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PODCAST 99: Overcoming Imposter Syndrome and Flourishing at Work w/ Stephanie Blair

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This week on the Sales Hacker podcast, we speak with Stephanie Blair, Founder and CEO of Know and Flourish.

Stephanie founded her executive coaching and consultancy company focused on grooming and growing innovative talent within sales centric and growth focused teams. As an expert in digital transformation and in fueling modern organizations for sustainable success prior to Know and Flourish, she spent over eight years at eMarketer in assorted individual contributor and leadership roles, and before that, the New York Daily News.

If you missed episode 98, check it out here: PODCAST 98: The Importance of Product-Led Growth and Focus For A Startup w/ Blake Bartlett

What You’ll Learn

  • What it means to flourish at your work
  • Where to focus in your first 100 days in a new role
  • What imposter syndrome is & how to overcome it
  • 2 major problems with how organizations are hiring
  • The traits of a mindful leader

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Show Agenda and Timestamps

  1. Show Introduction [00:00]
  2. About Stephanie Blair & Know and Flourish [00:02]
  3. Lessons of leadership [7:26]
  4. Mindful leadership [12:00]
  5. The first 100 days [17:19]
  6. Overcome imposter syndrome [23:23]
  7. How to hire [29:15]
  8. Stephanie’s recommendations [31:23]
  9. Sam’s Corner [33:00]

Show Introduction [00:00]

Sam Jacobs: Hi, everybody, it’s Sam Jacobs. Welcome to the Sales Hacker Podcast. I’m excited to chat with Stephanie Blair, Founder and CEO of Know and Flourish, her executive coaching and consultancy focused on grooming and growing innovative talent within sales centric and growth focused teams.

Now before we get there, we want to thank our sponsor.

Our sponsor is Outreach, the leading sales engagement platform that enables sales reps to humanize their communications at scale, from automating the soul-sucking manual work that eats up selling time to providing action-oriented tips on what communications are working best. Outreach has your back.

Now, without further ado, let’s listen to this interview with Stephanie Blair.

About Stephanie Blair & Know and Flourish [00:02]

Sam Jacobs: Welcome, Stephanie. In addition to founding Know and Flourish, Stephanie helps leaders in their teams more effectively communicate to drive business results. And as an expert in digital transformation and in fueling modern organizations for sustainable success prior to Know and Flourish, she spent over eight years at eMarketer and assorted individual contributor and leadership roles, and before that, the New York Daily News. Tell us a little bit about your career in sales.

Stephanie Blair: Thanks Sam. It’s great to be here. I joined eMarketer from the New York Daily News. I wanted to get to the heart of the digital ecosystem but didn’t want to sell advertising anymore. eMarketer is a leading researcher for digital transformation and it works with everybody from small startups to large Fortune 500 brands — every major publisher agency that you can think of works with them. So I had started by managing a book as an account manager and I found the job to be pretty reactive.

Sam Jacobs: How did you find your way into sales? Tell us about, you know, what were your first job selling? When did you know you were going to be a good salesperson? Walk us through the little bit of that journey.

Stephanie Blair: Well, my friends would say that I negotiate everything and that I was born a salesperson. I didn’t recognize my talent in it until high school. In some of those leadership roles, I really had to advocate for the group that I was supporting. In the case of my musical experience, we had to raise money by selling ads and I was the top seller in that capacity. I knew it came naturally to me, but I didn’t really know what I would do with it. I decided to study international business and French. My goal was to move to France after studying abroad there. (I’m also a French citizen. Fun fact.)

My goal was to move to France, but before I could graduate, I first had to get an internship. I was able to leverage a family connection with Ashley furniture. My dad got me an internship interview and I was able to gain an opportunity supporting the advertising department within the New York Daily News. I liked advertising and was able to create new revenue and get some advertisers on board. After five days of post-graduation, my old boss from that summer internship called me up. Why don’t you just come back here? You’re not moving to France tomorrow, come give us six months and see what you think. And I ended up staying for years.

Lessons of leadership [7:26]

Sam Jacobs: When you think about lessons of leadership, as you’ve seen great leaders and then leaders that haven’t succeeded, what are some of the things that emerged for you? What comes to mind?

