The questions partners actually ask, with honest answers.

Everyone's talking about AI. We don't know where to start. What should we actually do first?

You don't need an AI strategy deck. You need to know which two or three repetitive things your team does every week that AI can take off their plate, and which ones it can't do safely yet.

Start with a two-week AI Opportunity Audit that identifies the highest-value workflow candidates and gives you a plan with priorities. Then pick one and either take it forward yourself or build it together with us. The deliverable is a plain-English document, not a 200-page slide deck.

See the full answer on the Services page →

We've tried ChatGPT casually but it hasn't turned into anything useful. How do we get from playing around to real time savings?

Casual usage is a different muscle than everyday use. ChatGPT in someone's browser tab is helpful for one-off questions, but it never turns into real hours saved unless you wire it into the work itself: your customer database, your inbox, your document tools, your reports.

The bridge is the AI Opportunity Audit: we look at what you've already tried, find which experiments could become repeatable workflows, and pick one concrete first build. That's the difference between "we use ChatGPT sometimes" and "the Monday morning report writes itself now."

Engagements: AI Opportunity Audit · $2,500 · 2 weeks.

Our team spends hours every week on the same repeatable tasks. Can AI realistically take some of that off our plate, safely?

Yes. The work I've seen the highest return on for Canadian small businesses: proposal/quote drafting, internal knowledge search, meeting summaries with auto-updated customer list entries, inbox sorting with quick first replies, and recurring reports that build themselves. Every piece of work includes five safeguards by default: only the right people can touch each piece of data, a person still signs off on anything customer-facing, passwords and keys are stored securely, there's a record of who did what, and there's always a way to undo it if something goes wrong.

See the full answer on the Services page →

Our document workflows are a mess. People spend 20 minutes searching SharePoint for things that should be findable in 20 seconds. Is there a smart way to fix this?

Yes, this is one of the highest-impact AI projects for any business with documents scattered across folders. An AI assistant pointed at your real documents (with the right permission rules so it only shows each person what they're allowed to see) typically turns a 20-minute hunt into a 5-second answer.

The work means cataloging your existing documents, setting up the assistant, getting the permissions right (so the assistant doesn't show finance docs to people outside finance), and training the team on how to ask. Usually 4 to 8 weeks depending on how many documents you have.

Engagements: AI Workflow Build · $18,000 to $30,000 · 6 to 12 weeks (internal knowledge search is one of the most common first builds).

We're paying for Microsoft 365 and barely using anything beyond email and Teams. Can you tell us what we're missing?

Most Canadian small businesses I look at are using around 20% of what they're paying for. Depending on which Microsoft 365 plan you're on, you may have access to automatic workflows (Power Automate), business dashboards (Power BI), simple apps (Power Apps), document workflows (SharePoint), surveys and forms, smart lists, and the AI assistant (Copilot, usually a paid add-on). The Microsoft 365 Automation Plan reviews what you have, finds the high-value automation opportunities, sets up guardrails so it doesn't become a mess, and gives you a plan with priorities.

See the full answer on the Services page →

Our developers are talking about GitHub Copilot and AI coding assistants. Should we roll those out, and how do we keep our source code safe?

Probably yes, with guardrails. GitHub Copilot and similar tools genuinely lift developer productivity, but rolling them out without an IP policy (intellectual property, who owns what the AI helps write), a security setup, and a measurement plan tends to create a different set of problems six months in.

What I do: a security posture assessment, a GitHub Advanced Security setup plan, a Copilot governance and AI coding policy (what code can the AI see, what can it suggest, what gets flagged), and a way to measure whether it's actually helping.

Engagements: AI for software developers · $4,000 to $12,000 fixed. Every quote includes the ongoing retainer at $2,000 to $3,000/month, because coding tools and their security rules keep changing and a rollout nobody maintains drifts back within a year. You can decline it, but you'll see the number up front rather than a year later.

We don't have a website at all yet: just a phone number, an email, and maybe a Facebook page. Where do we even start?

Honestly, this is the easiest place to start because there's no legacy to worry about. The Basic package was designed exactly for this: $1,000, 1 to 2 weeks, fully done-for-you.

You bring me your business name, what you do, who you serve, and any photos or info you have. I handle everything else: the domain registration, the design, the copy structure (working from what you tell me), the Google search and Google Maps visibility, the contact form with auto-reply, the security, and 12 months of free hosting.

If you want zero hassle after launch, add Hosting & Domain Care at $55/month and we keep it running ongoing: domain, security, monitoring, small fixes, all handled. You can stop or change it anytime after the first 3 months.

Most businesses in your situation have a real professional web presence in about two weeks, from start to finish.

Engagements: Basic Web Design · $1,000 · 1 to 2 weeks (includes 12 months free hosting). Optional Hosting & Domain Care · $55/month after that.

See the Web Design packages →

Our website looks like it was built in 2018 and makes us look smaller than we are. Can you fix it without 6 months and $30K?

Yes, and faster and cheaper than people expect. I run three packages: Basic ($1,000 · 1 to 2 weeks), Standard ($3,500 · 2 to 3 weeks), and Premier ($9,500 to $12,000 · 4 to 6 weeks). Plus two ongoing options: Maintenance & Growth ($350 to $500/month) and Hosting & Domain Care ($55/month, available with any build).

See the Web Design packages →

AI is starting to surface in Google searches and ChatGPT answers. How do I make sure my business actually shows up when potential customers ask AI about us?

