HotDocs conversion project: why it is really two projects

Ask a firm what it wants from a HotDocs conversion project and the answer is usually simple: move the templates across, change nothing, keep working. It is a reasonable request, and it is almost never what the firm ends up doing.

About three weeks in, someone opens a template that has not been run since 2019 and the conversation changes. Half a dozen templates turn out to be near-duplicates. A clause was superseded by legislation two years ago. Three variations exist because a partner wanted them and that partner has since retired. At that point the firm is no longer converting templates. It is reviewing its precedent library — worthwhile work, but not the project that was scoped, resourced or approved.

A conversion contains two distinct pieces of work: converting the templates and modernising them. One is largely mechanical, and software does it well. The other is a design exercise that needs experienced document architects and authors, and takes considerably longer. This post separates the two so you can decide how much of each you want — before the project decides for you.

The two jobs inside a HotDocs conversion project

It is worth being precise about the difference, because the two jobs have different owners, different effort profiles and different definitions of done.

• Conversion is translation. You take the templates you have and make them run on the new platform, producing the same document from the same inputs. Success is measurable: regenerate a document the old system produced, with the same data, and compare. It is bounded, testable, and mostly automated.
• Modernisation is design. You decide what the library should look like now — which templates survive, how the questions are sequenced, which language becomes shared and governed, and which old workarounds can finally be retired. Success is a judgement call, not a comparison.

Scoped and budgeted as one line item, the second job quietly absorbs the first. That is the most common reason conversion projects overrun, and it has very little to do with the software involved.

What conversion covers, and why it is the easier half

The free HotDocs Classic converter does the mechanical work. It translates the fields in your templates into XpressDox equivalents, generates the interview and the underlying scripts from your component files, and — importantly — flags the constructs it cannot translate faithfully rather than guessing at them. Simple templates, which in most libraries means a good proportion of the letters, notices and short-form agreements, often need little or no attention at all.

The converter is free, as is the equivalent tool for Contract Express. Both handle basic and moderately complex templates; sophisticated suites with heavy computation logic are work our implementation partners do routinely. The point is that this half of the project behaves itself. Effort scales with how complex your templates are and how consistently the original author named things — not with the number of templates. It is testable, it is repeatable, and it gets faster as it goes.

If your only objective is to leave HotDocs Classic with the library you already have, conversion is most of the project. Very few firms stop there.

Why almost every firm ends up modernising as well

A template library is a record of decisions taken over ten or fifteen years, on a platform with its own constraints, by authors who have often moved on. A conversion is usually the first time in years that anyone reads it end to end. Four things surface reliably:

1. Dormant templates. A long tail last used years ago, still carried, still counted in the estimate.
2. Drift. The same clause in five wordings across five templates, because each was amended separately.
3. Workarounds. Structures that exist only because the old platform could not do something the new one can.
4. Quiet obsolescence. Content that no longer reflects current legislation, or the firm’s current position.

None of this is unique to HotDocs, and none of it reflects badly on the firm. The Legal Practitioners’ Liability Committee recommends reviewing precedents every six months and lists outdated precedent letters and staff-modified versions among its recurring claim patterns — which tells you both that the risk is real and that the recommended cadence is one very few libraries actually manage.

The reasons are structural rather than a lack of will. Ken Adams has written that “the landscape is littered with the rusting hulks of law-firm template initiatives”, and puts it down to billable-hour incentives, unclear ownership and the fact that deal experience does not automatically make someone a good template designer. A conversion is one of the few moments when this work gets both attention and a budget. So the instinct to modernise during a conversion is the right instinct. The difficulty is timing and resourcing, not motive.

💡 Insight
It is worth running a usage report before you scope anything. Firms often find that a meaningful share of the library has not been generated in years, and the templates still in daily use are a much shorter list than the folder suggests. Every dormant template you retire is one you do not convert, do not review and do not maintain — the cheapest scope reduction available, and it costs an afternoon.

Modernisation is a different kind of work, done by different people

Conversion is a translation problem, and software is good at translation. Modernisation is a design problem, and it needs people who have designed a lot of libraries. The work usually includes some combination of:

• Rationalising the library — retiring, merging and consolidating rather than carrying everything across.
• Restructuring the interview so questions follow the order a lawyer actually works in, rather than the order the old dialogs happened to be stored in.
• Moving repeated language out of individual templates and into a governed clause library, so a change is made once and inherited everywhere — the precedent management problem most libraries are quietly carrying.
• Connecting the templates to the document and practice management systems so client and matter data is captured once and reused, instead of retyped.
• Rebuilding complex logic properly, rather than living with a literal translation of how it was expressed fifteen years ago.

Two things follow from that list. First, the skills are different: this is work for experienced document architects and authors with an opinion about what good looks like, not something a converter can be asked to do. Second, the effort is far less predictable. A converted template can often be reviewed in minutes. A redesigned one takes hours, sometimes days, and needs a fee earner to agree the drafting before it can be signed off.

💡 Insight
The bottleneck in a modernisation programme is rarely authoring capacity — it is partner time. Someone has to approve the wording that will now be used firm-wide, and that approval competes with billable work. Firms often find it helps to agree in advance who signs off drafting changes for each practice group, and to give them a small, batched set of decisions rather than a running stream of questions.

