Leaving a corporate job and taking the leap of faith to be on your own can be both scary and exciting. Anne Sugar definitely went through all those emotions when she made the decision to leave the corporate world to start her own coaching and consulting firm, advising top leaders at companies including TripAdvisor, GM, Delta, and many others. To create positive action in the coaching process, Anne employs a two-pronged approach for a successful engagement – combining a goal-based process with evidence-based coaching. She sits down with Michael Zipursky on today’s show to explain this further. She also shares her transition journey, highlighting the importance of having mentors and coaches and revealing what gave her confidence to go out and take that leap. Seeking to make a career transition? This is one show you don’t want to miss.
I’m with Anne Sugar. Anne, welcome.
Thank you, Michael. I’m excited to chat with you.
We’ve already had a great start to the conversation about books, bookshelves, and the ways that we organize our bookshelves. I enjoyed that. Let’s dive in. Anne, you’re a published author, you’re an executive coach, speaker, you run your own coaching consulting firm for about more than fifteen years now. Your clients include TripAdvisor, GM, Delta, and many others. You’re also an executive coach for the Harvard Business School and guest lecturer at prestigious universities like MIT and the University of Pennsylvania. I want to get into all of that but before we do, take us back to how you got into the world of coaching and consulting. Where did that begin for you?
I grew up working in advertising agencies. Back in the ‘80s, I worked in New York City. I worked on the launch of the Apple Computer. Yes, I’m dating myself how old I am. The American Express Corporate Card. To take a step back, I know that I have grown up working in teams and understanding, “What teams look, how do you sell, how do you sell to a client, and how do you have a high functioning team. All of those things you learn when you work in advertising.” All of that, at the end of the day, boils down to creativity and curiosity, because it’s about the idea.
As a starting point there in terms of what I’ve learned, I worked in advertising for many years and at a certain point for me, I wanted to do something different. Working 60-plus hours a week and an array of things. This gets back to when I think about teams and how I talked about creativity, the thing that made me the happiest was leading teams. I met with an executive coach. I wish I had had an executive coach when I was managing 75 people working through all of the executive suite things that I was. What it came to find out was I wanted to help people lead better. I wanted people to help them not make the mistakes that I made because God knows I made some good ones. I took the leap and it’s a long story, how I got there, but I’m certified. I have all the credentials and all the assessments. I’ve been doing that now for many years.
Quick question for you. How long were you thinking about leaving, going off on your own, and leaving the agency world before you took the leap?
It took me a while. I did a lot of fits and starts. This is an interesting story. Even when I said, “I’m going to be an executive coach. I’m doing this.” One last time, I went on an interview for a media director job here. At that time, I had a new baby. I was like, “Maybe I’ll go back into advertising. I love advertising. No, I love this.” I’m so overtired and I hit my garage door with my car. After this long day of interviews, all going down, I’m not into the whole universe thing but I was like, “No.” That was a watershed moment for me when I hit my garage door.
What do you think held you back? As we’re talking, was it 1, 2, or 5 years ago? Was it on your mind before you made the leap to clarify that?
I’m looking back, it was probably a few months. It wasn’t that long.
From the time that you thought to yourself, “Yeah, I want to go out on my own,” and you made the leap, so it was about few months from the time that you had that thought you hit your garage door going. Somebody is telling me something here. Walk us through that. When you made the decision to leave the corporate world and start doing coaching, consulting, and so forth what was the first thing that you did?
Can I raise one other point?
Why was I being wishy-washy? Come on now. I would never go back but it was hard because let’s think about it for a second. I had a lot of infrastructure underneath me. From an admin to somebody who does my PowerPoint, and those little things. There are a lot of infrastructures that are gone. I knew how to sell to clients from advertising. I knew how to market. I knew all of that but when you get to those brass tacks, it’s different in terms of marketing and business development. Those were the things that gave me pause.
The question that comes to me is when you had that pause, what did you do to overcome it? I know you hit your garage door, but you don’t have your garage door going, “Now I know how to sell my services and price my fees, and all that stuff.” What was it that made you go, “Let’s do this?” What gave you the confidence to go out and take that leap?
I do this in coaching. There are some people who say, “Rip the band-aid off.” We go for it or something. We rip the band-aid off and do it. Other people need to take small baby steps and have a specific plan. For me, personally, I rip the band-aid off type of person. I burn the boats. I thought, “If it doesn’t work, I go back into the corporate world. I can always be in advertising.” I love advertising. I still coach people in advertising.
What did you do? You made the leap, then what was the first thing that you did to get out there and start winning clients?
