Connect & build a relationship


Teach, guide, counsel, encourage, introduce


Wrap up & set expectations for the future


Connect & build a relationship

Guide to your 1st meeting


Conversation Guide: First Meeting between an Entrepreneur and an Advisor or Mentor

Congratulations, you’ve been matched!  In some cases an entrepreneur may have a question that can be addressed in one session.  However, in many cases the entrepreneur’s request will require more than one working session.  In any case, please follow these guidelines as a way to get started.

Before your first meeting:

  • If you are an entrepreneur:
    • Review the advisor/mentor’s profile and  LinkedIn profile in order to get a sense of their background
    • Be ready to clearly describe where you are in your business and specifically what needs you are hoping to address with this advisor or mentor
  • If you are an advisor or mentor:
    • Review the Entrepreneur’s profile and business Plan prior to the call

During your first meeting:

  • Start by getting to know one another – ask each other a question or two about what you learned in their profile, about their business, or even about how their day is going!
  • Then focus on the business need
    • Take the time to talk about where the entrepreneur’s business is currently and what the overall vision is
    • Then discuss the request for help and make sure the advisor/mentor clearly understands what is being requested
  • If appropriate, resolve the entrepreneur’s questions during the call
  • If the request will take more than one conversation::
    • Clarify specifically what the goal of the next call or meeting will be
    • Determine what (if anything) either the entrepreneur or the advisor/mentor needs to do in preparation for the next meeting
    • Agree on a meeting time and location for the next meeting

After any meeting:

  • As a courtesy, we strongly suggest that you follow up from the meeting by text or email to confirm any follow up meetings and acknowledge the time you spent together with “Thank you” or  “Nice meeting you”!
  • Confirm any additional meetings 2-3 days beforehand to avoid potential confusion or frustration with cancelled or missed meetings.

Let us know if we can support you further – just contact our program director, , if you need help.

Meet them where they're at

Making a meaningful impact as a business advisor or mentor on starts with understanding the individual you’re working with.

Our young entrepreneurs’ dynamic needs often include:

Gaining confidence in themselves Ability to remain financially stable while starting a business Healing from trauma and discrimination
Soft and hard business skills Trustworthy, knowledgeable, reliable, culturally competent, and emotionally intelligent support Access to flexible and individualized training
Roadmap and plan for achieving their business goals Relevant connections to people in their industry Access to potential customers for their products and services

Core tenets


  • We focus on building a relationship of trust first
    • The first part of building a trusting relationship is showing the other person you’re excited to meet them and collaborate! We encourage both entrepreneurs and volunteers to really proactively reach out to each other right away to have their first – and any following – meetings.
    • We listen, giving our mentees our full attention.  We avoid jumping to conclusions or immediately administering advice.  We demonstrate a deep interest in their success.
    • We focus on the entrepreneur’s intentions and desires, not our own desires for them.  
    • We work with the the whole person, providing personal support and encouragement when appropriate rather than always driving for momentum in their business.  
  • Our goal is to empower the entrepreneur to help themselves
    • We model and teach where possible, subscribing to the adage “if you catch a fish for someone they eat for a day, if you teach someone to fish, they can eat for a lifetime”
    • Where appropriate, we provide templates or initial frameworks such (eg a contract template, logo, or QuickBooks setup) which they can re-use with little or no help
    • We ask probing questions, encouraging the entrepreneur to fully consider their options and conveying respect for their point of view
  • We model businesslike behavior
    • We proactively communicate, come to scheduled meetings promptly and prepared, follow up on promises, and are responsive to emails and calls.  
    • We offer specific, constructive feedback, emphasizing the importance of these skills
    • High Expectations: Have – and maintain – high expectations for yourself and your mentee  while accepting that no one is perfect.
  • We subscribe to the lean startup model
    • We encourage entrepreneurs to start small, test often, and generate revenue as soon as possible versus seeking loans and investments as a way to get started
    • We focus on low and no cost alternatives, “bootstrapping” whenever possible



Teach, guide, counsel, encourage, introduce

What advising is / is not

What advising & mentoring is 

Advisors and mentors provide some combination of these four kinds of support based on what a young entrepreneur needs:



Teach entrepreneurs skills (both soft skills and Pathway-related skills), habits, and mindsets.



Ask probing questions, instill focus, and hold problem-solving discussions with entrepreneurs supporting them through their journey.



