A newly appointed senior manager at a startup grapples with the charismatic, but often unrealistic, vision of the founder. The manager seeks advice on how to effectively communicate operational challenges, provide constructive feedback, and navigate the founder's tendency to overcommit and prioritize new initiatives over addressing existing issues.
I started a new senior management role at a start up a few months ago and I’m wondering how to parse my relationship with my new boss, the founder. I feel like it’s a classic dynamic in startups—a charismatic “visionary” who is constantly trying to innovate, add new features, oversell to clients, and overcommit on deliverables all while shilling platitudes to the staff about a level of excellence we truly can’t achieve given the workload he’s saddled us with.
Right now we have major operational issues with projects due like, next week and he’s trying to launch a new in-house brand for a spin-off project! It’s impossible to have a conversation with him about real world issues we’re troubleshooting right now without him trying to suggest a new automation, a new integration, a new standing meeting, a new tracker—when really the answer is we need time without meetings to buckle down and get some good old fashioned manual work done. This is what I signed up for, and I suspect just largely how it goes in a role like mine. But this is my first time! I feel like I’m constantly running interference between him and my team as he’s asking us to use tools that are underdeveloped, buggy and require too many manual inputs anyway to be effective. It’s like he’s playacting being a tech founder in an industry based on delivering in-person services. He seems to really respect my expertise, and tells me all the time to give him honest feedback on how he’s doing as a leader, and I’m kind of at a loss on where to start. I actually really love my job, am well compensated, have a great team, and love the work we do. I need him to realize his pattern of quick “solutions” often come with a new platform, new log-ins, and new integration, plus require testing, and present a new vulnerability for things to fall through the cracks. Rather than create efficiency, we’re just building card towers that make us feel disconnected from the work. How do I talk to him about this or throw out some speed bumps at least?), let’s just say I feel your pain. Working for startups can be exciting—there’s always something new happening, things move quickly, people are usually committed to the work and happy to be there—but also draining, especially when a founder is more of an ideas person than an operations expert. In a lot of ways, though, what you’re describing about your boss is a feature of startup culture, not a bug. And I think the only way you’re going to be able to feel like you’re succeeding at work is if you take a step back and realize that you’re not going to solve all of your workplace’s problems—nor should you. That also goes for how you give him this honest feedback that he’s ostensibly looking for. For example, a comment like, “Here’s what I’ve seen happen when we change direction in the middle of a project” is infinitely more helpful than telling him that his attention seems scattered or that he’s playacting at being a founder.I also wonder if your desire to protect your team by running interference, as you put it, is actually making them feel more disconnected from the work, which you say is an issue. Maybe instead of feeling like you need to shield them from all of your boss’s peccadilloes, you could propose that his requests for new features go into a queue that get assessed by the team weekly or monthly. That also cuts down on his possibly manufactured urgency and indicates to him that you have an organized plan to address his ideas.Overall, though, it sounds like your boss at least has good intentions here, and I wouldn’t throw the proverbial baby out with the bathwater because he’s got a tendency to chase shiny objects. It just sounds like you need to put some systems in place that will make life smoother for everyone—yourself most of all.Please keep questions short , and don‘t submit the same question to multiple columns. We are unable to edit or remove questions after publication. Use pseudonyms to maintain anonymity. Your submission may be used in other Slate advice columns and may be edited for publication.Two years ago, I helped my coworker flee what I assume was an abusive situation with her husband. She never gave me many details, but mentioned his temper and the difficulties in their marriage. He was away for work for a weekend, and I helped her move across town to a new apartment in secret with her two small children .For the next year and a half, she seemed to be happy and thriving. Then six or so months ago, things changed. She’s no longer her normal bubbly self, and she’s been missing a lot of work—at least one day every week, but usually two or three. She’s also had two broken bones and a serious concussion in the last few months, plus various bruises that she swears are from sports. A few weeks ago she let it slip that her husband is back living with her. I obviously don’t know anything for sure, but it really seems like he is abusing her. Is there anything I can do to help her, if she needs it? We aren’t close—we shared an office