CEO, COO, CFO, President. We all hear about these important roles in the corporate world, filled by people we know are at the helm of bringing a company or organization forward. But did you know that there is an unsung hero that stands behind these other roles? Today, we look into the importance of the Chief of Staff with a former Chief of Staff herself turned Executive Leadership Coach, Author, and Founder of Next Level Coaching, Emily Sander. She joins Rosie Zilinskas to shed light on the role a Chief of Staff plays and why it is just as important as the other executive positions. Likening it to an air traffic controller of the office, Emily captures the crucial responsibility of a Chief of Staff to keep everything in a company coordinated, on time, and safe. She then breaks down the characteristics needed to do the role well, especially in a world that is getting more competitive and unpredictable by the day. For more insights on being a Chief of Staff and navigating the executive space as a woman looking for that next career move, tune in to this conversation with Emily!
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Have you ever been curious about the role of the chief of staff in the corporate world? You are in luck because I have Emily Sander with me. She is a former Chief of Staff who is now an Executive Leadership Coach and author. She’s going to be able to shed some light on why this role is the unsung hero of the corporate world. We are going to be diving into why this role is like being an air traffic controller of the office. They are keeping all the plates spinning and the flights on schedule. If you are curious about the importance of the chief of staff role, please stay tuned because Emily is going to shed some light on all things chief of staff.
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Emily, how are you doing?
I’m doing well. How are you?
Great. Thank you so much for being here on the show. I’m excited to have this conversation with you. This is the first time that I am having a conversation about what a chief of staff does and why it’s important. That’s a great segue for us to start the conversation. Can you tell me from your perspective, having been a chief of staff, what is a chief of staff? The second part of the question is, why is a chief of staff an important role in an organization?
A chief of staff is an executive leader in the business world. It’s one of the most dynamic roles. There’s no one way to be a chief of staff. The analogy I like to use is an air traffic controller. You know those big towers at the airports where you have a person talking to, all the planes, all the pilots, all the ground crew, and making sure that everything is coordinated, on time, and safe. That’s what a chief of staff does for a business. They’re typically the right-hand partner to a CEO and they will be in coordination with him or her every day. Also, they may take care of the executive leadership team, so your C-Suite team and your VPs.
If you ask yourself in your business, could you use more time? Could you use more collaborative communication between your team members? Do you sometimes make decisions, and then no implementation or follow-up happens? If all of those questions are coming up for you by drift, then you can use a chief of staff. Certainly, I’ve seen small businesses use them as well. When they’re scaling and when they have to build those internal processes or even expand their leader’s viewpoint of how they add value because how you add value in a startup changes when you get to be 50 people, 100 people, or growing even further, a chief of staff who’s versed in a coach approach or change management can help facilitate those things.
I love your analogy of the air traffic controller because that brings a good visual of all the planes flying all over in the sky and you’re the one that’s directing traffic. Also, I’d like that you said that you can bring a different perspective to the leader that you’re supporting. Correct me if I’m wrong, but you as a chief of staff probably have more of the ear of the people at the desks versus the CEO. Would that be something that you agree with?
There are a couple of things there. A chief of staff is in charge of the information flow throughout the company. If you think about it, if you’re on the executive team and you’ve made all these decisions, you have a dozen meetings to make this decision, and then you lightning bolt that down to your organization, if that message isn’t conveyed accurately or as intended, you could have a whole bunch of issues there, so that’s one direction. Also, “bottom-up” is important too. If you have a customer service team who’s taking inbounds from customers all day long and that feedback or the themes of what they’re hearing isn’t getting up the organization, that’s a problem too.
The last direction would be horizontal or diagonal, which is if you have silos in your business. I don’t know what they do over there, but I keep my head down and do my one thing, then no one’s performing at their best. A chief of staff can help with all of that. Yes, to your first point, which was when you have a CEO, the chief of staff is often the only person to say no to them or challenge them. Also, the only person to say, “Good job. You did a good job. In that last meeting, you did well.” Almost no one says that to the CEO. Yes, you certainly have the ear and are the confidant of your principal or your CEO.
