Interview with Leslie Henstock

This week, I'm excited to introduce you to Leslie Henstock, a longtime executive partner and operations generalist who truly thrives in those "all-hands-on-deck" moments! With over 20 years of experience supporting C-suite leaders in every environment imaginable, in-office, hybrid, and fully remote, she's renowned for creating calm in the chaos and being the ultimate go-to person for high-impact projects. Leslie brings a fantastic people-first approach to all she does, from executive support to internal comms and event planning. Fun fact: her background as a professional theater and film actress still shines through in her storytelling and ability to make even the driest update a little more fun. Get ready to be inspired by her heart, humor, and unwavering sense of "we've got this!"

With over 20 years supporting C-suite leaders, mostly in remote or hybrid tech/consulting environments, what's one key piece of advice you'd offer to an EA new to supporting an executive in a fully remote or hybrid setting that they might not find in a job description?

One piece of advice I’d give to any EA stepping into a remote or hybrid role is this: You have to work intentionally to maintain the humanity in your relationships — with your executive and with the broader team. In person, you can sense when your exec is overloaded or energized just by walking past their office. Remotely, you lose those cues unless you create moments to check in, read between the lines, and keep the communication open and frequent. That’s true in reverse too!

Additionally, as the gateway to leadership, you have to stay approachable to everyone else, too. When team members know they can come to you, it helps build trust, transparency, and keeps the whole machine running smoothly. You end up being a key part of the company culture, even through a screen.

It’s not something you’ll see in a job description, but it’s what makes an EA truly invaluable in a remote setting. And not all Execs and Leadership teams may be right for you and vice versa.

Consider the interview with your Exec as matchmaking - do you sense an energy right away you’d thrive working with? Are there red flags with their behavior in the interview? Did they reschedule 5 times? Were they late? Did they only devote 5-10 min to talking to you? Did they speak to you solo or with others? If so, who led the convos? These are all key pieces of data I’d urge EAs to think about in their interview. That is your time to assess them as well as vice versa. Use it!

How do you approach prioritizing tasks and managing demands when everything feels urgent, especially in a fast-paced setting? Do you have a specific system or mindset that helps?

In fast-paced environments, I’ve found that mindset is just as important — if not more — than any task management system. I absolutely use tools and lists to stay organized, but what really keeps things moving is confidence. You have to be comfortable making judgment calls when your exec isn’t available to weigh in — especially when everything feels urgent.

I lean into the “ask for forgiveness, not permission” mindset. Not recklessly, of course, but because I know the business, I know the priorities, and I know my exec. That trust and intuition allow me to keep momentum going without bottlenecking decisions. It’s not something you can do on day one, but once that relationship and context are in place, it’s what makes an EA a true extension of their executive.

At the end of the day, my goal is to reduce noise, not add to it — and that sometimes means making confident choices in the gray areas.

What's your secret to ensuring complex events run smoothly and effectively communicate key messages, especially when balancing virtual and in-person needs?

The real secret to making complex events run smoothly — especially when balancing virtual and in-person elements — is communication, communication, communication. You can have every detail buttoned up, but if the right people aren’t looped in, something small can throw everything off.

I make it a point to over-communicate with clarity, especially with other admins who are even tangentially involved. If their exec is attending, they deserve the same insights I have: what’s going well, what might be a red flag, and what to keep an eye on. I’ll share things like, “This vendor’s been amazing to work with,” or “This person’s been tough to get hold of — heads up,” or “The venue manager swears this room won’t feel tight, but I’m a little concerned.” These notes might not be on the official run-of-show, but they’re what help the whole team stay aligned and adaptable.

It’s about creating a shared brain and giving people context — not just information. That’s what keeps events from unraveling and helps everyone feel more prepared and confident.

You have a background in building and leading onboarding programs for EAs and coordinators. What's one common challenge you see new administrative professionals face, and what practical advice do you offer them to overcome it and truly thrive in their role?

One challenge I see often is that new EAs are onboarded in a bit of a silo — trained almost exclusively by or around their executive. It can create this unspoken territorial dynamic that doesn’t serve anyone in the long run. It limits knowledge-sharing, it isolates the new hire, and it works against the kind of EA-to-EA collaboration that really makes organizations tick.

So my advice is: push against that. If you’re a new EA and you realize you haven’t connected much with other admins yet — don’t wait for an invitation. Take the bull by the horns. Reach out. Ask questions. Offer to compare notes. That network becomes your greatest resource, especially when things get complicated or political.

You’re not just there to support one person — you’re part of a larger system. And thriving in the role means knowing how to plug into that system and make it better.

Being in such a high-impact role, self-care is crucial. With your love for reading, walking, journaling, and being outdoors, how do you intentionally make time for personal well-being and recharge, especially after a particularly demanding week or a major project like a large event?

Self-care in a role like this is crucial — and honestly, it’s also really hard. The truth is, no one is ever going to take care of you as well as you can. Your job can care about you, your team can be wonderful, but at the end of the day, your role is temporary. Your body, your family, your relationships — that’s the stuff that lasts. That’s what you have to protect.

I try to remind myself of that when I’m tempted to work “just a little longer” at the end of the day. Yes, sometimes going the extra mile is necessary — and even rewarding — but I also believe in going the extra mile for yourself.

For me, that looks like prioritizing sleep. Truly, it’s the best medicine. I try to put my phone down before bed and read instead, which helps me reset. And in the mornings, I write down a quick list of things I’m grateful for. It’s simple, but it grounds me — especially when the days are stressful or when I’ve just come out of something intense like a big event.

It’s not about being perfect at it. It’s about being intentional — and giving yourself permission to matter just as much as the job does.

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Leslie Henstock is a longtime executive partner and operations generalist who thrives in fast-paced, all-hands-on-deck environments. With 20+ years of experience supporting C-suite leaders in-office, hybrid and fully remote, she’s known for creating calm in the chaos, tackling high-impact projects, and being the go-to person for dotting the I's and crossing the T's.

Now based in Birmingham, MI, Leslie brings a people-first approach to everything from executive support and onboarding to internal comms, culture-building, and event planning.

Before diving into the world of executive leadership, Leslie was a professional theatre and film actress — a background that still shines through in her storytelling skills, quick thinking, and ability to make even the driest status update a little more fun. Whether managing event budgets or helping new admins feel less alone, she leads with heart, humor, and a strong sense of “we’ve got this.”

Leslie's LinkedIn: https://www.linkedin.com/in/leslie-henstock-044497a4/