Top Sales Enablement Interview Exercises to Test Your Candidates

Hiring for enablement has never been straightforward, but over the past few years, the role has evolved in ways most interview processes have not.

Today, teams expect people in various sales enablement roles to diagnose problems, design programmes, coach effectively, influence across functions, and turn strategy into behaviour – often within a single quarter.

But most interviews rely on theoretical questions that stay at the surface. 

Candidates talk about models, past achievements, and familiar terminology, yet very little of that shows how they actually think, decide, or operate when the real work gets messy.

This is where practical exercises matter, discovering more about the candidates beyond their enablement interview prep.

They give you a glimpse of how someone analyses context, handles ambiguity, and communicates when the situation is not clean or linear.

They show how a candidate behaves in the types of scenarios that enablement lives in every day.

To understand which exercises truly expose a candidate’s real capabilities, I asked a group of senior enablement leaders – the same who contributed to my sales enablement interview tips article – a simple question:

“If you could design one practical exercise for an enablement candidate to complete during the interview process, what would it be?”

Their responses were diverse in format, yet the underlying patterns were remarkably consistent.

When grouped, they formed a set of core capability areas – the same capability areas that tend to separate high-impact enablers from those who struggle in real-world conditions.

These capability areas appear in the article as themes.

Each theme reflects a different part of the job, and each is brought to life through the exercises and perspectives shared by the sales enablement leaders themselves.

This article surfaces those themes, shows what they reveal, and offers practical interview exercises you can adopt immediately.

If you want a full picture of how to run a strong hiring loop, this piece pairs well with my article on sales enablement interview questions. Together, they give you both the “what to ask” and the “what to test”.

Theme 1 – Strategic thinking and structured analysis

If you want to test sales enablement talent, do not start with content creation or workshop delivery.

Start with thinking.

Because the best enablers do not just execute; they question, interpret, and prioritise.

They turn vague requests into structured plans, surface hidden problems, and build direction where none existed.

That ability is what theme one uncovers – the thinking behind the doing.

What strong strategic thinking looks like in practice

A strong candidate should be able to:

• break down a messy brief into logical steps
• perform discovery before proposing solutions
• distinguish symptoms from root causes
• form a plan, not just a list of ideas
• show how they would validate assumptions with data, stakeholders, and conversations

When leaders suggested exercises for interviews, almost half of them centred on this exact aspect.

Andrea Abbate, Senior Director of GTM Enablement at one of the most famous CRM companies, pushes candidates into real discomfort – a live discovery session rather than a theoretical plan:

“…do a discovery role play (enablement – Sales Leader).  

Proper disco and needs analysis is such a critical skill for enablers and is often not assessed properly at an interview.  

I’d have them read a case study (access to info they’d have as an enabler) and then run the role play. live with an actual sales manager, with the goal of seeing if they’re able to ID the root cause problem (not just the symptom), probe deeply (not jump to solution) and build rapport while challenging thinking.”

One question. One scenario.

And suddenly, their whole approach becomes visible.

A junior candidate solves the problem they’re given.

A senior enablement hire questions whether it’s the right problem.

It’s a subtle difference – until you see it.

Kyle Doerflein, Director of Sales and Solutions Engineering Onboarding at one of the major cloud providers, takes a similar angle by giving the candidates something incomplete and watching whether they build clarity or guess forward:

“It begins in the first interview asking how they approach a sales enablement project programmatically. 

Giving them a prompt, such as a vague request from a sales leader, and asking step by step how they would approach it helps determine critical thinking and problem solving as they ask discovery questions, determine the pain, identify the sales metrics that show it is a pain, and prioritize it against other work…”

The best responses start with discovery stages:

•  Who would you speak to?
•  What questions reveal the truth beneath assumptions?
•  Where could data invalidate or confirm a hypothesis?

Those who rush to output reveal more than they realise.

What you’re really looking for is how they bring order to ambiguity – the way they structure their thinking, probe for what matters, sequence their next steps, and decide what deserves attention first.

