Great, so what should enablement look like?

In my view, modern enablement isn’t about delivering more content or piling on another training session. It’s about engineering sales performance. That’s why I use the term Sales Performance Architect in Chapter 10 of my book Just-in-Time: The Future of Enablement in a World of AI, because the job is about building systems that scale behavior change, not just checking the “enablement” box.

And when you’re hiring a sales enablement leader, this is the mindset and skill set you’re looking for, not just a traditional sales enablement job description, but a true architect of performance.

The 5 skills of a Modern Enablement Leader (and interview questions to ask in the hiring process)

1. Is a master of Change Enablement (yep, my first criterion)

I believe that enablement, at its core, is about being a change agent. That’s why I’m listing this one first. Here’s the problem: despite all the talk about “change management,” most companies still aren’t very good at it. They pour 90% of their energy into launching the change, the tool rollout, the playbook, the certification, and leave barely 10% for reinforcement. The result? Initial adoption fizzles, behaviors never stick, and the investment falls flat.

Change enablement is the missing piece. It’s not about the launch itself; it’s about creating repeatable, scalable processes that ensure reps actually adopt and sustain new behaviors in the flow of work. A true Sales Performance Architect flips the balance: less time on launch theater, more time ensuring reinforcement, measurement, and habit formation.

Enablement Interview questions to ask:

• Did you have a repeatable change enablement process at your last company? Walk me through it.

• How did you manage both big rollouts (like a sales methodology roll-out) and micro-changes (like a new field or competitive battlecard update)?

• What specific steps did you take to ensure adoption two months after launch?

Yellow flags to look out for:

• Talks about six-week certification programs as their primary approach (too slow for today’s pace)

• Over-indexes on upfront training sessions with little mention of reinforcement.

• Describes change as a project, not as an ongoing process.

2. Knows data (doesn’t just rely on RevOps)

If change enablement is the heart of the Sales Performance Architect role, then data is its brain. Sales leaders rely on Revenue Operations for strategic go-to-market insights — like capacity planning, territory optimization, and technology choices. They need the same caliber of strategic partnership to optimize their most valuable asset: their people.

A true enablement leader treats data not as a nice-to-have, but as the foundation for every decision. They know which reports matter, how to use call intelligence data and rep shadowing to surface real skill gaps, and how to tie adoption and learning back to revenue outcomes. Without this, enablement becomes activity for activity’s sake. With it, enablement earns a seat at the leadership table.

Enablement Interview questions to ask:

• What reports did you review most frequently in your last role, and why?

• How did you connect leading metrics (e.g., ramp time, pipeline creation) with lagging metrics (e.g., win rates, quota attainment)?

• How did you use call recordings (from Gong, Copilot, etc.) to diagnose skill gaps or refine training? Walk me through the kind of analysis you’d run.

• Tell me about a time data forced you to pivot an enablement initiative. What changed?

• How did you share insights with sales leadership? Walk me through your reporting cadence and what was included in those reports.

Yellow flags to look out for:

• Over-focus on activity metrics (e.g., “we ran X sessions, we looked at content views”) vs. performance outcomes.

• Relied exclusively on their counterparts in RevOps for data (ie, didn’t pull CRM reports), enablement must be looking at that data to diagnose gaps and needs.

• Answers rely only on anecdotal feedback (“my reps said they needed this training”) instead of data.

3. “Gets” that enablement must look different now to keep up

Traditional enablement models like your annual SKO, quarterly certifications, or long LMS modules during onboarding simply don’t work in today’s world of goldfish memory, context switching, and cognitive overload. The science of learning (see Chapter 3 of Just-in-Time) shows us that information fades unless it’s reinforced, recalled, and applied in context.

That’s why the right enablement leader won’t obsess over packing everything into a one-time training. Instead, they’ll design reinforcement systems that continuously drip knowledge back to reps in bite-sized, digestible formats. Think: short play snippets, 60-second videos, quick talk tracks, or a single-page battlecard that’s surfaced exactly when and where a rep needs it right in Salesforce, in their inbox, or right before a call.

This leader knows their job isn’t to create massive content libraries or 6-week certifications. It’s to deliver microlearning in the flow of work so reps can apply knowledge in the moment that matters.

Enablement Interview questions to ask:

• How have you used microlearning or bite-sized reinforcement in your past programs?

• How did you address the forgetting curve and ensure training stuck beyond the event?

• What tactics did you use to reduce context switching and deliver knowledge in tools reps already use (CRM, email, call platforms)?

• Can you share an example where microlearning or in-flow guidance directly helped a rep advance or win a deal?

Yellow flags to look out for:

• Over-reliance on big, one-off training events (SKOs, quarterly workshops) with little reinforcement.

• Measuring success by completion rates instead of behavior change or deal impact.

• Designing long, static playbooks or courses instead of modular, reusable, bite-sized assets.

