(This post isn’t specific to product management, but a manager’s view of problematic communications. Not everyone on our teams expresses themselves clearly.)

Over the years, I’ve had a handful of direct reports come to me with employment ultimatums: “I’ll quit unless…” That’s a high-stakes way to open a conversation, something hard to un-say. As someone who tries to communicate clearly and encourages coworkers to do the same, I take these folks at their word: if I’m unable to deliver what’s required, I expect them to walk away.

But half the time, this has turned out to be a rhetorical maneuver: a way to signal urgency or importance from someone who isn’t adroit at office-speak. A clumsy way of voicing real concerns. And it’s gone over very badly: confusing real issues with idle threats. My general advice for employees is to reserve “I quit” for its literal, narrow, precise meaning — and choose less consequential words when possible. My advice to managers is to probe for underlying problems, not just react to strong language.

So putting on our touchy-feely communications hats instead of our hard-bitten market-dominating armor, let’s unpack a few sample discussions. We’ll take three ultimatums, consider how employees might have framed their concerns better, and how managers can dig for the real obstacle.

[1] “If I don’t get some more challenging and meaningful work, I’m quitting.”

Hmmm. Sounds very serious.

  • Maybe this is about a member of the team who’s been passed over for a promotion. Or others are getting praised for good work and insights. They feel that something unfair is happening.
    • I might coach the employee to start a more useful conversation with “I’m not sure my contributions are being appreciated…” or “I’ve been doing the same kind of work for a long time now, and I’m frustrated that new employees joining our team get to work on cool new projects…” Framing these as observations, backed up by facts or events, opens up a productive discussion.
    • A good manager can then respond with “Let’s talk about the feedback on your last set of deliverables and customer interactions…” or “Here are some skills that I can help you work on, that would be important in bigger assignments…” or even “We’ve been looking for opportunities to promote you, but there isn’t yet room in the department…” No need for anyone to turn in their ID badge and slam the door quite yet.
    • As the manager, you should probe before responding with “OK, good luck in your job search.”
  • Perhaps this person doesn’t find the everyday work of product management (or whatever specific role) fulfilling. The position was advertised as exciting and strategic and heroic, but turns out to be as unsexy as other jobs.
    • A more honest (and productive) opening for the employee could be “I’m bored with what I’m doing” or “My team doesn’t listen to me” or “I thought I got the be the CEO of my product.”
    • Useful responses might include “You’re new to product management, so let’s get you some coaching/mentoring” or “I’m seeing a specific problem in how you issue orders to your development team” or even “Maybe product management isn’t the best fit for you. Let’s talk about roles within the company that align with your skills and interests. You might do better in Customer Success or Sales Engineering or Financial Operations…”
    • Again, managers should probe for real concerns even if the employee didn’t open the discussion well.
  • It’s possible the product team as a whole has little ability to make choices, drive good customer outcomes, and improve its offerings. CTOs or CEOs or Sales VPs swoop in, override decisions, and mortgage next year in favor of this quarter. If so, it’s hard for most product folks to feel enthusiastic or empowered.
    • A seasoned employee might depersonalize and generalize this. “It doesn’t seem like we’re succeeding as a product management group” or “As our Head of Product, are there ways you can reduce executive interference for us?” or perhaps “The recent exodus of product managers reflects our lack of clout.”
    • Even without a crisp problem statement from the employee, the manager can restate/reframe what’s going on. The conversation might swerve from “Thanks, those are very helpful observations” to “Here are things I’ve been working on to improve our team’s situation” to “Do you have suggestions for how we can address this?”

[2] “I need a 20% raise or I’m quitting.”

Hmm. A lot to ask for, especially if we’re not in a salary review cycle. We’ll want to understand what’s really going on.

  • This might be a competitive recruiting situation, where your employee is anticipating (or already has) another job offer.
    • So a more straightforward employee might say “I’ve been offered a job at Company X with more money and better title and generous work-from-home policy. If you can match that, I’ll consider staying.”
    • Seasoned managers know that it’s hard to keep folks on the team once they’ve started interviewing elsewhere: money is only one part of the equation. Employees usually decide to leave (for internal reasons) before choosing where to go for their next gig. And they rarely stay very long even if we meet salary demands. So I don’t believe in counter-offers: I’d respond with “Congratulations on your new opportunity. Let’s work out a transition plan for your current projects.” Followed by “Tell me what started you looking outside?”
  • There might be something else going on, though. Our employee could afraid to share that a family member is very ill, with potentially catastrophic financial impact. Or a sudden uptick in local rents is putting pressure on everyone.
    • A savvier (or more trusting) employee would be clearer: “My partner has a sudden disease, and I’m not sure I can carry us financially through the quarter.” Or “Recruiters are phoning all of us, offering big raises. I love my job and don’t want to leave, but our pay scale is under-market.” Or even “San Francisco rents are so outrageous that the junior folks of the department are tripling up in one-bedroom apartments.”  The circumstances matter.
    • Responses here may not be obvious, and will vary widely, but identifying the core problem helps frame responses.  “We have a family leave policy that gives you some emergency time off, which might be more helpful than cash” or “Let’s get HR on an external salary benchmark ASAP” or even “Telecommuting one or two days per week could let you consider commuting from less expensive areas…”
    • Our goal as managers is to identify underlying difficulties, not just react to inflammatory words, so we can respond appropriately.  Some members of our team are less experienced, or less articulate, so may have skipped right to threats.

[3] “We need a much more diverse workplace, or I’m going to quit.”

This could indicate a range of personal or team-level or corporate-wide issues. Managers would be well advised to listen carefully, repeat for clarification, and not get defensive. Can we figure out what’s happening?

  • We know that diverse teams build better products and have more market success. Yet most tech companies struggle with diversity around gender, age, ethnicity, nationality, schools, and liberal arts vs. STEM. As leaders who want the best teams and the best environments for those teams, we should be eager to hear about problems in hiring and promotions.
    • Instead of threats, a perceptive employee who feels safe raising issues might frame this as “We’re turning away or failing to attract strong candidates because of problems in our job postings, recruiting, reputation in the community…”
    • Smart managers can then respond with “I may have missed this; tell me more” or “Yes, I see that too. Can I get your thoughts on changes we might make?” or even “I’m not sure how to address this. We could get some help from HR or an outside expert…”  Even faced with an ultimatum, though, we would be digging in.
  • Avoiding ultimatums, some mid-level women have thoughtfully said:
    • “There are no women on the senior leadership team, and I wonder if I can succeed at our company.”  More constructive than an immediate threat to quit. And a tough problem to address.
    • That gives us (as managers) an opportunity for honest discussion about company culture.  Or to help unpack what our employee is trying to say.  And then to have our own uncomfortable discussions in the executive suite, framed constructively: “The company’s lack of diversity at the top is hurting both recruiting and retention.  Who are the strong mid-level leaders ready for bigger roles that we’ve unintentionally passed over?”
  • Or it could be something toxic, a real crisis with specific legal implications:
    • “This is a hostile workplace. I can’t work here if person X keeps doing Y.”
    • IMHO, this shouldn’t be a surprise to observant managers. But in any case, we should listen carefully, take good notes, believe our employee even if we not have experienced the problem ourselves, and (probably) bring HR or Legal in right away. If a founder or senior executive is mentioned in the discussion, we can expect our own impressions (and willingness to continue working at the company) to be questioned.

So a surprise declaration that “I’ll quit unless…” can be difficult. But not everyone expresses themselves well, or inspects their own motivations. So an ultimatum could be just what it seems — or a poorly formulated request for help. Good managers need to dig deep, and find out which.  So we can then say — and do — the right things.