For me, it was a lot of baby steps. I went back and got certified. I started telling people that that’s what I did. This is the hard part, I knew it intuitively, but I didn’t think about it. To change your brand, from me being in advertising to now an executive coach is a complete brand change. I know that you have to have a lot of patience because it takes a long time to change your brand. As another aside, when people say to me, “You are published in Harvard Business Review, Forbes and Inc.” There were a lot of micro-steps for me to get to that point. When I talk to people starting out or people two years in and they’re frustrated, you have to have a lot of patience, I believe.
As you’re working through that, and I want to come back to when you first do, but when you encounter those feelings that are likely bubbling up, you’re working through stuff, maybe it’s not coming together as quickly as you’d like. You’re not seeing great results right away so you need to have patience, as you said. What have you found helpful? What’s your mindset around that? What would you advise somebody to try and embrace, to look at or think about that would help them to get through those rough spots?
I’ve learned this from my husband and from other people. “Take one step that you can control.” You can’t close. You cannot control whether you’re going to close that client, but I can control that I can email five potential clients or five people I know. That’s what I know I can do. It’s to control what I can control. I can’t control the sale.
That’s powerful. Oftentimes, taking that action, whatever it is, causes some positive result, which gives you more confidence, which then makes it easier to do more. It’s this network effect or self-fulfilling prophecy of you taking one step and it creates the next one, the next one, but so often, people are paralyzed in fear. They’re frozen because they’re not sure what to do and they don’t want to make a mistake, but what you’re saying is the importance of taking action.
Michael, you bring up such an important point in terms of making a mistake. That’s a hard part from a consultant perspective that’s different from when you’re in Corporate America. When it’s your mistake, it is completely your mistake as a consultant or, “I didn’t do this right. I wrote an email to this person.” I’ve written some bad emails to potential clients. You do or you make a mistake whatever it is. That’s an important point to bring up. Let the mistakes go. Also, having a network of people that you can talk to, moan and groan to or another executive coach, whatever that is.When taking the leap, some people rip the Band-Aid off and just do it. Other people need to take baby steps and have a specific plan. Click To Tweet
Having a community of people is definitely very important. Let’s go back, so you leave the advertising agency world, you now are a certified coach or you’re working towards that, what do you first do? You mentioned that you email some people and let them know what you’re now doing. What would you say, looking back was the first, let’s call it, big break, the first big client or that initial experience or situation where you felt like, “This is going to work. I’m feeling confident about this and about the future of my business.” Do you remember what that was for you?
I know exactly what it was and it happened because it was a referral. Referrals are so important in a consultancy landscape. Somebody that I worked with in advertising, who’s an HR said to somebody else in HR in a company, “You should meet with Anne because she can help you with this.” It was leadership development training. I went in, and I win it. When you win that first one, it gives you calm. It’s like a multiplier effect somehow. I’m not saying all the time. There are dips and ebbs and you try to smooth things out.
How would you say that your approach to marketing in your business has changed? When you look at that first phase, let’s say the first few years of getting things going and to a place where now you feel there’s some stability, and you feel that you’ve got to that next level of expertise, and authority status. Is there a type of marketing or type of outreach? For the methods or tactics, has that changed compared to now?
In the beginning, I call it guerrilla sales. It’s like combat. You’re talking to one person and now it’s much more of a flattened long term of, “I want to meet interesting people now.” That creates a business or maybe it doesn’t and I interview somebody interesting for Forbes.
Give me an example of that and make it tangible for people. What were you doing in the early days? What was maybe one thing that worked well for you in the early days to get clients?
I did a lot more reaching out to people that knew me. It’s because I changed my brand, I needed people to remember my skillset and what I did in advertising, and how that translated into being an executive coach.
Were you sending them an email and saying, “It’s been a while. I hope you’re well. Here’s what I’m doing now.” Is that the type of email or was it something different?
That sort of thing, but also, “Let’s set up a meeting and talk,” but I believe there has to be something in it for the person. I would sit there and think, “What leadership issue does this Chief People Officer have now in their company? I’m going to send them two articles along with my conversation.” Part of all of this is giving something and for me, it’s giving knowledge or connecting people. A lot of it also is connecting people, “You need to talk to this person over here. I know you’re looking to hire this person.” Even though it was more of a guerrilla one-on-one Guerilla marketing thing, it still was about what I can give to people.
How does that then compare to now? Are you doing less of that outreach or is there anything you’re doing more of now that you weren’t doing before that works well for getting clients?
