A dating word enters the office
In dating, “wildflowering” is the idea of letting a relationship grow without a lot of forcing, scripting, or premature labels. It’s a loose, slightly romantic term, which is probably why it feels so strange in an office memo. Yet that’s exactly where it’s landing now, because the same logic is being borrowed for careers: let people develop in the shape that actually fits them, rather than making everyone climb the same neat ladder at the same pace.
Macaire Montini, HiBob’s VP of People and Culture, is one of the executives arguing for that approach as AI spreads through white-collar work. Her point’s easy enough to grasp. Companies are rolling out AI tools at speed, often with a lot of enthusiasm and not much patience for old workflows. Career paths, though, still look a lot like they did years ago: tidy hierarchies, fixed titles and a promotion system that assumes every employee should move upward in a straight line. The software may have changed. The org chart, less so.
That mismatch matters because office life is now full of awkward little contradictions. And it works. A manager can approve an AI tool on a Tuesday and still judge an employee’s growth using a framework built for a slower era, when job duties were easier to pin down and teams changed less often. In tech news, ai policy debates and even everyday digital culture, people keep asking how much work AI should take on. The harder question inside companies is who gets to grow, who gets credit, and what counts as progress when the tasks themselves are shifting under everyone’s feet.
Montini’s pitch for wildflowering’s basically a challenge to the old script. If people can build skills in different directions, take on more varied work and find room to stretch without waiting for a title change every time, then maybe career development looks less like a ladder and more like a working agreement between employee and employer. That sounds humane, even sensible, which is why it gets attention. It also makes some managers twitch a little, because promotions do more than flatter vanity. They decide pay, status and power. And they tell the rest of the company who’s expected to lead, who’s trusted with decisions, and who gets recognized in public.
A career can grow in more than one direction, but companies still have to decide how to reward the people doing the growing.
That’s the rub. A more flexible model can give people room to build on strengths that don’t fit a standard career track. It can also make accountability murkier if the rules are vague. Who notices?, if somebody quietly absorbs more responsibility. If a person keeps the team moving but never gets a title bump, what happens to morale? And if AI takes over chunks of routine work, does promotion now mean managing more systems, more people, or simply more uncertainty?
From there, those questions sit right at the edge of power and politics inside a company, which is why this idea has legs beyond a feel-good workplace trend. It asks who gets seen, who gets promoted, and whether “growth” has to look the same for everyone. That’s where the model gets interesting, and where the arguments start.
From ladders to career mushrooms
Montini’s “career mushrooms” idea starts with a simple complaint: a lot of companies still treat advancement like a single narrow staircase, even when the work itself has already sprawled into something messier. In her view, people don’t all grow by taking on a bigger title every 18 months and climbing one rung at a time. They often grow sideways first. A person learns a new tool, picks up a side project, gets trusted with a weird little problem no one else wants, then slowly becomes the person everyone turns to for that slice of work. The promotion, if it comes, is late in the story, not the whole plot.
That’s where wildflowering at work gets more concrete. The idea pushes managers to stop fitting every employee into the same tidy template and start noticing how each person actually works. One employee may be best when they’re given room to sketch ideas and test them. Another may be strongest when a vague request turns into a clean process by Friday afternoon. A third might be the calm one in the room who can spot a bad assumption before it becomes a six-month mistake. Under a rigid ladder, those differences can get flattened out. Under wildflowering, they become the starting point.
The trick is not to make every career look the same. It’s to build a workplace where different strengths can grow without being squeezed into one mold.
Montini’s soil-and-seed comparison gets at that logic without too much corporate perfume on it. The company, in this telling, doesn’t manufacture the employee’s shape. It provides the conditions: a decent manager, clear expectations, access to training, room to try things and enough trust that people can stretch without being punished for every imperfect first draft. Growth looks different from person to person, after that. Some employees shoot up quickly. Others spread out first, adding skills, context and confidence before they move into a bigger role. The employer’s job isn’t to force uniformity. It’s to keep the ground workable.
That matters more now because AI has started taking over a lot of the repetitive stuff that used to fill the calendar. Drafting a first-pass memo, summarizing meeting notes, sorting routine requests, tagging documents, even some entry-level analysis can now be done faster by software than by a junior employee working late with three tabs open and a cold coffee. When that happens, the human value shifts. Creativity matters more because the machine can generate plenty of bland options, but it still needs a person to choose what’s worth saying. Judgment matters more because somebody has to decide which output’s nonsense and which is actually useful. Adaptability matters more because the toolset changes constantly, and the person who refuses to move tends to get left holding the old instructions manual.
