Rather than a one-sided interviewing dynamic, working relationships could start with an open exchange of perspectives and personalities.

We’ve all been there—that nagging feeling of uncertainty when starting to work with a new boss. Will we click? What are their expectations? How will they want things done? What does this change mean for me? The doubts can be overwhelming and distracting, even for experienced professionals.

During a recent coaching session, my client admitted he was struggling to focus because of worries about his new manager. “What will she be like? How will we get along? What are her priorities?” he fretted. A major project he had poured efforts into was mid-stream—would she want to change course?

When I suggested he be upfront and ask her some questions to get to know her better, he balked. “Can I be that direct? Isn’t that rude or nosy?” We both chuckled at the idea of a professional workplace feeling like an awkward dating situation.

But that’s often how we approach new working relationships: walking on eggshells, making assumptions, letting doubts fester instead of clearing the air early on. We instinctively hold back parts of ourselves until the other person has earned our trust over time.

What if we flipped the script? Rather than a one-sided interviewing dynamic, working relationships could start with an open exchange of perspectives and personalities. An upfront discussion of communication styles, motivations, and quirks. A chance to put our authentic selves on the table, understand what makes each other tick, and start establishing psychological safety.

Sure, it may feel a bit vulnerable at first. But laying those foundations early creates a path toward teamwork, empathy, and efficiency much sooner. No walking on eggshells required.

Some potential get-to-know-you questions to consider:

  • What situations bring out your best/worst?
  • What are your strengths/non-strengths? (I don’t call them weaknesses…no one is good at everything; we all have natural strengths and non-strengths. That term takes the negative connotation out of it.)
  • How would you describe your leadership/work style?
  • What are your core values?
  • What keeps you motivated and engaged?
  • What are some quirks or pet peeves of yours?
  • How would you prefer we structure our 1-on-1 meetings? How often to have them?
  • What are your communication preferences? When I need to reach you, do you prefer a call or a text?

My client was thrilled to report on our next call that he had met his new boss and they had this meeting in her first week. He was excited to share all they have in common and she was enthusiastic about continuing progress on his big initiative. She offered to support it and help champion it too.

This onboarding practice can be used with a new direct report, or a new peer that you will work closely with, a new client, or a new vendor. The questions can be tweaked to make sense given the type of work relationship.

An initial investment of open dialogue pays dividends down the road versus months of doubt, misunderstanding and walking on eggshells. Wait too long to have the conversation, and patterns (some potentially unhelpful) may already be set. So don’t be shy about asking—or answering—those insightful questions right off the bat. Your future working relationship will thank you.

Michelle Sanford

Michelle Sanford

Executive Leadership Consultant

Michelle Sanford is a certified executive coach who has spent her career working with senior leaders and their teams to reach peak performance in both their professional and personal lives. With over 25 years of corporate experience, Michelle has held a variety of leadership roles and industries, working in sales, marketing, product development, operations and management. She built her operations and innovation expertise as an Innovation Analyst and an Operations Director before taking a role as the Director of Product Marketing. For the past two decades, Michelle has leveraged her organizational and management knowledge to help CEO’s and executives across the United States, to help them achieve maximum results and sustain life-changing behaviors.

Learn more about Michelle here.

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