Dear Swim Club, my boss is the head of our marketing team. She has about 7 direct reports across a US team. It's a busy, high velocity environment, with really high expectations. She is really great as a human. Personable, cares about us, and seems to go to bat when it comes to promotions and pay increases. I was here when she got hired, and she's a big improvement from our last head of marketing. But…I notice things she misses and I end up dealing with problems that are really hers to deal with. She also freezes up in meetings when someone asks her a strategic question. I can see she really thinks about the question and how to respond in the meeting, which I thought was just her being thoughtful and not rushing to a response, but now I realize she legitimately doesn't know how to respond so just hopes someone else jumps in or it gets forgotten. I don't know what to do with this. She's pretty approachable but how do you share this feedback. Or, what is the feedback I'm trying to give to her? I feel a bit confused and conflicted. I get the impression she's not being taken seriously by her sales counterpart, and I think certain pockets of the marketing team are starting to notice too. I feel bad because she's a good person but doesn't seem the most qualified.
Thank you for this question, and I want to start by saying this isn't the first time I've heard someone describe a situation like this. In fact, I've experienced a similar situation early in my career where I felt someone in a senior leadership position, with certain decision making responsibilities, wasn't ready for what the role and team needed.
What made matters worse is this individual (I believe), also knew they weren't ready. I ultimately felt a deep sense of empathy for them because who likes to feel like they aren't good enough? Or ready? Or worse… an imposter. I think most of us want what's best for the (good) people around us.
Back to your question. It sounds like this person needs help through awareness. You sound like a caring, empathetic individual who wants to help, but are unsure exactly what that looks like right now. Let's break this down into a few components.
First, acknowledge what is and isn't your responsibility. Doing your boss' job is not your responsibility. Compensating for her is not your responsibility. Nor is protecting her. This might sound cold, and I don't intend it to be so. But she has her duties, and you have yours. Swim lanes.
What you'll need to do in your mind is be really clear and redraw the boundaries of roles and responsibilities. Some folks I've coached feel guilty setting these boundaries. Others just want to be helpful and go along to get along. I never think this is a good path to take. It doesn't help anyone, and the person compensating ends up becoming resentful… and that never ends well.
It sounds like the balance of responsibility in your relationship (and hers' with the team and business at large) are out of sync. You're not trying to punish your boss or make her hang herself. It's more about being clear with yourself on what is within reasonable expectations and what is not.
Helping cover for your boss or colleague from time to time is totally fine and just makes you a solid teammate. But when them dropping the ball and needing air cover becomes a repeatable pattern, that's a signal telling you something is wrong or not working as it should. Afterall, everyone plays a part within a system.
So once you do redraw the boundaries about what is and is not within your jurisdiction, I find that determining your next steps are a lot easier, and more clear.
Second, try to reflect on your relationship and determine where your trust battery is at. Shopify used this concept of a trust battery to articulate how much good will and trust a person has on day 1, and it always started at 50%. The other 50% is trust the individual had to earn over time, through how they built relationships, through the impact they drove, and the overall kind of reputation they built.
Once you've assessed where your trust battery is, here's how I'd approach the conversation. Could you book a sync with your lead tomorrow, and candidly ask her "How are you doing? Like really doing in your role? How do you think things are going?" And could you share candid feedback like "The reason I am asking is because I've observed a few times that you appear to be caught on the back-foot, here's an example…"
This context on the state of your relationship is important. It determines which posture you show up to that meeting with. Some folks reading this may say I'm overthinking this — "just give the feedback regardless!" But I've learned that most people I've interacted with dread and avoid giving feedback to peers and direct reports in the best of circumstances, let alone when a relationship isn't very strong.
When you have that sync to give your lead some feedback, I'd suggest coming from a place of care and empathy, not accusation. Tell her your goal is to help her — not to help do her job! But to help make her aware of some blind spots. She may surprise you with her response as to why she's struggling. Let's role play two of the most obvious possible responses.
Scenario A (Best case scenario) — If your lead's response is along the lines of contrition or acknowledgement that you're right, then that's your window to build upon your relationship.
Double down on empathy and care. Actively listen to her response. Listen to what she admits to, as well as the steps she says she will take. The desired outcome in this scenario is that she takes responsibility to make change based on the tangible examples you've given her.
For example, if she's caught on the back-foot with Sales in a live, synchronous meeting where she has to give a response, it's ok for her not to have the right response in that moment, but it's incumbent on her to have it eventually. Can she agree to circle back with her peer by the end of the day? The next morning? That's what closing the loop looks like.
What you're seeking is closure, ensuring that she is taking responsibility for decisions within her sphere of control, otherwise you and others feel helpless and unable to take the next step.
Scenario B (Worst case scenario) — If her response is defensive, don't fight her, don't push her.
I've learned that when someone is in a defensive posture, they no longer hear what you're saying. You could wait and see what happens over the next few days to reengage or to see if she comes back around to you.
She may just ignore the conversation and never address it. She may need a cool down period, and then come around. If you feel like this person will not come around, and they will dig their heels in, it might be a good time to check in with your HR business partner (HRBP), or whoever from HR has been assigned to your team.
If that's the case, then share your observations with HR. They will ask you if you've given feedback to your lead, and you can now say yes. It's out of your hands at this point. And the reality is, some HR teams may do nothing about your feedback. Or, some may follow up with your lead. I've found that it depends on the maturity of the business and their risk tolerance.
I can't say what's going on for certain with your boss, but if you were my peer or someone I worked with, the course of action I'd recommend is to jot down a few examples where you felt your lead wasn't showing up well, book a call with them, be calm and prepared (use an LLM to coach you on flow as well as ways to deliver feedback that are clear — I do this all the time), and remember: you're validated in what you're observing. Ultimately, this feedback will help her grow.
I also want to say that you're demonstrating strong leadership skills. In any leadership role, making hard decisions that drive deep transformation (of a business or a person) is the cornerstone of what differentiates between an individual contributor and a leader.
Right now, you're in a very challenging position. Some people would ignore it and live with it — which is totally an option for you FWIW. It will boil down to your tolerance level, and where you wish to expend your energy. If you took the time to write in to Swim Club, my gut says that you're likely ready to take the hard but rewarding path.
Good luck!
