Am I the problem?

Hi everyone. I really struggle with managing reports who need a lot of structure, because to me, micromanaging is the highest form of disrespect.So I'm looking for some resources on how to manage someone who needs frequent check-ins, help structuring their day, and to-do lists that we create together. As someone who's extremely autonomous and self-directed, and excels in ambiguous situations, I personally find it insufferable when my higher-ups try to give me direction that's anything more than high-level guidance. I'm really struggling with one of my (fulltime) reports in particular because he isn't productive unless I'm (for all practical purposes) micromanaging him and keeping himself accountable by showing small bites of progress throughout every workday. He seems not to mind, or possibly even like this structure, but I'm having trouble knowing where to draw the line. And at some point, it ends up taking a lot of my own time to be doing this too. For months I was giving him much too much freedom and his productivity was really low. This stressed him out and it stressed me out too. Finally, for the last month we've been doing a system where he and I write out word for word what he'll be delivering during the week, and checking off the boxes as he goes, and this system is working better, but I still personally struggle with how much I should check in on him to keep him on track. Whenever I ask him during the day how things are going, he brings a bunch of things to my attention that he's blocked on. It's almost like when he's stuck, he's just not doing anything! And that he doesn't know how to ask ambiguous questions (like when you're stuck on something but you don't really know how to go about getting yourself un-stuck). And, when he does ping me for a question, if I'm in a meeting and I can't respond right away, I have a feeling he just stops working on stuff until I answer, which can sometimes be hours...instead of working on something else in the meantime. Sorry if this wasn't very structured. Any ideas would be welcome. Is my management style the problem? Is he the problem? This is my first report so I'm much more inclined to think I'm the issue here, and I just want to find ways to remedy this situation.
Obviously, I don't know if this would work for your situation, but this is how I have handled it in the past. 1) have an uncomfortable talk about what changes you need to see, but let him know that you are confident he can do it and that you will help him. Tell him you will have weekly meetings until he has adjusted (sounds like you are doing some of this, but it is unclear if it is with the understanding that the outcome should be changed behavior). Under this new regime of you guiding that behavior change 2) Give the guy a daily goal (this should be temporary) 3) tell him what to do when he is stuck; specifically "help Marcy with reorganizing the stock room by reorganizing the stock by expiration date" or "rename all of these files with the date in a standard format"...or whatever. Something to make sure his productivity doesn't dip that hopefully moves the company forward on a task that has been neglected. 4) have a daily check in on his progress. Use a standard format: achievements, blockages, and plans for tomorrow. Respond with exactly what you need him to accomplish the next day. I literally had to say "respond to this email to get the delivery date" "forward that message to the boss. if he doesn't respond, follow up after lunch by visiting his office." etc. 5) stick with the weekly meetings where you focus more on his professional development and less on specific tasks. You already have daily updates on tasks. 6) when you can find the time, rather than answer his question, tell him how to get the answer himself; suggest a relevant publication, or webinar, or person to ask. I hope this helps. He may hate it and leave or he may grow up and get it won't know until you try. I had to do this once with a bright recent graduate and it was uncomfortable at first, but she really rose to the occasion and stared handling things like a boss once she was clear on what needed doing. It only took her a few meetings before she was on track.