Jill Guardia, Senior Vice President of Revenue Enablement & Operations at one of digital learning powerhouses, frames it as environmental awareness: can they scope, investigate, and interview with intent?

“Provide the candidate a scenario that closely matches the environment that they will be entering and ask them how they would go about assessing the needs, who they would interview and what they might think were some of the core issues to resolve.”

Notice the shift.

It’s not just what they do; it’s who they involve and why.

Strong sales enablement thinking recognises that clarity doesn’t come from documents alone. It comes from people – the conversations you have, the voices you involve, and the context you gather through them.

Lisa Duncan, Senior Director of GTM Enablement at one of the major CRM companies, wants to see if thinking scales into a full programme:

“I’d give them a common scenario like a major product launch or a new sales methodology rollout and ask them to walk me through how they’d build a sales enablement program from start to finish. 

I want to see their full process, including how they define the need and business rationale, design the program, gain alignment from sales and marketing teams, create the content, plan facilitation and delivery, and measure impact.”

Lisa even explicitly points out that she wants to hear how they approach enablement strategically:

“I’m looking for strategic thinking, solid program design skills, data-driven decision-making, thoughtful stakeholder alignment and communications, and a clear framework or outline that shows how they structure their approach.”

Amy McClain, Senior Director of Global Enablement at the world’s leading celebration planning platform, generously shared one of her exercises in full – an assignment designed for a Sales Enablement Manager role with a strong focus on product enablement.

“Exercise One: Building World-Class Product Education

How does an ideal product educational program look for a Global Revenue org? What should be included and how do you align stakeholders around one vision? 

Using the information below, please present how you would create world-class product enablement given the priorities of TKWW’s Global Revenue organization:

Globalize the Enablement function.

Current state: US teams have comprehensive documentation and training around US brands, built in partnership with Product Marketing. For our International teams and international brands, none of this exists today and needs to be built.

Incorporate our new sales methodology in how we talk about our product, via our product training.

Establish adoption success metrics: how will you know if it’s working?

You can use whichever presentation format suits you best. We will ask you to share your screen to show the panel what you came up with.”

Chako Dickinson, Senior Onboarding, Methodology, and Skills Enablement Manager at one of the two biggest developer platforms, offers a simpler prompt that tests the same underlying skillset from a different angle:

“You’ve been tasked with creating an enablement initiative for a new product release for a frontline sales organization. Explain your approach and the steps you’d take to ensure success.”

Chuck Lee, SVP of Sales Operations and Enablement at a global leader in business expense management, and Daryl Spreiter, Head of Sales Enablement at a leading provider of satellite imagery and insights, both use scope-mapping exercises to test whether candidates can think beyond tasks and see the whole system:

“Map out a new product introduction from an enablement perspective – communications, awareness, learning, tools, etc.”

Daryl provides more context for the exercise, but the goal remains the same:

“We are at an inflection point in our company as we shift from a product sale to a solution or platform sale. 

Most of our reps have been here for a long time and know how to sell the product but are slow to adopt our overall platform message. This results in more transactional sales. 

We need to rebuild our sales organization into value sellers. Design a program that will help us achieve this objective. 

Walk us through your approach and reserve at least 5 minutes for an interactive exercise to show us how you would engage the team during training.”

As you can see, none of these exercises are about templates; they’re designed to expose thinking quality:

• Where do they begin?
• What information do they seek first?
• How do they sequence learning, testing, rollout, and measurement?
• How do they navigate unknowns without panicking?

You learn more through their slide zero than slide ten.

What the exercises in this theme ultimately reveal

Across all the examples shared by leaders, the exercises grouped under this theme consistently uncover three main things:

1. Can they diagnose, not just react? Do they peel back surface requests, look for root causes, and define the problem with care?
2. Can they structure their thinking when the context is incomplete? Do they pause, ask for what’s missing, and work step by step instead of rushing to output?
3. Can they turn insight into a practical, real-world plan? Not a list of ideas, but a sequence that could hold up in the organisation they’re entering.

