things should run better, or a portfolio company after an acquisition.
The CEO or the senior operating executive. It can be supported by finance, a chief of staff, or an outside advisor, but it can’t be delegated entirely.
The leadership team throughout, and managers one level down during the assessment and when rolling out the operating rhythm.
Roughly a day a week for the leader, and a few hours a week for each member of the leadership team. More in the first 30 days.
A shared baseline, three to five priorities with owners and measures, a weekly scorecard, and a meeting rhythm that keeps all of it moving.
Understand how the business actually runs today, using facts rather than impressions, and agree on that picture with the leadership team.
Turn the assessment into a short, owned plan: three to five priorities, a single owner for each, a measure of success, and the KPIs the leadership team will review every week.
Put in place the recurring meetings, reviews, and reports that keep priorities moving and catch problems early, then measure what changed against the day-30 baseline.
Phase 1 · Days 1–30
Goal. Understand how the business actually runs today, using facts rather than impressions, and agree on that picture with the leadership team.
Why it matters. Teams that skip the assessment usually end up fixing the most visible problem rather than the most important one. A shared baseline also gives you something to measure progress against at day 90.
Listen and gather. Meet each leadership team member one on one. Ask the same questions of each: what’s working, what isn’t, what would you change first, and what does nobody talk about? Request the last 12 months of financials, the budget, the sales pipeline, and any existing KPI reports.
Go to the work. Spend time with customers, frontline staff, and the people who run core processes. Follow a sale from first contact to cash collected. Note where work waits, gets redone, or depends on one person.
Build the fact base. Rebuild the numbers you need if they don’t already exist: margin by product or customer, a 13-week cash view, customer concentration, pipeline conversion, and on-time delivery. Rough and right beats precise and late.
Agree on the picture. Write a short assessment, five pages at most, and review it with the leadership team in a working session. The aim is agreement on the facts and the five to eight biggest issues, not on solutions yet.
Illustrative example (fictional)
A founder-led services company with about 120 employees has grown revenue steadily, but margins have slipped for three years running. In the first month the new COO finds that gross margin is tracked only in total. Once rebuilt by service line, one line turns out to be roughly break-even and growing fastest. The leadership team had sensed a margin problem but had been debating pricing across the board. The assessment refocuses the discussion on one service line and how it is scoped and delivered.
Phase 2 · Days 31–60
Goal. Turn the assessment into a short, owned plan: three to five priorities, a single owner for each, a measure of success, and the KPIs the leadership team will review every week.
Why it matters. Most businesses have plenty of initiatives and not enough focus. This phase is about choosing, and choosing means deciding what not to do as much as what to do.
Choose the priorities. Hold a half-day leadership session to pick three to five priorities for the rest of the year from the issues list. For each, write one sentence on what success looks like and why it matters now.
Assign owners and plans. Give each priority one owner. Each owner writes a one-page plan: the outcome, three to five milestones with dates, the resources needed, and the measure that shows it’s working.
Build the scorecard. Agree on eight to twelve weekly KPIs that show whether the business is on track. Give each a definition, an owner, a target, and a data source. Start reporting it, even manually.
Stop things. Review every initiative and recurring project already under way. Anything that doesn’t support a priority is paused, scaled back, or stopped. Tell the organization what changed and why.
Illustrative example (fictional)
Following the assessment, the same services company picks four priorities: fix margin in the underperforming service line, put a 13-week cash forecast and monthly close in place, tighten pipeline stage definitions, and hire an operations lead. The scorecard has ten weekly measures. To make room, two internal projects are paused, a new office fit-out and a website redesign, and the reasons are shared at an all-hands meeting.
Phase 3 · Days 61–90
Goal. Put in place the recurring meetings, reviews, and reports that keep priorities moving and catch problems early, then measure what changed against the day-30 baseline.
Why it matters. Plans fade without a rhythm. A consistent cadence of weekly, monthly, and quarterly reviews is what turns a 90-day effort into how the business runs.
Launch the weekly meeting. Start a weekly leadership meeting of 60 to 90 minutes with a fixed agenda: scorecard exceptions, priority updates, open actions, and decisions needed. Send status updates in writing beforehand so the meeting is spent on problems and decisions.
Add the monthly and quarterly reviews. Set a monthly business review covering financials against budget, priority progress, and people. Schedule the first quarterly priorities review. Put the full calendar in place for the next two quarters.
Push the rhythm down. Help each leader set up a similar weekly rhythm with their own team, using the same scorecard logic. Track actions and decisions in one place, and review overdue items first in every meeting.
Measure and reset. Compare the scorecard to the day-30 baseline. Review each priority: done, on track, or needing a reset. Hold a short retrospective on the process itself, and decide what the next 90 days should focus on.
Illustrative example (fictional)
In the services company, the weekly leadership meeting replaces three overlapping status meetings. By week 13 the scorecard shows on-time delivery up and the 13-week cash forecast being used to time a hire. Margin in the problem service line has started to improve but isn’t yet at target. That stays a priority for the next 90 days, while pipeline definitions are marked complete and rolled into the weekly review.
Keeping it going
By day 90 the business should be running on a predictable calendar. Each meeting has a distinct purpose, so none of them becomes a catch-all.
| Forum | Length | Focus |
|---|---|---|
| Weekly leadership meeting | 60–90 minutes | Scorecard exceptions, priority updates, open actions, decisions needed. |
| Monthly business review | 2–3 hours | Financials vs. budget and forecast, priority progress, people, customers. |
| Quarterly priorities review | Half day | Results vs. plan, priorities confirmed, changed, or retired, next-quarter focus. |
| Annual planning | 1–2 days | Strategy, annual priorities, budget, organization. |
The CEO Weekly Operating Dashboard gives you a ready-made scorecard and action log for the weekly meeting.
Perspective
The plans management teams write in a first 90 days are usually sensible. What separates the ones that work is whether anything changes about how the leadership team spends its week.
A short list of priorities, a scorecard reviewed every week, and an action log with owners and dates will outperform a far more sophisticated plan that gets reviewed once a quarter.
Put a recurring weekly leadership meeting on the calendar on day one, even before the assessment is done. Use it to review what you’re learning and to keep a simple action log.
By day 60, when the priorities and scorecard are ready, the habit already exists. The hardest part of an operating rhythm is starting it, and that’s easier when there is no plan to perfect first.
After day 90
Please note: The examples in this playbook are illustrative composites created for explanation. They do not describe any specific company or engagement. This playbook is general guidance, not professional advice for any particular business.
Take it with you
The full playbook as a printable PDF, with the checklists laid out to work through with your leadership team.
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These resources are designed to help you identify opportunities and move your business forward. If you’d benefit from an experienced operator’s perspective, I’m happy to compare notes.