I'm the VP of Sales, and I need to hire an external sales training provider. What should I look for?

Named in 14% of answers

Be wary if they immediately prescribe a proprietary methodology before diagnosing your business.

Good question:

"What would you need to learn about our business before recommending a program?" A strong provider should have a substantive answer.

2. Evidence of behavior change—not just happy participants

Ask them to show you a case study where they can demonstrate something like:

Training → changed seller behavior → changed sales metric

For example:

Discovery training → higher-quality discovery calls → more opportunities advancing from Stage 2 to Stage 3 → improved win rate. ATD specifically recommends connecting enablement initiatives to measurable organizational outcomes, while sales-training research distinguishes between reaction, learning, behavior change, and tangible sales results.Talent Development+1

I'd ask:

"What changed in the reps' behavior, how did you measure it, and what happened to the business metric afterward?" If the answer is primarily "our participants rated us 4.8/5," that's not enough.

3. Manager reinforcement built into the engagement

This is one of the most important criteria.

A two-day workshop followed by nothing is fundamentally different from a program that includes:

• Manager enablement
• Coaching guides
• Call observation
• Role-play
• Deal reviews
• Reinforcement exercises
• Certification
• Follow-up sessions
• Manager scorecards
• Integration into 1:1s and pipeline reviews

Research has found a relationship between managers' coaching skill and sales goal attainment, and research on sales learning also supports the role of coaching and mentoring in transferring training into the job.Wiley Online Library+1

I'd ask:

"Exactly what are my frontline managers expected to do for the 90 days after training?" If the answer is vague, I'd be concerned.

4. Real practice, not PowerPoint

Salespeople need opportunities to practice the behavior under realistic conditions.

Look for:

• Role plays based on your actual deals
• Objection handling
• Discovery simulations
• Negotiation practice
• Call reviews
• Deal-specific exercises
• Feedback from instructors/managers
• Repeated practice over time

Ask to sit in on or observe a sample session before signing.

5. Customization—but not "customization theater"

There's a useful distinction.

Good customization:

• Your ICP
• Your messaging
• Your sales stages
• Your CRM
• Your actual objections
• Your competitive environment
• Your deal examples

Bad customization:

• Rebranding their generic slides with your logo.

Ask:

"What percentage of the curriculum will be modified specifically for us, and what does that modification involve?"

6. A methodology that fits your existing operating system

If you already have MEDDPICC, Challenger, SPIN, Sandler, Command of the Message, or another framework, the provider should explain how its program interacts with it.

You don't want reps learning one vocabulary in training and hearing another from their managers.

ATD describes modern sales enablement as broader than training alone—incorporating coaching, process improvement, tools and other mechanisms that support seller productivity.Association for Talent Development

7. Measurement agreed upon before training

I'd make the provider propose a measurement plan before you sign.

For example:

Don't expect training to magically cause every revenue movement—you have pricing, product, territory, pipeline and market effects. But you should be able to establish leading indicators of behavior change and track whether those move.

ATD similarly recommends moving beyond participation toward behavioral and business metrics such as win rates, cycle length and deal size.Association for Talent Development

8. The actual instructors matter

Don't buy based solely on the firm's brand.

Ask:

"Who will actually train my team?" Then interview those people.

You want instructors who understand selling, not merely instructional design. I'd look for people who have actually managed sellers, carried a quota, coached reps, or worked deeply in the type of sales environment you operate.

Also ask whether the salesperson who sold you the program will be involved after the contract is signed.

9. Strong references—and permission to ask uncomfortable questions

Get 3 references from companies resembling yours.

Don't just ask:

"Did you like the provider?" Ask:

• Did reps actually change their behavior?
• What didn't work?
• How much customization was really provided?
• How involved were managers?
• Did the provider stick around after delivery?
• Did you see measurable business impact?
• Would you hire them again?
• What did you wish you'd known before signing?

That last question is particularly valuable.

The commercial model matters too

I'd compare providers on total cost, not workshop price.

Consider:

• Design/customization
• Instructor days
• Participant days
• Manager training
• Coaching
• Follow-up
• Certification
• Content/licenses
• Technology
• Travel
• Measurement
• Internal time required

A $50K workshop that requires little internal effort may be more economical than a $30K program that consumes hundreds of hours of your managers' time.

Red flags

I'd be particularly cautious if you hear:

• "Our methodology works for every sales organization."
• "We guarantee a 20% increase in revenue."
• "You don't need your managers involved."
• "It's a two-day transformation."
• "Our NPS is 95."
• "We don't need access to your CRM."
• "Customization isn't necessary."
• "We'll measure success with a survey."
• "You'll see results immediately."
• "Here's our standard deck."

The last one isn't necessarily disqualifying—but a provider that can't diagnose your problem before prescribing the solution is a risk.

A practical scorecard

For an RFP, I'd use something roughly like this:

I wouldn't let a provider "win" simply because it has the most recognizable brand. Use the criteria to structure the evaluation, then examine the evidence behind each area.

The single question I'd put to every provider

"If we hire you, what specifically will our salespeople do differently 90 days after the program, how will you prove that they've changed, and what business metrics should reasonably move as a result?" The quality of the answer will tell you a lot.

