Richard Black

Executive Coach for Senior Caribbean Leaders | Helping leaders recognise and shift the patterns pressure creates so they can make clearer calls, build greater ownership, and have more space to lead.

About

I work with senior Caribbean leaders who have done well, earned trust and taken on bigger roles, only to find that some of the ways they have always led are no longer working quite as well.

Pressure has a lot to do with it.

It can make you carry too much, stay too close to the detail, over-prepare, avoid a difficult conversation or feel that you still have something to prove.

It can also affect the way you work with people. You may step in too quickly, find it harder to trust others with important decisions, or become more guarded when a relationship is under strain.

My work helps leaders recognise these patterns and change the ones that are getting in the way.

Sometimes that means leaving a decision where it belongs instead of taking it back. Sometimes it means having the conversation you have been putting off. Or recognising that something you have always been good at is now taking up more of your attention than it should.

I bring more than 40 years of leadership experience across oil and gas, software, financial services and organisational transformation. I have led businesses, large teams and regional operations across Europe, Africa and the Caribbean.

At one point, I was leading across 15 countries. I learned that I could not personally carry every issue or make every important decision.

I also learned to ask myself a harder question when something was not working:

What was I contributing to it?

That question still shapes how I work with leaders today.

I understand the pressure from inside the role: making difficult calls without having all the information, working across competing interests and knowing when to step in and when to leave something with someone else.

Coaching gives us a place to look closely at what happens when the pressure rises, where your own response may be making things harder, and what you could do differently.

The result is not a new leadership formula. It is a clearer sense of what the role needs from you now, what you need to let go of, and where your attention is best spent.

Packages

Free Discovery Call

A confidential first conversation to help you get clear on what feels heavy, what may need to shift, and what support may help.
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Leadership Reset - Private 1:1 Coaching

A focused six-session coaching package for senior Caribbean leaders who want clearer thinking, steadier judgment, and practical support with a leadership issue that needs attention.
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Leadership Partner - Private 1:1 Coaching

A longer-term coaching partnership for senior Caribbean leaders who want sustained support through complexity, pressure, and higher-stakes leadership challenges.
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For Organisations - Executive Team and Leadership Development

Helping organisations strengthen executive judgement, alignment, and accountability when pressure begins to affect how senior leaders and executive teams perform.
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For Organisations - Leadership Performance Accelerator

A 9 to 12 month leadership development programme for organisations that want senior leaders to perform with more consistency, confidence, and clarity under pressure.
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When Executive Coaching Makes Business Sense for Senior Caribbean Leaders

Digital Download
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Testimonials

Fernandes Group valued Richard Black’s practical, hands-on coaching style and his ability to create space for meaningful senior-leadership reflection while keeping the work grounded in real decisions, pressures, and priorities.

His senior executive experience and structured sponsor check-ins helped keep the engagement aligned while respecting the privacy of the coaching relationship.

- Fernandes Group

Working with Richard came at a time of intense pressure, including a company acquisition and the impact of a devastating hurricane on the business.

Coaching helped me shift from feeling caught in the circumstances to taking charge of my own space and actions. I reconnected with my strengths, restored my confidence, and began showing up more consistently as a leader.

Richard’s calm presence, careful listening, practical tools, and genuine follow-up made a real difference. He is credible, effective, and reliable, and I would recommend him and work with him again.

- K. Smith, General Manager

Richard helped me recognise strengths that I had overlooked, giving me the confidence to pursue opportunities I might previously have ignored.

His coaching challenged my thinking, broadened my perspective, and helped me lead with greater confidence.

I trusted my team more, navigated a difficult business environment with greater clarity, and became a stronger leader both at work and at home.

- Denise Chinpire O’Reilly, Chief Executive Officer

Richard helped me move from acting as a ‘referee’ between managers to creating clearer accountability and stronger ownership across my leadership team.

The coaching helped me become more strategic, more decisive, and more consistent in how I lead.

- Patrick Pengel, Managing Director

Working with Richard helped me become more pragmatic in my approach to leadership, improve my decision-making, and strengthen my results orientation. His coaching helped me recognise blind spots, organise my thinking around difficult issues, and stay accountable for the actions I committed to. The structured conversations gave me greater clarity at work and more peace of mind outside work.

- Alvin Venetiaan, Managing Director

Richard helped me become more aware of how I was showing up under pressure. I learned to recognise what was happening, regulate my response, and make more conscious choices rather than reacting emotionally. His questions consistently uncovered the real issues beneath the surface, leading to greater consistency in my leadership, improved wellbeing, and more presence in my personal life.

- Sana Ragbir, Group Deputy CEO

I began coaching with Richard feeling skeptical after a previous coaching experience produced little value. He helped me challenge long-standing patterns, understand what was driving my behaviour, and build new habits. I have seen the impact in both my leadership and my personal relationships.