Stephanie Blair: There needs to be a certain agility, especially in an environment that is changing so rapidly. First and foremost, it’s about a true understanding about what’s going on and having their finger on the pulse, but then being completely open to change and being tireless in their pursuit of figuring out the new way forward. And

I also think it’s about the whole person, especially in sales. We’re so focused on results and the bottom line and achieving our quotas. But there’s a humane way of doing it where you bring your whole self to the process. The people who do that are the ones who flourish.

Sam Jacobs: Let’s dive into that because the name of your firm is Know and Flourish. Why is it called that?

Stephanie Blair: When I was looking at the other strategic advisory companies, I think a lot of people come in, get a set of recommendations, and leave. I wanted my focus to be on sustainable results. Flourishing to me means sustainability and growth that can live on. It’s one thing to achieve your goal or hit a target, but to do it in a way that really embraced your full set of skills and abilities makes me feel good. I want to make people feel good in their sense of leadership.

Mindful leadership [12:00]

Sam Jacobs: So there’s this phrase “mindful leadership” and you talked about bringing your whole self to work. What does that mean? What’s an example of it?

Stephanie Blair: A mindful leader is someone who cultivates focus, clarity, creativity, and compassion at the service of others. They have the goals and focus in mind, but they do it in a way that really flexes each individual’s muscle. Not everybody’s going to want to be motivated or managed the same way. And so my mindful leader recognizes that, understands the person beneath the resume. A mindful leader is also somebody who recognizes that a top performer could actually be going through a really hard personal time and move things out of the way within the business to make sure that a person gets support in that moment.

It’s a journey, but I think it always starts with an assessment. With the individual I tend to favor something called StandOut. It looks at how you handle situations and what your default settings are as it pertains to work related situations that come up. I also have the client do a 360 Assessment. So we can figure out how they do things and why they do things, not just what they do.

That is really mind blowing for some people who have led global sales or can build a team. That’s great. So can thousands of other people. Why should they hire you? What is unique about your proposition and experience that you can bring to the table? I help them figure that out and build a strategy around that. That’s what’s going to create long term sustainable success, and that’s what I’m all about.

Sam Jacobs: What are some of the interesting or common things that come out of a self assessment? What’s a common gap or area where they need to focus that maybe they didn’t expect?

Stephanie Blair: One example comes to mind about busting their own personal myths. Somebody might come to me and say, Hey, I’m only looking for startups that are series A or series B and that’s it. Then we do this assessment and we find out that actually their super power is solving puzzles, looking at information, seeing trends, and piecing things together. That calls for pivoting their focus to say, I’d actually be better at a series B or C where there’s already been some growth. It’s about helping them match up their unique value proposition with the firm’s opportunity.

RELATED: The Straightforward Truth About Effective Sales Leadership

The first 100 days [17:19]

Sam Jacobs: How do you make a great impact in the first hundred days at a new company?

Stephanie Blair: About a third of the people that I work with are going through a transition. Others are new to a climate or are climbing the ranks within a company. How are you showing up as your whole self and making the mark that you want to make in those critical first hundred days or first two quarters?

It’s about picking your battles and understanding the pace of things. I work with a lot of high achievers, so sometimes their intensity overshadows that of the org that they’re joining. Why don’t we start at 80% for the first couple of weeks, getting up to observation mode? Once you observe the themes, you can rally around two or three core missions. Then it’s about understanding what the political climate is about and where you can make the biggest impact. What are the critical two or three things, the broadest strokes, that will make the biggest impacts early on?

RELATED: The First 90 Days: From “In the Door” to “Successful Sale” in Record Time

Overcome imposter syndrome [23:23]

Sam Jacobs: You’ve spoken a lot about imposter syndrome, and it’s something that so many people relate to. Why don’t you help define it for us and explain how you think it holds people back?

Stephanie Blair: The generally accepted definition of imposter syndrome is the inability to believe that your success is deserved and legitimately achieved and the result of your effort and skill. I see it showing up in a couple of ways. People who have perfectionist tendencies or a soloist, somebody who’s just this like lone wolf — but all the while they’re doubting themselves. Should I be at this table amongst these great leaders or not? A 2011 study said that 70% of people will experience it at one time in their life.

