Staff & Training

The Ultimate Guide to a Successful Workplace Mentorship

Ryan Chan

What is a workplace mentor?

A workplace mentor is someone who can help guide you in your career. Their role is to offer suggestions, lend perspective, act as a sounding board, provide wisdom, and empower you.

Why should I do a mentorship?

  1. You have someone that can answer your career-related questions, and provide good advice!
  2. You have someone that can help you stay motivated to accomplish your goals!
  3. You have someone that can provide you with a ton of knowledge, resources, and connections!
  4. You have someone that can show you new opportunities and career paths!
  5. You have someone that can push you to hone and learn new skills!
  6. You have someone that can help you discover your passions and interests!
  7. You have someone that can advocate for you and has your back — someone who can give you constructive feedback, but also celebrate your successes!
  8. You have someone that can become a life-long friend!

Who can be a workplace mentor?

A workplace mentor is often someone within your organization who holds more experience or seniority than you. This should be someone who has a gathered valuable insight throughout their career, and can pass on what they learned to you. This person can be someone you already know, such as manager or executive in your company. Or, it could even be someone that you admire and respect.

How do I ask someone to be my mentor?

If there is no mentorship program already in place by your employer or manager, you will have to take the initiative to reach out. Although mentoring relationships can emerge naturally after you have worked with someone for a certain amount of time, it’s encouraged to establish expectations and responsibilities of the mentoring relationship. Without setting those expectations, the mentoring relationship can easily be confused for a managerial relationship.

Before asking anyone to be your mentor, make sure you research their professional history, and search for commonalities in interests and goals. Then, try to have your boss or colleague make initial introductions for you. Or, send your potential mentor a polite and personalized message that states your intent simply and briefly.

Tip: If you want to ask someone to be your mentor, but feel like they might have too much on their plate, come back to them when they are less busy. Remember, you want to be able to spend time with your mentor on a regular basis, whether it be weekly or bi-weekly.

Expectations for Mentees and Mentors

For the Mentees —

If you found a mentor, remember these rules to make the most of the relationship!

  1. Be clear on why you want a mentor and what kind of help you are looking for in a mentor.
  2. Set a time and date to meet, and also establish how frequently you want to meet. Once everything is decided, make sure to stay committed to the process! Respect your mentor’s time.
  3. With your mentor, set goals for the mentorship. What do you want to accomplish? What do you want to grow in? Use these questions to guide you.
  4. Everything discussed in your mentorship meetings should be confidential. An agreement of confidentiality allows trust to be built between the mentor and mentee. Both parties need to develop the assurance they can communicate openly, and the more trust there is, the more truthful the discussions will be and the better a mentor will be able to help.
  5. Make each session count. Bring topics or questions that are on your mind, and ensure that each session is goal focused.
  6. As the mentee, if you are given any action items from your mentor, it is your responsibility to get those items done and report on your progress.
  7. From time to time, review the relationship. Make sure that the experience is still positive for both you and the mentor. And, make changes if needed to reach your goals.

For the Mentors —

  1. Choose your mentees carefully! There’s nothing wrong with saying no. If you know you’re too busy to take on a mentee, or you notice that a prospective mentee is showing signs of lack of commitment, organization, or motivation necessary to succeed — then by all means, decline the request. Effective mentorships take time, and it’s important to make sure both parties are willing to put in the work.
  2. Recognize your bias. Mentoring can be somewhat subjective, and the person you mentor might have their own biases or agenda. Weigh in each others’ suggestions and understand the different perspectives being brought to the table.
  3. Do not commit mentorship malpractice. According to Harvard Business Review, mentorship malpractice can look like:
    • Insisting that your mentees advance your projects rather than allowing them to develop their own work.
    • Handcuffing your mentee to your timeline, slowing their own progress when you are slow to get back to them.
    • Discouraging your mentees from seeking other mentors, isolating them from broader learning and recognition.
  4. Make sure to separate work from the mentorship. Don’t discuss projects you’re working on together for the company, or center discussions around business operations and the work performance of your mentee. Instead, discussions should focus on professional development of the mentee.

UpKeep’s Mentorship Program

In case we haven’t convinced you already to seek out mentorships, here are personal testimonies from members of our Operations Department who can attest to its immense value.

Mentee: Heather Grant, Operations Manager

“My mentor is Joe, VP of Customer Success, the one and only! I’ve been really lucky to have worked closely with my current mentor/boss, Caitlyn, for over three years, so I was hesitant to take on a new mentor at first. But, I’ve been enjoying it a ton! We talk about setting and achieving future goals, career paths, current and developing skills, and general life advice. It’s been a new experience for me having a mentor who isn’t my direct manager, and having to articulate my working style and skills differently than I do to my boss who sees them every day in action. It’s been an awesome growing experience so far, and I’m looking forward to continuing to meet with and learn from Joe! I appreciate all of the advice I get from both of my mentors so much, and I would definitely recommend mentorship to anyone who is interested! I’m really thankful for Caitlyn who encouraged me to step out of my comfort zone to receive mentorship from another leader in the company!”

Mentee: Katie Fegan, Executive Assistant

“My mentor is Katie Cannell, HR Director! I’ve learned so much about her career path, helpful resources, and best ways to work with my team and manager. I’ve been enjoying it a lot, and it’s always nice to have someone to bounce ideas off of and get updates on what’s going on in the HR world! I would definitely recommend a mentorship program for any company. It is a great way to get to know someone on a personal level and build relationships with coworkers!”

Mentee: Tyler Blum, Senior Recruiter

“My mentor is Garris Yeung, Senior Director of Sales! Garris has helped me overcome mental obstacles. His guidance has given me the confidence to ask more questions and be more direct — even if it may feel uncomfortable. The experience has been incredibly rewarding, and I would highly recommend everyone seek some form of mentorship or coaching.”

Mentee: Chelsea Cho, Project Coordinator 

“My mentor is Victoria Johnson, Customer Marketing Manager! I was always afraid to ask anyone to be my mentor because I felt like no one would be open to it. But, after just one meeting with Victoria, I can see how much value there is in doing mentorships. The amount of guidance, resources, and knowledge has been invaluable to me. And, I can say that I have gained a wonderful friend and someone that can truly advocate for me!”

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