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When I first started as a Chief of Staff at Startmate, I realised pretty quickly that I would really benefit from having an external mentor who could help me get to the level I wanted to be at. 

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Nowadays we have a process internally to connect everyone in the team with a mentor, but back then I didn’t have a playbook. But, with a little effort and planning, I was able to line up a mentor who I can hand on heart say has played a really fundamental role in my growth over the last three years. Having a great mentor who isn’t ‘in the business’ is honestly such a career hack:

• They can push you and be honest with you in a way that people in your team might not be
• They can hold you accountable to personal goals you’re setting
• They’re the right ‘distance’ from the problems you’re facing, and can see how your own bias or opinions are getting in the way of good problem solving.

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The hardest part, though, is getting that relationship set up in the first place. Here’s what I did.

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1. Identify a list of dream mentors

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This is going to look different based on your needs and goals. Consider:

• Where do you most need support right now?
• What kind of qualities would work well with your weaknesses?
• How do you most want to grow? What kind of experience would help you get there?

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For me, I knew I needed a few things:

• An exceptional problem solver with a generalist skill set and strong people lens 
• Someone who wouldn’t pull punches/I couldn’t pull the wool over their eyes or talk my way out of things
• Someone I really admired/respected and felt had a level of values alignment, and who I could meet with in person

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Pretty early on I met someone who ticked all these boxes. I was lucky that the first person I asked said yes; I’d recommend pulling together a list of a few names for your first go. Ask other leaders in your business if there are people they know, search role titles on linkedin, try and do some crowd-sourcing.

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2. Frame up your ask

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The ask does depend slightly on your existing relationship with this person.

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If you’ve never met before, try and get a warm intro, and start with a smaller request.

• Ideally this is a coffee catch-up where you can drill them with career related questions and suss each other out
• Make it as easy for them as possible: frame up what you want to ask them about and why them

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If you have some sort of pre-existing relationship with them (or have now post coffee-catch up), it’s time to pop the question: will you be my mentor?

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Here’s how I structured my ask:

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• Ask the question right up the top: you’re wondering if they would be happy to mentor you
• Why do you want them to be your mentor?
  • This shouldn't be too hard because you’ve already done the work here
  • Why that person specifically? How does their experience/who they are align with your growth goals?
• Why should they want to mentor you?
  • Now’s your chance to flip the text a little. What will they get out of it? 
  • I wrote about how much I loved feedback, how I was a really fast learner, and that I thought it would be really rewarding to mentor me because of that
  • I also said we could have our mentor catch-ups during a run because I knew this person also loved running
• Define the parameters
  • I think a 1 x monthly meetup for 6 months is a reasonable first commitment; then you can both re-evaluate
  • What will the process be? Will you chat between meetings? This can be a conversation so that it’s something that works for both of you, but it’s really helpful to have a rough outline of how you see it working.

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3. Overdeliver and show your respect for their time and energy

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They said yes!!! Wow. (If not, repeat step 2 with other mentors on your dream mentor list). Now is your chance to prove to them straight away that deciding to mentor you was an excellent decision.

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For each of my catch-ups, I would send over a detailed write-up with the specific challenges I was facing, how I was thinking about them, and where I wanted help. My mentor would read through this and pull out additional things they’d noticed or wanted to talk through as well as my specific areas. We’d go for a run, talk through the write-up, and afterwards I would write down every single detail so that I could refer back to it and note the key actions.

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For the next catch-up, I’d make sure I provided any relevant updates on what we’d discussed last time so it was clear I was making changes beyond the actual discussion.

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I found going through this work was enormously valuable. It meant that I was framing up the most valuable way to spend our time, it meant that I got the most possible out of the process, and it meant that they could see how much it was unlocking me. Hope that helps.

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