It can impact anybody. It’s important to acknowledge it, not hide from it, and then try to use it as fuel to say, Maybe I have gaps and that’s okay. Let’s work on filling them or working with a peer or a leader in my organization to identify if my thinking about my gaps actually are the gaps. It’s about arming people to acknowledge it and figure out their way forward.

Sam Jacobs: As an individual, if you’re out there and don’t really know what you’re doing even though you’re everybody you do, how do you know the difference between what’s valid and what’s not?

Stephanie Blair: That’s probably the toughest question you’ll ask me. First of all, it’s acknowledging that everybody’s felt like this, even if they don’t admit it. So, number one is just to normalize it. A mindful leader is also a leader who recognizes that your job is never done. We’re always on a pursuit of learning, of excellence. In that spirit, you can apply that to your imposter syndrome. It’s about parsing it out and saying, What is just like fabricated in my mind and what is something that I can actually move forward with? Have an accountability partner in this. Have an open dialogue with your direct manager about this, or if you’re a leader, have it with your teams

Perfection is not the only acceptable result.

How to hire [29:15]

Sam Jacobs: We need to rethink, uh, how we make companies attractive to young people in their twenties. What do you think we should do to improve our hiring process to make it more effective?

Stephanie Blair: It’s important that the firm who’s hiring has a clear set of values and expectations. That will make everything easier because then they can also be seeking value alignment and philosophical alignment. More tactically, the people who are interviewing for that next head of customer success or head of rev ops, they can all align on what both soft skills and practical skills are needed so that when they are interviewing a variety of candidates it has to be more thorough, more thoughtful.

I also hear way too much about ghosting happening. That’s just really not acceptable in this day and age. I mean, time is money. People are really putting their all into preparing for interviews and for the process — only to knock you back for weeks at a time. Be really clear about what is your intention for this search and what the candidate can expect in the process.

RELATED: Hiring Sales Reps: How to Recognize Top Performers BEFORE You Hire

Stephanie’s recommendations [31:23]

Sam Jacobs: We like to pay it forward a little bit and hear about some of your influences, some of the people that you respect, or some of the content that you’ve been consuming recently.

Stephanie Blair: Like a lot of revenue leaders and business leaders, I love The Advantage by Patrick Lencioni. I also suggest Brave New Work by Aaron Dignan.

I love Sales Hacker for actionable sales tips. And for women in the workplace, I think The Broad Experience is a fantastic podcast.

Contact Stephanie on LinkedIn to continue the conversation about how to flourish at your work.

Sam’s Corner [33:00]

Sam Jacobs: Hi, everybody, it’s Sam’s corner. I really enjoyed that interview with Stephanie Blair. She mentioned that making and creating an environment where people of all generations want to succeed is having a malleable definition of the job. How do you create an environment where people can do the things they have to do, but they also feel like they’re making a positive impact on the business and their voice is heard?

We also touched on this concept of imposter syndrome. Some part of it is leap before you look. If we’re looking for parity in the workforce and diversity, part of it is you just have to make sure that you raise your hand and you tell yourself, Yes, I deserve this opportunity. I’m going to jump at this opportunity. Second part of that is understanding that everybody has this. You are not alone. Create some mechanism through which you create positive affirmation about your self-worth.

What We Learned

  • What it means to flourish at your work
  • Where to focus in your first 100 days in a new role
  • What imposter syndrome is & how to overcome it
  • 2 major problems with how organizations are hiring
  • The traits of a mindful leader

Don’t miss episode 100!

I hope you enjoyed the show. Our is Outreach, the leading sales engagement platform

If you want to reach out to me with feedback, you can find me on LinkedIn. If you haven’t rated the show, please give us 5 stars on the iTunes rating system so that we can remain in business and continue to bring you this show.

As always, thanks so much for listening, I’ll talk to you next time.

This is a sponsored guest post from a Sales Hacker partner.

Sam Jacobs is the Founder of Aqueduct Revenue Advisors and the New York Revenue Collective and regarded as one of the top start-up CROs in the tech community.

He has has over 15 years of experience scaling companies from post-revenue to ~$300M, has helped raise over $400M in institutional capital, and has helped companies of all sizes achieve an average annualized revenue growth rate of 48% over the last 15 years.