8 mins

What happens when there's trouble in paradise?

In my career at Buffer, I’ve been very fortunate to recruit for a company that many people see as a ‘dream company’, or if not quite so grand, a place that they’re looking forward to joining. We’re known for specific values, a commitment to inclusivity, and a flexible remote-first environment. Applicants have often followed the company for a while before joining and come on board with the feeling of having landed in paradise.

I’ve found that among my peers, hiring managers, or leaders at recognized companies, the expectation that ‘This time, it’ll be perfect!’ is not unique to Buffer. The more golden the expectations that this new job will be perfectly tuned to one’s preferences and opinions, the greater the disappointment at the first mistake, disagreement, or imperfection one encounters. In a few cases, this pendulum has swung straight from elation through to toxic negativity as we hit the inevitable workplace frustrations and the illusion shatters. It also can be a setup for over-engagement and burnout, as people find it harder to maintain healthy boundaries when it’s not just a job, but ‘the dream job’.

The first time I encountered this situation was with Emma (not her real name). I was her onboarding lead and shortly after, her engineering manager. Emma’s onboarding was marked with the most starry-eyed enthusiasm I’d ever seen. I happily talked up her hopes, equally in thrall. Eighteen months later, I was dreading my 1:1s; Emma was, by any standard, ‘toxic’. When she left to join another high-profile company, she shared that this time, it really was her ‘dream job’. I was relieved, yet I felt like a failure. I also had the sneaking suspicion that the next place was set up to fail. Two years later, she resigned from Next Company in a flurry of tweets. What had gone so very wrong?

Great expectations

Simply put, Emma’s expectations were unrealistic: she expected to always be praised, never given constructive feedback, and to have 100% of company decisions ‘feel good’ to her personally. When things felt ‘off’, Emma was bitterly disappointed, and her productivity and mood would tank. She would then vent her frustrations to her co-workers, inviting others to share their gripes. She’d take these petty grievances as further validation of her hurt feelings and become even more bitter. It was a toxic spiral of disappointed hopes and shattered dreams.

Things came to a head when the finance team revised our transparent salary formula. Nobody got a pay cut, of course, but Emma felt her cost of living factor ought to have been adjusted higher than it was. I focused on motivating Emma, trying to recapture her initial enthusiasm by sharing all the things that were great about the team, role, and company. It was the worst thing I could have done. The problem was not Emma’s motivation, it was the growing delta between her expectations and reality. Emma resigned just a few months later.

Mind the gap

I don’t fully agree that the key to happiness is low expectations: you should expect to be treated with respect, to be valued, and to have your work be a positive element of life. However, expecting a job – any job – to always and without fail fulfill 100% of your emotional, financial, and intellectual needs is unrealistic. For some, the expectation is that work will always be fascinating and drive career growth: resume-driven development results. For others, it’s about pay. For Emma, it was about emotional validation. Instead of further raising Emma’s hopes, giving the impression I agreed with her and endlessly holding space for her to process her emotions, I should have tried to close the gap.

Next time around, when I picked up a similar trend brewing with Anton (not his real name), my approach was very different. He didn’t stay forever (that’s an unrealistic expectation on the part of the manager!) but he did have a good run and was a productive team member throughout. When he joined his next company, he had realistic ideas of what might be good and bad, and even trusted me with thinking through the decision. Here’s what I did differently:

  1. Recruitment
  2. Expectations during onboarding
  3. Setting boundaries, being firm about acceptable behavior
  4. Teaching ‘disagree and commit’.


After having so thoroughly disappointed Emma, my approach to recruitment has fundamentally changed. Yes, I want to ‘sell’ the company and attract talent, but more so, I want to attract retainable talent. I ask candidates about what frustrates them at work, and if I notice something that could be true at Buffer, I’m open about it. For example, yes, we have lengthy asynchronous text discussions – if that’s a deal-breaker, don’t join. We blog a lot, but we don’t have all the answers, and we do change our stance. If you want everything solved, we’re not the place! Anton went into the role with a fairly clear sense of the culture, something I strive for with every hire.