when she first started which is how I ended up helping her move, but she’s since moved departments and we only interact on a professional level these days.Bless you for being such an empathetic colleague, and for actually helping someone who was truly in need and probably felt like she didn’t have many people to turn to. If I had to guess, she’s embarrassed that she’s allowed her husband back into her life, and she’s reluctant to confide in you again because she fears your judgment after you helped her escape last time. I would ask her to get lunch or coffee and just make it clear that you’re there for her as a friend as well as a professional colleague, and you are able to help if she ever needs anything. I would tread lightly not just so that she feels that she can trust you, but also for the safety of both of you. I would also think about what you feel comfortable helping her with if she does end up asking you. Are there other resources at work you can lean on? Do you feel like mentioning something to your HR department would be helpful and not harmful? Does your employee handbook offer any guidance? You might alsoabout what to do when you suspect a colleague is being abused at home—it has some helpful guidelines and language about how to navigate these situations. And thank you, again, for being so caring.Approximately two years ago, I had a nightmare interview experience. I am a trans man, I’m open about this fact on things like social media . I applied to a local company that has strong ties to the community. It’s in a field I have experience, and was a laborer position which I was already doing for another company. Basically when I went in for the interview, the person interviewing me took me into another person’s office so she could refer to me in third person with she/her pronouns the entire interview. I did not react to it, I remained professional and ignored the obviously targeted, discriminatory treatment. Because I wasn’t expecting blatant discrimination in an interview, I didn’t think to record my interview, so I have no proof this discrimination occurred. Lately after joining some 2SLGBTQ+ support groups, I’m realizing more and more that I don’t want them to just get away with conduct that violates human rights and I don’t want this to happen to anyone else.Frankly I’m glad they didn’t hire me after that, I have a great boss currently who I would do anything for who values me and tries hard to make me feel like my work is appreciated. I would be content, but I am really concerned about other people getting hurt by this other company. I had applied because the company I currently work for is too small to have more comprehensive benefits like medical or dental. I am really worried the discrimination goes beyond what I experienced, and it’s a field that definitely attracts a lot of immigrant workers.My problem is two-fold. One, it has been awhile since the event occurred, and two, the connection to the community has me worried that the backlash I’d receive for speaking out about this company would ruin my life. I’ve lived in this area my whole life and I volunteer and don’t want something like this impacting future work prospects or my relationship with the people I volunteer with.What should I do? Also, I live in Canada so my rights as a trans person are protected under the law.I’m sorry that you were treated this way in a job interview. It was unacceptable and unprofessional and should not have happened, and I applaud you for wanting to protect other people who may apply for jobs at this company or already work there. I also understand your feeling like going public with what happened to you could have negative consequences for you and your career.A Supposed “Ally” Did Me Wrong. Is My Plan to Ruin Her Life Too Much? I have two suggestions of things you could do that might bring you some closure. One is to leave an anonymous review on a website like Glassdoor about what you experienced in the interview. Enough time has passed that it’s unlikely they would connect it to you, and anyone who did their research on the company before interviewing there would come across your review and hopefully take heed. The other is to be public about it in the 2SLGBTQ+ support groups that you’ve joined. This would alert the population that is most likely to be affected by this company’s attitudes and practices, and puts them on notice—but in a protected space.Unfortunately I think that worrying about the potential additional discrimination at this company is outside the scope of what you should be concerned about. I see how much you care about others and that this empathy is what’s driving your desire to do something about what you experienced, but I also hope that you will be able to move on from it. I hope that this will bring you some peace going forward.A little over a month ago, I got summoned to HR while at my regular work tasks. I was sat down, and told to sign a paper acknowledging responsibility for the “incident on June 15” and stating that I would “accept consequences thereof, including but not limited to remedial sensitivity training.” I had absolutely no idea what they were talking about. As far as I could remember, that was a normal workday where I logged in, did my duties as a bookkeeper, and went home.
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