When People Leave...

Let’s say you have a direct, Pia, who’s been with you for three years and is one of your top performers. One day she asks if you have a minute, and informs you she has an offer from another team and is thinking about taking it. What do you do?

Here you were, doing your best to make sure Pia was being fairly represented in talent reviews and was getting compensated according to her contributions. You gave her credit when she succeeded and shielded her from organizational BS. You cared.

And while you were doing all that, she was interviewing.

As always in case of trauma, and, let’s face it, having a team member leave unexpectedly is traumatic, the first thing to address is your own emotions.

Feels like a betrayal, don’t it? Your rational mind knows that the emotion makes no sense, that business is business. But empathy means being empathic to yourself, and the first step on that path is noticing and acknowledging what you’re feeling.

The next step is to voice it. From the perspective of leaning into transparency, it’s okay to express how you feel, as long as it’s not done in a punitive way. For example,

“Wow, Pia, I’m happy for you, and I’m also really sad that you’ve decided to look elsewhere. What made you think about another position?”

You see how an expression of your own emotions naturally translates into curiosity about hers? The point isn’t to dwell on your feelings of betrayal and sadness. The point is to acknowledge them. Doing so creates room for further discussion.

Why people leave

People leave teams for three main reasons: manager, culture, and domain. Let’s examine each from Pia’s point of view to see what might’ve gone wrong, how you could handle the conversation around each of these possible reasons, what you might be still able to do to fix it, and how to apply these learnings to the rest of your team.

Manager

The top reason employees seek opportunities elsewhere is due to issues with their manager. This can range from personality conflicts, to manager perception (possibly resulting in inequitable compensation), lack of visibility, low promotion velocity. Throw in bad communication and scalability issues, and you have a full cocktail of causes.

The problem, in the context of Pia’s scenario, may be a lack of trust. To wit, Pia hadn’t told you she was looking. She hadn’t even told you she was unhappy. You found out about the issue only when her shoes were pointed toward the door.

It might be that she didn’t trust you enough to tell you there was something wrong. Or it might be that she was culturally or family-conditioned with the assumption that, no matter how good her manager was, the moment he became aware of her unhappiness, he’d turn on her.

You have no way of knowing what’s driving her thoughts here, so let’s ask:

“What made you think about another position?”

Now that Pia has an offer in hand, she’s much more likely to be upfront with her concerns. Listen. Acknowledge what she’s saying.

“Sounds like I wasn’t giving you enough credit for your work.”

“Sounds like I kept your plate too full, not leaving you enough time for your personal life.”

“Sounds like you’re upset about that conflict with Bob.”

And so on. Don’t try to fix it. This isn’t the time for fixing things. Just listen. Give Pia the time to express her frustration. You’ll find that the more you show Pia that you’re listening, the more upfront she will tend to be, and the information she volunteers is crucial to exposing your blind spots, ways you’re harming the team without even being aware of it.

So, if manager issues played a part in Pia’s decision, getting her to be upfront about them will help you grow and avoid further unwanted attrition, assuming you’re willing to absorb what she says and make changes accordingly.

Culture

Culture is a combination of team dynamics and team process. Dynamics refers to the personalities on the team, the cohesion between different team members, the amount of pressure the team is under from outside, and the amount of pressure exerted on the team by their manager.

As a manager, you have a responsibility to address team dynamics issues when they arise. It’s your charter to shield your team members from external pressure as much as you can, and apply only as much pressure on the team as they can handle constructively. This is where part of the artistry of management comes in: balancing business needs against team well-being. This means taking some heat from both ends, but, as managers, that’s what we signed up for, right?

The other huge area of culture is team process. Just to make sure we’re on the same page here, let’s define what I mean by “process”: it is the set of daily and weekly rituals and tools the team uses to plan and execute work. Agile vs waterfall, Kanban vs Scrum, and so forth.

So, does your team set their own process, or do you dictate the process to them? Does the team continually evolve process through retrospectives and action items, or is your process stagnant? These are important points to understand to put Pia’s responses in context.

In Pia’s case, let’s say she is unhappy with having to keep track of exactly how much time she spends on each of her work items. To boot, the need to send you weekly “Status Summary” emails has been ticking her off.  
“Why can’t you just pull that out of the daily standups the team is having?” she asks.

The time I spent in Sweden working in Skype taught me that letting the team set and run their process, even if you as a manager have concerns about parts of this process, it tends to work better than imposing a process on the team. Naturally, you’re free to recommend, to argue your point passionately, to suggest experiments, etc., but in the end, letting the team decide what they want to do can head off many of these types of problems.

(The only non-negotiable part is regular retrospectives. To be fair, I’ve never heard of a team that *did not* want to have retros, but in case such a beast exists, yes, retros are non-negotiable. It’s vital for a team to have a forum to voice their concerns. Not having such a forum leads to Pia handing you her resignation letter.)

Dynamics

We’ve mentioned that culture is a combination of process and dynamics, so let’s cover the second part. A very common issue on a team is a personality conflict between team members, and sometimes they can be severe enough to make someone’s life a living hell.

