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[Edited Transcript from Podcast]
This podcast is going to be focused on how to be a better manager and leader. It's going to be focused particularly on the startup setting, which has its own unique challenges, but the approach is applicable pretty much anywhere. I will start off with a little bit about myself and why I'm doing this, and then I'm going to talk about the basics of being a first time manager. You might think, “Well, I've been a manager for a while, I don’t really need this.” I promise you that there are things you can learn and, at the very least, I would love your feedback and any input you have. Management is definitely not something that there's a perfect methodology for, and everyone certainly has their own opinions on it. I'm always looking to hear from others about how they approach it.
I love managing people. I think it is my calling in life. I really love helping people be their best selves in a professional setting, and I have found that being a great manager is the key to enabling that both for the individuals in a team as well as an entire organization.
My background
I'm from the Boston area. I'm a huge Red Sox fan and I love Dunkin’ coffee. I'm definitely what they refer to as a Masshole. I went to school at WashU in St. Louis and got my undergraduate degree in business there. Out of school I worked for Capital One as an analyst for about a year and a half, and then in 2014 I moved over to Uber. Those were the early days of Uber, and I got to spend six years there in a bunch of different roles, first in Washington, DC, then Brazil, and then Mexico, which is where I got to build my first team. That team ran driver operations for all of Latin America. After three years in Latin America, I moved over to JUMP, which was the bike and scooter division of Uber at the time. At JUMP, I built up the central operations team for the United States and Canada. And then in early 2020 I left the company after six years to take some time off.
My time off was intended to be traveling, but of course the pandemic hit and I got stuck in my apartment in San Francisco, which wasn't quite what I had envisioned. I decided to start working with startups just to see if the things I had learned at Uber around being an effective leader and manager, and how to scale a business really quickly, were actually applicable elsewhere. I found that the answer was absolutely yes. I worked with a number of early stage startups and really enjoyed helping those founders find their way as they grew, and in particular helping them figure out how to build their teams and best set up their people for success.
After a year of startup consulting, I moved over to Incredible Health where I was the Vice President of Operations for a little over a year. In that role, I built up the company’s operations function and was part of the executive team. Ops started as a group of 8, and we grew to a team of 60 by the time I left. One of the things that I'm most proud of is that the six managers I hired for that team, many of whom had never had any prior management experience, were able to develop working alongside me into exceptional people managers, and leaders who are going to serve that organization for a long time to come.
Now I'm focused again on my consulting work and, and coaching early stage founders.
I love working with startups. I think that the startup world is simply fascinating and there are lots of unique challenges. You can see me write about some of them on my blog, which you can find at maxwennekerconsulting.com. I would love to hear from you all about challenges you're facing in your own organizations, things that I can write about or talk more through to impart my wisdom and what I've learned from many years of experience in the fast growth startup world.
What does it mean to be a good manager?
Let's talk about management. First I want to start with what I think of as the main responsibilities that a manager has. It really just boils down to one thing more than anything, but I don't know that it's commonly thought of this way. I think your main responsibility as a manager is simply to enable your people to do their best work. And that means the people on your team and the people in your larger company who work with you.
The reason I say that it's to enable others to do their best work is that you as a manager don't really deliver much work yourself. You might step in to do some slides or there might be a player-coach setup where you're still delivering on work even though you're managing a team. But for the most part, the reason you're a manager is to help others be effective in their work. Otherwise, there's not really any reason for you to exist. So your job is to make sure that others are able to deliver the work that they need to in the most effective, productive, and efficient way possible.
This brings me to sort of the first lesson of management that I learned early on: a great manager needs to delegate. This often doesn't happen. What normally happens in early stage startups, or really any growing company, is the people who are promoted to manager. tend to be the ones who are the highest-performing individual contributors. Those are people who are not managers who are just doing work. When those individual contributors who are the highest-performing get promoted into manager roles, they already tend to have the personality of someone who does really great work and is used to being self-sufficient. When they get promoted into the manager role, there is a natural tendency on their part to keep doing that, to keep owning the responsibilities they had before. And it may not even be purposeful. It may just be that no one has told them otherwise, so they keep doing the things they were doing and then they also start managing people.
I learned the hard way from one of my first managers at Uber that that was not the way to go about being a great manager. The problem was that I kept doing all my own work, but all the people who were reporting to me needed my help. I was spending very little time with them, helping them figure out how to do work, and I was also not delegating work to them that they probably could have done better or spent more time on, and figured out a better way to go about executing that work. I got very lucky in my first managerial role that my boss actually told me I needed to go home for two days and write down everything that I did, make instructions for it, and then come back on Friday to figure out with her who on my team was going to own each of these things.
