When I started my current job a year ago, I found myself navigating a brand-new dynamic: For the first time, I would be joining a workplace where one of my colleagues was also a good friend.

Further complicating things: That friend, Charter COO Erin Grau, was the one who had recruited me. To a company she’d co-founded.

We’d been work friends before—we had met while both of us were working at the New York Times and stayed close after moving to other jobs, a coworkers-becoming-friends dynamic that plenty of people are familiar with. But going from real friends back to colleagues felt different: How would it affect the relationship we’d built? For that matter, how would it affect the way our other colleagues saw us—including issues of fairness and favoritism, perceived and real?

Simultaneously navigating new professional and changed personal relationships can be challenging. That’s not to say that scenario is one to avoid. Quite the opposite: Coming into a job with built-in social support can improve your success and boost the likelihood that you’ll stay. “Not having any social connections at work definitely impacts your company loyalty, and also your feeling of enthusiasm and mission for your job,” says Katherine Goldstein, who covers workplace and social equity issues as a journalist and fellow at The Better Life Lab at New America Foundation. And employee research from Gallup demonstrates a strong link between workers with best friends at their workplace and profitability, safety, retention, and other benefits.

This way of working just requires careful planning and communication, according to a half-dozen professionals with relevant experience who I spoke to on the subject. Over and over in these conversations, two themes emerged: the need for deliberate introspection, and the importance of open dialogue. How to put those into action? First, know thyself: Make a user guide to working with you, as your friend. Then share with your friend as a jumping-off point for a deeper conversation about what you both need. Here’s how to go about it.

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Create a user guide for working with me, as my friend

In my recent roles I’ve benefited from writing a user manual for working with me, and have learned from reading my colleagues’. Preparing responses requires self-reflection on the part of the writer and helps orient the reviewing colleague.

A more focused version of this document can be a powerful tool for friends in navigating the transition to colleagues. Spend some time thinking about your work self—how you work, what you need, how that version of you overlaps with and differs from who you are outside of work—and share with your friend your answers to these prompts:

  • Emotional baggage I bring with me from past roles. Organizational or interpersonal experiences that can affect how I show up.
  • How I want my work environment to respond to our friendship. Because some workplaces are more amenable to close social relationships than others, this is what I hope to encounter and foster (for example, support or well-understood boundaries).
  • My top three priorities right now. What I may not have told you about my goals, professionally and personally.
  • How I want to be perceived by others. What I value in how my contributions are seen by colleagues and external professional contacts (partners, vendors, etc.).

Must-discuss questions for your friend-slash-colleague

Goldstein shared some guidance in her writing on making and keeping adult friendships that is relevant in work settings, too: “Vulnerability builds relationships.” We want to be trusted, yet many of us want to limit our vulnerability at work.

Making an existing friend-slash colleague-slash-friend relationship work, though, requires an extra level of vulnerability. To help work through your self-protective instincts, I share another set of questions for you and your friend to talk through live.

I suggest talking about your user guides first as they’re a useful precursor, but don’t let sequence prevent you from raising these questions, at the start of your relationship as colleagues and on an ongoing basis.

Inclusion and belonging

  • What do you admire about other workplace friendships/relationships you’ve observed? What aggravates you about them, if anything?
  • What behavior do you think our friendship models to others?
  • Who do we exclude because of our familiarity with each other? How can we be proactive about bringing them along?
  • Does our friendship limit your openness to connecting to other coworkers?
  • How can our relationship bring about good for more people? (e.g., suggested volunteer activities for staff around a cause we both support, joint efforts towards workplace belonging)
  • In what other relationships can we each seek out:
    • Feelings of familiarity and kinship?
    • Openness and fun?
    • Recognition from others who know our strengths and want to see us be successful?
  • Feelings of familiarity and kinship?
  • Openness and fun?
  • Recognition from others who know our strengths and want to see us be successful?


  • How does our relationship affect your workplace boundaries more broadly?
  • For the sake of professionalism and confidentiality, what should we each expect about visibility into leadership considerations across our disciplines/roles?
  • How does the organizational reporting structure, including performance management, affect our friendship?
  • What is our sense of responsibility for our shared livelihoods?
  • What is your propensity for difficult and/or brave conversations at work?
  • Can we commit to saying what we need to share with each other, not letting it fester for weeks or longer?


  • What should we do when we’ve been spending too much time together?
  • What happens if one of us:
    • Is promoted?
    • Starts managing the other?
    • Is let go from our organization?
    • Chooses to leave for any reason?
  • What circumstances might contribute to us no longer being friends?
  • Is promoted?
  • Starts managing the other?
  • Is let go from our organization?
  • Chooses to leave for any reason?

Add your own questions, too. It’s uncomfortable to get into the bits about power, tenure, influence, and unspoken expectations, but I urge you to embrace the awkwardness. Having a shared understanding will ultimately leave you both feeling prepared to make both parts of your relationship thrive.

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