How to Suck a Little Less at Managing

A discussion of practical management strategies (and links to lots of other resources) for getting the most out of your team. Aimed mostly at new managers.

When you become a manager what you do, how you spend your time, and how you are measured all changes. You rely on people more than ever. And they rely on you more too.

Managing is hard. And rewarding. And interesting. And occasionally frustrating.

It’s also a learned skill. Parts of it are a little unnatural. It will take time, especially if you are a star individual contributor, to adjust.

Recently I've had conversations with four new managers I know well, and the common threads within those made me start thinking a lot about managing, and management, and what I’ve learned that’s made me a lot better now than I was a few years ago (and yes, I'm still new to the game too).

What follows is an attempt to distill the thoughts that have helped me into a framework and set of resources about being a leader and manager that I think are worth your time.

Point 1: You have to be you

Before I dive in it’s worth pointing out that everything that follows is just my take on what’s out there and what’s worked for me. It is certainly not supposed to be a list of all things you should blindly do. Lesson 1, I suppose, is that you’ve got to be authentic to you in how you work with your team.

Point 2: Your team needs to feel and BE heard

·       Set weekly 1:1s. Make them an hour. Try not to miss them. Don’t make these meetings purely tactical. It’s fine to discuss projects and blockers, but I’ve found more wide-ranging questions elicit feedback and emotions that can help you course correct. You need to really get at what will motivate people here and what things are preventing them from executing as well as possible. If you have experienced people on your team you can adjust this cadence, but I wouldn’t go longer than bi-weekly though. My hour-long weekly system stems directly from Andy Grove’s High Output Management, and my belief in the value of his advice, including specific details like making sure your 1:1 is at least 45 minutes, has only grown. This is a good quick and dirty chapter by chapter summary of the book by the way. Separately this discussion of good questions to cover in a 1:1 is useful, not just for the specifics but in the why of the questions.

·       Start-Stop-Continue – My manager, Marc Jacobs, brought this to CB Insights and it is incredible. Every quarter or half year, we’ve gotten together as a team and brainstormed things we want to start doing as a team, things we want to stop doing, and things we want to continue to do. The team writes these ideas on post-it notes and sticks them in the appropriate bucket before talking it out. While you can’t fix everything all at once, this practice lets you get a read on what you can fix and what your team’s concerns truly are. By the way, don’t mess with the format either. I think the combo of anonymous ideation on post-its followed by an open discussion does some good things.

·       Daily Stand-Ups – We do 10 minutes (it’s really closer to 15 for 5 people). It’s designed to be a go around of what you did yesterday, what you’re working on today, and any key blockers. Useful for you as a manager to get a pulse and keep accountability, but also tend to generate some informal and often highly efficient splinter conversations. It’s the new water cooler coffee break. Over time we’ve morphed into 3 daily stand-ups at 9:50 AM, and 1 Friday 4PM weekly recap check-in, and we’ve also added a 1 hour bi-weekly team meeting. So far this bi-weekly time has generated a lot of good conversations around our system architecture and given team members opportunities for peer learning that we wouldn’t otherwise have carved out.

·       Take your team out of the office – Happy hours or other team bonding activities. Reminders to them to get up and take a break or leave if they’re re seeming overworked, quarterly offsites. All of these things are important because you’re people first and work is only a part of a good life. Also, context switching and new environments open up new ways of interacting. You’ll hear different, valuable, things.

·       Celebrate your Team’s Wins and make it visible to the rest of the org – We run really fast here. Your company probably does too. It’s important to stop and give praise for good work. You also need to get used to being strategic about making sure that others know the good work your team is responsible for. It hope it goes without saying that when good things happen credit your team, whereas when your team messes up that’s on you. Lastly, write these accomplishments down somewhere. It’s amazing how many accomplishments you and your team will forget over the course of a year.