Sounds like it's just a bit of a mis-match in communication/management style - and that's fine. But you're going to have to let go of the idea that everyone will want to be managed the way you want to be managed, I'm afraid. Honestly, I'm really struggling with that myself this year. Especially during quarantine/remote work this year, I've had to err on the side of over-communication vs under-communication. It has felt a bit ridiculous, but it has objectively helped.From what you're saying it sounds like he implicitly wants more management but I'm not clear on if you've actually *had* a conversation about management styles and time-management systems, prioritization etc. So that's step one - kick off a series of conversations. It sounds like you need to ask what his preference for management/amount of structure would be and maybe review how this year has gone for examples. Then, set any boundaries (for yourself) and expectations (for him) on what self-management you'd like to see coming from him and what it would take to get him there/what supports he needs. The end of the year/new year is a great time to have these conversations! If you want him to take more initiative in setting tasks and priorities on an ongoing basis, that could be tied to goal setting for the year. Acknowledging he wants structure might help open the conversation to having him help build that structure: he can build routines and checklists, or start to work on procedures (things like if he has x question, go to y resources, then z if y is unavailable.) From there you've got an opportunity to set some concrete goals/deliverables: by month 1, weekly checklist set up with one process document by Q2. By Q3, maybe three more with a broader calendar and he learns to train on checklists for new people and thus also builds speaking skills or it's tied to whatever other skills he's looking for help building, etc. Separate from the prioritization/to-dos might be explicitly talking about what your expectations are when he's blocked. Feels like a separate frustration from what you wrote. It's not OK if he's just... not working, but he may need that spelled out and he may need help thinking through what tasks he should be doing, and have it explicitly told to him that this is the kind of behaviour that will hold him back from career progression. (Are there particular back burner projects he should be working on? Is there a second person he could go to or a resource if you're in meetings?)TLDR is basically... talk about it all explicitly, and make sure it's understood. Easier said than done. Good luck, I am right there with you learning this all!
OH on boundaries I mean on specifics like - where is the line for updates: would you like a daily or weekly update via email or slack vs a blow-by-blow, is there a shared sheet/list you can set up or an internal project management tool you could review reports on together? Would weekly time sheet reviews together help, tied to a goal of better prioritization/productivity from him? Is he not getting 1:1s with you, or certain resources/access to others? Is it a confidence thing that would be helped by him writing weekly summaries talking about what he did? Also: is he working this way with anyone else? Have you solicited feedback from other managers interacting with him? They may have built systems that work well for them you can adopt. You'll have to do a bit of thinking/groundwork before going to him, but it sounds like you want this to be collaborative. Is there specific time dedicated to coaching him like this? Can you set some aside? Take all of this with a massive grain of salt. I've been pretty focused on similar issues for the last four weeks, ha, and I'm cribbing heavily from some training I just went through. (Manager tools is a bit outdated but worth checking out their podcast! Good foundation.)
Learning to manage is a challenging skill - I agree a lot with, Leilanigl - the problem isn't really with either of you so that presents the opportunity to be a united team against a problem (a management relationship that doesn't seem to be working for either of you atm). Another thing you may consider is experimenting with a coaching approach to your conversations - most people can solve their own problems when they know they are empowered to do so. If your direct report is younger (or not but I see this more in younger employees) they may be afraid to take the wrong action and wait for you to move forward to protect themselves from mistakes - especially during a pandemic where people are overwhelmed by uncertainty. Knowing where the line for decision making is tends to be negotiated over time and they may want to defer more toward you making decisions. You could also have other conversations around psychological safety and what would support them in taking appropriate risks and helping them to trust that you have their back. One book I like about how to have coaching conversations is Helping People Change by Boyatzis Smit & Van Listen. Very approachable in how to get started. is hard for me to imagine that the behavior you're describing from this direct report is meeting expectations for his role. So, I'm going to work with that assumption, that he is not meeting expectations for his role, in sharing my thoughts. If his behavior is totally to be expected for his role/level/tenure then...that's a different conversation, but, again, I'd be surprised at an organization that could support an employee with the behavior you're describing. Okay, so you have an employee who is not meeting expectations. Have you told him that? From your post, it sounds like you haven' sounds like you have an employee who is not meeting expectations...and you keep putting new structure in place (structure that is exhausting and unsustainable for you; structure that is okay to maybe like-able for him) and *hoping* he's going to see there is a gap. He cannot see that gap. You are filling it. From his