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Mentoring Process: The Secret to your Mentorship Success

A Free downloadable Guide to success for Mentors and Mentees

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How to get a new Mentoring relationship or “Mentorship” off to a good start? We cover this and provide the Workbook that gives you the tools you need to succeed from start to finish.

Congratulations, you have passed the first hurdle to self-awareness and self-improvement: you have identified the need for Mentorship. 

Now that the "Mentor and Mentee" are ready to meet, both may wonder:

  • Are we ready?

  • Do we have a plan?

  • What is the best way to start? 

I will take you through 3 Secrets to make your Mentorship's successful. 

  1. Preparing your personal plan

  2. Setting yourself up for a successful first meeting

  3. Making a Contract to track goals and results

Let's review some basics

What is the Mentorship? It is a relationship that creates a sounding board, confidential advisor and promotes personal growth.

Mentorship refers to both of the traditional roles of Mentor and Mentee. These roles generally work as the "master and the appreciece relationships." However, as I have pointed out in the New Mentorship Model, the more rewarding approach is to appreciate both parties bring knowledge and life experience to the table. Respecting this diversity in backgrounds and experiences can enhance the Mentorship. For this discussion, I will refer to Mentor and Mentee more generally to the "mentorship partner," meaning either of these roles.

Throughout these steps, I will refer to my free downloadable Mentoring Process Workbook. So please download your copy and follow along.

Step 1 — Prepare yourself 

Engaging with someone else about yourself starts with an honest self-assessment. The other person needs to understand your motivations and goals, of course, but they also need to know something behind those "bullet points."

Share what is important to know about you in the Workbook section 1 - 5 Things about me. 

Now dig deeper. Do a personal SWOT analysis

Don't overthink this. You likely know your strengths and weaknesses already. Putting your SWOT in writing may be confronting, however, raising your awareness of who you are is an essential ability needed for growth. This process can test your awareness of “are you who you think you are” (or want to be).

Assessing your Opportunities and Threats may be more challenging.  You may need to go through a series of questions to understand what these are for you.

  • An opportunity may be a problem that causes you to rethink your approach or plan.

  • A threat may be an external outcome to a Weakness.

It is good to make a start, but this SWOT analysis is something you may want to revisit for yourself and with your mentorship partner.

Now that you have documented what is vital to know about you and your SWOT.  Use this work to shape Goals in the next section.

The important of Mentorship Goals  

These should cover the essential points you want to get out of the Mentorship - but more importantly, the results you want to see in your professional or personal life. Be specific. Focus each goal on the outcome. Why do this step? Because it's good to start with the end in mind. Complete the Workbook section 2 - My Mentoring Goals.


Also, note that goals and outcomes may not be realized in the way you expect. So keep your options open, you may get a promotion, but it may take learning a new skill or changing jobs to get it. You may learn to lead by learning to be a better member of a team. So be open and learn along the way. Having a plan to succeed focuses you on making yourself ready to create the right outcome.

Review the entire Mentoring Process Workbook. Making yourself familiar with the next steps will make your first meeting go smoothly. Being prepared and on time for the first meeting is the first sign of respect that both parties should prioritize. 

The next priority is always to bring something of value to each meeting. For the first meeting, this means being ready to share the kinds of information suggested on Workbook section 2 - My Mentoring Goals.. It provides the Why you are there and What you hope to achieve by working in Mentorship with your partner.

Step 2 - Make your first meeting a Success

As you and your mentorship partner make your introductions, start by reviewing the each of your goals. Look to understand the other person and what they are sharing. Share common ground and discuss differences.

Next, it is helpful to time-box the conversation since time can quickly pass on just getting to know each other. Open-ended discussions are essential, but Mentorship is also about outcomes and respecting each other's time. It is good to be prepared to get through to a 'next steps' stage at the end of the conversation.  


Suggested timing for a 1-hour meeting is:

20 Minutes for Worksheet 1 and 2

10 Minutes for Worksheet 3 

20 Minutes for The Mentorship Contract

10 minutes to update the Mentorship Dashboard


Start by getting on the same page 

Once you have addressed Confidentiality, cover the content of Workbook sections 1 and 2, review your:

  • "About me" statements

  • SWOT analysis

  • Goals and planned Outcomes

Note that both parties should do this step. It is important for alignment of joint goals later.

As you each discuss these 3 points for each partner, think about where you have things in common and where you differ. See past the wording to the meaning. Are you saying the same thing in different ways? Or maybe your points seem similar but are not. Listen and make notes.  


When you Partner (Mentor or Mentee) discusses their goals and objectives, write them down in Workbook section 3 My Mentoring Partners Goals. If something is is unclear, check for understanding. But note, these are things the other person has chosen to say. They are not up for debate. They are their truths, so respect them. Discussion about goals can come later. This is not that moment. 

If you have time, it is constructive to get through this next section while in your first meeting. 

Both of the mentorship partners will likely not have the same motivation, goals, and objectives for their Mentorship or for their personal goals. However, alignment is helpful. If the Mentor wants the Mentee to learn a skill from them, but the Mentee has other plans, this lack of alignment can cause frustration from both sides. So, the first step in the Roadmap is to document goal number one for each person.  

