5 Ways to Create a Strategic Partnership with Your Executive Assistant

business meeting

Last week, I had a very real conversation with my Chief of Staff (Hallie, who many of you know). 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 the last 5+ years of working together. Many people would have been looking for jobs for 3 months and then started the conversation by giving their two weeks 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 are currently working on a 90 day plan to get her into her strength zone. She has dedicated the past 5 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.

So, in honor of Administrative Professionals Week, 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 over night. Hallie was hired in 2010 as an entry-level assistant and both of us have grown tremendous 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:

  1. 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%.
  2. 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 & 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.
  3. Meet/Communicate Regularly 
    Whether you’re Slacking, 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!
  4. 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 a 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 then simply serving at the pleasure of the CEO.
  5. 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 over night, but it is so important to cultivate it at every opportunity with your assistant. Do what you say you will. Be accountable to 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 willing 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 bully or abuse 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.

This interview with Simon Sinek and his assistant, aka Chief of Simon, Monique Helstrom, very clearly explains the strategic partnership between executive and assistant.  EAs, share this with your Executive, it can be a great springboard to start a conversation with your leader about taking your position (and your relationship) to the next level.

For more great Executive Assistant resources, email hallie@adamhergenrother.com. She is a huge advocate for the Executive Assistant role and has a bunch of resources that can help you either hire a great EA or that will help your EA grow in their position.

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.



One Simple Action for a Competitive Advantage

I love the smell of wheatgrass in the morning. Every morning at 4:43am, I jump out of bed, down a glass of water and a shot of wheatgrass and I’m now ready to start my day.

rise upIf you want to get started on your emotional fitness journey, all you have to do is implement getting up early. That is a pretty good test of your fortitude and resilience. Do not make excuses – like you need X number of hours of sleep or you’re not a morning person. You might not be now, but you will be after 66 days of creating the habit! Stick with it. You will thank yourself later.

The first week or so is not so bad. You’re in the honeymoon phase and excited about your new routine. It’s that second or third Monday when it’s rainy or you didn’t sleep well that you say, “WTF. Why did I start doing this?” That’s when you are really tested and you must recommit yourself to the decision you made and practice your self-mastery, which is overcoming that voice that says no.

I said it was simple, but it’s not easy. If it were easy, everyone would do it. And I know I’m talking to a bunch of high achievers here, not anyone willing to settle for mediocrity, right?

I started getting up before 5am about 3 years ago and it was uncomfortable the first few days, but I quickly discovered I loved it! Every morning before 6am, I had already gotten a “win” for the day. Now, 3 years later, I’m literally excited to go to bed (before 10pm. Okay, fine, I’m usually in bed before 9pm) so I can get up early and start my routine.

Why get up before 5am? Because I, like you, have a lot of kicking ass and taking names to do throughout the day. My personal growth is a priority, so I put that first in my day, before the rest of my business and family responsibilities begin. A lot of people tell me they can’t do this because of their kids. I have two kids (ages, 4, 2 , and one on the way), so that kid thing? I get it. Actually, I was up at 3:45am this morning with my youngest. But did I let him watch TV and veg out? No. If he’s up, he’s drawing, playing with crafts, journaling (yes, he wants to journal because he watches dad do it), or doing yoga. Hey, if they’re up, they’re up. But I don’t compromise my personal development time, nor do I compromise time with my kids.

So what do I do at 5am? Journal, meditate, review my goals and affirmations, and spend some time with my family. You can see my complete daily routine here. This daily ritual of personal development activities gives me the raw energy I need to be the best leader for my company and my family.

The key is going to bed early. What are you willing to say no to in order to get up early enough to work on your personal development? It may mean saying no to that second beer with friends or saying no to finding out who gets the final rose on The Bachelor, but it means saying YES to creating the best life and the best version of you. Sounds like a win to me!

“Early to bed and early to rise, makes a man healthy, wealthy, and wise.”
– Ben Franklin

Turns out, I am incredibly brilliant before 6am and get my best work done then. My creative thinking and problem solving skills are on fire and my brain is tackling challenges at 200 MPH. After that, I focus on putting my ideas to work throughout the rest of the day.

Some of the most successful people get up early. Success leaves clues. And I follow. If the people that I most admire and respect have implemented this habit, then there must be something to it. I know from my own personal experience, it has made me more focused, increased my energy, and made me incredibly purposeful throughout the day. I have gone back to drinking coffee and tea after my no coffee experiment, but I will not go back to sleeping in. There is so much life to live and so much to gain by getting up before 5am!

