The 15 Biggest Challenges Training Companies Face (What We Hear on Calls)

The biggest challenges training companies face have almost nothing to do with training. Through 2026 we have been sitting down with the people who run them, operations directors, heads of delivery, founders and CEOs, and asking one question: what is making it hardest to deliver training and grow the business? The same answers kept coming back. An instructor bench nobody can see. A schedule that lives in a spreadsheet. An LMS that never touched live delivery. Margin that only shows up after the class is over.

Before TryTami we ran DevelopIntelligence, a technical training company with a few hundred instructors on the bench, until Pluralsight acquired it and we spent a few more years running instructor-led training inside it. A fair number of the problems below were ours first. We recognized most of them the moment people started describing them.

Between them, these training providers deliver instructor-led training across an enormous range, from around a hundred sessions a year to well over ten thousand. The subject matter varied as much as the scale: technical and IT training, sales and leadership development, compliance and certification, skilled trades, workforce and career programs, finance. Some sell dedicated training to enterprise clients under contract. Some sell open-enrollment seats to whoever registers. Most do both, which is its own complication.

What surprised us was how little the differences mattered. A company running a hundred classes a year with twenty contract instructors described the same training operations problems as one running thousands of sessions across three continents. Same bottlenecks, different order of magnitude.

So we went back through the notes and counted. Below are the fifteen challenges these training companies named most often, ordered by how many raised each one without being prompted. For each one we have added what it actually costs, because every item on this list eventually shows up as lost revenue, unnecessary cost, or hours of manual coordination somebody is being paid for. This is not a market survey and we are not pretending otherwise. It is what a room full of operators told us was hard, in the order they told us.

Nobody we spoke to was confused about how to teach, and nobody was short of demand. What held them back was the coordination underneath delivery, and it was costing them twice: once in the hours it eats, and again in the growth it quietly caps.

The 15 challenges, in order

1. A mixed bench of contractors and employees, managed in pieces
2. Spreadsheets and calendars are the real system of record
3. Working out who is actually qualified
4. The LMS they bought does not touch instructor-led delivery
5. No view of instructor utilization or capacity
6. The same data entered three or four times
7. Running training operations out of a CRM
8. Participant communications are a person, not a system
9. Cost and margin per class are invisible until after delivery
10. Same volume, smaller team
11. Instructor availability lives in email
12. Nobody outside operations can see the schedule
13. Evaluations quietly stopped working
14. Global operations siloed by region
15. Rooms and equipment get double-booked

1. A mixed bench of contractors and employees, managed in pieces

Almost every company we spoke to raised this one. The instructor bench is hardly ever all employees. It is a core of full-time staff surrounded by contractors, associates, former staff who still take work, and trainers supplied by partners. One company ran ten. Another ran several hundred across three continents.

The pattern held at every size. Rates live in one place, skills in another, certifications in a third, and how good someone actually is lives in a scheduler's head. Nobody we spoke to had a single record of an instructor. Several had built one by accident, in a spreadsheet, and it was already out of date. The practical cost is that no staffing decision can be made in one place, and the person who has done the job longest becomes a dependency. More on the lifecycle in how to manage hundreds of instructors.

What it costs: overhead and key-person risk. Every staffing decision needs three or four lookups, so coordination time scales with volume instead of flattening. And because the knowledge sits with whoever has been there longest, you cannot add a coordinator without months of shadowing, and you cannot afford to lose that person.

2. Spreadsheets and calendars are the real system of record

Roughly two thirds were running training operations out of spreadsheets, shared calendars, or a general-purpose project board never designed for training delivery. This held true for companies with real software budgets and companies with sophisticated systems elsewhere in the business. The schedule simply lived somewhere else.

One operations leader estimated a single scheduling cycle consumed 400 to 600 hours of director time. Another described their training operation as running "on hopes and prayers," using their software as a ledger rather than a tool. A third was maintaining the same information in a project board and a separate database at the same time. We wrote about why this persists in why training providers still run on spreadsheets.

