How to build an effective start-up mentoring relationship?

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At a workshop just yesterday, a young entrepreneur shared how they were assigned a mentor. But due to the uncertainty about the scope and nature of the relationship, the mentoring never really got going. It lapsed after just a couple of sessions.

A healthy, flourishing mentoring relationship is based on some common sense ground-rules and a recognition that like any relationship, it requires investment from both sides. Mentors need to be careful to understand the implicit boundaries in any relationship, otherwise trust and rapport could be undermined. Equally, a mentee needs to open up to the learning opportunities, even if this feels uncomfortable. These things are true even if the mentoring is provided free of charge, or if the mentor is chosen or assigned. 

In this article, we will discuss an outline checklist of the factors that help build an effective mentoring relationship. 


Mentoring can be designed to meet a wide spectrum of needs, from hard-edged challenges like enhancing the probability of venture success, through to the development of the personal qualities of the entrepreneur. The underlying purpose of the mentoring needs to be considered at the programme level, as it will affect the design of the mentoring relationships and the kind of expectations that are set by all involved. 

It is also important for the mentor and mentee to share with each other their purpose in engaging in the mentoring relationship. Ethically, the mentor needs to the transparent with the mentee if there are other dimensions to their involvement in the mentoring programme; such as paid consultancy, or if they are promoting a professional services business, etc. 

Sometimes, the real purpose is not apparent or hard to express. This is where listening and careful question can help. It’s worth spending time on this early on. 


It is important to remember that whether the mentor is assigned to a mentee, or the relationship has emerged organically through network of relationships, both sides still need to choose to make it work.  The mentee needs think through the purpose of the mentoring and decide what kind of mentor they are looking for. The mentor also needs to decide if they are the right person for the mentee and whether they feel the mentee is right for them. 

Many mentoring relationships go wrong because there is simply a mismatch in personal chemistry, or in professional interests. It’s better to surface this early and prompt a re-assign of the mentee, than for both parties to struggle on. More commonly, misalignment in choices just leads to meetings cancelled or deferred, with a relationship based around infrequent meetings and inconclusive disucssions. 


The mentor needs to establish early on the scope of the mentoring. This is important as the mentee might be expecting the mentor to stick to business, whereas the mentor might try out their pop-psychology theories, or discuss the latest management fads. There are real risks in the mentor generalising from their discussions, and going into areas that the mentee considers private, such as family or relationship history. This is especially true when the mentor and mentee are from different genders or ethnicities. 

It is good practice for the mentor to ask if they need to go beyond the agreed scope. For example, if the mentor has noticed aspects of the mentees behaviour that might indicate a more general issue with relationships, the mentor should ask if they can discuss this. This “contracting-in-the-moment” can build trust, as the mentee learns that the mentor will ask if there is a possible change of scope. 


Boundaries are somewhat related to scope in that there might be subject areas that are definitely off limits. This might be subjects that might appear over-familiar, but also where the mentor is trying to sell or capture data for some other purposed that is not clear to the mentee. But boundaries also encompass stylistic issues, such as the mentor becoming overly directive, too advisory, our overly curious. 

Also, is contact at evenings and weekends tolerated? 


A clear focus scan help any mentoring relationship move in the right direction. Often, this can be simply about the venture or project the start up founder is trying to drive forward. It often helps to express this as a problem statement, or a question, which helps frame the discussion.  However, it is sometimes the case that the mentee is not clear about their focus, and might need time and understanding for the real focus to emerge. 


Key to any relationship is the rapport and chemistry that builds up, often with patterns formed early on. A key part of creating this rests with the behavioural style the mentor uses. Again, it’s useful to discuss this early on so that expectations can be aligned. If the mentor is too prescriptive, this can alienate the mentee. However, if they are too accommodating, the mentee might need feel there is not enough value-add being created. 

One of the most commonly used taxonomies of intervention styles is the Heron Model, originally derived rom psychotherapy, but also relevant to mentoring. See link. 


An agreement on the regularity and timing of any meetings or discussions is very important, in order to set the right pattern. One problem that can emerge is that the meetings or too irregular, and this means that a lot of catch up chat is needed rather than added value dialogue. Diary congestion on both sides can also make the frequency irregular and uneven. 

But just how much contact is appropriate in entrepreneurial mentoring, given that the mentor shouldn’t be too involved in operational detail? Monthly meetings or calls are common, but this might need to flex during peak or intense periods. Quarterly meetings suggest both sides are more comfortable with more reflective conversations. If the sessions are weekly, that can be quite an onerous commitment for the mentor. 


The medium used in the contact is a very important topic. Face-to-face meetings are usually preferred, but even travelling across the same city can be time consuming and onerous. Sometimes it is better to use more regular phone contact.  Yet, we often associate phones, and especially mobiles, as useful for “chats” or catch-ups rather than deep dialogue. Also, young entrepreneurs are increasing using a wide spectrum of different platforms, such as Messenger, WhatsApp, etc. 

Certain social media platforms could imply a degree of informal and possibly even intrusive contact.


If the meetings are in-person, the choice of location can be important. Commonly, this might involve meeting in  a cafe, but also possibly a meeting room at a university. If this is on campus, this can involve quite a lot of travel for the mentor. The considerations involve the degree of privacy, the distraction levels, and degree of formality. For instance, meeting on campus in a coffee shop can require super-human patience from the mentor as the discussion is constantly interrupted by the mentees friends. At the other extreme, a meeting on campus can create a rather formal atmosphere, where the mentor could be seen as an extension of the university faculty. 


Both mentor and mettle need to agree what information they request from each other. It is usual that LinkedIn connections will be made. Also, it would be common for the mentee to forward a CV. But what other information is needed? Instagram? Twitter?GenZ spend their lives on various social media platforms, but for the mentor to join them there could be seen as intrusive or interfering. The mentor suddenly appearing as friend request on a mentees timeline could be off-putting, and vice versa. 

These are 21 century problems!


Most important of all in fact, is the agreement on confidentiality. This might be seen as straight-forward, but there is always the possibility of breaching confidence in response to well meaning question from a programme director, accelerator manager, or angel investor. This might be a simple inquiry such as “how is Mary doing?” In responding, the mentor might be inadvertently and unknowingly breaching confidences. 

It’s good practice to agree early in what can and cannot be shared, possibly with an agreed statement that both mentor and mentee can use in responding to questions about the mentoring discussions. 


This concern for confidentiality is linked to the related concern of the mentee about whether they are being judged or evaluated in some way. If the mentoring is linked in anyway towards the award of cash or prizes, there is a risk that the mentee seeks to please or impress the mentor in some way. This is natural human behaviour. 

If there is any form of evaluation, even if it is a soft ranking or assessment, this must be transparent to the mentee, otherwise trust might be broken both ways.


Given the range of issues outlined above, it’s not surprising that sometimes it is better to write this down in  memo or just an email, so that both sides are clear. This can also highlight any area that is missing or unclear.  


In summary, a trusted relationship between mentor and meet can only really emerged once they have navigated through the issues outlined above. Both mentor and mentee are human, and it is important that any mistakes or lapses are discussed in an adult way. Having a clearer contract or psychological understanding makes any breaches or moments of rupture easier to resolve. 

Like any relationship, it grows by resolving differences not by avoiding them. 


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To learn more about being a mentor, check out our Dynamiqe Mentor Accreditation Programme (DMAP):

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