- Managing Director, Corporate Services

As I moved from business ownership into a new leadership role, the coaching helped me clarify my direction, recognise strengths I had been overlooking, and stay accountable for the goals that mattered most.

I became more confident in my leadership, managed competing priorities more effectively, and approached both my career and personal goals with greater focus and perspective.

- Executive Management, Energy Sector

Working with Richard helped me become more reflective, disciplined, and intentional in how I lead.

The coaching supported me in improving delegation, setting clearer boundaries, saying no without guilt, and creating more space for my direct reports to contribute. I became more aware of my patterns and better able to choose my response rather than simply react.

Richard’s approach felt safe, practical, and tailored. His conversational tone, lack of judgement, and relevant guidance helped me find my own answers and convert awareness into action.

- AVP, Financial Services

Free Discovery Call

Let's have a friendly chat over a virtual coffee and discover if we're a fit.

Frequently Asked Questions

What kind of leaders do you work with?
I work mainly with senior Caribbean leaders, usually Directors, VPs, GMs, senior functional heads, and C-suite leaders. Most are respected, capable, and trusted, but are finding that the habits that helped them succeed earlier are no longer enough for the role they are in now.
What do leaders usually bring to coaching?
Usually pressure, role stretch, difficult relationships, team dependency, board or stakeholder tension, decision fatigue, or the sense that too much still runs through them. Sometimes the issue looks operational on the surface, but underneath it is about how they are showing up under pressure.
What is coaching with you actually like?
Practical. Confidential. Direct. We focus on what is happening in your real leadership context. I listen carefully, ask questions, challenge where needed, and help you think more clearly about what is driving the issue and what needs to change. This is grounded work, not generic coaching talk.
Is coaching the same as therapy?
No. Coaching is not therapy. Therapy deals with areas that require specialist clinical expertise. Coaching is a structured conversation process that helps you think more clearly, understand your leadership patterns, and take better next steps in the real world.
Do you give advice, or is this only coaching?
The work is coaching-led. The main focus is helping you think, decide, and act more effectively for yourself. Where useful and appropriate, I may also offer perspective, share an observation, or help you frame a difficult leadership move. I do not position the work as one-size-fits-all advice.
How long does the process usually last?
That depends on the level of support you need. Some leaders start with a focused three-month engagement around one specific issue. Others need a longer-term partnership over six months or more. We talk about that at the start and agree the right scope.
How often do we meet?
Most sessions are 60 minutes. They are usually spaced every two to three weeks, depending on the package and the period you are in.
Is everything confidential?
Yes. Coaching is confidential by default, within normal legal and ethical limits. I also take extra care with confidentiality in small-society environments, where anonymity and discretion matter even more.
What kind of results can I expect?
I do not make guarantees. What I can say is that leaders often leave with clearer thinking, better judgment under pressure, stronger boundaries, cleaner conversations, and a more effective way of leading at the level their role now requires.
How do I know if I am a good fit for this work?
A good fit is someone who is open to honest reflection, willing to look at patterns, and ready to take responsibility for change. You do not need to have everything figured out, but you do need to be willing to do the work.
What happens in the first call?
The first call is a confidential conversation. You bring what feels most important. I will ask questions, help you get clearer on what is happening, and explain how I work. If I believe I am the right fit, I will say so. If not, I will say that clearly too.
Do you work with organisations as well as individuals?
Yes. I work with individual leaders directly, and I also work with organisations or HR leaders who want coaching support for a senior leader or leadership team. In those cases, scope, boundaries, confidentiality, and communication are agreed clearly at the start.
Can sessions be rescheduled?
Yes, with notice. The rescheduling terms are confirmed in the coaching agreement before the work begins.
Do you offer in-person or virtual coaching?
Most coaching can be done virtually. In-person sessions may be possible depending on location and circumstances.
What if I am not sure I need coaching yet?
That is fine. Many leaders start there. Sometimes the first step is simply a conversation to make sense of what feels heavy and decide whether coaching would be useful.
Are you a certified coach?
Yes, I am an Associate Certified Coach (ACC) with the International Coaching Federation (ICF) and Certified Professional Coach through the Institute for Professional Excellence in Coaching (iPEC) with a speciality in Executive Coaching & Leadership Development.

What ethical standards guide your coaching practice?
My coaching practice is guided by the International Coaching Federation Code of Ethics, including confidentiality, transparency, professional integrity, and respect for the client relationship. Clients can review the ICF Code of Ethics and related ethics resources through the International Coaching Federation website. ICF also provides an Ethical Conduct Review process for concerns involving ICF members or credential-holders. Link to relevant ICF website: https://coachingfederation.org/credentialing/coaching-ethics/icf-ethical-resources/

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