What it costs:hours, in salary. 400 to 600 hours of director time per scheduling cycle is a meaningful share of a senior person's year spent on coordination rather than on selling or improving delivery. Spreadsheets also fail silently, so the errors surface as a double-booked instructor or a class nobody staffed, and those get fixed with apologies.

3. Working out who is actually qualified

More than half described the same difficulty: deciding who is genuinely right for a course, not just who holds the certification. The filters people wanted were specific. Certifications and credentials. Client history, because a client often asks for the instructor they had last time. Industry background. Language and time zone. And audience level, whether someone is right for early-career staff or for executives, which several treated as a completely separate attribute from technical skill.

None of that was in one place. One scheduling team was finding specialist instructors by keyword searching a folder of resumes in a word processor. When the person who knows the bench is on vacation, the work slows down. See AI instructor matching for how we think about this.

What it costs: revenue you win more slowly, and delivery quality you cannot predict. Every hour spent searching resumes is an hour a client waits for an answer. Worse, when the search is manual, people default to whoever is easy to remember, which is how the wrong instructor ends up in front of an executive audience and a renewal quietly disappears.

4. The LMS they bought does not touch instructor-led delivery

Just under half had adopted an LMS, at real expense and after a long implementation, only to find it did nothing for the part of the business that was actually hurting. One leader in the middle of selecting a new LMS told us plainly that it does not help the instructor-led side. Another was running self-paced content and student communications through theirs while the entire live delivery operation ran on spreadsheets next to it.

The complaint was rarely about the software itself. It does what it does, and most had no intention of replacing it. The complaint was about what it cost to find out. These are not cheap systems. Larger providers spend up to $250,000 a year on an LMS, the license renews whether or not it touches instructor-led delivery, and the implementation consumes months of internal time before anyone discovers the gap.

And after all of it, staffing a class, confirming a trainer and chasing a roster were exactly as manual as before. Several told us they only discovered the gap once the implementation was finished and they went looking for the scheduling features.

What it costs: a line item reaching up to $250,000 a year that does not touch the problem. The license renews whether or not it helps live delivery, the implementation consumed months of internal time, and the manual scheduling work carried on underneath it the entire time. Several teams paid twice: once for the LMS, and again in the coordinator hours it never removed.

5. No view of instructor utilization or capacity

Just under half raised some version of this. It is really the consequence of the first two: if the bench is managed in pieces and the schedule lives in a spreadsheet, nobody can see how loaded an instructor is until something breaks.

The sharpest example we heard: a sales leader whose best trainer had no availability for four months, with no way to see what she was committed to or why, while clients asked for her by name. On the other side of the same problem, several teams were rebalancing load by hand because some instructors were overworked and others sat idle, with no capacity view to plan against. We go deep on the metric in instructor utilization.

What it costs: margin, directly. You are paying for instructor capacity whether or not it gets sold, so every point of unused capacity is gross margin you have already spent. At the other end, the instructors who are quietly overloaded are the good ones, and replacing a strong trainer who burns out costs far more than the schedule that broke them.

6. The same data entered three or four times

Around half were re-keying the same information across systems that do not talk to each other. A request arrives in one place. Someone copies it into a form. Someone moves it into a spreadsheet. Someone enters it again into the LMS and the calendar. One organization walked us through nine or more manual steps to enroll a single student across four systems.

The cost is not only the hours. It is that nothing is authoritative, so reconciling the versions becomes its own recurring job, and every handoff is a chance for a date or a name to drift.

What it costs: paid hours, and rework. The re-keying itself is coordination labor you are funding on every single enrollment. The bigger cost arrives later, when two systems disagree about a date or a roster and someone spends an afternoon working out which one is right, usually after a student has already turned up at the wrong time.

7. Running training operations out of a CRM

Roughly two in five were running some or all of training delivery inside their CRM. Sometimes that meant a custom module built years ago by a developer who has since left. Sometimes it meant courses modelled as products and classes modelled as opportunities, which works right up until it does not.

This is a different problem from the spreadsheet one. The CRM is usually a real system, properly maintained, with an administrator looking after it. It is just the wrong shape for training.