• No clear strategy for reinforcing knowledge where reps actually work.

4. Knows how to win over the hearts and minds of their peers

Enablement fails when it’s siloed. Great Sales Performance Architects know that sales success isn’t just about better decks or one-off trainings; instead, it’s about unifying Sales, Marketing, Product, and CS around consistent messaging, aligned customer experiences, and shared accountability for reinforcing the right behaviors.

The best leaders in this role act as connectors:

• They partner with Product to ensure launches aren’t just announced but actually adopted in the field, with messaging that sticks.

• They collaborate with Marketing to make sure content isn’t just created, but trusted and used by reps in live deals.

• They tap into CS and Solutions Consultants to surface customer insights and build feedback loops into enablement materials.

• And most importantly, they leverage frontline managers as multipliers, ensuring reinforcement happens in 1:1s, pipeline reviews, and team huddles, not just in a training session.

This isn’t about acting as a service desk that takes requests. It’s about driving cross-team alignment and building systems that make adoption inevitable.

Enablement Interview questions to ask:

• Tell me about a time you partnered with Product or Marketing on a launch. How did you ensure reps actually adopted the new messaging?

• What were the most important cross-functional meetings you were part of, and what was your role in them? Walk me through the agenda and attendees.

• How do you manage competing priorities when Sales wants X, Marketing wants Y, and Product wants Z?

• If I spoke with any two front-line managers at your last company, what would they say about your collaboration on enablement initiatives?

• What processes do you use to collect rep and manager feedback, and how do you push updates back out across teams?

• How have you empowered managers to reinforce enablement in their coaching and team meetings?

• Do you have experience running a champions program or sales excellence group? What did that look like?

Yellow flags to look out for:

• Talks about priorities strictly coming from sales enablement as a “service desk” to Sales only.

• Can’t point to real examples of collaboration outside of the Sales org.

• Focuses solely on creating content libraries instead of ensuring adoption and reinforcement.

• No clear process for gathering rep feedback or partnering with managers.

5. Will push the envelope on AI

AI and automation aren’t buzzwords anymore. In today’s Change Economy, your enablement leader needs to be a key partner pushing the envelope of innovation so your team can move faster, not slower. This isn’t about waiting for IT or RevOps to “figure out AI workflows.” It’s about someone who has already tested, experimented with, and integrated AI tools into their own workflows (especially around content creation) and then trained reps and managers to adopt them too.

At its core, enablement is a content-heavy function. Reps need fresh talk tracks, updated battlecards, quick-reference guides, competitive one-pagers, onboarding modules, weekly updates…the list never ends. In most orgs, enablement leaders are drowning in this cycle, stuck creating, recreating, and chasing down duplications.

The right hire breaks that cycle by leveraging AI and automation to do 80% of the heavy lifting. They don’t see AI as a “nice to have.” They see it as the foundation for scaling content without burning out or endlessly adding headcount.

A high-performing enablement leader should:

• Have reusable content systems: They’ve built templates for weekly updates, battle cards, competitive briefs, and sales plays, so nothing starts from scratch.

• Create AI prompt libraries: They’ve curated, tested, and refined a library of prompts reps and managers can use for content creation (e.g., drafting email responses, rewriting talk tracks, summarizing call insights).

• Maintain a content library for the team: A central source where best practices, prompts, and reusable templates live, ensuring reps and managers always have the tools to adapt quickly.

• Scale without headcount: Building repeatable, automated processes that free them to focus on strategy and behavior change, not firefighting.

Enablement Interview questions to ask:

• Walk me through the three most recent AI tools you tested. What did you like/not like about them?

• Walk me through a creative way you’ve transformed content using AI.

• What repeatable templates have you created for content (battle cards, updates, onboarding, etc.)?

• Do you have a prompt library you’ve built and shared with reps or managers? What’s in it?

• How have you used AI to generate first drafts of enablement content? Can you share an example?

• What would you automate first if you had to scale enablement with no additional headcount?

Yellow flags to look out for:

• Examples of AI are limited to ChatGPT for basic content creation. There are TONS of free tools on the market, and if someone hasn’t naturally tested ways to accelerate their workflow over the last 18 months, they’re likely not that naturally curious type.

• No examples of reusable systems; every content request starts from scratch.

• Uses AI only for one-off tasks, not as a repeatable workflow.

• Relies heavily on admins or SMEs to manually tag, sync, or duplicate content.

• Talks about “completion rates” instead of adoption, personalization, or usage in deals.

  
  

6. Knows how to evaluate and implement enablement technology

When you’re hiring a sales enablement leader, one of the most overlooked parts of the sales enablement job description is technology evaluation.

When evaluating enablement platforms, it’s tempting for enablement leaders to default to the “big names” they know that have dominated the category for more than a decade. While beautiful portals was a good model back in the early 2010s, today it feels like dragging your team back into the era of digital filing cabinets (with a prettier UI). Reps don’t have time to click through portals. They need guidance in the flow of work when they’re in Salesforce, Gong, or mid-email with a buyer. If the tool adds friction instead of removing it, reps will bypass it, default to Slack threads, or rely on outdated slides buried in Drive. 

