Raido Kivikangur
Executive decision coach | Strategic thinking partner | Former CTO

If any of this feels relevant to your current leadership situation, book a free 45-minute introductory conversation.
We will take time to understand what is happening, where things may be getting stuck, and whether leadership coaching, management diagnostics or strategic thinking partnership could be a useful next step for you or your organization.
About me
There are moments in leadership when things get stuck. Decisions slow down. Responsibility becomes unclear. The strategy exists, but does not show up in daily work. The team works hard, yet results do not move at the same pace, and more and more decisions start coming back to the leader.
This does not usually mean that something is broken. More often, focus, roles or the rhythm of collaboration have become unclear. And that can be changed.
I help leaders and leadership teams restore clarity in decisions, responsibility, collaboration and execution.
I work with leaders facing complex decisions, role transitions, growth pressure or situations where they have become a bottleneck in the organization.
My work combines leadership coaching, strategic thinking partnership and management diagnostics. Every engagement starts with understanding the situation. Only then do we decide whether the right next step is individual coaching, leadership team diagnostics, strategic thinking partnership or a combination of these.
Who I am
I have held C-level leadership roles, including CTO, in the infrastructure and energy sectors. I have led international programmes worth more than 3 billion euros across the Baltics, Poland, Sweden, Finland and the UAE. I have completed international coaching training at the Academy of Executive Coaching in London and have delivered approximately 750 hours of coaching.
I do not look at leadership only as theory. I know what it means to make decisions under pressure, with incomplete information, multiple stakeholders and real business consequences. I combine that practical leadership experience with a professional coaching approach.
I have also experienced burnout myself. I know what it means to give more than is sustainable in the long run. That is why one question is always present in my work: how can you make good decisions in a way that leaves enough strength for tomorrow?
How I work
I do not come in to give ready-made answers. My role is to help you see the situation more clearly, separate what matters from the noise, make stronger decisions and turn them into concrete steps with clear ownership, rhythm and follow-through.
When working with organizations, I also use Clarity Compass when relevant. It is a management diagnostic tool that helps identify where strategy, roles, priorities and responsibility actually get stuck in daily work.
Contact me if:
- you are in a new or larger leadership role;
- you are leading a complex change or strategic programme;
- your team works hard, but results are not moving at the same pace;
- decisions and responsibility too often come back to you;
- there are too many priorities and focus is getting lost;
- the leadership team needs an honest picture of where execution is getting stuck;
- you are facing a difficult conversation, conflict or decisive leadership moment;
- you need a thinking partner who understands people, systems and high-stakes decisions.
If there are too many issues on the table at once, priorities are unclear, decisions are slow, responsibility is blurred and you feel that you are carrying it all alone, get in touch.
Sustainable leadership
Raido helped me become a better leader. He helped me understand my boundaries, how to recover in a demanding role and how to handle people-management challenges more professionally. His style is supportive, attentive and genuinely caring. Every manager should have at least a few sessions with Raido.
Kelly Treu
Marketing & Communication Professional, Volkswagen
Present, trusted and direct
Raido is present, listens deeply and asks the kind of questions that help you grow as a leader and as a person. His long leadership career and ability to connect with people make him a rare combination of practical executive experience and strong coaching presence.
Annika Pajupuu
Marketing & Sales Executive
Trust, focus and clarity
Raido creates trust and psychological safety very quickly. As a coach, he is calm, present, solution-focused and empathetic. He helps bring real topics to the surface, keeps the goal in focus and supports the client in seeing the bigger picture, focusing on what truly matters and moving forward with clarity.
Reelika Ojakivi
Executive Coach, Trainer
Clear goals, real progress
“Having worked with Raido for nearly half a year by now, I can see that it has had a significant impact on both my personal and career development. Raido has helped me to specify my goals and decipher different solutions to problems. His positive attitude and skillful coaching have given me tremendous added value both at work and at home.”
Martin Teder
Estonian Police and Border Guard Board, group leader
Deep connection, real change
As a host who engages with top coaches globally, I rarely encounter someone who truly redefines the client-coach experience. Raido Kivikangur’s wisdom and unique coaching approach are transformative. His ability to connect on a profound level and his remarkable vision make him an outstanding guide for anyone seeking real change. I highly recommend Raido as a coach and thought leader.
Joshua T. Beglan
Creator of the World's Mayor Experience OmniMedia Platform
Support, challenge and action
Raido combines support with the right level of challenge. He does not give ready-made answers or take responsibility away from the client. Instead, he helps keep the focus clear, see the next steps and move into action. I especially valued the way he adapted to my pace while still keeping the goal firmly in sight.
Kaie Sassi
Founder and Owner, OÜ Taimest

