Toby Sinclair

Work with me

Your AI strategy will live or die in conversations the slide deck never mentions.

I work with enterprises on the human side of AI — training the teams who need to use it, coaching the leaders who need to lead it, and building the practice habits that make change stick. Here's how.

Book a discovery call →

How to choose

Three ways in, one thread through all of them: practice over theory.

Not sure which? That's what the discovery call is for. No pitch, just a working conversation about where you are.

01 — AI Enablement Training

From “we should use AI” to actually using it well.

Most AI training is a demo with a Q&A bolted on.

People nod. People leave. Nothing changes.

My sessions are working sessions. Your teams bring their real work — the reports they write, the candidates they screen, the data they wrestle with — and leave having done something with AI, not just watched someone else do it.

What we cover (shaped to your function)

Finding the real use cases

Mapping AI against your actual workflows, and being honest about where it doesn't belong

Hands-on practice

Prompting, judgement, and quality control with the tools your organisation actually uses

The opportunity mindset

Using AI to generate value and credibility, not just cut cost

Human-in-the-loop judgement

Where people must stay in control, especially in regulated and people-sensitive work

Formats

Half-day working session

One team, one function, hands-on from minute ten

Full-day intensive

Deeper practice plus a use-case roadmap the team owns

Programme

A series of sessions across functions, building capability that compounds

WPP

Recent example. I ran a session with WPP's HR and talent leaders on leading AI adoption across recruitment, employee engagement, and people analytics — reframing AI as an opportunity engine for the function, not a cost-saving exercise. Read the case study →

Who it's for

Leadership teams, HR and talent functions, L&D leaders, and any function rolling out AI that needs more than a webinar.

Book a training conversation →

02 — Coaching Through AI Change

The change programme has a plan. Your leaders have a knot in their stomach.

AI transformation is the hardest change most leaders will ever run. It touches identity, not just process. And the manager in the middle has to hold that conversation with no script.

This is where a decade of coaching meets daily life inside an AI company.

People aren't resisting the tool — they're asking what it means for them.

What coaching looks like

One-to-one coaching

For senior managers leading AI change — the thinking space to work through resistance, restructuring, and their own relationship with the technology

Team coaching

For exec and leadership teams — getting honest about where the organisation really is, and aligning on the change story people will actually believe

The conversations themselves

Preparing leaders for the specific discussions AI forces: redefined roles, new expectations, anxious teams, sceptical high-performers

I'm an ICF Professional Certified Coach. The craft is listening, asking, and helping people find their own next move — not adding another layer of advice. Pointed at AI change, it's the difference between a transformation people comply with and one they commit to.

Engagement shapes

Leader coaching

Typically 6 sessions over 3–6 months

Exec team coaching

Facilitated sessions alongside your transformation milestones

Coaching + training combined

Many clients pair a team training session with follow-up coaching for the leaders carrying the change

Who it's for

Senior managers, exec teams, transformation leads, and the people everyone else is watching to see how to feel about AI.

Explore coaching →

03 — Real Talk Studio

Knowing what to say is the theory test. Saying it under pressure is the driving test.

Real Talk Studio is the company I founded. Teams rehearse feedback, conflict, and high-stakes conversations with AI characters — before they happen for real — and get behavioural evidence of competence, not just a completion certificate.

It's also why my training and coaching aren't secondhand. I design with large language models every day. I know where AI genuinely helps, where it quietly fails, and what it takes to get an organisation actually using it — because I live it.

Training builds the skill. Coaching builds the leader. Real Talk Studio proves the competence — at scale, with data.

Many engagements start with a session or coaching and grow into the platform when the organisation wants practice embedded, not occasional.

Visit Real Talk Studio →

Why this combination works

Built with AI. Grounded in people. Tested in demanding rooms.

01

I build an AI company daily

So the training is informed by shipping real product, not conference slides

02

I've coached leaders for a decade

So the change work goes deeper than adoption metrics

03

I spent ten years at JP Morgan

So I know what regulated, high-pressure environments will and won't tolerate

You don't need another AI keynote. You need someone who can sit with your people and make it real.

How engagements start

One conversation. Then the work.

01

Discovery call (30 min, free)

You describe where you are; I tell you honestly whether and how I can help

02

Proposal

A short, plain-English outline of the work, shaped to your context

03

The work

Training, coaching, or both; in person or remote

04

What's next

Every engagement ends with a clear view of what your organisation should do without me

A 30-minute discovery call. No pitch — just a working conversation.

Book a discovery call →

FAQ

Common questions

Do you only work with large enterprises?+

No. Most of my work is with enterprise functions and leadership teams, but the sessions scale down well — the smallest useful unit is one leadership team.

Which AI tools do you train on?+

Whatever your organisation actually uses. The judgement and habits transfer; I'm tool-agnostic by design.

In person or remote?+

Both. I'm based in the UK and run sessions in person across the UK and remotely worldwide.

Are you selling Real Talk Studio in these sessions?+

No. Training and coaching stand on their own. Some clients later adopt the platform; many don't. I'll always tell you which I think fits.

What's the first step?+

A 30-minute discovery call. Book it here →