Are Your One-On-Ones Fiction?

Many people will tell an external coach things they would never tell their employer. Not because the coach is wiser or nicer. Not even because the organization is dysfunctional.

They do it because the coach is safe.

The coach doesn’t determine their compensation. Doesn’t decide whether they get promoted. Doesn’t write their performance review or have any stake in office politics. The coach has no stake in the answer — only in helping them think clearly.

And that safety creates candour.

Over and over, I hear things like: I don’t actually want to be promoted. I just want to do good work and go home. Or: I want to start my own business one day, but I’m scared to admit that. Or: I’m burnt out, but I can’t say that, because then they’ll question whether I can handle the role.

These aren’t unusual confessions. They’re routine. And when I hear them, I have lots of advice for how that person can manage up — how to open the relationship with their manager enough to at least test whether honesty is possible. But I’m always a little bothered by the same thing: why is the person with less power the one I’ve been hired to help? What about their boss?

Most employees are withholding because honesty has, at some point, carried a cost. If not for them, then for someone they know. When someone says they don’t want a promotion, many leaders hear low ambition. When they say they’re overwhelmed, many leaders hear not capable. When they say they’re bored, many leaders hear flight risk. Humans are smart. They adapt. They’re also fear driven. They curate their answers and offer the professionally acceptable version of their ambitions: what’s safe, which may not be what’s true.

What’s safe may preserve political capital in the short term. But it creates a dangerous blind spot for the organization. When the employee eventually quits “out of the blue,” their manager is shocked. Sometimes hurt. I had no idea. I wish I’d known — we could have done something.

Perhaps they could have. But the employee didn’t believe that.

Most career development conversations are fiction.

Organizations believe their managers are having meaningful development conversations. Even if they’ve only been provided scant training. Even if the managers themselves aren’t clear on the career paths available to their staff. Why do I believe this? Because they mandate the conversations annually (at least). But these managers are usually having highly filtered, carefully managed exchanges where employees present the version of themselves they think the organization wants to see and the manager, with a sigh of relief, accepts this version of reality. If your managers are only hearing what employees think is safe to say, then every succession plan, every development plan, every retention strategy built on that information is at least partially wrong.

You cannot align people well when you don’t know what they actually want.

The missing ingredient is something that sounds too soft for business: love.

Not sentimental love. Leadership love. The kind that means genuinely wanting what’s best for someone, not just what’s most useful to the company right now.

The best leaders understand something that takes real maturity to accept: your employees’ ideal futures may not look the way you hoped. And that has to be okay. If you only support ambitions that benefit the company, that’s not development — it’s manipulation with better branding.

The cost of false assumptions is concrete and predictable.

The technically excellent employee who never wanted to manage people gets promoted into management because it’s “the next step.” Everyone loses: the employee is miserable, the team gets an unenthusiastic manager, and the company loses a great individual contributor.

The employee who privately says I’m not trying to climb the ladder, I just want meaningful work and some balance gets quietly labelled as lacking drive. Meanwhile, they may be one of the most reliable people in the building — a cultural stabilizer, a long-term knowledge holder, the person who could be an ideal mentor or technical specialist. Not everyone should be on the leadership track. Organizations need stars and they need anchors.

And then there’s the employee who quietly dreams of entrepreneurship, or a career pivot, or simply a different kind of life. If their manager has no idea, they can’t shape opportunities that might retain that person longer — or at least make the exit a good one. Not everyone can be retained forever. But many can be retained longer if managers understand what actually motivates them.

Most companies claim to support employee development. What they actually support is development that serves the company’s immediate needs.

They’re comfortable with ambition that looks like wanting promotion, more responsibility, or a deeper role in the organization. They’re less comfortable when ambition looks like wanting mastery instead of management, flexibility over advancement, or a job that funds a life rather than defines one. Employees sense this quickly. And when they do, they stop being honest.

The best managers recognize something most don’t: you don’t own your employees’ ambitions. You temporarily steward their development. Your job isn’t to force-fit people into your org chart. It’s to understand what energizes them, what level of responsibility they want, and what they’re trying to build — even when that path is unconventional, and even when it eventually leads elsewhere.

That said, radical transparency isn’t the goal.

I’m not suggesting employees should disclose every passing doubt or private aspiration. Nor should their managers encourage it. Complete openness isn’t realistic, and it isn’t always prudent. The goal is a workplace where employees can be honest enough — honest enough about their motivations, their limits, and their ambitions that the organization can make better decisions and the employee doesn’t feel compelled to perform a false version of themselves to remain in good standing.

That requires trust. And trust is built when managers consistently respond to honesty with curiosity instead of judgment, coaching instead of correction, support instead of suspicion. It sounds simple, but in my experience, it’s quite rare.

Here’s a useful test: if your employees were completely candid with you about what they want from their careers, would they expect that to help them or hurt them?

If the honest answer is hurt them, you don’t have a development problem. You have a trust problem. And until that’s addressed, your career conversations will continue to be fiction.

The fact that your employees are more honest with an external coach than with their manager should concern you — not because coaching is bad, but because of what it reveals: the safest place for professional honesty in your organization is outside your organization. That’s not a coaching success story. That’s a warning sign.

The organizations that win long-term will be the ones where employees no longer need an outsider to have the conversations they should be able to have internally. That happens when leaders create the conditions for truth-telling. And that starts — somewhat inconveniently — with caring about people for who they are, not just for what role you need them to play.