“When you have a CEO, the Chief of Staff is often the only person to say ‘no’ to them or challenge them and the only person to say ‘good job.’” – Emily Sander Click To Tweet
I’m coming to this conversation from the perspective of the women in the corporate world who are trying to advance in their corporate careers. Has anybody come to you and said, “Emily, how did you get to where you are?” Give me a little bit of insight. What are some of the characteristics or attributes that you need to be a chief of staff?
To be a chief of staff, you certainly need to be adaptable. You are moving from a strategic world to a tactical world. You’re going back and forth all day long, so you have to move back and forth seamlessly. Unexpected things happen, we all know this. In the market, company, reorgs, and mergers, you have to be adaptable. While being adaptable, you still have to be focused. “If these are our top three priorities, let me adapt to what’s happening, but we need to stay focused on those top three priorities.”
It is having that mix or that dynamic combination of skillsets. A big one too is listening. I’ve heard this like, “It’s a soft skill. You listened. That’s patience.” No. This is a critical skill. It will game-change how you lead. One of the things the chief of staff has to do is to listen well to entry-level folks and to mid-level managers. What are they concerned about? What do they care about? To your C-Suite team members, they might look invincible, but they have their insecurities as well. Listen for those things and how you can help and enable.
A question I always ask is, “How can I make someone’s life better? How can I serve my team?” When you have that lens, “I see a dozen things I could be doing right now.” All of those attributes are key. The last thing I’d mention is you have to be analytical and also intuitive. You have to be like Mr. Spock and Captain Kirk, and you have to be able to flex those different muscles.
When you were saying that you go all the way from people that are at the desk all the way to the C-Suite and everything between, people are coming to you not only to say, “We need to get X, Y, Z done. Bring it to the CEO’s attention. Also, things are not working well in this particular department. How can we improve that?” Is everybody coming to you and that’s where you are doing the air traffic controlling?
People are coming to you, and then you’re also putting yourself in a position for people to come to you, so walkabouts are big. Before COVID, it was, “Let me walk around the office.” I planted myself in places where people would be like, “Hi, Emily.” I’m like, “What’s going on? What’s new for you?” In the lunchroom at the water cooler, just hang out there and people will find you, talk to you, and tell you about their day.
It’s funny. People act differently around the CEO or a leader. They get, “You’re the president of the company.” They will have very different conversations with me as a chief of staff versus the CEO. I’ve seen VPs clam up, “Emily, this is a problem. We have to do something. It’s so unfair.” I’m like, “Here’s how we’re going to tee up this conversation with the CEO. I’m going to do it like this, hand it off to you, and you’re going to present this case.” We get into the conversation with the CEO and I go, “Anna has something important to share. Go ahead, Anna.” “No, everything’s fine.” I facepalm. It is being able to say, “I want to be objective about this, but also here’s some information that you probably need to know about that’s not getting to you and being able to be the messenger for that.”
I like that. Being the messenger is going to be so operative for you as the conduit to that senior leader or CEO. I found myself that when I was in management, I had a team of 10 to 12 people and I would implement some processes. Everybody would be like, “That’s great. I love it.” I then hear through the grapevine or through the grumblings that they don’t like it. It always puzzled me. Why didn’t they say to me, “I don’t like it?” I’m very approachable. Let’s talk about it.
Maybe it’s the hierarchy, maybe it’s the title. I always was good when we were in an outing or somebody had a family member. They’re like, “This is Rosie, my boss.” I’m like, “I’m not the boss, I’m your coworker because I have a different title, but we’re in the same team. We’re in the trenches together.” I always try to have that open-door policy. Even with that attitude, people still don’t tell you what they’re thinking, but they tell other people and they finally get to you.
I went through that. It was right around when I became a director. At that level, people perk up and pay attention to you in a different way. It was baffling. It was like, “Wait. I’m just me, but you’re acting weird.” It is about, “My title precedes me.” When you have a title that goes first and you do sometimes need to make a conscious effort to put people at their ease or do things like you were doing like, “It’s just me,” I would often share, “I need your help. Can you help me? I need your input. I need your feedback on this.” That would usually open the door. Also, a good one is leading with, “Here’s what I messed up on last week. Everyone, heads up on that, don’t do that.” That’s like, “I’m a human too,” and it opens the door.