These patterns matter because many candidates can talk confidently about enablement.

Plenty can share frameworks, build content, or deliver comprehensive sales training programs.

But only a smaller group think like genuine business partners – the kind who enhance sales team performance itself by clarifying focus, reducing operational drag, and enabling consistent execution in the field. 

Strategic thinking is not a nice-to-have; it’s the foundation.

If someone cannot think strategically, everything downstream breaks – programme design, stakeholder alignment, training delivery, reinforcement, and more. 

Theme 2 – Programme design and execution 

Strategic thinking shows how a candidate approaches uncertainty.

Programme design shows what they do once the path becomes clearer.

This is where judgment turns into action.

Where insight becomes structure.

Where an idea becomes something the field can actually use.

A strong enabler should be able to translate what they learned in discovery into a coherent, usable programme/intervention that supports behaviour change, whether it is reducing sales cycle length, boosting sales efficiency, or something else entirely. 

Good programme design demands an understanding of how people learn and how habits form. It also requires the ability to connect different enablement components – training, content, sales enablement tools, and coaching – into something that works over time rather than in one moment.

It asks you to design for the field as it really is: full of competing priorities, limited attention, and the need for reinforcement long after a workshop ends.

A well-designed programme is:

• Sequenced, not scattered
• Integrated, not isolated
• Grounded in the sales process, not removed from it
• Built for reinforcement, not one-off consumption

This is why programme design exercises are so revealing.

They show whether someone can turn a diagnosis into something the field can adopt, repeat, and depend on.

And when you look closely at these exercises, a few consistent signals appear.

What programme design exercises really test

They indicate whether a candidate can:

• Turn diagnosis into structure and curriculum
• Build sales materials based on need, not comfort or routine
• Sequence knowledge rather than dump it
• Consider adoption, reinforcement, and measurement from day one
• Design for real selling situations, not for presentation slides

At their best, these exercises ask someone to engineer an (ongoing) experience that helps sales representatives and managers perform better in real selling situations and translate into real, positive changes in the field. 

To illustrate this, let’s return to the exercise Amy McClain shared – the same one that appeared in Theme 1.

There, it helped us understand how candidates frame a problem, question assumptions, and organise ambiguity.

Viewed through a different lens, the very same exercise tests something else entirely: whether a candidate can build a programme once direction is set.

Amy’s assignment asks candidates to imagine a world-class product education ecosystem. On the surface, it looks like a design challenge. In practice, it probes much deeper capabilities:

• Can they translate sales enablement strategy into a workable enablement framework?
• Can they sequence learning into a curriculum that scales over time?
• Can they weave methodology into product narrative rather than bolt it on afterwards?
• Can they define success in terms of adoption and behaviour, not just attendance?

High-quality enablement isn’t a deck, a timeline, or a set of materials. It’s a system that supports sellers long after the launch moment.

Amy’s prompt helps surface who understands this distinction – and who approaches enablement as a collection of outputs that work together synergistically. 

It also shows something valuable for interviewers: the same exercise can reveal entirely different capabilities depending on how you examine it.

In Theme 1, we looked at the scenario as highlighting strategic reasoning.

Here, the very same one is being looked at as exposing execution depth – the candidate’s choices around structure, flow, alignment, and measurement.

Same scenario. Different angle. Different capabilities made visible.

Beth Shuman, Vice President Sales Operations & Sales Enablement at a leading provider of next-generation manufacturing and supply chain solutions, offers a very different kind of exercise – one that looks deceptively simple at first glance:

“Developing playbooks… ask them how they would research and develop the content, what they would include, and how they would organise it.”

Playbooks, however, are never simple.

They expose whether a candidate understands selling beyond theory.

The average candidate fills pages with frameworks, definitions, and neat conceptual models.

A strong enabler builds something the field can actually use tomorrow.