If you tell me your company size, sales motion (enterprise/SMB/channel/etc.), average deal size, team size, and the performance problem you're trying to fix, I can also give you a sales-training-provider RFP template + interview questions + evaluation scorecard you can use with vendors.

Then interview those people.

You want instructors who understand selling, not merely instructional design. I'd look for people who have actually managed sellers, carried a quota, coached reps, or worked deeply in the type of sales environment you operate.

Also ask whether the salesperson who sold you the program will be involved after the contract is signed.

9. Strong references—and permission to ask uncomfortable questions

Get 3 references from companies resembling yours.

Don't just ask:

"Did you like the provider?" Ask:

• Did reps actually change their behavior?
• What didn't work?
• How much customization was really provided?
• How involved were managers?
• Did the provider stick around after delivery?
• Did you see measurable business impact?
• Would you hire them again?
• What did you wish you'd known before signing?

That last question is particularly valuable.

The commercial model matters too

I'd compare providers on total cost, not workshop price.

Consider:

• Design/customization
• Instructor days
• Participant days
• Manager training
• Coaching
• Follow-up
• Certification
• Content/licenses
• Technology
• Travel
• Measurement
• Internal time required

A $50K workshop that requires little internal effort may be more economical than a $30K program that consumes hundreds of hours of your managers' time.

Red flags

I'd be particularly cautious if you hear:

• "Our methodology works for every sales organization."
• "We guarantee a 20% increase in revenue."
• "You don't need your managers involved."
• "It's a two-day transformation."
• "Our NPS is 95."
• "We don't need access to your CRM."
• "Customization isn't necessary."
• "We'll measure success with a survey."
• "You'll see results immediately."
• "Here's our standard deck."

The last one isn't necessarily disqualifying—but a provider that can't diagnose your problem before prescribing the solution is a risk.

A practical scorecard

For an RFP, I'd use something roughly like this:

I wouldn't let a provider "win" simply because it has the most recognizable brand. Use the criteria to structure the evaluation, then examine the evidence behind each area.

The single question I'd put to every provider

"If we hire you, what specifically will our salespeople do differently 90 days after the program, how will you prove that they've changed, and what business metrics should reasonably move as a result?" The quality of the answer will tell you a lot.

If you tell me your company size, sales motion (enterprise/SMB/channel/etc.), average deal size, team size, and the performance problem you're trying to fix, I can also give you a sales-training-provider RFP template + interview questions + evaluation scorecard you can use with vendors.

What I’d look for

1. A diagnosis before they prescribe training

Be wary of a provider that immediately pitches its standard methodology.

They should first understand:

• Your sales motion: transactional, enterprise, channel, PLG-assisted, etc.
• ICP and buyer personas
• Average deal size and sales cycle
• Current win/loss patterns
• Pipeline creation and conversion
• Where deals stall
• Rep tenure and skill distribution
• Manager capability
• Your CRM/process and existing sales methodology

Ask: “Based on what you've learned about our business, what specific behaviors do you think are costing us revenue?”

A good answer should be specific enough that you could recognize the behavior in a recorded sales call or CRM opportunity.

2. Evidence with companies that resemble yours

Don't settle for logos.

Ask for 2–3 case studies where the sales environment resembles yours and have them walk you through:

Problem → diagnosis → intervention → behavior change → business outcome Look for metrics such as win rate, conversion between stages, sales-cycle length, deal size, expansion/renewal performance, or forecast accuracy—not just “98% of participants rated the training highly.”

The distinction matters: satisfaction and knowledge tests don't establish that sellers actually changed what they do in the field.ATD

3. Real practice, not a motivational workshop

I'd want to see substantial opportunities for reps to practice the actual behaviors you're trying to change.

For example:

• Role plays based on your real opportunities
• Discovery practice
• Objection handling
• Executive conversations
• Negotiation
• Mutual action plans
• Competitive positioning
• Deal strategy
• Call/meeting simulations
• Individual feedback and coaching

Ask to experience a 30–45 minute sample session yourself. You'll learn more from that than from a polished vendor presentation.

4. Manager reinforcement is built in

This is one of the biggest things I'd put into the RFP.

Training that ends when the instructor leaves the room is much harder to translate into sustained behavior. ATD specifically recommends ongoing reinforcement and reassessment rather than treating training as a one-time event.ATD

The provider should explain exactly how managers will:

• Observe the new behaviors
• Coach them
• Inspect them in pipeline/deal reviews
• Give feedback
• Reinforce them in 1:1s
• Hold reps accountable

I'd ask:

“What are my frontline managers doing differently on Monday morning because of your program?”

If they don't have a concrete answer, that's a concern.

5. A measurement plan agreed before launch

Have the provider establish a baseline before training.

I'd want three layers:

The Kirkpatrick framework similarly distinguishes reaction, learning, behavior and results, with behavior and results being critical for demonstrating actual impact.ATD+1

Even better: agree upfront on what would constitute success at 30, 60, 90 and 180 days.

6. Customization without creating a science project

You want relevant, not necessarily completely bespoke.