Provide specific advice on different areas of business, such as how to create a budget, a brand strategy, or develop a proposal.



Helping entrepreneurs actually build parts of their business, making relevant introductions in your own network, etc.

Advisors & mentors are confidants, partners in problem-solving, encouraging, curious, inspiring, and challenging while supportive.

What advising & mentoring is NOT

Direct “sponsorship” Focused on the advisor’s or mentor’s business interests Doing everything for the young entrepreneur
Too task-focused A conflict of interest Getting stuck in the details

Potential challenges

Relationships are complicated. Being aware of potential challenges can help you prevent or prepare for inevitable obstacles.

definition of roles and expectations
Conflicting values or a mismatch in personality compatibility Meetings are repeatedly
(or missed)
Relationship difficulties (broken promises, prejudices, etc.) and a
lack of commitment
Wanting to give up Unreasonable demands
for help and support

Pathway to Business Ownership

Our Pathway to Business Ownership Checklist is a great resource to use every step of the way as you support our young entrepreneurs in building their businesses.

The 5 C's

The 5 C’s



Challenge: The young entrepreneur explains to their mentor that they are having staffing problems and that staff are demotivated.

Choices: The mentor will help their young entrepreneur to think through the available choices or options to overcome the challenge. The mentor may ask “what are your choices (options)?”

The young entrepreneur may say:

  • I can fire them
  • I can ask them to submit a staff satisfaction survey
  • I can increase their salary by 5%
  • I can ask each one to come and speak to me

Consequences: The mentor will support the young entrepreneur to examine the consequences of those choices. The mentor may ask the young entrepreneur “what are advantages and the disadvantages of the 4 choices you have outlined?”.  The young entrepreneur would then explore each option in more detail and this process would be guided by the mentor.

Creative Solutions: Once the best choice has been determined, the mentor can work with the young entrepreneur and discuss creative solutions. This is a mutual and collaborative approach. The mentor can then help by sharing any knowledge and expanding on their own experiences with the young entrepreneur to arrive at a practical solution.  Wherever possible, the mentor should encourage the young entrepreneur to develop his/her own solution to the challenge. If the mentor has ‘ideas’ this is the time to share those ideas. The mentor must balance the ‘PUSH PULL’ mentoring approach. If in doubt, the best approach is always to PULL which encourages the young entrepreneur to take responsibility for the solution.

Conclusion: Bring the session to a conclusion by asking the young entrepreneur to sum up the key points of the meeting and to describe what will happen next. The young entrepreneur should be encouraged to act upon the agreed solution. The role of the mentor is to support and challenge the young entrepreneur to carry out the actions they have agreed upon, and the young entrepreneur should feel empowered to willingly take these actions forward.

The mentor can encourage the young entrepreneur to have a SMART action plan: Specific, Measurable, Actionable, Realistic and Time-bound.




The key skill when working with your entrepreneur is to LISTEN:

Look Interested

Inquire with questions

Stay alert

Test your understanding


Neutralize your feelings

A good listener DOES:

  • Recognize how the speaker feels about the subject matter
  • Look for points to agree with rather than disagree
  • Give a quick summary of what has been said, every now and again, to check that their understanding is correct
  • Give their full attention to the person who is talking by facing them and nodding in agreement

A good listener DOES NOT:

  • Interrupt a speaker or break the flow of conversation
  • Become distracted or let their mind wander
  • Let a mentee’s previous opinion affect them
  • Let prejudice get in the way
  • Act negatively or belittle the person speaking
  • Change the subject
  • Fidget or distract the speaker


Wrap up & set expectations for the future

Next steps

If you and/or your entrepreneur feel ready to wrap up the work you’re doing together, here are a few steps we recommend:
    1. Talk to each other about your readiness to wrap up the relationship. If you need any support on this, contact our Program Director! In that conversation, be sure to recap what went well, the progress made, and provide encouragement and support to the entrepreneur!
    2. Discuss the most pressing needs of the entrepreneur now, and encourage them to request an Advisor or Mentor on to meet that need!‌‌
    3. Be sure to rate your experience working with the entrepreneur – this will not be shared and will improve our ability to match you with the right future entrepreneurs
    4. If appropriate, feel free to leave the door open to the entrepreneur to contact you at some point in the future in areas where you’re comfortable supporting them.
    5. If you feel inclined, offer your feedback to the team to help us continue to improve our work.
    6. Match with another entrepreneur on!