Which means Beth’s prompt uncovers:

• How they research, filter, and decide what matters
• Whether they write from the rep’s workflow, not their own
• How they translate knowledge into action
• Whether they know what “good” looks like in the real world

A highly effective sales playbook gives direction quickly while leaving room for judgment. It brings together elements that reps can use in the flow of a deal – talk tracks, prompts and cues, checklists, simple selling techniques, patterns seen in real opportunities, guidance on common breakdowns and how to recover from them, customer language, and practical examples that show what “good” looks like.

It isn’t content for reading; it’s content for selling.

That’s what Beth’s exercise tests: do they know sales well enough to enable it – or only to describe it?

And there’s one more signal worth paying attention to.

A strong candidate doesn’t treat a playbook as a static repository. They think about how it will evolve – how feedback loops will work, what triggers updates, and how to keep it relevant as the market, product, and deal patterns shift.

Kyle Doerflein takes the idea a level deeper.

Where Beth uncovers practical sales understanding, Kyle tests instructional maturity: not just whether someone can plan a programme, but whether they can design a curriculum that teaches, reinforces, and turns sales skills into behaviour.

“Sharing a curriculum or initiative design would show how they leverage Learning Objectives, Instructional Design frameworks, and delivery methods…”

This is where many candidates are exposed.

Those who have spent their careers building decks jump straight to topics and content.

Those who understand instructional design begin with outcomes.

A strong response to Kyle’s exercise sounds like applied learning science:

• Mapping learner profiles before writing content,
• Defining behavioural objectives instead of knowledge points,
• Choosing modalities with intent,
• Designing for retention through spaced reinforcement and practice,
• Measuring proficiency rather than completion.

This is where effective programme design shows itself – in how it helps people learn, practice, and turn knowledge into action and sales performance.

Liz McCune, Director of Sales Enablement at a leader in manufacturing software, widens the challenge to something very close to reality – a live launch, cross-functional complexity, asset development, timing, and roll-out “choreography”:

“Give the candidate a scenario where the sales team needs new collateral to support a product launch. Include background information on the product/service, target audience, and sales challenges.

Have the candidate create an enablement plan for the product launch detailing what would be needed, timing etc and the plan to work cross functionally within the organization to roll out the plan.”

This is an excellent exercise (with no perfect answer) that helps assess whether the candidate stages the work instead of listing deliverables: 

• Do they identify dependencies?
• Do they plan alignment before development?
• Do they distinguish training for awareness vs training for execution?
• Do they include reinforcement loops rather than a launch-day blast?
• Do they sequence enablement so reps can perform, not just attend?

A weak candidate lists materials; a strong candidate builds readiness.

A high-signal response to Liz’s scenario reads like a system in motion: handoffs from marketing and product teams → messaging → asset creation → training → reinforcement.

Cadenced communications tied to field milestones. Accountability and measurement defined early, not retrofitted. A roll-out built for adoption rather than just attendance.

Key takeaway from this theme

If we sum up what we’ve seen in this section, programme-design exercises tend to reveal three things:

1. Can they turn insight into a coherent learning journey? Not a list of deliverables, but a structured sequence – the kind Amy’s exercise makes visible when candidates have to build something that actually holds together.
2. Can they create assets the field can use in real situations? Beth’s example shows this clearly: theory and templates mean little if reps cannot apply the material the next morning.
3. Can they design for adoption, scale, and longevity? The exercises from Kyle and Liz surface this – the difference between sales training that looks good in a deck and enablement that holds up under real pipeline pressure.

Across all the examples, the same pattern appears: weak designers produce materials while strong enablers produce capability.

Programme design is the hinge between strategy and execution; it’s where intent becomes movement and progress. 

Interlude – Business fluency senior enablers must demonstrate

Before moving into delivery and facilitation, there is one capability that sits between strategy and execution – and it deserves its own pause.

The strongest enablement hires do more than think well and build well.

They speak the language of the business.

They can move comfortably between sales, finance, product, and customer success.

They understand revenue levers, risks, trade-offs, and economic reality.

And, crucially, they can position their work in terms executives care about – sales productivity, risk reduction, and revenue.

Business fluency or acumen can be a genuine differentiator.

It isn’t enough to design a programme.

