OG Tuesday Issue #200

💼 Entrepreneurship: Overrated business advice. Feel free to ignore.

🎯 Job Search: Fall short of the job’s reqs? Ace the interview anyway.

❤️ Feel Good: Altruism lives! Corporate volunteering is on the rise.

🗣️ Communication: The lesson one career coach wishes she’d learned earlier in her own career.

⚖️ Work/Life: Nearly half of workers would choose better work-life balance over a higher salary.

There’s no getting around it, although it may seem eye-rolling-ly obvious: The most effective and efficient way to create a sharing-friendly workplace is asking your colleagues and direct reports to share.

What’s far less obvious is how to do the asking well—in a way that truly encourages thoughtful answers. Keep reading to be illuminated.

Ask only open-ended questions.

• Open: What did you like about XYZ?
• Closed: Did you like XYZ?

On paper, the closed question seems to be begging for complete conversational atrophy. While hearing a “no” might feel briefly more awkward, a “yes” can kill a conversation just as fast.

And yet…we ask these questions all the time in real life, when we’re too busy interacting to think about the conversational risk factors of every question.

Try being just a little bit more mindful of how you’re framing questions. You may be startled to hear so many closed questions popping out of your mouth.

Don’t worry. The goal is working gradually toward a level of awareness where you automatically edit questions before asking them.

Ask precisely what you want to know about.

We’ve probably all felt the consequences of hearing a question—a command, really—almost too impossibly vague or broad to answer…you know, probably during a job interview or a hundred.

“Tell me about yourself.”

Many recruiters would argue they use this broad request to learn what the candidate wants them to know about themselves. Fair.

But nevertheless, the purpose of this little exercise is simply remembering what it feels like in your head when someone asks a vague question.

It can feel uncertain, disorienting, and completely befuddling. You have permission to answer in any way you can imagine, and yet…you can’t imagine a single answer.

You can’t separate it from all the other ideas that fill your head when you hear broad terminology. Yourself.

If the goal is encouraging people to share, then make it easier and more enjoyable for them to do so. Simply ask them exactly what you want to know. (It might even help to ask yourself that as you’re formulating questions: What do I really want to know?)

For example, imagine you’ve just completed a group interview and finally have a few moments alone with a colleague you’d like to get to know better.

What did you think about Candidate X?

What did you think about how Candidate X doesn’t have the minimum experience “technically” required for this position?

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One TA Subscriber yearns to assimilate into their new team and new role:

My biggest challenge is finding my feet as manager within an already established team. I have been in my new job for a few weeks and while everyone is welcoming, I’m finding myself feeling out of my depth.

Being the “newbie” almost always feels awkward, even when you’re the boss and even when your new team is great.

No matter how far up on the education or career ladder you’ve climbed, you can start a new role, and poof—feel temporarily back at square one.

“Temporarily” is the all-important word here and your silver lining, dear subscriber: Being the “new one” never lasts forever.

• Sure, it feels like everyone else on the team knows each other better than you know any of them. For now.
• Sure, everyone might know more than you do about how the organization works. For now.
• Sure, you’re learning a lot right now and feeling a little uncertain. For now.

This phase will pass. (Even the most skilled and repeat “newbies” can’t hold the crown forever.)

While it passes on its own, there are—of course—ways you can try speeding up the path to comfort and familiarity.

One general rule of thumb: People first, work second. Prioritize making human connections before getting into the weeds of the work.

Fast-track strategy 1: Ask the people on the team what they need and/or what they need from you.

• How can I support you?
• What is your biggest challenge?
• What part of your work do you love doing the most?
• How can I be a better manager to you?
• What were some of your last manager’s biggest strengths and weaknesses?

Asking any of these or similar questions might just get you the feedback you need to feel more aligned with your team. Even better, asking helps build trust by encouraging candor and creating a safe and open space for sharing.

Fast-track strategy 2: Talk about the big-picture aspects of the work.

Being the newest member of the team gives you an advantage for this strategy. You have fresh—and inspirational—perspectives and insights.

Best of all, you can effectively contribute to discussions about broad goals and missions without having to understand every convoluted workflow that seems second nature to your team.

As a bonus, you can prioritize learning and thinking about these broader goals to feel empowered while you’re learning all the other stuff.

Fast-track strategy 3: Set your own big-picture stretch goal. (If you haven’t already.)

Ideally, you can find a goal related to something you feel passionately about, something that will spark the creative and exploratory part of your mind.

Keep it to yourself for now, and work on it each time you’re feeling an overwhelming sense of uncertainty about how things are done in your new role.

With hope, working on this project will remind you how capable you are.

Too busy being the new boss to set up a passion project? Heard.

Here’s a shortcut toward getting a little boost of confidence: Reflect on something you accomplished in any of your previous roles and positions. Stoke the feel-good vibes by asking yourself questions to stretch out your restorative recollection.

• • What action or behavior of yours do you think contributed most to your success?
  • What did it feel like when you first realized you’d done it?
  • What aspect are you most proud of?