Additional Resources:

I’m winning the race while others are sleeping. Are you?

Get up, get going, get yours.


It’s Surprising How Few Wins There Are in Business

I’m on a plane (again), so I’m going to make this one short and sweet (I have a few episodes of House of Cards to catch up on). I was on a CEO Super Business Panel on Monday and one of the questions we were asked was, “What was one ‘win’ that you were most surprised by.” And the first thing that came to mind was that it is surprising how few wins there actually are in business.

Building a business is really hard and there are a hell of a lot more challenges every day then there are successes. Success comes in spurts and it’s important to celebrate each small victory, before you get knocked back down. The key is to keep getting back up, keep moving, and making sure you have better quality problems.

“Victory is won not in miles, but in inches. Win a little now, hold your ground, and later, win a little more.” – Louis L’Amour

Look, extraordinary success and mediocrity look a lot alike for a long period of time. In businesses, this is about a 5-7 year stretch. You have to stay focused and work through the grind in order to earn the right to have that geometric growth. Those overnight successes? It took them 5, 7, 10  years to get where they are. You’re just hearing about them now, when they’ve hit their geometric run. What you didn’t see was the long nights, time away from family, stress, and challenges. But as hard as all of that is, I guarantee you ask any of those business leaders and they will tell you that despite the challenges, they were fortified by their goal, their passion for the project, and ultimately their growth. No one would endure the challenges of building a business, if there wasn’t a bigger why, a bigger reason, behind it. Though, I do think entrepreneurs and business leaders might all be a little bit masochistic, since most of them would also say, they are just having fun!

So what can leaders do? Have an incredible support system, constantly work on their emotional fitness, and have a great attorney.

Emotional fitness is so critical to the success of leaders. Without it, many great leaders may have given up and companies like GE, Facebook, Tesla and many many more would not exist. I practice increasing my emotional fitness every day through meditation, my gratitude journal, affirmations, and never letting fear stop me. Here’s a quick article on how to master emotional fitness.

sarah and adam editedAnd I am beyond blessed to have such an incredible support system at home, particularly my wife, Sarah. I could not do what I do, nor would I be who I am today without her unconditional love and support. She effortlessly takes care of our children, our home, our family’s health, vacations, various schedules and activities, and still finds time to serve on several committees at our companies. She is the calm to my storm. Whether it’s friends or family members, make sure to surround yourself with people who understand and support the crazy, challenging, and often complicated path that you’re on.

Yes, being a business leader and building a business is hard, but I wouldn’t have it any other way. Business is nothing more than a conduit for personal growth. Bring on the challenges – it just means I’ll grow that much faster!


P.S. Another question at the panel was, “Where is there an opportunity for entrepreneurs to expand or approve upon.” My answer? Travel. Could someone please invent teleportation?

5 Must Attend Events to Grow Your Business and Change Your Life

I just got back from a mastermind in Austin last week and I’m getting ready to fly to Vegas for a few days of training. I average 2-3 trips a month where I am either attending a private mastermind, a conference, or I am teaching a class. I learned very early on in my career as an entrepreneur and business owner that the best investment is in training and education. Almost 10 years ago when I decided to start my real estate business, I borrowed $8,000 and then spent half of it flying across the country for a Howard Brinton Star Power conference. I knew then, and I know now, investing in your personal and professional development is always worth it.


Training and development are an integral part of my companies as well. We are constantly adding to our internal training calendar. And when we decide to host some friendly sales competitions, the prizes are always tickets to a training event. I can not stress enough to you or to my team – investing in your personal and professional development is never a waste of money. If I had $1,000 left to my name, I would put it into a class that would expand my mind, inspire me, and give me tools to better my life.

To learn more about my upcoming events and classes, check out www.hergtraining.com.

“The best investment you can make is in yourself. ” – Warren Buffett

I couldn’t agree more with the great Mr. Buffett. Here are the events/trainings/meetings that have had the most impact on my life.

