"Play chess, not checkers" with your sports business career

by bob hamer - president & Founder of Sports business solutions | July 23, 2019

I’ll never forget the first time I heard this advice. I was a young salesperson for the Phoenix Suns and I had been approached by another team with an opportunity to become a sales manager. On the surface I evaluated the two positions. The new role was something different. It was exciting, there was more responsibility, more money and when I compared it with my current role, there really was no comparison. I was excited about the immediate career growth. So naturally it made sense to go after it right?

Not necessarily.. I did then what I recommend every young professional should do first, discussed it with my mentors and current boss. This is where I first heard the analogy: You have to “Play chess, not checkers” when evaluating career opportunities in sports business. Not that checkers doesn’t require strategy, it does, but the game is simpler. The pieces only move a couple ways and often times you make one move to get your opponent to respond. They do, and then you respond. It’s short term thinking. In chess, due to the nuances of the game, the differing values of each piece and each moving differently there is much more strategy involved and often times you have to think 3 or 4 moves ahead when making your decisions. It may require sacrificing a pawn and short term gain, for the longer term bigger prize.

Completing the analogy and making this applicable to our careers in sports, when evaluating career decisions you can’t compare two opportunities and make a short term decision (checkers) that you feel will make you happier now. You have to be strategic with your career and think long term (chess) and where you ultimately want to be. The chess moves you make with your career are setting up the big move. It’s not about climbing the ladder the quickest, it’s making sure you’re in a position that gets you where you want to be down the road.

I wanted to share some thoughts with you on how you can play chess when evaluating moves in your own sports business career:

1. Brand power and prestige – When you’re around a successful business unit, people will notice. You benefit from the prestige of the system. It’s the reason why super bowl winning coordinators go on to become head coaches. People want that championship pedigree and you’re successful by association. The minute you leave that for a new opportunity, although the title and money is better, you run the risk of not having that. If you’re with a team that is achieving success and looked at as a leader in the industry you’re going to continue getting looks, so don’t just take the first one you see.

2. Knowing you’re next in line – The most common reason for leaving a job is that your boss is in the position that you want and they aren’t going anywhere. If you’re being told you’re next in line, and if your ideal role is with your current team then it’s worth the short term sacrifice of waiting it out. Now, if that role will never present itself, then at some point you may have to look at other options. If you know you’re next up if/when something happens, it’s worth staying and should make it much harder for you to leave.

3. Learning new skills – The big roles often require a knowledge of multiple business units and experience working within them. If you take a job for title or money, and then you aren’t learning or developing those skills, you may get overlooked for the next job because you don’t have the experience or skills needed to do it. Before taking the new job, make sure you will continue to be developed and given the chance to grow your skills in other areas of the business.

4. The opportunity to make an impact – The new brand may be prestigious, the new boss may be great but if the business is in great shape, there isn’t any inventory, or if they’re already successful it may be tough to show what you can do. Be sure that when you take a role, there is the opportunity to make an impact and show those results on your resume.

5. Check all the boxes – It’s hard not to get distracted by the glitz and glamour of the pretty new job and the dollar signs. Remove the emotion and be objective. Don’t sacrifice things that are important to you, and be certain this job positions you best for the one after that and those in the future. It must check all the boxes and be realistic both short and long term. Can you live in the city? Is the team/brand strong? Are the finances there? Will you grow, be developed, and learn the skills needed for the next job? Can you make an impact? If you have to sell yourself on the role, it’s not worth it. You should hold out for the one you feel more confident in.

When evaluating career moves, you have to think long term. Short term it’ll be no comparison, but making the wrong move can set your career back. Be strategic, be objective and although you may have to be patient and sacrifice some pawns along the way, remember it’s about positioning yourself for the big job down the road. When you finally say “checkmate” and land your dream job, I promise you it’ll all be worth it.


Bob Hamer is the President and Founder of Sports Business Solutions and creator of theClubhouse. SBS provides sales training, consulting and recruiting services for sports teams and through theClubhouse they provide educational information and career services for current and aspiring sports industry pros. Prior to that he was the Vice President of Ticket Sales and Service for the Phoenix Suns. The company mission is to help people succeed in sports business. To learn more about SBS visit www.sportsbusiness.solutions and follow along on social. T: https://twitter.com/SportsBizSol IG: https://www.instagram.com/SportsBizSol/