Coaching & facilitation

We provide coaching and facilitation for individuals and teams, including senior management teams.


Individual coaching contributes to strengthening the client’s toolbox of coping and thriving strategies, better equipping people to show up more fully to themselves, their families, friends and in the workspace. Our role is to build resilience, communication and relationship skills that improve navigating life’s uncertainties, professional roles and the complexities of relationships.

Group and team coaching

Group and team coaching is highly effective for both individuals and organisations. Group coaching creates a rich dynamic space for sharing and reflection as well as an opportunity to practice new skills in a safe, non-judgemental environment. Group and team coaching can help address underlying obstacles or dynamics impeding progress within an organisation.

Complex conversations

We utilise process work, U-theory, Organisation Relationship Systems Coaching (ORSC) and other facilitation skills to give people the opportunity to express and release emotions, hear other voices, and glean wisdom and new insights. These dialogues can surface hidden or unspoken obstacles within communities, organisations and companies and can create an environment for more collaborative solutions to emerge. We design and facilitate processes to support conflict management and to address diversity and inclusion within organisations.

Building a management dream team

Painting Your Wings and associates can help to build and strengthen your non-profit management dream team with our exceptionally skilled coaching and leadership capacity building expertise. We offer team coaching, individual leadership coaching and financial management systems capacity building and coaching.

Frequently asked questions

  • Coping and thriving strategies and tools to better respond to difficult situations and emotions
  • Strategies and tools to break through obstacles to achieving goals
  • More authentic relationships and strengthened support system
  • Develop a plan for the future
  • Accountability


  • Leadership development and organisational effectiveness
  • Acceleration of the pace of change within organisations
  • Better achievement of organisational goals/KPI’s
  • Better application of training to practice
  • Implementation of action plans
  • More effective use of time and resources
  • Improved relationships within the organisation
  • Improved relationships with external stakeholders and partners
  • Increased job satisfaction
  • Individual online or in-person coaching
  • Group/team facilitation and coaching online or in-person
  • Retreats and courses
  • Long and medium-term change process support

Coaching is an ongoing relationship that helps you focus and realise your goals and vision through a creative, thought provoking and inspiring process. A professional coach supports you with the tools to remove obstacles, facilitate change and keep the big picture in mind. Coaching assists you to ensure that how you are spending your time – your daily practices and habits – serve and support your relationships, goals and vision.

Coaching focuses on skills development, strategic planning and personal growth. It improves the quality of life and relationships in the present.  It does not attempt to heal emotional trauma. Coaching can be effective in conjunction with therapy.

What people say

Group and team facilitation

'Well done on taking these dialogues online! It works very well, the facilitators worked well together and did really well with the digital whiteboards and breakout rooms _ very impressive! and great to have a wider, more global group of participants.'

‘This was a very strong and meaningful experience! Thank you for facilitating it!’

‘This was a great dialogue, with expert facilitators who I can learn so much from, thank you.’

‘It felt like a safe space to express myself … I came to a more nuanced understanding of how different and opposing approaches can work together to inform our current and projected realities.’

'Thanks for the meeting and the facilitation. I wouldn't have expected it to work that well online!'

‘This was a very strong and meaningful experience! Thank you for facilitating it!’

‘This was a great dialogue, with expert facilitators who I can learn so much from, thank you.’

Individual coaching

'The coaching experience exceeded my expectations beyond what I ever thought possible... When we first met, I was expecting Jennifer to do a lot more talking and directing. She didn't and I found it a little bit disconcerting. However when I started talking and going further down the coaching process, I was amazed that I actually had the answers to my own questions and that she were merely being the wind in my sails and I was being the rudder.' Client in Cape Town, South Africa
'I have taken a lot of unexpected things from my coaching sessions with Jenny, being one of the most important ones the awareness of my own self and my own strength and value system... Jenny is an excellent coach.' Client in New York, USA

‘My coach really helped me gain awareness for what’s going right in my world. She helped me maintain a positive focus on the good and keep moving forward. Her acknowledgement and recognition of accomplishments and steps forward played a significant role in me seeing them as well. This helped my confidence immensely… Jennifer challenged me to think big picture, recognize my accomplishments, and find ways to meet my goals. I could not have asked for a better coach or better coaching.’ Client in San Diego, USA