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How do you decide whether a tool belongs in your business?

Brett K Moore8 min readChoosing guide

Written for agents, brokers, lenders, contractors, home services.

The short answer

Sort every tool on two yes or no questions. Is it in the business right now, and should it be. Those two questions produce four boxes, and everything you pay for or are considering lands in exactly one of them.

The four boxes are keep, build, remove, and correctly absent.

Most buying decisions only ever use one box. Somebody names a gap, buys something to fill it, and nothing gets sorted into the other three. That is why stacks grow and never shrink.

The fourth box is the one that decides whether this is worth doing. Writing down what your business does not have and should not have is the only thing that stops the same conversation happening again next quarter.

Sort first, then rank by urgency. Ranking first fills the urgent list with work that never belonged on it.

Software gets into a real estate business the same way every time. Somebody hits a problem on a Tuesday. A coach, a peer at a mastermind, or the loudest person in a group chat names a tool that solves it. It goes on the card. Nobody ever takes anything off. Five years later a six person team is paying for four products that do the same job, two of which nobody has opened since the trial.

This is a method for sorting that out. It comes from a framework we use inside client work called sort and sequence, and the first pass of it is the part worth knowing on its own.

Two questions, four boxes

Write down everything under discussion. The things you pay for. The things that came bundled with your brokerage, your franchise or your lender platform. The thing somebody on your team signed up for with a company card. The things you are considering. Then ask two questions about each one.

  1. 01Is it in the business right now?
  2. 02Should it be?

Two yes or no questions give four combinations, and every item lands in exactly one of them. That is the whole mechanism. The value is not in the cleverness of it. The value is that it forces you to answer the second question about things you already own, which nobody ever does.

The four boxes

The same four boxes work on a single tool, on a whole stack, or on a list of nine requested changes to a website. Below they are described in general. Every tool article on this site ends with them filled in for one product.

There, and should be

It is in the business, it earns its place, and the correct action is to leave it alone.

  • The test is not whether you like it. The test is whether removing it would cost you something you can name.
  • A tool in this box still gets a review date. Things move.
  • Most of a working stack should be here. If almost nothing is, the problem is bigger than tooling.

Missing, and should be there

A real gap. Something the business needs and does not have.

  • This is the only box most people ever use, which is why the exercise usually ends in a purchase.
  • Write the gap as a job the business needs done, before naming any product that might do it.
  • A gap that has been open for two years without costing anything measurable is worth re-examining. It may belong in the fourth box.

There, and should not be

You are paying for it, or living with it, and it is doing nothing or doing harm.

  • The expensive version of this is two tools holding the same records, because now there are two answers to every question and one of them is stale.
  • A tool nobody opens is cheap. A tool half the team opens is what causes arguments about whose number is right.
  • Cancelling is one action. Getting your data out first is a different one, and it comes first.

Missing, and correctly missing

Something you do not have, that somebody keeps suggesting, and that you have decided against on purpose.

  • This box is the output of the exercise that has lasting value. The other three describe today. This one settles an argument in advance.
  • Each entry carries a reason, written down. Without the reason it gets re-proposed in ninety days by somebody who was not in the room.
  • A capability can sit here permanently, or until a condition changes. Name the condition when you know it.

What does the fourth box do that the other three do not?

It records a decision instead of a state. The first three boxes describe how the business is arranged today and go stale as soon as anything changes. The fourth box records a judgment about something you deliberately do not have, with the reasoning attached, so nobody has to rebuild that argument the next time it comes up.

This is also the box that shows whether somebody understands a product. Listing features is not hard. Anyone can read a comparison page. Naming what a tool leaves out on purpose, and being right that leaving it out was the correct call, takes having used the thing badly at least once.

It works on your own business the same way. A general contractor who has written down "we do not use a client portal, because our customers text and a portal is one more place they will not look" has settled that question. A contractor who has not written it down will hear it proposed at every trade show for the rest of their working life.

Running it in an afternoon

  1. 01Pull the list from your card statement, not from memory. Twelve months of charges. People are reliably wrong about what they are subscribed to, and the number of recurring charges nobody can identify is usually two or three.
  2. 02Add the things you were given. The platform bundled with your brokerage. The CRM that came with a lead contract. These cost nothing extra and take up the same space in a workflow as something you chose.
  3. 03Add the things on the wish list. Whatever somebody has been asking for. Whatever a coach told you to buy.
  4. 04Sort, one item at a time, out loud, with somebody else in the room. The second person is there to make you say the reason. A sort you do alone tends to confirm what you already wanted.
  5. 05Write the reason in the fourth box. One sentence each. This is the part that gets skipped and it is the part that makes the exercise worth repeating.
  6. 06Do not rank anything until the sort is finished. See below.

Then, and only then, rank by urgency

Whatever survived the sort gets a second pass, on a different question: how fast does this get worse if nobody touches it. Three answers.

