E12: Building a Culture of Coaching, Mentoring, and Inclusion

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About Andrea Breen

Andrea Breen is a well-respected leader in the software industry. She is best known for building successful teams and coaching people to achieve their potential. She has had a terrific career across companies like Oracle, Pitney Bowes and is currently the VP of Sales and Customer Service at Objective Corporation.

Building a Culture of Coaching, Mentoring and Inclusion

A leader can make a big difference. They can empower team members, raise the bar and promote inclusivity in the workplace.

That’s what I learned from Andrea, the VP of Sales and Customer Service at Objective Corporation. Aside from her coaching frameworks, she also shared her interesting mentoring stories and wonderful advocacy for diversity and inclusion.

Just like Andrea, you can help empower your team by building a culture of coaching, mentoring, and inclusion in your organisation.

Here are the steps you can take:

1. Coaching: Differentiate between Coaching and Mentoring

Andrea shared that coaching and mentoring mainly differ in their focus on performance measurement. To define the scope, remember that coaching is specific to the performance in the role, while mentoring can cover personal development and relationships.

Despite their differences, both require good listening skills and a strong bond between both parties.

Actionable tips:

1. Practice Active Listening: During a coaching session, refrain from checking your phone or responding to emails, and maintain eye contact with the employee.
2. Set Specific Goals: Help your team members set specific, measurable, achievable, relevant, and time-bound (SMART) goals. If you are coaching a sales representative, work with them to set goals for improvement in the next quarter and agree on the steps they need to take to accomplish it.
3. Constructive Feedback: After observing a team member, look for ways to encourage them with actionable improvements whilst validating strengths and progress.
4. Promote Regular Check-ins: Schedule monthly or bi-weekly virtual meetings to discuss the mentee's progress and provide guidance.

2. Coaching: Set people up for success in their first three months

In the first year of coaching, it is crucial to set people up for success. Andrea shared that this can be achieved by focusing on the team member’s first three months, as it will determine their future success. The first three months are not just about onboarding but also about understanding the team member's strengths. On the other hand, the team member must have the initiative to seek resources and support, rather than be spoon-fed all the time.

1. Focus on Effective Onboarding. Create a structured onboarding program that includes training sessions, introductions to team members and company culture, and clear expectations for their first three months. Assign a mentor or buddy to guide them during this period, helping them understand team dynamics and company processes.
2. Conduct Regular Check-ins and Observations. In the first three months, observe their interactions with team members and clients. Share with them where their strengths and weaknesses lie. After that, schedule regular check-ins with new team members to track their progress.
3. Encourage Proactive Resource Seeking. Encourage new team members to reach out to experienced colleagues or department heads to seek guidance and support for their growth.

3. Coaching: Create a one-on-one coaching framework

Andrea’s coaching framework involves a structured one-on-one meeting every week. This meeting is not a forecast call, but rather a conversation about the team member’s blockages, aspirations, and career path. While this approach is not widely used, it’s effective because it allows the leader to raise concerns and celebrate small successes along the way. The meeting must also be structured, with the leader taking notes and following up with the team.

Actionable tips

1. Schedule Structured Weekly One-on-One Meetings. Block out dedicated time each week for one-on-one sessions. During these meetings, discuss their recent achievements and roadblocks. Use this time to identify opportunities for growth and address concerns.
2. Use the Meeting to Celebrate Successes and Address Challenges. During a weekly meeting, acknowledge their successful completion of a challenging sales deal or their efforts in resolving a customer issue effectively. Celebrate these accomplishments to reinforce positive behaviour and motivate further success. Simultaneously, address any struggles and provide resources to overcome them.
3. Take Notes and Follow Up. After each meeting, summarise the main takeaways and action steps in a shared document or CRM system. Follow up with the team member to check on their progress and hold them accountable for commitments made during the previous session.

4. Coaching: Practice a note-taking habit in meetings

Andrea, a prolific note-taker, has kept notes from every meeting she's had in the last seven years at Objective. This allows her to quickly review the discussions and actions, ensuring that no one forgets important information. This habit helps maintain a record of important conversations and ensures that everyone is aware of their contributions.