I love that because you’re immediately diffusing the whole thing of, “I’m the director.” “No, I’m a human being and I have feelings and emotions. I make mistakes too.” That’s huge. You talked about the conversation that you teed up for the CEO, and then the manager didn’t say anything. What are some of the strategies that you think are critical for women who are trying to have a conversation with their manager about their performance, maybe they’re wanting some feedback, or maybe the manager is doing something that they don’t like? What are some strategies that you recommend to start having a hard conversation or a difficult conversation?
The first thing I would say is to tie it to something that they care about. If you imagine someone coming up to you and you perceive it as like, “You’re just complaining,” how are you going to respond to that conversation? Whereas someone says, “I know you’re big on relationships, learning, growing, and making a positive environment for your team. I have some information that could help with that.” I’m like, “Okay.” You’ve already got my attention, and then you can go into the conversation that way. What’s important to them, often with CEOs, is revenue, “I have an idea about how we can make some more revenue or cut on expenses.” Right away, you’ve got their attention and then you can present what you’re about to say in that light.
How do people start that conversation with a manager when they’re trying to advance in their career and they don’t know how to say, “Can we talk about my career development? How am I doing?” A lot of times, managers don’t have the time. Unless it’s your semi-annual and annual reviews, you don’t get feedback, but people are apprehensive to ask that question.
What I would say there is you need to be proactive and not just come up with an open-ended question and have no idea. It’s like, “How am I doing? What does my career look like? When do I get a raise?” Those are not good leading questions. It might be, “Why don’t I carve out some time to think about what I want and what I think that my experience demonstrates and say, ‘Here’s the direction I’m thinking of going. What do you think about that?” “Absolutely. You would be amazing at that. That’s an admirable path to go on, but I actually see you more over here. I see you in people management. I’m happy to support you on this path, but we’ve been talking about you in this direction.’”
It might be leading with a, “I want to get to be in the C-Suite. As director, that’s a step that I’m going to have to progress to. I’m thinking about how I can get myself there and me taking on a project like this or me maybe getting this certification outside of work would be helpful. Are there any other things that you can suggest for me to get there?” You’re changing the tone of the question to a presumptive close and the person is adding valuable feedback to you.
Those are great suggestions because when you’re on trial and they’re like leading the witness, you want to lead them a little bit so that you end up where you want to go, not where they want you to go. Like you said, they might say, “I was thinking you could be great at marketing,” but maybe you were thinking product management. Coming into the conversation with a formulated plan for yourself first and taking the time to think about it is so smart and strategic versus going in there and saying, “Can you give me some feedback on my performance?” Every time people are put on the spot, they can’t think of something.
You’re putting them on the spot and you’re putting a lot of pressure on them. Think about it like this. Let’s say you’re about to write a book and you have a blank page or a blank Word document, and the cursor’s blinking at you. You’re like, “I have to create this thing.” That’s like when someone asks you, “How am I doing?” out of the blue. Whereas if you have a draft, an outline, or some ideas to work with, “I can play off this. I can brainstorm that. I don’t want to go that direction, but that makes me think of X, Y, and Z,” that’s a much better place to start from.
A little tangent from there, I’ve been coaching people to use ChatGPT as a starting point for whatever it is that they’re trying to do. It’s always easier to start from a baseline and idea foundation, and then change it, tweak it, and edit it to meet your needs versus that blank piece of paper that you’re like, “I don’t know what to do. I don’t know where to start.” That’s a little bit of ChatGPT plug. Let’s talk a little bit about when someone is trying to make a career change. What are some of the biggest mistakes that you think people generally make when they’re looking to do that career change?
I could come at that from a lot of angles. The thing that’s coming to mind is don’t act entitled. When people used to come to me and say, “You need to give me a raise,” I’m like, “Hold on. Let’s talk about why you think that you deserve a raise.” I would get a lot of people doing the ultimatum like, “I need a raise or I’m going to walk.” I would often say, “Here’s the door.” That’s how not to do it. I would say be intelligent about the type of work you do and the type of projects you’re involved with. There’s a little bit of, “Is this project visible? Will this give me exposure?”
I was even in a position where if I took this one project on, I would be in this one meeting that had the VPs and the executives in it. I didn’t actively participate in that particular instance. I was listening and I could pick up on what. Even things like that, be a little bit strategic about what you take on. If you do feel like, “I’ve demonstrated that I can do this job,” then make your case for it and make it as objective and demonstrable as you can.
