Embrace the Opportunistic Open-Ended Conversation

It’s my job to have a lot of open-ended, serendipitous conversations. I’m continually reminded of the value of these conversations and relationships as time passes. The opportunistic, open-ended conversation could be one of the highest ROI conversations you’ll have, whether you’re a leader or looking out for your own career.

CEOs/Founders/Leaders should block time and invest in open-ended conversations because:

  • Talent meets opportunity–hiring plans are imperfect at best and job descriptions are too often poorly written marketing materials. An actual conversation can be illuminating! You’ll discover someone’s interests, motivations and skills without the false, contrived constraints of an interview process. You just might discover that someone with a very different title has just what you need. 
  • Time passes quickly, you’ll benefit from a longer-term lens–these conversations might not lead to a hire right now, but 3, 6, or 15 months from now, things will be very different–at the company and probably for that person. This foundation enables you to reach out or recruit with context and history rather than a link to a role hoping they’ll be open to a targeted conversation.
  • Representation doesn’t happen just because you want it to–show your commitment to building a diverse team by intentionally and proactively investing in relationships beyond your existing network. When it’s time to hire, you’ll have authentic connections rather than the need or desire to fill a specific open position with someone who is not: [white, male, from the same university, etc].

Individuals should respond or reach out to have opportunistic conversations because:

  • It’s about options–now and later. This is the flip side of what I put above. You never know where your career journey will take you, or if you’ll encounter unexpected starts and stops. Building your network means you have a long-term lens on your own career and relationships that serve as a starting point when it’s time for a change.
  • It’s about the team–so much of what makes a great job is about the people you work with. In fact many people would choose a team over a product, role, or stage. Why hope that that job posting has the right team associated with it when you can meet a lot of people and start from there?
  • You want to be ready when the right opportunity emerges even if it isn’t “this one.” You’ll learn more about yourself, what you want and how you could contribute to different roles and teams through this exploration, increasing the odds that when something “feels” right, it actually is.