Whatever communication systems you choose I think ultimately they are all about achieving two goals:

·       Creating a repeatable process around how your team works

·       Creating transparency across the team in order to try to reduce unnecessary blockers

Sometimes that can look like a lot of meetings. And it is. But imagine if all of these structures create a 5-10% efficiency gain across each team member for the rest of their week. Or imagine that they prevent a star person from leaving. That’s time well spent on your end right?

·       Just make sure your meetings are good ones – I’m far from perfect here but ideally every meeting has someone owning the agenda and doing the work to create a good structure. Last tip here, don’t forget to audit your recurring meetings and overall time splits every once in a while. Which takes us to the next point.

Point 3: Your team needs focus to be efficient

 ·       Sprints++ – We’ve adopted the agile framework, and we work in 2 week Sprints. I find this helpful as it enforces a discipline to what we’re working on, a re-evaluation of priorities on a regular cadence, and a level-setting and knowledge sharing of what everyone is tackling across the team. You just have to be diligent about organizing Sprints and sticking to them (which is a difficult discipline that takes a lot of your time as a manager). I also find that Sprints aren’t a cure all. I’ve found supplementing them with project plans, specific deadlines, and periodic efforts to communicate the themes of our work are also helpful and the team in particular wants more of that broader work.

·       Saying No – Sequencing projects, being a gatekeeper for your team in order to keep them focused, managing expectations from your manager and others based on realistic assessments of trade-offs and resources…all of these things and more are part of the job. Especially as a front line manager this balance and ability to tactfully push back can be a very difficult thing to do. Just treat it as part of the job. A very important part of the job.

·       You need measurable KPIs – People need to know how they are doing and you need to be able to have objective discussions about their performance. This starts with goal setting. Some outcomes are strictly quantifiable. Establish these benchmarks. Measure them. Use them as the basis for feedback and evaluation. For projects that are a little more vague, find ways to measure performance, even if it’s about accuracy or speed of the work.

 Point 4: You need to prioritize your time

 ·       Calendar Blocking – This is really about optimizing yourself. As a manager you're going to be inherently cross-functional and I think that naturally creates more nodes of communication and thus more meetings. To manage this I wanted a better visual of where my time was going. So on my calendar repeated meetings are colored one way, 1-off meetings another, mission critical events another. I also block my time to get work done. I used to just tag this “work” but I now actually block the type of work I’m doing. This has helped me personally make sure that things I indicate are critical actually have time on them. I highly recommend blocking “thinking” time and treating that as sacred to Three other techniques I’ve found useful for making sure I stay on track personally:

·       3 Efficiency Hacks I like

o  MIT (Most Important Thing) - A list of 1-3 (and no more) of the most important things I need to get done that day. In theory you want to do one of these first thing.

o  Pomodoros – 1 task over a defined period of time, with an enforced break after. I do 35 minute blocks. You could also do this by going to a different spot in the office and only doing one type of work there. Here’s a primer

o  Don’t have email open – Don’t keep it open on your computer. Define when you will check it. It’s an obvious but seductive time suck.

·       Face-to-face is your friend – Got an email from your teammate asking for clarification? If you can, get up. Walk over to them to talk. Five minutes of discussion will solve a lot of things a lot faster and eat up a lot less cognitive bandwidth than multiple back and forths. Same thing with hipchat or slack. It’s distracting. I’ve also run into the trap of tone being hard to read in email (both sending and receiving). For many aspects of the job I vote you bias towards face-to-face or phone.