Pretty much, “I’m already doing 80% of this job. If you give me the title, then I’m able to do the rest of the 20% by extension.” You almost do that presumptive close. Don’t be arrogant. Don’t act entitled. “I’m doing this job. Here’s what I’ve demonstrated.” Have your information ready, and then, “What would it take for me to move into a position like this?”
I will add one thing that I always like to tell people. When you are able to show somebody how you are helping them achieve their goals, that’s the cherry on top where you’re like, “I’ve done all this and I’ve done these accomplishments, but the bottom line is that I’ve helped move the needle on our collective goals for the company.” When the CEO pays attention where you’re like, “I can save you money,” when you tell somebody, “I can help you meet your goals,” they’re like, “This person can help me meet my goals. That’s great.”
That’s also a good conversation to have at a job interview when you’re interviewing and saying, “This is how I can help you meet your goals.” People pay attention when it comes to that. I know that you have a couple of books that you’ve written and you talk about the Art of the Swizzle. Tell me a little bit about the Swizzle and how you use it as a resource.
Swizzle is a framework for being creatively resourceful. I’ll tell you how it came about. I was running around one day. I was very busy and I was talking to my team and we had to put a presentation together that afternoon. I knew we had three previous PowerPoint decks that we had content that we could pull from each one. I said, “We have that presentation. Swizzle the three decks together and let’s do it.” By context, they knew what I meant. I was saying to take the best and most relevant slides from each of the three previous decks, reformat it, reorder it, and make it the new one.
Another example that I love to share is I was listening to a podcast and they were interviewing Floyd Mayweather. Floyd Mayweather is a champion boxer. I don’t know anything about boxing, but he was elite in his field, so they had this person on. They were saying, “Floyd, what makes you elite? What makes you the champion? Is it your diet? Is it your footwork? Is it your training or the speed of your hands?” He finally said, “No. It’s my adaptability. I can adapt to any opponent any round and any punch better than anyone else. That’s what makes me a champion.”
I was listening to that and there were light bulbs. I’m not a boxer, but I can absolutely apply that to my world in business. Am I adapting to the market? Am I adapting to this person’s communication style? Am I adapting to what this audience needs in this meeting versus the one I just had? Am I adaptable? I swizzled that concept from the sports world into the business world.
I love that analogy on boxing and adaptability. It’s such a key component. Pretty much these days, we are bombarded with so many different tasks and so many different objectives and KPIs. Truly being adaptable is one of the best ways to get ahead. If you’re not adaptable and you’re scared of change, which the only thing that’s constant is change in this world, then you can get far behind very quickly if you’re not adaptable and you’re not willing to go with the flow. I like that. You probably have seen your share of failures either for yourself, for CEOs, or staff. How can people figure out how to “never fail again?”
That touches on another framework that I have, which is called the failure loop. In my book, Hacking Executive Leadership, there’s a graph, but I’ll explain it to your audience. It’s a chain of individual loops that are connected and go up to the right. The overall chain goes up to the right and that’s the direction of progress. That’s what you want to be doing. However, there’s a point on each individual loop where you’re going back down and to the left. That’s what most people would consider a failure event. “I went to that board meeting and I fell on my face. I decided to start that business and it’s not going so well. Now I have to admit to myself and other people that this is not going the way I intended.”
In that moment, if you stop and say, “I’m going to break myself and rake myself across the coals. How could I be so stupid?” If you stop, then you stay in that part of the loop. If you say, “I know where I am in the process and I’m going to take the learning and lesson and propel myself up to the next loop,” you’ve made progress. If you think about it, if you do this over and over again in your career or your life, you will be a successful person by definition. One quote that I love to go along with this framework is, “I’m successful because I fail more times than you even try. I fail more times than you’re willing to try. That’s why I’m successful.” That’s a framework for thinking about failure in a new way.
“I'm successful because I fail more times than you even try.” – Emily Sander Click To Tweet
I got a visual when my kids were little, we used to play chutes and ladders. You go up the chutes, and then all of a sudden you’re way back down again and you have to fight your way back up. I love that analogy of when you fall flat on your face or whatever and you stop and you realize where you are, and then get up, dust yourself off, and then continue up the ladder, then there is no choice but to succeed.