Think about the timing, action, and outcome related to that goal. Please write it down. Take personal responsibility for your part in making your goal happen.  

Since this is a joint document, consolidate input from both partner's versions and transfer the Shared Objectives to the Mentorship Contract (this is explained more below).

Step 3 - Create a Mentorship Contract to ensure Success

Mentorship Contract Confidentiality section of the Workbook. Your discussions are private and personal and should stay that way. Trust and Confidentiality are key to successful Mentorships.

When you do something important you write it down, document the details and track the results. Great mentorships should do this.

Since this is a shared contract, create a version with the same information and align decisions to ensure you are both literally on the same page.

If you have not already, agree to the Confidentially rules and clarify any open issues between you.

Your joint way of working

It may seem a trivial thing to do, but take a moment and discuss how you will work together:

  1. Communication: via phone, video chat, or some other way.

  2. Meetings: calendar them if possible, or at least agree to general timing.

  3. Agenda: agree to how they will be created.

  4. Action: (and next step) tracking, agree to the approach

  5. Dashboard: review use and timing.

  6. Discuss tools: if any are to be used. Confirm email address and electronic files repository, if used.

As a project manager, I can tell you the more structure you give to the small issues, the more time and mental space you will have for the significant issues. So don't waste valuable meeting time on housekeeping. Get it out of the way and follow the agreed-to processes.

Mentorship Shared Goals and Expectations

Consolidate the Goals you have discussed up to this point. Note that you may include one or two personal goals for each partner and one goal for the Mentorship since they are shared goals. Doing so provides a nice balance between individual outcomes and the process of Mentorship itself.

Identify the shared Expectations and Accountability you both have to your Mentorship. The Expectations referenced refer to how your Mentorship works. Setting expectations that are known and can be met by both parties can clear up misunderstandings or wrong assumptions before they happen.  

If you have time, it is constructive to get through this section while in your first meeting. 

Both of the mentorship partners will likely not have the same motivation, goals, and objectives for their Mentorship or for their personal goals. However, alignment is helpful. If the Mentor wants the Mentee to learn a skill from them, but the Mentee has other plans, this lack of alignment can cause frustration from both sides. So, the first step in the Roadmap is to document goal number one for each person.  

Think about the timing, action, and outcome related to that goal. Please write it down. Take personal responsibility for your part in making your goal happen.  

Since this is a joint document, consolidate input from both partner's versions and transfer one agreed and shared goal to the Dashboard.

Goals may directly align or may be different goal for each partner, though these goals may intersections. In an example of an alternative roadmap, John may still work on his plan, but Marsh may have a goal to take a finance class in the same timeframe. John’s plan may benefit from Marsh’s increased finance knowledge, but the outcome may not directly relate to John’s goal.

The suggestion is to focus on one goal each to allow for progress in the next session. Too many actions that don’t get addressed between meetings can demotivate the Mentorship. However, it may make sense to do more depending on the situation and the time available to work on these goals before each mentoring meeting.

The Mentorship Dashboard

Make a short Agenda to focus your conversation: a new topic, update, review the goal or the process to attain the goal. Make time for both parties to present Agenda items before or during the meeting.  

The Mentorship Dashboard can be created by both partners before the meeting and reviewed again at the end of each session. Establish this in your Way of Working or Expectations discussions. 

If you can, link the agenda to one or more of the goals set out in the Roadmap and Shared Goal you are focusing on.

The Dashboard does not represent your conversation or "through-put." It documents the "inputs" and documents the "outputs" of the conversation. You are not making detailed minutes of the meeting unless required for some reason. 

However, you do want to agree to the Actions as this documents the work needed to progress your goals. Ownership and due dates allow you to take accountability and should be a discussion point in every meeting. Use the previous meetings Dashboard to review planned actions, assess their effectiveness toward the goal or outcome. Update the current meetings Dashboard following discussion and agreement on next steps.

Following the meeting, you will want a way of referring to the actions you have taken. You may think what to use your calendar to create a reminder. For more complex plans, you may want to use a tool such as Trello to allow for joint tracking of tasks.

Honest and Frequent Evaluation

As your meeting comes to a close, evaluate the health of the Mentorship. Are you meeting the goals set out in the first meeting, have those goals or outcomes changed? Do they need to be revisited as part of the future discussion.

What is the evaluation of the Mentorship? Is the process working for both parties? Do adjustments in expectations or way of working need to be made?

Evaluating each meeting does not need to take much time. It can clarify actions to be taken or allow for other adjustments by either party. It can keep the Mentorship open and honest to ensure the meetings are valuable and moving in the right direction.  

With a Dashboard complete, you have everything you need to plan or confirm your next meeting date. And you know the actions that need to be progressed before the next meeting.  

You've established your Mentorship as two mutually respectful and knowledgeable Professionals at possibly different stages in your life or work. Now you are Mentoring partners who understand the goals and requirements to succeed in your shared objectives. And you are ready to build on the personal growth that Mentorship can bring.



So what did you think of the new mentorship model in action? Did you use the process? Please tell me about your success or areas you struggled.

Was there a step I forgot? Something in the Workbook you found missing?

If so, please leave a note in the comments section below or email me at  projectskillsmentor@gmail.com. All feedback is appreciated.