Data ends up scattered across objects that were never designed to hold a session, a roster or an instructor rate. The interface is built for a sales pipeline, so schedulers click through screens that have nothing to do with their job. And because the CRM cannot quite do what is needed, somebody fills the gaps by hand. That is where the hours go.

One leader told us plainly that their CRM was their single biggest pain point and that replacing it was the priority. Another was in the middle of retiring a home-built events module inside theirs.

What it costs: hours every week, plus the money already going into the CRM. You pay for licenses, an administrator and customization work on a system that will never quite fit training delivery, and then you pay again in the manual workarounds that fill the gaps it leaves.

8. Participant communications are a person, not a system

Registration confirmations, joining instructions, reminders, pre-work, certificates, follow-ups. A similar share were sending some or all of this by hand, and a couple named the coordinator role explicitly as the thing they wanted to stop paying for.

The failure mode is predictable and expensive. One company changed a class's time zone, no notification went out because notifications were manual, and students joined at the wrong hour. Another pointed out the upside nobody was capturing. The post-course email is the natural moment to recommend the next course, and when a human is sending it, it never happens consistently.

What it costs: a headcount you may not need, and revenue you never see. Manual communications are effectively a coordinator salary spent on sending email. Meanwhile the post-course follow-up is the single easiest upsell in the business, and when a person has to remember to send it, most of that revenue simply never happens.

9. Cost and margin per class are invisible until after delivery

A third wanted something their systems could not give them: what did this class actually make? Contractor day rates ran from roughly $1,000 to $2,000 a day against fixed client budgets, and reconciling delivery cost against a purchase order was a manual exercise done after the fact, if at all.

The asks were specific. Margin percentage next to revenue at the course level. Cost overrides per client. Burndown against a large committed contract using each assigned instructor's real rate. Full cost including materials, travel and room hire, not just instructor fees. Without it, the decision to accept a date or assign a particular instructor is made blind to what it does to the margin. See operations intelligence.

What it costs: margin you cannot recover, because you find out too late. At $1,000 to $2,000 a day for contract instructors, one assignment made without visibility can take a class from profitable to underwater, and you learn about it after delivery. Priced blind and repeated across a year of classes, this is the most expensive item on the list.

10. Same volume, smaller team

A third of these training companies were explicitly trying to deliver the same amount of instructor-led training, or more, with fewer coordinators. One scheduling team had been cut in half and still covered thousands of sessions a year. That changes what a team values. Marginal efficiency, saved clicks and fewer lookups matter more than new capability when two people are doing the work of four.

One CEO was refreshingly direct that he wanted to reduce headcount. Most framed it as running more training with the same team. It is the same objective.

What it costs: a hard ceiling on growth. When coordination capacity is the constraint, taking on more work means hiring more coordinators, so revenue and overhead rise together and margin never improves with scale. In the meantime the existing team absorbs it through weekend work, which has its own turnover cost.

11. Instructor availability lives in email

A quarter described instructor scheduling as two separate jobs, and this is the second one. Once you know who could teach the course, you still have to find out whether they are free, and for most training providers that means writing to them and waiting.

Offers go out by hand. Confirmations come back by hand, or do not come back and get chased. Contractors often will not connect a calendar to a client's system, so their availability exists only in their own head until somebody asks.

One team was keeping availability in two places at once, entering it into a scheduling tool and a calendar separately. Another said getting a bench of a few hundred associates to keep any shared calendar current was the hardest adoption problem they had. Every one of those exchanges is a delay between a client asking for a date and getting an answer, and clients notice.

What it costs: deals, on speed. A client asking whether you can run a course in three weeks is a buying signal, and the answer sits behind a round of emails to contractors who may not reply for days. Competitors who can answer that same afternoon win work on responsiveness alone, without ever being better at training.

12. Nobody outside operations can see the schedule

A handful raised visibility as a problem in its own right. Program managers locked out of the scheduling data they needed. No view across sites, regions or teams. Answering a routine question, such as which instructor is on which course, or where a student is meant to be this afternoon, meant asking a person and waiting for a reply.

The knock-on effect people described was sales being cut off from delivery. Sellers cannot see what capacity exists, so they promise dates operations cannot staff, or they hold back on selling because they cannot tell what is possible. The schedule ends up as private knowledge held by two or three people, and every other team routes around it. One company wanted a shared dashboard specifically so operations, customer success and sales could stop interrupting each other.

What it costs: revenue at both ends. Sales promises dates operations cannot staff, which turns into rescheduling and an unhappy client. Or sales holds back because nobody can confirm capacity, and you leave work on the table that you could have delivered comfortably. Both are expensive, and the second one is invisible.

13. Evaluations quietly stopped working

A handful had an evaluation process that had degraded to almost no response. In one case a change to the delivery process removed the in-session prompt and completion collapsed. Others were running evaluations through a separate survey tool disconnected from the roster, so linking feedback back to an instructor or a course meant manual work nobody had time for.

This matters more than it looks. Feedback is how you learn which instructors are strong with which audiences, which is the input you need for the qualification problem further up this list. When evaluations stop, that knowledge stops accumulating, and you are back to relying on whoever remembers.

What it costs: the data you need to protect quality and renewals. Without feedback you cannot tell which instructors are strong with which audiences, so matching gets worse over time rather than better. You also lose the evidence clients ask for at renewal, which turns a straightforward conversation into a defensive one.

14. Global operations siloed by region

A handful ran training across multiple countries with no shared system. Each region had its own process, its own spreadsheets and its own workarounds, so the same work was done repeatedly and nobody had a consolidated view. One operations director described doing identical tasks several times over because no country's process talked to another's. Data residency requirements added a further constraint for European operations. Related: global training delivery.

What it costs: duplicated overhead. Each region carries its own coordination burden, so you are funding the same manual process several times over instead of once. It also removes any consolidated view of capacity or margin, which means pricing and resourcing decisions get made region by region with no picture of the whole business.

15. Rooms and equipment get double-booked

A couple of companies raised this one, and for anyone delivering in person it is a real operational headache. Physical classrooms are a finite resource and they usually sit on a different calendar from the instructors, so the two drift out of sync and a room ends up promised to two classes on the same morning. Sorting it out means a phone call to a client.

The same applies to kit. One company was shipping equipment out to venues for public courses and tracking it separately from the schedule, which means a class can be fully staffed, fully booked, and still missing the thing it needs to run.

What it costs: classes that do not run, and the client call that follows. A room double-booked or a shipment that misses a venue means rescheduling a session that was fully staffed and fully sold, so you carry the instructor cost and the shipping cost without the revenue, and the client remembers it.

What the list adds up to

Read it in order and one story emerges. The bench is fragmented, so the schedule goes into a spreadsheet or a CRM built for something else. Because the schedule lives there, qualification is a manual search, availability is an email thread, utilization is invisible and margin can only be reconstructed afterwards. Because none of it is connected, the same data gets entered repeatedly, communications depend on somebody remembering, and everyone outside operations has to ask.

Add up the costs itemized above and the shape of the problem changes. It stops being a set of annoyances and becomes a P&L item: coordinator salaries funding manual data entry, senior time spent on scheduling instead of selling, instructor capacity paid for and never sold, an LMS renewing every year without touching delivery, and classes rescheduled at your cost.

The growth cost is less obvious and probably larger. When nobody can see capacity, sales either promises dates that cannot be staffed or holds back on selling. When margin only appears after delivery, pricing is guesswork. When the bench is invisible, the answer to a client asking for a date takes days instead of minutes, and the answer to whether you can take on more work is a shrug. Several of the companies we spoke to were not short of demand at all. They were short of the ability to say yes to it quickly.

None of this is a training problem. Every training company on this list was good at delivering training. What they were struggling with was the training operations underneath it, usually run on tools adopted for some other purpose entirely.

If several of these sound like your week, you are not unusual. Most training providers we meet recognize at least half the list. If you want to compare notes on how you are handling any of the fifteen, we are always up for that conversation, and we are still learning what this looks like at different sizes. If you would rather read about the category of software built for instructor-led delivery, a training management system rather than an LMS, we cover that in the best training management software.