I say it like that. It’s not easy. It’s a gut punch. You got embarrassed. Sometimes it’s a matter of time, so know the process. If that was a big blow, take the time to process through that, and then know, “Now, it is time to move forward.” I wanted to throw that out there. You’re like, “Emily, you make it sound so easy.” Believe me, I’ve been there. Believe me, I know it’s tough. The cool thing is by hearing this or by knowing about this framework, you are closer to making progress easier.
I interviewed a confidence coach quite a while back and she said that we need to take time to sit in the suck. When you do have a failure, take whatever half day, full day, or 24 hours to experience those emotions because we all experience failure. Whether they’re small failures or large failures, failing is part of life. I think where people sometimes go wrong is when they fail their pair life and then they don’t want to try again. When you are successful is that trying again, not necessarily that you met your goals, but that you’re adaptable to trying again and continue to move on the course. Again, anybody who has a goal that continues this framework or this process is eventually going to meet that goal. It’s just a matter of continuing to move forward.
Something important that you said is that it’s painful to look back at that event and say, “How was I responsible? What did I contribute to that?” That’s a tough question, but that’s where the gems are. That’s where you get the pieces. Now, I’ve faced up to that. I’m not going to linger there and ruminate over and over, but I’ve done the work and now I can take that and apply that going forward. That’s what propels you up.
Shifting a little bit about your own personal story, how did you get to be a chief of staff? I know that you’re creating a coaching program about chief of staff or a project of that sort. Tell me a little bit about how you got to be a chief of staff and what are some of the key learnings that you’ve gained from that.
It’s the classic combination of, “I’m smart, I’m hardworking, and I had a few lucky breaks in my career.” I had some great mentors early on who opened some doors for me that they didn’t have to. At that stage of my career, I was a relative nobody. They saw something in me that I didn’t see myself. They opened a door and I will be forever grateful for those people. The other thing I would say is I am a planner, I’m organized, and I have like a very specific career path. None of that has happened. Being very open to, “I think it’s A or B. It’s option blue, triangle, and sea monster.” Something in life or something in your career will pop up that you can’t even conceive of right now. You can’t even think of it. Some doors are going to open or some opportunities are going to come together that’s perfect for you that you never thought of.
Be open to that. That’s something I’ve learned. “I’m getting anxious or frustrated because I can’t see this one thing happening.” That might be true, but 100 other things could be coming about, and leave yourself open for that. Be smart. Be hardworking. Also, open some doors for some other people because that’s giving you some good karma and putting some stuff out in the universe. Be open to, “Even if I don’t see an option now, that doesn’t mean there isn’t one for me.”
When you say you got lucky breaks, obviously that’s a combination of people advocating for you and then having opportunities, almost being at the right place at the right time. However, by you being a planner, being organized, and being a hard worker, all of those are attributes that someone is going to use to continue to advance in their corporate career. I don’t want to discount the fact that your hard work was a big contributor to that, but at the same time, having those advocates are stepping stone to making things happen in your career.
To your point, it’s funny, the harder I worked, the luckier I got. There is a correlation between those two for sure. Certainly, I give amazing credit to some mentors who have been instrumental in my life. It’s a combination of those things for sure. Be prepared. Be open to opportunities. I think Oprah said it, if preparation and opportunities meet, that’s when you walk through new doors.
I was coaching somebody and they’re starting their job search. I was like, “The biggest thing at the end is consistency and persistence.” It’s a long game. A job search is always a long game. It’s not a once-and-done, you can sit down for an hour and it’s done. You have to work at it. You have to be consistent and have that persistence. Eventually, something will happen or something will shift. I also like the fact that you said you had this picture about your career and it wasn’t at all what it ended up being. I never imagined myself as an entrepreneur, high-performance coach, speaker, or podcaster. Here I am, entrepreneur, high-performance coach, speaker, and podcaster. You’re absolutely right.
