When I was in my twenties, I worked for a finance company. I was the most junior person on the team that kept our computers and servers with complete precision. As Sunday night rolled around, I began dreading the week ahead, slogging through painful meetings in a role that just wasn’t a “right fit.” This was not the case when I started my first company, shortly after that. I noticed that while I was prepping for the week Sunday evening, I wasn’t dreading the next five days. This is where it kind of clicked for me and I gave a name to what I call the Sunday Night Test.
The Sunday Night Test is simple: are you dreading the week ahead in your job? If so, then it’s time to embrace a brass tacks analysis of the source of that dread and figure out whether it may be time to make a change. You can apply it to yourself as an employee. But now as a company founder, rather than just apply the test to myself, I encourage my fellow team members to apply the test themselves. If you are a leader or a manager, it’s incredibly important to know whether your teams are passing or failing the Sunday Night Test.
I like the Sunday Night Test because it spans age groups. It’s highly subjective and qualitative, but that’s sort of the point. What it’s supposed to do is not just have the person think, ‘Oh I don’t want to go to work tomorrow’, but if that’s the case, let me think about the things I can do to not dread going to work tomorrow.
I’m not (entirely) delusional. Workdays typically can’t compete with weekends. This noted, I lay the groundwork early for open dialogue and tell new employees you should be thinking about this every Sunday night when you’re employed here. If, at any point, you are dreading going to work the next day, let’s make some changes to do things differently.
A culture of candor is key
Importantly, in order for employees to feel that they can tell you their job doesn’t pass the Sunday Night Test, they need to feel that management and the company are open to hearing it. You can help to build this into your culture by walking the walk. Talking about your own mistakes. Share where you’ve struggled and what you’ve learned. But know that you’ve got to build this culture early on. It’s not unlike cooking versus baking. With cooking a steak, you can fine tune flavor, adding a pinch of spices here and there, even throwing it back on the grill a few more minutes, if needed. With baking—much like culture—there’s no adding an egg after the cake comes out of the oven. Be very conscientious of the culture that you’re building and communicate often that it has to be a shared responsibility that we all participate in building. What it feels like to be here, how we communicate, how we problem solve, what our routines are, how we make decisions. All of those pieces of our culture need to get baked in early, and with contributions from the entire team, because the culture gets set early and it is harder to change as you grow.
Identifying the source of the dread
What’s at the core of the dread? Do you not feel supported? Not clear on what success looks like? Not challenged? Not heard? Afraid of making mistakes? Are there inner personal conflicts with people on your team? Are you feeling like there’s a role within the company that you may be better suited for?
Moving forward/proposing solutions
As a manager, I don’t believe that someone on my team has to always have a solution in mind if they identify a problem. Some problems need collaboration and just because a team member doesn’t know how to fix a problem doesn’t mean they can’t identify one. As an alternative, I like to say that with problems come projects. As such, I suggest taking a Socratic approach, stepping back and asking questions to bring you and your employee to what a solution might be and then empowering them to solve the problem. It’s one of the most rewarding things I do in my job and it’s helping my team to pass the Sunday Night Test on a regular basis.
Keith Smith is the cofounder and CEO of Payability, a fintech company that provides financing and payment solutions to e-commerce sellers. Previously, Keith founded and ran multiple startups, including; CyberMortgage, Zango, and BigDoor. Payability was recently listed #97 on the Inc. 5000 and on Inc.com’s list of the 10 hottest companies in New York City.