Executives—It's Not Them, It's You

Good. I have your attention.

If you thought this post would be about dating or politics, those are conversations for another time.

This one is directed towards you—The Executives with Assistants.

Specifically, those who have “gone through” an Assistant—or six, or eight—and just “haven’t had good luck…” 

…who don’t spend a cumulative hour with your Assistant each month simultaneously wondering why you’re “not getting anything out of them…” 

…who “don’t get it” when your colleagues talk about how much their Assistants have helped them focus on their priorities while yours just “does your calendar and manages your inbox…”

…who only use their Assistants to do your calendar and manage your inbox…

From me to you, with love: It’s not them. It’s you.

Here’s the thing: Executives come to me to hire the right Assistant (which I can…every time 😉😉) because their only explanation for why this “isn’t working” is that they “aren’t hiring the right person.”

I ask them how much time they spend with their Assistants. The answer is, “When I have time.”

I ask, “Why do you need an Assistant?” or “What are your goals for having a great Assistant?” Some can barely articulate it.

They answer “What would move the needle forward for you in your business?” with “if the little things get done.”

From me to you, with love: It’s not them. It’s you.

Here are five ways you’re sabotaging success with your Executive Assistant.

1) You don’t understand the role of an Assistant (and/or you don’t care to learn about it).

So, what exactly does an Assistant do?

If you’re an Assistant, you’re chuckling right now because you hear this weekly. Most people don’t know how administrative professionals advance the mission and goals of the organization.  

(Although, the question isn’t too surprising since we’re often only articulated as “unicorns” and “magic makers”… As much as I hate to admit it, we’re not.)

Assistants are real humans with exceptional talents that very few people possess. We can not only transform “the work,” we can also transform “how you work.” We’re insanely resourceful, enterprising, and hardworking.

Tip: If you don’t know what an Assistant does, ASK AN ASSISTANT. If you don’t know what to delegate to your Assistant, set up a 90-minute meeting with them and run through your day, your pain points, what takes you too much time, and what you don’t need to be doing anymore but have been afraid to ask them to do. Tell them why you need certain tasks done and let them figure out how to get them done.

You can also ask someone like me to explain it to you. Or Google it.

2) You don’t understand that it takes two to tango.

This isn’t just another hire—it’s a transformative step for becoming more efficient and effective.

Executives who invest in a strong Assistant partnership experience a productivity boost of 20%-50%. A capable Assistant unlocks your ability to focus on your core responsibilities and priorities.

But here’s the truth: none of this is possible without your effort.

This partnership thrives on alignment, communication, and mutual respect. If you don’t give it the investment it requires, it will fail. Think of it like buying an expensive, gorgeous plant and never watering it. No matter how much you paid for it or how stunning it looks, it will wither without attention.

Tip: This professional relationship is unlike any other. It’s not the type of role where you give your orders or share your ideas and walk away, and things get done without you. It’s a partnership. Sit down with your Assistant to review your goals and plans. Figure out actionable and achievable ways of strengthening your own mini-department.

3) You don’t give them your time or energy.

While it’s impossible to predict the full potential a business or executive can achieve with a strong assistant partnership because the impact is truly infinite, I can say with absolute certainty that this process will fail if you do not spend time with humans.

Texts and Slack messages won’t cut it—your Assistant needs to hear your tone, see your expressions, and understand your context. They need to know your priorities, your future visions, and your most important to-dos for the day/week. You will get better results if you communicate often as you move through your projects and objectives, eventually relying on them and trusting them to arrange your administrative needs accordingly.

Tip: Make time for a minimum of one hour of verbal interactive communication every week.  

Being “too busy” isn’t a valid excuse. This isn’t about squeezing time into the cracks of your schedule; it’s about making deliberate efforts to build trust and alignment. The good news? That investment will pay off in ways that will transform how you work.

4) You give them outdated and busted-up tech.

Outdated technology significantly hinders productivity and efficiency in the administrative profession.

I have heard countless stories of senior Executive Assistants in the C-suite receiving junk PCs from 2012 with jelly stains on them. The sound doesn’t work. It doesn’t have a camera. It’s 15 pounds (19 with the bag). When they open certain software, they get the spinning ball of death because the RAM can’t process the 2025 technological needs of the organization.

Tip: Stop the insanity. If they need to keep up with you, they also need the technology to do so. Let’s stick to technology within the last five years.

5) You don’t set them up for success with your team.

I saved the most important for last. Your Assistant is, and should be, a representative of you to your direct reports, boards, and teams. They will likely be the conduit of information for all those people somewhere around 23 times a day. 

For this to be most successful, your Assistant needs a strong introduction to your VIPs and team BEFORE they join your organization and THE WEEK they join your organization.  This declaration should be explicit, relaying your reasons for hiring this important human as well as what level of trust and support they should receive. 

Relationship building is likely a super strength of your Assistant anyway, so leave that part to them.  Your job is to onboard them with intention and support them publicly often.

Tip: The way you introduce your Assistant and include them in the team dynamic sets the tone for their role. Your team will take their cues from you—if you respect and prioritize your Assistant, others will follow suit.

In conclusion…

A lack of alignment, time, and respect for the Assistant role and partnership is a proven recipe for disaster. I’ve seen this technique attempted one too many times…and those ingredients don’t work. 

If any of this resonates with you, let’s talk—I’m here to help you figure it out.