perspective, there is no gap. Again, I'm making assumptions, so apologies if I'm getting something wrong! But - it seems like this part *is* your problem. You're setting expectations with your actions - that you help point him in the right direction, that it is okay if he is blocked and he can wait until you ping him throughout the day, that you'll give him crystal clear step-by-step instructions on how to approach problems - and not *setting expectations*. He may actually, totally incorrectly, believe that he HAS to check-in with you before he takes action, and that he HAS to wait on you to reach out because you always do. That wouldn't be that wild of a takeaway given the behavior you're modeling for him. This is exhausting and frustrating for you, understandably. It is also a recipe for longer term disaster for you both when you inevitably have to give this person a negative performance review and they are genuinely and sincerely blindsided by a bad rating because they had no idea you expected them to do all the things that you are currently doing for them *and* they're going to feel like you didn't give them the opportunity to do those things because you were doing them! So, you need to have a conversation about expectations for his role. Your entry point is something like: "Hey, I want to talk about what success looks like in this role and areas where you need to make some changes to be successful. I'm here to support you and we can partner on how you make those changes, but the expectation is that you can do much of your role without my direct involvement." and then you talk about the real, concrete expectations for the role (if you don't have standard role expectations, well, again, different conversation...but I'm hoping you're not in this boat!) At some point, you'll have to say something to the effect of: "Right now, there is a gap between your performance and what success looks like in this role." or "right now, you are not being successful in this role." or "right now, you are not meeting expectations for this role." You need to say it clearly and definitively, it is the only way someone will hear it (even then it may be hard to get this across). After getting that part out of the way, you need to provide concrete examples of where expectations are not being met. So, for example, you may say "Someone succeeding in this role will be able to take a project like Project X (use a real example this person is familiar with) and move it forward with no additional guidance from me. They'll proactively identify stakeholders and schedule time with them to align on next steps. They'll proactively communicate an accurate status update that they create themselves." or "Someone succeeding in this role will proactively work to unblock themselves - say, by searching the wiki to find an answer about a procurement process, or by reaching out to a peer who they know has gone through the process before. If they try those things and cannot get unblocked, they'll proactively reach out to me, rather than letting the work sit and be blocked until I reach out."This may have to be multiple conversations, because it can be a really hard message for someone to hear, especially if they think they're doing alright against expectations. You may get push back or confusion from your direct. I find roleplaying SUPER helpful for this kind of thing...not necessarily to get to an exact script, because you can't predict someone's response, but to get the muscle memory of delivering hard messages. You'd be amazing how much your heart rate will spike right before you say the phrase "you're not meeting expectations" even when you're saying it to a friend or a peer! From there...oh man, there are a lot of different paths. I'm I am so happy to talk about this more, over VC or in chat, so definitely let me know. Ideally, your direct hears the message, internalizes it, and appreciates the clarity - then you two can partner on an action plan for their growth (which includes you giving them the room to fail for real and feel the consequences!). I hope this is helpful and wasn't totally in the wrong direction! Definitely happy to chat more if you think it could be useful.
I think the goal here is to get your report to self "micro-manage". It sounds like he needs a high level of structure and organization, so think about the areas in which you support and guide him - writing out his to-dos, working through issues and blockers, etc - and give him objectives to take this work on for himself. Be clear that this is an expectation of him. He should start every day reviewing his own to do list. He should be able to identify work that needs to be done and accomplish it himself. I'd formally add this as a quarterly objective for him.Provide him with frameworks but give him the ownership to complete the analysis (i.e. blocker identified --> source (e.g. IT, lack of resources), potential solutions (short term and long term, tactical and strategic), points of escalation, dependencies and impacted areas, length of delay, etc) --> communicate proactively around blocker and suggested remediation). Perhaps working out of a shared working doc would help him devote time to this, knowing you have access and can go in, comment, and make suggestions. When he struggles with this new process, probe him with questions for him to figure out how to address the problem, breakdown projects into chunks of work, etc. Ask him "what's the next step here?" don't just tell him the answer so he keeps going to you. Help him become more self-sufficient so you don't have to continue to hand-hold him, which takes you away from your job and priorities.Additionally, if you have other direct reports, try to get them to work together, help each other, and learn from each other. If he sees a peer performing in a more structured, self-sufficient, and proactive way and getting positive feedback, he may be more motivated to improve his performance and think for himself.
