Dream Team Retention Recipe – 10 Ingredients to Keep the Team Together and the Dream Alive

Dream Team

Why are your top performers starting to leave? Do NOT read this article if you are building a commodity based business. If, however, you are establishing a dynamic, visionary organization…

The Dream Team Journey

First, let’s take a trip. Your idea is more than a concept. You have kickstarted the initiative and recognize that surrounding yourself with a great team is essential to your organization’s enduring success. The trip can be viewed by three perspectives: The status of the business, founders and peers, and your dream team.


  • Status – You are a great recruiter with a lot of passion around your startup and have attracted some all-star talent.
  • Peers – As a founder, you’re not alone. This is a vibrant party.
  • Dream Team – Top performers are often attracted to the challenge of new and lofty goals.

Seed Stage – Startup Funding Life Cycle


  • Status – You have succeeded in achieving your initial goals, gained revenue and received funding.
  • Peers – Your founder companions are thinning. This is a country club and comes with a certain air of accomplishment.
  • Dream Team – The excitement of success and high-paced growth is like a drug to many top performers.

Early Stage – Startup Funding Life Cycle


  • Status – Perhaps you hit the target, investors are getting a solid return, expansion plans are underway and you are working to build a company that will last.
  • Peers – The vast majority of founders never reach this point. This is an exclusive fraternity and few meet the prerequisites for consideration.
  • Dream Team – Why are your top performers starting to leave?

Growth Stage – Startup Funding Life Cycle

Putting together a Dream Team is great, but keeping a Dream Team together is amazing!

We’ve seen it over and over. No initiative is immune – sports, bands, clubs and companies all face the same dilemma. How do I keep this team together? Once the award is won, track goes platinum, rally cry is heard or breakthrough accomplished, the people who helped get you there begin to move on.

Is there a way to stop this? Is it possible to keep the Dream Team together?

I am fortunate enough to lead a growing information technology services company, Intellithought. The IT industry has the second highest turnover rate of all business categories in the United States (second only to fast food). However, the voluntary turnover rate at Intellithought is ridiculously low. In fact, only one member of our core team has left in the last 5 years.

We have been in business for nearly 18 years. We’ve seen many IT companies come and go. Yet, we are established and growing. I can’t imagine the risk-reward excitement we all felt in the early 2000’s has endured. Nonetheless, I work with a Dream Team of top performers, and most of this team has been together since I was able to purchase the company 10 years ago.  So, what’s the recipe for success?

10 Ingredients in Keeping the Team Together and the Dream Alive

Everyone wants to be well-compensated, but Dream Teamers expect to be highly-compensated. I have found that this is the key factor in keeping your team together. The thing is, I am confident that every member of Intellithought’s Dream Team could increase their salary by moving to another organization. Why then, have they stuck together? Compensation comes in many forms.

  1. Competitive Salary

    Wait a minute. Didn’t I just indicate that it’s not all about the $$$$$$$? Yes, but don’t be mistaken; none of these results will matter if you are not treating your team fairly.

  1. Divorced Compensation

    The org chart should not be married to the compensation ladder. Fill your org chart in accordance with strength and skills required for the title. While doing this, keep compensation directly tied to value brought to the organization. An extremely gifted programmer could make more than a director of operations, even though they are separated by two levels on the org chart.

  1. Involuntary Turnover

    Our team loves working with other top performers. They learn from each other and their competitive spirit drives them to be even better. They are also happy to work with bright, capable, highly-motivated junior players. However, they are not willing to carry a slacker. While we seek to hire only those who we believe can play with the best, we sometimes miss the mark. Dream Teamers have little tolerance for low performers. One of the most important decisions we assess with an up and coming player is whether or not they are a drag on the team. If so, firing them is essential to retaining the core team.

  1. Individual Benefits

    Of course you will need to establish a package for retirement, healthcare, and time off… but don’t stop there. I was once scolded by our HR Director for providing diverse “benefits” to team members. She told me that this was not “fair”. My response was that I treat every single person differently – how could I possibly be more “fair”? Every member is an individual with different dreams, desires, expectations and situations. One needs the ability to work from home on occasion. Another has to pick up his daughter from school every day. Someone else craves the freedom to start his own side venture. This guy likes to sleep late. She wants to get home early. All of these are seen as “benefits” of the job. So, while everyone gets the same standard benefits package, be sure to account for the individual benefits of your Dream Team.

  1. Process Freedom

    Most organizations claim to be ‘results driven’; however, many of those same companies establish guidelines, dress codes, work hours that have nothing to do with predetermined goals. If you truly have a Dream Team and communicate goals clearly, the players will understand what is necessary to accomplish those goals. They will make good decisions – not because the guideline says to, but because they understand what it takes. They’ll dress appropriately – not because the dress code says what to wear, but because they are professionals and understand the environment they are working in. They will work hard – not because they need to punch the clock, but because they enjoy working together and understand what it takes to get the job done.

  1. Team Synergy

    Freedom is not synonymous with anarchy. Every organization needs processes; however, most organizations use them as a crutch. I have one simple rule of thumb on processes – never use a process to solve a resource issue. If a team member is out of line, deal with the problem. The only time a process should be implemented is when it has the ability to streamline and improve efficiency. Processes should be viewed as guardians of freedom in that they keep everyone on the same page, reducing opportunity for unnecessary fires. Anytime you believe a process needs to be instituted, have your team members contribute to its design. This will not only result in a better process; it gives your team ownership of the approaches they are committing to.

  1. High Expectations

    I have found that ideal members are highly motivated. Expect more of them than you would a bench player. Having something just beyond the reach of a good team member motivates great Dream Teamers and gives them an opportunity to show off. Call it conceit if you will, but stars are made to shine.

  1. Assigned Outcomes

    “What” and “why” are essential questions to answer when assigning projects. “How” should rarely be part of the assignment. While you may know “how” you would handle the task at hand, there are always other approaches. In fact, there are generally better approaches. I have found that my team is better at what they do than I am. Telling them “how” to accomplish something as opposed to “why” we want to accomplish “what” stifles creativity and limits their opportunity to be the best version of themselves. This can create frustration within team members.

  1. Complete Clarity

    Communicate often and with crystal clarity. Team members will instinctively fill the gaps of ambiguous directions, goals and visions. The thing is, Dream Teamers’ expectations for themselves are equally as high (if not higher) as your expectations for them, so negativity usually occupies those gaps. This is an area many leaders fail to make a priority, which leads to a breakdown in company culture.

Clarify the Vision – 10 Questions to Create an Effective Vision Statement

  1. Insightful Leadership

    There are countless podcasts, seminars and books on the topic. One thread most of these materials contain is the concept of “servant leadership”. This idea is often misunderstood and therefore misapplied. The concept is best summarized as: “Make what’s important to the team, important to you.” Conscious effort and time spent by leadership on this specific thing will go a long way – keep the ball rolling and the Dream Team together.

Organizations with Dream Teams that endure understand these factors and create a compensation culture that is very sticky. Give me your thoughts in the comments below.

Matthew Cleek

Matthew Cleek is a serial entrepreneur and is a co-founder of FundingSage, which provides valuable information, tools and resources to entrepreneurs seeking to start, grow and fund a business. Matthew's business ventures include Intellithought, theEclassifieds, Spectrum20, Theme Spectrum and more.