The other thing is karma. I wholeheartedly believe that we need to help those coming up behind us because myself included and you, we had mentors, we had those people that saw something in us and supported us and became our advocates. When you are not in the room, they’ll still say, “Emily’s perfect for this role, let’s give her the opportunity.” I do feel that we as women need to continue to support those women who are coming up behind us and also have conversations with them as well of, “You can do this. Apply for this position. Think about it. Go have a conversation with your manager.” We collectively need to encourage those younger women who are coming into the workforce to guide them, show them, and be aware that there are opportunities out there.
I think it was Oprah again who said, there are two types of female leaders. The type that gets to the top and slams the door shut so no one else can come in and the type that wedges their foot in the door and tries to pull as many people through as they can. Which one are you? Which one do you want to be?
To your point, the competitive edge, it’s always good to be competitive because it gives you a little bit of oomph, but not to the detriment of your peers. Collaboration is always going to be much more effective and productive than individual productivity and not wanting to share either in the responsibility or the success once the team gets to their goals.
One other question that I wanted to ask you. As a chief of staff and as a director, you always had to make decisions. How did you get to become a confident decision-maker? Whether it was a decision that you had to make on your own or for the CEO or some of the other executives that you had to make?
There are many components. The first one I would say is I learned to look back and say, “Did you make the best decision you could with all the information you had at the time?” Hindsight, 2020 is great. I was like, “I should have done that. That was clearly the answer right there.” Did I make the best decision with all the information I had at the time? If the answer’s yes, there’s nothing more I could have done. If the answer’s no, even at that time, in my heart of hearts, I knew I was trying to force that thing. Then it’s thrown in the failure loop and says, “What can I learn? What can I glean to apply next time?”
I would also say, “I have gotten much better at separating a decision from an outcome.” A decision and an outcome are two very separate entities, yet a lot of people fuse them together. “That didn’t go the way I wanted, so clearly, that was a bad decision. I made a bad decision there.” That’s not necessarily true. You could have made the best decision you could at the time and it happened to go another direction for a myriad of other external factors. I am reflective and I try to be self-aware, I say, “Let me run through my responsibility and ownership in that. Did I do the best I could?” If the answer is yes, the answer is yes. It’s like, “That sucked. It didn’t turn out good, but that’s what it is.”
I would also say be intentional. Know what you want in a certain situation. There’s another framework I’ll run through quickly called Three Circles. It’s circle 1 plus circle 2 equals circle 3. Circle one is an external event that happens. An email comes in or something happens at a meeting, and then you acknowledge that and you jump to circle three quick and you say, “What do I want to have happen here?” Circle three is my desired outcome, which is an important step. Knowing what you actually want to happen keeps you from making emotional knee-jerk reactions. You then are able to reverse engineer and step back and say, “If I want that outcome in circle two, what do I need to do? What do I need to say? What do I need to not do and not say to give myself the highest probability and get to circle three?”
With something like that, you can make decisions on the fly where you’re leading a team meeting and everything’s going great, and then, Joe over here starts to rumble and grumble and starts to yell and get irate. That’s a situation. That’s circle one. “What do I want to have happen here? Maybe acknowledge something that Joe has said and get him to calm down and get the meeting back on track.” That circle three. What do I have to do in circle two? Maybe say, “Joe, I hear you’re upset and I want to get to the budget allocation for departments as well. That’s actually on the agenda for the back half of the meeting. Some of the folks here don’t have the context for what you’re talking about. I want to make sure they do. Let’s go to the agenda here and let’s get back on track.” Something like that.
That can be how you can make decisions. The Three Circles framework also works proactively. Let’s say you’re going into a meeting and you’re saying, “This is our quarterly planning meeting. What do I want to happen by the end? I want people to feel informed, comfortable, and confident going to their teams and giving the merger update. In circle two, I need to provide an update from our latest round of conversations and then I need to listen. I need to ask a question and then hear how people are doing.” That’s what I’m going to do in circle two. Anyway, that was a long answer to your question, but those are some of the decision-making tips.
I appreciate the explanation of the three circles, and I can clearly see how you can apply that to a job search. If you are trying to become a director, and you’re right now a manager, what is it that you want to get to? You already have that circle three. What do you need to happen in circle one and circle two to get to circle three? That’s where you start having conversations. You start analyzing your skills. You start figuring out if you need additional training or certifications or whatever to be able to qualify for that circle three.
