Stepping into leadership means that we guide our team toward the big-picture mission and keep positive momentum going day-to-day. Teams have objectives to work toward and it’s up to the leader to design the approach and drive progress. There is a long, continuous path to collectively take on together. Over time, amongst the day-to-day work, team members often lose sight of the big picture mission and objectives, the progress that is made, and where attention should really be placed. When the team loses sight of achievements and isn’t clear in terms of what is truly building toward your definition of “success”, frustration builds instead of positive progress.

I began acknowledging and documenting individual and team wins when I realized the need to positively motivate my team, periodically lift us out of the weeds of the work to see the big picture, align our focus around what really matters for us to achieve success, and build our collective confidence.

Spotting instead of Seeking Approval

Early on in our careers we look to management, human resources, and leaders to approve our work and define success for us. However, stepping into leadership means that you start to determine what success is for you and your team. It’s helpful to have a leader there as well to guide you and support you in what you offer, however, work becomes more meaningful and you truly become a leader when you are the ultimate approver of your own work.

When working in a company, you do have to make decisions on behalf of the organization that are in line with the brand and company direction. However, taking a leadership position means you can make authentic decisions on behalf of the organization that also reflect your own discernment. You take ownership over your own work. You start to think independently and lead by example.

To move from following or managing to a position of leadership, you must shift to a mindset where you can approve the content and quality of your team’s work and contributions. You must do this initial work of being able to define what success means for your team and identify the actions that truly contribute.

What Qualifies as a Win

Once you can define what success really means for your team and the actions that contribute toward that success, you have the ability to spot wins. Wins are actions, small or large, that contributed toward the team’s progress. They are meaningful milestones on the path to success. Wins can be anything from completing a project, to making a new connection, to coming up with a new idea, or hiring a new team member. Sometimes a win is feeling more consistently happy and healthy. Sometimes a win is eliminating something like a project or process that doesn’t serve the mission. Wins are a lot about closing the loop and a lot about discovery and opportunity. Most often a win is finally completing something that moves you closer toward fulfilling your team’s mission.

Great leaders have the ability to tie specific actions back to the overall mission and show team members how they contributed to it. This practice allows the team to understand what success means for the team and the type of actions that constitute big progress.

As a leader, I would identify and document our wins (important individual and team contributions) every Friday and share them during our team meeting. I found that it is a way of pausing to acknowledge the progress we made and, importantly, brings collective understanding and focus to the type of actions that really brought us closer to our mission. I also found that things that were not acknowledged as wins could often be eliminated so we could focus more on the things that generated true wins. Ideally, everything eventually could constitute as a win. So, overtime, larger milestones only become the criteria for a win.

Power of Documentation

Documentation is powerful because we have to spend time reflecting and see it in front of our eyes. We don’t just skim over it in our heads or talk about it. We document it for ourselves and our team to see, visually, so we are all aligned. People understand and remember information through different mediums so both hearing and a visual communication is important. Documentation also allows us to go back a review progress from the past and continue to reflect on our progress and how we built our success over time. I recommend not just identifying and talking about wins but actually documenting them.

We often start doing a million things in many directions and lose sight of what the real wins are that contribute to our successes and our happiness. Pausing to acknowledge wins and express gratitude for where we are and what we have accomplished provides a foundation for improvement. We realize what was important and what our definition of success truly is. We can better move forward with more focus on the things that matter.

In my new book, Awake Ethics, I offer a similar exercise to the Friday wins where I ask leaders to document their wins and learnings and share them with the team. This exercise is in the Contentment section of the book. Contentment is strongly linked to confidence and by sharing and documenting our wins often – for ourselves and for our team – we also build the confidence to continue and to improve.

To put something very deeply impactful into very simple terms, leadership is a lot about having the ability to be able to understand, define, and communicate what constitutes as a win for your team – what is building toward your mission and true definition of success. Acknowledging this further aligns the team around the mission and brings focus to what type of actions and contributions are most fruitful. It also builds confidence. This is a game-changer for your team. Leaders that cannot clearly define success and communicate small and large wins for the team find the team stagnates due to lack of motivation and clear direction.

Document your wins to align the team around actions that truly contribute toward the mission, fuel momentum through positive acknowledgement, and serve as a mirror for the team’s progress toward success.


People love to see progress. People love acknowledgement for thing that truly made a difference. This informs the next forward action.

Document wins to continuously improve, to define success on your terms, align your team around intentional action, and ultimately build confidence. I also do Friday Wins personally, in my own journal, for myself. It’s satisfying and motivating to look at my wins each week. When there aren’t a lot of wins, I think about what’s coming up the next week and how it could be better. I realize that every week is different but there is always progress, small or large, to have gratitude for along the path.

How do you practice Contentment? What are you wins from this past week?