I still do that now because you can never stop that as a consultant. This sounds crazy. I’m not equating myself to this but if you think about movie stars, they’re always looking for their next movie. You’ve got to stoke the fire constantly what’s different now, when I look at the landscape because there’s a tremendous amount of coaches or consultants. What do you do that makes you unique and standout? Uniqueness for me is thought leadership because if I go back to my advertising days, it’s about, “What’s my unique point of view?” That’s what clients wanted to know in advertising. It’s the same thing now.
Is the focus now to create content that is unique that is valuable for your ideal clients? Is your focus on publishing it yourself as the focus on getting into publications that your ideal clients read? What’s the main focus in terms of where you see the greatest return on your time and investment? Where are you getting the greatest overall result?
That was a fit and start thing. I first started out writing some stuff on my website. It would be crickets. I started to write a little bit on LinkedIn and I’m embarrassed when I go back and I read some of that. For me, it’s more about a platform in pubs Harvard Business Review, Forbes, and Inc. That’s where I focus and write. It’s two things. It’s about having a unique point of view on something that interests me, and also interviewing other interesting leaders that can help anybody in creating systems or whatever that is.
Do you find that interviewing leaders for your article or for the content you’re creating is also a way for you to generate clients, meaning, the people you’re interviewing are those people that would become clients? Does reaching out to them for the purpose of an interview create the start of a conversation where they could then become a client? Do you find that’s typically not the case for you?
This is my point of view, I keep it broad. When I’m interviewing somebody, it is not me selling to them. I truly look at this as thought leadership. I tried to keep it at that. For me, it’s relationship building and getting interesting content out. When you bring up the topic of writing, a lot of people will say to you, or say to me, “Write about what you do.” I’ll do some presentation skills stuff. When I write about that, I write about what is that I’m passionate about. Sometimes things that I write about are some things that interest me at the moment. I don’t have an editorial calendar. I write for that week. That might not be good either. People need to have an editorial calendar. I do not.You have to have a lot of patience because it takes a long time to change your brand. Click To Tweet
It works for you.
That’s my biggest point, Michael. What works for you? All of these things that we’re talking about.
How has your business changed over the years in terms of the services that you provide the way that you offer them? Is there anything that you look back on going, “The way that I work with my clients is much more leveraged. I used to offer something that didn’t work well?” Are there any lessons that you would maybe say to somebody, “This is a shift that I made and it helped me for the better,” in terms of how you structure your offerings?
It’s not so much about structuring my offerings, but it’s about creating repeatable content that I can leverage. I have a strategic framework map of how to work with executive coaching clients. Two, I do a lot of executive training and I do bespoke training. I have a massive library now of things that I’ve written over the years that I can use that are repeatable. It’s my content so I can use that as training. It’s important to create bespoke, but I also think, “What are the repeatable frameworks that you can use so you’re not recreating the wheel each time?”
It sounds like you’re developing a lot and have developed a lot of intellectual property over the years that you’re able to leverage for content as well as for working with your clients. You mentioned that you don’t use a content calendar. To me, it sounds a bit more organic or free-flowing in how you approach content creation, yet you do write for different publications. How do you approach writing? Oftentimes, what I’ll hear from consultants and clients is, “Michael, I’m so busy delivering on a project or multiple projects, I don’t have time to work on my marketing. I don’t have time to develop content.” Any advice for those people who might be struggling to create content or to work on their marketing and business development because they’re so busy delivering on projects?
Yes, there are times when I don’t have time to write or I don’t have time to do marketing, so you have to live in that mess. I had one of those for three weeks. I was so busy. You live in that mess over there. That’s okay. What’s not a mess? It was great with the clients. It is organic, but it’s not. I have this Moleskine notebook. Whenever I think about something, “That’s an interesting idea,” I write that down in my notebook. I have 40 pages of interesting ideas, so I can flip through there and do it. The thing with writing, marketing, or any of that is, you have to keep doing it. For example, I wrote an 800-word article. I did it in a couple of hours and it’s all done. Maybe years ago, I could not have done that. It’s about repetition. I got up at 7:00 AM and banged it out and it took an hour. We all can find an hour because we’re scrolling on TikTok and we’re loving our email.
I completely agree. It’s interesting, typically, the people who say, “I don’t have time,” it’s not that you don’t have time. We all have the same amount of time and the question always is, “How can one person accomplish significantly more, produce a lot, develop a lot in the same 24 hours a day that others have.” Most often, the person who’s producing more is busier than the person who’s producing less. It’s all about how you use your time, how you structure it, whether you’re trying to be perfect, hold you back from starting, or you get it done. I’m wondering, one of the offerings is workshops.
