How I got my kids to beg for strategy planning

October 26, 2025•7 min read

Last week I did something that should've been a disaster.

I combined my quarterly off-site planning with a family vacation.

And instead of my wife rolling her eyes at me working through vacation and my kids complaining about dad disappearing for "business stuff"—they're asking when we can do it again.

I walked away with absolute clarity on our next 12 weeks at MSP Sales Partners and Repeatable Revenue. And a family that's suddenly invested in strategic planning.

Here's the framework I used in case you want to steal it.

The Two Things That Make This Work

Before I get into the how, you need to understand the why.

Because without this context, the rest of this won't make sense.

I run my business based on two core principles:

1. Constraints Theory

Your business is a chain. It's only as strong as its weakest link.

Constraints theory says that until you fix that weakest link, improving anything else is just polishing the parts that weren't breaking in the first place.

Think about it: If your biggest problem is lead quality, building the world's best onboarding process is a waste of time. If your constraint is delivery capacity, perfecting your marketing funnel just creates more backlog.

So we focus most of our resources on removing ONE constraint to get the highest return on effort.

2. Steady Cadence

We don't set it and forget it.

We run a 12-week planning cadence with a 6-week check-in. This ensures we're frequently identifying constraints, confirming we're working on the right one, and allocating all available resources to removing it.

Because constraints change. What's blocking you today won't be what's blocking you in 90 days.

Now here's how I actually run the planning process.

The Week Before the Offsite

Step 1: Set the date, time, and location

Pick a fun place to post up for a handful of days. My wife handles the logistics, so I can't give you a play-by-play on how to do this. But it's a little easier for us since we live in Cabo.

It doesn't have to be an international resort though. Just needs to be somewhere you can focus for the first couple days and the family will enjoy for the next few.

Step 2: Identify the primary constraint

This is the most important part. Get this wrong and everything else is wasted effort.

I do this two ways:

Poll the team. What do they think is the single biggest constraint? Not just in their direct responsibilities—for the business as a whole. The one thing that, if removed, would move us forward the most or fastest.
Do a quick audit. Is this a demand problem (not enough sales) or a supply problem (delivery is broken)?

If it's demand: Not enough leads? Poor lead quality? Low conversion?

If it's supply: Capacity issue? Quality of service problem?

These are different problems with different solutions.

I compare my diagnosis with the team's and determine what the single biggest bottleneck actually is.

Step 3: Gather all potential solutions

I pull up a note I have saved on my phone called Ray's Big List of Ideas. It’s all the ideas I've had that I haven't bothered sharing with the team because I knew they'd be a distraction.

I look for ones that address the primary constraint and add them to the list.

Then I dig through our "parking lot"—ideas we said no to throughout the last sprint. Again, looking for anything that addresses the core constraint.

This way, I'm walking into planning with:

Clear understanding of the problem
All solutions we already have on deck

At the Offsite

Step 1: Re-confirm the constraint

I revisit the core constraint with fresh eyes.

Do I still believe this is the single biggest problem to solve?

Once I'm committed (or recommitted), I move forward.

Step 2: Review and refine the solutions list

I take the list of ideas I brought with me and spend time brainstorming.

Anything else that should be added? Anything that should be removed because it's not feasible or not the best solution to the biggest problem?

Step 3: Score the finalists

This is where most planning falls apart—picking what to work on.

I use a model I stole from the software company Intercom and adapted for my business. It’s called RICE (Reach, Impact, Confidence, Effort) and prioritizes which software updates and features to work on.

It's a perfect methodology to use for prioritization because one of the biggest risks for software companies is complete dilution of effort since they have an infinite number of features they could build with endless customer requests.

In other words, prioritization is essential in a software company.

I dropped the "R" and use ICE:

Impact – How much will this affect the core bottleneck? (Minimal / Low / Medium / High / Massive)
Confidence – How confident am I this will work? (50% to 100%)
Effort – How many man-hours would it take one person to implement this if they were 100% focused?

I score each idea on these three factors. The calculation gives me a prioritized list.

I copied Intercom's calculation for weighting each of these three factors. Don't worry about the underlying math—I have a calculator set up as a Google Sheet that you can make a copy of here.

Step 4: Common sense check

I look at the scores and evaluate from a common sense standpoint.

Does this pass the sniff test?

Step 5: Evaluate bandwidth

Do we have the bandwidth to do one of these things? Two? Three?

If it's more than three, I'm probably underestimating effort (which I'm notorious for doing). So I go back and break down what's really entailed in getting each one done to keep myself honest.

Step 6: Assign ownership and define done

For each priority, I assign tentative ownership and define what "done" looks like in a sentence or two.

Now I have our core priorities for the next sprint.

Step 7: Welcome the family

I wrap up my planning and welcome the family.

We spend the next few days at the pool, drinking margaritas and Shirley Temples, lounging, and getting in good family time.

Zero guilt. Zero second-guessing. Because I know exactly what we're focused on when I get back.

I wrap up my planning and welcome the family.

We spend the next few days at the pool, drinking margaritas and Shirley Temples, lounging, and getting in good family time.

Zero guilt. Zero second-guessing. Because I know exactly what we're focused on when I get back.

Back at the Office

Once I'm back, we meet as a team.

I summarize:

The priorities
My thought process
Tentative ownership
Definition of done

Then I invite debate, disagreement, discussion.

We iterate or commit, lock it in, and execute.

We check in on progress halfway through the quarter and re-evaluate.

Is It Perfect?

Of course not.

But it does ensure we're focused on the single most important problem in the business. It keeps us realistic about our bandwidth. It makes the core focus crystal clear. And it has flexibility to iterate as we go.

Equally important?

I have an accountability system that's incentive-based to maintain this process.

And my family loves strategic planning.

Make It Work For You

If you want to try this:

Before your offsite:

Pick a location the family will enjoy
Poll your team on the biggest constraint
Do your own audit (demand vs supply problem)
Gather all the ideas you've been sitting on
Review the parking lot from last quarter

At your offsite:

Confirm the core constraint
Score your ideas using ICE
Be realistic about bandwidth (if it's more than 3 priorities, you're lying to yourself)
Assign ownership and define done
Welcome the family and enjoy yourself

When you're back: