I’ve been passed over by training organizations more times than I care to count. The resumes they choose tend to have certifications I don’t have, like Microsoft Certified Trainer or Microsoft Office Specialist. The resumes they pass on sometimes include things I do have, like Microsoft MVP status, a couple of O’Reilly books, a LinkedIn Learning course library with hundreds of thousands of learners, and years of corporate training delivery at companies most people would recognize.
That gap used to bother me a lot, and honestly it still bothers me some. But I’ve come to understand what’s actually happening on the other side of the table, and once you see it, you can work with it.
Training orgs sell predictability, not excellence
The first thing to understand is what these organizations actually sell. Most of them place instructors into corporate training engagements, and the corporate buyer wants a safe, repeatable, defensible choice. Certifications like MCT and MOS act as a checkbox that procurement can point to. If something goes sideways in the engagement, the vendor says the instructor was certified to the Microsoft standard. Nobody gets fired over that decision.
Your own credentials might represent a higher level of work. They probably do. They’re also less templated, and that makes risk-averse buyers uneasy. It makes the org placing you uneasy too. They aren’t really evaluating who teaches best. They’re evaluating who is the safest person to put in a room with a paying client.
The MVP paradox
This is where the Microsoft MVP award runs into trouble. MVP reflects sustained contribution and recognition in the field. MCT and MOS are standardized credentials designed to signal baseline capability. Microsoft renews it annually, and renewal depends on sustained, demonstrated community contribution across the year. It’s a recognition of work in the field, not a formal teaching credential.
Procurement teams don’t always know that. What they know is that MCT has “Trainer” in the name. MOS has “Specialist.” MVP is unfamiliar, which makes it feel squishy even when the bar is much higher. So the more elite credential loses to the more standardized one because the more standardized one is easier to defend to a budget committee.
Live classroom versus recorded content
Another piece of the puzzle is how these orgs think about live delivery. Books prove depth. Recorded courses prove clarity. Neither one, in their view, proves you can hold a live room together.
They have specific concerns. Can this person handle interruptions? Can they adjust pacing when half the room is ahead and half is behind? Can they manage a disengaged group, a confused group, or a group where the wrong software is installed on everyone’s machines?
Those are fair questions on the surface. The problem is that plenty of us with large recorded libraries have also done heavy live work. We just haven’t packaged it the way these orgs want to see it.
Employee thinking, applied to contractors
When you’re a full-time employee, you sort of expect this dynamic. An employer looking at someone with an outside audience, a body of published work, and a deep network often sees those things as a kind of flight risk. The worry is that you’ll leave, or moonlight, or bring your own brand into their engagements instead of theirs. Not every employer thinks this way, but enough do that it’s a known phenomenon, and most of us have lived through some version of it.
What’s harder to anticipate is how often training orgs hiring you as a contractor think the exact same way. On paper, a contractor relationship should be the one place where distinctive expertise and an outside platform are treated as pure advantages. You aren’t in the org chart. They’re paying you to come in, do a specific thing on a specific day, and go home. Being you, with all of your reach and reputation, should be the whole reason they picked you.
In practice, a lot of these orgs want contractors they can treat like employees. Standardized, de-riskable, and invisible outside the engagement. The same instinct that makes a hiring manager nervous about a candidate’s public profile shows up on the contractor side too, just with a different vocabulary. The fact that you’re independent doesn’t automatically earn you credit for being independent. Worth knowing going in, because it changes how you read these conversations.
One quick note before getting tactical. I don’t naturally optimize for certifications or exams. Most of my learning has come from building things, teaching real groups, and being in the work day to day. That path compounds differently. It produces depth and adaptability, but it doesn’t always show up as clean checkboxes on a resume.
The catch is that training orgs do evaluate through those checkboxes, so you have to translate what you’ve built into something legible on their side.
How to translate what you’ve built into what they buy
Here’s where the post turns useful, because the frustration is real and the workaround is fairly straightforward. You have to meet them where they evaluate, not where you are.
Start with live delivery evidence. Count the webinars you’ve hosted, the live cohorts you’ve run, and the conference sessions you’ve delivered. Put numbers on all of it. If you’ve taught a live session with forty attendees and handled active Q&A, that’s a classroom. Frame it that way. Something like “I’ve delivered X live sessions to Y attendees across Z years” speaks their language in a way that “LinkedIn Learning instructor” does not, even when the LinkedIn Learning work is objectively more demanding.
Next, reframe your recorded work as evidence of scale and clarity. A course with two hundred thousand learners is proof that your material holds up at volume. That’s a selling point to a training org because it addresses the one question they can’t answer from a resume, which is whether your content actually works when people try to learn from it.
Then put your MVP in context. Don’t assume procurement knows what it is. Spell it out. A sentence like “Microsoft recognizes me annually through the MVP award for sustained contribution to the Excel community. Fewer than four thousand MVPs exist worldwide across all Microsoft products” puts the award in the same frame as any other scarce, competitive credential. Suddenly it reads like what it is, which is a harder-to-earn designation than MCT.
Finally, give them a live teaching clip. Not a polished video, not an edited course preview. A raw recording of you running a session, taking questions, adjusting on the fly. That kills the classroom-control objection faster than anything you can put on a resume.
The bigger picture
There’s a deeper thing going on here that’s worth naming. Training orgs buy instructors the way procurement buys any input. They want predictable, interchangeable parts that can be slotted into a standardized product and resold at a margin. Someone with a distinct voice, an owned audience, and a body of published work is harder to standardize by definition. That can work against you inside their system, even when it works for you everywhere else.
The most useful reframe I’ve found is this. Some clients want to hire you. Other clients want to hire a resource who happens to be you. Those are very different relationships, and they signal their intent early if you’re paying attention. The ones who light up about your book, your LinkedIn Learning numbers, and your MVP status are the ones where the engagement is going to be any good. The ones who want to sand all of that down to fit a standard template are telling you something, and it’s worth listening the first time.
Their system is one distribution channel, not the scoreboard. Stop chasing the clients who want to de-risk you into a generic instructor. Work with the ones who want you to be you. The rest aren’t worth the argument.
What to do about it
If you’re in the same boat, here’s the short version.
- Translate every credential into language procurement understands. MVP is industry recognition. Courses are proof of scale. Books are proof of depth. Do the translation yourself, because they won’t.
- Quantify your live work. Count the sessions, count the attendees, count the years, and put the numbers on the page.
- Offer a live teaching sample. A raw clip of you running a real session closes the classroom-control objection faster than anything else you can send.
- Keep building your own channel. Own your list, own your content, own your relationships with past clients. Training orgs are one pipe in the plumbing, not the whole system.
- Pay attention to who wants to hire you and who wants to hire a resource who happens to be you. Work with the first group. The second group will eventually ask you to be less of yourself, and at that point you’re right back where you started.
Closing thought
The older I get in this business, the more I think the frustration of being overqualified in a standardized system is actually useful information. It tells you where you fit and where you don’t. It tells you which clients are going to respect the thing you’ve spent years building, and which ones are going to try to sand it off so they can sell you by the hour.
If you’re a specialist in Excel, analytics, Python, or any other technical tool, and you’ve put the work in to build a voice and an audience, don’t apologize for that in these conversations. Don’t water it down to slip through the checkbox. Keep writing, keep teaching, keep earning the credentials that actually mean something in your field. The right clients show up eventually, and they don’t ask you to be anyone else when they do.