How to build a personal board of advisers

July 29, 2021, 12:00 PM UTC

Q: As an entrepreneur and the face of my company, I’m the one people look to for answers about what we’re doing and how we should solve every problem. Honestly, sometimes I just don’t know. I’m so jealous when I hear people talk about tips they get from their mentors and people who are making connections for them. How do I find a mentor at this stage in my career who will understand the work I’m doing?

Dear Cory,  

You’re not the only person I’ve heard from with years of experience who wants a mentor but is totally mystified about how to connect with one. Conversations around mentoring often focus on supporting people in the early stages of their career, but everyone needs support navigating their work life. 

Mentor relationships can be bountiful sources of inspiration and support, whether you’re the mentor or the mentee. These relationships, like other relationships, can feel truly magical when there is a strong connection between the people in the relationship. To find and foster that kind of connection, you need to be intentional about what you’re looking for and reach out to someone who understands and values what you’re building right now. Don’t choose someone simply because of their status, because other people want you to be in a relationship with that person, or because it seems like what someone like you should do. Your mentor should be someone who can give you advice on specific matters you’re dealing with and perspective on the world that you’re operating in. 

Along with investing some time into your search for a mentor, you should also think about building out your broader support network at the same time. You need spaces where you feel understood, and there are ways you can find that validation and get inspiration without a formal mentorship. You can draw a parallel, if you like, to romantic relationships. Even if you have an incredible primary partner that gives you a ton of what you need, most people also need friends and family to fill in with other needs. 

Before you start asking for help, it’s helpful to take stock of what you need and how you want people to support you. Let’s unpack some of the words that people sometimes throw around when it comes to mentors and related relationships. 

A mentor will be someone that you have an ongoing relationship with who can offer you guidance. A sponsor is someone who will use their social capital for you to open doors for you. Your support network is the group of people who you turn to for support and advice on different matters, which can include colleagues, friends, therapists, mentors, whoever you turn to for guidance. 

Some people like to get really intentional about the different types of guidance they need and even identify their own personal board of advisors (or personal board of directors). 

To me, “personal board of advisors” seems like a formalized version of what we all need to do: talk to many people and get numerous perspectives. Thinking about the overall group of people you turn to for support might help you identify gaps in your own skill set and perspectives that would help you understand aspects of your business that you’re not as strong on. 

Here are some questions that might help you identify what you’re looking for right now: 

  • Are you looking for technical help and guidance on what you’re building?
  • Do you need someone to bounce ideas off of before running them by other people?
  • Do you want someone in your industry or another industry who can make connections for you and open doors to funding, new clients, or opportunities? 
  • Do you need to process some of the things happening at work or vent to someone who understands what you’re going through? 

Since I’m interested in helping you think about both finding a mentor and building out more of an overall support network, I spoke to Beth Pickens, a creative consultant who helps artists move their lives, careers and practices in the direction they want. I think entrepreneurs and artists have a lot in common. Both groups are driven by their own vision and motivated to create new things. 

In Beth’s book Make Your Art No Matter What: Moving Beyond Creative Hurdles, published earlier this year, Beth offers advice to creatives for overcoming roadblocks and navigating their careers. She specifically points to mentorship and building community as key to helping artists succeed in pursuing their creative vision, helping combat isolation and ambiguity through inspiration and fellowship.

Our culture encourages us to pretend we know what we’re doing. Everyone’s just kind of pretending they know what’s going on and not asking questions. A mentor is somebody that you can actually ask questions to and not feel like you’re compromising your professional reputation, that you can bring the questions you think are scary or overwhelming or dumb or too personal or too specific,” Beth told me. “You can talk about things that maybe you wouldn’t feel comfortable talking about with a peer, or with your supervisor, or somebody you’re working with.”

As you think about who to reach out to for mentorship or to be a part of your personal board of advisors, think about who is in your network already that can help you that you’d like to build a deeper relationship with. Beth recommends reaching out to someone who has built a life you admire.  

“Look at somebody who has what you want, not just the job, but how are they living. Are they satisfied in their lives across a number of criteria? Not just job title, not just financial (but those included), but somebody who kind of has what you want some day,” she said. “It requires being in community, participating in community so that you know more and more people outside of your own circles. I certainly think you can look to who is in your professional field, whose contributions you really value, and, if that person isn’t available, then who are people that are in their professional orbit?” 

