Case: The Sudden Resignation

Giff Constable case, management

Last week’s case prompt, to both the executive cohort and the aspiring-executive cohort (senior/director level) in Case Camp, went as follows:

As CPO, you spent 6 months looking for a senior PM to lead up a new effort. You went looking for a particular skillset in wearables, which is in high demand and short supply, and so were excited to land this person. The PM reports to a Director you trust, but 5 months after the PM starts, your Director comes to you and says, “I have surprising and unfortunate news. Our wearables PM says they are resigning. They have another offer, a higher offer with a higher title, from another company.” From your perspective one step removed, you’ve had a positive impression of this new PM, so this is bad news. What do you do next?

Before you read on (and even as you step through the case), go ahead and write down your actions/questions. If you want to jot down your own answers as you go along, open up this Google Form alongside. (Prompt 1)


If you’re like the Case Camp participants, you have lots of questions:

  • why does the Director (the PM’s manager) think this happened and what has been their interactions with the PM over the past 5 months?
  • what’s truly going on with the PM? Is it just a mercenary thing over title/salary or is it something else? (hint: it’s usually something else)
  • what are the goals of this PM and have we truly been aligned?
  • did we set the right comp/title for this person or did we miss something?
  • how was this person onboarded to the company and to the team, and do we have a systemic problem there?
  • how exactly are you going to gather this information?

You also have two planes to think about:

  1. tactical: immediate needs of this situation (can/should this PM be “saved”?)
  2. systemic: what weaknesses in our approach does this situation expose, and how to fix?

If you’re like most, you’ll probably begin by asking more questions in that first conversation with the Director when they break the news. Let’s say you discover a few things:

  • the Director has been generally happy with the PM; yes, the team has been a bit rocky, but that’s why we wanted a senior PM on it in the first place; the team has been getting better — they always had clear goals but now their alignment, execution and communication seems to be improving;
  • the Director has been checking in on the PM every couple of weeks, asking if they needed anything and the PM has been saying that everything is fine;
  • for our company, we’ve got this PM at a correct title and salary level, if you don’t grant an exception for having rare knowledge about wearables;
  • the PM’s goals, as understood, seemed what you would expect: work with good people on an interesting problem (specifically around wearables) and have a chance to get promoted — all of which we were offering;

A few things you also know about the Director: they are relatively new to the role, having been promoted 9 months ago, and have been stretched pretty thin lately.

Okay, now what are you going to do? (Prompt 2)


You might have picked up that the Director wasn’t too close to the PM — autonomy is fine and good, but they described flybys, not regular 1:1s. That’s not ideal. Given that the Director is new to the role, the responsibility for this really lies with you! From a systemic point of view: are you setting the right expectations and providing effective training and mentoring to your managers? On the tactical side: have you put too much on this Director’s plate, stretching them too thin when they need a chance to grow into the manager role?

It’s likely that you want to talk directly to the PM, both to learn more and potentially to sell them on staying. The question is how to do that?

  • A. If you immediately go to the PM, that risks sending a signal that you lack of faith in the Director (both to the Director and to others). Even if you pride yourself on running low-hierarchy team, you have to be careful here.
  • B. You could do a joint meeting, which has the benefit of getting to show the Director how you handle a situation like this. The downside is that it’s intimidating to the PM having to face 2 bosses, not just one, and is unlikely to get them to open up.
  • C. I recommend asking permission of the Director to talk to the PM. When you talk to the PM, you can begin with something like, “I asked the Director if I could talk to you directly. I think you’ve been doing great work so far, so was disappointed to hear the news. Fill me in on what’s going on…”

(Prompt 3)

