Sales reps spend the bulk of their day in Google Workspace — sending emails, building docs, booking meetings, or chatting with colleagues. But if you ask John MacDonald, Global Director of Google Workspace Growth Strategy & Solutions, very little of that time is optimized for actually selling smarter.
“We’re right now in the learning curve of AI fluency,” says MacDonald. “And so there are the haves and the have nots, and we’re starting to see a serious divide.” To be clear: Reps using Google Workspace already have the necessary tools sitting in front of them. “Those that choose to lean in and experiment will be very powerful, and the ones that choose to ignore it will slowly fall to the back of the pack.”
MacDonald walks through five habits that separate reps who are getting real value out of Workspace.
Table of Contents
- Making Google Workspace Work for Your Pipeline
- The Common Thread
- How the Google Gemini Connector and HubSpot Can Help
- The reps who show up smarter win.
Making Google Workspace Work for Your Pipeline
1. Know your prospect before you hit send.
The best reps never email blind. Before they write a word, MacDonald says, they already know where the relationship stands, what’s been discussed, and what the prospect actually cares about.
Going the extra mile used to be uncommon because it took time. Pulling together account history, researching a company’s industry position, and figuring out what’s actually top of mind for that buyer was a tedious process. Outreach defaulted to something closer to a generic pitch deck: “This is the narrative — you insert some slides and logos of customers in that industry that have done this,” MacDonald says, “and it tends to be a little bit more cookie cutter.”
AI has closed that gap. The same research that used to take days now takes “within a half an hour, maybe even 15 minutes of work,” he adds, using the same tools reps are already working in across Google Workspace. The result is a much more well-informed, customized pitch, which is no longer a luxury reserved for reps who happen to have extra time. It’s become the baseline.
Part of that speed comes from where the information lives. Now, AI can now pull directly from your CRM, surfacing account details already logged, and sometimes even information that pre-dates the sales rep’s experience. Account ownership shifts constantly, but the customer should never feel the change in hands.
2. Never walk into a meeting unprepared.
There’s a question MacDonald says he hears open too many sales meetings, and it’s become a red flag: Tell me what your biggest priorities are this year.
“It’s a nonstarter conversation in this day and age,” MacDonald says. “I don’t think it’s acceptable to have those conversations. Executives have always expected their representatives to show up better. Today’s technology makes it even more of an insult to walk into a discussion with an unresearched pitch and no vision for how the partnership could be mutually beneficial.”
Solid prep always needs to start well before the meeting itself. MacDonald points to something as routine as a weekly snapshot: Gemini pulling together what happened across a rep’s Gmail, Calendar, and Chat messages, including what they’ve already promised a prospect. Organizing that information now takes minutes and can be automated through agents that act like working colleagues.
Luck favors the prepared. Taking notes during a conversation is a good cue for important points to return to, MacDonald says. But it’s easy to miss exactly the wrong thing. “Often when we’re doing that, we’re missing the pieces that come right after it. We heard something that was really important, but we didn’t realize the thing we missed right after it, that might have been more important.” A transcribed, fully contextualized record, with an assistant taking notes alongside you, augments that context and fills the gaps.
The goal is to make sure the crucial points of the conversation are acknowledged through follow-on communication with the customer — a clear “what we heard you say was X, Y, and Z.” Miss the Y and Z, and your ability to foster the right partnership can be called into question.
MacDonald describes it as a reputation effect. People who consistently show up prepared bring real value to the partnership, MacDonald says. They can credibly reference previous discussions and pivot to well-constructed solutions for problems the customer has already voiced, a shift toward value selling that carries significant weight in a partnership. In practice, that means bringing a prospect’s likely concerns to the table before they have to raise them, rather than making the prospect do the heavy lifting.
3. Plan with precision — don’t invent it in the dialogue.
The follow-up to an initial meeting matters, but you can’t progress a conversation without maintaining it. Understanding the steps you envision to develop the relationship matters most, clear steps that may shift based on the exchange between rep and customer. Without a plan, a meeting can end on a high note and still leave no clear direction on what comes next, a nice exchange that doesn’t provide a roadmap to developing the relationship in a mutually beneficial way.
“I think the biggest mistake I see is that folks try to deliver a very effective presentation without understanding what the next step is themselves,” he says. “So how do you expect the customer to know what the next step is?”
He recommends the following approach to ensure clarity: enter every meeting with one to three well-defined objectives rather than a broad intention to sustain the dialogue. “A single objective is sufficient,” he notes, “as it allows for a highly deliberate focus.”
Requesting dedicated sessions with specialized teams — such as a collaborative workshop with the prospect’s marketing and sales groups, or a strategic alignment meeting with the Chief Revenue Officer (CRO) and their leadership team — serves as a critical diagnostic tool in the sales cycle.
