Ask More Questions: A curious person’s guide to learning and connecting across an organization

For anyone managing recruiting and talent at your organization

September 29, 2019
Have you ever walked away from a conversation feeling compelled to start something new? Has a good discussion ever re-inspired you to pursue a goal? Or has a single interaction filled you with the confidence to change course completely? We’re willing to bet that someone asked you a few really good questions.

Questions are core to the Job Portraits DNA. As writers, former journalists, and all-around curious people, we believe in the power of those core-striking, truth-baring inquiries, and we strive to disarm and surprise by asking tough questions of each other, of our clients, and of ourselves.

We kick off client engagement with interviews, a workshop, and a slew of video calls because we want to gather as much information as we can. Through our work with growing teams, we’ve seen the power of a strong interview to reveal a new hiring strategy or to discover patterns and language that become a team’s hiring credo. In client work, our questions provide value because we’re outsiders. We bring an unbiased, objective view, and the questions we ask help clients solve tricky challenges.

We wrote this guide for anyone managing recruiting and talent at your organization. Organized into sections based on topics you may wonder about, our intention is to provide you with a starting point for gathering wisdom from different teams at your organization, all with the goal of helping you do your job effectively.

How to use this guide:
  • To discover best practices at your organization that can improve your talent practice
  • To connect with colleagues and share more about your recruiting and talent goals
  • To make friends with other departments and teams
  • To become more curious at work, and in life
Sometimes asking questions means admitting what you don’t know, and that requires a level of confidence and vulnerability that we’ve all been trained to avoid, especially at work. We hope the approaches outlined below inspire you to ask more, thoughtful questions that lead to insightful answers.

You ask: How can I turn rejected candidates into advocates, instead of Glassdoor haters?

Who to approach:
Sales team

How they can help:
Like recruiting, sales is a healthy mix of outbound communication, fielding inbound inquiries, and closing. Sales teams curate the experience a prospective lead has with the company, ensuring a good impression at every single touchpoint. Some best practices from closing deals and maintaining a pipeline may translate to candidate management, and sales wizards could learn a thing or two from recruiters, too.

Questions to ask:
  • Which questions do you ask in early conversations to understand what a prospect needs?
  • Which tools do you use to track sales leads? Could those tools work for recruiting?
  • How do you ensure a seamless experience for a potential partner? Which small details make the most impact? What tricks do you use to ensure a good first impression?
  • How do you respond to rejections?
  • Which moments in the sales funnel best define your impression on prospects?
In practice: A rejected candidate for one role this year could be a perfect fit for a different role later on. Small touches like timely followup and clear communication (where appropriate and legal) can make all the difference in a candidate’s impression of the company. And in a world where word of mouth and online reviews define a company’s reputation, rejections should feel more like conversations than breakups.

You ask: How can I attract higher-quality candidates who also add to our culture?

Who to approach:
Marketing or user research team

How they can help:
Marketers tailor stories and messages to very specific audiences based on what they actually care about. They can give you tips for getting to know your audiences and best practices for speaking in ways that appeal to actual people.

Questions to ask:
  • How do you identify and define audiences for marketing? Which tools do you use to capture and share this knowledge?
  • What should I watch out for when defining these audiences?
  • How many different audiences do you typically target? Why?
  • How do you know when a message is working? How do you test multiple messages at once?
In practice: A candidate will be most successful if they connect with the mission and values of a company AND work well with their actual team. Define the types of candidates you want to attract. Ask recent hires about the way their teams work—from the day-to-day to their mindsets and working styles. Gather real examples to share with candidates.

Try building personas or profiles of candidates, and don’t worry if they feel very different from each other, or if they don’t seem to follow a certain pattern across the company. Then personalize your messages—write blog posts, tailored job descriptions, and social media posts that speak to each persona. Job Portraits can help with this, too!

Watch out:
Be aware of unconscious biases that you may bring to this exercise. Focus on identifying important parts of the roles, skills, and experiences a candidate brings, but avoid defining demographics, age, or gender. Be open-minded. Unexpected candidates may break the mold and still complement a dynamic team—be ready to throw your rule book out the window in favor of someone awesome.

You ask: My team is under immense pressure to hire, but we’re under-resourced. How can we drive results quickly?

Who to approach:
Engineering or product team

How they can help:
These teams tend to manage their work around high-speed results, fast learning, and constant iterations. Tap them for effective strategies for testing out your theories, deciding when to change tactics, or managing an all hands on deck “sprint” scenario.

Questions to ask:
  • Tell me about your current product goals. How do you manage and prioritize them? Show me.
  • How do you define roles and responsibilities on your team? How do you hold people accountable to those roles?
  • Could you tell me about a time when a challenge took longer than expected? How did you reprioritize and maintain team morale? How do you decide when to change approaches or admit defeat?
  • How do you structure your busiest weeks and how do you build in time for breaks?
  • How do you celebrate big wins (and small wins, too)?
In practice: Auditing your recruiting process will help you remove the fluff and improve your most effective practices. This is a win-win for you and candidates and can help improve the experience on both sides.

You ask: How can I tell stories that stand out AND appeal to our candidates?

Who to approach:
Your resident content writer, communications, or PR person

How they can help:
This person or team is constantly pulling stories out of unlikely places, pitching stories to journalists, or translating complex ideas into clearer language. They spend all day every day thinking about good stories, and they’re always looking for new ones. They can help you identify compelling stories about talent at your organization, and they can help you decide how and where to tell them.

Questions to ask:
  • What makes a good story? And how do you think about storytelling for our company?
  • What stories about culture and teams are overdone?  
  • Which blogs, pages, or social media channels do you use for storytelling, and how should I tailor stories or posts to fit into various channels?
  • What kind of stories are you looking for? What is the most effective way for me to share my story ideas with you?
  • I’m most excited about a certain special fact or anecdote, how can I share it with others?
In practice: Consider your reader. Candidates crave authentic information about what it’s like to work at your company, they’re wary consumers of information and very skeptical of being sold to. If you can nail your storytelling strategy, it will be yet another way that your talent practice stands out from the rest!

Never stop asking why. The curious among us are the ones who get to the root of the problem. When you surprise your colleagues by asking them questions that make them think, you’ll both leave the conversation with value you can use.

So get out there and set some coffee dates. Stay open to the lessons around you, and enjoy the conversation. Remember that you have wisdom to share, too. It won’t be long before you’re doing more question-answering than asking.

I owe a special thank you to
Becca Pratt for all her help in bringing this guide to life.

If you're curious, here's a bit about me:
As the resident "Account Manager" (and whatever else comes onto my plate) at Job Portraits, I'm grateful for the opportunity to bring curiosity to conversations with prospective, past, and current clients. If I had my wish I would spend all day every day connecting with new people, and I've never asked and answered so many thoughtful questions until I joined our team. Have a question about this guide or want Job Portraits to ask you some tricky questions to help grow your talent practice? Let’s talk. Reach out at

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