The first time I met with a senior manager who would later become an advisor, she asked me what my philosophy on management was. I had no idea. Get shit done? Don’t screw up? She told me that her philosophy was to take care of her people no matter what. She said it flew in the face of everything most management books and training say. Which is that your responsibility was first to the company and then to the team. She didn’t care and said that’s what made her so successful (and she’s crazy successful). She asked me what my philosophy on testing was and I gave her a long rant (which I will write up one day). “If you have such a deep philosophy on testing, why don’t you have one on management,” she asked me. She’s right.
Thinking about my philosophy it boils down to “be a person first, manager second”. First, I make sure I behave as a thoughtful, ethical, and moral human would. Then I worry about all the other stuff. Or at least I try. Managers should think about their relationships in years, not weeks. I was thinking about that recently as I've gone through some unusual situations. I’ve had quite a few of them in my career so far. Blog posts, books, and manager trainings will only get you so far. I thought I could retrospect three situations and how I might handle them according to the “be a person first” mantra.
Most startups will write down some policies to govern situations that apply to everyone. Things like parental leave, vacation time, expense rules, unique benefits, and many others. Inevitably, someone who reports to you will come and ask about an ambiguity with a policy. You’ll have to weigh the benefit to the person and the precedent that this might set. You'll also have to think about whether you’re being fair towards everyone and who else this might impact.
Someone might ask for time off that you can’t grant because of a tight deadline. They might ask for relaxed rules around work from home (we’re talking non-COVID times here). You might find yourself in a situation where they are in the wrong. Yet deciding against what they’re asking might have serious repercussions on them.
I know of another manager friend who had a difficult time when an engineer forgot to ask for vacation until the last minute. That engineer had already spent thousands of dollars on travel expenses. What do you do in that case? Other people on the team are going to be impacted negatively if there is a deadline. It’s not the team’s fault, why should they suffer? And what message does this send to the rest of the team about the company’s policies? Are you going to damage your relationship with this person who you have to say no to? What if they decide to go anyway? You or someone else in leadership could be in the wrong for not setting expectations up front? I’m sure everyone has their opinion and there are so many nuances to consider. This is where my philosophy kicks in. Be a person first.
First, take yourself out of the mindset that you are part of the issue. I know plenty of managers who would feel hurt or a threat to their authority. That’s not the issue right now and if you make it about that, you’re only making a bad situation worse. What is the best outcome for everyone except you? I’m not talking about the company as a whole but the people in the company. Can you find some solution where everyone compromises a bit? Maybe they still go on vacation but they end up working for part of it? Maybe you talk to the team and figure out a way for that person to make it up to everyone (like taking on-call shifts over holidays?).
Make sure to include the person asking in your thought process so they understand what happened here. You want them to understand the burden they are adding to the team so they’ll be open to compromise. Trying to shield them from the consequences, even if you’re doing it to be nice, only hurts them. You'll be setting the wrong expectations in their mind for next time. Sometimes it’s not possible to find a solution and you do piss that person off. It’s happened to me. I’ve had to say no and it never feels good. My hope in every situation is that they understood why I was saying no and that I was consistent in my decision making with everyone.
Afterward, you want to make sure they understand the policy for next time. You also want to make sure everyone understands this. You don’t want to create an unfair or biased culture. One where the “good” people are hurt for following the rules and the “bad” people get away with not following the rules. You might not pay attention to it but the folks who see their peers not adhering to the existing policy are very aware. They will get upset and likely won’t say anything until it’s too late. Specific of which..
Any time someone has given me notice that they are leaving the company, it’s been a huge test for me to react with compassion and thoughtfulness. In the moment, my first thought is how did I fail? I also get doubtful about my own skills as a manager. I’ve seen other managers turn negative and try to make the person giving notice feel bad or guilty about “abandoning the team”.
Your goal at this moment is to treat that person with respect, understand their feelings, and their new opportunity. Then talk with them honestly but respectfully about their options. There are many differences of opinions on whether it’s worth trying to save someone who has given notice. I won’t go into that now but from experience, it is possible to address the underlying reasons and keep them. Multiple times I’ve seen that person go onto a long and happy career at the company.
What you don’t want to do is make them feel bad in any way. Congratulate them on the opportunity. Tell them you’re excited for them (and you really should be!). Make sure they feel comfortable telling you why they felt the need to go looking. Sometimes you can’t solve it. For example, if they are looking for a role or domain you don’t have available. Sometimes it’s comp or company level issues that are out of your control. Sometimes you didn't do a good job and they are specifically leaving you. Take that as a wake up call to improve. Ask them for feedback on the team, yourself, and the company. Ask them what, if anything, you or the company could have done differently next time. Ask them when they started looking and if anything prompted it. Don’t get upset or pushy if they don’t feel comfortable sharing with you.
