Get Clear On Winning – It's Personal!

by Holly G Green

Get Clear On Winning - It's Personal!Last month I had the opportunity to speak at Microsoft’s annual Worldwide Partner Conference. As one of the featured business session speakers, I addressed a lively audience on two of my favorite subjects: the importance of getting clear on winning, and engaging employees in reaching the organization’s destination.

At the end of my presentation, we had an open-mike session for people to ask questions. Most of the questions revolved around how to take the ideas I had presented and put them to work on a day-to-day basis at work. This came as no surprise, as these days people get hit with so much information that they often struggle to implement it in a meaningful way. The #1 question on everyone’s mind seems to be, “How do we incorporate what we learn into new and better ways of working?”

What did surprise me was the number of people who asked about implementing some of these principles in their personal lives. I don’t claim to be a life coach or personal development guru. But the concept of getting clear on winning can certainly be applied beyond the workplace.

In the business world, one tool for painting a vivid picture of where an organization needs to go is called “destination modeling.” This consists of establishing destination statements in different areas of the business that make the picture of winning more tangible and real.

Designed to create powerful visions in the minds of employees, destination statements provide cohesion, direction, and behavioral guidance. They tell employees what the organization is doing now, what it isn’t doing, and what it will be doing when the destination is reached.

To adapt this process to your personal life, I suggest establishing destination points in five categories to serve as a good starting point – family, health, finances, personal development, and professional development. Feel free to add others that work for you.

Start by deciding where you want to go (your destination) in each of the areas. Choose a timeframe (and I recommend no further out than 18 to 24 months based on the pace of change in today’s world). Determine what it looks like when you get to it. For example, family: I will have deeper, more meaningful relationships. Finances: I will have set aside $X for retirement each quarter. I will be paying myself first by making a deposit into my savings account before anything else each month. I will have paid off my credit card debt and have a system in place for tracking all my debt to better manage it.

Next, divide a sheet of paper with a vertical line down the middle. On the left side, write down the category. On the right side, describe what it will look like when you have reached your destination in that category. For example, when we have achieved our “family” destination:

  • How much time are we spending together?
  • What activities are we engaging in as a family? How often?
  • How are we communicating with each other in a more loving, respectful way?
  • How are we resolving problems and conflicts more effectively than we do now?
  • What new relationships have we formed with extended family?


  • What numbers have I attained in terms of weight, cholesterol, etc., to achieve optimum health?
  • What kind of exercise and diet changes have I made to achieve those numbers?
  • How am I managing stress more effectively?


  • What specific financial goals have we set, and why?
  • What tools are we using to achieve those goals?
  • What are the biggest obstacles to achieving our goals and what strategies are we using to overcome them?

Personal Development:

  • What am I doing to grow as a person?
  • What new hobbies or interests have I developed?
  • What community activities am I involved in?
  • How am I contributing to making the world a better place to live?
  • Where do I get energy and how am I incorporating more activities that align with that into my life?

Professional Development:

  • What are my career objectives?
  • What new knowledge or skills have I acquired to achieve them?
  • What am I doing to obtain that knowledge or skills?
  • Who am I using as a mentor or coach to help me get where I want to go?

Once you have identified your destination points, measure each one against the following criteria: Is it easy to understand? Does it tell you what you need to do and not do? Does it provide enough details to be tangible and measurable? Is it flexible enough to adapt to evolving circumstances?

Most of all, does it compel you to want to go there? If your destination doesn’t excite and inspire you, chances are you won’t do what it takes to achieve it.

Whether in business or sports, the top performers all have a clear vision of what winning looks like. The same holds true for our personal lives. I saw the perfect t-shirt to go with this blog the other day: No one practices to lose! You are practicing each and every day in life, so get clear on where you want to go in life (what is winning to you?), set your destination points, and enjoy the journey!

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Holly G GreenHolly is the CEO of THE HUMAN FACTOR, Inc. ( and is a highly sought after and acclaimed speaker, business consultant, and author. Her unique approach to creating strategic agility, helping others go slow to go fast, will change your thinking.

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