92: Own Your Role: How OBMs Can Show Up Like a Leader with Gwen Bortner

May 12, 2026

Most OBMs think their job is to take things off the CEO's plate. Gwen Bortner — business advisor with 40+ years of working alongside women entrepreneurs — would push back on that. Your job is bigger.

In this episode, Ashley sits down with Gwen (founder of Everyday Effectiveness and co-host of The Business You Really Want) to unpack what it actually looks like to show up as a leader inside your client's business. Not a task manager. A thought partner with a seat at the table.

Here's what we get into:

• Why your most valuable strategic contribution isn't more ideas — it's helping your visionary CEO sift through the ones she already has and stay focused on the path she said she wanted
• How to ask the hard questions — "Did we switch paths on purpose, or did we get distracted?" — without them landing as criticism (Gwen's trick: talk about the issue, not the person)
• The real definition of accountability — and why most clients say they want it until they actually have it
• What to do when your CEO keeps missing the same deliverable — and why redesigning the work beats nagging her every week
• Why "strategy mode" and "task mode" need to be two separate hats, and how trying to wear both at once dilutes both
• Gwen's SOP philosophy: document the 20% that gets you 80% of the way there, never duplicate information across systems, and stop writing instructions for things the right hire should already know

This one is full of language you can take straight into your next client conversation. Pen ready.

Find Gwen: everydayeffectiveness.com | The Business You Really Want podcast at thebusinessyoureallywant.com