This is the new "Show Up in AI Search" service: setup $3,500 to $5,000 · 2 weeks. We restructure your site so AI can actually extract clean answers from it, add the invisible tags that tell AI systems exactly who you are and what you do, set up a real process for collecting customer reviews, and get you listed in the directories and credibility sources AI looks for before citing you. By the end, when someone asks ChatGPT or Google's AI "who does X in Halifax," you've got a fair shot at being one of the names that comes back. AI search doesn't sit still, though. The systems get retrained, your competitors keep adding content, and the answers change. Ongoing monitoring at $750 to $1,500/month tracks how AI tools actually describe your business, keeps your listings and reviews current, and puts the answer right when it drifts.

Engagement: Show Up in AI Search · setup $3,500 to $5,000 · 2 weeks. Ongoing monitoring · $750 to $1,500/month · we keep an eye on how AI systems describe you after launch.

Our employees are already using ChatGPT and other AI tools on their own. How do I know our customer information, business secrets, and private data aren't being exposed?

This is the question I hear most often now, and it's the right one to ask first.

This is what people call "Shadow AI": your team using AI tools you don't officially know about. Your team is experimenting with ChatGPT, Microsoft Copilot, Claude, and a half-dozen others. Data is going into those tools in ways nobody has mapped: customer information, internal documents, contracts, financial details. Policies haven't caught up.

I usually do a short AI usage audit, a plain-English AI use policy (three pages, not thirty), an approved Microsoft 365 Copilot rollout plan if you're already on Microsoft 365, and build four safeguards into every piece of work we automate going forward: only the right people can touch each piece of data, a person still signs off on anything customer-facing, passwords and keys are stored securely, and there's always a way to undo it if something goes wrong.

The goal isn't to stop your team from using AI. It's to give them a safer way to do it.

Engagements: AI Workflow Review · $4,000 · 2 weeks → AI Workflow Build · $18,000 to $30,000 · 6 to 12 weeks. Or Tech Advice on Retainer · $3,000/month.

See the full answer on the Services page →

My team built some automations on their own with Microsoft Power Automate, n8n, or Zapier. Are those safe? Has anyone reviewed them?

Probably not. The pattern I see most often: someone in operations built three or four automations during a busy quarter, they work, nobody documented them, and now those workflows are quietly handling customer data, payments, or internal records with no review and no clear owner.

What I do: walk through each existing automation, write down what it does, check what data it touches, identify who owns it, and write a short "what to do when it breaks" guide. Then a security check on permissions, passwords, and activity records. Usually 1 to 2 weeks for a small set of automations.

Engagements: Existing-Automation Review · $3,500 to $5,000 · 1 to 2 weeks · part of an AI Workflow Review.

We've outgrown DIY tech, but we're not big enough for a full-time tech chief. What's the middle path?

The middle path is the Tech Advice on Retainer service: a two-hour planning meeting each month, a rolling tech plan, tech-contract reviews, someone you can call, and light-touch tech oversight. You get experienced tech judgment on call without adding a $200K role.

See the full answer on the Services page →

Right now I make all the technology decisions myself and I'm tired of it. Can you be our IT brain on retainer?

Yes, that's the Tech Advice on Retainer service. Specifically: I take over the tech-decision burden. Vendor calls, renewal decisions, AI questions, employee tool requests, the "should we move to X" conversations: they come to me first. You stay informed, but you stop being the only one carrying it.

Plan on 6 to 18 months. Engagements often start after an initial assessment surfaces the biggest gaps and we agree on a roadmap to close them.

Engagements: Tech Advice on Retainer · $3,000/month · 3-month minimum.

How do I know a $2.5K to $30K AI project will actually pay back? I've heard the pitch before from "AI consultants" and got a strategy deck I couldn't use.

Fair concern, and I price the work to absorb that risk for you. The AI Opportunity Audit ($2,500) ends with a plan with priorities. If the plan doesn't surface at least one workflow where the math works (hours saved × hourly cost > project cost in under 12 months), I'll tell you that, and we don't proceed. If the audit isn't useful to you, I'll redo it or refund it.

For builds, I quote against the specific workflow we agreed on. The hours-saved math is written into the proposal. If the work doesn't deliver what was agreed, we keep working until it does or refund the difference.

Book a free 30-min call

What happens after the project ends? Will I be left holding a system my team doesn't understand?

No. Documentation is part of every project, not an add-on. You get a plain-English guide for what the workflow does, who owns it, where the data flows, and what to do when it breaks.

You also get 30 to 60 days of post-launch support depending on the project size. After that, you have three options: take it from there yourself, retain me as needed for occasional fixes, or move to a Maintenance & Growth retainer if it's a website, or a Tech Advice on Retainer if it's broader tech work.

Why should I trust Timberlea Consulting with my business?

You work directly with me, Sree Roy, from the first conversation through delivery. I bring twenty years of technology experience and explain the options in plain English.

Before work starts, we agree on the problem, the plan, and the price. I explain which tools are involved and what business information each one would handle. If you have privacy needs or rules about where your data must be stored, we look at those before we pick an approach.

You receive clear documentation for what we build. If I don't think a proposed project is worth the cost, I'll say so.

We're a non-profit. Can you actually help us, or is this just for businesses?

Yes. We reserve one reduced-fee or free slot per quarter for non-profits and community groups where the work matters and our advertised price doesn't fit. The principle: generosity that's bounded enough to be sustainable, one slot per quarter so it's never a maybe, but also never an empty promise.

How to inquire: tell us what you're trying to do, who it serves, and what you can realistically contribute. We'll figure something out together.

Run a non-profit or community group? We reserve one reduced-fee or free slot per quarter. Tell us what you are working on.

Inquire about the reserved slot