Good customization might include:

• Your ICP
• Your products
• Your competitive landscape
• Your sales stages
• Your terminology
• Your actual deals
• Your call recordings
• Your CRM data

But I'd avoid paying a huge premium simply for putting your logo on their slides.

7. Methodology that's coherent and teachable

Ask them to explain their methodology in plain English.

You should be able to answer:

“What exactly are you teaching our reps to do differently?”

And ideally reduce it to a manageable number of observable behaviors.

If the methodology requires 47 concepts, acronyms and steps, adoption may be difficult.

8. The actual people matter

Don't just buy the firm's brand.

Ask:

• Who will actually facilitate?
• How much experience do they have selling/training in environments like ours?
• Who designs the program?
• Who will coach our managers?
• What happens if our assigned facilitator leaves?
• Can we speak with recent clients, not just hand-picked reference accounts?

I'd interview the person who will actually be in front of your reps before signing.

9. Technology should support the behavior—not be the product

AI role-play, call analysis, LMS integration, reinforcement platforms, etc. can be useful.

But don't buy technology because it's impressive.

Ask:

“What seller behavior does this technology improve, and how will we know?”

10. Commercial terms should align with the outcome

I'd avoid contracts where you're effectively paying entirely for seats and training days.

Consider negotiating:

• Pilot before full rollout
• Milestone-based expansion
• Clear deliverables
• Measurement commitments
• Manager coaching included
• Reinforcement included
• Reasonable replacement/termination provisions

I wouldn't necessarily demand a pay-for-performance model—it can create its own problems—but the provider should have skin in the game around measurable outcomes.

A practical vendor scorecard

I'd structure your evaluation around something like this:

Those weights aren't a ranking of providers—they're simply a useful procurement framework you can adjust to your situation.

Five questions I'd ask every provider

1. “What evidence do you have that your program changes seller behavior, not just participant satisfaction?”
2. “Show me a client whose sales environment looks most like ours. What changed, and how was it measured?”
3. “What will our frontline managers do differently after the program?”
4. “What will you measure at 30, 60, 90 and 180 days?”
5. “If I gave you our win/loss data, pipeline data and call recordings, what would you want to diagnose before recommending a program?”

That last question is particularly revealing. A provider that wants to diagnose your commercial problem first is approaching the engagement differently from one trying to sell you a prepackaged course. Current provider-selection guidance also emphasizes diagnosis, behavior change, manager reinforcement, and revenue-linked measurement.corporatevisions.com

One final filter

I'd make the final decision hinge on this:

“Can this provider help my managers change what my reps do in customer conversations—and can we prove that change?” If the answer is yes, you're evaluating a sales-performance partner. If the answer is primarily “Our workshop gets outstanding participant feedback,” you're mostly evaluating a training vendor.

Ask:

“What seller behavior does this technology improve, and how will we know?”

10. Commercial terms should align with the outcome

I'd avoid contracts where you're effectively paying entirely for seats and training days.

Consider negotiating:

• Pilot before full rollout
• Milestone-based expansion
• Clear deliverables
• Measurement commitments
• Manager coaching included
• Reinforcement included
• Reasonable replacement/termination provisions

I wouldn't necessarily demand a pay-for-performance model—it can create its own problems—but the provider should have skin in the game around measurable outcomes.

A practical vendor scorecard

I'd structure your evaluation around something like this:

Those weights aren't a ranking of providers—they're simply a useful procurement framework you can adjust to your situation.

Five questions I'd ask every provider

1. “What evidence do you have that your program changes seller behavior, not just participant satisfaction?”
2. “Show me a client whose sales environment looks most like ours. What changed, and how was it measured?”
3. “What will our frontline managers do differently after the program?”
4. “What will you measure at 30, 60, 90 and 180 days?”
5. “If I gave you our win/loss data, pipeline data and call recordings, what would you want to diagnose before recommending a program?”

That last question is particularly revealing. A provider that wants to diagnose your commercial problem first is approaching the engagement differently from one trying to sell you a prepackaged course. Current provider-selection guidance also emphasizes diagnosis, behavior change, manager reinforcement, and revenue-linked measurement.

One final filter

I'd make the final decision hinge on this:

Red flag: They prescribe MEDDICC, Challenger, Sandler, SPIN, etc. before understanding your business.

You want them to distinguish whether your problem is actually skill, process, management, strategy, messaging, or execution.A Sales Growth Company

2. Demand proof with companies that look like yours

Don't be overly impressed by logos.

Ask:

“Show me three customers with a sales motion, ACV, sales cycle, and buyer similar to ours. What problem did you solve, what specifically did you change, and what happened afterward?” The best evidence connects problem → intervention → behavior change → business outcome. Awards, famous client logos and trainer credentials are secondary.Corporate Visions

I'd want to see evidence around metrics such as:

• Win rate
• Pipeline conversion
• Average deal size
• Sales-cycle duration
• Forecast accuracy
• Discounting
• Rep ramp time
• Expansion/retention

3. Make behavior change the centerpiece

This is probably my #1 criterion.

Ask exactly how they move people from:

“I understand the methodology” → “I consistently use it with customers.”

