Freelance Critical Friend

Do it Now Now (DiNN) is looking for empathetic, insightful, and experienced individuals to join our programmes as Critical Friends. A Critical Friend is a trusted advisor and mentor who provides honest, constructive feedback while fostering a supportive and empowering environment.

In this role, you will act as a sounding board for programme participants, helping them critically evaluate their ideas, reflect on their progress, and develop practical solutions to challenges. Your role is not to direct or dictate but to guide participants towards greater clarity, confidence, and capability in their entrepreneurial and leadership journeys.

Critical Friends play a pivotal role in our programmes by building trust-based relationships with participants, supporting their growth as changemakers and leaders, and ensuring they feel equipped to overcome obstacles and pursue their goals effectively. You will work collaboratively with both participants and programme teams to deliver meaningful, tailored support.

If you are passionate about empowering others, skilled in providing constructive feedback, and committed to fostering equity and inclusion, this is an opportunity to make a lasting impact on individuals and communities.

Key Responsibilities

1. Individual Mentoring and Support:

• Conduct one-to-one sessions with assigned participants, offering personalised guidance and support.

• Assist participants in developing and refining their action plans during Diagnostics sessions.

• Provide constructive feedback that encourages self-reflection, confidence-building, and practical problem-solving.

2. Programme Engagement:

• Attend cohort training sessions to gain a deeper understanding of participants’ goals, challenges, and progress.

• Support participants in preparing for critical milestones in their programme journey.

• Facilitate connections between participants and relevant resources, tools, or networks.

3. Collaboration and Continuous Learning:

• Participate in monthly reflective meetings with programme facilitators and other Critical Friends to share insights, challenges, and solutions.

• Work closely with the programme team to address participant needs, adapting support as required.

• Contribute to monitoring, evaluation, and learning (MEL) activities by providing detailed feedback on participant growth and outcomes.

Essential Skills and Experience

• Proven Mentorship Experience: Demonstrated success in mentoring, coaching, or advising individuals in professional, entrepreneurial, or social impact contexts.

• Strong Interpersonal Skills: Ability to build trust and rapport with diverse participants, creating a safe and empowering environment.

• Constructive Feedback: Skilled at providing actionable, reflective feedback that drives growth and confidence.

• Sector Knowledge: Understanding of the challenges faced by grassroots organisations, early-stage changemakers, or social enterprises.

• Equity and Inclusion: Commitment to strengths-based capacity building and principles of equity and inclusion.

Desirable Qualifications and Experience

• Experience supporting marginalised or underrepresented communities.

• Knowledge of the social enterprise or non-profit sectors, including their unique challenges and opportunities.

• Background in coaching, advisory, or leadership roles within start-ups, social innovation, or similar fields.

• Familiarity with monitoring, evaluation, and learning (MEL) frameworks.

• Previous involvement in professional development or leadership programmes.

Key Attributes

• Empathetic and Approachable: Demonstrates genuine interest in participant success and well-being.

• Insightful and Analytical: Skilled at identifying barriers and opportunities for participant growth.

• Adaptable and Flexible: Responsive to evolving participant needs and programme requirements.

• Self-Motivated: Able to work independently while contributing meaningfully to a collaborative team environment.

What We Offer

• A meaningful opportunity to contribute to systemic change and community empowerment.

• Collaboration with a dynamic, mission-driven team.

• Flexibility to work remotely and independently, with occasional opportunities for in-person engagement.

How to Apply

Please send your CV, a cover letter detailing your relevant experience and why you are interested in this role. Applications will be reviewed on a rolling basis.

Disclaimer

This role is offered on a freelance basis and is outside the scope of IR35 regulations. The successful candidate will be engaged as an independent contractor and will not be considered an employee or worker of Do it Now Now (DiNN). Consequently, no employment rights or benefits, such as holiday pay, sick leave, pensions, or other entitlements associated with employment, will be provided. The freelancer will retain responsibility for their own tax obligations, National Insurance contributions, and compliance with relevant laws and regulations as per their independent contractor status.

DiNN will not direct or control how the freelancer delivers their work, beyond agreeing on the required outcomes, ensuring alignment with the terms of the contract and project objectives. This relationship is strictly that of a service provider and client.