A senior enabler must also be able to sell the rationale behind it, using external and internal data, qualitative insights from peers and stakeholders, and an understanding of how the company makes money.

Sheevaun Thatcher, VP of Revenue Enablement at a leading pipeline AI platform, proposes an exercise that helps evaluate this:

“Show Me You Know Me – could be a presentation or an essay. I want to see how much research they do to prepare for interview presentations to Sales Leadership and CX Leadership. Do they understand their vernacular? Can they speak in GTM business terms?

Even though they don’t have access to confidential numbers, there is a ton of research that can be done externally to uncover this information – GPT prompts, publicly available financial data, current and past employees, news, industry trends, etc.”

What she is really asking for is not a presentation in the abstract.

It is a simulated executive briefing.

The candidate must study the company from the outside, piece together what they can, and form a thoughtful view of its commercial reality. They are not expected to know the full story – they cannot. But they are expected to show how they would get as close as possible with what is publicly available.

They need to demonstrate where they would look, how they would interpret incomplete signals, and how they would communicate their conclusions as if advising Sales and CX leadership. The goal is not accuracy; it is depth, judgement, and rigour.

In other words:

“Show me that even without internal access, you know how to understand our business and where enablement could influence outcomes.”

This is where business fluency becomes a filter for who can operate at the executive level.

It reveals three things instantly:

• Whether they can investigate meaningfully without being fed the answers
• Whether they can speak in commercial terms rather than enablement abstractions
• Whether their thinking can withstand executive-level scrutiny

Anyone can speak broadly about revenue motion.

In sales enablement manager interviews, you want to see someone who can analyse it, map it, and communicate it with clarity – even when the data is imperfect.

Theme 3 – Facilitation and live teaching ability 

Programme design only reaches its potential when someone can bring it to life.

This theme shifts the focus from what a candidate builds to how they deliver it in front of real people.

A well-designed programme still fails if the facilitator cannot create clarity, hold attention, or guide people through the moments where resistance, confusion, or fatigue appear.

Interview exercises in this area often reveal something deeper than communication style.

They show how a candidate relates to learners, how they adjust in the moment, and whether they can create the conditions in which learning becomes behaviour.

The question underneath Theme 3 is simple: 

Can they teach in a way that people absorb and remember, or do they just present?

What strong facilitation looks like

High-signal exercises in this theme help you see whether a candidate can:

• Dynamically teach rather than passively lecture
• Adapt to the learner in front of them
• Simplify ideas without losing accuracy
• Keep a room engaged when the energy drops
• Create participation instead of passive listening

None of this is “performance theatre”.

It is a test of whether they know how to create understanding and retention – two things slides alone cannot achieve.

The clearest way to test this?

Give them a room, even a fictional one, and ask them to teach.

Sheryl Buscheck, Director of Global Revenue Enablement at a network infrastructure leader, goes straight to that moment:

“Pretend I’m a new-hire seller… Teach me something you already know how to teach in 20 minutes…”

There is nowhere to hide in that assignment.

You see their pacing, their framing, their ability to read the learner.

You see whether they explain, ask, involve, summarise, or talk endlessly in one direction.

A candidate with command pauses. Asks questions. Checks understanding. Moves with the learner instead of speaking at them.

Sheryl shares more about what she expects in a strong hire: 

“I expect everyone I hire to have strong communication skills and be able to teach people, and I want to see their instructor style. I don’t expect them to learn anything new – I purposely want them to talk through a topic they already know and feel comfortable teaching.”

Felix Dumitrica, Director of EMEA Revenue Enablement & Sales Engineering at a payments platform company, widens the lens with a wonderfully revealing twist:

“To teach me something I do not know [even if it is how to make a cup of tea].”

By removing enablement as a safety net, Felix uncovers pure teaching ability.

No frameworks to hide behind.

No domain knowledge to fall back on.

What remains is their ability to break something down, sequence it clearly, and adjust in real time when the learner gets stuck.

A candidate who can teach something simple with clarity usually teaches complex enablement concepts just as well.

