• Mentoring

Mentor Development: Structuring Advice

Read a case study about structuring advice for your entrepreneur. Includes thought-provoking questions and best practice solutions.

Structuring Advice – Case Overview

Jason is a successful IT software designer, living and working in Toronto and he has been selling a piece of software called WebCan, which enables individual users to update web sites without having to continually instruct a third party to do it for them. Although there are other similar software products on the market, many are more costly and tend to be far more complicated than the product Jason is selling.

At the point of start-up there was no customer base but with the help of a Futurpreneur Canada loan, Jason was able to get trade endorsement for his product and since then the software is ‘flying off the shelves’. His sales forecast for year one was $200K but the business has grown threefold and with the ‘books’ about to be closed for year one the sales revenue is expected to exceed $600K.

Although this sounds like a problem all businesses would like to have, it is causing headaches for Jason. The biggest concern he has right now is how to reclaim his apartment which is starting to resemble a small factory distribution centre. This is not pleasing his live-in partner! Jason seems to be spending his entire time packing product with little time to do what he really wants to do which is to get on with developing new designs. As a result he is starting to feel frustrated for the first time and he is losing his focus and energy. He is also dealing with complaints from customers calling him up demanding to know when they can expect delivery.

William, his Futurpreneur Canada mentor, has been meeting Jason once a month but recently he has started to notice that e-mails are not being returned and the last meeting was re-scheduled at short notice. William is the IT Director of one of Toronto’s leading software houses and his background in IT was one of the reasons why he was matched with Jason. He is now starting to become concerned about Jason’s lack of focus and would like to offer some mentoring advice. William originally encouraged Jason to take advantage of market conditions and now feels partly responsible for Jason’s predicament.  He wishes he had given Jason advice around managing the anticipated growth. William has a clear idea of what should be done next but does not want to take the initiative away from Jason.


  • What are the mentoring opportunities available to William?
  • How could William help Jason get back on track?
  • What role does William play in the problem solving process?
  • What are a couple of suggestions on how William can provide motivation and incentive for the action plan Jason is creating?

Structuring Advice – Best Practice Solutions

  • Jason has had a great first year in business. Unexpected growth can be a real concern for new entrepreneurs who are working from a business plan that they have already outgrown. The fact that Jason is running three times ahead of his sales budget has presented Jason with problems that he had not anticipated on day one.There are several mentoring opportunities available for William. Recognizing the early success of the business is important – either through the Futurpreneur Canada Business Awards or through informal celebration. The next opportunity is to challenge Jason to revisit his plan to accommodate the new reality of the business. This will ensure he can consider the current and future needs of the business as well as the impact on his relationship at home. A further worrying factor is that William’s e-mails and calls are not being returned which is an indication ‘that all is not well’ for Jason and may be a symptom of other issues needing to be discussed.
  • Timing is all important to get Jason back on track. The fact that he is ignoring calls is a recognizable side effect of dealing with a stressful situation and a call for help. The first priority is for William to persuade Jason to dedicate some time for a face to face meeting. This may have to be a time and place of Jason’s choosing so that he retains an element of control over the situation. Next, William should prepare for the meeting in order to structure the conversation in a way that empowers Jason. There is a delicate balance between pulling and pushingi.’Pulling’ is an approach that helps Jason to reflect about the triumphs and the frustrations of the last year so that he can learn from his experience. Jason will retain ownership and gain much needed focus for the future. ‘Pushing’ encourages the entrepreneur to consider the consequences of the options available. For example, what impact does the inconsistent customer service of today have on customer retention? William must listen and ask the right questions. William needs to know the key challenges Jason is facing in both his personal life and his business life. Good mentors need to balance their approach and to help with both of these areas.
  • Once the challenges have been clarified, the next stage is to help Jason focus on his options. In addition to contributing to the identification of alternatives, Jason may need encouragement to keep focused on only those choices that will resolve the urgent issues. For example, if his goal is to spend 80% of his time creating new products, then he may need help in other areas i.e. admin, finance and sales. All choices have consequences. William’s role is to encourage and to challenge Jason to adequately weigh the options rather than go with the first one that comes to mind. An effective technique is to ask Jason to list the plusses and minuses of that option. As Jason’s mentor, William can take a helicopter view of the options presented and see if there are any possible creative solutions he can help him with. Ultimately, William needs only to confirm that Jason is confident in his decision as the business owner. Despite “knowing” the best course of action, a skilled mentor will help the entrepreneur find the solution instead of telling him or her the ‘answer’.
  • Through questioning and problem-solving techniques, William now has Jason thinking about the ‘road ahead’. The final step is to encourage Jason to move forward and take action. At this final stage, it is important that Jason’s plans follow the SMART principles: Specific, Measurable, Achievable, Realistic and Time boundii. William needs to challenge Jason to be proactive so he feels more in control of the business operations. The desire and will has to be Jason’s responsibility. With a ‘commitment to act’, Jason will be able to take charge and move his business forward. Meanwhile, William will be able to know that he has empowered Jason and not simply made the decisions for him.

i Mike Pegg. The Art of Mentoring. Management Books, 1999.
iiMealiea, L.W., & Latham, G.P. Skills for Managerial Success: Theory, Experience, and Practice. Chicago: Irwin, 1996.

Structuring Advice – Key Learning Points

  • Pulling vs. Pushing. In discussions between mentor and mentee, two main methods are used: ‘pulling’ and ‘pushing’. Pulling calls on the ability to offer an atmosphere where the mentee feels able to share their agenda, interests and goals. This is achieved through listening, asking the right questions and drawing out the mentee’s own answers to problems. Pushing, on the other hand, calls on the ability to offer stimulation – to offer creative ideas, challenges, knowledge, success stories, models and tools, leading-edge thinking and wisdom. Good mentors balance these two approaches. When in doubt, they ‘pull’ rather than ‘push’. Why? The mentee must stay in charge and fulfill his or her agenda. That way the mentor ensures the mentee finds the session personal, practical and profitable.
  • Following a structured approach. Although the mentee needs to take charge of the agenda, the mentor is able to support the mentee by using a structured approachiii. The 5C’s approach requires the mentor to plan an approach and think ahead about what questions to ask at each of the key stages: challenges, choices, consequences, creative solutions and conclusions. Another tried and tested model is GROWiv:
    • Goal – What would you like to talk about today?
    • Reality – What is going on right now (in your business)?
    • Options – What options have you considered? What are the plusses and minuses?
    • Way Forward – What will you do in the short-term, medium-term etc?
  • Problem solving: Helping an entrepreneur find a solution may take a few minutes of a conversation or several weeks of confidence building and personal support. Mentoring is not always about finding short-term solutions but listening and reflecting so that the entrepreneur is able to discover the solution for themselves.
  • Giving constructive feedback:There will be occasions when the mentor needs to challenge his or her mentee and to do this in a supportive manner requires feedback. This is particularly helpful if the client is having difficulty accepting the reality of his or her situation. Here are some points to consider when giving constructive feedback:
    • Focus on behavior.
    • Be specific.
    • Separate positive and negative.
    • Be prepared to give and receive.
    • Be honest.