1-on-1 AI Coaching for owners with a team.
Advisory coaching from Roving Leads at $150 per 90-minute session for South Bay small business owners and managers. Strategy, tool decisions, team rollout, and accountability – with someone who’s been doing this for a living.
What is 1-on-1 AI coaching?
1-on-1 AI coaching is a recurring 90-minute working session where a small business owner or manager meets with an AI practitioner to make better decisions about AI tools, strategy, and team rollout. At Roving Leads, sessions are $150 per 90-minute session, with no contract.
This is advisory coaching, not implementation. You leave each session with a clearer plan and concrete commitments. Your team – or you – does the actual building between sessions, and we review it together next time. Think of it as having a fractional Head of AI on your bench for an hour a week.
Most Roving Leads coaching clients see meaningful results in 4-6 sessions: prompts shipped, tools chosen, team trained, anxiety down. After that, many drop to biweekly or pause until the next big AI question lands on their desk.
Is 1-on-1 coaching the right fit?
This service is built for owners and managers with at least one other person on the team. If you’re a solo operator, the Solopreneur Coaching page is a different (and better) fit for you.
- You run a team of 2-25, and you’re the one who has to decide what AI looks like for the business.
- Your team is using ChatGPT or Copilot inconsistently and you want to lead, not lag.
- You’ve been pitched AI projects in the $5k-$50k range and you don’t know how to evaluate them.
- You want a regular accountability partner who knows the tools, not a generic business coach.
- You’d rather pay for hours than retainers – and you want to stop or pause without a fight.
- You’re in the South Bay (Redondo Beach, Manhattan Beach, Hermosa Beach, Torrance, El Segundo, Hawthorne, Gardena, Carson) and would prefer to work with someone local – but it’s optional.
1-on-1 vs. Solopreneur coaching.
Same coach, two formats. The honest difference is whether you have a team to delegate to.
1-on-1 Coaching
For owners and managers with a team.
- Strategic advisory – you bring decisions, I bring playbook
- You or your team execute between sessions
- 90-minute sessions, weekly or biweekly
- Most work happens off-screen, in your business
$150per session
Solopreneur Coaching
For solo founders without a team.
- Hands-on – we build prompts and agents together
- You ship something live in every session
- 90-minute sessions, weekly
- Most work happens on-screen, in real time
$300per session
See Solopreneur details ->What 90 minutes actually looks like.
Coaching isn’t a vibe – it’s a structure. Here’s a typical 90-minute session for an advisory client in week 4.
A typical 1-on-1 90-minute session, week 4 of an engagement
What did you actually ship since we last met? What got stuck? Did the prompt I wrote you last week land?
The one decision, deliverable, or build that matters this week. We pressure-test, draft, or sketch a plan together.
I review prompts, agents, vendor proposals, or outputs your team has produced. We kill the bad ones and sharpen the good ones.
How will you brief your team on what we just decided? What does the change-management plan look like? Who needs to know?
Three concrete things you’ll do before our next session. Written down. We’ll start there next time.
After every session you receive a written recap by email – what we covered, what you committed to, and any prompts or files we built together. So you can re-find them in 6 months.
What 4-6 sessions typically changes.
Honest math. Coaching is not magic. Here’s what a typical Roving Leads coaching client ships in their first 4-6 sessions – your mileage will vary based on which problems you bring.
Trained on your voice and templates. Living in a shared library your whole team can re-use.
What to subscribe to, what to cancel, what to wait on. Most clients cancel tools more than they add.
Realistic average across our coaching clients. Some report more, some less. Reported, not promised.
Who learns what, by when. Plus the talking points for your next all-hands AI conversation.
So your team knows what’s OK to feed into AI – and what’s never OK. We sketch this together in session 2 or 3.
The dirty secret. Most owners come in scared. They leave coached. The fear is the actual blocker.
How often we meet, and where.
- Weekly – 90 min – 4-week pack. The default for new clients in their first month. Builds momentum fast.
- Biweekly – 90 min – ongoing. Most clients settle here after month one. Enough room to ship between sessions.
- Monthly – 90 min – check-in. For clients who’ve graduated past active build mode and want a strategic touch-base.
South Bay clients can meet in person at your office, my home office in Redondo Beach, or any local coffee shop. Outside the South Bay, we meet over Zoom – same depth, just less ocean view.
Hours, packs, and what’s included.
Single sessions
Try a session, decide if it’s a fit, then keep going. Same hourly rate either way.
- 90-minute sessions
- Written recap email
- Shared prompt library
- Email Q&A between sessions (reasonable use)
- Pause or cancel any time
4-session pack
The default first-month rhythm. Weekly for 4 weeks, then decide whether to continue.
- Four 90-minute sessions
- Written recaps + shared library
- Direct email/Slack access between sessions
- Fully refundable for unused sessions
- No auto-renew, no contract
Coaching may have you set up paid tools (ChatGPT, Claude, Make, Zapier, etc.). You pay vendors directly – we never mark up software, never collect referral fees, and you keep your accounts even if you stop coaching. No markup. Ever.
South Bay-based. In-person whenever it helps.
Roving Leads coaching is better in person – for South Bay clients, your first session is free in person at your office or a coffee shop you pick, so you can see if the fit is right before booking a pack.
1-on-1 AI Coaching, frequently asked.
How much does 1-on-1 AI coaching cost?
1-on-1 AI coaching from Roving Leads is $150 per 90-minute session, with no contract. A 4-session monthly package is $500 (saving $100). Most clients meet weekly or biweekly.
Who is 1-on-1 coaching for?
Small business owners and managers running a team of 2-25 who want to lead AI adoption strategically – making decisions, picking tools, and coaching their team – without doing the implementation themselves.
If you’re a solo operator without a team, our Solopreneur AI Coaching is built differently and is a better fit.
What does a coaching session cover?
A typical 90-minute session covers: a check-in on what you shipped since last time, today’s main strategic decision or deliverable, a hands-on review of prompts or outputs your team produced, change-management and rollout planning, and concrete commitments before the next session.
Do I have to commit to a contract?
No. All 1-on-1 coaching is month-to-month with no contract. You can pause, cancel, or return any time. Sessions you’ve prepaid but haven’t used are fully refundable.
How is this different from a generic business coach?
Generic business coaches are great for goals, accountability, and mindset. They’re rarely useful for “should I subscribe to ChatGPT Team or Claude Team?” or “is this $1,200/mo AI marketing platform a scam?” That’s where 1-on-1 AI coaching fits – it’s a working AI practitioner with 15 years of marketing experience, not a generalist.
Should I get an assessment before coaching?
Not always. If you already know roughly what you want to do with AI, skip the assessment and go straight to coaching. The assessment is for owners who want a written second opinion before spending money. Coaching is for owners who already know they want to spend money – they just need help spending it well.
Can we meet in person?
Yes for South Bay clients (Redondo Beach, Manhattan Beach, Hermosa Beach, Torrance, El Segundo, Hawthorne, Gardena, Carson) – we’ll meet at your office, mine, or a coffee shop. Outside the South Bay, coaching is over Zoom. Both formats work; in-person is slightly better for the first session.
Can I pause and come back?
Yes. Most clients pause around busy seasons or holidays and come back. Your prompt library and recap docs stay with you the whole time. We pick up where we left off.
Let’s chat
Coaching starts with a free 20-minute chat.
Tell Roving Leads where your team is with AI today. I’ll tell you whether 1-on-1 coaching is the right move – or if something else is.