5 Ways to Create a Strategic Partnership with Your Executive Assistant

This post first appeared on the Herg Life blog by Adam Hergenrother on April 28, 2016.

Several years ago, I had a very real conversation with my Chief of Staff. She needed her next growth opportunity and was not sure if her needs could be fulfilled with me and at our company. That conversation has made me examine myself as a leader and provided me with my own growth opportunity. That conversation was also a testament to the trust and loyalty we have established over our years of working together. Many people would have been looking for jobs for 3 months and then started the conversation by giving their two week’s notice. Hallie does not want to leave my organization and I don’t want her to either! But things needed to change. So we discussed those issues and worked on a 90-day plan to get her into her strength zone. She has dedicated years to me and my vision, and in turn, I have dedicated myself to constantly be increasing my leadership lid for her and all of my team members. That is a strategic partnership.

Let’s talk about one of the most important relationships any executive will ever have – the relationship with their assistant. The assistant role today is far different than it was 50, 20, even 10 years ago. Most assistants are now fulfilling several roles at once and often assisting more than one leader. Whatever their title, Special Assistant, Chief of Staff, Executive Assistant, Coordinator of Chaos, they are force multipliers and finding a talented assistant is crucial to the success of your business. Perhaps even more critical is challenging that assistant and helping them grow in order to keep them (see paragraph 1).

At my first post-college job as a commercial underwriter, I had an assistant right away. I wasn’t exactly sure how to navigate that relationship and often had her fetching me coffee, filing, and faxing documents for me. That’s what assistants do, right? After I was fired from that job and started my career in real estate, I started to really understand the importance of leveraging to a great assistant. It wasn’t just handing off miscellaneous tasks, it was creating a mutually beneficial relationship. I focused on sales and my assistant focused on her strengths – handling marketing, client services, and creating systems and processes to make my business run smoothly, which was good for business for both of us.

Hallie pisses me off almost daily (don’t worry, I’ve told her this before and she reads my blogs before they go live), but that is a GOOD thing. If you don’t have someone you trust who is challenging your thinking and pushing you to be a better leader, then it’s probably not the right relationship.

While she supports me daily, I don’t think of her as an “assistant,” but rather a strategic business partner. Whatever projects I’m working on or decisions I’m making for the organization, she is privy to and part of the process. She protects my schedule, maximizes my time, and maximizes my reach by acting as an extension of me at all times. When she speaks, she is speaking on my behalf and I trust her to do so.

Now, this didn’t happen overnight. Hallie was hired in 2010 as an entry-level assistant and both of us have grown tremendously over the past 5+ years. We went from 2 companies in Vermont to 6 companies spanning 8 states. We’ve both made mistakes (a lot of them), made sacrifices, and learned a lot over the years, but we have done it together. What I’m trying to say here, is find yourself a Hallie.

Here are 5 Ways to Create a Strategic Partnership with Your Executive Assistant:

Give Up Control

You, yes you, control freak. You must give up control in order to allow your EA to shine. Believe me, you can definitely NOT do it better than a great Executive Assistant. A great EA will help you delegate and pull work away from you (and not let you have it back). A talented EA will not tolerate being micro-managed and in fact, will end up leading you. If you don’t give up control over every email, every meeting, every marketing piece, etc., then 1) You are the assistant and should not have made a hire in the first place or 2) Your assistant will leave and find an Executive that will allow him/her to do their job and do it well!

The hardest part for me was giving up control of my calendar. Every time Hallie scheduled something for me, I felt like I was being locked in a cage and then slowly tortured. I didn’t want anyone telling me what to do or where to be. But it made me more purposeful. We meet regularly to discuss priorities and to delegate meetings to other team members to make sure my day remains strategic and I’m only spending time on those things which matter most – but she is well aware of what those things are and plans accordingly. You’ll never see someone’s full potential or allow them to grow if you don’t give up control. And then before you know it, things will just be handled and taken care of and you won’t even have known you needed them done! Giving up control gives you the space to focus on your 20%.

Bring Them Into Your Inner Circle

Your assistant works WITH you, not FOR you. Hallie reads all of my emails, attends the majority of my classes and trainings, listens on calls, and sits in on meetings. She is more effective when she knows what I know, knows how I think, how I solve problems, and what I have decided and promised (so she can follow up and deliver). Do not keep your assistant on the periphery, assigning tasks that have no context or meaning. They will be far more invested in your success when they are a part of the entire process, and eventually part of the decision-making or even making decisions on your behalf. When you bring your assistant into your inner circle – everyone wins.

Meet/Communicate Regularly

Whether you’re on Slack, emailing, texting or getting on the phone, I don’t care what form of communication you use, just make sure you are communicating with your assistant regularly. Hallie and I email constantly and also have one face-to-face goal setting/priorities meeting each week. Our offices are right next to each other, so if she allows me any breaks in my schedule, I will share an idea or follow-up on a project in person in between meetings. Regular communication will make sure you are always on the same page. Priorities shift constantly and what may have been important on a Monday, may not be by Wednesday. In order for your assistant to do their job effectively, they must know of these changes so they can adjust, reschedule meetings, or stop working on said project and shift to the other one. Cut down on chaos and communicate!

Set Clear Goals, Expectations and Wins

When you’re working with your marketing team or your sales staff, the goals are pretty clear: hit your numbers. X number in sales volume or X number of leads generated or X ROI. Simple, right? Well, what about the goals and expectations for your assistant? How do they know they are meeting your expectations? How do they know they are winning with you?

Every EA/Executive relationship is different and no two EA jobs are exactly alike. The EA role is largely determined by who their executive is and what needs they have. So I while I don’t have an exact goal or “win” for you to implement with your assistant, make sure you have one. Discuss it and get your assistant’s buy-in.

Maybe it’s the number of client reviews you receive on an online review site each month. Maybe it’s ensuring that employee morale rating is at 90% at all times. Or maybe it’s simply that emails are caught up on and there are no outstanding action items at the end of each week. The point is to have some sort of standard that your assistant can work on achieving and exceeding. Take it a step further and also outline clear “rewards” (bonuses, tuition reimbursement, equity, etc.). No matter how awesome you are, your assistant will likely need more inspiration and motivation than simply serving a CEO.

Make Building Trust a Priority

Trust and loyalty are the cornerstone of a successful EA/Executive relationship; do not just assume it will happen. It will not happen overnight, but it is so important to cultivate it at every opportunity with your assistant. Do what you say you will. Be accountable for your words and your actions. Do the right thing and admit your mistakes. Never throw your assistant under the bus for a mistake you made (though often they will willingly accept blame and not mind taking one for the team). Be honest (sometimes brutally so) and vulnerable and create an environment where your assistant can do the same. Do not allow others to strong-arm your assistant. Support your EA, the way they support you. You must have each other’s backs in order for a true partnership to exist.

Now, excuse me while I email Hallie to figure out what I’m supposed to do next now that I’m done writing this blog.

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