10 Ways to Become a C-Sweet Dater

Be the Chief of Your Love Life

First, what is the C-Suite?

(I’ve renamed it C-Sweet because relationships should never be sour or be entrapped by four walls.)

In corporate life, the executive team is referred to as the C-Suite. You can nerd out on the official definition here.

It basically means that the people “at the top” are ultimately responsible for making data-based decisions that lead to (hopefully) positive outcomes.

The most successful C-level execs make tough calls, act relatively quickly, and worry more about being respected than being popular at all times. (I was a CMO in a past career life BTW.)

I was inspired to write this article by a man named Jim McGrew. I (ironically) connected with him on a dating app.

I don’t meet his “criteria” (see #2), but we’ve both been single a long time and were talking about how applying some of the skills we used in business to our dating lives might ultimately make us more successful in love and relationships.

Yeah, that’s why dating often feels like a job.

But perhaps that’s not totally a bad thing.

Taking a page from a leadership handbook, here are my 10 basic principles of relationship-seeking.

You can even give yourself the title of CDO (Chief Dating Officer) if it makes you feel more important! And, like any good executive in the C-suite, listen to other people whose opinions you value and who may give you new, intelligent, and insightful perspectives.

1. Set your objectives—long-term and short-term. Are you looking for fun activities for Saturday nights or a true life partner? Your goals may change over time, but be clear about them.

2. Establish your “talent” criteria and job description. For example, I have a list of factors that are important to me. Some are more critical than others. The aforementioned Jim has a 30-mile radius limit. (One of my podcast episodes dealt with long-distance dating.) But distance is not the only factor. Things like a sense of humor, types of activities you want to enjoy with a partner, and family status all fall into play.

3. Build your corner office and calendar. The amount of time and energy you devote to dating depends on what else you’re doing with your life. Your “corner office” is your safe personal space. Set boundaries and sometimes keep the door locked. See #9.

4. Create a “ talent recruitment” plan. Are you planning on going down the rabbit hole of online dating? Amping up your real-life activities like MeetUp groups and cultural and athletic gatherings? Investing in a professional matchmaker (the equivalent of an executive recruiter)? Leaving it up to the universe and/or introductions from friends and family? Some combination?

5. Craft good “interview” questions. Listen to the answers.  Really listen. Don’t get too personal too quickly, but watch out for pink flags or answers that don’t match your #2 factors.

6. Establish a 90-day probation period. Just as employees and employers usually have 90 days to decide if a working relationship is the right “fit,” so can daters. Listen to this episode on some of the things we may miss when we’re eager to find out “person.”

7. Don't jerk around or mislead your backup candidates. People dating multiple people will often “bench” or “ghost” people they aren’t sure about. We’ve all been in a similar situation work-wise. You had an interview that you thought went well, but then you got sporadic or protracted follow-ups or no communication at all. Be kind to those people who you’re not interested in and just “send that rejection letter” as soon as you know they aren’t the right person for you.

8. Provide feedback and pay attention to how it's received. No relationship is perfect. But how your significant other takes criticism is really important (unless you thrive on being dismissed or treated poorly). As things progress with your top choice, let them know behaviors that give you pause and pay attention to whether they get defensive or angry or shut down. Imagine you’re giving an employee a performance review or talking honestly to an office teammate. They don’t agree with what you said. Would you tolerate their yelling at you or shutting down your ZOOM call? Expect the same in your dating life (and practice giving feedback in a kind and caring way). And, of course, Bumble isn’t Indeed, but some of these tips are helpful in all aspects of life.

9. Don't let just anyone into your corner office. Yup, I’m talking in part about sex here. However, it also applies to basic boundaries in relationships. Trust is key and takes time to build.

10. Fire quickly and compassionately if the fit isn't right. Most people don’t like hurting or disappointing others, but your time and energy have value, too.

As we’ve established in past articles, I’m a romantic, and my heart and gut sometimes get in the way of my brain.

If these 10 steps were all we needed, we’d all be titans of the dating ecosystem and would be madly in love with the right person.

Finding that person is much more complex than finding someone to create spreadsheets or build marketing funnels, but some of the same principles apply.

Think like a leader rather than a victim. You may not get a 6-figure bonus at the end of the year. But you may wind up with something even better!