Look for:

• Realistic role plays
• Practice with feedback
• Deal-specific exercises
• Call reviews
• Manager observation/coaching
• Application to active opportunities
• Reinforcement over weeks/months
• Skills assessments before and after

Training that produces enthusiastic participants but no change in selling behavior is expensive entertainment.

4. Evaluate their manager enablement separately

This is where I would differentiate providers aggressively.

Ask:

“What are you doing with my frontline managers so they can reinforce this after you leave?” Managers should have specific coaching routines tied to the methodology—for example, using discovery skills during call coaching and deal reviews rather than simply asking whether the rep "used the framework."

There is empirical evidence linking effective managerial coaching skill with sales goal attainment, and research has long identified manager involvement and follow-up as important parts of sales training.Wiley Online Library+1

Red flag: “We'll train your reps, and then your managers can reinforce it.”

No. Manager reinforcement should be part of the product you're buying.

5. Ask how they will customize without destroying scalability

You want enough customization that sellers recognize your world, but not so much that you're effectively paying them to reinvent sales training from scratch.

A strong provider should be able to incorporate:

• Your buyer personas
• Your messaging
• Your sales stages
• Your competitive landscape
• Your qualification criteria
• Your actual opportunities
• Your CRM terminology
• Your existing sales methodology/process

Ask to see an example of how they customize their standard curriculum.

6. Insist on an ROI/measurement plan before signing

Don't accept:

“We'll survey the reps after training.” That's useful, but it's not ROI.

I'd establish three layers:

Learning

• Did reps acquire the skill?

Behavior

• Are they actually using it in customer interactions?

Business impact

• Did the relevant sales metrics improve?

That progression is consistent with established approaches to evaluating sales-training effectiveness.North American Sales Training Corp.+1

Ideally, your provider helps establish a baseline before training and agrees on what you'll measure at 30, 60, 90 and 180 days.

7. Pay attention to the actual trainers

This gets overlooked during procurement.

You may fall in love with the firm's methodology and discover that the person delivering your program is mediocre.

Ask:

“Who specifically will work with my team?” Then interview that person.

I'd assess:

• Actual sales experience
• Experience selling to your buyer
• Facilitation ability
• Ability to challenge senior sellers
• Coaching ability
• Industry knowledge
• Whether they can handle experienced/high-performing reps

The quality of the instructor matters; research on sales-training effectiveness has also identified the instructor as an important factor.DOI+1

8. Look at what happens after the workshop

A useful program might look something like:

Week 0: Diagnostic + baseline Weeks 1–2: Core training Weeks 2–6: Practice + manager coaching Weeks 4–8: Live deal application Months 2–3: Reinforcement + certification Months 3–6: Measurement + targeted coaching

A two-day event followed by silence is a very different investment from a six-month behavior-change program.

9. Make them sell you

This is a surprisingly good test.

Watch how they conduct your buying process.

Do they:

• Ask good discovery questions?
• Challenge your assumptions?
• Understand business impact?
• Adapt to different stakeholders?
• Listen?
• Diagnose before prescribing?
• Follow up thoughtfully?
• Build a compelling business case?

If their own sales process is sloppy, I'd be very skeptical that they're going to teach your team excellent selling.

10. Understand the commercial model

Get clarity on:

• Initial program cost
• Customization fees
• Travel
• Manager coaching
• Reinforcement
• Assessments
• Technology/licenses
• Follow-up sessions
• Certification
• Measurement/ROI work

Then ask:

“What does a successful engagement cost all-in over 6–12 months?” That's more useful than comparing the price of individual workshops.

My suggested scorecard

I'd put this into your RFP and have every vendor score themselves 1–5:

Don't let price dominate the score. A provider that costs 30% more but materially improves win rate can be dramatically cheaper than a mediocre provider.

Five questions I'd ask every finalist

1. “Based on what you've learned about us, what do you think is actually causing our sales-performance problem?”
2. “What specific seller behaviors will be different 90 days after training?”
3. “How will our frontline managers reinforce those behaviors every week?”
4. “Show me the evidence that this worked for a company like ours.”
5. “Exactly how will we determine whether your program generated a return?”

And I'd add one killer question:

“If you were in my seat, what would make you not hire your company?” The quality of that answer can tell you a lot.

One final thought

As VP of Sales, I'd resist framing this as “Which sales training company is best?”

The better question is:

“What specific revenue problem are we trying to change, what seller/manager behaviors cause that problem, and which partner has the strongest evidence that they can change those behaviors in an organization like ours?”

That framing will dramatically improve your vendor selection.Corporate Visions+1

If you tell me your industry, sales model (enterprise/mid-market/SMB), average deal size, sales cycle, team size, and the performance problem you're trying to fix, I can also build you a vendor RFP + 100-point evaluation scorecard + finalist interview questions.

To help narrow down the ideal profile for your team, tell me:

• What is your industry and sales model (e.g., B2B enterprise, SMB transactional, inbound/outbound)?
• What is the primary pain point you are trying to solve (e.g., low conversion rates, weak discovery calls, poor prospecting)?
• Are you looking for a one-time workshop or an ongoing partnership?