With COVID, the in-person workshop has disappeared, and even when things do come back online with COVID, hopefully being in a much better place and containing a lot more. Who knows whether the in-person workshop will ever go back to the way that it was? How have you adjusted your business? What changes have you made, regardless of what happens with COVID, you think, “I’m sticking to this. I’ve learned something that could benefit my business and benefit my clients going forward?”
First of all, maybe this is who I am, I hope in-person comes back. Coaching, you can do one-on-one, but when it’s a group setting, I get a lot more energy by doing it. It’s not all about me but I get a lot more energy when it’s in person because we can all interact a little bit more. I definitely have done a lot of virtual leadership training. A couple of points, do’s and don’ts that I would say, nothing can be more than 90 minutes. If that means you’ve got to do it across a month, then you need to do it that way. I don’t think that people can. We are all Zoomed out. I had a CMO client say to me, “I can’t do one more Zoom. Can we just do coaching as a call?” We have Zoom fatigue or Microsoft meeting fatigue or whatever.
You must prepare a lot more than what you have done in person. This is from all the presenting I did in advertising. This is a stab in the dark. I feel that I have to give four times the amount of energy to keep the room captivated when I’m presenting virtually. It’s even owning it more because you have Joe over here who hasn’t talked in a while. What I mean by preparation too is you have to have a lot more interesting stories. By the end, you should be laying on the sofa because you’re tired. You’ve spent the energy because that’s what I believe Zoom leadership training is about now. It is theater amped to 100%.
Talk to us a little bit about your experience of being an executive coach at the Harvard Business School. How did you land that gig?
It was through networking. I work in the Executive Ed Program, where I work with senior leaders who come to the campus for six months. It’s not an MBA program, but it’s an executive program so it’s senior leadership. It’s coaching, assessments, and all of that.
You met through people at that networking event and someone said, “You should be this person, you’d be great at it. Done.”
Yes. All about this is, at the end of the day meeting interesting people.Take one step that you can control. Click To Tweet
Has that had any impact on your business directly, the people you meet through that program somehow become clients? Have you seen it help in terms of, it’s a good “logo” to add to your website and your repertoire to say, “I’m an executive coach here,” and that adds some credibility? Any big benefit that you’ve seen from a business perspective.
I’m going to take it in a different way. Having things like Forbes, Inc., and Harvard Business Review, yes, they give credibility because at the end of the day, when you’re a consultant, how can you make it easy for somebody that when they sign on the liner you do the work it’s not a risk? Everybody is afraid of risks. I’m not saying that people are lazy. I’m saying everybody’s risk-averse. If you’re new to being a consultant, what are the sound bites you can give that show people you have credibility?
The point on risk is such an important one because you’re right. The number one reason why a buyer does not move forward is because they see too much risk and it might be a monetary risk, time risk, in terms of them and their team having to be involved in a project, it might be wondering, will this person do what they say they’re going to do? How will I look in the organization? At the end of the project, the more likely they are to find reasons to delay, hesitate, or to want to think through things. The more credibility proof that you can put in front of them, certainly, that can help.
Also, this is where the discovery or entry-level offer, where someone can, for example, get going for $5,000 or $15,000, as opposed to $50,000 or $500,000. It makes it easier because it reduces the risk. The point you’re making here is what can you do from all different aspects to reduce the risk for that potential client and buyer will improve your overall sales cycle and help you to engage with them sooner.
It could be as simple as if you’re new and starting out as a consultant or even now, for all of us. Let’s say you spoke at this conference. That’s credibility right there. You have to lead with that. You got selected to speak at that conference, that’s credibility. It doesn’t have to be, “I’ve published my book with Harvard Business Review, or whatever.” There are many different forms of it.
The point you’re making there is a good one because I’ve seen this with a lot of the consultants and clients in our coaching program who have a great deal of experience and expertise but oftentimes, they’re not leveraging it. They’re not talking about that they gave a presentation or they facilitated 10,000 hours of this, that or the other or they’ve been in this unique position. That’s a great reminder for everyone reading. Look at everything you’ve done. Take a full inventory of all of your accomplishments, your results, your outcomes, and what you’ve been a part of.
Look at how you can incorporate that into your website, your LinkedIn profile, marketing materials, and telling your story, because the more of that you do, as Anne’s sharing here, that lends itself to your credibility, your authority and makes your message significantly more compelling. I want to thank you, Anne, for coming on here to share your insights and experiences. Where should people go to learn more about you and your work?
If you go to AnneSugar.com, I have a list of articles you can sign up for and get. These are the six articles that I typically give clients all the time. You can also reach me on my LinkedIn profile, Anne Sugar. I’ve put out a lot of articles and ideas every week there as well.
Thanks so much, Anne. Thank you for coming on.
Thank you, Michael. It’s great speaking to you.