How to Find a Virtual Assistant Who Actually Gets ADHD
Avigail and I found ourselves aligned on the painful internal narratives that keep ADHD entrepreneurs from reaching out for assistance.
Where our conversation really landed was the shared understanding that the key to sustainable business growth as an ADHD entrepreneur is dismantling the productivity shame and customizing support to fit the real needs behind our businesses.
Hiring Virtual Assistants that Actually Work for Your ADHD Brain
I've coached hundreds of bright, brilliant entrepreneurs who are neurodivergent like me—creative, driven, ambitious, and yes, often overwhelmed by the everyday operational details of running a business. I recently sat down with fellow ADHD entrepreneur Avigail Schondorf for an honest conversation about one of the trickiest pulls for ADHD solopreneurs: hiring a virtual assistant (VA)—and, more importantly, hiring one that actually works for your ADHD brain. Understanding neurodivergent communication and leadership means knowing how to get the executive functioning help we actually need.
Let me be straight: I've watched far too many entrepreneurs, myself included, white-knuckle their way through every last admin detail, fully convinced that doing everything alone is somehow a badge of honor. Is it a stubborn streak? Rugged individualism? A baked-in doubt that anyone could ever support us the way we need? So often, we suffer in silence, convinced that asking for help (or worse, hiring it) is a sign of failure, or a waste if it doesn't work out.
Avigail and I found ourselves aligned on the painful internal narratives that keep ADHD entrepreneurs from reaching out for assistance. She names the core myth with striking clarity: the belief that a "bad solution is worse than no solution at all." It's an attitude rooted in the lifelong experience of asking for help and not getting it—or, just as often, having that help arrive in the wrong form, leaving us feeling misunderstood and, over time, ashamed.
It's not just the fear of wasting money on ineffective support that gets in the way, but the emotional toll of being repeatedly misunderstood, which Avigail so aptly described—the repeated disappointments, the sense that maybe "what I'm asking for doesn't exist." The fear of disappointment and perceived unworthiness blocks action, even when the status quo is unsustainable.
Avigail’s perspective on this issue is unique and invaluable. As someone who specializes in helping ADHD entrepreneurs find and integrate the right kind of support, she's seen both sides: the client desperate for help but unable to articulate what they need, and the virtual assistant waiting passively for instructions that never come. She spotlights a common failure mode: we hire a VA thinking we'll "double our capacity," but our actual executive function challenges (planning, prioritizing, delegating) become amplified. Instead of relief, we end up facing shame, indecision, and avoidance, paying someone to do essentially nothing—because we're paralyzed by the tasks of onboarding and delegation that remain so difficult. This is where effective communication and leadership becomes essential.
I've had that very scenario: the guilt of not having enough "delegatable" tasks at hand, the anxiety of paying for support but still drowning in to-dos. The truth is, it is easier to "just do it myself"—for a while. But as Avigail reminded me, doing it yourself works in the short term; it's not sustainable as a long-term business model, especially not for female entrepreneurs with ADHD.
On the subject of when is the right time to hire a VA, Avigail takes a nuanced stance. Traditional business advice says to wait until you can comfortably afford the ongoing expense and have the bandwidth for onboarding. But for ADHD entrepreneurs, she articulated a deeper threshold: it only makes sense to hire a virtual assistant when you're ready to ask for what you need without shame—even if it means letting someone help manage the "basic" executive functioning tasks. She described, refreshingly and without apology, the practical roles her own assistant plays: medication reminders, self-care check-ins, even tracking her follow-through on promises after client calls. This is not typical VA territory, but it is the executive functioning help that actually works for her ADHD brain.
That silent yearning for someone to track the details, nudge us gently (not bossily), and take data input off our overloaded brains is what we actually want—but admitting it takes radical acceptance. As we explored, it's the practice (not just the permission) of self-acceptance, minus the shame, that makes this level of delegation possible.
I posed the question: does an effective virtual assistant for an ADHD entrepreneur need to have ADHD themselves? Avigail Schondorf drew a distinction—executive assistants should not have ADHD, to prevent doubling up on the same weaknesses. However, for certain tasks where "being a mini-me" is valuable—a customer success VA, for example—her own team includes people with ADHD, so they can better intuitively serve the role. But for the central role of executive functioning help, she advocates for someone with proven skills in regulated communication and operationalized thinking—traits not specific to neurotype, but to comprehensive training and mindset.
We also talked candidly about cultural factors, specifically the Filipino BPO workforce. I shared my positive experiences: the service orientation, family values, and educational background that make Filipino assistants such a popular choice. Avigail agreed, highlighting both their immense strengths and the flipside—the tendency to say "yes" to everything, even when clarification or pushback would serve everyone better. Here, our exchange turned practical: it is up to the entrepreneur to train and invite that pushback, explaining that questions or constructive "no's" are signs of collaboration, not disrespect. This process, we agreed, isn't automatic, but when achieved, it creates a partnership where both parties can grow and thrive. This is communication and leadership in action.
Where our conversation really landed was the shared understanding that the key to sustainable business growth as an ADHD entrepreneur is dismantling the productivity shame and customizing support to fit the real needs behind our businesses. Looking for a unicorn VA who can do everything—copy, design, admin, marketing—is an extension of the same fantasy that we should be able to do everything ourselves. Avigail’s solution—placing teams of specialists, each staying in their lane and managed with operational clarity—solves not only the hiring problem, but also the burnout of "breaking" our unicorn hire with overload (something both of us had done in the past).
Finally, Avigail reframed the essential reality: for ADHD entrepreneurs, "binary time" is real—there's "now" and "not now." Ambiguous timelines, like "Tuesday," don't work. The best VAs operationalize language and deadlines, helping us translate fuzzy intentions into concrete action. It was liberating to hear her say, without judgment, what so many of us feel: when we work with people who accept and embrace our quirks, we perform at our best—and reward that trust with fierce loyalty and gratitude.
I'm reminded that the journey to "getting the help we really need" begins with permission—permission to ask for what still feels "stupid" or "small," and to recognize that executive functioning help isn't a weakness, but a competitive asset. My conversation with Avigail revealed not just alignment in perspective, but a dynamic and honest exchange that challenged my assumptions and offered a clearer, shame-free path forward for all ADHD-ish™ entrepreneurs ready to get the right support and grow on our own terms.
Feel free to DM me on LinkedIn or send me an email at diann@diannwingertcoaching.com. I'd love to hear your thoughts!
If you'd like to hear the full episode on the ADHD-ish ™ Podcast, you can do that here.