Because the real skill is building a clear path for the learner – step by step, in the right order – regardless of the topic.

Amy McClain approaches this same area by asking candidates to prepare a short training session – a request I’ve often encountered myself during interviews: 

“Prepare a 10-15 minute training session on the topic of your choice.  Feel free to use supporting materials like a slide deck, Google doc, visual components – anything that will help highlight how you communicate and engage with your learners.”

This kind of exercise tests how thoughtfully a candidate prepares and how deliberately they guide a learning experience. 

A prepared facilitation reveals things you cannot see in spontaneous teaching, such as:

• How they organise content so the learner can follow the logic
• How they balance explanation with interaction and moments of reflection
• How they use examples, visuals, or structure to make ideas easier to grasp
• How they manage pacing and transitions so the session doesn’t feel rushed or flat
• How they anticipate common points of confusion and build clarity into the design
• How they plan engagement so the audience is involved rather than passive

A prepared exercise shows the “thinking behind the teaching”: not just whether they can talk through a topic, but whether they can design a learning moment that supports understanding and retention.

Kyle Doerflein adds a different angle to the same idea. Instead of asking candidates to teach a work-related topic, he asks them to teach something they genuinely care about:

“The one piece that I do want a fresh build on is for presentation skills. 

I like to have candidates create a 15 minute presentation to teach us something they are passionate about that is NOT work related. 

We get to know them as a person, see how they apply enablement skills in a new way, and it generally brings out excitement for subject matter from the candidate. 

One that sticks out to me was someone who taught us the importance of each role in the circus. 

For this I share a rubric ahead of time to align the panel and the presenter on what we want to see. ”

What Kyle is assessing is not the topic at all – it’s how the candidate brings others with them.

A strong facilitator can make an unfamiliar subject feel accessible, relevant, and engaging.

A weaker one talks at people and hopes the content compensates.

This kind of exercise makes the underlying skills unmistakable:

• Do they create a sense of shared exploration rather than a one-way lecture?
• Do they help others follow their thinking, not just hear their words?
• Do they make the learning moment feel alive, even when the subject is personal or unconventional?

And then there’s Daryl Spreiter, who makes facilitation non-optional as the wrap-up part of his exercise we covered as part of the first theme:

“…reserve at least 5 minutes for an interactive exercise to show us how you would engage the team during training.”

Most interview processes test whether a candidate knows the content.

Daryl tests whether they can bring people into it.

Anyone can advance through slides, but very few can shift the room’s energy, spark involvement, or make learning feel active rather than passive.

What the facilitation exercises ultimately reveal

A strong enablement candidate is not defined by how well they perform a session, or how polished their slides appear.

They stand out because their delivery creates understanding, participation, and movement in the room.

Across all the examples, Theme 3 helps you see whether a candidate can:

• Teach with clarity – not by dumping information, but by organising it, simplifying it, and making it land.
• Elicit active engagement – as Sheryl and Daryl both surface, can they pull people into the learning, not just speak at them?
• Make learning stick – as Felix and Kyle’s exercises show, can they break ideas down, check understanding, and help others absorb and use what they’ve learned?

These abilities tie directly back to the earlier themes.

Strategic thinking sets the direction. Programme design builds the structure. Facilitation determines whether the learning inside that structure takes root.

It is the part of enablement where ideas begin to take shape in people’s minds – where concepts start turning into skills, and where a programme moves from plan to lived experience for the field for the very first time.

Facilitation doesn’t create behaviour change on its own, but it initiates it. It sets the tone, establishes the foundation, and prepares people for the practice, reinforcement, and repetition that come later.

And while facilitation is often associated with the classroom moment, its reach is broader.

The same abilities – clarity, presence, and the skill to bring people with you – also shape how you communicate with stakeholders, gain buy-in, and keep a programme aligned across teams.

In other words: design gives a programme shape; facilitation gives it life.

Theme 4 – Adoption, reinforcement, and sustaining behavioural change

Many candidates can design and deliver a programme.

Far fewer know how to help it take root in the field.