That was one of the best lessons I ever got as a manager. If she hadn't said anything, I probably would not have had a very long tenure as a manager, and it certainly would not have been a successful one. She helped me understand that I need to hand off work to my team in order to have the time to actually devote to being their manager. That means not doing work myself. That means helping them do work. Over the course of these podcasts we’ll talk about delegation, but I just wanted to call it out here: You need to devote your time, first and foremost, to helping your team do their work and not just doing work yourself.
How do we enable people to do their best work? I think it really boils down to just one thing, which is building trust. You as a manager need to create an environment where your team trusts you. That's the only way that you’ll be able to be effective, because that's the only way that they're going to believe what you tell them. That's the only way that they're going to be comfortable telling you what's going on, even when it's sometimes not what you would want to hear. That's the only way that they're going to have the buy-in to you to help them be successful, to help them learn, to be their coach, to be their cheerleader. It's the only way that you can come across as genuine.
When I start managing a new person, I think it's really helpful to start by understanding how that person works. If you're going to help them be the most effective people they can be, well, you need to understand them as people. I like to start and just ask some questions about who they are. Why are they doing this job? What aspects of this job or other jobs have they liked? What aspects have they disliked? I ask them to tell me about really great managers they've had in the past, because there are a lot of nuggets in there that'll probably help me figure out how to be a great manager for them. I also ask them to tell me about the worst manager they’ve had or a really bad manager they’ve had, and what are the things that made that relationship so bad or made them such a bad manager?
Sometimes people will say, particularly if they don't come from a typical corporate background, that they’ve never really had a manager before. In that case, you can also ask them about a supervisor, or someone who assigned them work or even a coach in a sport. Everyone has examples of people who have been in authority positions who rubbed them the wrong way and did not help them do their best work. The reason it's helpful to ask these things is that sometimes people don't really appreciate when they have a good manager, but they definitely know when they have a bad one.
One of the things that I most often hear is “I just didn't feel listened to.” That's probably the number one thing that folks tell me when, they joined my team or when I joined a team and they're reporting to me: “I had a manager who just told me what to do and didn't listen.” Just think of any environment where you don't feel listened to. Are you going to feel very comfortable in that environment? Are you likely to be as productive in that environment? Are you likely to stay in that environment? The answer, at least for me, is of course not. I imagine for most others, the answer is the same. Building trust is the key to helping ensure people feel listened to and cared about, and ultimately ensuring that people are doing what they're supposed to be doing.
One of the other things that I like to think about as a manager is it's my job to define where we're headed, the end goal that we're trying to get to. When I am managing a team, it is almost guaranteed that everyone in that team knows more about the problems that we are dealing with than I do. When I was at Incredible Health, I managed a team of customer service folks who worked directly with the nurses who applied on our platform to look for jobs. They certainly knew a lot more about those nurses and their experience and what they were looking for than I did. I could say where we needed to get to – for example, we want to make sure that we're onboarding 10% more nurses next month – but I’m definitely not going to be an expert in the way that we get there, because I don't necessarily have an understanding of all the problems that are stopping us from getting there. So I like to differentiate, as a manager, the “what” from the “how”. The “what” is definitely for a manager to define. This is where we're going. Our goal is to increase this metric by X percent. But the “how” is more collaborative. This is where two brains are better than one, because you as a manager only have a limited amount of knowledge around how everything works in your organization. This is where you really need to defer to your people and trust in the information they're providing you to be able to make the most effective decisions around how to get there. The most successful managers are focusing on the “what”, and then helping guide their team to get the best “how” possible, but they are not dictating it.
It’s really important, for first time managers in particular, to separate the “what” from the “how”. You're managing a team of subject matter experts who know more than you do, and therefore they're gonna understand that “how” a lot better. They're also going to come up with some ideas for the “how” that you may not have thought of yourself. It's your job as a manager not to come up with all the ideas, but rather to create an environment where others are able to come up with ideas and where you are the rock tumbler that takes an idea from an unpolished rock that you find on the beach and tumble it. Bounce that idea off your team and enable discussion in a way that turns it into a beautiful, shiny rock that you want to put on your mantle. I don't know if that was the best example, but I like to think about management as being the rock tumbler.
Priorities as a manager
So we've talked now about what your main responsibility as a manager is, which is enabling your team to do their best work. And we've talked about how to get there, which is first and foremost to build trust. Now, how to most effectively allocate your time. What are your priorities as a manager? We're going to focus on the very basics today. Even some of these basic concepts are very helpful, both for first time managers and for managers who've been doing it a while who maybe aren't getting all the results that they're looking for. If you are a founder who feels like there's more that you could get out of your organization or you're not quite heading in the right direction, it's very possible that you are causing that by your action or your inaction. It's all related to how you're managing your team and how you're enabling them.