To help narrow down the right partner profile, let me know:

• What is your industry and average deal size?
• Is your sales motion primarily transactional, consultative, or enterprise/complex?
• Are you looking to fix a specific problem (e.g., stalled pipeline, low win rates , or slow rep onboarding)?

A good provider should spend meaningful time diagnosing why the problem exists before prescribing training. If they jump straight into showing you their methodology, that's a yellow flag.

2. Look for genuine fit with your sales motion

The provider should understand your:

• ICP and buyer personas
• Average deal size and sales cycle
• New-logo vs. expansion motion
• SMB/mid-market/enterprise model
• Direct vs. channel sales
• Competitive environment
• Sales methodology and CRM
• Typical deal stages and failure points

Ask them:

"Show me exactly how you would adapt your program to our sales process rather than simply putting our logo on your standard curriculum." You want customization of application, not necessarily a completely bespoke methodology.

3. Demand evidence of behavior change

This is probably my biggest selection criterion.

A mediocre provider gives you:

Workshop → happy reps → completion certificate

A strong provider gives you:

Training → practice → feedback → application to live deals → manager coaching → reinforcement → measurable behavior change

Look for role plays, realistic simulations, deal coaching, call reviews, field assignments, reinforcement, and manager involvement. Current guidance emphasizes exactly this progression because training that isn't reinforced tends not to translate into sustained behavior change.Corporate Visions

I'd ask:

"What will my reps actually do differently 30, 60, and 90 days after the training?" If they can't answer that concretely, keep looking.

4. Make frontline managers part of the solution

This is frequently overlooked.

Your sales managers are the mechanism that turns a training event into a new operating behavior. Research has found meaningful relationships between effective managerial coaching and sales goal attainment.Wiley Online Library

So I would want the provider to train managers on:

• What to observe
• How to coach the new behaviors
• How to inspect opportunities
• How to reinforce the methodology in pipeline reviews
• How to give feedback
• How to diagnose whether a rep has a skill problem or a will/process problem

If the provider's proposal is 100% rep training and 0% manager enablement, I'd be skeptical.

5. Ask for proof in companies that look like yours

Don't be impressed by:

"We've trained 50,000 salespeople." Ask:

"Show me three companies with a sales motion, deal size, buyer, and organizational complexity similar to ours." Then ask for specifics:

• What was the original problem?
• What did you change?
• How many sellers participated?
• What did managers do?
• What changed behaviorally?
• What changed commercially?
• Over what period?
• How was the impact measured?
• What didn't work?

The quality of the answers is more important than the logo slide.

6. Get very specific about measurement

I'd establish the measurement plan before signing the contract.

Think about three levels:

Training completion and "4.8/5 instructor rating" are useful operational metrics, but they're not the business case. Current sales-enablement frameworks similarly recommend connecting training to behavioral and revenue outcomes.Absorb LMS Software+1

Ideally, the provider helps you establish a baseline before training and then compares results afterward.

7. Evaluate the actual instructors—not just the company

This one matters enormously.

Ask:

"Who exactly will be in the room?" Then interview those people.

You want someone who has actually sold, managed sellers, coached salespeople, or operated in the type of sales environment you have—not merely someone who is excellent at presenting a methodology.

I'd rather have a phenomenal practitioner from a smaller firm than a mediocre facilitator from a famous training brand.

8. Look for reinforcement over 90–180 days

I'd be wary of a provider whose solution is essentially:

"We'll come in for two days and transform your sales team." Instead, look for something like:

Week 0: Diagnostic Weeks 1–2: Core training Weeks 3–6: Practice + manager coaching Weeks 6–12: Live-deal application + reinforcement 90 days: Behavioral assessment 180 days: Business-impact review

The exact cadence will vary, but the principle is important: training should be an intervention, not an event.

9. Make them demonstrate the methodology

Don't just watch a sales presentation.

Give finalists a realistic scenario:

"Our rep is selling a $250K enterprise solution. The prospect likes us but says we're 30% more expensive than the incumbent. Show us how your methodology would coach the rep through this situation." Then have the provider:

1. Run the exercise.
2. Explain what the rep did well.
3. Diagnose what was missing.
4. Coach the rep.
5. Explain how a manager would reinforce it.

You'll learn more in 45 minutes than you will from 100 PowerPoint slides.

My suggested scorecard

I'd weight the evaluation approximately like this:

Notice that price is only 5%.

A provider that costs $150K more but materially improves win rate can be dramatically cheaper than the $100K "bargain" program that produces no lasting change.

Questions I'd put directly into the RFP

I'd include these almost verbatim:

1. What sales-performance problems does your methodology solve best?
2. How would you diagnose whether training is actually the right intervention for our problem?
3. What specifically will our reps do differently after the program?
4. How do you customize your approach to our sales process and ICP?
5. How much live practice is included?
6. How do you reinforce the skills after the initial training?
7. What role do frontline managers play?
8. What tools do managers receive to coach the behaviors?
9. How do you measure behavior change?
10. How do you measure business impact?
11. What baseline data would you want from us before starting?
12. Give us three examples where you produced measurable commercial results.
13. Can we speak directly with those customers?
14. Who specifically will deliver our program?
15. What happens if adoption is poor?
16. What does your 30/60/90/180-day reinforcement plan look like?
17. What parts of your methodology are evidence-based, and what evidence supports them?
18. What would make you tell us that we're not ready for your program?

