I want to talk about leadership, and its close sibling, trust.
Specifically, why we need both so badly right now, and why the companies we rely on are struggling to provide either. I’m going to use HubSpot as the case study, because HubSpot is the foundation of my business, my career, my livelihood. I watch it closely, both the product and the people, because the signals tell me how I should be guiding my own clients.
Fair warning: this is not a piece where I’m kind to them.
We are all looking for direction
We’re living through rapid change, and the word we keep landing on is uncertain. Not unprecedented, that one’s tired. Uncertain.
In times like these we look upward for direction. To our suppliers, to our platforms, to our politicians and governments, and to the businesses we buy from. If they lead, we follow. That’s the deal.
For its first decade, HubSpot did lead. There was a strength there, a certainty. HubSpot knew where the industry was going, and we, as users and partners of their tools, knew how to serve our own clients because of it. We just needed to follow.
The last year or so has looked different. HubSpot is floundering, unsure of where it’s going, which puts it in the same boat as almost every other company. And the strategy that emerges when a company doesn’t know where it’s going is always the same: More. More features, more updates, more messaging, more content. Just more, more, more. If you don’t know what you’re doing, try lots of things.
I’ll come back to this, because I think the opposite is true. Less is the answer.
The messaging from Unbound
They’re moving up market. Their investor advisories and partner communications have said so for a year or two now. They never say it directly, but any observer can see it. HubSpot is going after Salesforce: mid market and enterprise. That makes complete sense.
Then the co-founder said the opposite. At Unbound, Dharmesh Shah stood on stage and talked about the rise of the solopreneur, the one person business, and then used his keynote to launch a product for exactly those people. HubSpot’s customer base skews mid to large. Sitting in that audience, you’d be bewildered. This is not leadership. This is a company that doesn’t know where it’s going, so it’s targeting everybody (‘we’re pushing up-market, but growing downmarket volume’).
The CEO’s ‘outcomes’ message. Yamini Rangan talked about outcomes. That word has been the marketing buzzword of the past year, and it’s been puzzling to me the whole time, because for any business that provides services to clients, outcomes (results) are the entire point. Hearing it from the stage as though it is news is… strange.
It took me a while to work out why they were talking about it. Then it clicked: it’s a message to themselves. Most of their customers, businesses like ours, already focus relentlessly on outcomes. HubSpot hasn’t. They’ve been shipping an incredible release rate of new features, often AI-powered, generously described as ‘value’. A lot of it is AI slop. It doesn’t drive outcomes. It drives confusion and overwhelm.
So when the CEO told the room to focus on outcomes, she was primarily talking to herself, her leadership team, to HubSpot. Which, frankly, is a message they need. Just not one for the audience.
The demo. The chief product officer gave a canned demo built on a fictitious fantasy role, showing outcomes that don’t survive most reality checks. Example: A salesperson generating an AI summary to send to their sales manager (ie workslop). A complete disconnect from how the work actually happens. On a product announcement, no less. Failed leadership, out of touch with client needs, and no path out.
Loop marketing. I’ll say this one plainly, including my own part in it. Kipp Bodnar’s loop marketing, complete with a book and the CEO repeating the sound bites, is a contrived idea. They pushed it because they didn’t have anything else. I fell into the trap last year, trying to find substance in it and apply it for our clients. I realise now: there was none. It’s noise.
The summary of all of it: more, for the sake of more. A company that grew fast in good economic times, when demand outstripped supply, now struggling to find a coherent message in a saturated, overwhelmed market.
Trust is the sibling, and it’s being eroded
Here’s the thing about trust. Even without clear direction and leadership, if your clients trust you, you can still succeed. So, one of the fastest ways to undermine a business is to destroy trust.
Hollow out a differentiator. HubSpot’s customer support was world class two years ago. Now it’s fronted by AI responses that are decent sometimes, bad others, and mediocre on average. That’s a differentiator surrendered, and with it, trust.
On HubShots, the show I co-host with Ian, we regularly held up three companies for years as exceptional at support: HubSpot, WP Engine, and Amazon. I’m sure you can name a few others yourself. The reason you can name them is that most companies are terrible at it, even the ones that breathlessly claim to be exceptional. So when you find one that’s genuinely good, it stands out, and it becomes a differentiator.
WP Engine has gone the same way. Contact their support and you’ll get an AI-generated wall of text that’s sometimes helpful, often not, and occasionally worse than no response because it walks you down paths you should avoid. Chat wait times (for a human) used to be minutes. Now it’s hours, or an email within a business day.
Why would I stick with you? There’s no differentiation left. No direction, no leadership, no compelling reason to stay.
Handle hard decisions badly. HubSpot cut seven percent of staff recently. I don’t see the redundancies themselves as a failure of leadership or a breach of trust. That’s business reality, and we’re watching it everywhere right now. What cost a little trust was the messaging around it, which felt convoluted and PR-polished, and Dharmesh’s commentary on LinkedIn, which read as tone deaf (to be fair, he later updated it, acknowledging such). Remember their Culture Code? How times change.
Why HubSpot is the useful example
I realise I’m a nobody, running a small company, downunder in Australia. Who am I to be critiquing HubSpot, the company I depend on. And why?
Here’s why: Because they’re a billion dollar company that got incredibly successful, and they exemplify every problem the rest of us are working through. We can learn from their mistakes. Their struggle. Their lack of strong leadership to guide through uncertain times. Their erosion of differentiators, their decisions to reduce trust signals.