I love the reverse engineering concept because if you don’t know where you’re going, you don’t know what tools you need to get there. I think that’s brilliant. Was it a conscious decision for you to become a coach? I know you’re a coach now. What kind of coaching do you do and how did you get to writing your books?
I’m an Executive Leadership Coach. Now, I work with two main groups of people. The first is the chief of staff and their principal. I also work with early executives in a career transition. If you got to a VP role, if you got to a new role and you’re like, “I did it. Yes. What do I do?” I work with people at that stage. It’s funny. I was a coach before I knew what coaching was. I was doing coaching. That’s what I did and who I was. Once I realized that and put those two things together, “I do these things anyway. That’s a thing you can do as a profession. Eureka, I’ll go in that direction.”
I do remember I was in between jobs. I had my last day and I was waiting for the first day of the next one to start. I was like, “What’s my favorite part about all these jobs I’ve had across these companies?” I made a list. The recurring theme that was clear as day was the coaching aspect, the one-on-one relationships or collaborations where, “I helped Jennifer be more confident speaking up at team meetings. I coached Christian to say, you can take on this role. After I leave, I’m going to advocate that you take on this role and you need to step into it.”
Those types of things were front and center. I became a coach. I got certified and got trained and everything. I love it. When you can wake up each morning and say, “I’m doing good work. I’m making a difference,” and you still get that dopamine rush when you help someone else succeed, then it’s a good spot to be in.
How did you get to writing your two books?
The first book was during COVID. I had a book way back of my mind. I was like, “Maybe one day.” It was a one-day thing. Writing books was for other people. I don’t write books. That’s for fancy authors and stuff. COVID happened and lockdown happened and I was going a little bit crazy in lockdown. I need something to channel my energy into. I was at home and you couldn’t go outside of course. I then got this email and it said, “Have you ever wanted to write a book but don’t know how?”
I don’t know what I sent out into the universe to get this, but that was the perfect timing and the perfect message and I replied to it before I could think about it by the way. I remember, “Emily, reply to this.” Don’t think. Just reply, say yes, and then go for it. I did. That was from someone who was a public speaker and their industry got turned upside down with COVID, so he was reaching out to people to help publish their books. That’s how the first one came about.
It’s a collection of frameworks like we’ve been going through here that I’ve picked up over my experience and over my coaching practice that has helped people. You can apply these things to many different scenarios, but I think if you have the building blocks and tools, so not necessarily, “In this type of situation, here’s what you say.” It’s more of the frameworks that you can universally apply. Those are gold. If you have a whole bunch of those in your tool belt that you can pull out when you need to, then you’re armed for success.
The second one, which is An Insider’s Perspective on the Chief of Staff book, I wrote that in early 2023. It came out in May of 2023. That was a labor of love. I was coaching a whole bunch of Chiefs of Staff and a lot of the same questions and themes and different pieces were coming up. I said, “I need to get this in a book.” I wrote a fairly quick book. It was at Christmas, so in December I decided to do it, and then I had the manuscript done by March. The editing and the book cover and the art and all that stuff took a little bit longer, but I was in go mode. I stayed laser-focused and got that out. It’s been very well received by the Chief of Staff Community and also by people wanting to learn about that role.
Congratulations on your success on your two books on becoming an executive coach. That’s amazing when someone can use their skills. Your labor of love to put it on to the universe to help people, because that’s ultimately what my goal is for our audience. To be in a job where they feel fulfilled because if you are sitting tuning in to this and you’re in a job where you’re not engaged and you are bored and your days are long and you don’t feel that fulfillment, you need to do something, you need to take action, you have to have a conversation with somebody so that you can get out of that rut.
A lot of times the whole quiet quitting, it’s a term that I don’t think people are using as much, but if you can reengage that love of what you do, that’s going to be your best case scenario to continue to dance. If you leave it as is and you’re like, “I need to clock in, clock out, and get home.” Eight hours a day of getting by or dealing with, it’s such a chore and you can take action to change that. I love that you are fulfilled and that you’re helping people to be fulfilled in their own careers.
If I could jump in with one thing. When I talk to people about this, I get a couple of different reactions. Some people are like, “I can’t quit my job because it would hurt my family. I’m the breadwinner. It would hurt my family.” There is a timing element. I had clients during COVID where this is probably not the right time to start that business, so stay in the job you have and put food on the table for your family, but then keep working behind the scenes on putting the pieces together to start that business when things open back up. There is a reality of the situation of being pragmatic.