Actionable tips:

1. Use Digital Tools and Organisation Apps. Use apps like Evernote, Microsoft OneNote, or Google Keep to create digital notebooks for different projects, team members, or meetings. Organise notes into categories, tags, or folders to find information quickly.
2. Actively Listen and Summarise Key Points. While engaging in a sales call or team meeting, focus on listening attentively to clients or team members. Summarise the main takeaways and key action items in your notes, avoiding unnecessary details.
3. Use Abbreviations and Keywords. Develop a list of standard abbreviations for common terms or phrases used in sales meetings or presentations. Use these abbreviations to jot down notes quickly without missing essential information.

5. Coaching: Get to the bottom of problems

In a coaching conversation, it's common to feel misled or not getting the whole picture. As a sales leader, Andrea believes it's essential to have a good radar and continue probing. If the conversation isn't getting anywhere, it's okay to leave it. The passage of time allows for a fresh approach and reflection. However, sales leaders should be aware that everything is not what it seems. Decisions are made based on information passed through someone else's filter.

Actionable tips:

1. Practice Root Cause Analysis. When facing declining sales numbers, conduct root cause analysis by asking "why" multiple times to uncover deeper issues. For instance, if sales are down, the question might be: "Why are sales down?" - "Because leads have decreased." - "Why have leads decreased?" - "Because marketing efforts have shifted." Continue until you identify the core issue and address it.
2. Seek Diverse Perspectives. Let team members can share their thoughts and ideas on potential performance challenges. Consider different viewpoints to develop a well-rounded understanding of the problem.
3. Develop Hypotheses and Test Solutions. If the team is struggling with converting leads into sales, develop a hypothesis such as "Providing additional sales training may improve conversion rates." Test this hypothesis with a subset of the team, evaluate the results, and then decide on the best course of action.

6. Coaching: Avoid compensating for underperformers

In coaching, it is crucial to be intuitive and listen to understand the needs of the team. Andrea shared that one of the mistakes that leaders make is compensating underperformers, which can lead to the team member feeling frustrated and unsupported. Leaders should also be aware of the team member’s responsibilities and provide them with the tools and space to perform their roles effectively.

Actionable tips:

1. Learn Nonverbal Cues. Since not all people are outspoken, you can observe their body language and facial expressions during meetings to get clues about how they’re feeling. Additionally, ask open-ended questions to encourage them to share their concerns. By listening intently, you can identify their needs and tailor your coaching approach accordingly.
2. Foster a Culture of Accountability and Reward. Set up performance-based incentives and recognition programs within your team. Reward team members who consistently meet their targets with bonuses or public acknowledgment. Meanwhile,
3. Set Clear Expectations and Provide Necessary Tools. At the beginning of a new project, clarify their individual responsibilities and provide access to training, software, or support that will aid their performance. When team members are well-equipped, they are more likely to feel supported and confident in achieving success.

7. Coaching: Help people feel like they’re doing something significant

I observed that while achieving career success is great, many people don’t feel satisfied with it. They only feel they’re doing something significant when they’re helping others. That’s why Andrea suggests that if you’re in a senior role and want to achieve genuine fulfilment, carve out time for mentoring others. Mentoring can help you feel fulfilled, as it’s a two-way engagement where both mentor and mentee benefit.

1. Encourage Customer-Centric Selling. During team meetings, share success stories of team members who went above and beyond to help a customer overcome a specific problem. Highlight how their efforts not only resulted in a successful sale but also made a positive impact on the customer's business or life.
2. Encourage Community Involvement and Giving Back. Organise a team volunteer day at a local nonprofit organisation where your team can contribute their time and skills to support a meaningful cause. Engaging in community service together fosters a sense of fulfilment and camaraderie among team members.
3. Recognise and Celebrate Acts of Helping Others. Implement a recognition program where team members can nominate their peers for "Helping Hand" awards. Celebrate those who consistently demonstrate a willingness to support others and make a positive impact on their colleagues' success.

