Blog / Advice / Tinder for Jobs: How to have a great career conversation about job happiness with direct reports

Tinder for Jobs: How to have a great career conversation about job happiness with direct reports

In this new age of information overload, passive job searching has become as frictionless as swiping on dating apps. “Job looks decent enough, sure, swipe right. Oh, I matched! Gotta go text my boss and let them know today is my last day.”

This is a far cry from the high-effort job searching of the past — preparing for job fairs, combing through newspaper help wanted ads. That friction made job searching a herculean effort. Now? Most of your employees have probably visited a job search website in the past 24 hours. Probably from the company internet. Probably nothing serious, but it’s so easy, why wouldn’t they?

Here’s the thing: you need to be transparent about job searching. You should be acting as a steward of your employee’s career, not just a passive participant. Embrace it. Encourage it.

The Power of Honest Career Conversations

This leads me to one of my favorite types of 1:1 meetings I used to have when managing the sales team at BrightGauge. I’d ask participants to bring me the job they wanted to work towards from outside the company. I essentially asked them to job search.

In our meeting, we would review what they brought back and have an honest discussion: How likely would they qualify for the job? What were the compensation numbers? Were there any cons? Basically, we’d job search as a team for them. From there, we’d map out the skills they needed, what they had to work on, and where they truly stood based on their current compensation.

This provided a great forum for open and honest communication about everything from job roles to compensation — without keeping either party guessing about the status of our working relationship.

I can honestly say that everyone who participated in this process said it was one of the best meetings the company would run. The feedback was incredible. It built trust, created clarity, and ultimately made people want to stay and grow with us.

EOS® Tools That Support Transparent Career Development

Running these kinds of conversations becomes much easier when you have the right framework and tools. This is where EOS® principles really shine — particularly around accountability and people management.

The Accountability Chart™ helps employees see exactly where they fit in the organization and what advancement opportunities exist. When someone brings you that external job posting, you can reference your Accountability Chart to show them potential growth paths within your company.

The People Analyzer™ gives you objective criteria to discuss someone’s fit in their current role and what they’d need to develop for their next role. Instead of vague feedback, you can point to specific areas like whether they “get it, want it, and have the capacity” for different positions with the People Analyzer™.

Regular 1:1 meetings create the perfect venue for these career conversations. When you’re already meeting consistently, adding career development becomes natural, not awkward.

Making Career Development Part of Your Operating System

At Strety, we’ve built tools specifically to support this kind of people-first approach to management alongside our EOS software. Since we’re operators ourselves, we know how crucial it is to keep great people engaged and growing.

Our platform includes:

Automated 1:1s — Use customizable templates available in-app or create your own 1:1 agendas. You’ll see greatly improved consistency and engagement with 1:1s when they’re built into the system your team uses every day.

Performance Reviews — You see the metrics every week in your Scorecard, but it’s important to step back and address larger trends in employee performance. What’s going right or wrong? How can they get on track towards the career of their dreams while driving business growth?

360 Reviews — Turn the tables on reviews! Just like providing employee feedback is critical to their growth, getting feedback from your employees is crucial to helping you create a better business. These reviews have the power to transform your organization.

The Bottom Line: Transparency Builds Trust

When you encourage job searching and career conversations, you’re not opening the floodgates for departures. You’re building a culture of transparency and growth that actually makes people want to stay.

Your people are the foundation of your business — help them rise to the occasion through honest conversations about their future. Otherwise, you could be getting blindsided when their next tempting offer comes along.

Think it through. Try it out with someone you’ve been meaning to get more clarity from. You might surprise them, and yourself.

Want to see how Strety’s people management tools can help you build stronger relationships with your team? Start your free trial or book time with our team to learn more.

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