A few things you definitely should not do (and yes these are real examples). Tell them they don’t have control over the end date and that the company will decide when their last day is. Tell them their new company isn’t good or share gossip that negatively impacts their feelings towards their next opportunity. Tell them they are making a big mistake. Shut the door on future opportunities with you. Get angry or emotional. Start telling other people in the company about their departure in a negative way.
If you find yourself having a hard time controlling your feelings then it’s completely fine to say something like “Thank you for letting me know. Let me go talk with [another leader] and get back to you about a plan. Please don’t share this before we’ve had a chance to talk again”. Then end it there and go gather your thoughts.
After you’ve mutually agreed to an end date, make sure they feel comfortable winding down their work and making time to say goodbye. Folks who have been with the company longer will have more people to say goodbye to. You want them to feel like they can and should get goodbye coffees or meetings. Celebrate their work and their contributions publicly. Make sure they feel good about the team. You have no idea what kind of impact they might have on others if you leave things negatively. Most of all, make sure you ask them for feedback near their last day. That final feedback is some of the most honest you will get from someone who reported to you. Get their contact info and stay in touch. You may cross paths again. Follow up later to make sure they are doing ok in the new role. Once their manager, always their manager.
Not My Person
The last situation involves a tricky case where someone on a team that is not yours needs to hear tough feedback. It might be a manager or a tech-lead that is not a good leader. It might be an individual contributor that you notice needs some tough love. Maybe you’ve tried to give their manager that feedback but they’ve disregarded it. Maybe their manager has tried and isn’t getting through and could use some support. Sometimes this person needs to hear it from an unbiased third-party.
So how do you give someone feedback where there is clearly a power dynamic (you're at a more senior level) but not a manager relationship. Many people would actually not give feedback at all. That’s unfair to the person. True that some people can’t be taught. But many people are only a few pieces of honest feedback away from turning a skill or role around into a strength.
So let’s give a more concrete example. You’re in a meeting with a manager from another team. They should be owning the meeting, advancing the discussion, taking notes, giving everyone room to speak, and making sure we stay on track. But for whatever reason, they are either reluctant to lead, ignoring parts of their responsibility or they are veering off track. You may or may not have your own people in that meeting. It doesn’t matter. So the meeting is a few minutes in and you realize that this is going off the rails. Maybe you are very invested in the outcome of the meeting or it doesn’t matter to you that much. Either way, as a leader, you want that time to be useful and the meeting to be a success.
Here’s what you don’t do. Take over the meeting formally. Criticize the other manager publicly. Say something about this meeting not being useful. Stay silent in a way that makes it clear you are unhappy. What can you do? Try asking probing questions that get the meeting back on track. Sometimes I outright lie and say something like “[Manager], weren’t you also talking about X previously”?. If the manager is at all smart, they will jump on this lifeline of advice without making it seem like I told them what to do. Sometimes you might know that someone else can help steer the meeting towards a useful outcome but they aren’t getting the space. That’s where you can use your voice to amplify their voice with a “[Quiet Person] might have some insight because of X”. If you remove your own ego from the equation and don’t need credit, there are many tactics and tricks you can use to incept an idea into someone else.
When a meeting like this is going poorly, I’ll usually take some notes to myself on things that could have been better. Afterward I’ll message that to the person privately with a prompt like:
Hey [Person] I like to give direct feedback when I can. Here are some thoughts from that meeting. I'm happy to talk through them if you want. Hopefully you will find this useful. [Notes Here]
If they are someone that wants to grow as a professional, then they will be receptive. If not, then possibly you hurt someone’s feelings. I’m ok with that because more often than not, this works. Several people have actually followed up with one-on-one meetings to talk more about my feedback. I love it when I later see someone actually use a strategy I taught them in a future meeting. I think it all starts from a place where you genuinely want to help that person. Most people can tell when you’re giving feedback as a performance vs when you actually care. If they really take it to heart, tell their manager so they get some praise for the turnaround.
So that’s it really. Don’t just manage someone or a situation because you’re a manager. Do it because you care about them and their success. When you strip away your own feelings and the need for credit, you’re left with their growth to think about. Just be a person first. Everything else about being a good manager will follow.