Facilitation introduces ideas and skills, but adoption is what carries them forward.

Real enablement shows up long after launch day – in week five, month three, quarter one – when enthusiasm fades, and habits tend to reassert themselves. 

This theme focuses on the quiet, ongoing side of enablement: sustaining behaviour change, building reinforcement into the system, and keeping a programme alive once the classroom moment is over.

What adoption-focused exercises really evaluate

Strong exercises in this area help you see whether a candidate truly understands what makes change stick in the field.

They show whether someone:

• Understands that training ≠ adoption
• Builds reinforcement into design instead of adding it afterwards
• Knows how habits form – slowly, socially, through repetition
• Measures behaviour change, not attendance or slide count
• Keeps enablement alive when the launch excitement disappears

Adoption is the bridge between learning and performance.

And it is where many candidates expose a gap – not in intent, but in their grasp of how behaviour changes over time.

Several leaders touch on this indirectly, especially in the second half of Amy McClain’s exercise, where the real question is not “How would you build it?” but “How will you know if it’s working?”

Most interviews stop at the build.

A better interview goes further:

• How would you measure adoption?
• What would you do if the behaviour doesn’t show up?
• What assumptions are you making about why people will use it?

This shift – from creation to continuation – is the heart of a more holistic and effective enablement approach. 

Some contributions implied adoption without naming it, like in Liz McCune’s product-launch scenario:

“Have the candidate create an enablement plan for the product launch detailing what would be needed, timing etc and the plan to work cross functionally within the organization…”

A mediocre candidate lists assets.

A successful sales enablement manager maps continuity – what happens after the launch moment:

• A clear reinforcement rhythm, not a single event
• Post-training checkpoints and manager coaching, so new skills do not stall
• Early-win sharing, to normalise success and build social proof
• Manager-led habit building, not reminders that disappear in inboxes
• Feedback and refinement loops, where field insight shapes the programme over time

Andrey Zevakhin, Senior Director of Sales Enablement at an insuretech company, removes all theoretical safety with his exercise suggestion:

“Anything related to hosting hands-on exercises (role plays, sandboxes, etc.) or projects driving adoption (i.e., you have a sales play no one is using, how would you drive adoption).”

His prompt introduces the hardest adoption question in enablement: what happens when the field does not use what you built?

This is the scenario every seasoned enabler eventually faces.

Andrey’s exercise forces candidates to confront it directly.

A junior hire assumes the problem is awareness.

A mid-level hire responds by immediately trying to build a more successful sales training program.

A senior practitioner slows down and asks different questions:

• Why isn’t the field using it?
• Which behaviour would need to change for adoption to happen?
• What friction is blocking that behaviour?
• How are managers supporting (or undermining) reinforcement?
• What indicators would show whether momentum is building?

This is the real work of adoption.

It is not about the asset itself; it is about the behavioural mechanics required for people to act differently.

Andrey’s scenario reveals whether a candidate understands that.

Cori Hartje, Adjunct Professor of Business at Northwest University and a seasoned enablement leader, captures another angle of adoption – not the programme, but the behaviour that shows up under pressure in front of a customer.

Her test looks simple:

“Spend 5 minutes asking about objection handling. They could do a mini lesson or demonstrate real time.

• Let’s talk about objections. What do you see as the value of hearing an objection from the customer?

• What would you suggest the rep learn how to respond?

• Customer says, ‘your price is too high.’ What do they say?

If they don’t come back with steps like: acknowledge the statement, explore the reasons, or ‘compared to what?’ they should have an idea how to respond without argument.”

On the surface, this is about objection handling.

But what Cori is really testing is behavioural coaching intelligence.

She wants to see whether the candidate can guide a rep toward skilled behaviour rather than just recite a technique.

And the split becomes obvious very quickly.

A candidate who only knows theory will speak in generalities:

• “Validate the customer.”
• “Ask good questions.”
• “Handle the objection positively.”

All vague direction, no behaviour.

