Guide 2 of 9
Prepare for Your Match
How to evaluate recommended mentors, define a learning objective, and approach each conversation with purpose.
The platform recommends professionals whose background, industry, role, or career path may be relevant to your interests. But the choice of whom to contact, and why, still belongs to you.
Recommendations Are a Starting Point, Not a Decision
A recommendation is not the same as an assignment. Your role is to review those recommendations, think critically about which conversations would be most useful, and decide where to focus. Before reaching out to someone, ask yourself: Why might this person’s experience be relevant to me? What could I learn from this conversation that I cannot easily learn online?
Relevance Matters More Than Recognition
The best person to contact is not necessarily the person with the most impressive title. It is the person whose experience is most relevant to what you are trying to understand. If you want to learn what an entry-level role actually feels like, someone who started in that role recently may be more useful than a senior executive. Each level of experience offers a different type of value.
Start With a Learning Objective
Before reaching out to anyone, define what you want to learn. Your learning objective can be as simple as:
- I want to understand whether this role fits how I like to work.
- I want to learn how people break into this industry.
- I want to understand what skills I should build over the next year.
- I want to compare this path with another career option I am considering.
A learning objective helps you decide which recommendations are worth pursuing, and helps you write a more focused booking request note.
Do Not Contact Everyone the Same Way
A strong request note should reflect why you are reaching out to that person specifically. Shorter is usually better, but it should show that you have reviewed their background.
Weak: “I’m interested in your career and would love to chat.”
Strong: “I noticed that you moved from engineering into product strategy. I’m exploring roles that combine technical problem-solving with business decision-making, and I would value the chance to learn how you navigated that transition.”
Do Not Treat a Recommendation as an Obligation
Being recommended a professional does not mean that person owes you a conversation, referral, resume review, job lead, or ongoing mentorship. The recommendation creates a possible connection. It does not create an entitlement.
Key takeaway
A strong recommendation is not defined by title, prestige, or brand recognition alone. It is defined by relevance. The more intentional you are about choosing who to connect with, the more valuable your coffee chats will be.