If you really like someone’s approach but they’re not available, look to their collaborators or ask them for recommendations of other people they’re in community with that you might be able to connect with.  

Once you decide on someone that you’d like to ask for advice—either in a formal relationship or as a more informal part of your support network—reach out to them and ask them to work with you. Please don’t do what I did many years ago at a conference, when I blurted out “Would you be my mentor?” in a five minute hallway conversation with a legendary woman in journalism. I’d been acquainted with her for a year and had followed her recent transition to a new job, which was in line with where I wanted my career to go. After she enthusiastically said yes, I made no follow up that week or in the months to come, which was a total waste of an opportunity for me to grow and learn from her. Give your prospective mentor a clear expectation about what you’re looking for, how they can be helpful, and how you’d like to connect with them going forward. 

You’re also going to have to make yourself available, which means making some space in your life to do the work. It’s better to prioritize the work and proactively make space for it, than to be desperately reaching out to people at the moment you’re in crisis, needing advice immediately.  Block out some time on your calendar to dedicate to working through what you need before you reach out to folks, and accept that you’re going to block out time for a regular commitment that works for you. Depending on what you need, the length and time commitment of the engagement is going to change. 

If you’re starting a new relationship with a mentor, start with an intentional meeting or phone call once a month. It’s not too heavy of a lift for busy people and it will give you a chance to see how the chemistry is. If you hit it off, you can always ask to meet more regularly. When you’re dealing with a tough work situation on deadline, you might need to be in touch with a mentor multiple times in a short time span while you deal with it. For some people on your support team, you might only check in with them once or twice a year. 

While mentors can certainly help us get to the deeper work, it’s also helpful to remember that the time you spent with them shouldn’t just be time for you to vent. If you’re looking for someone to give you space to talk through your issues, you should also consider paying someone. An executive coach or a consultant like Beth can give you coaching on a specific thing you’re working on or give you feedback on your approach. A therapist can validate your experiences, help you process the interpersonal dynamics at work, and give you tools applicable to all of your relationships. You might see an executive coach every other week for a three month period, or for another time frame that works for you. With a therapist, carving out time weekly or biweekly can help you get into deeper work. Investing in these roles on your care team will not only help you by giving you more support, it will also open up space for you to focus on more relevant and tactical issues with your mentor when you get together. 

As you look to new ways to connect with people who can support you in your work, think about ways you can connect with your broader community or with other people in a similar situation. Beth created a homework club where she matches up artists based on their interests and practice areas, and she provides creative prompts each month. In July, the topic was rest, vacation, and time off, and why that’s so hard for artists though so necessary (to me, this is just another example of something artists and entrepreneurs have in common). Together, the groups hold each other accountable to deadlines and cheer each other on as they take on new challenges. You might find a similar network in your industry, connect with entrepreneurs in your city or find an internet group. 

You can also create your own club. Last year, Virgil Abloh, CEO of Off-White and artistic director of Louis Vuitton men’s wear, created Free-Game, which he describes as “an attempt to provide a mass form of mentorship.” The site pulls together over two dozen videos and more resources for people building a brand.  Not only will this website be a wealth of resources for you as an entrepreneur, it’s also a great example of something that you could use as a homework assignment with a small group as you’re building community. 

As you start making more space for reflection in your work life, you might find that what you need isn’t so much the answers to the questions that you’re getting from your team, but that it’s a space process the challenges you’re dealing with and feel understood. As you invest more time in your professional development, your relationships with mentors and your peers, you’ll find that you’re also part of a broader community of people who understand what you’re doing and want to help you succeed.  

“Community is everything. I think no matter your sector, you really need community for all the different parts of your life including your professional and creative life,” Beth said. “In a group of peers, there is so much wisdom. Any group of four or five people probably has all the answers because everybody has different experiences, and the wisdom that comes together in any group is more than any individual has.” 

Sending you lots of good vibes,

Work Space is a monthly Q&A column tackling the work challenges that keep you up at night. You can read all columns here. If you want advice on something you’re navigating at work, send your questions to