Also, if you are going to a job and you feel hollow inside, you’re going through the motions, and you’re punching in and punching out, how do you think that you’re showing up for the people around you? Are you at your best? Are you engaged? Are you alive? Are you giving them what they need? Probably not. When people say, “I can’t let people down,” then don’t. Figure out where you want to go. I waffle off, “Follow your dreams.”
With that saying, I agree with the sentiment. Put your money where your mouth is and create a deliberate plan about how you’re going to do this. Say, “What do I enjoy doing? What do I lose time doing? I’m in flow. What does my experience lend itself to?” Where those circles meet, it’s like a Venn diagram. “What does the world need?” is the third one. Where would people actually have a demand for it? Where those intersect, here are some opportunities in that sweet spot. Let me be deliberate and maybe put the Three Circles plan or something similar in place and go after that.
Is there one tip that maybe you can leave? Of course, you’ve already given us a lot, but one tip that you can leave the audience with is in that job search mode. Whether they want to continue to advance their careers or maybe they feel stuck, one tip that you can provide.
That’s hard to pick from. I might give you two. The first one is, if you knew you couldn’t fail, what would you be doing right now? If you knew you couldn’t fail, if you knew anything you did would be wildly successful, what would you be doing differently than you are right now? That’s the question or a prompt. I would say, go out and get your small win. If you’re in a job search, what are the small pieces that you can put together today or tomorrow that will help you get towards your goal? It could be, “I’m going to review ten job descriptions. I’m going to apply to three of those. I’m going to make sure I take a walk, keep myself sane, and get perspective.” What are the things that you get a small win for? When you put your small wins together, small wins add up faster than you think.
“Go out and get your small win.” – Emily Sander Click To Tweet
Thank you so much for spending this time with us. I enjoyed our conversation. It’s very evident that you are good at creating those frameworks that are very easy to understand. Maybe not easy to implement, but baby steps and a little bit of action goes a long way in the end. Thank you so much for being with us and I appreciate your time.
Thank you so much. I respect and appreciate what you’re doing. It’s been an absolute pleasure to be on your show, so thank you for having me.
Thank you.
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I have some major takeaways from my conversation with Emily. Being adaptable and open to new opportunities is crucial for success. Emily emphasized the importance of being flexible and willing to adjust to different situations in different challenges. Adapting to change and being open to those new possibilities can lead to growth and advancement in career. Again, you have to be willing to put yourself out there.
The second thing that was a major takeaway is that failure is not the end, but rather a stepping stone to success. Emily introduced the concept of a failure loop where setbacks and failures are seen as learning opportunities. I think that was a crucial learning there. Instead of doling on the failures, she said it’s important to reflect on those failures, learn from them, and use them as knowledge to propel yourself forward.
Emily gave us two great tips. The first one, she said, “This is more of a prompt to get yourself to think. Ask yourself, if you knew that you couldn’t fail, what would you be doing right now?” The prompt here is for you to think about your aspirations and your goals without the fear of failure holding you back. It also encourages you to dream big and consider what you truly want to achieve.
The second thing that she leaves us with is to focus on achieving small wins. Break down larger goals into smaller, manageable tasks that can be accomplished in the short term. By doing this, you will be able to celebrate those small wins and build upon them. This way, you can gain momentum and make progress towards your larger goals.
Before you go rushing off to your next thing or to connect with Emily, I also want to talk about your next career power move. This is for you if you are ready to be promoted, but not sure where to start. I encourage you to take three minutes to complete the Promotion Readiness Checklist. This checklist basically takes the guesswork out of the fact if you are ready to be promoted or not, or what’s holding you back in your career. Once you’re in the know, you will be unstoppable because you will have actionable things that you can work on. With that, remember to be brave, be bold, and take action. Until next time.
Emily Sander is a C-Suite Executive turned Leadership Coach. She is the founder of Next Level Coaching. As an ICF Certified Coach, she helps business professionals step into effective leadership with one-on-one coaching. She’s written two books: – “Hacking Executive Leadership” and – “An Insider’s Perspective on the Chief of Staff.