There is a lot to unpack here but I wanted to go up a few levels first.What is the job? Is it a job that is structured and repetitive or is it one that is complex and ambiguous?Is this person actually skilled at the job? Have you discussed what about this highly detailed structure is making them feel ?There is a lot to unpack here but I wanted to go up a few levels first.What is the job? Is it a job that is structured and repetitive or is it one that is complex and ambiguous?Is this person actually skilled at the underlying job? Have you discussed what about this highly detailed structure is making them feel more capable? If you want to chat more feel free to reach out.
I'm so grateful you posted this question! I'm running a startup and managing people is still a bit new to me so I really appreciate your question and all the answers I can learn from!One thing that has been helpful for me so far, is creating one-pagers/memos for different projects I want them to work on (I usually only do this when people just start out). They have the feel of a homework assignment which seems to be effective for employees that are recent college graduates. In this document I include:- Project title (e.g., build this webpage about X)- Background (why this project matters to the company)- Goals (the final deliverable/product)- Timeline and Deliverables (setting deadlines for project milestones and specifying what specifically you want by those deadlines)I write this up, sit down with the employee for maybe 15-30 minutes when I issue the one-pager for each new project, and see if they have any initial questions to get started. I've found this exercise helpful for myself as well as it makes sure I'm doing my job of setting employee goals and expectations well, and it helps makes sure we're all on the same page. About your question "is it me or him?" here's a test I use to evaluate my management skills and my employees' performance: if I had to fire this person, would they know exactly what they were fired for? If the answer is (A) "no", I as the manager didn't do my job and someone else is getting fired for my poor management. If the answer is (B) "yes", then the employee didn't do their job and that's why they're getting fired. The goal of a manager is to make sure the answer is always B. (based on this test, I -- a new manager -- usually have a lot to improve!).
Replying here as someone who has been on the other side of this!When I joined my current company, although I had a background in the role, there were a huge number of areas that were new to me - e.g. hardware products, where I'd only worked with software before (and therefore operations/logistics/shipping/returns/manufacturing were all new to me). As a result, although in some areas I could happily dive in and just get on with the work, in others I was really unsure how to proceed so needed much more 'handholding'.Things that I found helpful:- each week as a whole team, we agree our priorities for the week. We tend to keep it to 3 things, and at the end of the week we report back on what's gone well and not well (even the assumption that something will have not gone well is helpful in making you feel reassured to take some risks!). Keeping it to 3 things forces you to prioritise, and to step out of the detail a bit too - skills I struggled with initially, as when I panic, I would just dive into the details rather than taking a step back- having a weekly 1:1 with my line manager. We chatted through my progress, any blockers etc. mid-week- being told by my manager to reach out if I'm stuck - she explicitly said 'it doesn't matter if I'm in a meeting, email/slack the question, and I will get back to you when I can'. I think the thing that really stuck with me was that I was trying to be polite and find 'the right time' to discuss things with her, but she said 'once you send a message to someone, the ball is in their court. Until you send the message, they can't do anything to help, but once you've sent it you've done all you can so can guiltlessly move onto the next thing while you await a response'. I had been trying to do the right thing, just going about it all wrong- handholding the first time I do something, then stepping back a lot the next time. For example, I had to write a certain document I'd never written before. We did the first draft together, with me asking questions and my manager pointing out considerations I'd missed. Later, the focus of our project shifted so the document needed rewriting - this time my manager said 'ok, you've got this - give it a go and shout if you get stuck, then we can review'. And now, I write those documents without needing a review (but with the option there if needed). It wasn't so much a lack of skill on my side as a lack of experience, and sometimes confidence - so helping build both of those can be really helpful!I don't think this is a bad reflection on either of you, it's just a clash of styles which happens all the time. The great news is that you're aware of it and actively trying to do something about it - that's half the battle! And to echo another comment, ask your reportee what they want - if they don't know, that's ok - but they might have more sense of what they need than you think! :)