A candidate with real behavioural enablement experience will do something very different:

• Reframe instead of defend,
• Stay curious instead of rushing to discount,
• Model language the rep can mirror immediately,
• Break the response into clear moves the rep can actually use in a live call.

This is the kind of coaching that drives adoption, because it lives in real conversations – not in slides.

Objection handling is only the area of focus in this specific example, and it could easily be something else. 

The real test is whether the candidate can instruct and coach around a behaviour that is observable, repeatable, and usable tomorrow.

Cori’s brief exercise makes this visible in minutes.

Continuing on the adoption thread, Amanda Maddox, Director of Sales Enablement at an AI orchestration platform, introduces the most realistic scenario of them all:

“Pretend you rolled out a MEDDICC training three months ago and are not seeing the level of adoption you would like. I would ask them to share their recommendations for reinforcement and have them clearly outline any assumptions they make in the process, as those are often just as valuable to understand their foresight and experience.”

Amanda’s scenario highlights something most interviews miss:

The real work of enablement begins after the rollout of the sales enablement initiative, when you inherit whatever happened – or didn’t happen – in the field.

Her scenario forces candidates to sit inside that reality. They must grapple with:

• Post-launch drag (the most common failure point in enablement),
• Diagnosing low adoption once the room is empty,
• Whether their reinforcement plan is intentional or reactive,
• Whether they make assumptions explicit instead of pretending to have perfect information.

Weak candidates jump straight to fixes.

Strong candidates slow down and examine the gap between training and actual field behaviour. They ask:

• Did managers reinforce the behaviours or slip back into old habits?
• Is the material relevant enough to earn its place in real conversations?
• Are reps using the methodology or only recognising the terminology?
• What evidence shows whether the behaviour is embedding or fading?
• Which assumptions must be checked before any solution makes sense?

Amanda’s scenario brings one vital truth into focus:

Adoption is not measured on launch day; it is measured by who is still using it three months later.

And a candidate who can talk through that problem with clarity, calm, and structured thinking is not guessing.

They have lived the cycle, learned from it, and carry the kind of experience that will help them produce meaningful change in the organisation. 

Key takeaway from this theme

At senior levels, enablement is judged not by the materials you ship but by the behaviours that continue after the launch.

So the real questions behind this theme are simple:

• Can they drive change after the room empties? Not deliver once – sustain momentum. 
• Do they design reinforcement as a system, not an emergency? Cadence, coaching, measurement — built-in, not added later.
• Do they understand that adoption is the product? Training is the spark. Behaviour is the fire.

Conclusion

The exercises we’ve examined in this piece across the four main themes test how a candidate operates across the full arc of enablement:

• Can they think clearly when the brief is ambiguous? Theme 1 shows whether they diagnose, probe, sequence, and build direction before acting.
• Can they turn insight into a structured programme that holds up in the field? Theme 2 exposes how they design for learning, relevance, and long-term support of sales enablement efforts.
• Can they bring that programme to life in a way people understand and remember? Theme 3 reveals whether they can teach with clarity, adapt to the room, and create real engagement.
• Can they make the work stick once the classroom moment is over? Theme 4 shows whether they understand adoption, reinforcement, and how habits form over time.

The exercises shared by the leaders in this article evaluate capability, judgement, and practical maturity.

They help surface how a candidate thinks, designs, teaches, and sustains change when the situation is not linear, when information is incomplete, and when outcomes depend on behaviour, not decks.

And they highlight a simple truth:

Enablement is not defined by what you launch on day one; it is defined by what continues to work on day ninety.

So when you evaluate your next candidate, the real questions are not:

• Can they build content?
• Can they run a workshop?
• Are they familiar with sales enablement technologies?

Most can.

The more important questions are:

• Would this person create clarity where there is noise?
• Would they help the sales organisation perform better, not just feel organised?
• Would the behaviour in the field shift because of how they design, teach, and reinforce?

If the answers are yes, then you are not just hiring someone who can do enablement.

You are hiring someone who can strengthen the entire revenue system around them.

And that is the outcome every enablement leader is truly after.