The lesson is about learning from HubSpot. Avoiding their pitfalls. In a nutshell it’s this: we need to provide leadership (clear direction), and give our customers (and our market) real reasons to trust us.
So what do we do?
Acknowledge the season. Let’s get this obvious note out of the way. Leading people through uncertainty starts with naming it. We’re in uncertain conditions. There is no miracle cure and no quick resolution. This is not a time for quick hacks or simple three-step improvements, and it is absolutely not the time to push more at an audience that’s already overwhelmed.
Tailor the direction. With every client I work with, we want to understand the business, their differentiation in the market, the specific added value they provide, and then build a process ecosystem (in our case, based on HubSpot) that lets them deliver it effectively. That’s it. A solution tailored to their circumstances. No demoware, no contrived examples, no blanket cookie-cutter solutions, no fortune cookie wisdom.
I’m aware that sounds obvious. The problem is that in an overwhelmed, noisy market we instinctively reach for templates, checklists and three-step frameworks, thinking they’ll solve it. They won’t. Every business is its own complex knot of people and processes, so the platforms and implementation around it have to be tailored too. A generic framework rarely applies unaltered.
That’s also why we’re seeing a rise in smaller businesses attacking very specific problems. That’s what leadership looks like in this season: guiding people through uncertain waters by shaping the specific process to the people and the value they provide.
Trust through clear thinking. Everyone can spin up a website. Everyone can spin up social content and email at scale. Being present in the market with messaging is not what creates trust.
Clear thinking does. Thinking that understands the situation and applies it to the circumstances of the customer or the industry. That’s what we try to do on the show, in the newsletter, in our posts. Less breathless ‘gamechangers’ and regurgitated release notes, more clear thinking in uncertain times. Sharing a tip on its own can be mildly helpful, sharing why it is useful and when it applies in the real world is valuable. Show it to your team first, then to your broader customer base, and you grow trust with both.
The format is up to you. Content, video, in-person events, whatever suits you and your clients. The substance has to be the thinking.
The personal trainer (PT) model
Here’s the model that I think fits this season. I think of it as the ‘personal trainer’ approach.
If you’ve been to a gym and worked with a PT, this lands immediately. And it maps neatly onto the difference from coaching, consulting, training, implementation and strategy workshops.
Most people who go to the gym don’t work with a trainer. Based on the figures I’ve looked at, roughly twenty percent do. It’s often triggered by a new year’s resolution or a health scare, and it might last a long time or a short one. It’s not for everyone, and it’s definitely not the majority.
Most businesses don’t work with a ‘personal trainer’ either. Which means most businesses wouldn’t work with someone like me: a ‘personal trainer’ for their business, their HubSpot, the way they work with their platforms.
So what does a PT actually do?
They start with the goal. Weight loss, building muscle, rehabilitation, cardio fitness, recovery. For a business the goal might be marketing improvement, sales process optimisation, a growth metric, AI application, cleaning their data. Understanding the goal comes first, always.
They build the programme. From a gym full of equipment, they point you at the few key pieces that get you to your goal. Same principle in a sea of platform features and AI overwhelm: which parts of the platform deserve your focus right now. The answer isn’t more. The answer is less.
They rarely lift the weights. They demonstrate how the movement should be done, then hand it back to the client, watching and reviewing their form, tweaking their approach (the Breeze Assistant prompt, the workflow actions, the custom report build) as needed.
They provide accountability. Most people quit the gym. A trainer keeps them showing up, and part of that is measuring results and showing the improvement. Adapting the program as appropriate.
They curate the knowledge. All the research on nutrition, recovery, weight loss and training gets filtered down to what serves your goal. That’s exactly what a good HubSpot partner does with the noise, the releases, the distractions and the overwhelm: curate it down to the parts that benefit you most.
I think this is the model for discretionary businesses over the next year or two, and probably longer.
Aside: A discretionary business in B2B is one you don’t have to engage with today. You can put off the purchase decision and still survive. Most businesses are discretionary. The non-discretionary ones sit around regulation: tax, payroll, compliance, standards. Those can’t be put off, so they behave differently. But for the bulk of businesses, the buying decision can wait, and that changes what they need from you. From me.
Back to our personal trainer concept. Sometimes people need help putting the gym together, and that’s onboarding and implementation. To push this analogy one step further: joining a gym is buying HubSpot. Building a home gym is the Claude connector into HubSpot, or a CRM you’ve vibe coded yourself. A personal trainer can help you assemble the equipment. Then they turn their attention back to you using it effectively.
The personal trainer doesn’t do much implementation. They might lead by example, building the first workflow, the first agent, the first email series. Then they guide you to do the rest, because that’s what businesses want now. Three years ago they wanted to outsource the whole thing to an agency. These days they want it implemented in-house. They want to be trained, guided and curated on where to focus.
They get you there faster. Why hire a trainer when you can watch YouTube, download an app, and get AI to write you a programme? Speed. A good trainer gets you there faster. If they don’t, they’re not a good trainer.
That sets the standard for us, too. Lead by example. Nobody hires a trainer who can’t do a push-up. Those trainers don’t survive. So show how you do it, then guide your clients to do it themselves, faster.
What this means for you
Showing what to do and how you do it is the leadership part. Demonstrating clear thinking is the trust part.
Adopting a personal trainer approach is the engagement model that gives our clients the most value (it gets them there faster).
If you’re running a discretionary business, I’d suggest it’s the model you should be thinking about for your clients too.