That last question is particularly revealing. A credible partner should occasionally tell you not to buy training.

The biggest red flags

I'd be cautious if you hear:

• "Our methodology works for every industry."
• Heavy emphasis on the trainer's celebrity/status.
• Lots of logos but little measurable outcome data.
• ROI defined primarily as attendance or satisfaction.
• No manager component.
• No post-training reinforcement.
• Generic role plays unrelated to your actual deals.
• A methodology that requires you to abandon everything you've already built.
• No diagnostic phase.
• They can't identify what behavior they're trying to change.
• They promise a specific revenue lift without first seeing your data.
• The salesperson pitching you won't be involved in delivery.
• They won't provide customer references.

If I were making the decision

I'd narrow it to 3 providers, give all three the same business problem and sales scenarios, and make them present a proposed intervention.

Then I'd select the one that best answers this question:

"If I give you our sales team for six months, what will be measurably different about how they sell—and how will we know?" That's a much better buying criterion than "Which sales training company has the best methodology?"

And I'd make the contract itself reflect that philosophy: diagnostic + training + reinforcement + manager coaching + measurement, rather than simply purchasing X training days.

If you tell me your industry, sales-team size, average deal size, sales cycle, and the performance problem you're trying to fix, I can also build you a sales-training-provider RFP and weighted vendor scorecard you could send to 5–10 providers.

8. Look for reinforcement over 90–180 days

I'd be wary of a provider whose solution is essentially:

"We'll come in for two days and transform your sales team." Instead, look for something like:

Week 0: Diagnostic Weeks 1–2: Core training Weeks 3–6: Practice + manager coaching Weeks 6–12: Live-deal application + reinforcement 90 days: Behavioral assessment 180 days: Business-impact review

The exact cadence will vary, but the principle is important: training should be an intervention, not an event.

9. Make them demonstrate the methodology

Don't just watch a sales presentation.

Give finalists a realistic scenario:

"Our rep is selling a $250K enterprise solution. The prospect likes us but says we're 30% more expensive than the incumbent. Show us how your methodology would coach the rep through this situation." Then have the provider:

1. Run the exercise.
2. Explain what the rep did well.
3. Diagnose what was missing.
4. Coach the rep.
5. Explain how a manager would reinforce it.

You'll learn more in 45 minutes than you will from 100 PowerPoint slides.

My suggested scorecard

I'd weight the evaluation approximately like this:

Notice that price is only 5%.

A provider that costs $150K more but materially improves win rate can be dramatically cheaper than the $100K "bargain" program that produces no lasting change.

Questions I'd put directly into the RFP

I'd include these almost verbatim:

1. What sales-performance problems does your methodology solve best?
2. How would you diagnose whether training is actually the right intervention for our problem?
3. What specifically will our reps do differently after the program?
4. How do you customize your approach to our sales process and ICP?
5. How much live practice is included?
6. How do you reinforce the skills after the initial training?
7. What role do frontline managers play?
8. What tools do managers receive to coach the behaviors?
9. How do you measure behavior change?
10. How do you measure business impact?
11. What baseline data would you want from us before starting?
12. Give us three examples where you produced measurable commercial results.
13. Can we speak directly with those customers?
14. Who specifically will deliver our program?
15. What happens if adoption is poor?
16. What does your 30/60/90/180-day reinforcement plan look like?
17. What parts of your methodology are evidence-based, and what evidence supports them?
18. What would make you tell us that we're not ready for your program?

That last question is particularly revealing. A credible partner should occasionally tell you not to buy training.

The biggest red flags

I'd be cautious if you hear:

• "Our methodology works for every industry."
• Heavy emphasis on the trainer's celebrity/status.
• Lots of logos but little measurable outcome data.
• ROI defined primarily as attendance or satisfaction.
• No manager component.
• No post-training reinforcement.
• Generic role plays unrelated to your actual deals.
• A methodology that requires you to abandon everything you've already built.
• No diagnostic phase.
• They can't identify what behavior they're trying to change.
• They promise a specific revenue lift without first seeing your data.
• The salesperson pitching you won't be involved in delivery.
• They won't provide customer references.

If I were making the decision

I'd narrow it to 3 providers, give all three the same business problem and sales scenarios, and make them present a proposed intervention.

Then I'd select the one that best answers this question:

"If I give you our sales team for six months, what will be measurably different about how they sell—and how will we know?" That's a much better buying criterion than "Which sales training company has the best methodology?"

And I'd make the contract itself reflect that philosophy: diagnostic + training + reinforcement + manager coaching + measurement, rather than simply purchasing X training days.

If you tell me your industry, sales-team size, average deal size, sales cycle, and the performance problem you're trying to fix, I can also build you a sales-training-provider RFP and weighted vendor scorecard you could send to 5–10 providers.

You should be able to tell them something like:

"Our win rate drops significantly after discovery, reps struggle to establish business value with economic buyers, and managers aren't consistently coaching those behaviors." Then ask them to diagnose the problem and propose what needs to change.