That doesn’t mean AI replaces managers or makes career planning automatic. It means the skills companies used to treat as nice-to-have extras start doing more of the heavy lifting. The person who can frame a problem clearly, switch between tasks without losing the thread, and work out how to use AI without handing over the steering wheel becomes a lot more valuable than the person who can just repeat a process quickly. In an AI workplace, speed alone is a weak flex. Plenty of software’s fast. The question is whether the work is any good.
For that to happen, though, AI has to be treated as an actual workplace tool, not a checkbox on a launch announcement. A lot of firms have rolled it out the way some people buy a treadmill: it looks good in the corner, and nobody uses it correctly. Workers get a new app, a hopeful memo and maybe a cheery line about experimentation, but little guidance on what the tool is for, where it’s allowed, or who gets to approve a new use case. The result is predictable. People either avoid it because they’re unsure about the rules, or they use it in private and hope nobody asks how the sausage got made.
That’s where the daily mechanics matter. If a team is going to use AI well, managers need to say what can be automated, what needs a human draft, where the guardrails sit, and how people should share what they’ve learned. They also need to give permission to experiment without turning every test into a compliance drama. Small examples help. A manager who lets a team compare AI-generated summaries against human ones will usually learn more than a manager who merely announces that “we’re an AI-first team” and then goes back to approving expense reports one by one. One approach changes behavior. The other changes slide decks.
The fairness issue sits nearby too. In hybrid teams, people who are physically present can end up getting noticed more than remote colleagues, even when the remote worker did the harder thinking. That bias has been documented in workplace guidance from SHRM on hybrid teams and in Gallup’s research on managing remote workers, which both point to the same practical problem: visibility often gets confused with contribution. If companies want career progression to reflect actual work rather than who happened to linger after a meeting, they need systems that make output easier to see and compare. Otherwise the person with the loudest chair gets credit, which is a terrible promotion method and a weird way to run a company.
Wildflowering, then, is less about sentiment than design. It asks managers to notice what each person already does well, what can be taught and where AI can remove grunt work without stripping away judgment. Done well, it gives employees a wider path. Done badly, it becomes a pleasant-sounding excuse for vague expectations and extra unpaid responsibility, which is how a lot of office experiments begin when nobody writes the rules down.
What happens to titles, promotions, and power
Once you move past the philosophy, the next question is the one people actually ask after the meeting ends: what happens to my title, my pay band, and my shot at a better role?
Titles still matter. They matter when someone’s comparing salaries across companies, scanning LinkedIn, or trying to guess whether a role is a stretch or a trap. Inside a company, though. They can start to matter less if managers stop treating them as the only evidence that someone has grown. That opens the door to skills-based promotions, where a person can gain scope, pay and trust without waiting for a fancier label to land on their email signature.
The problem with going fully flat is that it can get fuzzy very quickly. If nobody has a clear title, accountability can drift. Work still has to land somewhere, and in a lot of offices it quietly lands on the same dependable people over and over. They take the messy client call, fix the broken spreadsheet, soothe the teammate who missed the deadline and somehow end up carrying more than their fair share without a clean path to recognition. A flat org can sound democratic on paper. In practice, it can also become a place where the invisible labor piles up in silence.
A flatter company only works when the work itself becomes easier to see.
That’s where the idea of a skills passport comes in. Instead of treating promotion as a single leap from one title to the next, managers would track earned stamps for specific capabilities. Someone might collect stamps for leading a product launch, handling a difficult negotiation, training new hires, or using AI tools to shave hours off a reporting process. The document’s less glamorous than “Senior” anything, but it’s a lot more honest (to put it mildly). It tells workers what they’ve actually done, not just what their business card says.
The appeal is easy to see in a market that’s long loved title inflation. In the United States, companies regularly hand out bigger job titles to keep people from walking out the door. A coordinator becomes a manager, and a manager becomes a director. Sometimes the scope grows, sometimes it doesn’t. The title does the emotional heavy lifting. That game can keep a recruiter at bay for a while, but it also makes it harder for everyone else to know what a person really does. The label sounds impressive, yet the job itself may not have changed much.
That is one reason the move toward more flexible office culture keeps showing up alongside broader discussions about promotion chances. A rigid ladder works best when every job looks alike and every worker follows the same route. Once teams are built around different strengths, that ladder starts to wobble. The Census Bureau has a useful look at work-from-home inequalities, and the broad lesson fits here: access, visibility, and opportunity do not land evenly just because an organization says it is modern now. If some people are closer to decision-makers, or simply easier to see, their growth can get treated as more natural than everyone else’s.
