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Hey Bosses! Heard of Cuffing Season?

You are always developing your rising star leaders. The question is whether you get to keep your investment or not.


If you have rising stars and you are not intentionally developing them, having regular 1:1’s and mentoring to support them in their growth, casting vision for the future and crafting space in the organization for them to stay and grow into but also WITH the organization, you are going to lose your investment. 





There will come a point when they are ready for the next level. You should have found out what direction they want to grow toward right from the beginning and begin studying them to see if they are the right fit for the organization to grow with. And when they are ready for the next level you will either have space for them or they will take the experience they acquired to the next organization that has the next level ready for them. All the training and hard work you put into them as a leader; those skills and focus and creativity? They gone bro. And then you will have to start all over again (especially if you don’t have a budget for seasoned leaders that come ready with all the experience and knowledge so they can hit the ground running). 


You will have to do the onboarding, go through the phases of team dynamics (forming, storming, norming, performing) and make sure everyone is fitting well together. It will be about $5000 on the low end once it’s all said and done to hire, and more for you to train the new hire for the first year. And if the new hire is also an ambitious person that you are not prepared to keep, the cycle will start again soon. 





So! You want to date to marry rather than do serial hookups.Good news! It’s cuffing season. 





Don’t know what that means? Get ready for a slew of irreverent analogies that will be all over the place. For over a decade I keep saying that romantic relationships and professional relationships are basically the same. But with one you get butterflies and feelings and with the other you get money. Sometimes you get a vice versa and sometimes you get both in each scenario. But the same patterns that happen in the dating world can be seen in the professional world.


Let’s start with what the kids these days call CUFFIN’ SZN. 

This is the season when the single people want to pin down someone to snuggle with during the cold months. Usually, or ideally, it would go like this: 

summer fun fling > cuffing season > what are we? > will you be my valentine? > yes, ok now we’re in a relationship > queue the relationship escalator. And happily ever after or something. 


Cuffin season technically starts around September-October and surprise surprise! The peak hiring season is September and again in February. Which is, surprise surprise! The end of cuffing season. 


Are you starting to sense a pattern here? 


In the professional realm, you would ideally have a badass strategic business plan because that is imperative to the health of your business (and a different blog post coming) (hire us for that by the way. We do an incredible job that will take you through breakthroughs and aha! moments and get you unstuck. We help you break the growth ceiling you’ve hit. Or we help you get your ish together if you're a hot mess. We are like super good at it and I am not even exaggerating). Anyway, where was I? …ah yes, and then you have either an opening for a job or a short term contract available or even a full position. This is your starting point. So you begin the dating process. You got the coffee dates and this is the first interview where you talk about priorities and what do you want? Here is what I want. What do you do for fun? Are we a good culture fit? Yes we are! Okay! Now the second interview.


Because you know the growth trajectory that you are taking your organization in, you know the seats that will be opening up in the future and you already have your eyes open for the right people. And because you’ve worked with us you have mastered hiring the perfect culture fit candidate. So you make the offer! And then you cuff. You’ve pinned down your person to accomplish the big ol’ project or function that you’ve been needing help with.





The first three months are all about getting to know each other. Did you know it takes people three months to figure out if they want to be with a person long term or not? People know. The relationship that ensues after three months (around the end of cuffing season) is simply to confirm what they have already decided and develop a common ground to negotiate priorities. Well, same thing at work. The first three months you are gauging how good of a fit you are for each other. Are you more into them than they are into you? Could you see them growing with the team? Do they have what the company needs beyond their tactical skillset to get the job done? You are checking each other out and trying to figure out if you want to make it serious. 


So you went on a coffee date, then you went to dinner, then you decided to cuff, and now you’re figuring out if you are going further than cuffing season. And omg they are amazing! Of course you picked well because you prepared for this! And you want to make it official official. You want to take the next step and get serious. You see them growing with the company and they see themselves growing with the company. They fit well with the team and contribute amazing value and it’s upward spirals everywhere.




You immediately can see they are a rockstar and that with intentional leadership development they can be the right person for some critical seats in the company. So you begin to intentionally develop them because you know that for every dollar you invest the ROI is seven. SEVEN! 



And then the day comes. You are going to get married. They are going to make partner in your firm. Or they are going to be your next director. They have everything they need to be the executive director. And because they’ve invested some time with the organization they have a pulse on the needs of everyone and they know how the culture works and they know how to shift together and how to keep everyone rowing together. It’s beautiful. 


You take the plunge and your organization is thriving like never before. They attract top talent because they know how to be a leader others want to follow. Your organization just keeps growing and getting stronger. You feel super solid and zero percent worried about succession because you’ve nurtured the right people for the right seats and you have a strong culture, a solid growth plan, you have the creativity to tackle any challenge that comes your way. You are at peace.


How amazing would that be?





In reality though, what happens most often, in the dating world and the professional realm, is that people get as far as cuffing season and they can’t make it past it. They break up for little reasons. Small stuff that could have been navigated properly and turned into deeper commitment, deeper connection, expanded perspective, tends to be the end of the relationship. There is destabilization, having to wrangle together the pieces that are left floating around after a person has been in your life or your team for a little while.


 And the cycle starts all over again.


Get over the destabilizing phase. Begin the search again. Summer is here and it’s time to have fun which hopefully will be a fling, and cuffing season, and what are we? Part ways again. 


Your employees take all the training and experience and use the time they spent with you as a stepping stool to get to the next level. But you could have been their next level. Even if the seats were not ready, a very intentional ongoing conversation about their professional growth could have given you a creative solution that was mutually beneficial. 


It’s time to approach this differently. 

It’s time to do it with intention.

It’s time for you to go steady instead of being the stepping stool.

It’s time for you to keep your investment after you train every new hire. 


We have something on the DL for your emerging leaders. It’s kind of hush hush right now because we haven’t announced it to the world officially yet. It doesn’t even have a name yet, that’s how early you’re hearing about. 


I want to help you develop your leaders and deepen them to be ready to grow with you. Leaders set the tone. And if you make a point of getting your rising leadership on the same page, heart beating the same, unifying them under the values of your organization, watch how they will rally the rest of your team members and help them all row in the same direction. This is where big stuff happens. This is how you break to the ceiling and your competition sees you as a real threat. This is how you make your most ambitious goals happen. 





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