How can you overcome shyness when seeking a mentor?

This is always an interesting one. To be honest, it's like a muscle you need to build. There are definitely some awesome best practices that have already been shared, but in my experience, when you boil it down, it's about being bold. You need put yourself out there and ask. Find the right person, jot down an elevator pitch, go beyond your comfort zone, etc., but at the end of the day, you've got to take the leap and ask.

A mentor, much like a coach will have their own areas of expertise. Determine if you are looking for a "life" mentor, a career/professional type mentor. And that is a rabbit hole in and of itself. The mentor who helps you become a better leaders or manager, may be different than the mentor who helps you with accounting best practices and advice. It's super important to have an idea going in to the ask of what support you are looking for. If you don't know what help you need, it's very difficult as a mentor or coach to help.

Defining your goals and knowing what you wish to focus on will provide you the confidence to both engage with a mentor but also speak to what you desire more. Identifying where you are now will be support your mentor in guiding you towards where you wish to be (even if you haven't clarified it for yourself yet).

It is important to remember that being asked to be a mentor is extremely fulfilling to the person being asked. Most people I know are flattered to be asked, and even if they are unable to help due to other commitments, will respond with kindness, and perhaps suggest other resources. Please don't let fear dissuade you from asking. Be a bit creative in the way you make the request. Stand out from the crowd. Be your authentic self. The worst that can happen is the person says no. And, then you move on.

It's like going into therapy. Know what you hope to achieve with your mentor and make sure it's realistic and achievable. Also, make sure you share this with your mentor so they know what you're goals are. "I'm looking for mentorship to help me ______ in the hopes of _______. This also allows you to circle back in a few months to see how close you've come to reaching your goal.

Preferably look for mentors outside your immediate group or team. This will help you have open conversations and the mentor can also offer more candid feedback. While researching mentors, remember that they always dont need to be very senior folks in the organization. Seek out wisdom and that can be found in unexpected places. A good read would be Wisdom at Work by Chip Conley. It will help you think differently about mentors.

It's often assumed that a mentor is someone older with more life experience; pursuing this type of person is helpful as they tend to bring a sense of wisdom to the table that younger people still need to acquire. If this is the case, a great way to find a potential match for you is to ask family friends for recommendations, as you'll find that mentors are often more accessible than you think. There's also a scenario in which your mentor could be the same age or possibly younger; they may have achieved early success in an area you're interested in and could provide a lot of insight and guidance.

Begin by asking a straightforward question to initiate the conversation and demonstrate your interest. Follow up with meaningful questions that show you're genuinely engaged in the discussion. Sometimes, the person you inquire of will take the initiative to inquire about you in return and explore how their expertise can be of assistance. It often commences with a small, friendly gesture.

Leverage on your connections and network to identify a mentor who you will be accountable to and that has a wealth of knowledge and experience in the industry. A mentor’s time is valuable so as a mentee,be prepared before any scheduled meeting so as to make the conversations worthwhile and be ready to put in the work.

My perspective on mentorship is that it should evolve from an already existing personal relationship. Mentoring takes time, effort, energy, etc. It is a two way investment for the mentor and the mentee. I have experienced that if there is not a pre-existing personal relationship, not necessarily a profound friendship, the mentor may not prioritize or give the significant importance to mentoring. Before reaching out to mentors or before considering someone a candidate to be a mentor, I encourage to start by building a relationship, get to know them, are the values aligned with yours, understand how do they feel about mentoring, etc. Setting a strong personal foundation can go a long way to really reap the benefits of mentoring.

People have very different levels of trust expectations for themselves when it comes to engaging with others, which may be perceived as shyness. For someone that needs to build high levels of trust with someone or a process before opening up and asking for mentorship, ask yourself if going outside your comfort zone to build a new relationship is what you want. Be honest with yourself about what it is you are seeking to accomplish. Develop a clear framework for the first few steps in the process. Provide yourself a few examples of what successful mentorship looks like during those first few encounters so you can gauge success, building your trust in the process and relationship. Give yourself and the process latitude to be flexible.

Confidence is not expressed only through excellent oratory and presence. Your self awareness and ability to communicate with clarity are essential. Also understand that shyness is also a reflection of ego trying to self-preserve. Shyness indicates a fear of rejection and fear is an expression of the ego. So try to set these inhibitions aside and seek out counsel.

It is okay to be and to feel shy or awkward when asking for help. It is okay to admit that to the person you are asking. Once you have identified someone that you feel can help you, start there. Tell them why you are reaching out and what you are hoping to learn from them. Most people will be honored and flattered that you are asking them. You may be surprised to learn that they once felt the same way you do today.

Once you've identified a few potential mentors, it's time to reach out to them. This can be a daunting task for shy people, but it's important to remember that most mentors are happy to help others. Send them a brief email or LinkedIn message introducing yourself and explaining why you're interested in mentoring with them. Be sure to mention your goals and what you hope to learn from them.

Its also very interesting from the mentor's point of view to know why you have chosen her/him . If you do your homework and research the works and accomplishments of the targetted mentor,its good to highlight things that made you chose them in the first contact. When you ask to discuss an article further or ask questions about a certain training or a specific job in their career ,it will trigger the interest of the mentor and she /he will be more eager to assist and support

One of the most effective ways to build trust is by following through on feedback. Putting in the work to improve oneself is the best way to build trust. I knew the CEO of a company who once said "Trust is built in drops and lost by the buckets".