UrgencyWhat it meansWhat it looks like in a real estate business
BleedingIt costs something today, every day.Buyer enquiries arriving at an address nobody monitors. A disclosure that is wrong on a live listing page.
DecayingIt gets worse the longer it waits, at a steady rate.A headshot from nine years ago. A CRM that has not been deduplicated since the last office move.
StableIt can sit. It will be the same problem in six months.A newsletter template you dislike. A reporting view that takes two extra clicks.

The order matters and it is the most common mistake. Rank first and the urgent pile fills with things that should have been refused in the first place. You end up moving fast on work that never belonged on the list, which feels like progress and is the opposite.

A worked example

This one is an illustration rather than a client. Take a contractor with three crews, doing kitchen and bath remodels, most of the work arriving through two agents who recommend him.

  • There and should be: the estimating software, the accounting package, the shared calendar the crews look at. Nothing to do.
  • Missing and should be there: one place where every promise made to a homeowner is written down. Right now those live in three phones and one truck. This is a gap stated as a job rather than as a product, which is the correct way round.
  • There and should not be: the second project management tool, bought last spring, which one crew lead uses and the other two do not. Two crews are on the shared calendar and one is in the tool. Nobody knows where a given job is without asking. This is the expensive kind of entry, because it is producing two answers to one question.
  • Missing and correctly missing: a customer portal. Reason: homeowners text this business, they will not log in to anything, and a portal would become a place work goes to be forgotten. Written down, with the reason, so the next salesperson who raises it gets a one sentence answer.

Four boxes, and only one of them is a purchase. That ratio is normal and it is the reason the exercise pays.

How often should you run this?

Once a year on the whole stack, and once on any single tool somebody is pushing you to buy. The annual pass takes an afternoon. The single tool version takes about twenty minutes and is worth doing before every demo call rather than after.

A demo is designed to fill in your second box for you. Running the sort first means you arrive with your own list of what is missing and can check the demo against it, instead of discovering three gaps you did not know you had while somebody shares their screen.

What this does not do

Where this came from

The four box sort is the first half of a framework we run inside client work, called sort and sequence. The second half is the dependency mapping: what has to happen before what, which pieces can run at the same time, and the one chain of dependent steps that sets the floor on how fast the whole thing can finish. That part matters when you are rebuilding something. The sort on its own is what most people need most of the time.

Every tool article in this library ends with the four boxes filled in for one product, including the fourth. If you disagree with what we have put in the fourth box for a tool you use daily, that is the useful kind of disagreement and we would like to hear it.

Common questions

What is the four box method for choosing software?
It sorts every tool on two questions: is it in the business now, and should it be. The four resulting boxes are keep, build, remove, and correctly absent. It is the first pass of a framework called sort and sequence, and it runs before any ranking by urgency.
Why sort before ranking by urgency?
Ranking first fills the urgent list with items that should have been refused. Sorting first means only work that belongs on the list ever gets prioritized. Sorting without urgency treats a problem costing money today the same as a nice to have, so both passes are needed, in that order.
What belongs in the correctly absent box?
Any capability your business does not have, that somebody keeps proposing, and that you have decided against for a stated reason. Each entry carries the reason in one sentence. Without the reason it gets re-proposed within a few months by somebody who was not part of the original decision.
Does this work for a solo agent as well as a team?
Yes, and it is faster. A solo agent typically has eight to fifteen items to sort and can finish in under an hour. The one part that does not shrink is the second person in the room, whose job is to make you state the reason out loud.
What is the most common finding when a team runs this?
Two tools holding the same records. That entry sits in the remove box and it is the most expensive kind, because two systems holding the same records produce two answers to the same question and neither one announces that it has gone stale.

Worth passing along

An agent, the lender she sends buyers to and the contractor she recommends are all running some version of this sort on completely different stacks. The list of tools has almost nothing in common. The four boxes are identical, which makes this one of the few pieces worth forwarding across the whole sphere rather than within one trade.

Written by Brett K Moore. We build the PAD System, a records structure for people, assets and deals that lives as plain text files on your own computer. Read what it is.

What should an AI stack for a real estate business have in it?

Seven layers, each one a job rather than a product, and the four box sort run across the whole stack at business level. Includes the send rule adopted after a private brief reached eighteen unintended recipients, and an honest account of what a built in fair housing check does and does not cover. Written for real estate agents, brokers, mortgage lenders and the trades who work alongside them.

What is Obsidian, and should a real estate business run on it?

Obsidian is a reader and editor for a folder of plain text files on your own computer. What that is good for in a brokerage, a loan branch or a crew, what it will never do for you, and the four box verdict. Written for agents, brokers, lenders and the trades.

Should your CRM be where your business remembers things?

A CRM is built to move people through a pipeline and it is very good at that. It is a poor place to hold what you know about a person, and the two jobs pull against each other. Where the line sits, and the one rule that stops the two systems disagreeing. Written for real estate agents, brokers, mortgage lenders and the trades who work alongside them.