8. Mentoring: Define the scope of your relationship

Whether you’re mentoring someone, defining the scope of your relationship is crucial to achieving both parties’ desired outcomes. The mentor sets the guardrails of the relationship, and the mentee defines the scope. It is not a performance-oriented relationship.

Actionable tips:

1. Initial Meeting and Goal Setting: Schedule an initial meeting to discuss your respective expectations and objectives for your mentoring relationship. Ask about your mentee’s career aspirations and specific goals. You, on the other hand, can talk about your expertise and the kind of support your can offer.
2. Outline your Mentoring Relationship. Discuss meeting frequency, responsibilities, and confidentiality. Ensure that both parties feel comfortable sharing and receiving feedback and are aware of the limits of their professional relationship.
3. Evaluate the Experience. Reflect on the successes, challenges, and key takeaways from the mentoring journey. If you both find value in continuing the relationship, you can discuss the possibility of extending or redefining the scope.

9. Mentoring: Make sure you’re compatible with your mentee

Compatibility is also essential in coaching and mentoring. Andrea shared that organisations play a critical role in matching mentors through professional development cycles, check-ins, and performance reviews. At Objective, they aim to make matches where possible. For instance, Andrea endeavours to match people up with senior managers in the business to get the right fit.

Actionable tips

1. Do a Trial Period. Start the mentoring relationship with a trial period of a few sessions. During this time, pay close attention to how you interact. Assess whether you both feel comfortable and open to sharing thoughts and ideas.
2. Assess Shared Goals and Interests. Discuss your mentee's career goals and interests to see if they align with your expertise and experience. If there is a match, it will likely lead to a more fulfilling partnership. However, if there are areas outside your expertise, be transparent about them and consider whether you can still offer valuable guidance in other aspects.
3. Create Mentor-Matching Processes. Your HR team could develop a mentorship-matching questionnaire to gather relevant information about potential mentors and mentees. This data can then be used to create better matches and improve the overall success of mentoring relationships.

10. Mentoring: Mentor team members in the early stages of their career

Andrea shared that managers should identify someone on their team who would benefit from mentorship at their peer level and then initiate the relationship. This approach can be challenging, as it may not be suitable for everyone. However, it is crucial to match the mentee based on their motivation and readiness to find a mentor. During this stage, it’s also crucial for the mentee to be authentic and open-minded.

Actionable tips

1. Ensure Willingness on the Mentee’s Part. Confirm that the mentee is motivated and ready for mentorship. Have a candid conversation with the mentee to understand their expectations and commitment to the mentorship. Simultaneously, consider potential mentors within the organisation who have experience and expertise relevant to the mentee's goals.
2. Establish Trust and Rapport. At the beginning of the mentorship, openly discuss confidentiality and reassure the mentee that their discussions will remain private, encouraging them to be open and honest.
3. Provide Guidance and Resources: Offer actionable advice and share relevant resources that can help the mentee progress in their career. For example, they can read my book, Switch: Stand Out, Get the Right Job and Accelerate Your Career. I wrote this book to help people land the jobs they truly love and use clarity in making a difference.

11. Mentoring: Create an environment that encourages mentorship

Andrea shared that many senior leaders do not prioritise mentoring, which can be a problem. This shouldn’t be the standard because mentoring new talent within the organisation can be the key to the future. This is why leaders need to start creating an environment conducive to mentoring. Andrea believes you can achieve this through structured mentoring programs, which can be beneficial for all-size organisations.

Actionable tips

1. Implement Structured Mentoring Programs. Match senior leaders or experienced employees to junior employees who express their interest in being mentees. The program can include regular mentoring sessions and opportunities for mentees to seek guidance on specific challenges they are facing.
2. Lead by Example. Make yourself available as a mentor to junior employees. Share your experiences, offer insights, and provide guidance on career development during mentoring sessions.
3. Foster a Culture of Learning and Growth. Encourage employees to share knowledge and experiences with one another through internal networking events or lunch-and-learn sessions.

