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Business planning retreat: a 1-day guide for contractors

Topic: Bid, get paid and grow · Related service: Consulting for contractors: bid with margin and grow with order

Armando Ehrenzweig
By Armando Ehrenzweig
Published: November 17, 2025 · Updated: October 26, 2026 · Reading time: 7 min
Dueño de negocio con libreta y laptop planeando en una sala tranquila, en un retiro de planeación de negocios

A business planning retreat is a day away from the job site. You use it to think about your company, not the next task.

It is not a trip or a vacation. It is a day with your numbers on the table to decide what to change next year.

In short

  • A retreat is worth it if you leave with decisions and dates.
  • First, get your key numbers ready: sales, profit per job, accounts receivable and fixed expenses.
  • Follow an agenda from 8:00 a.m. to 4:00 p.m. so you do not lose the day in chatter.
  • End with a 1-page sheet: 3 goals, 3 numbers and 3 projects with an owner.
  • Do a 30-minute review every month to follow up.

What a business planning retreat is (and what it is not)

It is a day set aside, with no phone, to review your business and plan.

It is not a day off, a meeting to scold the team or a wish list with no date.

It is a simple way to do strategic planning for a small business, without consultants or hard words. Big companies do it every year. The Business Development Bank of Canada (BDC) publishes a 5-step guide to organize it.

What a planning day is for

A planning day gets you out of firefighting mode. It helps you:

  • See the whole year, not just this week’s job.
  • Decide which jobs you want more of and which to drop.
  • Set prices and business goals with data.
  • Choose 3 projects to improve your company.

If you feel you are always busy but not getting ahead, read busy or productive: how to stop putting out fires.

Before: what to prepare

Bring these numbers printed out:

  • Sales for the year, month by month.
  • Profit by type of work. If you don't know how to figure it out, read profitability for contractors.
  • Accounts receivable: who owes you and since when.
  • Monthly fixed expenses.
  • List of your 10 best and 5 worst clients.

Pick a place away from home and the office. Turn off notifications.

Keeping your books up to date makes this step much easier. With a bookkeeping report (keeping your books up to date) you can pull these numbers in minutes.

Hour-by-hour schedule

Follow this agenda so you do not lose the day in chatter. Each block ends with a concrete result.

TimeActivityResult
8:00 – 9:00Review the year: what went well and what didn'tList of 5 wins and 5 problems
9:00 – 10:30Review the numbersProfit by type of work
10:30 – 11:30Clients and servicesWhat to sell more of and what to drop
11:30 – 12:30Lunch and a walkBreak
12:30 – 13:30Goals for next year3 measurable goals
13:30 – 14:30Projects to reach them3 projects
14:30 – 15:30Owners and datesWho does what and when
15:30 – 16:00Fill out the 1-page sheetPlan ready

How to choose your retirement goals

Many owners show up with loose ideas. Before you write down a goal, ask yourself three questions:

  • Can it be measured with a number and a date?
  • Is it up to you and your team, not the weather or the market?
  • Does it bring you closer to earning more per job or getting paid faster?

Imagine you say, "I want to grow." That can't be measured. But "cut days to get paid from 45 to 30" can. This is an illustrative example, but it shows the difference between a wish and a goal.

Who should be in the room

The first time, go alone or with your partner. It's easier to review the business numbers without interruptions. Then share the plan with your supervisor and the office person. That way everyone knows what their part is.

1-page sheet

At the end of the day, your yearly plan as a contractor should fit on one page. Fill it in with this:

BlockWhat to write
3 goalsExample: sell $500,000, 12% net profit, hire a supervisor
3 key numbersExample: margin per job, days to get paid, sales per month
3 projectsExample: new estimate format, weekly collections, referral program
Owners and datesOne person and one date per project

The examples in the table are only to give you ideas. Write your own goals.

Example: a painting contractor

This is an example with made-up numbers to illustrate. Rosa has a painting company with 6 employees and sells $420,000 a year. At her retreat she saw that commercial painting left her 15% net and residential only 6%.

What Rosa discovered on her retreatExample with made-up numbers. Net margin on commercial painting: 15%. Net margin on residential painting: 6%. Rosa's net profit before the plan: 8%. Six months later: 11%.Rosa: net profit by type of jobCommercial15%Residential6%Before the plan8%6 months later11%Each bar shows 1% of net profit = 20 px (illustrative example).
Example with made-up numbers to illustrate: the longest bar is commercial painting; the bottom two show the change in Rosa's net profit.

He decided on 3 things: raise his residential prices 8%, find 3 property managers and collect every Friday. In the example, his net profit went from 8% to 11% in 6 months. Your results depend on your market and your case.

After: the follow-up

The plan works if you review it. Do this every month:

  • Set a 30-minute review for the first Monday of each month.
  • Review your 3 key numbers and the progress of each project.
  • If something is not moving, change the date or the owner, but don't let it die.

If you want a second opinion, the SBA (Small Business Administration) offers guidance and mentors to help you run your business.

What a normal month looks like after retirement

Imagine your first goal is to get paid every Friday. At the first Monday review, you look at how many invoices are still open and who has them. If three clients are behind, you assign one person to call them that week. That way the plan becomes a routine and not a forgotten sheet in a drawer.

Save each 1-page sheet with the date. Next year you can compare what you planned with what happened, and your next retreat will start with more information.

Common mistakes

  • Showing up without numbers and deciding by gut feeling.
  • Setting 10 goals instead of 3.
  • Not assigning owners or dates.
  • Review the plan only through next year.
  • Answering the phone all day.

What to do now

  1. Put the retreat date on your calendar.
  2. Ask your bookkeeper for your reports for the year.
  3. Print the agenda and the 1-page sheet.

FAQ

How often should I do a planning retreat?

For most contractors, it works well to take one retreat a year for the big plan. Then do a short review each quarter to see if you are on track and adjust dates, prices or owners before the year gets away from you.

Should I invite my team?

You can do the first part alone, which is reviewing your numbers and choosing your goals. Then invite your leaders, such as the supervisor or the office person, to set owners and dates. That way everyone understands the plan and commits to their part.

Which numbers should I track?

Bring the year's sales month by month, profit by type of job, accounts receivable and your monthly fixed costs. A list of your best and worst clients also helps. With that, you decide with data and not by gut feeling.

When to talk to a professional

This article is a general guide. If your case involves a letter from the IRS, the FTB or the EDD, a lawsuit, an accident or a change in your business structure, talk to a lawyer, a tax preparer (CPA or enrolled agent) or the official agency. Every case is different.

How ODC helps you

At Oficina del Contratista we keep your bookkeeping up to date: we record your income and expenses, reconcile your accounts and explain your reports in Spanish. For taxes, payroll, insurance or legal matters, we connect you with independent partners; they provide those services, not ODC. See all services.

Arrive at your retreat with your numbers ready. Message us on WhatsApp.

Message us on WhatsApp

References

  1. BDC – 5 steps to a successful strategic retreat — Steps to organize a strategic retreat
  2. SBA – Manage your business — Guidance and mentors for business owners
  3. Harvard Business Review – Vacation and well-being — Supports the value of disconnecting from work (source for the sidebar, not official)
Armando Ehrenzweig
Armando Ehrenzweig

Runs Oficina del Contratista, a Spanish-language bookkeeping service for contractors. Has experience in management, sales and construction consulting.

Important notice: this article is educational and informational only; it is not legal or tax advice. It may contain errors or be out of date. Before making decisions, check it with a licensed expert or attorney.