  1. Date with Destiny
    Those of you who know me, know I love me some Tony Robbins. I attended Date with Destiny a few years ago with my wife, Sarah. It was an incredible 6 days of full immersion into our deepest fears, greatest desires, and helping us dig really deep into our ultimate purpose and passions in life. Sarah and I left that conference completely inspired and totally aligned with our goals and the life that we wanted to build together. In short, it was life changing. It gave us the tools and the clarity to continue to build our companies and live a life by design. No limits. No regrets. Only growth and passion and purpose. https://www.tonyrobbins.com/events/date-with-destiny/
  2. Coaching Skills Camp
    Coaching Skills Camp is taught by the incomparable Dianna Kokoszka, the CEO of KW MAPS Coaching. This 3 day conference gives you the tools (and most importantly, the questions) to achieve 100% productivity from anyone in your life. I have attended Coaching Skills Camp several times and always take away some new piece of information, a great question to ask my team, or a model that can be used to get my team hitting their results consistently. It’s a high energy, intense few days full of both coaching theory and practical leadership advice. This class is a must for leaders to better understand yourself, your leadership style, and how to coach and lead your team. http://mapscoaching.kw.com/coaching-skills-camp
  3. Spend 30 minutes – 1 hour with Billionaires
    Okay, so this isn’t an event that your can register for online after swiping your AmEx. You’ll have to pay for this one with some good ole’fashioned networking and persistence. Believe it or not, Vermont has some pretty incredible high net worth individuals and I’ve had the privilege of sitting down with several of them over the years. Talk about some eye opening conversations. The opportunity to talk to great business leaders and brilliant minds who have seen just about everything, all the highs and lows, of building huge businesses is priceless. The key is to go into those meetings with well thought out questions and be prepared to have your thinking challenged and your mind expanded. At one of these meetings, I asked a recently retired CEO what kept him going and pushing through the multiple bankruptcies, the stress of taking his company public, and the everyday challenges of being a business owner. I loved his response, “I was having fun.” What a great perspective. How simple and profound. If you love what you do and are still having fun doing it, you can get through anything.

    Now, how do you go about connecting with these individuals? Tim Ferriss offered some great tips in The 4 Hour Work-Week or click here for a quick blog on the concept. So who are you going to connect with? Don’t forget to ask one of my favorite questions of the people you respect and admire – “Who do you know that I should know?” That should get you started. 

  4. Business Mastery
    My love for Tony doesn’t end. This is another TR conference, but very different from Date with Destiny. Business Mastery helped me take a deep dive into my businesses and really helped me focus on four core businesses that would strategically and vertically integrate. It helped me develop a road map. And it wouldn’t be a Tony Robbins conference without a whole lot of psychology. We discussed the critical component of creating an empire – emotional fitness – and how to take massive action in order to get massive results. If you want to create a big life through a big business, this one is for you. https://www.tonyrobbins.com/events/business-mastery/las-vegas-08-17-2016/

  5. Advanced Transcendental Meditation Retreat
    I have been practicing transcendental meditation for about three years and going to a retreat helped take my practice to another level. These retreats couldn’t be more different than the high octane Tony Robbins conferences, but just as impactful. The last retreat I went on was 3 days of meditation, yoga, nature walks, ayurvedic meals, stretches of silence, and rounding (asanas followed by meditation, over and over throughout the day). This retreat taught me to settle my mind, to be comfortable with silence and with the inner self. There is a whole lot going on in the external world every day and it just keeps moving faster and faster. An Advanced TM Retreat gives clarity and tools I can use in my every day life to stay calm, centered, and aligned with myself and my goals in this crazy world we live in. To find out more about Advanced TM Retreats, go to www.tm.org and find a TM teacher in your area.

I’m always looking for great training events. What training events/conferences have had the biggest impact on your life?

My 10 Favorite Questions for Coaching & Leadership

adam and asherWhy? What is that? Why? Can I have that? Why? Why? Why? My son, Asher, is almost 2.5 years old and the questions are endless. He’s adorable. And persistent! Takes after his father.

Questions hold a lot of power, both in what you are asking, how you are asking, and how you are answering them. Are you asking powerful enough questions? Are the questions you are asking yourself or others moving your business forward or helping your team self-discover and accomplish their goals? They should be.

