Figuring out how to manage direct reports

Before starting with IDinsight, i had only limited managerial experience — mostly managing field managers and survey teams. i certainly had not given much thought to management or how to do it in a meaningful way, beyond a general sense of wanting to get good work out of my team as well as keep them happy. Nor had i really had what i considered to be a stellar experience of being managed. i had a great academic committee, for example, but i wouldn’t hold that up as the best way to manage people. And i have had an array of other less-than-fun managers, including micro-managers and credit-stealers, in organizations that didn’t necessarily put any value on spending time and effort on becoming a better manager. 

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i found it quite daunting, then, to find myself with one — and later two — direct reports in an organization that takes management, feedback, and professional development quite seriously (one of the things that makes IDinsight a fab place to work). (Note that the folks i manage are a few years out of undergrad, sometimes with a 1-year masters degree.) 

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i certainly talked to my direct reports every day (when i first started, there were only six of us sitting in a very open office, so it would have been quite hard to not talk to my direct report!) but i still felt it wasn’t enough: it neither (intentionally) set him up well to reflect on his work and his growth, nor set me up well to do performance reviews and other necessary things. 

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Early in my tenure with IDinsight, i had a very positive experience of working through the book Managing to Change the World with a colleague with more management experience inside and outside IDinsight. One of the big takeaways (for me) from the book and our conversations was the usefulness of setting aside explicit time/space for non-project check-ins — no matter how much you already talk to discuss project work or chat informally. The book, my colleague, and other colleagues helped provide a lot of great ideas that i crowdsourced…

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…and then i found myself totally overwhelmed by the prospect of trying to remember all those good questions. 

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So, as has become my management habit/style over the past 1.5 years, i created a spreadsheet, with rows for topics on which i want to check-in regularly and columns for each week. This functions as a semi-structured interview guide as well as a recording device for me, so that i can look at previous notes and patterns as well as have notes when i need to fill out performance reviews (i also find completing performance reviews very daunting and still struggle with recording peak areas and challenge areas on a daily or weekly basis!).

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At first, i worried it would seem too rigid, if i had my laptop out during our chats and i was obviously reminding myself of the questions i wanted to ask and typing down notes. But overall, this seems not to have been a major problem. And, actually, have heard from my direct reports that they like knowing some of the questions i’ll ask in advance, so that they can reflect on them before we meet.

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The system is certainly not perfect and is continuously updated. But one good sign (i think) is that my direct reports have started using a similar system with their direct reports (Field Managers, who are awesomely permanent staff at IDinsight) and use some of the questions that i generated and that they particularly like.

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Although i created the initial set of questions, over the weeks and months, some have been dropped and others have been suggested and added (e.g.“Heather, will you please check in with me about X each week to help hold me more accountable to it?”).

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One thing i have definitely learned over the past 1.5 years is that attempting to be a good manager takes time (and effort). These non-project check-ins, which we do weekly on Monday mornings or early afternoons (i strive for ‘management Mondays’), take about an hour and usually result in about 15 – 30 minutes of follow-up work based on the conversation (sending a paper i promised during our check-in, delivering a shout-out to someone i’ve discovered helped on our project in some unseen way, etc). i’ve had to learn to budget in that follow-up time so that the rest of my schedule isn’t thrown off.  

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Below are the questions i currently aim to ask every week, though we don’t always make it through all of them (which i think is ok); as noted above, it should be considered a semi-structured interview guide to help have a conversation on important topics that can easily be elided in favor of easier small talk or in favor of focusing strictly on the project work. As much as possible, my goal is to help raise important issues — but give my direct reports a chance to come with ideas of how to tackle those issues. Theoretically, this is good professional development for them and, ideally and honestly, a little less work for me! 

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Hope this post is useful to some other folks who are attempting to figure out how to be a good manager, despite not necessarily having had one before or not having worked in an organization that took it seriously before. The questions below reflect IDinsight’s focus on professional development, organizational contribution, mission-focus, and values — as well as things stolen from the aforementioned management book.

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Feedback is, as always, welcome — particularly if you try out this list of questions and want to share your experience or, especially, if you have a go-to check-in question that works well for you!

  • Are you keeping healthy/well?
  • Are you happy and motivated? Really? Why/not?
  • What is the best thing that happened over the weekend?
  • What are two things that will make this a successful week for you?
  • What’s the toughest thing coming up this week? Anything that would make you feel more confident about tackling it?
  • Is there one tweak we could make that would make this a more manageable week?
  • Did it feel like you had roughly the right amount of work / working hours last week? Does it feel like you are working at a sustainable pace? On sustainable topics? (What would be sustainable to you?)
    • Reflecting back on last week, how many nights, if any, did you lose sleep over work?
  • Last week you were worried about [X] as the toughest thing coming up. How did it go? What worked and what could have been improved?
  • What is one new thing you learned or did last week related to professional development? (Here sometimes i probe for lessons related to written and oral communication, management, organizational development — folks have a gut tendency to equate professional development only with coding, even though technical proficiency is only one of our six performance review categories.)
  • What is one new thing you learned or did last week related to technical professional development?
  • Did this week throw up any gaps that you feel in your technical and professional development? Any thoughts on how we might address these?
  • What is one professional development task or goal you feel you did not achieve last week? How might you be able to fit it in in the following week?
  • Did you try any new strategies to manage your time or engage in deep work last week? Were these successful? Why or why not? What might you try this week?
  • What was the most interesting or helpful piece of feedback or advice you received last week?
  • Which aspect of your work gave you the most joy or fulfillment last week?
  • Is there that I could have done this past week to better support or coach you? What could I have done differently?
  • Do you feel like there is anything else you could be contributing to organizational growth and development that you are currently not (but would be interested in doing)?
  • Do you feel like we influenced any decisions, actions & social impact last week? What worked or didn’t in that process?
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