Point 5: Get used to asking people to do something for you. But don’t ask them to do something you wouldn’t do yourself*

·       Delegation with a Growth Mindset – This is one I continue to struggle with. After all, you’re used to making a lot of things happen on your own. But your job is to make sure things get done. It’s not (necessarily) to do them yourself, especially because you want to constantly empower and stretch your team. This article is a good read about how your one job is to fire yourself. Here’s another HBR article on how to let go without losing control. I like to remind myself that one sign of a good team is how well it operates without you.

o  Deciding on what to delegate:

Our CEO has a useful framework similar to the one below that evaluates projects on their complexity, potential impact, and risk. This lets you be flexible in terms of how often you check in or help. The newer the task for a person or the more mission critical the project the closer you should remain to it. It's something like this:

The second, often underlooked part of delegation, is balancing the mix of responsibilities for each team member. No one wants to spend all day doing drudgery and everyone wants to be challenged. Here’s another framework for thinking about how a person feels about the work they are doing:

 Point 6: You have a responsibility to grow the people on your team

·       Practice Radical Candor – I took this term from Kim Scott. She is a total badass and writes about why giving (and receiving) true, honest feedback is the most valuable thing you can do as a manager. Radical candor is hard. In fact, most of the time I think it is harder for you as a manager to give feedback then it is for someone else to receive it. Remember that people want to improve. As long as you are genuine about why you’re giving them feedback and you’ve taken time to build a relationship and cultivated a growth mindset these should be very positive moments even when they are difficult conversations. Another good read on honesty is from the head of Netflix’s HR (she is the woman who created their very famous culture code).

 ·       Give tough feedback in private, but as close to the moment as possible – Feedback is most effective in the moment, but be sure to deliver critical feedback in private

·       Establish Guidelines for when you are not needed – It’s easy to unintentionally become a blocker on things. To avoid this it’s important to establish guidelines around what you expect your team to do, or resolve, without involving you. David Marquet, a former Submarine Commander in the US Navy, developed a highly effective system called “intent based leadership”. His book, “Turn the Ship Around” is well worth reading, but the main idea here is that within the guidelines you’ve developed your team should clearly convey to you “what they intend to do” unless they hear otherwise from you. Here’s a good summary of the book.

·       Sometimes the best thing for your team is letting someone go – The first person I ever hired I had to fire two months later. It was brutal. I wrote about what I learned. Lots of startup people talk about how hiring slow, firing fast and I suppose there is some truth to that. It’s your job to hold the bar high. You set the standard and you hold the team accountable, period. I think it is also true that 9/10 times by the time you do fire someone for performance reasons the team is probably wondering what took so long. The person being let go should not be surprised by the decision. Finally you have to cover yourself and the company here. Follow the documented process.

 Point 7: A big part of your job is cross-functional alignment

Different teams have different priorities. You need to work within those so that you can (1) stay aligned, and (2) get the resources you need to hit your goals. It’s OK to say no, but you should communicate why the answer is a no (or a “no for now” as Brian P would say).   

 Miscellaneous Resources

·       Lessons from a manager I loved – Very good blog post

·       The weekly HBR newsletter usually has a good article or two

·       Firstround Review has a wealth of articles on managing (some linked below)

·       Evergreen Business Weekly – Every 2 weeks they curate a really good collection around a specific business topic. Many are management/scale related

·      Thinking about how you say what you say – Because voice matters

·       Fire all the managers – Provocative

·       Social Influence for Management

·       From C++ to the C-Suite: How Software Engineering Made Me A Better Executive

·        13 Exercises to Prep for Tough Work Situations

·       Hacking your Energy

·       Bezos’s Annual Shareholder Letters (high level, Anand recommendation)

·       Who’s Got the Monkey and a summary where no login needed (this is a priceless framework)

Great Books

·       Andy Grove – Highoutput Management

·       David Marquet - Turn the Ship Around

·       Richard Rumelt - Good Strategy, Bad Strategy – Less management, more high level. Brilliant book. Here’s a 90 minute lecture from the author that’s also quite good

·       Ben Horowitz – The Hard Thing about Hard Things

·       Ray Dalio – Principles (controversial)

·       Dale Carnegie – How to Win Friends and Influence People

·       Daniel Kahneman – Thinking Fast and Slow

·       Tim Ferris – Tools of Titans

·       Robert Cialdini – Influence: The Psychology of Persuasion (meta, very trippy)