most of the time, when someone tells me enablement isn't working, they're not describing an enablement problem - they're describing a leadership decision that was never made.

i've seen this pattern at every stage of scale. a company hires its first enablement leader, or brings in a consultant, or stands up a whole team. and the expectation is that this function will fix things that were never broken by a lack of training.

here's what i mean.

icp definition. if leadership won't commit to who the product is actually for, enablement becomes a game of teaching reps to sell to everyone. no playbook survives that. reps stop following the motion and start pattern-matching to whatever closed last quarter. it looks like a skill gap. it's not.

pricing and packaging clarity. when leadership leaves pricing squishy or lets every deal get custom-scoped, you can train objection handling all day and it won't matter. reps aren't losing on skill. they're losing on confusion. i've watched entire enablement programs get rebuilt because leadership assumed the problem was rep readiness when it was actually pricing chaos.

the strategic narrative. i don't mean messaging. enablement can shape messaging. i mean the deeper story. why this company, why now, why this category. if leadership hasn't committed to that, enablement is building on top of nothing. reps feel it. they start improvising their own pitch because the real one doesn't exist yet.

segment and territory design. if the wrong reps are calling the wrong accounts, no amount of coaching or certification fixes the math. that's a leadership allocation decision. i've seen teams pour months into skill development when the actual issue was that mid-market reps were working enterprise deals with no executive sponsorship path.

manager role definition. this one is close to my heart. leadership says managers should coach. but they don't reduce their reporting load, adjust comp, or remove the five other jobs those managers are doing. enablement gets blamed when coaching doesn't happen. but the structural decision was never made. you can't train someone into a role the org hasn't actually created space for.

what "good" looks like at each stage. if leadership hasn't defined what a qualified opportunity actually is, or what a successful onboarding engagement looks like for cs, enablement is building toward a target that doesn't exist. i've run top performer diagnostics where the highest-performing reps couldn't articulate the company's qualification criteria. because there wasn't one.

when to say no to a deal. disqualification criteria. most leadership teams will enthusiastically approve icp docs but won't actually tell a rep to walk away from revenue. enablement can't teach discipline the org doesn't practice at the top.

the throughline across all of these is simple. they're decisions, not skills.

enablement builds capability. it can't substitute for missing strategic commitments. and the longer those commitments go unmade, the more pressure lands on enablement to compensate. which it can't. which makes it look like it's failing. which starts the cycle of rebuilding the function instead of addressing the actual gap.

if you're leading a revenue org and you're about to invest in enablement, the most useful thing you can do first is ask yourself which of these decisions you've actually made. not discussed. not workshopped. made.

the ones you haven't are where the real work is.

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