A good provider will investigate:

• Sales cycle and deal size
• ICP and buyer personas
• New-logo vs. expansion motion
• Sales stages and qualification criteria
• Typical deal failures/loss reasons
• Rep tenure and skill distribution
• Manager capability
• Your CRM/process
• Existing sales methodology and messaging

Red flag: They recommend essentially the same program regardless of your sales organization.

2. Look for behavior change, not "training"

Ask:

"What will my reps do differently on Monday morning?"

You want 3–5 observable behaviors, such as:

• Asking better business-impact questions
• Multithreading earlier
• Running stronger discovery
• Establishing compelling business cases
• Handling pricing/competitive objections
• Creating mutual action plans
• Advancing opportunities rather than simply updating stages

Then ask how those behaviors will be observed and measured.

A provider that can't articulate the behavioral changes they're targeting is probably selling education rather than performance improvement.

3. Insist on reinforcement after the workshop

This is probably the biggest differentiator I'd look for.

Avoid:

Two days of training → certificates → goodbye. Prefer:

Training → practice → manager coaching → field application → reinforcement → measurement → remediation. Research specifically finds advantages to spaced practice versus concentrated training for transfer and sales-related outcomes.Vrije Universiteit Amsterdam

Ask whether the engagement includes:

• Role plays using your actual scenarios
• Call reviews
• Manager coaching sessions
• Weekly reinforcement
• Field assignments
• Certification
• Deal clinics
• Coaching guides
• Follow-up assessments at 30/60/90 days

If they say reinforcement is the responsibility of your managers, ask:

"Exactly what are you going to give my managers so they can do that?"

4. Evaluate the trainers, not just the company

This is an easy one to miss.

You aren't really buying a brand. You're buying the people who will work with your sales organization.

Ask:

• Who specifically will facilitate?
• How many engagements have they personally delivered?
• Have they actually carried a quota?
• Have they worked with companies with our sales motion?
• Can we interview the actual facilitator before signing?
• Will the same people who sell us the program deliver it?

I'd rather hire a smaller provider with excellent practitioners who understand your business than a famous training brand whose A-team disappears after the sale.

5. Demand relevant proof

Don't accept:

"We've trained 50,000 salespeople." That's largely meaningless.

Ask for three references that look like you:

• Similar ACV
• Similar sales cycle
• Similar buyer
• Similar team size
• Similar growth stage
• Similar complexity

Then ask those customers:

1. What problem did you hire them to solve?
2. What actually changed?
3. What didn't work?
4. How much work did your internal team have to do?
5. Did managers actually use the methodology afterward?
6. What measurable business results did you see?
7. Would you hire them again?

That last question is particularly revealing.

6. Make measurement part of the contract

Don't let the provider define success as:

• 95% attendance
• 4.8/5 satisfaction
• 90% course completion
• "Reps loved it"

Those are useful operational metrics, but they're not the business case.

Build a measurement chain:

Training → proficiency → behavior change → pipeline/deal behavior → revenue outcome

Potential metrics include:

This is consistent with research emphasizing evaluation beyond participant reaction and toward learning, behavior, and results.DOI+1

I'd establish a baseline before training and agree in advance on what improvement would constitute success.

7. Make your frontline managers part of the solution

This is critical.

If your managers don't reinforce the new behaviors, reps will eventually revert to their old habits. Research on training transfer also finds feedback/coaching to be a particularly strong contributor to transfer.Wiley Online Library

I'd therefore ask every provider:

"What is the manager component of your program?" A strong answer includes things like:

• Manager bootcamp
• Coaching framework
• Deal-review methodology
• Observation checklists
• 1:1 coaching templates
• Certification standards
• Ongoing manager calibration

If the provider primarily trains reps but barely involves managers, I'd be skeptical.

8. Make sure it fits your sales motion

A great methodology can still be wrong for you.

For example, training designed for transactional SMB sales may be poorly suited to:

• Enterprise SaaS
• Complex B2B
• Channel sales
• Professional services
• Strategic accounts
• Highly technical products

Ask them to demonstrate how their approach handles one of your actual opportunities.

Give them a real (appropriately anonymized) deal and ask:

"Walk us through exactly how your methodology would change what the rep does here." That's much more revealing than a polished demo.

9. Look carefully at customization

There's a spectrum:

Generic course ←→ Fully customized intervention

You generally want somewhere toward the customized end—but not necessarily a completely bespoke program that costs a fortune and can't scale.

Ask what they will customize:

• Messaging
• Buyer scenarios
• Discovery questions
• Role plays
• Objection handling
• CRM stages
• Qualification criteria
• Industry examples
• Manager coaching
• Certification

And ask what they won't customize. Good providers usually have a core methodology they're disciplined about preserving.

10. Understand the economics

Don't just compare the quoted training fee.

Calculate:

Total cost = provider fees + seller time + manager time + travel + implementation + technology + opportunity cost

Then compare that with the economic upside.

For example, if you have 40 reps and the program costs $150K, the relevant question isn't "Is $150K expensive?"

It's:

"What improvement in win rate, ACV, ramp time, or quota attainment would produce $150K+ of incremental gross profit?" A provider should be willing to have that conversation with you.