First, this approach establishes clear operational expectations. By presenting a highly specific, high-value request — such as a deep-dive analysis of their daily workflow — you provide the prospect with a concrete proposal. This structure shifts the engagement from a vague, ongoing conversation to a defined partnership milestone, requiring an explicit commitment of their time and resources.
Second, the prospect’s response to this request serves as a vital qualification signal regarding internal authority.
- The “Yes” Signal: If the contact grants direct access to these key stakeholder groups, it validates their internal influence, confirms their buy-in, and signals a genuine mutual interest in advancing the relationship.
- The “No” Signal (Authority Gap): Conversely, a refusal or inability to facilitate these sessions often indicates that your primary contact lacks the organizational permission or mandate to broker such introductions. If they cannot grant an audience with the broader team, it is a strong indicator that the sales representative must navigate higher or wider within the organization to identify the true decision-makers who possess the authority to advance the deal.
And since we have AI as our assistant, we can draw context from automated meeting minutes, recordings, and our recollection of weighted importance. Validating the mutual understanding in a follow-up note will allow another level of confirmation and documentation of acceptance that all parties are agreeing to continue to grow the partnership.
4. Keep your pipeline moving without breaking your flow.
When our sellers are moving between document proposals and communications over to CRM systems and billing systems, they are constantly context switching. This produces “Switching Fatigue,” which distracts from the task at hand. Coupled with real-time messages coming through with timely requests, distraction becomes a very real state of most workers’ lives. Envision a focused state where context switching is minimized and access to information and context is drawn from the surface where work is happening. That is the paradigm shift that AI is providing to so many.
Imagine as an example, working in a proposal document and placing an @ mention to pull account context directly inside Google Docs or Gmail — naming the account right where they are engaged — and pulling the information back without switching screens. Not only does this save time from moving between surfaces, it retains focus on the task and minimizes the Fragmentation Tax.
This seamless retrieval logic extends far beyond document analysis. For instance, when managing sensitive or ambiguous customer correspondence, MacDonald notes that he can obtain critical context instantly without leaving his inbox: “If I receive an email from an escalated or concerned customer, I can immediately query Gemini using the @HubSpot connector to ask for any associated case numbers or background context. The system instantly retrieves all relevant information directly from our CRM, allowing me to respond swiftly and with full visibility and context of the escalation.” Timeliness of response and care to the issue further strengthens the partnership.
5. Play the long game — consistency builds retention.
For MacDonald, the sales relationship doesn’t end when the deal closes. Asked about the customers he’s worked with over nearly two decades at Google, he points out that most of them are still customers today. He compares it to his role as a father. “I’m a parent of three kids,” he says. “They say that 90% of parenting is showing up. If you show up and they know that you’re someone that can depend on, you’re someone they’re going to keep coming back to.”
This isn’t always easy. For sales teams, showing up means something more structural than good intentions. Account ownership shifts constantly: reps change territories, move roles, leave the company. MacDonald notes that this information “isn’t always fluid.” But when history is captured and connected rather than sitting in one single rep’s memory, the next person to own the account inherits the full picture instead of starting over.
MacDonald ties this directly to business outcomes, not just relationship quality. Showing up consistently, in his words, is what helps “reduce the likelihood of churn” and “improve customer satisfaction” over the life of an account. Ask yourself this: if you’re the partner who consistently shows up and delivers value, doesn’t that make it that much harder for your competitors to compete? I’ve developed partnerships with customers who admitted their current ‘vendor’ hadn’t shown up in years. That inactivity speaks volumes, and it’s not conducive to strong partnerships.
The Common Thread
The strategies above boil down to the same underlying need: easy access to the right context, at the right moment, without breaking your flow. The most successful reps aren’t doing more research. They’re doing faster research from wherever they already are, with CRM data that’s always a step ahead of the conversation.
How the Google Gemini Connector and HubSpot Can Help
As it turns out, the answer is already in the tools you’re using. That’s what the Google Gemini Connector with HubSpot unlocks.
It bears repeating: this works from anywhere a rep is already working, not just inside HubSpot itself. While drafting a proposal in Docs or replying to an email in Gmail, a sales rep can pull up the account context they need in the moment, right where they’re already typing, instead of stopping to go find it somewhere else.
MacDonald emphasizes that this isn’t about replacing HubSpot as the CRM of record. Reps, he says, will still use that to actually log and interrogate account information. It remains the natural home for managing an opportunity. What changes is everywhere else. They no longer have to switch between tabs to find what they need.
The goal, as MacDonald puts it, is for reps to show up to every interaction already holding the thread without having to stop and search for it.
The reps who show up smarter win.
Selling smarter is about removing the friction between a rep and the information they need to do their job well — before the meeting, during the conversation, and long after the deal closes. The Google Gemini Connector with HubSpot makes that easier by making the tools you use every day work harder for you.