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Become The Clear, Confident & Centered Leader That Your Team Needs

Through The Uncertainty of .

Become The Clear, Confident & Centered Leader That Your Team Needs Through The Uncertainty of .

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Alana is what you want in a coach.

She has been there and brings vast experience to the table. I’ve known Alana Winter for 20 years. She possesses a rare combination of savvy, successful entrepreneur who also understands the human side, and can teach it to you.
- David Bach
- David Bach

Alana helps everyone become a better person.

She’s a true leader, a transformational leader. She’s gentle, but firm. She listens to find the insight that is so hard to find on your own. She helps people find their power, see their own mastery, and act. Many teachers help with the tangible. That’s great. Alana helps you learn the intangibles — that’s transformational.
- Chip Conley
- Chip Conley

If You Want to Succeed at Scale... Work With Alana

Becoming an entrepreneur isn’t easy. Becoming a successful one is harder still. It means more than understanding root problems and solving them, it means learning to learn.
- Naveen Jain
- Naveen Jain
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Whether You’re Leading Through Significant Growth, or Navigating Through Chaos or Crisis, You’re Probably Facing These Exact Challenges...

  • You’re under more pressure than ever and there’s never enough time
  • You are facing more difficult decisions that you’ve never had to make before (and you’re afraid of how much making the wrong decision will cost you)
  • The stakes for “getting this wrong” are higher than ever (what worked to achieve your current level of success isn’t working the same as before, and the cost of “being wrong” may lead your company and team to disaster)
  • You’re struggling to balance your work, family demands and self-care (and you’re way overworked)
  • You can’t seem to get your team all working together around aligned priorities, so they are stretched and overworked, without making the kind of progress you know is possible.
  • You’re way overcommitted (your leaky personal boundaries and tendency to be a “people pleaser” are finally catching up to you… and you just can’t seem to “catch up”)
  • You can no longer afford to say YES to every “good opportunity” that comes your way… but it’s hard to say NO to revenue. How do you prioritize?
  • You’re in new territory. Your old playbook isn’t working anymore, and you lack the trusted guidance to be the clear and confident leader your team needs. You don’t know who to turn to, and there are days you feel lost and alone.

The Good News is You’re Not Alone

Every CEO, entrepreneur and leader who has scaled a company has faced these exact challenges.

You need a trusted sounding board who has “been there, done that” and has coached others through the exact inner and outer game you’re playing now.

On the other side of your current challenges, there is significant scaling and personal peace available.

After 20 years as a serial entrepreneur building my own companies (including several exits) and 13+ years of personally coaching thousands of entrepreneurs and their leadership teams, I’ve discovered that scaling successfully comes down to aligning your two WORLDS: your inner world and outer world.

BOOK A CLARITY CALL

YOUR

Internal World

  • Core values alignment
  • Clarity on your priorities
  • Balance and boundaries
  • Your entrepreneurial psychology
  • Clear and effective communication
  • Your key drivers and your fears
  • Awareness: seeing what’s really there (in yourself, others, your business and the marketplace)

(LIST: values, alignment, fears, clarity, boundaries, balance, priorities, clarity on priorities, psychology / drivers / motivators, communication, etc)

I get what’s going on in your mind and can help you navigate chaos with calm and clarity by raising your awareness and finding alignment.

YOUR

External World

  • Your team (who to fire, who to hire, and how to lead them)
  • Your business model
  • Pivoting (maximize upside and minimize risk)
  • Marketplace opportunities
  • Securing funding
  • Strategy and tactics

(LIST: team members, hiring, systems, opportunities, funding, strategy, pivot, business model, etc)

My range of experience makes me a great strategic sounding board, and my vast network gives me quick access to the tactical solutions you need.

The best way to discover how I can help you is to book a Clarity Call, where we’ll gain clarity on exactly what your most pressing challenge or opportunity right now and how I can help you.

  • Business challenges (tactical or strategic)
  • Personal and leadership challenges
  • Pivots
  • Finding opportunity through uncertainty

I offer sliding scale scholarships to select entrepreneurs in need during these unprecedented times. If that’s you, mention that in your application. If you’re thriving and I can help you through growth challenges, your fee will help subsidize an entrepreneur in need (and may even save jobs).

Ready to gain crystal clarity on your most pressing challenge?

BOOK A CLARITY CALL
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How I can specifically help you

COACHING

Executive Leadership Coaching

Upgrade your leadership, decision making, and communication so you can lead with confidence through uncertainty (whether you’re growing fast or facing crisis).

RETREATS

Leadership Team Retreats

Get rock solid alignment on your company-wide values, purpose & plan. Unlock greater unity, a singular vision & mission, higher performance and rocketfuel for scaling.

FORUMS

Forum Facilitation

Private forum facilitation for your CEO peer group to become more open, connected and effective. Over 1,000 individuals have benefitted, including peer groups in Young President’s Organization (YPO), Entrepreneur’s Organization (EO), WPO, Harvard Business School Alumni Forums and various private communities.

WORKSHOPS

Team Workshops

Support your employees and team members so your company gets “unstuck”. Through sequential exercises, conversations and brainstorming upgrades, your organization will become more connected and effective, so you can scale smoothly, rapidly and intentionally.

Success Stories

I’ve Helped Hundreds of Leaders
Like You and Their Teams Transform

Alana is what you want in a coach.

Play Video

David Bach
10 X New York Times Bestselling Author Founder finishrich.com & Co- Founder AE Wealth Management

Alana helps everyone become a better person.

Play Video

Chip Conley
Founder Joie de Vivre Hospitality, Fest 300, Modern Elder Academy Former Head of Global Hospitality and Strategy for Air Bnb Multiple NYT Best Selling Author San Francisco Business Times Most Innovative CEO

If You Want to Succeed at Scale... Work With Alana

Play Video

Naveen Jain
Founder of Moon Express, Viome, World Innovation Institute, iNome, TalentWise, Intelius, and Infospace Ernst and Young's Entrepreneur of the Year Silicon India's Most admired Serial Entrepreneur

see more success stories
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Clarity Blog:

Wisdom

To Help You See What’s Really There

Blog

You’re Only Here Once

My Uber driver has a 4.95 rating so I asked him what his magic is. Here’s what he shared. He works in the care field. …

Read More
Blog

Where The Magic Starts

It’s fascinating that as humans, we’ve been saying the same stuff for centuries, constantly thinking it’s a new revelation. “We are what we think. With …

Read More
Strategy

Take Nothing Personally

Read More
Personal Growth

Optimism in Human Nature

Read More
Personal Growth

STRESS! Let’s talk about It

Read More

Want more

Wisdom?

read the blog

MY STORY

“What business are you going to open up when you grow up Alana?”

It’s 2006 when my attorney calls and says, “Alana, your company is officially sold!”

I respond flatly, “Oh ok, thanks,” and end the call.

Suddenly, I feel like I’ve been set out to drift in space and just received the last communication from Earth. I know all the business calls and emails are over.

My friend says, “That’s amazing. You sold your company!
What do you want to do now?”
I reply, “Get an ice cream?”,
…but all I’m thinking is,

“Who I am now?
What do I do with my life?”

read my story

Connect with me

The best way to discover how I can help you is to book a Clarity Call, where we’ll gain clarity on exactly what your most pressing challenge or opportunity right now and how I can help you.

BOOK A CLARITY CALL

Ask Yourself These 10 Critical Questions To Gain Greater Clarity Over Any Challenge

WATCH THE TRAINING
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