My 2 cents without knowing the detail of your situation... hope one of these / a combo would be useful.1. What are you trying to achieve working with this person? Is it only the definitive business outcome? (which I assume is happening from what you described, but only with painstaking micromanagement which bothers you). Or you also want to spend time making it work for both of you - for him to contribute and develop professionally and for you to become a more savvy, all rounded manager, not only adhering to what you are already good at / which style you prefer? If the latter, it's hard work but I think it's very rewarding. But the other person needs to agree to work with you too, and meet you halfway. If you can get this mutual understanding with him that's the best. If not, sometimes you'll have to go about it alone for a while until he starts to understand. 2. Is this person meeting the expectations? If YES, see more below. If NO, then maybe it's time to progressively 'manage him out.' This does not have to mean firing people and it really is the last resort. From what you described, it sounds to me he is trying to perform without bad attitude whatsoever. From experience, often times you can help the team member find a better suited job and/or manager within the organization. (WIN-WIN). Talk to HR to support you in job skills mapping and exhaust whatever initiatives inside the org for mobility. Make sure the person understands you are helping him not trying to get rid of him (if you really mean it). In many situations people are just in the wrong job / team / even company and it's like a matching exercise gone wrong. 3. Try 'peer pressure' in a good way. Once I got dropped onto a team that was quite dysfunctional. When they were ready, we progressively shifted to more team stand up rather than individual 1:1 with me. This increases transparency, gives all of us opportunities to understand each other's work and more importantly, specific challenges. They also started to feel regularly the interdependencies on what they believed to be 'their own tasks / projects' (read: territory) and understand how and what they deliver could have large impacts on others completing their work too, and vice versa. The beginning can be rocky, but in time it usually improves team morale and collaboration. The manager plays more like a mediator role to facilitate them finding solutions on their own rather than just telling and managing them on what to do. If you'd like, you can see it as delegating part of your responsibility to micromanage him to his peers. (WIN-WIN).4. Think like a coach and put in some work to really find out what this person needs. Is it a lack of self confidence? A lack of trust between you two? A lack of understanding of what the job requires / what your preferred style is? A lack of self awareness? Then assign training / buy him books / introduce mentors / etc. Sometimes it works, sometimes it doesn't. But at least you tried. This is related to #1 above - do you want to and can afford to put in the hard work, or finding a quick solution is required. It's important to remember there is no judgement here. We all have our business obligations to fulfil and if the stakes are high, there is no good thinking "I really want to be a 'good' manager" and drag on. It's also related to #2 - is he really a misfit for this team but could add much value elsewhere? 5. As with other tasks that we don't like repeatedly doing, see if you can find tools to automate it. Not sure if it applies to your line of work with him, but for example, find project / task management tools that can be agreed upon at the beginning, be specific about it, set reminders, alerts, progress reports to you and him. So you delegate this part that you don't like but he needs to the machine, and when you two meet you can focus on more likeable and valuable activities (e.g. working on #4 above, coaching on confidence / trust / etc.). (WIN-WIN).I've worked with a myriad of high performing and not-so-performing people with strong characters, and I have to say the most rewarding is finally after much efforts you've cracked it and could really bring people together. These days I also think less of 'managing people' and more how you inspire and help bring out the best of each individual (and avoid the not so pretty sides). It really drives me nuts sometimes in the middle of it, but once things gradually improve it's a very rewarding experience. The 'manager' in this case also learns and benefits a lot. My teams and peers also bring out the better side of me. (WIN-WIN). Hope this helps a bit. Good luck and let us know how it goes!
Pick up a book or course on situational leadership, it will help you tremendously.