My 10 Favorite Questions: 

  1. Who do you need to be in order to live the life you desire? 
    Don’t just ask this question once, ask it over and over again. Ask yourself and ask your team. If you envision your life as an entrepreneur, running a coaching business from a beach in Florida, then are you being that person? Does your calendar reflect your priorities and goals? If you want to be an exceptional parent, are you being one? If not, what can you do differently? Are you actively making choices that take you closer to your goal each day?
  2. What questions are people asking you? 
    I love this one! Think about all the questions people come to you with. Hallie, my Chief of Staff, has said this for years. Not many people ask her out for drinks or to go to go to parties, but former bosses, colleagues, family members, and friends all reach out to her for career advice, resume reviews, business questions, book recommendations, etc. Now what do you think she is known for? What are you known for? Just think about the questions people are asking you and you’ll know. Don’t like the answer? Take a good hard look at your activities and start making some changes.
  3. What am I missing?
    This is one I ask myself every day. Whether it’s trying to tackle a problem from another angle or when there is a leadership challenge in my organization. It gets me to stop and reconsider what other solutions there might be. Ask your team this one too – What are you missing? And when they answer, continue to dig deeper. Okay, what else are you missing? And then get into an action plan from there.
  4. Who can do this? 
    I love leverage and ideas. So, in order to make all my ideas happen, I need other people to do them. My first thought when a new idea crosses my mind or someone on my team wants to implement a new initiative is, “Great! Who can do this?” If you are not yet in position where you can completely delegate, then ask, “Who can help with this?” This gets you into the habit of delegating, going to an expert, and ultimately implementing a project or idea faster.
  5. What action are you going to take? When are you going to do it by?
    Ideas and self-discovery only take you so far. You must get into action. These are great questions to ask a team member to get them out of their head and into an action plan. The key is to set a deadline and then follow up. It is a waste of everyone’s time and a slap in the face to someone to ask them to track their results and then never follow-up.
  6. Do you mind if I explore and coach a little bit here?
    This is such a critical question, especially when you are in a new coaching or employer-employee relationship. As a self-proclaimed master, genius, world-class problem solver, my modus-operendi is to just jump in and start dispensing advice and solutions. Not always the best way to go. You must get their buy-in first. In this case, you do want to ask for permission first (so you won’t need forgiveness later), and yes, you must wait for the answer.
  7. Who do you know that I should know? 
    Killer question. My mission is to surround myself with the best people on the planet, so I ask this question of those people I respect and admire. You would be surprised how many times I hear, “Oh, yeah, you should meet ________; I don’t know why I haven’t introduced you before.” Bottom line, just ask. You’ll meet a lot of amazing people this way and be able to build your bench of talent that much quicker.
  8. What if you changed your story? 
    Everyone has a story about themselves. Some are inspiring. And some are crippling. For example (and you may have heard a version of this story before), two brothers grew up with an alcoholic father. One struggled with addiction his whole life, in and out of rehab, divorced twice, in debt, and eventually landed in jail. The other brother, married, had 3 beautiful kids, and ran a successful restaurant franchise. When asked how they ended up where they were, they both answered, “My father.” Now, what story do you think they each told themselves? Pretty powerful. What story are you telling yourself? And what would happened if you changed it? Forgot the labels you have given yourself or others have bestowed upon. You have the power to write whatever story you want. So what’s it going to be?
  9. Is this a skills issue or a commitment issue?
    When someone is not meeting their goals, I like to pull out this question. It usually comes down to two issues – skills or commitment. And 99% of the time, it’s not skills. The person usually has the skills, is working on them, or knows where to learn them. It’s usually an issue of commitment. Not being committed enough to their goal, which usually translates to not wanting to do the work required to reach that goal. A skills issue I can coach through; a commitment issue, not so much. Someone either wants it or they don’t. I can’t want someone’s success more then they do. This question is a good way to get that person to self-discover that either the goal needs readjustment to something they are more motivated to achieve or that another position might be a better fit.
  10. What else can we do? 
    There is always a way. If something is not working, if we not meeting our company goals – what else can we do? It is so critical to come from a solutions-based and abundance mindset. This goes for your relationships as well. If you’re planning a client event, ask yourself, what else can you do to wow them. Or what else can you do to show your partner how much you appreciate them. There is always a solution or a way to improve the status quo. Ask yourself, ask your team, and you will find the answer you were looking for.

Bonus Question: What’s the ONE thing you can do such that by doing it everything else would be easier or unnecessary? That question is just pure genius. If you haven’t read The ONE Thing – go read it. Now.

“Quality questions create a quality life. Successful people ask better questions, and as a result, they get better answers.” – Tony Robbins

We’re always one question away from a breakthrough. What is that question for you or for someone you are coaching/leading?