At the end of the day, every enablement platform lives or dies by one thing: rep adoption. The data backs this up. In the Sales Enablement Collective’s 2025 Impact of Enablement Report, 92.3% of enablement and marketing teams using traditional platforms like Highspot, Seismic, or Mindtickle said that less than 60% of their content is ever used. 

The right hire knows how to cut through the noise, avoid shiny objects, and select platforms that actually drive adoption, reinforce change, and deliver measurable ROI and evaluates platforms through two lenses:

1. Will reps actually use it? (Does it live in their workflow and make them faster?)

2. How quickly can we deploy it? (Can we live in weeks without months of IT mapping or admin overhead?)

If a platform can’t pass those two tests, everything else is window dressing. They should know what questions to ask vendors, especially around adoption:

• Ease of Access: Do reps have to leave their task at hand (ie, in their CRM or email) to find content, or does it show up automatically in the flow of work?

• AI automation: Can AI proactively surface the right asset (e.g., case study, template, talk track) based on CRM data, deal stage, or activity without heavy RevOps setup?

• Frictionless Use: Can a rep find an answer in under 10 seconds, even with typos or a natural-language query?

• Reinforcement: Does the tool push updates and reminders into the rep’s workflow, or does it rely on “check the portal when you have time”?

• Buyer Engagement: Once reps find what they need, can they take instant action — share with a buyer, drop into a deal room, or personalize on the fly?

• Proof of Impact: Can analytics show the connection between rep adoption (content views, shares, deal room activity) and outcomes like win rates or ramp time?

Enablement Interview questions to ask:

• How have you evaluated enablement technology in the past? What criteria did you use?

• Which stakeholders did you include in the evaluation process?

• What capabilities matter MOST to you in an enablement platform?

• Can you walk me through a time you decided not to buy a tool and why?

• What reports or metrics did you look at to determine if your platform was actually being adopted?

Yellow flags to look out for:

• Didn’t include reps or sales managers in the enablement platform evaluation.

• Didn’t do a POC to get their reps' hands on the product to get their buy-in.

• Focuses mainly on the admin experience of a platform vs the rep experience for fast access.

• Talks only about content libraries or search, not reinforcement, in-flow-of-work delivery, or buyer engagement.

• No framework for evaluating build vs. buy decisions or aligning tech to business outcomes.

The ugly truth: no one will check every box 

Now, here’s the reality: you probably won’t find a hire who checks every single one of these boxes on day one. In fact, when I shared these ideas on LinkedIn, I called this profile a unicorn (and yes, I did find him!). 

But these are the right enablement interview questions to start asking not only when you’re evaluating a new enablement leader, but also when you’re assessing the strengths, gaps, and opportunities within your current team. Even if no single person can deliver on every front, building awareness around these skills helps you level up your enablement function, align expectations with sales leadership, and move one step closer to truly scaling sales performance in today’s Change Economy. 

PS. If you’re looking to upskill your current team, Just-in-Time: The Future of Enablement in a World of AI is packed with practical tips for Enablement professionals. Inside, I break down how to sharpen data skills, which reports actually move the needle with sales leadership, and how to turn raw insights into action that drives revenue. 

Last but not least: How to partner with your Enablement Leader

Hiring the right enablement leader is only half the battle. The other half is how you position and empower them inside your organization. Too often, enablement is introduced as a “support function” for the team that builds decks or runs SKO logistics. That framing sets them up to fail.

 If you want this hire to make a real impact, here’s how to partner with them effectively:

• Position them strategically. When you announce the role, make it clear to the org that this person is a partner to sales leadership, not just a service desk. Their mandate is to drive sales performance, not just produce content.

• Set clear success metrics. Don’t stop at revenue. Track leading and lagging indicators that reflect enablement’s real impact: rep ramp times, content usage and adoption, search-to-answer success rates, and how consistently managers are reinforcing new behaviors.

• Give them access. Invite them into the rooms where revenue decisions get made, like forecast calls, pipeline reviews, and GTM strategy sessions. Without that visibility, they’ll always be guessing at what matters most to you and to your managers.

• Back them up publicly. Enablement initiatives succeed or fail based on leadership reinforcement. If CROs and Heads of Sales champion and model the behavior, managers will reinforce it, and reps will adopt it. If leaders treat it as optional, so will the field.

Done right, your enablement leader becomes more than a trainer or content creator; they become the change agent who ensures your reps stay ahead of the relentless pace of product innovation, competition, and AI-driven disruption. And when you partner with them at a strategic level, you’re not just “supporting enablement.” You’re investing in your reps, your managers, and ultimately, your company’s ability to win in the Change Economy.