The worst managers that I've had are the ones that have mostly focused upward and outward. These are managers who are, for lack of a better word, “yes men”. They're really focused on creating positive relationships with their managers and their peers. Then as a secondary responsibility they're focused on interactions with their own team. What I find happens in those situations is that I have often not felt listened to by my manager when they're focused so much on upward management, on talking to their superiors and making sure they're doing what their superiors want. They’re often just coming to me and saying, “this is what X or Y superior of mine said needed to happen”. And they're not really listening to me, trying to figure out how to make it happen, or why that might not be realistic, or what context my manager needs in order to be able to make effective decisions.
The best managers prioritize first and foremost interactions with their team, and in particular do a lot more listening than they do talking. If you talk to previous direct reports of mine you'll pretty consistently hear them say, “Max asked me a lot of questions”. The reason I do that is because I am assuming, as I think most managers should, that I know nothing and I am here to learn about the challenges that the person is facing, that their team is facing, that the company is facing. I'm here to absorb information and then help make decisions not dictated by what I think I know. So I spend a lot of time just asking questions, trying to understand. As a manager, one of my most effective tools is active listening, where I'm not just trying to ask them questions and hear what they say, but also repeat back to them. Summarize what I thought they said so I can make sure that I understood and so they can know that I understood. So sometimes my one-on-ones can run a little on the longer side, but I find that that's a good thing because it's an exchange of information. It's not a dictation by me. It's me getting all the possible information from my team members, so that 1) they can feel heard and 2) just as importantly to the business. I have all the information I need to make effective decisions and to speak with my superiors to make sure they have the information they need to make effective decisions.
The best information is going to come from the people actually doing the work, which are the people reporting to you and reporting to the managers who report to you. So all that's to say that I think it's really important as a manager to prioritize interactions with your team members first and everything else should come after that.
One-on-ones
Interactions with your team take the form of one-on-ones. A one-on-one is a weekly or biweekly meeting between you and each of your direct reports individually. It is meant to be a time where you can check in on the progress of their work, check in on how they're doing as both professionals and as human beings, and also provide them additional context on what's going on in the broader organization. These are things such as new initiatives or new priorities that they need to be aware of in order to do their jobs effectively. It's also meant to be a problem solving session where they can bring up things that are blocking them from accomplishing this task or this project in a timely manner and they need your help to unblock those things. My job as a manager is to then go do the blocking and tackling and clear the way for them so that they can be effective.
I always tell my first time managers to schedule their one-on-ones and then never ever cancel them unless they’re on vacation. You could move a one-on-one around if you need to, but make sure to have them consistently, because that's the way that you get the best information about what's going on in your business, in your team, and that's the way that your team members will feel prioritized, and therefore that you build trust with them. Sometimes you'll have one-on-ones that maybe aren't super informative or very long, but just the act, the habit of having one-on-ones on a regular basis and asking good questions around what your team is up to versus what they want to be doing versus what they think needs to happen that they're not able to accomplish currently, will help you build that trust. You're also going to get a ton of information from them around key decisions that you need to make as a leader.
Management resources
I want to close with a couple books that I think are game changers for a first time manager. Managers that I’ve worked with have given me the positive feedback that these books were incredibly helpful to them. These books just think about management from a slightly different perspective than you might get in the classroom.
The first book is called First Break All the Rules, What The World's Greatest Managers Do Differently. It's from the Gallup organization. There's a lot of management theory that's based on what one person thinks makes a good manager, and not necessarily based on reflection from actual experience. The reason I like this book is that it does a poll. They ask organizations for who their best managers are, and then they go interview those managers and see what they do that's different than the worst managers. The result is literally a list of best practices from these great managers across a bunch of different companies as to how they get the best results and how they are such effective people managers.
The second book is called Radical Candor: Be a Kick Ass Boss Without Losing Your Humanity. That's by Kim Scott. This book talks about the importance of challenging your direct reports while also caring about them. The book is focused on this 2x2 matrix of challenging and caring as the two axes and how you really want to fall into the bucket of challenging directly, but also caring deeply about your team. If you fall into just one of those buckets or neither of them, you end up being a very non-optimal manager.
Thanks so much for listening. Again, my name is Max Wenneker. If you want to follow this podcast, you can find it on Spotify as well as linked on my website maxwennekerconsulting.com. Please feel free to reach out on my website or on LinkedIn if you want to chat about your own managerial challenges. I do offer coaching services for leaders of startups. I really like helping leaders figure out how to be the most effective they can be and how to make their businesses succeed. I would also love feedback on what we talked about today if there were certain pieces of this that were more helpful than others, or things you really want dived into more in future podcasts.