During onboarding, I make a point of sharing things that could be messy or are in flux. For example, we’re currently figuring out a reorg now. I’m trying to make it less terrible, but I’m also proactively saying no reorg is perfect and you’ll likely notice things that don’t make sense or feel weird to you. That’s okay, we can talk about it, but you should expect some things to take a bit of getting used to.


This was where I failed most with Emma, allowing her disappointments to suck up most of our 1:1 time.

It’s even more important to remember your core job: give clear, actionable feedback and focus on career goals. With Anton, it worked to timebox talking about his frustrations by saying upfront ‘We can talk about that for ten minutes, and then we need to get onto your career prospects. I don’t want this to derail your promotion’. Tying it back to something he cared about (the next level in our framework) helped to contain the conversation.

It’s also important to share what is and isn’t okay when a teammate is becoming toxic. With Emma, I allowed her negativity to spill into team settings, and did little to stop her from venting in retros and standups. I now realize that this isn’t appropriate. I’ll ask to take concerns into the 1:1 setting, and I will give feedback on derailing meetings.

Disagree and commit

The most notable failing with Emma is that I didn’t broach ‘disagree and commit’. I listened endlessly and tried to solve her concerns even when they were well outside of my control. I felt helpless and guilty that I couldn’t meet her expectations and make her work-life ‘perfect’. I’m now more upfront about what I can and can’t change, and on what timeline. For example, with a salary disagreement, I can focus on leveling up in the career framework. I can also seek to represent their opinion, but am clear that this is only advice, or influence, at best. I’m open about what lies beyond our control, and clear that endlessly ruminating on it isn’t an option.

With Emma, we eventually got to this point, and she then saw that, fundamentally, she wasn’t aligned. I wish we’d gotten there sooner, and that I’d raised the need to disagree and commit, or talk about whether she wanted to remain at the company and begun managing her out. As a new manager, I thought my job was retention above all else. Now, I coach my engineering managers to focus on effectiveness and engagement. Retention is only desirable if the employee you’re retaining is effective and engaged.

The dark side of enthusiasm: over-engagement

In writing this, I realized that I, too, have been the starry-eyed idealist who struggled with the tradeoffs and pressures that come with reality in a software company. I value improvement and progress, so I react by playing the hero who, through my own willpower, will close that gap and force reality to meet my expectations. This did create positive change, and I experienced tremendous career growth. I also ended up with an anxiety disorder and some burnout.

I’ve since managed a few others who, like me, tend to become over-engaged when disappointed and see fixing the problem as their special mission. While these teammates will work hard, create change, and are often valued problem solvers, the risks of burning out and becoming cynical and toxic are very high. Research also finds they’re more likely to become difficult to manage and be suspicious of their managers’ intentions because they see their job as a calling. Mission-focused companies are therefore especially vulnerable to over-engaged employees.

In these cases, be sure to keep goals realistic, and use the methods above to set clear expectations with your report. Focus their efforts on areas where they do have control and can effect change. The management style of ‘bring me solutions not problems’ is here more likely to further drive over-engagement and burnout, so be available to discuss and explore an area without needing every problem to be already solved. Pay special attention to work hours, vacation time, and staffing levels, as having this type of employee do the job of a small team isn’t a long-term success strategy. Just because they likely can, does not mean they should.


Being proud of where you work is a wonderful thing, but seeing work as a calling, or having sky-high expectations of perfection, is a recipe for disappointment, toxicity, and burnout. It’s a complex dance between motivating your team and ensuring their hopes are realistic. But leaders can do a lot to mitigate this fall from grace by being candid and open in the recruitment process, giving feedback and setting boundaries in onboarding and 1:1s, and not being afraid of asking a teammate to disagree and commit.