No matter how severe the conflict is (poor meeting dynamics all the way to an HR violations), the fact that Pia comes to you with this problem and a resignation letter should be a wake-up call. As a manager it is your job to be intrinsically aware of the team’s dynamics, and work to quickly head off this sort of negativity. This is obvious in HR-level cases such as bullying or sexual harassment, but may be less so in other cases.

For example, let’s say Pia is in a satellite office and feels like she’s never given room to speak up in meetings. Or let’s say Bob on your team tends to dominate public discourse and has repeatedly ignored Pia’s contributions.

Or let’s even say you have one genius-level asshole on the team who’s making everyone else’s lives miserable.

You must intervene. You should’ve intervened by now. Pia’s resignation letter in this scenario is a vote of no confidence on your leadership.

Take this very seriously if you want to continue having a productive team. The toxic culture boulevard starts with an individual disagreement, meanders into sullen acceptance, weaves through disempowerment and disengagement, and terminates at resignation.

Domain

This is the toughest one to address. By “Domain” here, I mean what it is your team works on day-to-day. Whether you’ve hired up the team by yourself or not, it’s very rare that an employee’s expectation of what they’re going to do when they join the team aligns 100% with what they’re actually doing. A part of it is a hiring manager’s natural tendency to sugarcoat the job description.

Nobody is likely to say “Yeah, expect to spend two-thirds of your time dealing with incoming Sev-2 issues,” but that situation may very well exist or arise after the team member joins.

No hiring manager is likely to say, “Yeah, there isn’t much challenge to what we do here. This job is where people come to take naps.” Yet those jobs exist, whether through organization issues or because, truly, the domain is that boring.

It will usually take a new hire anywhere from 3 to 6 months to figure out if the new job aligns with their need for a challenge. They’re also not likely to be upfront about their dawning realization. They might express a degree of dissatisfaction with their tasks, but it takes a special sort of empathy to distill those sporadic messages into the understanding that your employee is at risk, especially if you feel like you have a good rapport with them, and that they’ve been succeeding in terms of career growth.

There are a few ways to mitigate this risk, but ultimately there’s relatively little you can do. The best way I’ve found is to encourage your directs to be proactive about the sort of work they’re taking on. (I call it driving “Somebody Else’s Problems,” a concept stolen from Douglas Adams’ Hitchhiker’s Guide to the Galaxy. You want to hide a mountain? Paint it pink. Then people will walk right over it without realizing it’s there, because it’ll become Somebody Else’s Problem.)

Having the time to pursue parts of your domain that particularly interest the employee can mitigate their overall dissatisfaction with their domain. But it’s unlikely to fully resolve it. To wit: if Pia discovers she isn’t interested in Security after joining a team working on the authentication stack of your SaaS product, there are few Somebody Else’s Problems within your team’s charter that will keep her engaged enough to stay long term.

Don’t take that personally. Use the learning to screen candidates better next time.

Okay, so now what?

So, you’ve had the conversation with Pia, and she’s told you why she’s interested in leaving. Now what?

First, take off your manager hat for a moment. Put yourself in her shoes. Internalize her reasoning and find out as much as you can about the new opportunity. Do her reasons for leaving feel sound to you? Do they align with weaknesses you know about, or are they exposing something new?

Do you think the reasons are particular to her, or emblematic of larger issues as a whole?  Is this about running away from your job, or running to something better? Would you find the new opportunity interesting? What concerns might you have about it? What would draw you to it?

Have a chat with Pia about these issues. Share your observations and listen to her thoughts on the matter. Don’t think like a manager, for the moment. Think like you’re her friend.

Now, put your manager hat back on. Are there projects on your roadmap that might give Pia the same sort of satisfaction? What about on other teams in your organization? If you’re in a large company and Pia is contemplating leaving it, are there other areas in the company you know that you might recommend as a possible option? Talk through those with her. Obviously, your first priority as a manager is to do whatever you can to address Pia’s concerns and encourage her to stay.

Your second priority is to keep her in the company. (Remember, for this scenario Pia is one of your top performers.) Are there other managers you can talk to about her? Other opportunities within the company you might help her to explore? If her issues are about you or the team’s dynamics, is there anything you can do to address them going forward?

Talk through those options with her. Those conversations should always start with:

“At the end of the day, it’s your decision, and I’ll do whatever I can to support you in whatever you decide.”

Your best approach is to think about the long game. Yeah, Pia might leave your team. But is she going to leave it in disgust or fondly? How is she going to think of you six months from now?

Why is this important? Well, what happens when you move positions and have an opening on a new team, one you know she would enjoy? Would she follow you there, or would she ignore your ping? What happens if a better spot opens at your current company? What happens if she knows someone who'd be a perfect fit for your team?

The business game isn’t about employee retention. It isn’t even about short-term business value.

It’s all about relationships.

So, even when the relationship seems like it’s coming to an end, take the time to build it as strongly as you can.