Deciding how much to modernise

The useful framing is not “convert or modernise” but “how much of each, and for which templates”. Sorting the library into three buckets makes the decision manageable:

1. Convert as-is. High-volume, stable templates whose content is current and whose structure works. This is normally the bulk of the library, and it should move across like-for-like.
2. Convert, then tidy. Templates that work but sit awkwardly — question order, duplicated lists, clauses that should be shared. Small improvements made during the review pass, at very little extra cost.
3. Redesign. The oldest and most heavily amended templates, anything with dense conditional logic, and anything where the law or the firm’s position has moved. Small in number, large in effort.

Four questions sort a template into a bucket quickly: how often is it used, what is the consequence if it is wrong, how often does its content change, and does the drafting still reflect what the firm would say today? A property transfer generated three hundred times a month and a bespoke facility agreement used twice a year belong in different buckets, whatever their relative complexity.

💡 Insight
It is worth converting one representative template suite before estimating the whole library — and choosing a typical suite rather than an easy one. Firms often find the ratio of clean conversions to review-needed conversions holds reasonably steady across a library, so an honest sample projects far better than a template count. It also shows you where your redesign bucket really is.

Sequencing the two jobs so they do not collide

Our consistent recommendation is to keep the two jobs as separate stages, with separate sign-offs, in this order:

1. Audit and run a usage report. Decide what is in scope before anything is converted.
2. Convert one representative suite and verify it against documents the old system produced.
3. Convert the remainder like-for-like, resisting the temptation to improve as you go.
4. Run in parallel while a practice group confirms the output in live matters.
5. Modernise in waves, practice group by practice group, once you are off the old platform.

The reason is simple. Leaving the old platform is time-bound; reviewing a precedent library is not. Couple them and the platform move waits on a partner’s decision about a clause — which is how a six-week conversion becomes a six-month programme with nothing live at the end of it. Decoupled, the conversion finishes on schedule and the library improves continuously afterwards.

Modernising second is also better informed. By then you have read the whole library, you know where the effort concentrates, lawyers are already using the new interview and can tell you what actually annoys them, and every improvement lands on a platform that will still be there in ten years.

Common mistakes in a HotDocs conversion project

Five patterns account for most of the overruns we see, and all five are avoidable.

1. Budgeting for the translation and discovering the review. The estimate covers converting templates; the work that appears is library review. Budget for both, or explicitly defer one.
2. Fixing the modernisation scope before seeing converted output. You cannot sensibly decide what to redesign until you can see what came across cleanly and what did not. Convert a sample first, then scope.
3. Modernising everything at once. A whole-library redesign needs sign-off from every practice group simultaneously, which is the one thing a busy firm cannot supply. Waves work; big bangs stall.
4. Converting templates nobody uses. Without a usage report, the dormant tail is converted, reviewed and maintained alongside everything else, for no benefit.
5. Treating library review as housekeeping. It is risk management. The templates that go out most often are the ones least likely to be read carefully, which is precisely why outdated precedents turn into claims.

Our view: convert like-for-like, then modernise deliberately

Both jobs are worth doing. Firms that convert and never modernise carry fifteen years of accumulated compromise onto a modern platform, and firms that try to do both at once frequently do neither. Our position is that the mechanical translation is the part worth automating, the design review is the part worth a person, and vendors who blur the two do firms no favours. That is also why we give both converters away: the migration barrier, rather than any software comparison, is what keeps firms on a platform they have already outgrown, so removing it is more useful to us than charging for it.

It follows that a converter buys you time, not a finished library. Anyone describing a conversion that hands back a modernised, rationalised, governed library is describing a translation and calling it a redesign. HotDocs has been in this market since 1993, and the firms running it built genuine institutional knowledge into those templates — drafting decisions, jurisdictional variations, hard-won edge cases. A conversion should carry that knowledge into Advanced Document Automation intact, and then improve it on purpose rather than by accident.

Where to start

Two pieces of work this month will tell you more than any proposal. Run a usage report, so you know how large the library really is. Then convert one representative suite and review it properly, so you know your real conversion ratio and roughly how big your redesign bucket is. With those two numbers you can scope the conversion and the modernisation separately, and decide which one you want to run first.

If you would rather work through it with people who have done this many times, book a discovery call and bring the usage report. We will be candid about which parts of your library are a conversion and which parts are a redesign.

Frequently asked questions

Is a HotDocs conversion project the same as modernising our templates?

No — they are two separate pieces of work. Conversion makes your existing templates run on the new platform and produce the same documents. Modernisation decides what the library should look like now: what to retire, how to restructure the questions, and which language should be shared and governed. Most firms need both, but they should be scoped, resourced and signed off separately.

Can the converter modernise our templates for us?

No, and that is deliberate. The converter translates what is there; it does not make design decisions about your drafting. Where it meets something it cannot translate faithfully it flags it for review rather than guessing, which is the behaviour you want in a tool handling documents that go out under the firm’s name. Modernisation is work for experienced document architects and authors.

Should we modernise before or after converting?

After, in most cases. Leaving the old platform is time-bound; reviewing a precedent library is not, so coupling them lets library decisions hold up the migration. Converting first also gives you better information: you will have read the whole library, and your lawyers will be using the new interview and able to tell you what needs changing.

How much of our library will convert without changes?

It varies by library, and the honest answer is that you should measure rather than take an average. Templates whose fields hold nothing more than a variable name often need very little attention, while templates with dense conditional logic or computations need review. Converting one representative suite gives you a far better projection than a template count.

Do we need outside help for a conversion?

It depends on the complexity of your templates rather than the size of your firm. The free converters handle basic and moderately complex HotDocs Classic and Contract Express templates, and many firms run that stage themselves. Sophisticated suites, and most modernisation work, are where our implementation partners add the most value.