Troubleshooting Enablement – Details, episodes & analysis

You're using AI every day. But when leadership asks for your strategy, you freeze.

This month, Melina Giakas, Head of Enablement at Clay, joins me to break down how to stop operating in piecemeal mode and start connecting your AI work to real business outcomes.

We dig into:

• Why AI ownership is one of the biggest opportunities for enablement right now
• Building a custom GPT for real-time coaching when managers are stretched thin
• Using deal data to build a case for your programming
• The critical thinking trap: what happens when automation fills in the fields but reps can't defend their answers
• The unsexy stuff (templates, content governance) that makes AI actually scale

Guest: Melina Giakas, Head of Enablement at Clay

Follow Melina on LinkedIn: https://www.linkedin.com/in/mgiakas/

Planning a sales or revenue kickoff with a tiny enablement team and massive expectations can feel impossible:

• Leaders want a world-class experience.
• No one wants to make decisions.
• Everything funnels back to enablement.

In this episode of Troubleshooting Enablement, Devon McDermott is joined by Ali Smith (Senior Manager of Customer Success Enablement at Recharge) and Callan Coles (Global Sales Enablement Leader at Branch) to break down how to take control of an RKO or SKO when you have influence but limited authority.

They share hard-earned lessons from running in-person, hybrid, and virtual kickoffs on small teams, including:

• how to align leaders
• set boundaries
• lock decisions
• and design an event that actually changes rep behavior

If you are eight weeks out (or LESS), drowning in opinions, and worried enablement will take the blame, this episode gives you a practical path forward!

This week, we’re diving into a deceptively tricky question: How do you know when a company is actually ready for enablement… and when they’re just looking for someone to clean up the mess?!

Joining Devon is GTM powerhouse Michelle Pietsch, who’s built and scaled revenue teams at Datadog, Drift, and Dooly. Michelle shares real talk from the other side of the hiring table, including what it really means when a founder says they “believe in enablement.”

Question: How do I know if a company is truly ready for enablement?

Guest: Michelle Pietsch, GTM leader BeaconGTM

Topics:

- Red & green flags in CROs and founders

- Interview questions that reveal true buy-in

- The tipping point for bringing in enablement

- Shifting from reactive to strategic work

Resources & Links: Follow Michelle on LinkedIn

When your workplace turns toxic but you can’t afford to leave, how do you protect your mental health, show up for your team, and avoid losing yourself in the process? Author and behavior change expert Lauren Brownstone joins Troubleshooting Enablement to explore self-regulation, gaslighting, burnout, and how enablement can challenge harmful dynamics and shape healthier cultures from within.

Question: How do I survive a toxic work environment when I can’t leave yet?

Guest: Lauren Brownstone author of Enabling Enablement

Topics:

- Responding vs reacting in high-stress environments

- Gaslighting, bullying, and burnout at work

- How enablement influences culture and behavior change

- Practical habits to protect your energy and sense of self

Resources & Links:

- Follow Lauren on LinkedIn

- Learn more about Heartwise Self-Leadership

- Buy Enabling Enablement

You’ve done great work. You’ve applied everywhere. You’re still not landing the job. What gives? In this episode, Samantha Thompson, award-winning enablement leader and founder of the enblr, breaks down how to navigate the job search slump, tell better impact stories, and rebuild confidence when the rejections keep coming!

Question: I keep getting rejected for enablement jobs. What am I doing wrong?

Guest: Samantha Thompson, SEC One to Watch, founder of the enblr

Topics:

- Resume mistakes that cost you the interview

- Crafting compelling enablement impact stories

- Red flags in interview processes

- Assets worth bringing (and when to protect your time)

Resources & Links:

Follow Samantha on LinkedIn

Explore https://www.theenblr.com/