In this case, the PM still doesn’t open up. They respond, “Thank you so much for the opportunity to work here. I’ve learned a lot getting to work for you. I wasn’t actively interviewing, but got to know this other company last year. This seemed like an opportunity I’d be crazy to refuse.”
    “Well, I understand being excited about an opportunity,” you reply. “Tell me more about why you think you’d be crazy to refuse it.”
    “It’s a chance to lead a wearables team on an exciting new consumer product. It’s a great brand and great team.”
    “Well, I’ll admit that their brand is a bit shinier than ours,” you reply, “but I’d like to think you have an opportunity to do all of that here. You can make a great impact here, you know, and you’ve made a great start already. We’d love you to stay. I’d be happy to hear what you think that might need to look like.”
    They just nod, somewhat unhappily. “Thank you. Seriously, thank you, but I think I need to go.”
    “Where are you in the process with this other company?”
    “I’ve signed an offer letter.”
    “Ah, I see,” you say. “Well, you haven’t left yet and I’d hate to see you go. If the offer letter is like most in our field, then you can still change your mind, but I’m not here to pressure you to do so. I’d like to work out a path for you to stay, and would love for you to think about that as well. Let’s both think about what that could look like and talk again tomorrow.”

Keeping the PM feels unlikely given they have signed an offer letter, but it’s not unheard of. You have to decide if you match or beat the salary and title offer from the other company. What would you do? What are the pros and cons you see? (Prompt 4)

Within our cohorts, we were split on this topic. Some people thought that it would be acceptable to give the PM a raise because the negative impact of losing the PM to the team and an important project justify the outlay. Others thought it could be justified because the PM has a specialist skillset in high demand. Others felt like it would set a bad precedent and could cause downstream problems and resentment with the rest of the PM team. If the PM was truly being mercenary, you might be in the same spot in another 5 months.

For my part, I would be unlikely to match a competing offer. Different PMs all have different strengths and weaknesses, and I don’t believe in paying more to someone who negotiates more aggressively. I believe in having fair salary and skill bands that apply equally to the entire team. If the market has moved, I need to change my bands, not make one-off exceptions. I’m okay losing a candidate because I’ve seen the unfairness, bias, and subsequent morale problems that come with a “get away with what you can” approach to pay.

What you can do, however, is paint a clear picture of what the PM needs to do to get that promotion to the higher title/salary, and perhaps set expectations (not promises) around a likely time frame. But remember, as CPO you have to decide whether you do this or have your Director do this.

If you’re like me, you’re still thinking, “Even if the PM didn’t say anything, there’s got to be something else going on here.” The trouble with getting to the CxO level is your information flow from below becomes non-existent. People don’t tell you what is really going on. Nor can you invisibly observe the team meetings — people’s behavior changes when you are around, like it or not.

One possible solution: do you have another PM who might know what is going on and who will open up to you (since PMs often vent their frustrations to each other)? Or, is there someone else on the departing PM’s team whom you can talk to? For the latter, I might start with the designer, as they would be a close partner to the PM. If you are beyond startup size, you will want to give a heads up / ask permission of the design manager.

Note: these little permission steps are more than niceties. They preserve the mutual respect that is needed with your direct reports and which you can break with careless “skip levelling”.

In this case, the designer says this to you: “Yeah the rumor is already swirling that the PM might be leaving. I’m bummed. I liked working with them. The team was just getting its feet under it! I don’t really understand it.” When you press for friction or conflict anywhere, the designer admits, “Well, the PM was arguing a lot with J, our engineering team lead. I mean, we’re all used to J – they mean well, but they are really passionate and have strong opinions and can sometimes come on very strong.”

The engineer in question reports up to your peer, the CTO. At this point, you know my question: what’s your next move? (Prompt 5)

Most likely, you start with your peer, the CTO. You ask if they know anything about the relationship between the PM and the lead engineer, and they say, “Unfortunately I don’t. The lead reports to one of my VPs and I haven’t heard anything. I should note that this is one of my best engineering leaders. Yes, they can be stubborn and opinionated, but they’re not a jerk — I don’t allow jerks. I think you and I both know that they’re one of the people we can really count on to deliver something of technical quality.”

The CTO wants their VP to talk to the engineer before you or your Director does. The VP comes back to you and says, “Well, I spoke to J. They were surprised to be the cause of a resignation. They acknowledge some of the arguments — apparently they have been butting heads over speed versus quality — but said they would be willing to adjust their style and try to work better with the PM. They do like the PM, even if they think some of the PM’s instincts are going to get the project into trouble.”