Like most relationships, pursuing a mentor will likely be an incremental process that requires you to build rapport and trust. You may reach out and immediately get a "yes," which is fantastic; however, people are busy and selective with their time, so it's best to consider this and give yourself time to foster and nurture the relationship.

Respect your mentor's time and boundaries. Understand that they may have busy schedules, and be mindful not to overwhelm them with constant requests. Make the most of the time you have together by being well-prepared for meetings. While maintaining a professional relationship, try to build a personal connection with your mentor. Share appropriate details about your life and interests, and show genuine interest in theirs. This helps create a more comfortable and trusting atmosphere. By actively contributing to the mentorship, being receptive to feedback, and demonstrating your commitment to growth, you'll strengthen the bond with your mentor over time.

Understand that this is an investment on both side requiring trust, transparency, communication, and more. Ideally you'll want to cultivate something for a long term growth if possible. These relationship when fostered well can be mutually beneficial and last a life time!

After asking advise advise from someone you respect and feel would be a good mentor, take the advise. Apply it, then let them know you took their and advise and how it worked out for you. This help build trust both ways, because while you are working on trusting this persons advise in your life, they are also trusting you they are giving. Why give advise to someone who rejects the advise most of the time, the more a mentor trusts you, the more they will give insight into their bank of knowledge. They also want to know what you will do with the advise you give them, use is wisely, ignore it, or maybe even abuse it?

While meeting with the mentor in the initial stages, one more suggestion would be to go with a specific situation (from past or present) and discuss that up first. Define options and weigh their pros and cons with the mentor and get their perspective. This can act as an icebreaker and can help overcome shyness and focus the initial meetings without any awkwardness. Once we build the rapport, then it gradually becomes easier to talk about strengths, weaknesses and get the feedback we are looking for. Making an action plan with this feedback and working on it with your mentor has no alternatives though.

Feedback is how we learn, so embracing that is key as it may not always be comfortable but then again growth is not always easy. Remember to keep it respectful and to speak up and ask for clarity within the feedback process. Keep an open mind and again change takes time.

While asking for feedback, don't ask only about your weaknesses. I would suggest spending more time on strengths. If you discover your real strengths and then work to transform them into super powers, it will be a great way to overcome weaknesses. Do what may Superman could not overcome Kryptonite. So avoid some of the negatives but make sure you double down on the positives.

If you're feeling reluctant to receive feedback, it's most likely that there's an underlying fear of rejection or limiting belief, such as, "I'm not capable of getting better." These limiting belief systems can get in the way and close you off to growth opportunities; do your best to familiarize yourself with yours to stay open to any feedback. As you become more aware of the things that may block you, you become more receptive to receiving and integrating feedback, understanding that it's neither "good" nor "bad"; it's all helpful information in your pursuit of growth and prosperity.

Once your mentor becomes more familiar with you, they may offer valuable suggestions. However, it's crucial for you to take the initiative as well. Be diligent in doing your homework, make notes of areas where you require clarification, articulate your strengths, and communicate your aspirations. The more specific and precise you are in your interactions, the more valuable the feedback from your mentor will become.

One more thing which matters is, be honest through the whole process. Sometimes it will work and sometimes it won't. It is important to be open and honest about it so that a course correction can happen, and it becomes an enriching exchange. Another force multiplier is, if this whole process is documented, then that helps a lot as well. It allows us to see the progress that has been made and acts as a catalyst to do more. It is important to understand that such relationship helps the mentor as much as the mentee.

Attitude is the strongest, most impactful input any living creature will judge first, both rationally and irrationally. Walking in, or gathering in a meeting, expression, language, manners and attire will make the other person establish a judgement that will be hard to change afterwards. This is the known "no second chance for a first impression". Afterwards, more social and intellectual issues as well as qualifications, experience or recommendations will play their importance. I have always preferred people with the right attitude than with a full achievement CV.

There could be 2 main reasons you feel shy when seeking a mentor. (a) you are shy about sharing your fears & dreams (b) you dont want to burden someone by appearing needy. If it's (a) you can negate by taking time to build a rapport, then sharing & seeking advice based on your comfort level. If it's (b) establish clear call and meeting times in advance and set out clear schedules that do not put the burden on either to be available randomly. But the important thing is that you have taken the first step to find a mentor, this means that you've crossed the biggest hurdle of identifying that you need help and the areas that you need that help in. Kudos on that.

Remember, mentors want to help you and many will have dealt with a myriad of personalities. Mentors are human too, so be honest about your shyness, this will enable the mentor to prepare for your meeting and they may even give you tips on how to overcome your shyness in certain situations. My partner can be shy sometimes despite having been a CEO of a global organisation. Shyness doesn't determine ability.

IMO, mentorships don't have to provide value for only one person. Consider the fact that you may bring value to the relationship, even if you're the one being mentored. Your perspective and your experiences are valuable, and you'll have a much more fruitful (and less awkward) relationship if you can see it that way!