Top Performers Define Winning In Great Detail

Over the past three years, we have collected over 10,000 nomination submissions on the top executives and leaders in the software industry.   Parsing the data we find some common themes of what makes for a high performing professional in the industry.  In a series of articles, we will provide helpful strategies, in what we like to call ‘All In’ insights, to optimize effectiveness in whatever position or role you may be playing within your organization.  Our view is that leadership is not confined to executives and managers but is a skill anyone regardless of position can practice and develop. 

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In his book 7 Habits of Highly Effective People, Steven Covey taught us to ‘Begin with an end in mind’.  What we found in our data lined up well with this piece of wisdom.  People who were high performers knew exactly the results they hoped to accomplish.  They were very clear in defining what winning was at the outset of undertaking a new project or starting a new month or quarter.  But to define and track winning is not so simple, one must expand on the concept to ensure it is properly put to use. 

Goal Optimization

The process of goal setting begins with understanding what the broader objectives are of the organization and group one is in.  It also involves understanding the strengths and weaknesses of the individuals within a group.  If an organization is considered the large incumbent in an industry that is much different than being a relatively new entrant.  Also, each group within an organization has a specific function and expectations are set by the heads of the organization on what that group should achieve. 

In essence goals should be aligned and optimized.  They should be aligned with the needs of the organization, whether that be to hit sales targets or achieve certain customer satisfaction scores.  Goals should be optimized in that they should stretch the group to perform at their best.  If goals are too easy to accomplish they will not only be uninspiring to all involved, they will waste the time and resources of the organization.  Moreover, with optimized goal setting there is a higher likelihood of sustaining an engaged workforce.


Once the qualitative aspects to a goal have been identified, the goal must be made specific.  The clearer a goal is the better the chances of achieving such goal.  For example, in a sales team, goals can be set for the number of new customers to be acquired in a quarter, but that can be further defined by the number of new customers per sector or per company size range.  Careful thought should be spent on uncovering what the right specific goals should be.   Smart specific goals set the team on the right course not only in the near term but for the long haul. 

Specificity can have a compounding effect.  Take for example, the decision to focus selling software into a particular sector.  Once action has been taken through email outreach, marketing material, conference attendance and ultimately relationship cultivation, momentum has been built up and can lead to easier wins in that sector down the road.  Frequently, the most difficult part of a new undertaking is getting started and over time through inertia or simply presence, customer and other types of ‘wins’ are easier to come by.


After a goal has been appropriately scoped and specified, it must be measured, most likely in either numeric or financial terms.  What we measure on a continuous basis becomes what we are most focused on.  So with setting specific goals, we must also think in parallel about how that goal will be measured and how often.  Through measurement, we know how close or far we are from the goal’s attainment.  We also know the level of action, massive or minor, we need to deploy to keep the group on track. 

Measuring goal attainment against specific numbers helps a team face reality and remain objective about performance.  It also holds everyone involved accountable.  It provides a bright line at each moment of execution, whether that be over a month, quarter, or year, so that improvement can take place before it is too late.  Measurability of goals can lead to optimized performance and the attainment of excellence, but just as valuable, it can prevent groups from derailing or going too far astray from the right path.


Defining what winning is can be one of the most important things a leader does.  It sets the course for a team of people and ultimately determines where that team and the broader organization ends up.  The process of defining winning, however, is more than just setting a target, it holds people accountable and makes more tangible the feeling of whether or not a game, or in this case, actual business, was won or lost.