That is also why the newer flexible-work playbook keeps stressing leadership habits instead of just attendance rules. Gallup’s guide to strong, flexible work culture gets at a practical point companies often miss: if managers do not define outcomes clearly, flexibility turns into guesswork, and guesswork is where promotion decisions get sloppy. You can’t reward what you can’t describe.
Some employers have already tried to design work around how people actually think, rather than forcing everyone through the same narrow process. Microsoft’s neurodiverse hiring program is a good example. The company’s used a different interview format for autistic candidates, with clearer prompts and more direct tasks, so applicants can show how they solve problems instead of how well they survive a traditional interview gauntlet. That approach says something useful about promotion chances too. If the company already knows that people work in different ways, it can stop pretending one style of performance is the only one that counts.
The cleaner version of this idea shows up in pods. Small teams, and shared information. One common purpose. Fewer decision layers between the person doing the work and the person approving it. In that setup, the office is less interested in whether someone’s “above” or “below” someone else and more interested in who leads a discussion, who negotiates with the client, who creates the draft, and who solves the problem when the first draft falls apart. That makes responsibility easier to trace. It also makes it harder for strong performers to disappear inside a tall org chart.
Whether companies use titles, stamps, or some hybrid of the two, the question is the same. Can they make progress legible without turning every job into a tiny throne?
That question gets trickier once AI starts changing which tasks deserve a manager’s attention in the first place.
Why the next few years will be messy
For all the neat talk around wildflowering, the next few years in offices may feel less like a clean redesign and more like a long adjustment period with a few ugly patches. AI is already taking over work that used to give new hires their first real foothold. Drafting routine emails, sorting data, scheduling, basic reporting, first-pass research, all of that can now be done faster and cheaper by software that never asks for lunch. That leaves some industries with a shorter runway for entry-level workers, which is awkward in the plainest possible way: if the first job gets thinner, the first promotion often gets harder to earn.
A flatter org chart can look humane right up until nobody is sure who owns the extra work.
That problem doesn’t stop with new grads. Flat structures have already pushed a lot of middle managers into oversized spans of control, and the job can turn into a strange blend of referee, translator and emergency brake. One manager may be trying to support a dozen people, or more, while still filing reports upward and keeping projects moving. At the same time, the path to promotion can feel narrower than it did a few years ago. If there are fewer clean rungs on the way up, people start asking what exactly they’re supposed to be doing all year besides waiting.
That’s where the messiness gets political inside a company, not just operational. Title inflation exists for a reason. Some employers hand out grander titles instead of more scope, more pay, or a better role, if people can’t see a clear way to grow. It looks tidy on LinkedIn. Inside the company, it can feel like a patch over a hole in the floor.
Macaire Montini, HiBob’s VP of People and Culture, has warned that the next two to five years may be unstable as AI keeps changing how jobs are divided up. That sounds right, and a bit understated. Work design is moving faster than the habits built around it. A team may lose one kind of task this quarter, then pick up a new one next quarter because the software changed, the policy changed, or the manager decided to reorganize the workflow again. People hate uncertainty when it shows up in their paycheck, their title, or their day-to-day responsibilities. That’s not exactly a shocking revelation, but it does explain why these experiments can trigger real resistance.
The generational angle makes it even messier. A 24-year-old who grew up swapping apps, side projects and short stints may find the whole wildflowering idea fairly natural. And a worker who spent 20 years under a more traditional ladder may hear the same pitch and wonder whether it means less security, fuzzier promotions, and more work with fewer labels attached. Neither reaction is silly. They’re both shaped by the workplace people entered. One group learned to expect movement across projects. Another learned to expect advancement through titles and formal steps. Put four generations in the same office and you’ll get four different ideas of what “growth” should look like.
Companies can’t fix that with a shiny AI rollout and a cheerful memo. They’ll need actual training, coaching and development time if they want people to adapt without checking out. That means teaching managers how to evaluate broader skill sets. It means giving workers a path to build new abilities instead of asking them to absorb change by osmosis, which, to be blunt, isn’t a training plan. It also means making space for people to learn the tools they’re now expected to use, rather than pretending everyone will somehow pick it up between meetings. Careers may stop being judged only by how high someone climbs and start being judged by how wide they can grow, if employers get this right. That probably won’t make the next few years feel calm. It might make them more honest, though.
