3 Leadership Lessons from Steve Schlafman, Professional Certified Coach

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On this week's podcast, I spoke with Steve Schlafman. Steve is a certified professional development coach and angel investor. Steve is the founder of High Output, a boutique leadership development company. His previous positions were a VC at Primary Venture Partners and RRE Ventures. Some of his select investments include Boom, Breather, and theSkimm.

We discuss why Steve left VC to coach, Steve's leadership and coaching philosophy, and the importance of building a personal brand.

Why You Should Listen to this Episode?

Steve is a well-known investor and coach. He has 48K followers on Twitter. Steve is a frequent guest on podcasts talking about investing. So I was excited to talk with him about a different topic—coaching. If you are looking to take your career to the next level or an executive trying to figure things out, I recommend you listen.

Ari's Three Actionable Takeaways for Marketing, Branding and Communication Professionals:

1) The Best Laid Plans Often Go Awry

Steve didn’t plan to be a coach. He thought he’d be a VC. But one day, he went into his partner's office and told him he was leaving. He realized coaching was his career path. His advice to listeners was not to plan. Spontaneity has driven his life.

His advice is a good reflection of his work. There isn't a fixed process for each client. He looks at his engagement as an "arc of engagement". This is because every person he coaches his different. The CEO of a Series C company doesn't have the same issues as a CMO finding their next gig. What's more important is giving his clients the tool to succeed, no matter the situation.

2) Combine the "Inner Game" and "Outer Game" to Create Success

Steve focuses on two areas for his coaching:

  1. "The Inner Game": The experience of navigating the ups and downs of your professional and personal life. "Who am I at my core?"

  2. "The Outer Game": The strategy, tools and tactics to succeed on a personal and professional level.

Some people want all the answers to their problems. Yet others are willing to figure out how to find the answers but don't know who they are. That's why it's important to combine the two. Your experiences dictate the strategy, tools and tactics to succeed. You can't create the strategy, tools and tactics if you don't have the experiences.

How does Steve start this process? His job is to ask questions, not provide advice. There are three questions that he uses with clients:

  1. What do you value?

  2. What do you stand for and how will you articulate it?

  3. Who is your audience and how can you reach them?

Once clients begin figuring out who they are, he goes deeper and helps them think about execution. The big question they work on is the strategy. He frames it as, "How do we attack this and bring it to life?"

The majority of the clients that come to him are willing to change. He doesn't need to convince them that is the right thing to do, just help them find the "right" path.

3) Building a Personal Brand

Steve has done an amazing job of building his personal brand: he has a large online presence, a fantastic personal website, but also goes out of his way to help. Recently, he launched the High Output Founder's Library. Many times, clients would ask a lot of the same questions. He would send them the same links and thought why don't I democratize this? It wouldn't only be good for his brand, but help founders who didn't have the resources to hire him. There are now hundreds of resources on topics like fundraising, hiring and remote work.

The biggest recommendation Steve has for building a personal brand is going deep on a platform. He has been on Twitter for 13 years. If he tried to spread his time between Twitter, YouTube, and a podcast, his growth might have slowed. Some people aren't sure what to start with so Steve says experiment. Choose a platform and see how things go. If you find success, scale it up, if not try something new.

My favorite part of the conversation is Steve's three rules for coaching conversations:

  1. The conversation is confidential

  2. It's a judgment-free zone

  3. It's about helping the client get where they want to go

Ultimately, Steve's job is helping unlock the answers the client is looking for.

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