At this point, while you might have some further investigations in mind, let’s say that you sit back down with the PM. What would you say? (Prompt 6)


Here’s what I might say:
    “I’ve been thinking about the situation here, and I’ve learned that you were having some difficulty with J on the team. Was that part of your reason for wanting to leave?”
    “I guess it contributed, yeah. I tried to resolve it, but didn’t make much headway,” the PM says.
    “It’s unfortunate that it got to this point. J does like working with you, and is willing to improve their style and develop a better working relationship. If that doesn’t work, we can consider remixing the team. I also think we, in product leadership, bear some responsibility for not onboarding you better into the team and perhaps for not laying out better ground rules for how strong differences of opinion should be handled and resolved. So we have some thinking and improving to do. I’d still like you to stay with the company. Have you thought about what that could or should look like on your end?”
    The PM shakes their head.
    “I have,” I say. “You’re on the right project — wearables is what you want to do, and it’s really important to the company. I also think you’re at the right salary and title for your level, but you should be going over that with your manager at least quarterly. We do rolling promotions here, so when you level up, you level up. We want to promote you, but we have a system that keeps everything fair in our organization and attempts to minimize bias, at least as best we can. We don’t make exceptions, and I hope you see that’s a better system to work within.”
    I continue, “I think there are areas for us to improve on our side. You should be having weekly or bi-weekly 1-on-1s with your manager. The Director agrees that should have been happening. If you felt on your own, that was not their intention. As I mentioned, I also think we can improve some things around team onboarding, building team empathy, and how team disagreements get escalated.”
    Then I get to the part about what the PM needs to do: “That said, I think there are some things for you to think about too. The most important is asking for help. This is as essential when you are an executive as when you are a brand new PM. Self-sufficiency is great, but only to a point. Asking for help is a sign of strength, not a sign of weakness. And we really could have helped here if we had known what was going on. In other words, it’s a two-way street. Your manager needs to paying more attention, but you also have a responsibility to bring your big challenges to their attention.”
    I conclude: “I know it might feel like a foregone conclusion, but it’s still very possible for you to change your mind and stay. I think there are opportunities for you to do great things. I think this has shown some opportunities for our company to grow, and for you also to grow. I’m hoping we can do that together. Think on it, and let me know later today or tomorrow.”

The next morning, the PM tells you they appreciated your comments, but that they are indeed going to leave. You accept your lumps, thank them for their time with the company, and focus your efforts on improving things so you don’t walk into this again.

Some takeaways

Here are a few questions to ask yourself about your own situation:

  • Hiring: are we being clear about our culture and values, and what people should expect when they come to our company?
  • Onboarding:
    • how are we onboarding people not just into the company but also into their teams?
    • do we have a diversity issue in terms of onboarding and assimilation into teams?
  • Management:
    • have we provided the right training and expectations for the frequency and rough structure of 1:1s?
    • are we setting conditions where employees feel comfortable for help?
    • Are our managers putting responsibility on the employees to come to 1:1 with an agenda, and to raise challenges? (put another way, do we treat employees like adults or children? People will often act as you treat them)
    • Should we run periodic “stay interviews” to keep our finger on the pulse of why people are staying, yet also spot the issues that could tempt them to go?
  • Teams
    • how are teams making decisions and handling disagreements? (note: I’m a big believer in escalation paths for the latter, rather than role-based decision “owners”)
    • How are we measuring the informal temperature and effectiveness of our cross-functional teams? Can we experiment with something lightweight?
    • can we suggest a menu of ongoing empathy/relationship building exercises to help teams come together (for example, user manual to me)

Final thoughts

I hope this case was interesting. Writing it up is certainly harder than talking about it live! The PM job really changes once you become an executive, and while, yes, you get to work on product strategy, your success really happens through other people.

As you can see, even a relatively simply situation has a lot of nuances. Seemingly simple decisions have downstream effects. We also have to be cautious with our own biases. Did, for example, you overlay specific genders on the case?

I should also note that while this case didn’t veer into the really tricky (and awful) territory of harrassment, sometimes that will happen. You need to make sure you bring in HR right away.

I can’t say that I would do it the same way every time, as context matters so much. You might have made different moves, and I’d love to hear what/why in the Google Form (Prompt 7) or over twitter (DM or open) or email. And if you are interested in Case Camp and want to learn more about the program, click here.

Top image from arash payam on Unsplash

p.s. thanks to my former colleague Brian Fernandez for the suggestion of adding the form prompts.