My provider scorecard

I'd actually send finalists something like this:

I'd deliberately make price a low-weight criterion. A cheap program that doesn't change selling behavior is extremely expensive.

Questions I'd put in the RFP

1. What do you need to learn about our business before recommending a program?
2. What specific seller behaviors would you expect to change?
3. How do you measure whether those behaviors actually changed?
4. What happens after the initial training?
5. How do you involve frontline managers?
6. How much of the program is customized?
7. Who will actually deliver the training?
8. Show us three customers with a sales environment similar to ours.
9. What measurable results did those customers achieve?
10. What would you measure before, during, and 90 days after the program?
11. What does our leadership team need to do for this to succeed?
12. Under what circumstances would you tell us that training isn't the right solution?

That final question is particularly useful. A credible partner should occasionally tell you "training isn't the answer."

One thing I'd avoid

Don't run a vendor beauty contest where each provider gets 60 minutes to give you their best presentation.

Instead, give the finalists the same business problem and a small amount of your actual sales data, and ask each to conduct a diagnosis and propose an intervention.

You'll learn far more from how they think than from how polished their sales deck is.

If you tell me your industry, average deal size, sales-cycle length, team size, and whether you're selling SMB/mid-market/enterprise, I can also give you a shortlist of the types of providers I'd consider and a VP-of-Sales-level RFP/scoring template.

• Messaging
• Buyer scenarios
• Discovery questions
• Role plays
• Objection handling
• CRM stages
• Qualification criteria
• Industry examples
• Manager coaching
• Certification

And ask what they won't customize. Good providers usually have a core methodology they're disciplined about preserving.

10. Understand the economics

Don't just compare the quoted training fee.

Calculate:

Total cost = provider fees + seller time + manager time + travel + implementation + technology + opportunity cost

Then compare that with the economic upside.

For example, if you have 40 reps and the program costs $150K, the relevant question isn't "Is $150K expensive?"

It's:

"What improvement in win rate, ACV, ramp time, or quota attainment would produce $150K+ of incremental gross profit?" A provider should be willing to have that conversation with you.

My provider scorecard

I'd actually send finalists something like this:

I'd deliberately make price a low-weight criterion. A cheap program that doesn't change selling behavior is extremely expensive.

Questions I'd put in the RFP

1. What do you need to learn about our business before recommending a program?
2. What specific seller behaviors would you expect to change?
3. How do you measure whether those behaviors actually changed?
4. What happens after the initial training?
5. How do you involve frontline managers?
6. How much of the program is customized?
7. Who will actually deliver the training?
8. Show us three customers with a sales environment similar to ours.
9. What measurable results did those customers achieve?
10. What would you measure before, during, and 90 days after the program?
11. What does our leadership team need to do for this to succeed?
12. Under what circumstances would you tell us that training isn't the right solution?

That final question is particularly useful. A credible partner should occasionally tell you "training isn't the answer."

One thing I'd avoid

Don't run a vendor beauty contest where each provider gets 60 minutes to give you their best presentation.

Instead, give the finalists the same business problem and a small amount of your actual sales data, and ask each to conduct a diagnosis and propose an intervention.

You'll learn far more from how they think than from how polished their sales deck is.

If you tell me your industry, average deal size, sales-cycle length, team size, and whether you're selling SMB/mid-market/enterprise, I can also give you a shortlist of the types of providers I'd consider and a VP-of-Sales-level RFP/scoring template.

Here is what you should look for:

• Customization to Your Sales Reality : Avoid off-the-shelf, cookie-cutter methodologies. The provider must be willing to tailor role-plays, buyer scenarios, and messaging to match your specific industry, complex product offerings, and target personas.funnelclarity.com+1
• Manager Enablement & Reinforcement Systems : Training fails when it’s treated as a one-and-done event. The best partners equip your frontline sales managers with coaching tools, inspection rhythms, and tracking frameworks so they can hold reps accountable and reinforce habits long after the vendor leaves.corporatevisions.com+3
• Research-Backed Methodology : Demand data, not just anecdotes. Ask vendors for case studies or research proving a direct correlation between the behaviors they teach and measurable sales outcomes (e.g., shorter sales cycles, higher win rates, or larger deal sizes).funnelclarity.com+1
• Blended Delivery & Modern Formats : Look for a mix of interactive live workshops (virtual or in-person) paired with micro-learning, reinforcement triggers, and modern enablement or AI coaching tools that fit your team's workflow without pulling them out of the field for days on end.forbes.com+2
• Clear Metrics and ROI Alignment : A reputable partner will help you define what success looks like upfront and tie program milestones directly to your key performance indicators (KPIs) rather than completion rates.corporatevisions.com+1

To narrow down the field or benchmark top-tier vendors, you can explore industry evaluations like the annual lists published by Training Industry or Selling Power.linkedin.com

To help tailor this, tell me a bit more about your situation:

• What is your primary pain point right now (e.g., low win rates, long sales cycles, poor prospecting)?
• Are you selling B2B enterprise, mid-market, or transactional?
• What does your sales enablement and manager structure look like today?