12. Mentoring: Reassure mentees that it’s okay to reach out

Andrea shared that companies should foster an environment where managers are willing to share time and mentees feel comfortable reaching out for mentorship. For example, community managers can establish a framework for goal-setting and match the mentee with a mentor. With this kind of streamlined and structured approach, mentees will feel more reassured in building a relationship with their mentor.

1. Promote Psychological Safety. Verbally communicate to your team members that it’s never wrong to express their thoughts or feelings in meetings or one-on-one sessions. Show appreciation for those who seek guidance and openly discuss the challenges they face.
2. Establish an Open Communication Culture. Conduct regular team meetings or virtual town halls where senior leaders emphasise the importance of mentorship and actively invite mentees to share their concerns.
3. Communicate the Importance of Mentorship. Highlight the value of mentorship during onboarding and orientation sessions for new employees. Include mentorship success stories in company newsletters or share testimonials from mentees who have experienced positive outcomes from their mentoring relationships.

13. Diversity: Support women in technology and gender diversity

Andrea is a strong supporter of women in technology and gender diversity. She believes that the talent pool is missing out on many amazing women in tech. However, there are organisations like Women in ICT, which started in ACT, which are championing this cause. Andrea has been a speaker at one of their breakfast events and advises both men and women to support these organisations.

She also encourages using inclusive language in meetings and celebrating the success of women in their organisations. A diverse organisation is better, as evidenced by the statistics. By supporting these organisations, you, as a leader, can help create a more inclusive environment for all members of the tech industry.

1. Support and Collaborate with Diversity Organisations. As a sales leader, collaborate with Women in ICT by sponsoring their events, providing guest speakers from your team, or offering mentorship programs for aspiring women in tech.
2. Use Inclusive Language. During team meetings, remind team members to avoid using pronouns that assume specific gender identities. Encourage using phrases like "everyone," "team members," or "colleagues" instead of gender-specific terms. In written communication, ensure job postings and company materials use inclusive language to attract diverse talent.
3. Celebrate the Success of Women. Hold regular recognition events, such as a "Women in Tech Excellence Awards" ceremony. Highlight success stories of women in the organisation on social media or in company newsletters to promote role models for aspiring tech professionals.

14. Diversity: Help your women break out of their limitations

Andrea acknowledged this misconception that women need to be tough or unemotional to succeed in tech, to which she strongly disagrees. She emphasised that while working in tech is challenging, women shouldn’t suppress their emotional authenticity in order to move forward in their careers. Andrea believes that more leaders should step up to address this gender bias issue.

1. Embrace Authenticity and Emotional Expression. As a sales leader, lead by example by being open about your own emotions in appropriate contexts. Share your feelings about challenges and struggles with your team to show that authenticity is a valued trait in the workplace.
2. Challenge Gender Biases and Perceptions. When you encounter biased statements or perceptions about women in tech being perceived as "tough" or "hard," address them directly during meetings or discussions. Educate your colleagues about the importance of diversity to create a more inclusive and supportive work environment.
3. Promote Women's Leadership Visibility. Work with HR or event organisers to ensure that women leaders are given opportunities to present at conferences, webinars, and internal meetings. Host panel discussions that feature successful women in tech.

Final thoughts

I learned from my conversation with Andrea that coaching and mentoring do not only boost an organisation’s morale and productivity. Building a culture of coaching, mentoring, and diversity also helps an individual feel genuinely fulfilled. By helping others become their best versions, we also become better ourselves.

About Andrea Breen

Andrea Breen is a well-respected leader in the software industry. She is best known for building successful teams and coaching people to achieve their potential. She has had a terrific career across companies like Oracle, Pitney Bowes and is currently the VP of Sales and Customer Service at Objective Corporation.

About Pree Sarkar

Pree Sarkar is an Executive Recruiter and Talent Advisor to leaders at start-up and global technology companies. He is the Founder and Chief Advisor at Switch Recruitment, a leading firm in the Asia Pacific Region.

LinkedIn rated him as a Top 1% Recruiter and he is also the #1 Best Selling Author for his book – Switch, Stand Out, Get Noticed and Accelerate your career.

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